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$415,000
3 Beds ⋅ 3 Baths ⋅ O6439283 MLS ⋅ 1257 BLDG.
Welcome to beautiful Montacino, Enclave at Maitland, a well maintained Mediterranean inspired gated community. This well appointed town home features three bedrooms and two and 1/2 bathrooms. The first floor is a desirable open floor plan with a welcoming foyer, 1/2 bathroom, fully tiled living/dining room, kitchen with bar top and access to the first floor covered patio. The kitchen has beautiful rich cabinetry, dark granite countertops with newer stainless steel appliances as well as pantry for additional storage space. The second floor features all three bedrooms, two bathrooms and ideally located central laundry closet with 2 year old (high capacity) washer and dryer included. The primary bedroom features a private ensuite bathroom with an updated double vanity, gorgeous walk-in shower with rain shower option, a walk in closet with built-in storage cabinets and a private balcony overlooking community green space. The flooring on the second floor is luxury vinyl plank in the bedrooms and hallway and tile in the bathrooms. (carpet only on stairwell). The interior was just freshly painted and new fans were added in the living room and primary bedroom, allowing for a turnkey move-in ready experience. Additionally there are high end plantation shutters throughout! There is an attached one car garage and private paver driveway as well as open community parking. Montacino features a resort style community pool and beautiful sidewalks overlooking Lake Charity perfect for an evening stroll. All this with exceptionally easy access to I-4 and Maitland Blvd allow for convenient shopping and dining and commuting. Schedule a tour today!

1257 Blessing Street, Maitland

Listing courtesy of EXIT REAL ESTATE RESULTS. 352-933-0018
$130,000
1 Beds ⋅ 1 Baths ⋅ O6437762 MLS ⋅ 2520 BLDG.
**LOCATION, LOCATION!** Welcome to this charming and cozy 1-bedroom, 1-bathroom condo, ideally located in a convenient and desirable area near Semoran Blvd and Howell Branch Rd. This move-in-ready second-floor unit offers comfort, convenience, and easy access to everything you need. Enjoy being just walking distance from shopping, restaurants, supermarkets, and everyday essentials. The community offers a refreshing swimming pool, perfect for relaxing or enjoying quality time with family and friends, as well as ample parking for residents and guests. The property is also conveniently located near schools and educational institutions, including Rollins College, making it an excellent opportunity for professionals, or anyone looking for a convenient Central Florida location. HOA includes water, adding even more value and convenience. Whether you're looking for your next home, a low-maintenance place to live, or an investment opportunity, this condo is one you won't want to miss! Schedule your showing today and come see all this property has to provide.

2520 Caper Lane Unit 204, Maitland

Listing courtesy of AXEN REALTY, LLC. 818-932-8800
$200,000
2 Beds ⋅ 2 Baths ⋅ OM731401 MLS ⋅ Visconti East Condo BLDG.
Welcome to 2637 Legacy Villas Drive, a spacious 2-bedroom, 2-bath residence located in the gated Visconti community in Maitland. Offering 1,280 square feet of living space, this home features a comfortable and functional floor plan along with the added convenience of a private 2-car garage. Enjoy everything the Visconti community has to give, including a resort-style swimming pool, clubhouse, fitness center, tennis courts, basketball courts, playground, and gated entry. The community's recreational spaces and amenities provide plenty of opportunities to enjoy the Central Florida lifestyle. Conveniently located in Maitland with easy access to I-4 and major roadways, the property offers a short commute to Downtown Orlando and convenient access to shopping, dining, entertainment, and employment centers throughout the Orlando area. Whether you're looking for a primary residence or an investment opportunity, this 2-bedroom, 2-bath home combines generous living space, a private 2-car garage, desirable community amenities, and a convenient Maitland location.

