A truly unique opportunity to own well over half an acre of ultra-private property, set far back from the road, with 12 feet of deeded Lake Sybelia frontage and access. This charming, updated, cottage-style home offers 3 bedrooms plus a den, 2.5 bathrooms, and plenty of separate flex space for entertaining, both inside and out. The family room is light and bright with skylights, terracotta-look tile floors, a beamed ceiling, a window seat, and brick mantle. The inviting kitchen features smoky blue cabinetry, a farm sink, new refrigerator, tile counters and floors, and opens to the dining room and a light-filled sitting room with built-in wet bar, wine storage, and accordion doors opening to the backyard. The adjacent Florida room has walls of windows overlooking the yard and a door leading to the backyard. The split-bedroom floor plan offers two bedrooms sharing an updated hall bath with tile floors, quartz counters, dual sinks, and multiple showerheads, including a rain shower. The separate primary suite, part of the 2001 addition, is spacious with three closets and French doors opening to a brick patio. The primary bath features a single-sink vanity, built-in cabinetry, and shower. An attached den with a half bath and closet provides flexible space for an office, nursery, or additional sitting area. Additional features include wood floors in all bedrooms, ceiling fans, plantation shutters, a water softener, and interior laundry. Recent updates include roof (2019), AC (2023), insulation (2025), electric panel (2024), hot water heater (2026), lighting, fixtures, a new electric fence, and more. A long private driveway leads to a large circular drive at the rear of the property. A detached shed has electricity and running water. The fully fenced backyard offers mature landscaping, in-ground irrigation, and ample space and flexibility for outdoor living, entertaining, RV or boat storage, or for future improvements, additions, or to create a custom new build. The property includes a deeded 12-foot-wide strip of Lake Sybelia frontage, providing usable lake access and potential for an EZ floating dock; see survey/attachment for details. Ideally located near the new Maitland Public Library, currently under construction and expected to open in 2027, as well as the Enzian Theater, Maitland Art & History Center, and Lake Lily Park, and just minutes to Winter Park and Downtown Orlando. Assigned schools include Lake Sybelia Elementary, Maitland Middle, and Edgewater High. Lot size is approximately 0.65 acres per public record, including the portion of the parcel extending into Lake Sybelia; approximately 0.58 acres is dry land. Buyer to verify all measurements, property boundaries and lake access.

3 Beds ⋅ 3 Baths ⋅ O6436185 MLS

A truly unique opportunity to own well over half an acre of ultra-private property, set far back from the road, with 12 feet of deeded Lake Sybelia frontage and access. This charming, updated, cottage-style home offers 3 bedrooms plus a den, 2.5 bathrooms, and plenty of separate flex space for entertaining, both inside and out. The family room is light and bright with skylights, terracotta-look tile floors, a beamed ceiling, a window seat, and brick mantle. The inviting kitchen features smoky blue cabinetry, a farm sink, new refrigerator, tile counters and floors, and opens to the dining room and a light-filled sitting room with built-in wet bar, wine storage, and accordion doors opening to the backyard. The adjacent Florida room has walls of windows overlooking the yard and a door leading to the backyard. The split-bedroom floor plan offers two bedrooms sharing an updated hall bath with tile floors, quartz counters, dual sinks, and multiple showerheads, including a rain shower. The separate primary suite, part of the 2001 addition, is spacious with three closets and French doors opening to a brick patio. The primary bath features a single-sink vanity, built-in cabinetry, and shower. An attached den with a half bath and closet provides flexible space for an office, nursery, or additional sitting area. Additional features include wood floors in all bedrooms, ceiling fans, plantation shutters, a water softener, and interior laundry. Recent updates include roof (2019), AC (2023), insulation (2025), electric panel (2024), hot water heater (2026), lighting, fixtures, a new electric fence, and more. A long private driveway leads to a large circular drive at the rear of the property. A detached shed has electricity and running water. The fully fenced backyard offers mature landscaping, in-ground irrigation, and ample space and flexibility for outdoor living, entertaining, RV or boat storage, or for future improvements, additions, or to create a custom new build. The property includes a deeded 12-foot-wide strip of Lake Sybelia frontage, providing usable lake access and potential for an EZ floating dock; see survey/attachment for details. Ideally located near the new Maitland Public Library, currently under construction and expected to open in 2027, as well as the Enzian Theater, Maitland Art & History Center, and Lake Lily Park, and just minutes to Winter Park and Downtown Orlando. Assigned schools include Lake Sybelia Elementary, Maitland Middle, and Edgewater High. Lot size is approximately 0.65 acres per public record, including the portion of the parcel extending into Lake Sybelia; approximately 0.58 acres is dry land. Buyer to verify all measurements, property boundaries and lake access.

790 S Lake Sybelia Drive, Maitland

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234

$459,000

Virtually Staged. PRICED BELOW APPRAISAL! Exceptional value in a desirable Maitland location! Whether you’re starting out, slowing down or somewhere in between, this home is a must see. Located in an absolutely delightful neighborhood and beautifully renovated in 2026. Your new home is move-in-ready and features new windows, flooring, hot water tank, entry and garage doors, as well as new exterior siding and the roof and HVAC were replaced in 2023. Soaring 14-foot ceilings and expansive sliding glass doors fill the home with natural light and create a bright, inviting atmosphere. The beautifully updated kitchen is a true delight, featuring quartz countertops with a waterfall edge, abundant cabinetry, pantry, a smart digital faucet with temperature display, and new stainless-steel appliances. The cozy breakfast nook overlooks the spacious, fenced backyard and is the perfect spot to enjoy your morning coffee. The desirable split-bedroom floor plan offers privacy, while the primary suite opens directly to the generously sized screened porch—perfect for relaxing or enjoying the Florida lifestyle. The location is hard to beat, with the SunRail, Lake Lily Park, shopping, dining, and entertainment all nearby. And best of all, NO HOA! A beautifully renovated home in a fantastic location and priced to deliver outstanding value—don't miss it!

3 Beds ⋅ 2 Baths ⋅ O6434035 MLS

Virtually Staged. PRICED BELOW APPRAISAL! Exceptional value in a desirable Maitland location! Whether you’re starting out, slowing down or somewhere in between, this home is a must see. Located in an absolutely delightful neighborhood and beautifully renovated in 2026. Your new home is move-in-ready and features new windows, flooring, hot water tank, entry and garage doors, as well as new exterior siding and the roof and HVAC were replaced in 2023. Soaring 14-foot ceilings and expansive sliding glass doors fill the home with natural light and create a bright, inviting atmosphere. The beautifully updated kitchen is a true delight, featuring quartz countertops with a waterfall edge, abundant cabinetry, pantry, a smart digital faucet with temperature display, and new stainless-steel appliances. The cozy breakfast nook overlooks the spacious, fenced backyard and is the perfect spot to enjoy your morning coffee. The desirable split-bedroom floor plan offers privacy, while the primary suite opens directly to the generously sized screened porch—perfect for relaxing or enjoying the Florida lifestyle. The location is hard to beat, with the SunRail, Lake Lily Park, shopping, dining, and entertainment all nearby. And best of all, NO HOA! A beautifully renovated home in a fantastic location and priced to deliver outstanding value—don't miss it!

