Location: Winter Garden , 34787
Do Not Show Listings
10472 PETRILLO WAY, WINTER GARDEN, FL 34787
$1,065,00060 Days on yellowkey MLS ID: O6382263
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4025 Built: 2022Monthly Fee: $102 Tax: $12,049 (2025)Community: Winding Bay Ph 2Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$12,049
Elementary School: Water Spring Elementary
High School: Horizon High School
Tax Year: 2025
Middle School: Water Spring Middle
Remarks: Welcome to 10472 Petrillo Way in Winding Bay Preserve, one of Winter Garden’s most desirable communities in Horizon West. Built in 2022, this stunning K. Hovnanian Grayson Model sits on a premium corner, EAST-FACING lot with DISNEY FIREWORK VIEWS and the rare opportunity to watch Space Coast ROCKET LAUNCHES right from your front porch. This home offers 5 bedrooms, 6 bathrooms, a private office, loft, and media room, delivering a spacious and thoughtfully designed layout ideal for luxury living in Central Florida. From the moment you enter, you’re greeted by soaring ceilings, crown molding, tray ceilings, luxury vinyl plank flooring downstairs, engineered hardwood in the upstairs common areas, and a stately wrought iron staircase. A built-in speaker system enhances the home’s elevated design, while ceiling fans sourced from iconic Disney properties add a distinctive touch. The gourmet kitchen anchors the home with GE Profile stainless steel appliances, granite countertops, custom soft-close cabinetry, under-cabinet lighting, a modern hood vent, and an oversized walk-in pantry. The open-concept floor plan seamlessly connects the kitchen to the living and dining spaces, creating the perfect flow for entertaining or everyday family living. The expansive first-floor primary suite offers a serene retreat overlooking the pool, complete with motorized blackout shades, a freestanding soaking tub, dual vanities, a frameless glass walk-in shower, and a spacious walk-in closet. A separate pool bath and a downstairs secondary bedroom with ensuite make this home ideal for guests or multi-generational living, while the private office with French doors provides a quiet and functional work-from-home space. Upstairs, the home continues to impress with a large loft, a dedicated media or theater room wired for surround sound, and three additional bedrooms, each featuring walk-in closets and access to private bathrooms. The layout provides both privacy and flexibility, perfect for growing families or hosting guests. Step outside to your private backyard oasis featuring a custom heated saltwater pool and spa, screened lanai, smart pool controls, fully fenced yard, and peaceful pond views. From the upstairs front bedroom, enjoy magical Disney fireworks lighting up the night sky, a rare and enchanting feature that enhances everyday living. Located just minutes from Walt Disney World, Hamlin Town Center, Flamingo Crossings, and major highways for easy commuting throughout Orlando, this home combines luxury, location, and lifestyle. Residents of Winding Bay Preserve enjoy access to a community pool, playground, and top-rated schools within one of the fastest-growing and most sought-after areas of Winter Garden. If you are searching for a luxury pool home near Disney, a move-in-ready 2022-built home in Horizon West, or a spacious five-bedroom home in Winter Garden with high-end finishes, 10472 Petrillo Way offers exceptional value and an elevated Florida lifestyle. Schedule your private showing and experience one of Winter Garden’s premier homes today.
Listing is courtesy of: EXP REALTY LLC (407-392-1800)
Listing Agent: Alexis Bress (407-900-0771)
15381 HONEYBELL DR, WINTER GARDEN, FL 34787
$426,00022 Days on yellowkey MLS ID: O6391881
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2034 Built: 2016Monthly Fee: $418 Tax: $4,853 (2025)Community: Hamlin ReserveTownhouse
Taxes:$4,853
Elementary School: Keene Crossing Elementary
High School: Windermere High School
Middle School: Bridgewater Middle
Remarks: Live in the heart of Hamlin Reserve, this stylish executive townhome sits directly across from the community pool and playground, just a five-minute drive or short distance to Hamlin Town Center for convenient shopping, dining and everyday essentials in Horizon West. Spanning over 2,000 square feet, this four-bedroom, three-bath home with two-car garage and private patio is thoughtfully designed for comfortable, modern living. The main level features an open-concept layout with a guest bedroom and full bath, along with a well-appointed kitchen complete with a large granite island, stainless steel appliances and a spacious pantry, ideal for everyday living and entertaining. A private, partially covered courtyard offers a comfortable outdoor space and leads to an oversized rear-entry two-car garage. The second level features a split floor plan with three bedrooms, two full baths and a laundry room. Relax and unwind in the serene primary suite, complete with a private balcony offering picturesque views of the pool and playground, an ideal vantage point for nightly views of Walt Disney World fireworks. The primary suite also includes an en-suite bath with dual vanities, a glass-enclosed shower and a generously sized walk-in closet. Residents enjoy a maintenance-free lifestyle with HOA-covered exterior care, landscaping, roofing and access to resort-style amenities including a pool, clubhouse, playground, dog park and scenic green spaces, all just near your front door. Positioned near Hamlin Town Center, you’ll experience a vibrant, accessible community with boutique shopping, dining and entertainment, including Cinépolis Luxury Cinemas. With proximity to Orlando Health Horizon West Hospital, Orange County National Golf Center and Horizon West Regional Park, plus easy access to major highways, this home offers a balance of luxury, convenience and lifestyle in one of Central Florida’s sought-after communities. A 2016 roof (HOA maintains), 2016 air conditioner and 2026 water heater.