2637 Legacy Villas Drive Unit 2637, Maitland

Listing courtesy of EXP REALTY SOUTH LLC. 888-883-8509
$229,000
2 Beds ⋅ 2 Baths ⋅ O6437665 MLS ⋅ 856 BLDG.
LOCATION LOCATION LOCATION! The Park Lake Townhome Community is Maitland's hidden treasure! Offering for sale this well-maintained townhome with 2 levels of comfortable living, a one-car garage, a nice sized laundry room under air, along with a private screened back patio. As you step inside, look over your shoulder at the community pool that is literally steps from your front door! Once inside you will immediately fall in love with the wood-look easy care tile throughout the first floor. The large living room has the cutest window seat, streaming in tons of natural sunlight, with room for many different seating configurations. A convenient half bath to your left leads you into the kitchen and dining areas of the home. The large open concept kitchen features new appliances and shiny granite countertops with plenty of counterspace for the chef in the family. Off the dining area you'll find a set of sliding glass doors leading out to a private screened-in patio, perfect for morning coffees, grilling or entertaining friends and family. The patio also provides access to the attached one-car garage with garage door opener. This garage leads into the oversized indoor laundry room complete with a washer and dryer and a large storage area. As we head up the stairs, you'll notice the brand-new carpet in a lovely neutral color running on the stair treads and into the first bedroom for comfort and style. The 2nd bedroom features the wood-look flooring for added convenience. Both bedrooms share a well-appointed en-suite bathroom with a newly reglazed tub and shower. Freshly painted inside makes this home truly turn-key. Residents of the Park Lake Townhome Community not only enjoy the sparkling community pool, but your HOA also covers trash collection, exterior maintenance (including the roof!) and lawn care! Low Maintenance Living at it's Best! And have I mentioned this AMAZING LOCATION? This lovely townhome community is less than 1 mile from N Park Avenue and less than 1/2 mile to 17/92 (Orlando Avenue)! The convenience to Maitland City Center, Rollins College, shops, restaurants, and the ease of commuting to work is 2nd to none. Make an appt to see this home, it is a gem and won't last! Note, some photos have been virtually staged for furniture placement.

856 Park Lake Circle Unit 51, Maitland

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
$460,000
3 Beds ⋅ 2 Baths ⋅ S5156417 MLS
Charming 3-bedroom, 2-bath pool home in Maitland with tons of potential! This home is ready for a buyer with the vision to renovate, restore, and make it their own. The property needs substantial TLC throughout, but offers a wonderful opportunity to customize it to your personal style. Features include a private pool, screened patio, spacious yard, and covered parking. Conveniently located near shopping, dining, schools, and major roadways. Property is being sold AS-IS. Seller will not make repairs. Cash or conventional financing only.

315 Lake Seminary Circle, Maitland

Listing courtesy of FLORIDA REALTY INVESTMENTS. 407-207-2220
$360,000
3 Beds ⋅ 2 Baths ⋅ S5156259 MLS
Beautifully updated 3-bedroom, 2-bath home in Maitland, conveniently located approximately 10 minutes from Park Avenue. Major improvements include hurricane-impact windows and a new roof in 2021, an updated kitchen with granite countertops in 2022, new tile flooring in 2023, a new A/C system and ductwork installed in August 2025, and new appliances in 2026. The home features a comfortable open layout, a one-car garage, and a private fenced yard perfect for relaxing or entertaining. Conveniently situated near shopping, dining, major roadways, Maitland, and Winter Park. Move-in ready with many major improvements already completed!

1982 Water Lane, Maitland

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
$825,000
3 Beds ⋅ 3 Baths ⋅ O6437275 MLS
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to this gorgeous, move-in-ready 3-bedroom, 2.5-bath POOL home in the desirable Oakland Shores neighborhood of Maitland! Situated on an oversized, beautifully landscaped lot, this exceptional home welcomes you with mature landscaping, a large circular driveway, and additional side parking ideal for a boat or RV. Inside, you’ll immediately appreciate the light and bright open feel, luxury vinyl flooring, and crown molding throughout the main living areas. The formal living room flows seamlessly into the dining and family rooms, all overlooking the spectacular resort-style pool and backyard. The expansive sparkling pool is surrounded by a custom pavered patio with multiple spaces for lounging, dining, and entertaining, while the generous green space and privacy create your own backyard retreat. The beautifully appointed kitchen features quartz countertops, white shaker cabinetry, stainless steel appliances, a center island with sink, walk-in pantry, and a charming dining nook with custom seating. The spacious primary suite offers direct pool access, a huge walk-in closet with a custom organizing system, and a spa-like ensuite bath complete with dual sinks, vanity, garden tub, and separate glass-enclosed shower. Two generously sized secondary bedrooms share an upgraded full bath, while an additional upgraded half bath provides convenience for guests. A well-designed interior laundry room includes built-in cabinetry and direct access to the yard. One of the home’s most versatile features is the large bonus room, complete with a spacious walk-in, air-conditioned storage room. Whether you envision a home gym, classroom, office, creative space, or potential mother-in-law suite, the possibilities are endless. Recent updates provide additional peace of mind, including a roof and septic system replaced in 2017. The septic was recently cleaned in 2025 with the filter replaced. Additional upgrades include electrical, fencing, water heater, pool pump, interior paint, HVAC, irrigation pump, plumbing, and windows. Oakland Shores offers a wonderful neighborhood setting for walking and includes deeded access to Lake Faith, a non-motorized lake great for paddle boarding and kayaking, with a community access point on Lake Shore Drive. Conveniently located near shopping, dining, major roadways, and the newly planned Maitland Trader Joe’s, this home combines comfort, versatility, privacy, and an ideal Maitland location. With its beautiful pool, oversized lot, extensive updates, and flexible living spaces, this is one you won’t want to miss!