761 Robinhood Drive, Maitland

Listing courtesy of RE/MAX ASSURED. 800-393-8600

$979,000

Welcome to 1281 Wellington Terrace, a beautifully maintained 4-bedroom, 3-bath home offering 2,931 square feet in one of Maitland’s most desirable and established neighborhoods. With spacious interiors, thoughtful updates, and deeded access to Lake of the Woods, this home offers an exceptional combination of comfort, versatility, and location. One of the home’s most distinctive features is its rare split floor plan with two private primary suites positioned on opposite sides of the home. The second primary suite also features its own separate entrance, offering exceptional flexibility for multigenerational living, extended family, guests, a private home office, or an independent retreat—all while maintaining privacy within the main residence. Inside, soaring beamed ceilings and skylights fill the home with natural light, while a beautiful statement fireplace anchors the main living area. The open kitchen flows effortlessly into the gathering spaces and is complemented by a separate butler’s pantry and spacious laundry room, providing the extra storage, functionality, and convenience that make everyday living and entertaining effortless. Recent improvements include new windows throughout and a three year old roof, adding comfort, efficiency, and peace of mind. An expansive Florida room opens the home to the private, low-maintenance backyard, creating a wonderful extension of the living space and an inviting setting for entertaining, morning coffee, or simply relaxing and enjoying Florida living year-round. Ideally located in Maitland’s sought-after Wellington community, residents enjoy deeded lake access, highly rated Seminole County schools, and convenient access to Winter Park’s Park Avenue, with its renowned restaurants, boutiques, museums, and cultural attractions. Nearly 3,000 square feet, two private primary suites, generous living spaces, beautiful architectural character, and an outstanding Maitland location—1281 Wellington Terrace offers the space, privacy, and flexibility to live beautifully at every stage of life.

4 Beds ⋅ 3 Baths ⋅ O6433131 MLS

Welcome to 1281 Wellington Terrace, a beautifully maintained 4-bedroom, 3-bath home offering 2,931 square feet in one of Maitland’s most desirable and established neighborhoods. With spacious interiors, thoughtful updates, and deeded access to Lake of the Woods, this home offers an exceptional combination of comfort, versatility, and location. One of the home’s most distinctive features is its rare split floor plan with two private primary suites positioned on opposite sides of the home. The second primary suite also features its own separate entrance, offering exceptional flexibility for multigenerational living, extended family, guests, a private home office, or an independent retreat—all while maintaining privacy within the main residence. Inside, soaring beamed ceilings and skylights fill the home with natural light, while a beautiful statement fireplace anchors the main living area. The open kitchen flows effortlessly into the gathering spaces and is complemented by a separate butler’s pantry and spacious laundry room, providing the extra storage, functionality, and convenience that make everyday living and entertaining effortless. Recent improvements include new windows throughout and a three year old roof, adding comfort, efficiency, and peace of mind. An expansive Florida room opens the home to the private, low-maintenance backyard, creating a wonderful extension of the living space and an inviting setting for entertaining, morning coffee, or simply relaxing and enjoying Florida living year-round. Ideally located in Maitland’s sought-after Wellington community, residents enjoy deeded lake access, highly rated Seminole County schools, and convenient access to Winter Park’s Park Avenue, with its renowned restaurants, boutiques, museums, and cultural attractions. Nearly 3,000 square feet, two private primary suites, generous living spaces, beautiful architectural character, and an outstanding Maitland location—1281 Wellington Terrace offers the space, privacy, and flexibility to live beautifully at every stage of life.

1281 Wellington Terrace, Maitland

Listing courtesy of NOELKE REALTY. 407-607-7166

$959,000

Tucked at the end of a quiet cul-de-sac beneath a canopy of mature oaks, this beautifully maintained Maitland home offers space, privacy, and thoughtful updates throughout — all within a top school zone just minutes from Winter Park and downtown Orlando. A paver driveway winds through lush, established landscaping to a covered entry framed by an arched transom window, with a tile roof crowning the home. Inside, the open floor plan unfolds around a striking floor-to-ceiling tile fireplace anchoring the family room, with vaulted ceilings, skylights, and French doors that flood the space with natural light and open directly to the screened lanai. The kitchen is a true centerpiece — rich wood cabinetry, granite countertops, a tile backsplash, and stainless steel appliances including a French door refrigerator, all overlooking the family room. A bright, bowed breakfast nook wrapped in windows offers the perfect everyday dining spot, while a separate formal dining room and living room provide room to entertain. This is a true split floor plan, with the primary suite privately tucked away from the secondary bedrooms for maximum peace and quiet. The primary retreat features a spacious layout, built-in bookshelves, and an oversized walk-in closet with custom shelving. The en-suite primary bath features dual vanities, a walk-in glass shower with a bench, and elegant lighting throughout. A versatile bonus room/loft with a full wall of built-in shelving and columned entry adds flexible space for a home office, playroom, or media room. A separate storage loft offers abundant built-in shelving — ideal for keeping everything organized and out of sight. Three additional bedrooms host generous closet space, and a well-appointed powder bath rounds out the main living areas. The oversized utility room impresses with abundant cabinetry, a utility sink, and stone countertops — plenty of room for laundry, storage, and more. Step outside to your own private oasis: a screened, covered lanai wrapping a sparkling pool, all enclosed by mature landscaping and a fully fenced yard — perfect for Florida indoor-outdoor living, entertaining, or simply relaxing under the trees. Located in a sought-after Maitland neighborhood with easy access to top-rated schools, shopping, dining, and major roadways.

4 Beds ⋅ 4 Baths ⋅ O6430446 MLS

Tucked at the end of a quiet cul-de-sac beneath a canopy of mature oaks, this beautifully maintained Maitland home offers space, privacy, and thoughtful updates throughout — all within a top school zone just minutes from Winter Park and downtown Orlando. A paver driveway winds through lush, established landscaping to a covered entry framed by an arched transom window, with a tile roof crowning the home. Inside, the open floor plan unfolds around a striking floor-to-ceiling tile fireplace anchoring the family room, with vaulted ceilings, skylights, and French doors that flood the space with natural light and open directly to the screened lanai. The kitchen is a true centerpiece — rich wood cabinetry, granite countertops, a tile backsplash, and stainless steel appliances including a French door refrigerator, all overlooking the family room. A bright, bowed breakfast nook wrapped in windows offers the perfect everyday dining spot, while a separate formal dining room and living room provide room to entertain. This is a true split floor plan, with the primary suite privately tucked away from the secondary bedrooms for maximum peace and quiet. The primary retreat features a spacious layout, built-in bookshelves, and an oversized walk-in closet with custom shelving. The en-suite primary bath features dual vanities, a walk-in glass shower with a bench, and elegant lighting throughout. A versatile bonus room/loft with a full wall of built-in shelving and columned entry adds flexible space for a home office, playroom, or media room. A separate storage loft offers abundant built-in shelving — ideal for keeping everything organized and out of sight. Three additional bedrooms host generous closet space, and a well-appointed powder bath rounds out the main living areas. The oversized utility room impresses with abundant cabinetry, a utility sink, and stone countertops — plenty of room for laundry, storage, and more. Step outside to your own private oasis: a screened, covered lanai wrapping a sparkling pool, all enclosed by mature landscaping and a fully fenced yard — perfect for Florida indoor-outdoor living, entertaining, or simply relaxing under the trees. Located in a sought-after Maitland neighborhood with easy access to top-rated schools, shopping, dining, and major roadways.

