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$1,125,000
4 Beds 4 Baths O6412977 MLS
Welcome to a life beautifully lived. Situated on a premier corner lot in Oakland Park, Winter Garden's golf cart community, this exceptional residence blends thoughtful design, effortless indoor-outdoor living, & a private tropical retreat. Freshly redesigned professional landscaping with premium weed barrier, smart irrigation, app control, & a mature Medjool date palm creates stunning curb appeal. A custom front door opens to a partially screened wraparound front porch, perfect for morning coffee or evening chats. Inside, rich hardwood floors span the main level, complemented by abundant natural light, crown molding, plantation shutters, designer lighting, brass floor outlets in the living room & office, and ceiling fans throughout. The kitchen features granite countertops, a farmhouse sink, stainless steel appliances, tile backsplash, under-cabinet lighting, a beverage refrigerator, & a new Bosch dishwasher and microwave (2023). Open to the living & dining areas, it overlooks the front porch & connects seamlessly to outdoor living through French doors. A flexible front room serves as an office, study, or playroom. A powder room serves guests. The first-floor owner's suite overlooks the pool & offers dual granite vanities, a spa-style walk-in shower, linen storage, custom California Closets, & direct laundry room access. Upstairs, hardwood flooring continues throughout 3 spacious bedrooms, including one en-suite, plus two full baths and a generous loft ideal for theater, fitness, playroom, or guest retreat. A whole-home Generac natural gas generator keeps lights, air conditioning, & appliances running during outages. Step outside to one of Oakland Park's rare full-size Jandy-iAqualink-controlled saltwater pool & spa. The pool measures approximately 12' x 30' with depths from 3' to 5' & features an 8' x 12' sun shelf with bubbling fountain and umbrella sleeve. The approximately 6' x 8' spa includes four therapy jets and heats in 20-30 minutes. Equipment includes a 2.7 HP Jandy Variable-Speed Energy-Efficient Pump & Jandy 400,000 BTU natural gas heater. A travertine pool deck, oversized covered rear porch, vinyl-fenced yard with dual gates, & three-car garage with built-in storage racks complete the outdoor experience. Oakland Park offers a waterfront, golf-cart-approved lifestyle with two resort-style pools, a clubhouse, dog park, playgrounds, parks, & spectacular sunsets. Two blocks from the waterfront trail, minutes from the 22-mile West Orange Trail, & near multiple parks. Historic downtown Winter Garden is a golf cart ride away, offering Crooked Can Brewery, rooftop dining, boutique shopping, splash park, Farmers Market, live theater, golf cart parades, 5Ks, book clubs, poker nights, and more. Convenient access to major interstates, premier golf courses, shopping, & Central Florida theme parks. Additional features: fresh interior/exterior paint (2021), Apple HomeKit-compatible door locks, thermostats & ceiling fans, Apple Secure Video cameras at the doorbell, front entry, pool area & indoor locations, new remote-controlled high-velocity fans on both porches, Apple HomeKit-controlled owner's bath fan, outlets inside primary bath cabinetry, & a state-of-the-art termite detection and control system with full warranty. Lovingly maintained & thoughtfully enhanced throughout, this one-of-a-kind Oakland Park pool & spa home is a special opportunity. Your oasis is waiting. Make it yours.

925 Easley Avenue, Winter Garden

Listing courtesy of COMPASS FLORIDA LLC. 407-203-9441

$989,990
5 Beds 5 Baths G5113803 MLS
Virtually Staged. The Venice is a two-story home designed for efficient and flexible living. The first floor features an open-concept layout with a centrally located kitchen overlooking the dining area and main living space. The primary bedroom is located on the main level and includes a walk-in closet and en-suite bathroom, offering privacy and convenience. A flex room with walk in closet and a half bathroom are also located on the first floor, along with direct access to the garage and additional storage. The second floor includes additional secondary bedrooms with access to full bathrooms, a central loft providing flexible living space, and a dedicated laundry area. A secondary primary bedroom is also located on the second floor, featuring its own en-suite bathroom and walk-in closet, making it ideal for multi-generational living or extended stays.