505 Oak Lane, Maitland

Listing courtesy of DALTON WADE INC. 888-668-8283
$699,000
4 Beds ⋅ 3 Baths ⋅ O6437084 MLS
This move-in-ready 4-bedroom, 3-full-bath pool home is located in the beautiful Dommerich Estates! Enjoy a waterfront lifestyle just steps from your front door, with access to a private community boat ramp, fishing pier, picnic tables, built-in grills, social events, and endless sunset views along the shoreline of Lake Minnehaha. Lake Boat access is available to Dommerich Estates residents for just $150 annually. Walk or bike to Dommerich Elementary and Maitland Middle. High school is Winter Park High. Beyond the community amenities, you’ll love exploring the multiple nearby resident parks (Maitland Community Park is just a short walk away from the home) featuring canopied tree-lined walking and biking trails, playgrounds, tennis courts, lush gardens, and so much more. Inside, this spacious home offers a desirable split-bedroom floor plan, with the over-sized private primary suite thoughtfully separated from the three additional bedrooms. Build in surround sound speakers. There is no carpet—the home features beautiful travertine and tile flooring throughout. Step outside to your own private oasis! The huge swimming pool is the centerpiece of the expansive screened-in outdoor living area, complete with an oversized paver lanai—perfect for relaxing, entertaining, and enjoying the Florida lifestyle year-round. Additional features include a 2-car garage and paver driveway. A NEW ROOF is scheduled to be installed in late September/early October. A wonderful opportunity to enjoy the comfort of a move-in-ready home with exceptional community amenities. (Throughout the home are pieces of Stickley furniture that are available for sale)

431 Arapaho Trail, Maitland

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
$175,000
2 Beds ⋅ 2 Baths ⋅ OM730553 MLS ⋅ Visconti West Condo BLDG.
Welcome to 1150 Lake Shadow Circle, Unit 3305, a 2-bedroom, 2-bath condominium located in the gated Visconti community in Maitland. Situated on the third floor, this 1,048-square-foot residence offers a functional floor plan with comfortable living spaces, luxury vinyl flooring, crown molding, ceiling fans, and the convenience of an in-unit washer and dryer. Step outside onto your private balcony or take advantage of the community's extensive amenities. Visconti residents enjoy access to a swimming pool, clubhouse, fitness center, tennis courts, playground, sidewalks, and gated entry. Conveniently located in Maitland with easy access to major roadways, the property is a short commute to Downtown Orlando and close to shopping, dining, entertainment, and everything Central Florida has available. Whether you're looking for a primary residence or an investment opportunity, this 2-bedroom, 2-bath condo combines a convenient location, desirable community amenities, and comfortable Florida living.

1150 Lake Shadow Circle Unit 3305, Maitland

Listing courtesy of EXP REALTY SOUTH LLC. 888-883-8509
$960,000
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
$960,000
O6436414 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 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
$525,000
O6436145 MLS
Unique opportunity in historic Eatonville! Situated on approximately 0.29 acres at the corner of Lemon Street and Moseley Avenue, this distinctive property combines C-3 commercial zoning, two existing structures and frontage along two streets—creating an exciting opportunity for the buyer with vision. One residence is currently tenant occupied, offering an existing improvement while future possibilities are explored. The property encompasses historic Lots 5 and 6 of Calhoun's Subdivision and offers a versatile setting that may appeal to investors, entrepreneurs, developers or owner-users. Imagine the possibilities for this highly visible corner—from a future commercial concept or redevelopment opportunity to a creative use of the existing improvements, subject to Town approval and applicable development requirements. Conveniently located near Maitland, Winter Park and the greater Orlando area. Property is currently improved with residential structures and is not presently being operated as a commercial business. Buyer to verify zoning, permitted uses, development potential and all information important to buyer's intended use with the Town of Eatonville.