1889 Berkeley Court, Maitland

Listing courtesy of MERDIAN REALTY LLC. 407-230-8093

$674,000

**BOATING/LAKE ACCESS** Welcome to 553 Arapaho Trail, where timeless MID-CENTURY CHARM meets thoughtful modern living in the highly sought-after DOMMERICH ESTATES community of Maitland. Offering OVER 1,500 SQUARE FEET of beautifully maintained living space, this 3-BEDROOM, 2-BATHROOM HOME features a desirable SPLIT FLOOR PLAN designed for both privacy and everyday comfort. From the moment you arrive, you'll appreciate the exceptional curb appeal with LUSH, MATURE LANDSCAPING, a NEWLY PAINTED EXTERIOR, and an EXTRA-WIDE, EXTRA-LONG BRICK PAVER DRIVEWAY with room for up to SIX VEHICLES. Inside, the home's original character has been carefully preserved while incorporating today's most important updates, including a NEW ROOF (2025), NEW GUTTERS, WHOLE-HOUSE REPIPE, ELECTRICAL UPGRADES, HARDWOOD FLOORING THROUGHOUT, NEW KITCHEN APPLIANCES, an UPGRADED PRIMARY EN-SUITE, stylish UPDATED LIGHTING FIXTURES, an EXTENDED ATTIC WITH ABUNDANT STORAGE, and a PAINTED GARAGE FLOOR. One of the neighborhood's rare homes with BURIED ELECTRICAL SERVICE, the property also offers a cleaner streetscape and added peace of mind. Step outside and discover your own private backyard retreat featuring an INCREDIBLE SCREENED-IN POOL, an expansive BRICK PAVER POOL DECK, and a charming BRICK PAVER GARDEN WALKWAY winding through beautifully landscaped grounds—perfect for entertaining or relaxing year-round. Beyond the home, DOMMERICH ESTATES continues to impress with its welcoming sense of community and location within one of Central Florida's most desirable school districts, originally designed around A-RATED SCHOOLS to make walking and biking to class safe and convenient. Residents also enjoy access to a VOLUNTARY, LOW-COST HOA that includes a PRIVATE BOAT RAMP to the WINTER PARK CHAIN OF LAKES, opening the door to BOATING, PADDLEBOARDING, FISHING, and unforgettable days on the water. The CITY OF MAITLAND offers the perfect balance of convenience and charm with its WALKABLE NEIGHBORHOODS, beautiful parks, local festivals, downtown concerts, and community events, while world-renowned PARK AVENUE in Winter Park is just minutes away for AWARD-WINNING DINING, BOUTIQUE SHOPPING, ART GALLERIES, and weekend brunch. This is more than just a home—it's an opportunity to experience one of CENTRAL FLORIDA'S MOST BELOVED NEIGHBORHOODS and lifestyles.

3 Beds ⋅ 2 Baths ⋅ O6427049 MLS

**BOATING/LAKE ACCESS** Welcome to 553 Arapaho Trail, where timeless MID-CENTURY CHARM meets thoughtful modern living in the highly sought-after DOMMERICH ESTATES community of Maitland. Offering OVER 1,500 SQUARE FEET of beautifully maintained living space, this 3-BEDROOM, 2-BATHROOM HOME features a desirable SPLIT FLOOR PLAN designed for both privacy and everyday comfort. From the moment you arrive, you'll appreciate the exceptional curb appeal with LUSH, MATURE LANDSCAPING, a NEWLY PAINTED EXTERIOR, and an EXTRA-WIDE, EXTRA-LONG BRICK PAVER DRIVEWAY with room for up to SIX VEHICLES. Inside, the home's original character has been carefully preserved while incorporating today's most important updates, including a NEW ROOF (2025), NEW GUTTERS, WHOLE-HOUSE REPIPE, ELECTRICAL UPGRADES, HARDWOOD FLOORING THROUGHOUT, NEW KITCHEN APPLIANCES, an UPGRADED PRIMARY EN-SUITE, stylish UPDATED LIGHTING FIXTURES, an EXTENDED ATTIC WITH ABUNDANT STORAGE, and a PAINTED GARAGE FLOOR. One of the neighborhood's rare homes with BURIED ELECTRICAL SERVICE, the property also offers a cleaner streetscape and added peace of mind. Step outside and discover your own private backyard retreat featuring an INCREDIBLE SCREENED-IN POOL, an expansive BRICK PAVER POOL DECK, and a charming BRICK PAVER GARDEN WALKWAY winding through beautifully landscaped grounds—perfect for entertaining or relaxing year-round. Beyond the home, DOMMERICH ESTATES continues to impress with its welcoming sense of community and location within one of Central Florida's most desirable school districts, originally designed around A-RATED SCHOOLS to make walking and biking to class safe and convenient. Residents also enjoy access to a VOLUNTARY, LOW-COST HOA that includes a PRIVATE BOAT RAMP to the WINTER PARK CHAIN OF LAKES, opening the door to BOATING, PADDLEBOARDING, FISHING, and unforgettable days on the water. The CITY OF MAITLAND offers the perfect balance of convenience and charm with its WALKABLE NEIGHBORHOODS, beautiful parks, local festivals, downtown concerts, and community events, while world-renowned PARK AVENUE in Winter Park is just minutes away for AWARD-WINNING DINING, BOUTIQUE SHOPPING, ART GALLERIES, and weekend brunch. This is more than just a home—it's an opportunity to experience one of CENTRAL FLORIDA'S MOST BELOVED NEIGHBORHOODS and lifestyles.

553 Arapaho Trail, Maitland

Listing courtesy of CREEGAN GROUP. 407-622-1111

$779,000

Virtually Staged. PRICE IMPROVEMENT, NEW ROOF, NEW AC, NEW HOT WATER HEATER before closing, making this beautifully updated 4-bedroom, 2-bath split-plan home offering approximately 2,280 square feet of living space, ideally situated on a quiet cul-de-sac in desirable Maitland, an amazing value. This well-maintained residence is zoned for highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High School. The spacious floor plan features oversized rooms throughout, including formal living and dining areas, a large family room with a decorative stone accent wall and cozy fireplace, and a generous eat-in kitchen with granite countertops, updated cabinetry, and breakfast area. French doors provide abundant natural light and open to the screened patio and outdoor living spaces. Major improvements include updated flooring, fresh interior paint, double-pane windows, blown attic insulation, all-new ductwork, updated plumbing, a new electrical breaker panel, and complete home rewiring. Crown molding, recessed lighting, six-inch baseboards, and French doors add style and functionality throughout the home. The primary suite features French doors to the patio, a walk-in closet, dressing area, and a beautifully renovated bath with dual vanities, walk-in shower, travertine finishes, and updated fixtures. The secondary bathroom has also been fully remodeled with marble finishes, dual vanities, a new tub, and updated lighting. Outdoor highlights include a large rear deck, brick patio area, irrigation well and sprinkler system, and a fully fenced backyard with separate sections—ideal for pets, play, and entertaining. The perimeter fence was replaced and stained in 2017. Move-in ready and thoughtfully updated throughout, this exceptional home combines classic character, quality improvements, and an unbeatable location close to top-rated schools, parks, shopping, and dining.