15154 Tea Tree Drive, Winter Garden

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com

$699,000
2 Beds 2 Baths O6415871 MLS
Welcome to this ELEGANTLY UPGRADED and nearly new 2-bedroom, 2-bath residence in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where resort-style living meets everyday sophistication. Perfectly situated on one of ONLY TWO PREMIUM HOMESITES of its kind within the community, this exceptional property enjoys a truly rare distinction: an EXCLUSIVE SIDE EASEMENT that creates exceptional privacy, expanded green space, and a level of openness rarely found in community living, with no immediate neighbor on one side and convenient proximity to the clubhouse area. From the moment you arrive, the home impresses with its REFINED CURB APPEAL, lush landscaping, and a spacious 2-car garage enhanced with CUSTOM STORAGE SOLUTIONS. Inside, a bright OPEN-CONCEPT LAYOUT welcomes you with abundant natural light and meticulous attention to detail throughout every space. The Kitchen is a TRUE SHOWPIECE, equipped with premium stainless steel appliances, a GAS COOKTOP, BUILT-IN OVEN, a CUSTOM BUILT-IN PANTRY WITH PULL-OUT DRAWERS, generous cabinetry, and stone countertops, all seamlessly flowing into the living and dining areas. The Living Room has been elevated with an INTEGRATED SURROUND SOUND SYSTEM, creating the perfect setting for daily enjoyment and entertaining. The Primary Suite is a private retreat featuring a CUSTOM-DESIGNED WALK-IN CLOSET SYSTEM and a well-appointed en-suite bath with dual vanities, generous storage, and a walk-in shower. An additional SECONDARY BEDROOM provides comfortable accommodations for family or guests, while the DEDICATED DEN, enhanced with UPGRADED HIGH BASEBOARDS and RECESSED LIGHTING, offers the flexibility of a home office, hobby room, or formal sitting area. CUSTOM CLOSET SYSTEMS throughout ensure every space is as functional as it is beautiful. Step outside to where this property truly STANDS APART. The expansive SCREENED-IN LANAI opens to an EXTENDED OUTDOOR DECK and a fully appointed BUILT-IN OUTDOOR KITCHEN (BBQ Area), all framed by CUSTOM OUTDOOR LIGHTING, creating an exceptional outdoor retreat designed for year-round Florida living. Additional highlights include a WHOLE-HOME WATER FILTRATION AND SOFTENER SYSTEM, FRESH INTERIOR PAINT throughout, and additional RECESSED LIGHTING both inside and outside that elevates the home's ambiance day and night. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a 12,000 SF clubhouse with coffee bar, lounge, and wine lockers, a sparkling pool, state-of-the-art fitness center, tennis courts, and a vibrant social calendar, along with included cable and internet, fostering the active and connected lifestyle that Del Webb is famous for. IDEALLY LOCATED in Winter Garden, you are just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for boutique shops, dining, and a weekly farmers market. Enjoy outdoor recreation along the WEST ORANGE TRAIL, or take a short drive to WORLD-CLASS ATTRACTIONS including Walt Disney World Resort and Universal Studios. Convenient access to FL-429 and major roadways makes it easy to enjoy the very best of Central Florida. This exceptional residence offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living on one of the community's most coveted homesites, where every upgrade has been thoughtfully chosen and every detail meticulously executed. Homes of this caliber and setting are a TRUE RARITY in Del Webb Oasis. Now is the time, don't miss your chance to call this home.

15139 Canopy Cover Drive, Winter Garden

Listing courtesy of INTERNATIONAL TEAM INC. 321-388-1372

$585,000
4 Beds 3 Baths O6409661 MLS
Such a Charming, Family-Friendly 4 Bedroom 2.5 Bath Home in Beautiful Winter Garden. The bungalow-style porch is extremely inviting as you enter the home. Arched doorways, recessed lighting, French doors, transom windows, and a separate office on the first floor. Tons of natural lighting. The kitchen includes solid granite countertops, solid wood cabinetry, custom tile backsplash, and an island storage prep station. and a Pantry! Oversized primary bedroom upstairs, with an ensuite bathroom leading to a roomy walk-in closet with pocket doors. Ensuite Bath includes a glass-walled shower with a separate spa-style tub. Dual sinks with plenty of counter space. Solid wood cabinetry and Stone countertops. 3 additional Bedrooms on the second floor. Full laundry room with cabinetry. Welcome to Independence, one of the most desirable communities in Central Florida! Ideally located within walking distance of A-rated schools, shopping, dining, and fun for the whole family. Whether envisioning a pool, an expanded patio, or simply more room to relax and play, this space is a true standout in the neighborhood. Residents of Signature Lakes enjoy resort-style amenities including two clubhouses, tennis and basketball courts, two swimming pools, dog parks, scenic walking and biking trails, and beautifully landscaped green spaces. These neighborhoods would be inspired by the traditional aesthetic of Colonial America, with streets named after agricultural methods, explorers, authors, artists, and more. The "icon" for the community is the Mall, situated at the entrance to the community off Ficquette Rd. Two large stone obelisks, alight with gas torches in the evening, give way to the sparkling 512-foot reflecting pond surrounded by emerald green lawn and stately mature oak trees. At the Tower Green stands the five-story brick Clock Tower, trimmed by ornamental gardens and capped with a copper spire. The Town Square Residents Club ends the Mall, with its colonnaded façade and tall cupola drawing inspiration from Georgian colonial buildings of historic Philadelphia, New York, and Boston. This prime Winter Garden location offers quick access to SR-429 and is minutes from shopping, dining, and entertainment. This home is the perfect blend of style, comfort, and location, and is ready to welcome its next owner. At Independence, they are proud to be among the finest master planned communities in Horizon West. Full of dramatic architectural flourishes, surrounded by the majesty of natural Florida, and home to a lifestyle that's second to none, we welcome you to explore this beautiful community and discover that this unique place truly is what life should be.

