Location: Winter Garden
Do Not Show Listings
15527 SWEET ORANGE AVE, WINTER GARDEN, FL 34787
$700,00020 Days on yellowkey MLS ID: O6394429
Bed: 3 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2383 Built: 2017Monthly Fee: $118 Tax: $5,959 (2025)Community: Highlands/Summerlake Grvs Ph 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,959
Elementary School: Summerlake Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: Experience refined living in this truly one-of-a-kind single-story residence, offering over 2,300 square feet of thoughtfully designed space. This exceptional home features three spacious bedrooms, three full bathrooms, and an additional half bath, along with a private office or den enclosed by elegant French doors—perfect for working from home or quiet retreat. Designed for both comfort and sophistication, the home boasts soaring 10-foot ceilings and striking tray ceilings in the foyer, great room, and primary suite. The open-concept living area is enhanced by extended tile flooring, creating a seamless and upscale feel throughout. At the heart of the home, the gourmet kitchen impresses with a large center island, stylish pendant lighting, and effortless flow into the main living and dining spaces. Enjoy the best of indoor-outdoor living with two screened-in lanais—one just off the kitchen and the other connected to the family room—accessible through dual sets of sliding glass doors. Home features tankless gas water heater, gas range and outdoor gas hookup for grilling. Additional highlights include a rare tandem three-car garage, a functional drop zone with built-in cabinetry and counter space, and charming curb appeal with a welcoming front porch—perfect for relaxing with your favorite drink. Nestled in the highly sought-after Horizon West area of Winter Garden, this home offers unmatched convenience. You’re just minutes from Walt Disney World, premier shopping and dining, Orange County National Golf Center, and the charm of Historic Downtown Winter Garden. With easy access to major highways including 429, I-4, and the Florida Turnpike, commuting is effortless. Residents enjoy access to outstanding community amenities, including a resort-style pool, playgrounds, dog park, tennis courts, and more. Whether you’re searching for a primary residence, vacation home, or investment opportunity, this property offers the perfect blend of luxury, functionality, and location.
Listing is courtesy of: BUYER REBATES REALTY (407-629-2300)
Listing Agent: Sean Popat (407-399-1669)
10224 ATWATER BAY DR, WINTER GARDEN, FL 34787
$799,0004 Days on yellowkey MLS ID: S5147252
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3227 Built: 2018Monthly Fee: $230 Tax: $7,456 (2025)Community: Waterleigh Ph 2BSingle Family
Taxes:$7,456
Elementary School: None
High School: None
Middle School: None
Remarks: Stunning home located in the highly desirable Winter Garden area, offering a modern and spacious floor plan designed for comfortable living and entertaining. This beautifully maintained property features bright open living spaces, a stylish kitchen with ample cabinetry, and generously sized bedrooms. Enjoy a private outdoor area perfect for relaxing or hosting gatherings. Conveniently located near top-rated schools, shopping, dining, major highways, and just minutes from Downtown Winter Garden, Hamlin Town Center, and Disney attractions. An exceptional opportunity to enjoy luxury, location, and lifestyle in one of Central Florida’s most sought-after communities.
