Location: Winter Garden , 34787
Do Not Show Listings
238 N MAIN ST, WINTER GARDEN, FL 34787
$600,0009 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,389
Elementary School: Dillard Street Elem
High School: West Orange High
Tax Year: 2025
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
$500,00042 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)
1075 CHASE DR, WINTER GARDEN, FL 34787
$625,00046 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
$270,000120 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
$974,90031 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
High School: Horizon High School
Middle School: Water Spring Middle
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
$299,000179 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
$718,79915 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
$1,499,999179 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
$990,000512 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
$594,00067 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
$199,900132 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
$548,00072 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
$565,000134 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
$795,00022 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
Middle School: Hamlin Middle
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
$524,990172 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)
16209 PRAIRIE SCHOOL DR, WINTER GARDEN, FL 34787
$399,00022 Days on yellowkey MLS ID: O6392111
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1626 Built: 2020Monthly Fee: $286 Tax: $5,581 (2025)Community: Hawksmoor-Ph 3Townhouse
Taxes:$5,581
Remarks: Under contract-accepting backup offers. Located in the desirable Hawksmoor community in Winter Garden, this well-designed two-story townhome offers a functional layout paired with clean, move-in ready finishes. The main level features a defined entry leading into a dining space that flows into a spacious kitchen equipped with granite countertops, stainless steel appliances, and an oversized island ideal for everyday use and entertaining. The kitchen opens directly to the gathering room, creating a natural connection between spaces while maintaining distinct areas. Just off the living area, a private paver courtyard provides a low-maintenance outdoor setting, perfect for relaxing evenings or hosting guests. Upstairs, the primary suite features a tray ceiling, generous layout, and a well-appointed en suite bath with dual sinks, granite counters, and a glass-enclosed shower. Two additional bedrooms offer flexibility for guests, a home office, or everyday living and share a full bath. Residents of Hawksmoor enjoy access to a clubhouse, community pool, splash pad, fitness center, playground, and a recreational field with full-sized soccer goal posts, enhancing the overall lifestyle experience. Conveniently located near shopping, dining, major roadways, and everything Winter Garden has to offer, this home delivers comfort, convenience, and a strong sense of community.
Listing Agent: Iris Glover (203-461-4236)
17031 HAGGERTY HOLLOW DR, WINTER GARDEN, FL 34787
$646,0905 Days on yellowkey MLS ID: G5110934
0 Days Off yellowkey (back on 4/12/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2680 Built: 2026Monthly Fee: $140Community: Hamlin Meadows At HamlinSingle Family
Taxes:$0
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Berkley model features 2,102 square feet of well-designed living space across two stories, with an above-garage Apt 576 sqft.This home includes 3 bedrooms, 3 full bathrooms, and a 2-car garage. The open-concept main floor boasts a spacious family room, dining area, and a modern kitchen with ample counter space—ideal for both daily living and entertaining. The primary suite is located on the first floor for added privacy, with a luxurious bath and walk-in closet. Upstairs, two additional bedrooms and a full bath provide flexible living options for guests or family members. The apartment is above the garage with a private entrance. This neighborhood features a variety of townhomes and single-family homes on multiple-sized homesites, with spacious floor plans designed to support a wide range of lifestyles, from growing families to move-up buyers seeking more room to live and entertain. Located just minutes from Hamlin Town Center, Winter Garden Village, and historic Downtown Winter Garden, Hamlin Meadows places shopping, dining, and entertainment close to home. Residents will also enjoy access to nearby parks, trails, and outdoor recreation, along with proximity to highly regarded Orange County schools, including Hamlin Elementary, Hamlin Middle, and Horizon High School.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
17428 SUNSET PRAIRIE DR, WINTER GARDEN, FL 34787
$740,2055 Days on yellowkey MLS ID: G5110933
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3412 Built: 2026Monthly Fee: $140Community: Hamlin Meadows At HamlinSingle Family
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage
13393 SUNSET LAKES CIR, WINTER GARDEN, FL 34787
$867,0005 Days on yellowkey MLS ID: O6398468
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2186 Built: 1994Monthly Fee: $69 Tax: $6,434 (2025)Community: Sunset LakesSpa: NoSingle Family
Taxes:$6,434
Remarks: Beautifully updated single-story home featuring 4 bedrooms and 3 bathrooms, situated on an expansive lot of over half an acre in the desirable Sunset Lakes community. This residence offers a spacious layout ideal for comfortable living and has been fully remodeled throughout. The home features a great gourmet kitchen with a large island and sleek Dekton countertops, perfect for both everyday living and entertaining. Step outside to a stunning backyard retreat with a private pool and screened enclosure, ideal for year-round enjoyment. Ideally located just minutes from Highway 429, Winter Garden Village, and world-renowned attractions like Walt Disney World, this property also benefits from access to highly rated A-grade schools, making it an exceptional opportunity in one of Winter Garden’s most sought-after areas.
Listing is courtesy of: VALSTAR REALTY LLC (407-270-5000)
Listing Agent: Otto Solis Parraga (407-431-1789)
5637 TIGER WAY, WINTER GARDEN, FL 34787
$765,0005 Days on yellowkey MLS ID: O6398378
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2917 Built: 2018Monthly Fee: $214 Tax: $12,077 (2025)Community: Overlook 2/Hamlin Ph 3Single Family
Taxes:$12,077
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Fantastic Jamestown model with 4 bedrooms, 2.5 bath with screened lanai and backing to common area. Home upgrades include Solar Panels, under eaves lighting, water filtration system, new flooring and updated secondary bath. The home is located close to the Hamlin Town Center and is located in a sought after planned community with pool, clubhouse, parks, fitness center and dog park. Easy access to SR429 and the Florida Turnpike.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: Nancy Foltz (703-772-0215)
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