4 Beds ⋅ 2 Baths ⋅ O6426674 MLS

Virtually Staged. PRICE IMPROVEMENT, NEW ROOF, NEW AC, NEW HOT WATER HEATER before closing, making this beautifully updated 4-bedroom, 2-bath split-plan home offering approximately 2,280 square feet of living space, ideally situated on a quiet cul-de-sac in desirable Maitland, an amazing value. This well-maintained residence is zoned for highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High School. The spacious floor plan features oversized rooms throughout, including formal living and dining areas, a large family room with a decorative stone accent wall and cozy fireplace, and a generous eat-in kitchen with granite countertops, updated cabinetry, and breakfast area. French doors provide abundant natural light and open to the screened patio and outdoor living spaces. Major improvements include updated flooring, fresh interior paint, double-pane windows, blown attic insulation, all-new ductwork, updated plumbing, a new electrical breaker panel, and complete home rewiring. Crown molding, recessed lighting, six-inch baseboards, and French doors add style and functionality throughout the home. The primary suite features French doors to the patio, a walk-in closet, dressing area, and a beautifully renovated bath with dual vanities, walk-in shower, travertine finishes, and updated fixtures. The secondary bathroom has also been fully remodeled with marble finishes, dual vanities, a new tub, and updated lighting. Outdoor highlights include a large rear deck, brick patio area, irrigation well and sprinkler system, and a fully fenced backyard with separate sections—ideal for pets, play, and entertaining. The perimeter fence was replaced and stained in 2017. Move-in ready and thoughtfully updated throughout, this exceptional home combines classic character, quality improvements, and an unbeatable location close to top-rated schools, parks, shopping, and dining.

2080 Goldwater Court, Maitland

Listing courtesy of REAL BROKER, LLC. 855-450-0442

$585,000

Welcome home to a rare find, one of the largest floor plans in the community, sitting right on Lake Charity. This Mediterranean style townhome greets you with sweeping water views, mature landscaping, and a peaceful stillness that is hard to find this close to everything. Inside, wood floors and tile carry you through the first level. Plantation shutters run throughout the home and you'll find real wood cabinetry, a detail that speaks to the quality of this build. A large family room and dining room combo with a half bath offers plenty of space to entertain. The kitchen features newer appliances and granite countertops, opening into a bright and functional living space. The primary suite is located on the first floor and is oversized, with double vanities, a jacuzzi tub plus separate shower, and a walk in closet. Head upstairs to a spacious landing area that connects three additional bedrooms, featuring walk in closets with closet systems, along with two full bathrooms. Step outside to the true showstopper. Townhomes rarely feel private, but this courtyard is your own Mediterranean oasis. Grow plants, entertain, or simply enjoy the quiet. Another great feature of this home is the all new energy efficient windows and new AC unit, keeping utilities low without sacrificing comfort. Walk through the covered entry to your oversized two car garage, a rare find, offering plenty of room for both vehicles plus storage. As a resident, you'll enjoy a resort style community pool overlooking Lake Charity, all within a gated neighborhood. Minutes from Maitland Boulevard and I4, you're close to Downtown Orlando, Maitland, and Park Avenue. If you're looking to be in the heart of Maitland with the space, privacy and lake views to match, this is the home for you.

4 Beds ⋅ 4 Baths ⋅ O6424632 MLS ⋅ 1132 BLDG.

Welcome home to a rare find, one of the largest floor plans in the community, sitting right on Lake Charity. This Mediterranean style townhome greets you with sweeping water views, mature landscaping, and a peaceful stillness that is hard to find this close to everything. Inside, wood floors and tile carry you through the first level. Plantation shutters run throughout the home and you'll find real wood cabinetry, a detail that speaks to the quality of this build. A large family room and dining room combo with a half bath offers plenty of space to entertain. The kitchen features newer appliances and granite countertops, opening into a bright and functional living space. The primary suite is located on the first floor and is oversized, with double vanities, a jacuzzi tub plus separate shower, and a walk in closet. Head upstairs to a spacious landing area that connects three additional bedrooms, featuring walk in closets with closet systems, along with two full bathrooms. Step outside to the true showstopper. Townhomes rarely feel private, but this courtyard is your own Mediterranean oasis. Grow plants, entertain, or simply enjoy the quiet. Another great feature of this home is the all new energy efficient windows and new AC unit, keeping utilities low without sacrificing comfort. Walk through the covered entry to your oversized two car garage, a rare find, offering plenty of room for both vehicles plus storage. As a resident, you'll enjoy a resort style community pool overlooking Lake Charity, all within a gated neighborhood. Minutes from Maitland Boulevard and I4, you're close to Downtown Orlando, Maitland, and Park Avenue. If you're looking to be in the heart of Maitland with the space, privacy and lake views to match, this is the home for you.

1132 Charming Street, Maitland

Listing courtesy of ONE LUXURY INTERNATIONAL LLC. 407-312-8003

$979,000

Welcome to Hidden Estates, where luxury, space, and flexibility come together in one of Maitland's most sought-after neighborhoods. Nestled on a quiet cul-de-sac, this rare single-story custom residence offers over 4,000 square feet of thoughtfully designed living space on an expansive three-quarter-acre lot. From the moment you arrive, you'll appreciate the impressive curb appeal, oversized driveway, and exceptional parking with plenty of room for multiple vehicles, boats, RVs, trailers, and recreational equipment. Inside, the home's spacious open layout is designed for both everyday living and entertaining, featuring soaring ceilings, hardwood flooring, crown molding, skylights, custom built-ins, plantation shutters, and a wood-burning fireplace. At the center of the home is a beautifully appointed chef's kitchen with custom mahogany cabinetry, granite countertops, a Thermador refrigerator, six-burner gas cooktop, double ovens, an oversized island with bar seating, and a generous walk-in pantry. The luxurious primary suite serves as a private retreat with its own sitting area, walk-in closet, heated bathroom floors, dual vanities, oversized walk-in shower, and freestanding soaking tub. One of the home's most unique features is its flexible layout, including a private guest suite situated on the opposite side of the home and a separate office overlooking a tranquil atrium, offering endless possibilities for guests, multigenerational living, a home office, or creative space. Step outside to your own private backyard oasis featuring a screened saltwater pool and spa with waterfall, an expansive covered lanai, and abundant outdoor living space designed for year-round Florida enjoyment. The oversized lot provides exceptional privacy while offering ample room to relax, entertain, or personalize the outdoor space. Additional highlights include a metal roof with copper fascia (2018), new septic drain field, and an unbeatable Maitland location convenient to shopping, dining, parks, major roadways, and everyday conveniences. This is a rare opportunity to experience the space, privacy, and versatility that define luxury living in Maitland.

4 Beds ⋅ 4 Baths ⋅ O6422450 MLS

Welcome to Hidden Estates, where luxury, space, and flexibility come together in one of Maitland's most sought-after neighborhoods. Nestled on a quiet cul-de-sac, this rare single-story custom residence offers over 4,000 square feet of thoughtfully designed living space on an expansive three-quarter-acre lot. From the moment you arrive, you'll appreciate the impressive curb appeal, oversized driveway, and exceptional parking with plenty of room for multiple vehicles, boats, RVs, trailers, and recreational equipment. Inside, the home's spacious open layout is designed for both everyday living and entertaining, featuring soaring ceilings, hardwood flooring, crown molding, skylights, custom built-ins, plantation shutters, and a wood-burning fireplace. At the center of the home is a beautifully appointed chef's kitchen with custom mahogany cabinetry, granite countertops, a Thermador refrigerator, six-burner gas cooktop, double ovens, an oversized island with bar seating, and a generous walk-in pantry. The luxurious primary suite serves as a private retreat with its own sitting area, walk-in closet, heated bathroom floors, dual vanities, oversized walk-in shower, and freestanding soaking tub. One of the home's most unique features is its flexible layout, including a private guest suite situated on the opposite side of the home and a separate office overlooking a tranquil atrium, offering endless possibilities for guests, multigenerational living, a home office, or creative space. Step outside to your own private backyard oasis featuring a screened saltwater pool and spa with waterfall, an expansive covered lanai, and abundant outdoor living space designed for year-round Florida enjoyment. The oversized lot provides exceptional privacy while offering ample room to relax, entertain, or personalize the outdoor space. Additional highlights include a metal roof with copper fascia (2018), new septic drain field, and an unbeatable Maitland location convenient to shopping, dining, parks, major roadways, and everyday conveniences. This is a rare opportunity to experience the space, privacy, and versatility that define luxury living in Maitland.