Listing is courtesy of: NAIM REAL ESTATE LLC (818-268-9917)
Listing Agent: Samir Naim (818-268-9917)
15408 LEBEAU LOOP, WINTER GARDEN, FL 34787
$580,00057 Days on yellowkey MLS ID: O6383534
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2415 Built: 2022Monthly Fee: $101 Tax: $7,566 (2024)Community: Winding Bay Ph 3Single Family
Taxes:$7,566
Tax Year: 2024
Remarks: Discover the ease of low-maintenance living in Horizon West’s Winding Bay with this 2022- built home. No CDD. Low HOA. And a layout that actually works for real life. Winding Bay offers resort-style amenities including a clubhouse, pool, and dog park, and you’re zoned for Water Spring Elementary and Middle plus Horizon High. The location is what continues to drive demand here: you’re right in the heart of Horizon West, close to everything that makes this area so desirable. Inside, the floor plan is practical and well thought out. The main living area is open and bright, connecting seamlessly to the kitchen with a large island, gas range, quartz counters, stainless appliances, and subway tile backsplash. Clean finishes. Functional space. Nothing wasted. The primary suite is downstairs with tray ceilings, a custom walk-in closet, and a well-appointed bath with dual vanities and a beautifully tiled shower. Laundry is also on the first floor, exactly where it should be. Upstairs, a loft with built-in desk space anchors three generously sized bedrooms and a shared bathroom. It’s a great setup for keeping sleeping spaces separate from the main living area. Outside, you have a covered lanai, vinyl-fenced yard, and alley access to the two-car garage, which keeps the front elevation clean and charming. You’re minutes from Hamlin Town Center, Flamingo Crossings, Disney, dining, golf, shopping, and major highways for easy beach access. If you’re looking for newer construction, smart layout, and strong location in Horizon West, this one is worth a look.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
15306 LEBEAU LOOP, WINTER GARDEN, FL 34787
$568,00055 Days on yellowkey MLS ID: O6384014
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2482 Built: 2021Monthly Fee: $101 Tax: $6,339 (2024)Community: Winding Bay Ph 3Single Family
Taxes:$6,339
Remarks: Tucked on a corner homesite in one of Winter Garden’s most sought-after communities, 15306 Lebeau Loop offers the space and layout so many buyers are searching for. Featuring 4 bedrooms, 2.5 bathrooms, and 2,482 square feet. The first-floor primary suite is privately situated at the rear of the home, creating a true retreat with direct access to the expansive lanai and charming courtyard. The en suite bathroom features dual sinks, granite countertops, and a generous walk-in closet. The main living space has an inviting farmhouse feel, highlighted by luxury vinyl plank flooring throughout the living areas, white cabinetry, and granite countertops in the kitchen. Designed with storage in mind, the kitchen includes a walk-in pantry as well as a coffee nook, providing the extra prep and organization space that makes a difference. While the community is natural gas, this home is equipped with an induction stove for precise, modern cooking. Upstairs, you’ll find three additional bedrooms and a spacious loft that opens to a private balcony, the perfect spot to catch breezy evenings and Florida sunsets. Whether used as a secondary living area, media room, or home office, the loft adds valuable flexibility to the layout. Additional upgrades include a water filtration system, professional window tint, and blinds already in place, making this home truly move-in ready. Located near the neighborhood playground, park, and play field, this home combines a prime corner location with convenient access to community amenities, all just minutes from the best of Winter Garden and, of course, the Disney Parks. ADT alarm system installed: 24 hr monitor for fire and alarm. Also ADT 6 outdoor camera continuous record with monitor.