Listing is courtesy of: PREMIER SOTHEBY'S INTL. REALTY (407-644-3295)
Listing Agent: Jj Mackle (321-217-9553)
15226 SUNSET OVERLOOK CIR, WINTER GARDEN, FL 34787
$1,100,00026 Days on yellowkey MLS ID: O6390971
REDUCED by $50,000 (4.3%) on 03/31/2026
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3556 Built: 2023Monthly Fee: $128 Tax: $10,299 (2025)Community: Johns Lake PointeSingle Family
Taxes:$10,299
Elementary School: SunRidge Elementary
High School: West Orange High
Middle School: SunRidge Middle
Remarks: Welcome to this Beautifully Designed David Weekley home, built in 2023 and meticulously maintained in the Overlook portion of Johns Lake Pointe offering over 3,500 square feet of thoughtfully designed living space on an oversized lot. From the moment you step inside, you’re greeted by luxury vinyl plank flooring, expansive 10-foot ceilings, and abundant natural light that create a warm yet refined first impression. Just off the entry, a private office provides the ideal work-from-home space, while a guest bedroom with a nearby full bath is perfectly tucked away for privacy and convenience. As you continue into the heart of the home, you’ll fall in love with the open-concept living area, where the family room, dining space, and gourmet kitchen come together seamlessly—perfect for both everyday living and entertaining. The kitchen serves as a true centerpiece, featuring an oversized island, designer finishes, and ample cabinetry, all overlooking the main living space. Upstairs, you will be greeted by a spacious bonus room that offers endless flexibility—ideal for a media room, game room, or secondary living area. The Master suite is a true retreat, complete with a private walk-out balcony, Tray ceiling and a luxurious en-suite bathroom featuring a standalone garden tub, oversized walk-in shower, and a massive walk-in closet. On the other side of the home, two bedrooms share a convenient Jack-and-Jill bathroom, while a third bedroom is nestled with a full bath just outside its door, providing privacy and ease. The upstairs laundry room adds everyday convenience. This home has been meticulously maintained throughout. The community features a resort-style pool, tennis courts, playground and clubhouse that includes a gym, yoga room, gathering area and kitchen. Neighborhood is minutes from Downtown Winter Garden and Winter Garden Village as well as within walking/biking distance from the elementary and middle school. Also conveniently located to most major highways making commuting to work easier than ever. Don't hesitate, make your appointment today!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: T.J. O'Donnell (317-246-8190)
238 N MAIN ST, WINTER GARDEN, FL 34787
$600,0006 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
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
$500,00039 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
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
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)
883 TILDEN OAKS TRL, WINTER GARDEN, FL 34787
$1,075,000Listed 04/13/2026 1:06PM MLS ID: O6393635
0 Days Off yellowkey (back on 4/13/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2811 Built: 2025Monthly Fee: $625 Tax: $3,649 (2025)Community: Oakland ParkSingle Family
Taxes:$3,649
Elementary School: Tildenville Elem
Remarks: Under contract-accepting backup offers. Nestled in the heart of Winter Garden’s beloved Golf Cart District, this oversized Seaside model by David Weekley invites you to embrace a lifestyle where luxury meets charm. Tucked within the picturesque Oakland Park Subdivision, this home offers not just a place to live but a way to experience the very best of this vibrant community. Step inside, and you’re greeted by the golden warmth of light wood laminate floors and streams of natural light pouring through every window. The gourmet kitchen, truly the soul of the home, is a chef’s haven with a gas stovetop, sleek finishes, and plenty of room to gather, cook, and connect. Just steps away, the main-floor master retreat becomes your personal sanctuary—offering peace, privacy, and every comfort you could wish for. The second floor is a haven in its own right, with three spacious bedrooms circling a versatile loft space. Whether it becomes a playroom, a cozy reading nook, or your dream work-from-home setup, the possibilities are endless. Outside, the rare 3-car garage, discreetly accessed via a quiet alley, adds both convenience and a touch of exclusivity. But the magic doesn’t stop at your doorstep. Imagine mornings strolling leafy trails, afternoons exploring Winter Garden's historic downtown, and evenings savoring craft beer or artisan treats at the nearby Plant Street Market—a true local gem just moments away. From farmers markets to boutique shops, this is a neighborhood where every day feels like a celebration. This isn’t just a home; it’s a gateway to the lifestyle you’ve been dreaming of. Don’t wait—schedule your private tour today and let this storybook setting become your reality.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matthew Mckee (407-948-0658)