6316 Manuscript Street, Winter Garden

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS. 407-629-4420

$540,000
3 Beds 3 Baths S5151791 MLS
LOCATION, LOCATION, LOCATION!!! Why wait to build when you can own this like-new home right now? Seller's existing FHA loan features a 4.997% fixed interest rate. Original loan date: 01/22/2024 (30-year term). Current loan balance is approximately $487,000.Seller will contribute up to $10,000 toward the buyer's closing costs. Welcome to your dream home in the heart of Horizon West, Florida! This charming 3-bedroom, 2.5-bath residence is the epitome of comfortable, convenient living. Situated in picturesque Winter Garden, FL, this home offers the perfect blend of modern amenities and a peaceful suburban setting, located right across from the new Hamlin elementary and middle schools. Upon entering, you are greeted by an inviting living space filled with natural light—ideal for both relaxation and entertaining. The spacious open-concept kitchen is a chef's delight, featuring quality appliances, ample quartz counter space, and a convenient pantry. The great room is perfect for family meals or hosting friends, while the downstairs half-bath adds convenience; the main level also offers generous storage space and direct kitchen-to-garage access, making unloading groceries a breeze. Upstairs, the primary suite serves as a true retreat, complete with a private bath and spacious closets. Two additional bedrooms offer flexibility for a growing family, and the loft—featuring a shared full bath—provides the perfect spot for a home office or family entertainment area. Step out onto your modern porch; Silverleaf Reserve invites you to enjoy a serene escape with community amenities such as a pool, playgrounds, and walking trails. Additionally, the nearby Hamlin area offers excellent conveniences, including parks, trails, and shopping centers—with banks, restaurants, Walmart, Publix, a movie theater, a hospital, and a gym—plus easy access to the best of Florida living: Disney theme parks. With the added benefit of being just steps away from the new Hamlin elementary and middle schools, your family will enjoy a short, safe commute to school. Don't miss the opportunity to make this Horizon West bungalow your new home sweet home—not to mention its convenient location for accessing the US-429 toll road and easy access to Highways 192, 27, and 50. Schedule a visit today and experience the charm of Florida living at its best!

4958 Citrus Leaf Blvd, Winter Garden

Listing courtesy of MBT REALTY LLC. 407-283-3351

$523,990
3 Beds 3 Baths G5113698 MLS
Virtually Staged. Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the primary suite offers a perfect end-of-day retreat with a large walk-in closet and a generously sized bedroom. Introducing Serenade at Ovation, within the fast-growing Horizon West community, offers a prime location near top Winter Garden schools, Walt Disney World, Hwy 192, SR 429, Flamingo Crossings, and Hamlin. The diverse housing options include townhomes, new bungalows, and award-winning single-family homes, providing affordable living in this burgeoning area. Abundant green spaces, pocket parks, and the central Area Community Park with its engineered wood fiber playground, shaded pavilion, and dog parks, make this community an ideal, family-friendly choice at the heart of Horizon West.

13019 Serene Glade Road, Winter Garden

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com

$475,000
4 Beds 3 Baths S5151845 MLS
Location, Location, Location! Welcome to this beautiful 4-bedroom home located in the highly desirable Hamilton Gardens community in Winter Garden. Just minutes from Hamlin Town Center, you’ll enjoy convenient access to shopping, restaurants, coffee shops, movie theaters, fitness centers, Publix, and everyday essentials. This spacious home features 4 bedrooms, with all bedrooms conveniently located upstairs, creating a functional layout that offers privacy and separation from the main living areas. Downstairs, you’ll find a versatile flex space that can be used as a home office, study area, playroom, or additional sitting room. The open-concept kitchen features a gas stove, perfect for those who enjoy cooking and entertaining. The kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and everyday living. Residents of Hamilton Gardens enjoy access to the community swimming pool and beautifully maintained neighborhood amenities. The home is also conveniently located near SR-429, providing quick access to Disney, Downtown Winter Garden, Downtown Orlando, and other major destinations throughout Central Florida. Families will appreciate the excellent school district, including highly rated elementary and middle schools, making this one of the most desirable areas in Winter Garden.

5754 Surprise Lily Drive, Winter Garden

Listing courtesy of NUMBER 1 BROKER, LLC. 407-566-3400

$544,990
3 Beds 3 Baths G5113670 MLS
Virtually Staged. Discover the Copper, an open bungalow floor plan that will enhance your living experience with its spacious layout, including 3 bedrooms, 2.5 bathrooms, a loft, and a 2-car garage. The moment you walk through the front door, the openness of the home welcomes you, leading directly to a show-stopping gourmet kitchen with a long island ideal for entertaining friends and other guests. Upstairs, the primary suite offers a perfect end-of-day retreat with a large walk-in closet and a generously sized bedroom. Introducing Serenade at Ovation, within the fast-growing Horizon West community, offers a prime location near top Winter Garden schools, Walt Disney World, Hwy 192, SR 429, Flamingo Crossings, and Hamlin. The diverse housing options include townhomes, new bungalows, and award-winning single-family homes, providing affordable living in this burgeoning area. Abundant green spaces, pocket parks, and the central Area Community Park with its engineered wood fiber playground, shaded pavilion, and dog parks, make this community an ideal, family-friendly choice at the heart of Horizon West.