15716 SWEET LEMON WAY, WINTER GARDEN, FL 34787
$739,00086 Days on yellowkey MLS ID: O6375190
REDUCED by $26,000 (3.4%) on 04/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2945 Built: 2021Monthly Fee: $118 Tax: $9,510 (2025)Community: Highlands At Summerlake GrovesSingle Family
Taxes:$9,510
Remarks: Beautiful two-story single-family home located in the highly desirable Winter Garden area, featuring a welcoming front porch perfect for morning coffee. This well-maintained residence offers 2,945 sq ft of heated living space with quality flooring, excellent finishes, and tasteful details throughout. The open-concept main level showcases a spacious living area with a custom accent wall and wood panel detailing, flowing seamlessly into the kitchen and dining spaces. The kitchen features elegant cabinetry and appliances, a large pantry, and a generous island ideal for everyday living and entertaining. A stylish powder room and thoughtfully customized laundry room with utility sink add convenience to the main floor. Upstairs, a large loft provides a versatile second living area, ideal for a media room, study, or additional work-from-home space. In addition to the primary suite, the home offers multiple flexible rooms currently well-suited for home offices, a playroom, or guest accommodations, supporting today’s modern lifestyle. The primary suite includes dual vanities and a beautifully finished walk-in shower. The fully fenced backyard offers privacy and ample space for outdoor enjoyment, complemented by a covered rear patio perfect for relaxing or hosting gatherings. Additional highlights include a garage with built-in storage and organization systems. Located in a deed-restricted community with resort-style amenities, including a community pool, playground, and sidewalks, and conveniently close to shopping, dining, top-rated schools, and major roadways. This home offers the ideal blend of comfort, functionality, and location. Schedule your private showing today.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Any Alves (407-455-0618)
9256 GRAND ISLAND WAY, WINTER GARDEN, FL 34787
$750,0006 Days on yellowkey MLS ID: O6397917
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2507 Built: 2017Monthly Fee: $164 Tax: $6,475 (2025)Community: Watermark Ph 2CSingle Family
Taxes:$6,475
Elementary School: Panther Lake Elementary
Remarks: Welcome to Watermark in Winter Garden one of the most sought-after, resort-style communities in Horizon West. This energy-efficient Meritage home has 4 bedrooms, 2.5 baths, and a super functional layout with high ceilings and great natural light throughout. As soon as you pull up, you’ll notice the stone accents on the exterior, brick paver driveway, and clean curb appeal. Inside, the home has been freshly painted and updated with new luxury vinyl plank flooring upstairs, giving it a modern feel without the maintenance headaches. The layout just makes sense 3 bedrooms and a versatile loft upstairs (perfect for a media room, office, or playroom), and a 4th bedroom downstairs that works great for guests or a private home office. The open-concept kitchen seamlessly connects to the main living area and features granite countertops, ample cabinetry, and an easy flow out to the backyard making it ideal for everyday living or having people over. Out back is where this one really stands out. If you're looking for a backyard oasis, look no further. This home has no rear neighbors backing to a retention pond and conservation beyond that. The pool deck is over 1300 square feet with a heated 6 foot deep 484 square foot custom saltwater pool! Enjoy sunsets, watching Disney fireworks at night or the occasional rocket launch in the distance! It’s a great setup for relaxing or entertaining. Watermark has some of the best amenities around resort-style pool, splash pad, gym, clubhouse, tennis, basketball, dog park, and tons of walking and biking trails. You’re also within walking distance to restaurants and just a short drive to Disney, shopping, and everything Winter Garden and Horizon West have to offer. If you’re looking for a clean, move-in ready home in a great location with a strong lifestyle, this one checks all the boxes!
Listing is courtesy of: DENIZ REALTY PARTNERS LLC (407-704-0780)
Listing Agent: Chris Courtney (407-406-0506)
5596 THOMAS SQUARE DR, WINTER GARDEN, FL 34787
$618,00045 Days on yellowkey MLS ID: O6386791
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2458 Built: 2015Monthly Fee: $324 Tax: $8,569 (2025)Community: Overlook At HamlinSingle Family
Taxes:$8,569
Remarks: Welcome to this beautiful 4-bedroom, 3.5-bath home in the highly sought-after Overlook at Hamlin community of Winter Garden. Ideally positioned with a serene front lake view, this well-maintained residence offers over 2,400 square feet of thoughtfully designed living space. The open-concept floor plan features a spacious kitchen overlooking the main living and dining areas, perfect for everyday living and entertaining. Upstairs, the generous primary suite and additional bedrooms provide comfort and privacy for the whole family. Enjoy outdoor living from the rear patio and the convenience of nearby Hamlin Town Center shopping, dining, parks, and top-rated schools, with easy access to FL-429. A wonderful opportunity to own in one of Winter Garden’s most desirable communities.