1075 CHASE DR, WINTER GARDEN, FL 34787
$625,00043 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)
14501 GROVE RESORT AVE #2527, WINTER GARDEN, FL 34787
$270,000117 Days on yellowkey MLS ID: O6368187
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1544 Built: 2018Monthly Fee: $1,103 Tax: $8,868 (2024)Community: Grove Residence & Spa Hotel Condo IiCondo
Taxes:$8,868
Remarks: Short Sale. Short Sale Opportunity – Fully Furnished 3BR/3BA Condo at The Grove Resort – Vacation Rental Only / No Full-Time Residency Investor Alert! Rare opportunity to own a FULLY FURNISHED and equipped 3-bedroom, 3-bath condo in the sought-after The Grove Resort, one of Orlando’s top vacation-only condo-hotel communities, just minutes from Disney. Turnkey for immediate rental. Large balcony, modern kitchen, and in-unit washer/dryer. High occupancy potential through the on-site rental program. Resort Amenities (included for guests): Surfari Water Park, surf simulator, water slides, laser river. Multiple resort-style pools, hot tubs & cabanas. Lake Austin access with fishing and water sports. Fitness center, arcade, full-service spa, on-site restaurants, bars, market, and conference center, 24/7 front desk, concierge, and gated community security. Prime Location, located in Winter Garden, FL, just minutes to Walt Disney World® and major Orlando attractions. Close to shopping, dining, and major highways. This unit is part of a condo-hotel program: no full-time residency allowed. Short-term rentals only. SHORT SALE – priced to sell fast! A great chance to secure a unit below market value in a high-demand tourist location. Ideal for investors looking for short-term rental income with professional management available on-site. Not suitable for full-time occupancy. Contact us today to schedule a showing and take advantage of this exceptional income-generating property!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Nayane Seabra (407-535-7815)
8216 TOPSAIL PL, WINTER GARDEN, FL 34787
$974,90028 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
Elementary School: Panther Lake Elementary
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)
14501 GROVE RESORT AVE #1612, WINTER GARDEN, FL 34787
$299,000176 Days on yellowkey MLS ID: S5136940
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1375 Built: 2016Monthly Fee: $875 Tax: $6,828 (2024)Community: Grove Resort And Spa Hotel Condo 1Condo
Taxes:$6,828
Remarks: The VIEW! Come enjoy this EXCEPTIONAL Fully Furnished 6th floor Vacation Condo unit with WATER AND CONSERVATION VIEWS plus Evening Fireworks views from your private South-facing Balcony at The Grove Resort and Spa/Water Park in Orlando near Walt Disney World! Experience the Resort FUN yourself and enjoy the income-producing option to rent out your unit when you are away. This Full-service Fully-furnished Luxury Resort unit is the Birch model (split plan 1375 sq ft) in Bldg 1 section H; Bldg 1 allows financing! Two bedroom suites plus sleeper sofa in the great room, TVs in all rooms, Fully equipped Kitchen, inside private Laundry room, a short walk to Attached Garage parking, and the Fitness Center is conveniently just downstairs! Experience lifetime memories at the multitude of amenities on site: the Surfari Water Park with an amazing FlowRider Surf Simulator, Lazy River, Water slides, numerous pools and activities, cabanas, meeting areas, shopping options and Family Fun Center, or escape just minutes away to neighboring theme parks, shopping, restaurants, and more!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Lois Ann Cox, Pa (407-666-8452)
17006 SEVILLE ORANGE RD, WINTER GARDEN, FL 34787
$718,79912 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)
15659 JUNGLE ALY, WINTER GARDEN, FL 34787
$360,00024 Days on yellowkey MLS ID: S5143684
REDUCED by $85,000 (19.1%) on 03/31/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1732 Built: 2021 Tax: $6,265 (2024)Community: Winding Bay Ph 2Townhouse