13031 Serene Glade Road, Winter Garden

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com

$2,575,000
5 Beds 7 Baths O6415007 MLS
Pre-Construction. To be built. Welcome home to The Wildflower, an exquisitely crafted new construction estate nestled within the exclusive community of The Grove in charming Oakland, Florida. Masterfully built by the renowned Justice & Wood Builders — whose principals each bring over 25 years of custom homebuilding experience — this stunning residence delivers the perfect blend of timeless craftsmanship, thoughtful design, and elevated luxury living. Spanning 4,210 square feet of livable space (5,914 total sq ft) across a thoughtfully designed floor plan, The Wildflower offers 5 bedrooms, 5 full baths, and 2 half baths, providing ample room for families who prioritize space and style. From the moment you arrive, every detail speaks to the quality and care poured into this home. Inside, a versatile loft and flex room provides endless possibilities — a home office, media room, playroom, or private retreat. The open, flowing layout is designed for both everyday living and effortless entertaining. Step outside to your own private resort. A custom pool and spa take center stage in the backyard oasis, a covered rear lanai with roll down screens, a fireplace complemented by a summer kitchen and cabana — perfect for hosting under the Florida sun. Enjoy evenings at home with a built in fire pit and beautiful landscape lighting. A 3-car garage rounds out the thoughtful features that make this home as functional as it is beautiful. Located just minutes from downtown Winter Garden's vibrant dining and shopping scene, top-rated schools, and easy access to the Florida Turnpike, The Grove offers the rare combination of peaceful small-town living with big-city convenience. Estimated completion Spring 2027. Secure your lot today and experience the Justice & Wood difference — where every home is built with excellence, without cutting corners.

1155 Prado Lane, Winter Garden

Listing courtesy of REGENCY REAL ESTATE LLC. 407-469-5021

$1,200,000
6 Beds 4 Baths O6415935 MLS
Experience elevated living perfectly situated on a private conservation homesite with no rear neighbors in the gated community of Lake Roberts Landing in Winter Garden. This fully renovated luxury pool home offers an exceptional blend of privacy, elegance, and convenience in the heart of Winter Garden. Spanning over 4,200 square feet, this move-in-ready home features 6 bedrooms, 4 bathrooms, a 3-car tandem garage, dedicated theater room, expansive upstairs loft and a resort-style backyard with an outdoor kitchen designed for year-round Florida living. Every major finish has been thoughtfully updated, including new flooring throughout, fresh interior and exterior paint, a completely renovated chef’s kitchen with upgraded countertops, appliances, lighting, and beautifully updated bathrooms that create a modern yet timeless aesthetic. The versatile floor plan includes two bedrooms and a full bathroom on the main level, providing the perfect setup for guests, multigenerational living, a home office, gym, or flex space, while also serving as a convenient pool bath. Heading upstairs, you’ll immediately notice the updated wrought iron spindles, luxury vinyl plank flooring, and abundant natural light that fills the space. The expansive loft serves as the ultimate entertainment hub, complete with a spacious sitting area, custom bar, bar refrigerator, mounted TV, and designer lighting, creating the perfect space for hosting family and friends or enjoying the big game. A dedicated theater room provides the ideal setting for movie nights and elevated at-home entertainment. The luxurious primary suite serves as a private retreat featuring a fully renovated spa-inspired bathroom with dual vanities, makeup vanity, freestanding soaking tub, oversized walk-in shower with multiple shower heads and rain shower, stunning designer tile work, and an oversized walk-in closet. Three additional bedrooms, two fully updated bathrooms, and an oversized laundry room complete the second floor. Designed for both relaxation and entertaining, the backyard is a true showpiece featuring a newer pool with newer pool equipment a gas-heated pool and spa, outdoor kitchen with built-in grill, beverage refrigerator, TV, bar seating, ambient lighting, covered lanai, expansive paver patio, fully fenced, with redesigned landscaping and tranquil conservation views that provide a level of privacy rarely found in Central Florida. Significant recent improvements include a new tile roof installed in 2024, Two New HVAC Units (2026 & 2025), two new water heaters and newer pool & equipment offering both peace of mind and long-term value. Lake Roberts Landing features a community pier/dock onto Lake Roberts to enjoy the beautiful lake and fishing. Perfectly located just minutes from Winter Garden Village, Downtown Winter Garden, Windermere, Hamlin, A-rated schools (Lake Whitney Elementary, SunRidge Middle and West Orange High), premier shopping, dining, entertainment, SR-429, and Florida’s Turnpike, this exceptional residence offers the luxury lifestyle today’s buyers are searching for in one of Winter Garden’s most sought-after gated communities. A rare opportunity to own a fully updated luxury home with a private conservation lot, no rear neighbors, resort-style outdoor living, and an unbeatable Winter Garden location.