Listing is courtesy of: XCELLENCE REALTY INC. (866-595-6025)
Listing Agent: Phoebe Yu (407-446-7588)
8275 BAYVIEW CROSSING DR DR, WINTER GARDEN, FL 34787
$565,0006 Days on yellowkey MLS ID: TB8496196
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2019 Built: 2017Monthly Fee: $312 Tax: $5,109 (2025)Community: Waterleigh Phase 1CSpa: YesSingle Family
Taxes:$5,109
Middle School: Water Spring Middle
Remarks: **New landscaping in progress with pictures to follow, expected by April month end** Welcome to Waterleigh Phase 1 in Horizon West, Winter Garden, one of the most desirable communities in the area, known for resort-style amenities, scenic lakes, and top-rated schools. This rare one-story Arbor floor plan offers an open-concept layout with a highly sought after private fenced backyard - perfect for relaxing, entertaining, and enjoying Florida living at its best. This home features an extended screened-in lanai & patio upgrade, private backyard with a hot tub, cozy electric fireplace, dedicated home gym space, tandem 3-car garage, fresh exterior and interior paint. This home is move-in ready with thoughtful upgrades. Minutes from Hamlin Town Center, shopping, dining, and entertainment, plus quick access to Disney and major highways. Please schedule a showing to come view this rare opportunity to own a single-story home in Waterleigh Phase 1.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Timothy Shepard (727-204-9618)
238 N MAIN ST, WINTER GARDEN, FL 34787
$600,0008 Days on yellowkey MLS ID: O6397340
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1005 Built: 1950 Tax: $5,389 (2025)Community: Orange Grove SubSingle Family
Taxes:$5,389
Elementary School: Dillard Street Elem
High School: West Orange High
Middle School: Lakeview Middle
Remarks: **** HEART OF DOWTOWN WINTER GARDEN **** CAN'T GET MUCH CLOSER TO ***HISTORIC DOWNTOWN WINTER GARDEN *** THAN THIS! SERIOUSLY! FRESH OWNER REDO WITH DISCERNING DESIGN CHOICES ON THIS SOLID & ADORABLE 3 BEDROOM/2 BATH FENCED YARD (SOLID CONCRETE BLOCK) CHARMER. *** NO HOA OR FEES*** HOOOORAY! & WITHIN STEPS TO DOWNTOWN PLANT STREET, TONY'S, HARLOW GROVE RESTAURANT, CHURCHES, FARMERS MARKET, CROOKED CAN FOOD HALL, JESSIE BROCK COMMUNITY PARK, PUBLIC BOAT RAMP AT NEWTON PARK, AND ALL THAT FAST GROWING DOWNTOWN HISTORIC WINTER GARDEN HAS TO OFFER!!! AMAZING CHANGES ARE ON THE HORIZON!!!----GET IN ON YOUR OWN LOCKED IN LOCATION NOW!!!----- (LOCATED WITHIN THE ZONED GOLF CART DISTRICT). WITHIN MINUTES TO HWY 50, FOWLER GROVES/LOWES/TARGET & 429 FREEWAY ENTRANCE, AS WELL AS FLORIDA TURNPIKE AND E-W EXPRESSWAY ENTRANCES BEING MERE MINUTES AWAY ON EAST PLANT STREET; OH SO CENTRALLY LOCATED DIRECTLY IN "TOWN PROPER" JUST A FEW LOTS UP FROM PLANT STREET; & JUST A LITTLE FURTHER DOWN MAIN STREET AND YOU ARE AT THE PUBLIC BOAT RAMP, NEWTON PARK AND THE FARNSWORTH CITY POOL!!! BEYOND EXCELLENT ACCESS TO MULTIPLE GROCERIES, TAILORS & SHOPPING OPTIONS AT HWY 50, PARK AVENUE, DILLARD STREET AND NEARBY OAKLAND! ALSO, THE WEST ORANGE TRAIL RUNS PERPENDICULAR TO MAIN STREET (YOUR STREET) & IS STEPS FROM YOUR HOME-----CONCRETE BLOCK CONSTRUCTION BUILT W/TERMITE BOND/MONTHLY PEST TREATMENT-ALL WITH MASSEY SENTRICON & TRANSFERABLE BOND TO THE NEW OWNER--- HOME HAS GROOMED MATURE OAKS WITH FENCED IN BACK YARD (WOOD PLANK AND VINYL) WITH ELEVATED WOOD DECK FOR FLIPPING OPEN THE BRAND NEW DOUBLE FRENCH DOORS AND ENJOYING FOR ENTERTAINING!!! ***EXCELLENT VALUE/EXCELLENT LOCATION/GOLF CART DISTRICT/NO HOA!***--WHY RENT WHEN YOU CAN (OWN) YOUR OWN PROPERTY FOR JUST A FEW BUCKS MORE PER MONTH? -----HOME WARRANTY OPTIONS AVAILABLE. WITHIN ZILLOW RANGE PRICING! GREAT DEAL. COME SEE FOR YOURSELF...........