Taxes:$6,265
Remarks: AGENTS - PLEASE VIEW REALTOR REMARKS IN THE MLS. Beautifully maintained town home 3 bed and 3 bath in the desirable Horizon West area of Winter Garden! This charming alley-facing property features an open-concept floor plan with spacious living and dining areas, a modern kitchen with solid surface countertops, stainless steel appliances, and a large island perfect for entertaining. Upstairs offers generously sized bedrooms, including a private primary suite with walk-in closet and en-suite bath. Enjoy low-maintenance outdoor living with a private patio and rear-entry garage. Conveniently located near top-rated schools, shopping, dining, and major roadways. A fantastic opportunity to own in one of Central Florida’s most sought-after communities! Offers may be entered ONLINE through Tuesday, April 14, 2026 at 3:00 pm. AT SELLER'S DISCRETION, A SUBMISSION MAY BE ACCEPTED AT ANY TIME.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Dinorah Navarro (407-625-7522)
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999176 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)
940 MARSH REED DR, WINTER GARDEN, FL 34787
$799,990Listed 04/13/2026 11:26AM MLS ID: O6397274
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3493 Built: 2015Monthly Fee: $128 Tax: $10,543 (2025)Community: Johns Lake PointeSpa: NoSingle Family
Taxes:$10,543
Remarks: One or more photo(s) has been virtually staged. Welcome to 940 Marsh Reed Drive, a beautifully upgraded 5 bedroom, 3 bathroom, SOLAR HEATED POOL HOME offering just under 3,500 square feet of well-designed living space in the highly sought-after Johns Lake Pointe community! Additional OFFICE and LOFT / BONUS ROOM. Solar panels are paid off! From the moment you arrive, the home makes a strong impression with its tile roof, enhanced landscaping, and well manicured appearance, setting the tone for what’s inside. The interior opens to a bright, expansive layout with high ceilings, neutral finishes, and multiple living and dining areas designed for both everyday comfort and entertaining. The heart of the home is the open-concept kitchen, featuring abundant cabinetry, walk-in pantry, granite countertops, stainless steel appliances, extended butler's pantry style prep area, and a large center island that flows seamlessly into the main living area. Natural light fills the space, creating an inviting atmosphere that connects effortlessly to the indoor and outdoor living areas. The first floor dedicated office provides the ideal work-from-home setup or can easily function as a flex space to suit your needs. Upstairs, a spacious loft/bonus area offers additional versatility—perfect for a media room, playroom, or secondary living space. The primary suite is generously sized and features tray ceilings, large windows, and a relaxing, private feel. The en-suite bathroom includes dual vanities, a walk-in shower, walk-in closet, and ample storage, creating a comfortable retreat at the end of the day. Step outside to your private backyard oasis, where the SCREENED-IN POOL and covered lanai deliver the ultimate Florida lifestyle. The pool is equipped with SOLAR HEATING for year-round enjoyment and a NEW POOL PUMP for efficiency. A standout feature is the $7,000 integrated smart exterior lighting system, including the pool enclosure, creating a stunning nighttime ambiance perfect for entertaining. Additional upgrades include a new gutter drainage system and overhead garage storage racks, offering both convenience and functionality. Located in Johns Lake Pointe, residents enjoy access to resort-style amenities including a community pool, fitness center, playground, and sports courts, all while being just minutes from major highways, shopping, dining, Winter Garden's Historic Plant Street, and everything Central Florida has to offer. Only a short drive to Disney! Close to HIGH-RATED SCHOOLS. This is a rare opportunity to own a move-in ready home that combines space, upgrades, and lifestyle in one exceptional package. Call now for your private showing!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Andrew Kincaid (407-304-0454)
9849 LOST CREEK DR, WINTER GARDEN, FL 34787
$990,000509 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
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
$594,00064 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)
150 WINDTREE LN #150, WINTER GARDEN, FL 34787
$199,900129 Days on yellowkey MLS ID: O6365343