229 Flame Avenue, Maitland

Listing courtesy of BHHS FLORIDA REALTY. 407-406-5300

$595,000

Welcome to 741 Brookside Road in the heart of Maitland! This beautifully updated 4-bedroom, 2-bath pool home offers the perfect blend of modern upgrades, spacious living, and an unbeatable location. No expense was spared during the home's extensive renovations, creating a truly move-in-ready property that combines quality craftsmanship with timeless style. The recently remodeled kitchen is a true showpiece, featuring solid wood cabinetry, elegant Taj Majal granite countertops, upgraded appliances, and abundant workspace for cooking and entertaining. Recent improvements throughout the home include fresh interior paint, a newly renovated guest bathroom, updated plumbing, and a new roof installed in 2024, providing peace of mind for years to come. At the heart of the home is an enormous Florida Room, offering exceptional space for gathering with family and friends while overlooking the tropical backyard retreat. Step outside to your private oasis, complete with a sparkling pool and fountain surrounded by lush landscaping that creates a serene, resort-style atmosphere. Situated on a large fenced corner lot with no HOA, this property offers both privacy and freedom. Its fantastic Maitland location places you just minutes from shopping, dining, parks, and major roadways, making everyday living both convenient and enjoyable. You will be hard-pressed to find another property in this location and price range that offers this level of attention to detail, quality of construction, and thoughtful upgrades throughout. Every improvement has been carefully selected to create a home that is as functional as it is beautiful. Move-in ready and loaded with updates, this rare opportunity combines comfort, style, and outdoor living in one exceptional package. Schedule your private showing today and discover everything this beautiful Maitland home has to offer! Square footage includes Florida Room of 336 square feet not included on tax records.

4 Beds ⋅ 2 Baths ⋅ S5152100 MLS

Welcome to 741 Brookside Road in the heart of Maitland! This beautifully updated 4-bedroom, 2-bath pool home offers the perfect blend of modern upgrades, spacious living, and an unbeatable location. No expense was spared during the home's extensive renovations, creating a truly move-in-ready property that combines quality craftsmanship with timeless style. The recently remodeled kitchen is a true showpiece, featuring solid wood cabinetry, elegant Taj Majal granite countertops, upgraded appliances, and abundant workspace for cooking and entertaining. Recent improvements throughout the home include fresh interior paint, a newly renovated guest bathroom, updated plumbing, and a new roof installed in 2024, providing peace of mind for years to come. At the heart of the home is an enormous Florida Room, offering exceptional space for gathering with family and friends while overlooking the tropical backyard retreat. Step outside to your private oasis, complete with a sparkling pool and fountain surrounded by lush landscaping that creates a serene, resort-style atmosphere. Situated on a large fenced corner lot with no HOA, this property offers both privacy and freedom. Its fantastic Maitland location places you just minutes from shopping, dining, parks, and major roadways, making everyday living both convenient and enjoyable. You will be hard-pressed to find another property in this location and price range that offers this level of attention to detail, quality of construction, and thoughtful upgrades throughout. Every improvement has been carefully selected to create a home that is as functional as it is beautiful. Move-in ready and loaded with updates, this rare opportunity combines comfort, style, and outdoor living in one exceptional package. Schedule your private showing today and discover everything this beautiful Maitland home has to offer! Square footage includes Florida Room of 336 square feet not included on tax records.

741 Brookside Road, Maitland

Listing courtesy of TRANSCEND REALTY. 407-518-7653

$184,900

If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.

2 Beds ⋅ 2 Baths ⋅ O6416664 MLS ⋅ 08 BLDG.

If you are looking for a terrific property, look no further! You or your tenant can live the lifestyle deserved in this RESORT-STYLE, video-monitored GATED COMMUNITY located on beautiful Lake Shadow in the heart of Maitland Center. This two-bed/two-bath, 2nd-story, CORNER UNIT features an OPEN floor plan with a LIVING/DINING COMBO and 9-FOOT CEILINGS. The KITCHEN includes a breakfast bar, closet pantry, INSIDE UTILITY CLOSET with washer and dryer, and neutral tile. All appliances convey at closing. DOUBLE MASTERS each offer an en-suite bath and a walk-in closet. The 20 X 20 living area provides lots of sunlight and features a built-in nook with glass shelving you can use as you choose. In 2024, the interior was painted, and carpet was installed. Through sliders, you can unwind at the end of a busy day on the SCREEN-ENCLOSED tiled LANAI and enjoy a TRUE ESCAPE. If extra storage is needed, a patio closet awaits! This GORGEOUSLY LANDSCAPED and PET-FRIENDLY community offers two LAKESIDE POOLS with Wi-Fi access, a club-quality FITNESS CENTER, grand CLUB ROOM with CATERING KITCHEN, fully-equipped BUSINESS CENTER, lighted TENNIS courts, BASKETBALL court, car wash area, two laundry facilities, 24-HOUR MAINTENANCE, WATER, SEWER, and a Monday-Friday VALET WASTE REMOVAL SERVICE. The condo community boasts a newer tile roof, reflecting ongoing care and investment in the property. Located minutes away from SR 414, I-4, 429, Routes 434 and 436; it is a quick drive to downtown Orlando, Cranes Roost Park, and to the upscale shopping and dining at Altamonte Mall, Altamonte Towne Center, Winter Park Village, and Winter Park’s quaint Park Avenue. Enjoy Florida living at its best! This property may be under audio & visual surveillance.

1440 Lake Shadow Circle Unit 8201, Maitland

Listing courtesy of COLDWELL BANKER REALTY. 407-333-8088

$1,499,000

A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.

5 Beds ⋅ 4 Baths ⋅ O6415928 MLS

A premier street offering an accessible lifestyle to Maitland’s vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland’s special neighborhoods.

255 W George Avenue, Maitland

Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY. 407-644-3295

$1,995,000

Welcome to 220 Adams Drive — a breathtaking, completely remodeled single-story masterpiece nestled in the heart of Maitland's coveted Kings Row neighborhood. Thoughtfully reimagined from the studs out with exquisite craftsmanship and elevated design, this stunning home offers 4 bedrooms, a dedicated private office, 3.5 baths, and over 3,000 square feet of refined living on a fully fenced, oversized lot. The renovation is truly comprehensive — all-new plumbing, electrical, ductwork, and three separate AC units provide complete peace of mind. Spray foam insulation delivers exceptional energy efficiency, propane gas powers the chef's kitchen cooktop and tankless hot water heater, and Lutron touch-slide dimmers indoors plus automated Lutron outdoor lighting give the home a level of sophistication and control that is rarely found at any price. French drains round out a property that has been engineered as thoughtfully as it has been finished. Step through a charming covered front porch and into a bright, open-concept interior where elevated ceilings, rich wood floors, and designer recessed lighting create an effortlessly elegant atmosphere. The chef's kitchen is a showstopper — outfitted with high-end appliances including a gas cooktop, custom white cabinetry, clever appliance garages, and bespoke built-ins that marry beauty with function. The warm and inviting living room anchors the home with a wood-burning fireplace and seamless sliding doors to the pool beyond. The split-bedroom layout offers exceptional privacy for every member of the household. The oversized primary suite features a spa-inspired en suite with a double-sink vanity, walk-in glass shower, and soaking tub — plus a large walk-in closet with custom built-ins. The second bedroom enjoys its own private en suite with a walk-in shower, perfect for guests or multi-generational living. Bedrooms three and four share a well-appointed hall bath with a tub/shower combination. Outside, your private resort awaits. The saltwater pool with sunshelf is the perfect centerpiece, framed by a covered cabana with fireplace and a fully equipped outdoor kitchen. The Lutron automated lighting system extends seamlessly to the exterior, creating effortless ambiance day and night. The fully fenced yard offers privacy and room to breathe. The property features a two-car garage and a separate one-car garage — both finished with epoxy floors. The one-car garage is currently appointed as a private home gym with an adjacent storage room, offering flexible utility from day one. Located in a quiet, tucked-away neighborhood with a community park and playground, this home is just minutes from Winter Park, Park Avenue, the Winter Park Racquet Club, and scenic parks and trails. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High School. Homes of this caliber — fully rebuilt, impeccably finished, with every system new — are extraordinarily rare. Schedule your private showing today.