Listing is courtesy of: FOLIO REALTY LLC (407-917-0241)
Listing Agent: Jason Fulmer (321-303-6670)
2621 SHIREHALL LN, WINTER GARDEN, FL 34787
$500,00041 Days on yellowkey MLS ID: O6386585
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 2003Monthly Fee: $243 Tax: $3,181 (2024)Community: Stoneybrook West Ut 04 48 48Spa: NoSingle Family
Taxes:$3,181
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bath home nestled in a 24 hour guard-gated golf community offering resort-style living. Enjoy tranquil mornings from the screened lanai overlooking a serene pond, creating the perfect setting for relaxation or entertaining. The thoughtfully designed floor plan features spacious living areas, abundant natural light, and comfortable bedrooms ideal for both everyday living and guests. The spacious primary suite has a beautiful water view with ensuite having dual sinks, garden tub and walk in shower. This spilt bedroom plan adds to the convenience of privacy, noise reduction and efficient space management. The open Kitchen overlooks the family room and has a breakfast area with center island and granite countertops. The interior has just been painted first of March, New water heater 4/2026. Residents enjoy access to an impressive array of amenities, including a championship golf course, clubhouse, resort-style pool, fitness center, tennis and pickleball courts, walking and biking trails, and an active social calendar. Conveniently located near shopping, dining, and entertainment, this home offers the perfect blend of comfort, security, and lifestyle. Please call for your showing today.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Barbara Waltman (407-616-2790)
1075 CHASE DR, WINTER GARDEN, FL 34787
$625,00045 Days on yellowkey MLS ID: O6386607
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2125 Built: 2015Monthly Fee: $41 Tax: $2,734 (2024)Community: Island Pointe SubSingle Family
Taxes:$2,734
Remarks: Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer-construction single-story home offers a blend of modern comfort and timeless style that’s sure to impress. As you enter, custom tile in the foyer sets the tone, with a versatile flex room to the right—perfect for a home office, formal dining room, playroom, or whatever suits your lifestyle.The open-concept design seamlessly connects the kitchen, dining, and family areas, creating an ideal space for entertaining. The large kitchen island is perfect for cooking, casual meals, or hosting friends and family. Sliding glass doors open to create an effortless indoor-outdoor living experience—perfect for those quintessential Florida days. The split floor plan offers privacy, with the primary suite serving as a true retreat, complete with high ceilings, a double vanity, and a spa-like shower. On the opposite side of the home, you’ll find three additional spacious bedrooms, each with plantation shutters and high end laminate flooring. After a long day, unwind on your fully screened back porch with space for multiple seating areas, or head to the side yard to tend your garden. The thoughtfully designed outdoor living space offers plenty of room for grilling, dining, and relaxing—an entertainer’s dream. Just minutes from your front door, Winter Garden’s vibrant Plant Street awaits, offering an award-winning farmer’s market, local dining, boutique shopping, art galleries, Crooked Can Brewery, the West Orange Trail, and year-round festivals.This is a rare opportunity to own a beautifully crafted home in one of Winter Garden’s most desirable neighborhoods—where modern living meets small-town charm. Call for your private showing today.
Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)
Listing Agent: Katie Bray (407-779-6677)
8216 TOPSAIL PL, WINTER GARDEN, FL 34787
$974,90030 Days on yellowkey MLS ID: O6391155
REDUCED by $14,100 (1.4%) on 04/13/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3055 Built: 2022Monthly Fee: $360 Tax: $12,728 (2025)Community: Lakeshore Preserve Ph 5Single Family
Taxes:$12,728
Remarks: Experience this beautifully upgraded home built by Toll Brothers, located in the highly desirable Lakeshore community. Perfectly positioned on a premium lot with no front or rear neighbors, this property offers both privacy and stunning surroundings. As you enter the home, you are welcomed by a dramatic two-story foyer highlighted by an elegant wood coffered ceiling, setting the tone for the spacious open concept design. The thoughtfully designed floor plan flows seamlessly into the formal dining area and expansive family room, creating the perfect space for entertaining and everyday living. The gourmet kitchen is a true centerpiece, featuring a large island ideal for gatherings, 42” cabinets with crown molding, stylish tile backsplash, natural gas cooktop, and stainless steel appliances. Just off the kitchen, the family room opens to a covered patio overlooking a private backyard with no rear neighbors, offering a relaxing outdoor retreat with hook ups for outdoor kitchen and sink. The primary suite, conveniently located on the first floor, features coffered ceiling, an upgraded spa-inspired en-suite bathroom, and a custom built walk-in closet. Upstairs, you’ll find a spacious loft with open railing overlooking the foyer below, along with three oversized bedrooms, each equipped with custom walk-in closets, providing comfort and ample storage for everyone. Beyond the home itself, the Lakeshore community offers an exceptional lifestyle with resort style amenities including a fitness center, gathering areas, sand volleyball court, fishing dock, and a spectacular resort style pool with splash area, along with many additional features. Conveniently located near shopping, dining, and top-rated schools, the property also provides easy access to major roadways leading to Walt Disney World Resort, Winter Garden Village, and the vibrant Hamlin area, known for its restaurants, shopping, and movie theater. Schedule your private showing today this exceptional property will not last long.
Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)
Listing Agent: Fiorella Dilorenzo (407-947-0832)
17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787
$718,79914 Days on yellowkey MLS ID: TB8493597
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2224 Built: 2026Monthly Fee: $84 Tax: $2,363 (2025)Community: Northlake/Ovation Ph 1Single Family
Taxes:$2,363
Remarks: Under Construction. This stunning Plant II single-family home is located in the desirable Northlake at Ovation community. This popular one-story, open-concept layout features 4 bedrooms and 3 bathrooms, ideal for modern living. With finishes from the AW Collection Sapphire vibrant blues meet bright whites for a bold look. Enjoy a chef-inspired kitchen with 42" cabinets, quartz countertops, and large island overlooking the living and dining areas, perfect for entertaining. The home also includes luxury vinyl flooring, a private primary suite with walk-in closet, a covered lanai for outdoor living, and a spacious 2-car garage. Conveniently located in Winter Garden near shopping, dining, major roadways, and top-rated schools. Community amenities include pool, clubhouse, playground areas and dog park.
Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)
Listing Agent: Reed Williams (813-918-4491)
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999178 Days on yellowkey MLS ID: O6353975
REDUCED by $100,001 (6.3%) on 04/13/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 3507 Built: 1953 Tax: $2,959 (2024)Community: J L Dillard Sub 3Single Family
Taxes:$2,959
Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter Garden. Blending timeless character with modern comfort, this property captures the essence of classic Florida living just steps from the West Orange Trail, Lake Apopka, and all the boutiques, restaurants, and entertainment that make Plant Street so special. Step inside and you’ll immediately sense the warmth and natural light that fill every corner of this inviting home. Soaring windows and panoramic glass doors create an airy, open atmosphere, seamlessly connecting the indoors with the lush, private grounds outside. The layout offers three spacious bedrooms and three bathrooms perfectly designed for both daily living and entertaining. The primary bedroom is highlighted with a relaxing hot tub, creating a private retreat within this charming home. At the heart of the home, the oversized living and dining areas flow effortlessly into the kitchen and outdoor spaces, ideal for hosting gatherings under the canopy of mature oaks. Every room feels bright and welcoming, and you’ll always be reminded that you’re just moments away from all the charm, energy, and convenience of Downtown Winter Garden — one of the most desirable small-town destinations in Florida. The property’s expansive outdoor footprint sets it apart — a dream for anyone who values space, privacy, and possibility. The triple lot provides ample room for future additions, a pool, or a garden oasis, while a grandfathered-in workshop offers incredible flexibility for hobbies, storage, or creative endeavors. An additional extended driveway offers generous space to accommodate 2–3 vehicles comfortably, with ample room for a boat, RV, or guest parking — a rare find in this highly sought-after downtown location. Whether you’re arriving by car or golf cart, convenience is unmatched. Enjoy the best of Winter Garden living with shopping, dining, the Farmers Market, Plant Street Market, and the Garden Theatre all within minutes, plus easy access to major highways for seamless commutes. From its timeless curb appeal and breathtaking natural light to its unparalleled location and lot size, this property represents a truly rare offering in one of Florida’s most beloved communities. Opportunities like this simply don’t come around twice. Come see for yourself why this remarkable downtown retreat isn’t just a home — it’s a legacy waiting to be continued.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
9849 LOST CREEK DR, WINTER GARDEN, FL 34787
$990,000511 Days on yellowkey MLS ID: O6258009
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3910 Built: 2021Monthly Fee: $250 Tax: $10,950 (2023)Community: WaterleighSpa: NoSingle Family
Taxes:$10,950
Elementary School: Water Spring Elementary
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. Big Price Reduction!!!!!! Nestled in the heart of Winter Garden’s prestigious Waterleigh community, this 5-bedroom, 4-bathroom masterpiece redefines modern luxury and family living. Boasting 3,910 sq. ft. of beautifully designed space, this 2021-built home is a perfect blend of timeless charm and contemporary convenience. From the moment you arrive, the immaculate landscaping and spacious 3-car garage set the stage for what lies within. Step onto the inviting front porch, and you’ll immediately feel at home. Inside, the gourmet kitchen takes center stage, showcasing gleaming white quartz countertops, custom 42-inch cabinets, and top-of-the-line stainless steel appliances. The oversized island is ready for anything—from morning coffee to lively dinner parties. Natural light floods the open living and dining spaces, where panoramic lake views create a serene backdrop for daily life. Retreat to the main-floor primary suite, a private haven with tranquil lake vistas, a spa-like ensuite, and a walk-in closet. Upstairs, a sprawling loft provides a perfect gathering space, while generously sized bedrooms ensure comfort for everyone. But the magic doesn’t stop indoors. Imagine unwinding on your covered patio as the sun sets, Disney’s iconic fireworks lighting up the sky above the lake. Beyond your doorstep, Waterleigh’s resort-style amenities await—scenic walking trails, sparkling pools, state-of-the-art fitness centers, and even a community garden. With its unbeatable combination of elegance, comfort, and convenience, this home offers more than just a place to live—it’s a lifestyle. Schedule your private tour today and start your next chapter in this extraordinary home!
Listing is courtesy of: REAL BROKER, LLC (407-279-0038)
Listing Agent: Jennifer Ibarra (213-500-7525)
12915 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$594,00066 Days on yellowkey MLS ID: O6381156
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2143 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Taxes:$2,326
Remarks: Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion July 2026. Single family Bungalow. This home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a master suite is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.