1812 Lake Roberts Landing Drive, Winter Garden

Listing courtesy of EXP REALTY LLC. 888-883-8509

$549,000
3 Beds 3 Baths O6415343 MLS
Looking for a move in ready home in Hamlin, Winter Garden with a spacious private backyard? Welcome to 6323 Hamlin Reserve Boulevard, a beautifully maintained 3 bedroom, 2.5 bathroom home offering 2,177 square feet of living space in the desirable Hamlin Reserve community. One of the standout features of this home is the expansive fenced backyard, offering exceptional outdoor space for entertaining, pets, play, or simply enjoying added privacy. A covered brick paver patio creates a comfortable extension of the living space and an ideal setting for relaxing or gathering with family and friends. Inside, the home features a completely carpet free interior with wood look tile and luxury vinyl flooring throughout. The kitchen offers black cabinetry, quartz countertops, stainless steel appliances, and an open layout that connects naturally with the living and dining areas. Large windows bring in abundant natural light, creating a bright and inviting atmosphere. Upstairs, the spacious primary suite includes a walk in closet and private bathroom. Two additional bedrooms provide flexibility for family, guests, or a dedicated home office. The property also includes a 2 car garage and practical storage throughout. Living in Hamlin Reserve means being surrounded by the convenience and lifestyle that make this area of Winter Garden so desirable. The community offers a pool, park, and playground, while the home is just minutes from Hamlin Town Center, SR 429, shopping, restaurants, entertainment, medical facilities, and everyday conveniences. The property is currently zoned for Independence Elementary, Bridgewater Middle, and Horizon High School.

6323 Hamlin Reserve Boulevard, Winter Garden

Listing courtesy of WRA BUSINESS & REAL ESTATE. 407-512-1008

$569,000
4 Beds 4 Baths O6415777 MLS Toll Brothers BLDG.
Under Construction. Toll Brothers New Construction in Horizon West – Estimated Completion Summer 2026 - Beautiful new townhome featuring a rare detached garage with a private in-law suite above, perfect for guests, multigenerational living, or a home office. The covered entry opens to a spacious foyer and guest suite. The open-concept living area includes a gourmet kitchen with breakfast bar, dining area, and great room with access to the private courtyard. The primary suite offers a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet. Located in desirable Horizon West near shopping, dining, top-rated schools, and major roadways. A unique floor plan your clients won't want to miss! Estimated completion Summer 2026.

12732 Sunset Walk Drive, Winter Garden

Listing courtesy of ORLANDO TBI REALTY LLC. 407-345-6000

$850,000
4 Beds 4 Baths O6414802 MLS
FULLY FURNISHED!! Welcome to the home you've been waiting for in the highly desirable Hamlin Reserve community by Ashton Woods! This beautifully fully furnished 4-bedroom, 3.5-bath residence offers 3,103 square feet of thoughtfully designed living space and is truly move-in ready. Featuring premium flooring throughout, an open-concept layout, and a gourmet kitchen with a large quartz island and high-end stainless steel appliances, this home perfectly blends style and functionality for modern living. The spacious primary suite provides a private retreat, while three additional bedrooms with plenty of room for family and guests. Step outside to the covered lanai and private backyard, ideal for enjoying your morning coffee or hosting weekend gatherings. All appliances are included, making your transition effortless. Located in the sought-after Hamlin Reserve, residents enjoy a low HOA of just $140/month, which includes access to the community pool, playground, clubhouse, and dog park—with NO CDD fees. One of the community's greatest advantages is its walkability to Hamlin Town Center, where you'll find Publix, PopStroke, coffee shops, restaurants, shopping, and entertainment just a short stroll away. Conveniently situated near SR-429, Historic Downtown Winter Garden, Walt Disney World, and zoned for A-rated Horizon West schools, this exceptional home offers the perfect combination of luxury, location, and lifestyle. Don't miss this opportunity—schedule your private showing today!

6460 Makrut Lime Drive, Winter Garden

Listing courtesy of WRA BUSINESS & REAL ESTATE. 407-512-1008

$790,000
5 Beds 4 Baths O6415123 MLS
Welcome to 7687 Bowery Dr, located within the highly desirable, master-planned Ravenna community of Horizon West. This single-story masterpiece offers a rare combination of upscale lifestyle flexibility and long-term value, situated on an expansive 0.48-acre premium lot—one of the largest in the entire community! With NO REAR NEIGHBORS, a serene conservation backdrop, and nightly views of spectacular theme park fireworks right from your own property, this home is a true sanctuary. Grand 8-foot double front doors welcome you into a masterfully crafted, light-filled layout boasting 5 bedrooms, 4 full bathrooms, and over 3,170 square feet of high-end living space. INTERIOR HIGHLIGHTS: Designed for both grand entertaining and comfortable everyday living, the main areas showcase stunning 8"x36" designer tile flooring. NO CARPET: The home features durable tile and waterproof luxury vinyl plank flooring throughout for ultimate ease of maintenance. At the heart of the residence is a chef’s dream kitchen, anchored by a massive 11-foot center island with seating for five. It comes fully equipped with 42" light gray cabinetry with crown molding, gleaming white quartz countertops, premium stainless steel appliances, double wall ovens, and a drop-in cooktop. THOUGHTFUL FLOOR PLAN FLEXIBILITY: The luxurious primary suite serves as a true retreat, featuring elegant tray ceilings, dual walk-in closets, and a spa-like 5’x8’ frameless glass shower with dual shower heads. For maximum functionality, the layout features a Jack-and-Jill bathroom between bedrooms 2 and 3, plus a private en-suite bathroom for bedroom 5—making it perfectly optimized as a multi-generational retreat or a private guest wing. OUTDOOR OASIS & PEACE OF MIND: Step outside to your massive backyard looking out directly over a protected conservation area, providing unparalleled privacy and beautiful natural views. The neighborhood offers premium community amenities including a pool and playground, all with low HOA fees and NO CDD! PRIME LOCATION: Perfectly positioned in Winter Garden, you are zoned for top-rated public schools and sit just minutes from Hamlin Town Center shopping, dining, and major transport corridors (429, 408, and Florida’s Turnpike). Enjoy a swift, seamless commute to downtown Orlando, Disney World, and Universal Studios. Schedule your private showing today and discover the ultimate Central Florida lifestyle!