4 Beds ⋅ 4 Baths ⋅ O6413737 MLS

Welcome to 220 Adams Drive — a breathtaking, completely remodeled single-story masterpiece nestled in the heart of Maitland's coveted Kings Row neighborhood. Thoughtfully reimagined from the studs out with exquisite craftsmanship and elevated design, this stunning home offers 4 bedrooms, a dedicated private office, 3.5 baths, and over 3,000 square feet of refined living on a fully fenced, oversized lot. The renovation is truly comprehensive — all-new plumbing, electrical, ductwork, and three separate AC units provide complete peace of mind. Spray foam insulation delivers exceptional energy efficiency, propane gas powers the chef's kitchen cooktop and tankless hot water heater, and Lutron touch-slide dimmers indoors plus automated Lutron outdoor lighting give the home a level of sophistication and control that is rarely found at any price. French drains round out a property that has been engineered as thoughtfully as it has been finished. Step through a charming covered front porch and into a bright, open-concept interior where elevated ceilings, rich wood floors, and designer recessed lighting create an effortlessly elegant atmosphere. The chef's kitchen is a showstopper — outfitted with high-end appliances including a gas cooktop, custom white cabinetry, clever appliance garages, and bespoke built-ins that marry beauty with function. The warm and inviting living room anchors the home with a wood-burning fireplace and seamless sliding doors to the pool beyond. The split-bedroom layout offers exceptional privacy for every member of the household. The oversized primary suite features a spa-inspired en suite with a double-sink vanity, walk-in glass shower, and soaking tub — plus a large walk-in closet with custom built-ins. The second bedroom enjoys its own private en suite with a walk-in shower, perfect for guests or multi-generational living. Bedrooms three and four share a well-appointed hall bath with a tub/shower combination. Outside, your private resort awaits. The saltwater pool with sunshelf is the perfect centerpiece, framed by a covered cabana with fireplace and a fully equipped outdoor kitchen. The Lutron automated lighting system extends seamlessly to the exterior, creating effortless ambiance day and night. The fully fenced yard offers privacy and room to breathe. The property features a two-car garage and a separate one-car garage — both finished with epoxy floors. The one-car garage is currently appointed as a private home gym with an adjacent storage room, offering flexible utility from day one. Located in a quiet, tucked-away neighborhood with a community park and playground, this home is just minutes from Winter Park, Park Avenue, the Winter Park Racquet Club, and scenic parks and trails. Zoned for top-rated Dommerich Elementary, Maitland Middle, and Winter Park High School. Homes of this caliber — fully rebuilt, impeccably finished, with every system new — are extraordinarily rare. Schedule your private showing today.

220 Adams Drive, Maitland

Listing courtesy of KELLY PRICE & COMPANY LLC. 407-645-4321

$2,999,000

Welcome to luxury lakefront living at its absolute finest in the heart of Maitland, Florida. Nestled along the pristine shores of Lake Sybelia, this extraordinary three-story estate offers an unparalleled combination of elegance, comfort, and breathtaking waterfront views. Boasting 5,355 square feet of thoughtfully designed living space, this stunning residence features six spacious bedrooms, four and a half bathrooms, and an open-concept floor plan perfectly crafted for both entertaining and everyday living. Expansive walls of glass fill the home with natural light while showcasing panoramic lake views from nearly every room. The main living area seamlessly connects the gourmet kitchen, dining room, living room, and family room, all overlooking the sparkling waters of skiable Lake Sybelia. Designed with indoor-outdoor living in mind, each floor features a balcony spanning the entire width of the rear of the home, creating multiple spaces to relax and enjoy Florida’s spectacular sunsets. Step outside to your private resort-style oasis complete with a gorgeous pool, lush landscaping, and direct lake access with your own private boat dock and lift, perfect for boating, skiing, and waterfront recreation year-round. The upstairs retreat is anchored by an impressive primary suite featuring serene lake views and private balcony access. The upper level also includes a dedicated private office, ideal for working from home while enjoying stunning lakefront views. Two additional bedrooms share a beautifully designed Jack-and-Jill bathroom, while another flexible bedroom space can easily serve as a nursery, fitness room, or additional guest bedroom. Every level of the home has been carefully designed to maximize comfort, privacy, and functionality while maintaining a sophisticated and timeless aesthetic throughout. The lower level offers endless entertainment possibilities with a spacious game room, a full movie theatre, an additional guest bedroom, and a full bathroom ideal for visitors or multi-generational living. Completing this exceptional property is a beautiful temperature controlled wine cellar holding almost 2,000 wine bottles, a two-car garage with additional storage space, a large home generator, and countless luxury details throughout. This one-of-a-kind Lake Sybelia estate delivers the perfect balance of upscale living, modern convenience, and the ultimate waterfront lifestyle in one of Central Florida’s most desirable locations.

6 Beds ⋅ 5 Baths ⋅ O6411525 MLS

Welcome to luxury lakefront living at its absolute finest in the heart of Maitland, Florida. Nestled along the pristine shores of Lake Sybelia, this extraordinary three-story estate offers an unparalleled combination of elegance, comfort, and breathtaking waterfront views. Boasting 5,355 square feet of thoughtfully designed living space, this stunning residence features six spacious bedrooms, four and a half bathrooms, and an open-concept floor plan perfectly crafted for both entertaining and everyday living. Expansive walls of glass fill the home with natural light while showcasing panoramic lake views from nearly every room. The main living area seamlessly connects the gourmet kitchen, dining room, living room, and family room, all overlooking the sparkling waters of skiable Lake Sybelia. Designed with indoor-outdoor living in mind, each floor features a balcony spanning the entire width of the rear of the home, creating multiple spaces to relax and enjoy Florida’s spectacular sunsets. Step outside to your private resort-style oasis complete with a gorgeous pool, lush landscaping, and direct lake access with your own private boat dock and lift, perfect for boating, skiing, and waterfront recreation year-round. The upstairs retreat is anchored by an impressive primary suite featuring serene lake views and private balcony access. The upper level also includes a dedicated private office, ideal for working from home while enjoying stunning lakefront views. Two additional bedrooms share a beautifully designed Jack-and-Jill bathroom, while another flexible bedroom space can easily serve as a nursery, fitness room, or additional guest bedroom. Every level of the home has been carefully designed to maximize comfort, privacy, and functionality while maintaining a sophisticated and timeless aesthetic throughout. The lower level offers endless entertainment possibilities with a spacious game room, a full movie theatre, an additional guest bedroom, and a full bathroom ideal for visitors or multi-generational living. Completing this exceptional property is a beautiful temperature controlled wine cellar holding almost 2,000 wine bottles, a two-car garage with additional storage space, a large home generator, and countless luxury details throughout. This one-of-a-kind Lake Sybelia estate delivers the perfect balance of upscale living, modern convenience, and the ultimate waterfront lifestyle in one of Central Florida’s most desirable locations.