Listing is courtesy of: ORLANDO TBI REALTY LLC (407-345-6000)
Listing Agent: Devahn Powell (571-234-7236)
12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$548,00071 Days on yellowkey MLS ID: O6379918
5 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2062 Built: 2026Monthly Fee: $77 Tax: $2,326 (2025)Community: Westhaven At OvationSingle Family
Remarks: Under Construction. Under Construction. Toll Brothers New Construction in Horizon West – Winter Garden | Estimated Completion Summer 2026. This home is conducive for entertaining with its open floor plan. This home features a covered entry that leads to an open and expansive living space, kitchen, and dining. The home features covered lanai and a spacious courtyard with access to the detached 2 cars garage. The master bedroom is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet.
Listing Agent: Dayene Grubert (863-521-4474)
16140 HARBOR MIST ALY, WINTER GARDEN, FL 34787
$565,000133 Days on yellowkey MLS ID: O6365057
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2018Monthly Fee: $245 Tax: $8,615 (2025)Community: Waterleigh Ph 2ASingle Family
Taxes:$8,615
Remarks: Priced to sell — don't miss this beautifully maintained 2018-built Clearden model in the highly desirable Waterleigh community. Offering 2,477 sq ft, 4 bedrooms, and 3.5 bathrooms, this home is move-in ready with major updates already done. The open-concept main floor features a chef-ready kitchen with granite countertops, wood cabinetry, and stainless steel appliances, flowing into spacious living and dining areas with soaring ceilings. Tile flooring runs throughout the first floor. A covered paver patio extends the living space outdoors. A first-floor bedroom with en suite bathroom and walk-in closet provides added flexibility. Upstairs, fresh interior paint (2024), new carpet (2024), and a 15x10 loft add comfort and versatility. Two secondary bedrooms share a dual-sink bath. The primary suite features a spa-style bathroom with dual sinks and an oversized walk-in closet. Separate upstairs laundry room included. Additional highlights: freshly painted exterior, energy-efficient dual-pane windows, HOA-maintained landscaping, and a 2-year home warranty conveying at closing. Resort-style community amenities include pools, clubhouse, and parks — all minutes from Walt Disney World. Schedule your showing today.
Listing is courtesy of: EXP REALTY LLC (407-392-1800)
Listing Agent: Jeanine Louis, Llc (407-595-8634)
15558 SANDFIELD LOOP, WINTER GARDEN, FL 34787
$795,00021 Days on yellowkey MLS ID: O6393987
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4307 Built: 2014Monthly Fee: $114 Tax: $5,670 (2025)Community: Reserve/Carriage Pointe Ph 1Single Family
Taxes:$5,670
Elementary School: Hamlin Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates.
Listing is courtesy of: ORLANDO HIGHLAND REALTY LLC (561-385-7610)
Listing Agent: Xiaoli Lin (561-385-7610)
9728 NANCY DREW ALY, WINTER GARDEN, FL 34787
$524,990171 Days on yellowkey MLS ID: O6355911
3 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2475 Built: 2020Monthly Fee: $108 Tax: $8,203 (2024)Community: Storey Grove Ph 2Single Family
Taxes:$8,203
Remarks: Under contract-accepting backup offers. Seller is motivated to align closing with the end of the current school year (late May). Your home has paid-off solar panels, Whole-house Water Softener system, and Installed Gutters, SCREENED backyard, Disney fireworks views right from your living room! TWO luxurious Primary Suites on Each Floor with walk-in closets. Upstairs, enjoy your spacious loft along with two additional bedrooms and a full bath, offering plenty of room for family, work, or relaxation. Step outside to your private screened-in backyard with a beautiful paver patio, perfect for enjoying Florida living year-round. A unique feature of this home is the Fully Screened walkway connecting the main house to the rear garage, providing added comfort and functionality. Just minutes from both the elementary and middle school, this home offers unmatched convenience for families. The community features resort-style amenities, including a pool, fitness center, playground, and dog park. Homes with this combination of location, layout, and upgrades are rarely available — your home is waiting for you!
Listing is courtesy of: U S GLORY REALTY (407-222-7801)
Listing Agent: Rui Gao (407-222-7801)
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