7687 Bowery Drive, Winter Garden

Listing courtesy of LA ROSA REALTY ORLANDO LLC. 407-900-5003

$370,000
3 Beds 3 Baths S5151359 MLS 00 BLDG.
Well keep and move in ready corner unit townhouse at the beautiful signature lake at winter garden ,brand new vinyl plank floor at the first floor this 3 bedroom and 2.5 bath room townhouse have 1750 sqft and feature big court yard between the garage you can enjoy the outdoors living on the big courtyard , the oversize front porch is welcome to their new owner , the first floor feature all ceramic title ,have living room and the work space at the front the house and the the kitchen offer gorgeous granite counter tops , wood cabinet and pendant lighting , open up the family room , also have powder room at the first floor , upstair you have 3 bedroom big walk in closet at the master bedroom and dual sink at the master bathroom and one more full bath to share for the other bedroom , signature lake is sought after community at winter garden , feature resort style pool and state of the art gym and club house many event for the residence for the community , grade A school . it is close located next to the Hamlin shopping center and the winter garden village close to 429 and 535 , the HOA fee include cable include HBO and high speed internet from sepcturm . , this is turn key townhouse is ideal for who enjoy low maintenance lifestyle .

14903 Driftwater Drive, Winter Garden

Listing courtesy of NUMBER 1 BROKER, LLC. 407-566-3400

$1,450,000
6 Beds 6 Baths O6414639 MLS
An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the ground floor of the home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.

16614 Harbor Sail Way, Winter Garden

Listing courtesy of GLOBAL FLORIDA REALTY. 407-387-3030

$870,000
4 Beds 5 Baths O6413972 MLS
Nestled within the prestigious gated enclave of Bay Isle, this distinguished Toll Brothers home offers a rare combination of sophisticated design, thoughtful craftsmanship, and resort-caliber amenities — all within walking distance of Winter Garden Village and AdventHealth. A soaring two-story foyer and grand living room welcome you with an abundance of natural light streaming through an exceptional array of windows — a hallmark of the home's open, airy character. At the heart of the home lies a commanding gourmet kitchen, completely updated in 2021 with quartz countertops, a handsome marble backsplash, and a professional-grade induction cooktop with custom hood vent. Rich cherry cabinetry, a wall oven, built-in microwave, generous center island, and extensive counter space are all finished with elegant crown molding — flowing seamlessly into the expansive family room with French doors opening to the outdoor living area. The main-level primary suite is a true sanctuary, featuring rich laminate flooring, serene pool and spa views, and architectural transom windows that elevate the abundant natural light. Two oversized walk-in closets with custom built-in organization systems flank a luxurious en-suite bath complete with a dual-sink vanity, deep soaking tub, and a spa-inspired walk-in shower. Upstairs, three additional bedrooms offer both privacy and connection. A private en-suite bedroom with generous walk-in closet is discreetly separated via a catwalk, while two additional bedrooms share a well-appointed Jack-and-Jill bath with individual vanity areas and a shared water closet and tub/shower. Your private home theater is fully equipped for the ultimate cinematic experience — theater seating, a 4K HD projector, Dolby surround sound, all convey with the home. The space also offers flexibility as a fifth bedroom. A loft game area and additional half bath complete the upper level's entertainment suite. Step outside to your private oasis: a sparkling pool and spa enclosed within an oversized screened lanai, complete with an outdoor shower and multiple seating areas ideal for effortless outdoor entertaining. An additional state of the art Clearlight 2 person infrared sauna provides relaxation, and rejuvenation. A three-car split garage — two bays connected to the main home, a third independently accessed — provides exceptional versatility for a workshop, boat storage, collector vehicles, or extra storage. A dedicated EV charging station is already in place. Eight-foot interior doors and extensive crown molding throughout reinforce the home's refined aesthetic. New roof (2019) · Pool pump (2018) · Full kitchen renovation (2021) Bay Isle's gated grounds feature a park, playground, walking trail, and a fishing pier on Black Lake — offering a tranquil, connected lifestyle just minutes from major roadways and every amenity Winter Garden has to offer.