307 Lemon Street, Maitland

Listing courtesy of HOME REALTY GROUP LLC. 321-689-0751
$560,000
4 Beds ⋅ 2 Baths ⋅ O6435957 MLS
Welcome to Maitland living, where space and everyday convenience come together. This 3-bedroom, 2-bath home offers a surprisingly flexible floor plan with a formal living area, dining space, fireplace, open-concept kitchen and living areas, plus a separate family room and an additional flex space that could easily become a home office, playroom or 4th bedroom. Outside, a fenced backyard offers plenty of room to enjoy Florida living. But it may be the location that makes this home such a find. This home puts you close to some of Maitland’s favorite places, including Minnehaha Park, Lake Lily Park and the shops, dining and gathering spots around downtown Maitland. You are also in a great proximity to highly requested schools such as Dommerich Elementary, Maitland Middle School and Winter Park High School. Enjoy weekends at the farmers market, dinner nearby, neighborhood parks and easy access to Winter Park, all while coming home to an established Maitland neighborhood. A home with room to live, work and grow, right in the heart of the Maitland lifestyle.

1540 E Horatio Avenue, Maitland

Listing courtesy of LUXE HUNTER REAL ESTATE. 407-984-4888
$412,800
3 Beds ⋅ 2 Baths ⋅ GC542965 MLS
Virtually Staged. Move-in ready and thoughtfully updated, this 3-bedroom, 2-bath block home offers approximately 1,750 square feet of living space on a .33-acre double corner lot in Maitland. Located across two parcels, the property provides additional outdoor space, added privacy, a partial new wood fence, and a beautiful live oak canopy. Inside, luxury vinyl flooring flows throughout the home, complemented by fresh interior and exterior paint, new ceiling fans, and updated door hardware. The refreshed kitchen features newer cabinets, granite countertops, and coordinating appliances. A Florida room provides flexible space for a home office, sunroom, playroom, or additional sitting area. Both bathrooms have been updated. The guest bathroom includes a tub-and-shower combination, new tile surround, new hardware, pedestal sink, mirror, and light fixture. The primary bathroom features a new vanity, mirror, and lighting. Major improvements include a roof and water heater replaced in 2021 and a new septic system installed in 2024. Conveniently located near downtown Maitland, Winter Park, Altamonte Springs, Longwood, Casselberry, and downtown Orlando, this home offers comfortable living with easy access to shopping, dining, employment centers, and major roadways.

1202 Oranole Road, Maitland

Listing courtesy of ANSON PROPERTIES LLC. 352-535-0620
$739,000
3 Beds ⋅ 3 Baths ⋅ O6434173 MLS
Under contract-accepting backup offers. Situated on a quiet, tree-lined street in the highly sought after and desired Dommerich neighborhood this home is just a short walk or bike ride to DOMMERICH Elementary and Maitland Middle schools. This charming residence has been thoughtfully renovated and offers the best of old world charm and modern updates. Some of this homes many features include an renovated oversized kitchen with breakfast bar seating, indoor laundry room with office space, beautiful hardwood flooring, updated bathrooms, newer AC system installed in 2023/24 and a bright and open floorplan which is perfect for indoor/outdoor entertaining. Located in a fabulous school district and is conveniently located to all the great amenities the Maitland and Winter Park lifestyles have to offer. Residents also enjoy deeded lake access to the Winter Park Chain-of-Lakes with boat ramp, panic area and dock with canoe/paddleboard storage. This home should be viewed in person to truly appreciate what a rare find it is!

1761 Tippicanoe Trail, Maitland

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
$699,000
4 Beds ⋅ 3 Baths ⋅ O6434947 MLS
Under contract-accepting backup offers. RARE OPPORTUNITY! Nestled on .68 acres in one of Maitland‘s most established and beautiful neighborhoods, Hidden Estates, this single story 4 bedroom, 2.5 bath pool home is filled with loads of character and charm. Once you enter the handsome foyer with brick flooring, you will notice the spaciousness of this home, which is one of its greatest features. The beautiful mature landscaping and plenty of room to enjoy the outdoors provides this property with an incredible sense of privacy that is so increasingly hard to find! The great room with brick fireplace and adjacent living room, as well as the kitchen, overlook the large pool and expansive deck just perfect for entertaining or simply relaxing in your own backyard retreat. The inside utility room and half bath are conveniently located right off of the kitchen. The large game room/office/workout room has lots of cabinetry for wonderful storage space. The home’s layout offers tremendous potential for a buyer ready to renovate while preserving its unique warmth and character. Convenient access to shopping, dining, schools, and medical facilities adds to it’s desirable location. This long time, family home awaits its next chapter, offering it’s new owner an exceptional setting to preserve or create something truly special. Look forward to seeing you there!