1166 N Lake Sybelia, Maitland

Listing courtesy of KELLER WILLIAMS WINTER PARK. 407-545-6430

$467,000

Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

2 Beds ⋅ 2 Baths ⋅ O6394791 MLS ⋅ 204 BLDG.

Updated 2 bedroom 2 bathroom located on the second floor of sought after Moorings Lakefront Community with spectacular views of Lake Maitland of the Winter Park Chain of Lakes. The condo offers a large screened-in balcony overlooking Lake Maitland. The open floorpan offers a split plan with a generous size master retreat with a private door to the balcony and a secondary ensuite. The updated spacious kitchen features stainless steel appliances and a breakfast nook situated in a bay window. The dining living room combo is very spacious making it perfect for relaxing or entertaining. The condo offers washer and dryer in the unit as well as a private storage closet on the same floor just across the hall. The Moorings Lakefront community offers an amazing recently updated pool and spa area along a large clubhouse. Whether you're looking for a primary residence or a low-maintenance lakefront retreat, this condo and community offers an amazing combination of comfort and convenience.

204 Quayside Circle Unit 201, Maitland

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211

$519,999

Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining, and living areas connect seamlessly, creating a comfortable and functional main living space. Upstairs, generously sized bedrooms offer flexibility for families, guests, or home office needs, while the overall layout supports a wide range of lifestyles. Located in highly desirable Maitland, the home offers convenient access to shopping, dining, major roadways, and all Central Florida amenities. Private showings available upon request.they’ve been waiting for.

4 Beds ⋅ 3 Baths ⋅ G5110747 MLS

Welcome to 1776 Bobtail Drive, a home that offers an easy, natural flow and a layout designed for everyday living. This property is now being reintroduced with a refreshed presentation and a full 3D walkthrough experience, giving buyers the ability to explore every space at their own pace before stepping inside in person. Inside, the home features an open-concept layout where the kitchen, dining, and living areas connect seamlessly, creating a comfortable and functional main living space. Upstairs, generously sized bedrooms offer flexibility for families, guests, or home office needs, while the overall layout supports a wide range of lifestyles. Located in highly desirable Maitland, the home offers convenient access to shopping, dining, major roadways, and all Central Florida amenities. Private showings available upon request.they’ve been waiting for.

1776 Bobtail Drive, Maitland

Listing courtesy of THE FLORIDA PROPERTY SHOP SALE. 352-346-7857

$299,000

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

2 Beds ⋅ 2 Baths ⋅ O6395472 MLS ⋅ 12 BLDG.

Elegantly renovated two-bedroom, two-bath second-floor condo in the gated community of Sun Bay Club on Lake Destiny in Maitland. Vaulted ceilings and abundant windows create a bright, airy atmosphere throughout. The gourmet kitchen has been fully updated with 42-inch custom hardwood cabinets, Zodiaq (Cambrian) quartz countertops, a Kohler farmhouse sink, stainless steel appliances, and porcelain wood-plank floors. The kitchen opens to the dining and living areas, featuring a built-in desk, wood-burning fireplace, custom built-ins, clerestory windows, and triple sliding doors leading to a private balcony with a storage closet. The split floorplan includes the primary suite with a walk-in closet and a renovated bath with dual vanities, hardwood cabinets, designer fixtures, a glass-block shower, and natural light from a private skylight. The secondary bedroom has two wall closets and an upgraded bathroom with custom cabinets, a tub, and a skylight. Meticulously maintained with pride of ownership reflected throughout. Features include double-door entry, knockdown ceilings, designer finishes, ample storage, and an interior laundry closet. Additional updates include a new Carrier AC (2023), a new hot water heater (2025), and a new tile roof with gutters, downspouts, and skylights (2024). Sun Bay Club offers a beautiful lakefront pool, lake access with a boat ramp, a tennis court, a dog park, a community meeting room, and a car wash area for residents. Its central location is just minutes from I-4, RDV Sportsplex, Publix, shopping, and dining. Downtown Maitland, Winter Park, and Orlando are only a short drive away.

1000 Winderley Place Unit 239, Maitland

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234

$824,900

Welcome to Dommerich Hills, where modern style meets everyday comfort. This beautifully renovated home offers the freedom of **NO HOA** and has been thoughtfully updated from top to bottom. From the paver driveway and elegant double-door entry to the bright, open-concept interior, every detail has been designed to make you feel at home. The heart of the home is a stunning chef-inspired kitchen featuring sleek custom cabinetry, stainless steel appliances, and a striking waterfall island with custom wood accents,perfect for entertaining family and friends. The spa like bathrooms has glass-enclosed showers, contemporary fixtures, and designer finishes that create a relaxing retreat. Step outside and discover your own private Florida oasis. A covered lanai overlooks the sparkling pool and expansive paver patio, creating the ideal space for outdoor dining, weekend gatherings, or simply unwinding in the sunshine. Conveniently located just minutes from major highways, shopping, dining, and entertainment, this beautifully renovated home combines modern design with everyday functionality. Schedule your private showing today and experience everything this exceptional property.

5 Beds ⋅ 3 Baths ⋅ S5146322 MLS

Welcome to Dommerich Hills, where modern style meets everyday comfort. This beautifully renovated home offers the freedom of **NO HOA** and has been thoughtfully updated from top to bottom. From the paver driveway and elegant double-door entry to the bright, open-concept interior, every detail has been designed to make you feel at home. The heart of the home is a stunning chef-inspired kitchen featuring sleek custom cabinetry, stainless steel appliances, and a striking waterfall island with custom wood accents,perfect for entertaining family and friends. The spa like bathrooms has glass-enclosed showers, contemporary fixtures, and designer finishes that create a relaxing retreat. Step outside and discover your own private Florida oasis. A covered lanai overlooks the sparkling pool and expansive paver patio, creating the ideal space for outdoor dining, weekend gatherings, or simply unwinding in the sunshine. Conveniently located just minutes from major highways, shopping, dining, and entertainment, this beautifully renovated home combines modern design with everyday functionality. Schedule your private showing today and experience everything this exceptional property.

2801 Waumpi Trail, Maitland

Listing courtesy of AVANTI WAY REALTY LLC. 305-229-1146

$4,999,000

Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.

5 Beds ⋅ 8 Baths ⋅ O6362152 MLS

Pre-Construction. To be built. An extraordinary opportunity to claim one of Lake Seminary’s desired shorelines awaits. Masterfully envisioned by Heathrow Custom Homes, this newly built lakefront estate introduces a fresh standard of modern luxury for Maitland and Winter Park. Poised on an expansive 0.69-acre parcel, the residence spans nearly 6,500 square feet of impeccably curated living space, where sophisticated architecture and bespoke finishes harmonize with the tranquil beauty of the lake. A striking floating staircase framed by floor-to-ceiling glass offers a captivating first impression, while the grand entry reveals uninterrupted vistas of the pool terrace and shimmering water beyond. The chef’s kitchen, anchored by a remarkable 20-foot island, features premier appliances, exceptional storage and a concealed full-service scullery, creating an environment for hosting with grace and ease. The great room continues the home’s celebration of light and space with walls of glass that welcome breathtaking lake views at every turn. The primary suite is a serene retreat, showcasing a spa-inspired bath with floating vanities, a freestanding soaking tub, an expansive glass-enclosed shower and extravagant walk-in closets designed for the discerning owner. A secondary bedroom suite and oversized laundry enrich the main level, while an expansive lanai with an extraordinary summer kitchen invites effortless alfresco living, an experience only genuine lakefront living can provide. The second floor unfolds into a generous game room, complete with a wet bar and kitchenette. Three beautifully appointed bedroom suites, two scenic balconies, and a purpose-built home theater create an environment tailor-made for indulgence and entertainment. A new boathouse, soon to be constructed, further elevates the lakefront lifestyle. With three garages, a contemporary parking court, and meticulously executed architectural detail, this residence embodies modern luxury at its most refined. Lake Seminary, home to just 35 exclusive residences, offers coveted privacy while remaining moments from boutique shopping, celebrated dining and best of Winter Park. Immediate access to Interstate 4 and surrounding beltways ensures effortless connectivity throughout Central Florida.