14411 Hampshire Bay Circle, Winter Garden

Listing courtesy of STOCKWORTH REALTY GROUP. 407-909-5900

$435,000
3 Beds 3 Baths O6414015 MLS Na BLDG.
Welcome to 6131 Elfin Herb Way, a beautifully maintained home offering comfort, functionality, and a desirable location. Situated on a prime corner lot, this inviting residence features a spacious and thoughtfully designed floor plan with abundant natural light throughout. At the heart of the home, you will find a cute, private courtyard tucked between the main house and the garage, the perfect unique spot for relaxing or enjoying your morning coffee. The well-appointed kitchen flows seamlessly into the living and dining areas, creating an ideal space for everyday living and entertaining. The primary suite provides a private retreat, while the additional bedrooms offer flexibility for family, guests, or a home office. Its amenities include a beach-style pool, cabana, dog park, playground, and nature gardens. Hamilton Gardens is conveniently located near Hamlin Town Center, restaurants, and shopping. Conveniently located in the heart of Hamlin, the most desirable area of Horizon West, you are just minutes away from shopping, dining, top-rated schools, major roadways, and local attractions. Don't miss this opportunity to own a wonderful home in a sought-after community. Schedule your private showing today!

6131 Elfin Herb Way, Winter Garden

Listing courtesy of FLORIDA CONNEXION PROPERTIES. 407-574-2636

$844,000
4 Beds 4 Baths O6414274 MLS
Under Construction. NEARLY COMPLETE! Near Walt Disney World Theme Parks! Welcome to the Eliot plan, a luxurious new home offering a perfect blend of elegance, comfort, and functionality with 4 spacious bedrooms, 3.5 bathrooms, and an expansive loft and home office area. This home features a stunning exterior design and is designed to enhance both style and livability, showcasing a covered front porch and a covered backyard lanai - perfect for outdoor relaxation and entertaining. Step into the extended entryway, which leads to a versatile home office area, offering the perfect space for productivity or leisure. The heart of this home is the chef-inspired kitchen, complete with a large island and premium stainless-steel appliances, including an electric cooktop, built-in oven/microwave combo, dishwasher, and vent hood. The luxurious primary suite is located on the first floor for ultimate convenience and privacy. Upstairs boasts an extended loft that provides an excellent space for lounging as well as three secondary bedrooms - one with its own ensuite! Additional features include an 8-foot front door and 8' doors on the 1st floor, upgraded flooring throughout, ample storage closets, and a new home warranty for peace of mind. Call today to schedule a tour!

17434 Honeybell Tangelo Court, Winter Garden

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC. mls@oerfl.com

$1,020,000
4 Beds 3 Baths O6413659 MLS
Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!

20 E Division Street, Winter Garden

Listing courtesy of CHARLES RUTENBERG REALTY ORLANDO. 407-622-2122

$839,000
5 Beds 5 Baths O6412120 MLS
One or more photo(s) has been virtually staged. Welcome to one of the most beautifully designed homes in Horizon West, nearly 3700 square feet of luxury living space, and only 4 minutes from Disney World, Firework views nightly. This house is a MUST SEE. The open-concept floor plan includes an expansive great room that flows seamlessly to the covered lanai and spacious backyard. Perfectly positioned to capture breathtaking sunset views over open farmland. There is plenty of room to build your dream pool, and there are no rear neighbors! Built less than 2 years ago, this exceptional 5-bedroom, 4.5-bath residence offers spacious rooms, stunning modern farmhouse finishes throughout, and ample storage (a premium in Florida). From the moment you step inside, the home delivers an unforgettable WOW factor. Anchored by an oversized island and a designer gourmet kitchen with a gas range for any chef’s delight. The stellar floor plan features premium cabinetry, quartz countertops, and premium fixtures. There are three ensuite bedrooms, including a spacious primary suite, plus two secondary ensuite spaces. One of these ensuite spaces is conveniently located downstairs, making it ideal for guests or multigenerational living. Community amenities include: Pool, Splash Pad, Playground, Hiking & Biking Trails. Perfectly situated in the heart of Horizon West, this home is within walking distance of Flamingo Crossings shopping and dining, and the brand-new Ovation Elementary School. Convenient access to Hamlin, downtown Winter Garden, MCO, major roadways, shopping, dining, and entertainment make this location truly hard to beat. A rare combination of design, quality, functionality, views, and proximity to Disney. This is Central Florida luxury living at its best!