212 Flame Avenue, Maitland

Listing courtesy of COLDWELL BANKER REALTY. 407-647-1211
$375,000
2 Beds ⋅ 2 Baths ⋅ O6435325 MLS
LOCATION, LIFESTYLE & LOW-MAINTENANCE LIVING IN THE HEART OF MAITLAND/WINTER PARK! Welcome to Maitland House, a hidden gem perfectly positioned between Maitland and Winter Park, where convenience, character and an unbeatable lifestyle come together. Located just steps from the iconic Enzian Theater and its lush Eden Bar, and minutes from Winter Park Village, Lake Lily and Park Avenue, this beautifully updated second floor 2 bedroom, 2 bath condo puts some of Central Florida’s best dining, entertainment, shopping and nightlife right outside your door. Inside, you’ll find a bright and inviting open floor plan with thoughtful updates throughout. The spacious living area features a wood burning fireplace, granite countertops, plantation shutters and custom-built closet systems with abundant shelving, drawers, shoe storage and hanging space. Step outside to your screened, pool view porch, the perfect spot for morning coffee, an evening glass of wine or simply enjoying the peaceful surroundings. The kitchen is equipped with a 2025 dishwasher, 2021 refrigerator, range and microwave, while the home also features a BRAND NEW water heater. The 2019 HVAC system includes electrostatic filtration and a UVC air purification system, with air ductwork replaced in 2024. Additional improvements include updated windows and attic insulation replaced in 2021. Maitland House offers the kind of amenities and conveniences that make everyday living easy. Enjoy a tranquil pool and clubhouse, community bathrooms, Weber Genesis grill, covered dog walk area, community laundry room with three large washers and three dryers, covered assigned parking and an assigned storage unit. The community itself has been well maintained, with exterior painting completed in 2025 and the parking lot resurfaced in 2026. And the HOA delivers exceptional value. Included with the association are water, sewer, exterior maintenance, and an impressive Spectrum entertainment and connectivity package. Schedule your showing today!

210 Magnolia Road Unit 207, Maitland

Listing courtesy of PREFERRED REAL ESTATE BROKERS. 407-440-4900
$950,000
5 Beds ⋅ 4 Baths ⋅ O6435185 MLS
Coveted Maitland Location – Renovate or Build New! A rare opportunity to create your dream home in one of Maitland’s most sought-after communities. Situated on nearly half an acre along a quiet, beautiful street, this 5-bedroom, 3.5-bath home offers a spacious floor plan, an oversized pool, and endless potential. Renovate the existing home and make it your own or take advantage of the incredible homesite and build the home you’ve always envisioned. With the property already replumbed and rewired, there’s a great foundation for a thoughtful renovation. And then there’s the location—you simply can’t beat it. Enjoy the charm and convenience of Downtown Maitland, with its local restaurants, shops, farmers market, parks, and community events all nearby. Stroll to neighborhood favorites, spend a morning at the Maitland Farmers Market, or enjoy the beautiful grounds, museums, and gardens of the Art & History Museums of Maitland. Winter Park and Park Avenue are just a short drive away, along with convenient access to major roadways and the airport. Whether you choose to reimagine the existing home or start fresh, this is a special opportunity to create something truly your own in a community you’ll never want to leave.

60 Oakleigh Lane, Maitland

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
$250,000
3 Beds ⋅ 2 Baths ⋅ O6425600 MLS ⋅ 416 BLDG.
Move-in ready 3-bedroom, 2-bath condo in the heart of Maitland! This beautifully maintained home features an open-concept layout, abundant natural light, and ceramic tile flooring throughout. The updated kitchen offers generous cabinetry, stylish countertops, decorative backsplash, stainless steel appliances, breakfast bar, and views of the community pool. The spacious primary suite features a walk-in closet and private ensuite bath, while two additional bedrooms offer flexibility for family, guests, or a home office. Enjoy the convenience of a full-size stacked washer and dryer, ample storage, and generous closet space. Community amenities include a sparkling pool, picnic areas, BBQ grills, and mature landscaping. Ideally located within walking distance of Casselberry Commons, offering Publix, Starbucks, shopping, dining, and more, with easy access to major highways and Central Florida attractions.