360 Lake Seminary Circle, Maitland

Listing courtesy of PREMIER SOTHEBYS INT'L REALTY. 407-333-1900

$385,900

Back on the market with renewed momentum. Nestled in one of Maitland's most sought-after neighborhoods, this fully renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and timeless charm, ideal for families ready to make new memories. From the moment you step inside, you're greeted by an abundance of natural light and an open, airy layout that instantly feels like home. The heart of the house, the newly renovated kitchen features sleek stone countertops and new appliances, making it perfect for family meals and holiday gatherings. Step outside to the screened-in patio and picture slow mornings with coffee in hand, or peaceful evenings unwinding from a long day in the spacious backyard. Whether hosting a barbecue or enjoying a quiet night under the stars, this outdoor space is made for relaxation! Located just minutes from top-rated schools, grocery stores, dining, and major highways and less than 10 miles from the natural beauty of Wekiwa Springs State Park. This home offers the convenience you need and the lifestyle you've been dreaming of. Don't miss this opportunity to plant roots and grow in a home that has it all. Schedule your private tour today and discover the warmth, space, and charm waiting for your family.

3 Beds ⋅ 2 Baths ⋅ O6324872 MLS

Back on the market with renewed momentum. Nestled in one of Maitland's most sought-after neighborhoods, this fully renovated 3-bedroom, 2-bathroom home offers the perfect blend of modern comfort and timeless charm, ideal for families ready to make new memories. From the moment you step inside, you're greeted by an abundance of natural light and an open, airy layout that instantly feels like home. The heart of the house, the newly renovated kitchen features sleek stone countertops and new appliances, making it perfect for family meals and holiday gatherings. Step outside to the screened-in patio and picture slow mornings with coffee in hand, or peaceful evenings unwinding from a long day in the spacious backyard. Whether hosting a barbecue or enjoying a quiet night under the stars, this outdoor space is made for relaxation! Located just minutes from top-rated schools, grocery stores, dining, and major highways and less than 10 miles from the natural beauty of Wekiwa Springs State Park. This home offers the convenience you need and the lifestyle you've been dreaming of. Don't miss this opportunity to plant roots and grow in a home that has it all. Schedule your private tour today and discover the warmth, space, and charm waiting for your family.

601 Oranole Road, Maitland

Listing courtesy of COLDWELL BANKER RESIDENTIAL RE. 407-647-1211

$1,395,500

$50,000 BUYER FLEX MONEY! SELLER IS OFFERING $50,000 TOWARDS AN INTEREST-RATE BUY DOWN, CLOSING COSTS OR PRE PAIDS EXPENSES! A substantial opportunity to reduce cash needed at closing and/or potentially lower your monthly payment! ASK FOR DETAILS. Exceptional value meets timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five spacious bedrooms, four and a half baths, and a three car garage, complemented by soaring ceilings, refined architectural details, and a thoughtfully designed open layout. The gourmet kitchen features solid wood cabinetry, a large island, newer refrigerator, walk in pantry, and dual breakfast bars that seamlessly connect to the formal dining and family rooms, where a cozy gas fireplace and a bar with sink and ice icemaker, create an inviting setting for everyday living and entertaining. Designed with flexibility in mind, this home effortlessly adapts to your family’s needs, ideal for traditional living, multigenerational arrangements, a private guest retreat, or a dedicated work from home environment with two wings on the first level. Upstairs, the spacious owner’s retreat provides a peaceful escape with a loft style office and sitting area, dual walk in closets, and a spa inspired bath. Outdoors, enjoy a lush tropical setting featuring a saltwater pool with new equipment and has a new sparkling finish, along with papaya trees and blooming amaryllis that create a serene, resort-style atmosphere. Additional highlights include a new roof (2023), first floor laundry with newer appliances, tray ceilings, elegant archways, all just minutes from top rated schools, parks, dining, shopping, Winter Park’s Park Avenue and the Winter Park Village as well as many local favorites, offering the perfect combination of privacy, convenience. A great canvas with many possibilities to create a space that truly reflects your modern vision and lifestyle. Enjoy scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum in one of Central Florida’s most sought after communities. Schedule your private showing today and experience the extraordinary lifestyle this Maitland home provides.

5 Beds ⋅ 5 Baths ⋅ O6299581 MLS

$50,000 BUYER FLEX MONEY! SELLER IS OFFERING $50,000 TOWARDS AN INTEREST-RATE BUY DOWN, CLOSING COSTS OR PRE PAIDS EXPENSES! A substantial opportunity to reduce cash needed at closing and/or potentially lower your monthly payment! ASK FOR DETAILS. Exceptional value meets timeless elegance in this incredible home nestled in the heart of Maitland, privately situated on a cul de sac within an exclusive gated enclave of custom residences. Perfectly positioned between Lake Sybelia and Lake Catherine, this one owner estate offers a rare blend of sophistication, comfort, and versatility with five spacious bedrooms, four and a half baths, and a three car garage, complemented by soaring ceilings, refined architectural details, and a thoughtfully designed open layout. The gourmet kitchen features solid wood cabinetry, a large island, newer refrigerator, walk in pantry, and dual breakfast bars that seamlessly connect to the formal dining and family rooms, where a cozy gas fireplace and a bar with sink and ice icemaker, create an inviting setting for everyday living and entertaining. Designed with flexibility in mind, this home effortlessly adapts to your family’s needs, ideal for traditional living, multigenerational arrangements, a private guest retreat, or a dedicated work from home environment with two wings on the first level. Upstairs, the spacious owner’s retreat provides a peaceful escape with a loft style office and sitting area, dual walk in closets, and a spa inspired bath. Outdoors, enjoy a lush tropical setting featuring a saltwater pool with new equipment and has a new sparkling finish, along with papaya trees and blooming amaryllis that create a serene, resort-style atmosphere. Additional highlights include a new roof (2023), first floor laundry with newer appliances, tray ceilings, elegant archways, all just minutes from top rated schools, parks, dining, shopping, Winter Park’s Park Avenue and the Winter Park Village as well as many local favorites, offering the perfect combination of privacy, convenience. A great canvas with many possibilities to create a space that truly reflects your modern vision and lifestyle. Enjoy scenic walkability or a bike ride along Lake Sybelia to local cafés, the Sunday Farmers Market, and the Maitland Art Museum in one of Central Florida’s most sought after communities. Schedule your private showing today and experience the extraordinary lifestyle this Maitland home provides.

755 Cranes Court, Maitland

Listing courtesy of PREMIER SOTHEBY'S INTL. REALTY. 407-644-3295