15652 Gentle Rain Drive, Winter Garden

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

$669,500
4 Beds 3 Baths O6413773 MLS
Welcome to the home you've been waiting for! This stunning 4-bedroom, 3-bathroom residence offers the perfect combination of modern design, thoughtful upgrades, and everyday comfort. From the moment you arrive, you'll appreciate the charming front patio and inviting curb appeal that make this home stand out from the rest. Step inside and be greeted by gorgeous custom wainscoting in the entryway, creating an elegant first impression and setting the tone for the stylish finishes found throughout the home. The open-concept floor plan is designed for effortless entertaining and everyday living, offering a bright and spacious atmosphere that immediately feels like home. At the heart of the home is an impressive kitchen featuring stainless steel appliances, a large walk-in pantry, abundant cabinetry, and a stunning designer island with a contrasting cabinet color that adds character, sophistication, and a custom-built feel. The kitchen seamlessly overlooks the dining and living areas, creating the perfect space for gathering with family and friends. The private owner's suite is thoughtfully situated at the rear of the home, providing a peaceful retreat. The spacious ensuite bathroom features dual vanities, a large walk-in shower, and an oversized walk-in closet designed to accommodate all your storage needs. The additional bedrooms and bathrooms offer flexibility for family, guests, or a home office, while the professionally converted garage flex space, complete with flooring and air conditioning, provides endless possibilities as a gym, game room, media room, office, homeschool room, or bonus living area. Designer touches continue throughout the home, including a beautiful modern accent wall in the dining room and upgraded lighting fixtures above both the dining area and kitchen island, adding warmth, style, and elegance throughout. Step outside to your enclosed lanai and FULLY FENCED IN backyard, perfect for entertaining, pets, playtime, or simply relaxing and enjoying Florida's beautiful weather. As an added bonus, the HOA includes landscaping, allowing for truly low-maintenance living. Beyond the home itself, you'll fall in love with the incredible resort-style amenities this sought-after community has to offer, including multiple pools, fitness centers, tennis courts, sand volleyball courts, playgrounds, scenic walking trails, and a vibrant calendar of community events throughout the year. Everyday conveniences are just a golf cart ride away, including Publix, Jersey Mike's, a nail salon, Kiddie Academy, and the soon-to-open Fifth Third Bank. This golf cart-friendly community was designed to make life easy, fun, and connected. Located in the highly desirable Horizon West area and zoned for Atwater Bay Elementary, you'll be just minutes from shopping, dining, entertainment, and outdoor recreation. Enjoy the charm of historic Downtown Winter Garden, the scenic West Orange Trail, and easy access to Orlando's world-famous attractions and theme parks. This home offers more than just beautiful living spaces, it offers a lifestyle. Why wait to build when you can move right into a home filled with upgrades and start enjoying everything Horizon West has to offer today? Schedule your private showing before this incredible opportunity is gone!

9717 Waterway Passage Drive, Winter Garden

Listing courtesy of LIFESTYLE INTERNATIONAL REALTY. 305-809-8085

$499,000
4 Beds 3 Baths O6413534 MLS Toll Brothers BLDG.
Under Construction. Toll Brothers New Construction. Our beautiful Rinker Corner unit townhome offers 2,031 square-feet, 4 bedrooms and 3 bathrooms plus loft. Upon entering the inviting foyer, you will find a spacious downstairs bedroom perfect for guests or office space. Leading to a bright kitchen and great room. The stunning kitchen is highlighted by a designer backsplash, modern cabinets, and upgraded countertops. With free-flowing space between the kitchen, great room and the casual dining area this townhomes offers the perfect open-concept living space. Secluded on the second floor is the primary bedroom, complete with a large walk-in closet, loft perfect for a second TV space and two additional secondary bedrooms that share a full bathroom. Additional highlights include a rear courtyard area, and a detached 2-car garage. The future resort-style amenities in this community will make your family feel they're on vacation year-round. Schedule an appointment today to see it for yourself! Closing cost assistance available.

13861 Easdale Alley, Winter Garden

Listing courtesy of ORLANDO TBI REALTY LLC. 407-345-6000

$539,000
4 Beds 3 Baths O6413517 MLS Toll Brothers BLDG.
Under Construction. Toll Brothers New Construction. Our beautiful Autumn townhome offers 1,897 square-feet, 4 bedrooms and 3 bathrooms. Upon entering the inviting foyer, you will find a spacious downstairs bedroom perfect for guests or office space. Leading to a bright kitchen and great room. The stunning kitchen is highlighted by a designer backsplash, modern cabinets, and upgraded countertops. With free-flowing space between the kitchen, great room and the casual dining area this townhomes offers the perfect open-concept living space. Secluded on the second floor is the primary bedroom, complete with a large walk-in closet and two additional secondary bedrooms that share a full bathroom. Additional highlights include a rear courtyard area, and a detached 2-car garage. The resort-style amenities in this community will make your family feel they're on vacation year-round. There's still time to personalize this home with your preferred design upgrades.

12808 Sunset Walk Drive, Winter Garden

Listing courtesy of ORLANDO TBI REALTY LLC. 407-345-6000

$249,950
2 Beds 2 Baths O6411162 MLS 200 BLDG.
One or more photo(s) has been virtually staged. HOA fee includes cable, internet, water, sewer, trash, pool and exterior maintenance. Welcome to this well maintained 2-bedroom, 2-bath condominium offering 1,276 square feet of comfortable living space in a gated, resort-style community. The open-concept floor plan is perfect for everyday living and entertaining, featuring granite countertops, spacious living areas, abundant natural light throughout, and a versatile den that is ideal for a home office, reading space, or additional flex area. The community features an outstanding selection of amenities, including a serene pool and spa, fitness center, indoor basketball court, racquetball court, playground, outdoor grilling areas, and a beautifully appointed clubhouse complete with a movie room, pool table, business workspace, and a children's play area for added convenience while working out. Ideally located just minutes from Winter Garden Village, Historic Downtown Winter Garden, and major highways, this condo offers the perfect combination of comfort, convenience, and easy access to everything the area has to offer. Whether you're looking for a primary residence, seasonal retreat, or investment opportunity, this condo is a must-see!

200 Southern Pecan Circle Unit 206, Winter Garden

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

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