416 Banyon Tree Circle Unit 108, Maitland

Listing courtesy of FORTEX REALTY INC. 305-600-7893
$459,000
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
$184,900
2 Beds ⋅ 2 Baths ⋅ O6435451 MLS ⋅ 3 BLDG.
**Welcome to Carrington Park, a beautifully maintained community in the heart of Maitland!** This spacious **2-bedroom, 2-bathroom condo** offers **over 1,200 square feet** of comfortable living space and has been lovingly cared for as a seasonal winter home, reflecting its exceptional condition throughout. Step inside to discover a bright and inviting floor plan featuring **vaulted ceilings**, **no carpet throughout**, and **newer kitchen appliances**, creating a clean, low-maintenance living environment. The home is being offered **mostly furnished**, making it an ideal opportunity for a primary residence, seasonal retreat, or investment property. Enjoy the convenience of a well-maintained community with a beautiful swimming pool and peaceful surroundings, all while being just minutes from abundant shopping, popular restaurants, entertainment, and major roadways for easy access throughout Central Florida. Located in one of Maitland's most established and desirable areas, this move-in-ready condo combines comfort, convenience, and exceptional value. **Whether you're looking for a full-time residence, a winter getaway, or an investment opportunity, this is a home you won't want to miss. Schedule your private showing today!**

2305 Haywood Court Unit 203, Maitland

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155
$500,000
4 Beds ⋅ 3 Baths ⋅ O6435294 MLS
Under contract-accepting backup offers. A beautifully renovated, move-in ready family home is now available in the established Winfield community in the heart of Maitland. This 4-bedroom, 3-bathroom, two-story property, set on 2,321 square feet of thoughtfully updated living space, combines fresh modern finishes with the long-term peace of mind every family deserves. Step inside to a bright, open layout filled with natural light, complemented by brand new flooring, fresh paint and modern fixtures throughout. The fully renovated kitchen takes center stage with gorgeous Olive Green solid wood shaker cabinets featuring soft-close hinges, elegant Quartz countertops, brand new appliances and a clean, timeless design built to stand the test of time. All bathrooms have been fully updated with a fresh, modern feel, while major improvements including a brand new roof, a fully serviced AC and a new water heater offer the kind of worry-free ownership that lets you focus on what really matters; making everlasting memories with your family. Outside, the property continues to shine with a large backyard and a spacious two-car garage, creating the ideal setting for weekend gatherings, quiet evenings and everyday enjoyment. Set within Winfield, a well-established neighborhood of quiet streets and mature landscaping where pride of ownership is evident and neighbors create a genuinely welcoming atmosphere, this is a community that has stood the test of time. Conveniently located just minutes from the Genesis mega gym, Lake Shadow Park, the Maitland Center business district and the shopping and dining along Maitland Boulevard, with quick access to I-4, HWY 414, historic downtown Maitland, Winter Park's Park Avenue, the Maitland SunRail station and both the Orlando International Airport (MCO) and Orlando Sanford International Airport (SFB), this home truly offers the ideal blend of lifestyle, comfort and location. This is a fantastic opportunity to plant roots in one of Central Florida's most convenient and sought-after communities. Reach out to your preferred real estate professional today to schedule your private showing before it's gone.

7909 Chartreux Lane, Maitland

Listing courtesy of REALTY HUB. 888-900-1801
$475,000
3 Beds ⋅ 2 Baths ⋅ O6433275 MLS
Do you enjoy boating, fishing, and relaxing days on the water just moments from home? This beautiful three bedroom two bath block home offers private access to Lake of the Woods in Maitland Florida! Inside you will find; porcelain wood-plank tile flooring flows throughout, providing a clean, modern look with easy maintenance, major improvements including a 2026 HVAC, 2019 roof, PEX plumbing, 200-amp electrical service, newer septic system, and hurricane panels. Outside, the property offers exceptional functionality with a spacious driveway accommodating up to five vehicles, a two-car garage, heavy-duty metal storage shed, and a screened lanai ideal for relaxing or entertaining. Conveniently located in Maitland with easy access to Interstate 4, for commuting, shopping, dining, east and west coast beaches, two international airports, and world renowned theme parks. This home combines meaningful updates, generous parking, storage, and the lifestyle benefit of private lake access—all in one desirable location.