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 918 Built: 1984Monthly Fee: $300 Tax: $2,565 (2025)Community: Windree Gardens Ph 5Condo
Taxes:$2,565
Elementary School: Maxey Elem
Remarks: One or more photo(s) has been virtually staged. Experience comfort, style, and convenience in this lovely 2 bed + 2 bath condo located just 5 minutes from popular Plant Street in Winter Garden. This bright, well-maintained unit features a wonderful split floor plan with two spacious bedrooms separated by an open-concept kitchen and living room. The kitchen has quality appliances, including a new dishwasher, an inviting eat-in bar, and neutral finishes that complement any decor. The large great room fills with natural light and opens to a private patio - perfect for morning coffee, a good book, or unwinding at the end of the day. Additional conveniences include two reserved parking spaces, a huge secured storage area, and an in-unit Bosch washer and dryer. The quiet, well-kept community offers fantastic amenities such as a private pool, basketball courts, plenty of green space, and nearby walking trails. Schedule your viewing today!
Listing is courtesy of: ROMAN REALTY GROUP, LLC (407-876-1990)
Listing Agent: Brian Lemay (321-314-5412)
12911 WESTHAVEN OAK DR, WINTER GARDEN, FL 34787
$548,00069 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
$565,000131 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 Agent: Jeanine Louis, Llc (407-595-8634)
16736 OAKBORO ST, WINTER GARDEN, FL 34787
$585,00026 Days on yellowkey MLS ID: O6388784
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2020Monthly Fee: $257 Tax: $6,967 (2024)Community: WaterleighSpa: NoSingle Family
Taxes:$6,967
Remarks: OVER $43,000 IN UPGRADES INCLUDING A WHOLE HOUSE SOLAR PANEL SYSTEM INCLDED IN PURCHASE! Be delighted with the reduced energy expenses from the day you move in. Don't wait to build and take advantage of the massive upgrades! Great opportunity to make homeownership a reality in the beautiful community of Waterleigh in Horizon West. HOA covers lawncare allowing you to enjoy all that Waterleigh has to offer: resort style amenities catering to any lifestyle, including a large club house with community room and fitness center that opens to a freeform pool, grilling stations and plenty of deck space to relax in the Florida sun. The sports enthusiast will fall in love with the multiple ball fields, tennis courts, beach volleyball court, pickle ball and outdoor fitness circuit. Playgrounds, gazebos and parks are scattered throughout the community for your pleasure. Phase three has a separate pool that is a great alternative to the main pool complex. This Clearden model offers many options and versatility. Natural light is amazing in every room! The first floor features an open plan with a bright white kitchen featuring a center island, stainless steel appliances, walk-in pantry as well as a coffee or dry bar area and overlooks the spacious family room that leads to the covered lanai. Main floor full bedroom with a private bath is ideal for guests, an office or an in-law suite. Upstairs there is an open loft, three additional bedrooms and a large laundry room. The expansive primary suite has an ensuite bathroom equipped with a double vanity, walk-in shower and plenty of closet space. The entertaining expands to the outside with covered front and rear lanais perfect for morning coffee or an evening BBQ. The fully fenced yard, whole home water softener, security system and solar panels add to the many upgrades in this beautiful home. Attached rear entry oversized two car garage provides plenty of room to park two vehicles and the brick paver driveway can accommodate up to four additional vehicles. Take advantage of the many community activities that are sponsored by the HOA for your pleasure year-round. Zoned for top rated schools including the elementary and middle schools within walking distance. Shopping, restaurants and lifestyle shops are all within the planned community. Minutes to the Walt Disney World complex, major roadways and an easy commute to the Orlando International Airport or Downtown Orlando. Special note, this home is equipped with Solaredge Solar panels that come with a transferrable warranty to the new Owner. This feature significantly reduces the monthly power bill! Call today for a private showing.
Listing is courtesy of: COLDWELL BANKER REALTY (407-647-1211)
Listing Agent: Michael Morris (407-383-5434)
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