106 S Lakewood Circle, Maitland

Listing courtesy of KELLER WILLIAMS HERITAGE REALTY. 407-862-9700
$475,000
4 Beds ⋅ 2 Baths ⋅ O6433200 MLS
Under contract-accepting backup offers. This meticulously maintained 4-bedroom, 2-bath home is located in English Estates on a street where neighboring homes sell for significantly more—giving you the opportunity to build instant equity! The home is on city sewer, and recent improvements include fresh paint, new carpet (2026), a 2018 roof, and a new dishwasher, range and range hood. The efficient kitchen features original wood cabinets that have been beautifully restored and updated with new hardware, adding warmth, character, and timeless appeal. With lots of counter space, a window over the sink, and a large breakfast bar, the kitchen is both functional and inviting. It seamlessly connects to the family room, which features a wonderful brick fireplace and sliding glass doors leading to the outdoor patio overlooking a private, fenced backyard. The home also boasts both formal living and dining rooms, providing plenty of space for entertaining. The spacious primary bedroom offers a large walk-in closet, while the great secondary bedrooms provide flexibility for family, guests, or a home office. Beautiful terrazzo flooring is located underneath the carpet, offering the opportunity to restore a classic feature of the home. A large brick driveway provides ample parking for residents and guests, and the home is conveniently within walking distance of English Estates Elementary School. This home is truly ready for you to make it your own, offering a desirable location, spacious layout, and an incredible opportunity to build equity. Conveniently located near shopping, restaurants, and major roads, this home offers both comfort and convenience. Call today to schedule your private viewing of this wonderful home!

2453 Worthington Road, Maitland

Listing courtesy of FANNIE HILLMAN & ASSOCIATES. 407-644-1234
$155,000
1 Beds ⋅ 1 Baths ⋅ O6432801 MLS ⋅ 476 BLDG.
Discover comfort, style, and convenience in this beautifully renovated and tastefully furnished first-floor condominium in the centrally located Carrington Park community. This inviting home features brand-new tile flooring throughout and a thoughtfully updated kitchen with wood cabinetry, stainless steel appliances, granite countertops, and a spacious pantry for excellent storage. The generously sized bedroom includes a walk-in closet, offering plenty of room for organization. The updated bathroom features a walk in shower, new toilet and vanity. Carrington Park provides a desirable lifestyle with multiple swimming pool areas, a fitness facility, playground, and a peaceful courtyard for relaxation. Ideally located just steps from shopping and near the intersection of Howell Branch Road and 436, this condo offers easy access to major destinations, including UCF, Valencia, and Full Sail. A great opportunity for those seeking a move-in ready home in a convenient central location.

476 Banyon Tree Circle Unit 104, Maitland

Listing courtesy of CORCORAN PREMIER REALTY. 407-965-1155
$349,999
3 Beds ⋅ 2 Baths ⋅ O6432604 MLS
Under contract-accepting backup offers. Beautiful Winfield Community home in Maitland Florida will not last long. This 3 bedroom/2 bath home has so much to offer. The property recently has had a new roof put on this year in 2026, new AC unit this year in 2026, and freshly painted in 2026. The kitchen features an eat in bar top as well as a large island for plenty of use-able countertop space. The back yard is fully fenced in for privacy. The home comes with a stove, refrigerator, microwave, washer, and dryer. The garage is oversized for 2 cars with extra space for storage. The flooring is ceramic in the main living areas for easy cleaning when needed. Low HOA dues for an upscale community. Dont miss out on this home.

1866 Bobtail Drive, Maitland

Listing courtesy of 407 PROPERTIES. 407-545-2594
$425,000
3 Beds ⋅ 2 Baths ⋅ O6432182 MLS
Under contract-accepting backup offers. Waterfront potential on Brookside Circle! Classic 3-bedroom, 2-bathroom property situated directly on peaceful Howell Creek with canoe access to Waumpi Lake. Renovation opportunity! The interior layout includes a living room with a window nook, a dedicated dining area, and a primary suite located off the dining room. The kitchen features a breakfast nook and opens directly into the main living area. A split floor plan places two secondary bedrooms on the opposite side of the home, alongside an indoor, air-conditioned laundry room. The second full bath opens directly to the screened pool deck to serve as a dedicated pool bath. The property sits on an expansive lot featuring a wide side yard and a deep backyard running along the creek. Filled with warmth and pride of ownership, the home showcases unique, hand-painted artistic touches throughout that reflect years of love—ready for the next owner to bring their own style. Ready for a complete transformation, this property presents an exceptional waterfront renovation opportunity. Schedule your tour today!

535 Brookside Circle, Maitland

Listing courtesy of FIRST MAGNOLIA HOMES. 407-963-9141
$979,000
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
$340,000
3 Beds ⋅ 2 Baths ⋅ O6432341 MLS ⋅ Na BLDG.
Welcome to this beautifully maintained 3-bedroom, 2-bathroom condo in the desirable Sierra Condominium Association, offering a comfortable split-bedroom floor plan, private attached garage, exceptional curb appeal, and a serene outdoor setting. The meticulously maintained landscaping features a stunning bougainvillea plant, adding vibrant color and charm to the home's inviting exterior. Inside, wood flooring extends through the family room, hallway, and primary bedroom, adding warmth and character to the living spaces. The spacious family room features a wood-burning fireplace and additional storage closet space, providing both a cozy gathering area and convenient functionality. The kitchen offers 42-inch wood cabinetry with ample storage and provides a functional space for everyday cooking and entertaining. The open flow into the main living areas makes it easy to stay connected with family and guests. The split-bedroom floor plan provides added privacy, with the spacious primary suite thoughtfully separated from the additional bedrooms. The primary bedroom features wood flooring, while both full bathrooms are equipped with walk-in showers and porcelain tile flooring, adding a clean, durable, and stylish finish. The HVAC system was replaced in 2020 and has been routinely serviced for added peace of mind. Enjoy the tranquility of your private outdoor space with a paver patio and covered pergola overlooking a peaceful creek—an ideal spot for morning coffee, outdoor dining, or unwinding at the end of the day. The property also includes a private attached one-car garage, providing convenient parking and additional storage. Residents of the Sierra Condominium Association enjoy desirable community amenities, including a community swimming pool and tennis courts, with cable and internet included in the association fees for added convenience and value. Conveniently located near shopping, dining, entertainment, and major roadways, this home provides easy access to Orlando and surrounding communities while offering a peaceful retreat to call home. Combining low-maintenance living, beautiful landscaping, thoughtful storage, desirable amenities, and a tranquil creekside setting, this Sierra condo is an opportunity you won't want to miss.

2362 Sierra Lane, Maitland

Listing courtesy of SAFFORD REAL ESTATE LLC. 407-461-3172
$775,000
5 Beds ⋅ 3 Baths ⋅ O6432757 MLS
**PRICE IMPROVEMENT ON THIS STUNNING LAKEFRONT RETREAT IN MAITLAND!** Step into your next chapter at this exceptional lakefront property, where striking curb appeal is only the beginning. Perfectly positioned along the serene shores of **Lake Ruby**, this home blends timeless character with thoughtful modern updates. Inside, natural light pours through dramatic vaulted ceilings, illuminating spacious open living areas. The main gathering space flows seamlessly into the dining area, both showcasing **panoramic lake views** through expansive **updated sliding doors**, complemented by **built-in shelving** and **skylights** that enhance the airy ambiance. For the culinary enthusiast, the kitchen is more than a workspace—it’s a creative haven featuring **Corian countertops**, **tile backsplash**, abundant cabinetry, and **stainless steel appliances**, including a **newer dishwasher**. A charming **garden window** offers the perfect spot for plants or décor, while the eat-in nook provides yet another **stunning lakefront view**. Enjoy casual meals here or take the experience outdoors to the **incredible deck**, where Florida breezes set the tone for unforgettable gatherings. The formal dining room, anchored by a **wood-burning fireplace**, invites cozy evenings and intimate celebrations. Nearby, a versatile family room adapts to your lifestyle—ideal as an office, den, playroom, or even a fifth bedroom—with sliders leading to the **screened-in porch** and more peaceful lake scenery. The master suite is a true sanctuary, complete with a **private deck** overlooking Lake Ruby—perfect for sunrise reflections or unwinding at day’s end. The spa-inspired bathroom features designer tile and a rejuvenating shower, while the walk-in closet offers exceptional organization. Additional bedrooms provide comfort for family or guests, each with access to **updated bathrooms** that balance style and practicality. The home also includes an **indoor laundry room** with sink and **2-year-new washer and dryer**, plus numerous major updates: **roof (2019)**, **water heater (2023)**, **plumbing (2022)**, **AC (2017)**, and **irrigation with reclaimed water**. The beautifully landscaped **large corner lot** enhances the property’s charm. Convenience is unmatched with easy access to Maitland’s top amenities, schools, and major highways. This isn’t just a home—it’s a lifestyle, offering beauty, comfort, and the rare opportunity to live lakefront in one of the area’s most desirable communities. Homes with this level of character and luxury don’t come around often. Claim your future here.

956 Stonewood Lane, Maitland

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

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