Location: Winter Garden , 34787
Do Not Show Listings
231 DOE RUN DR, WINTER GARDEN, FL 34787
$500,00011 Days on yellowkey MLS ID: O6412284
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1972 Built: 2006Monthly Fee: $57 Tax: $3,202 (2025)Community: Deerfield Place A-GSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,202
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Imagine coming home to a place where comfort, convenience, and community come together perfectly. Nestled in the highly desirable Deerfield Place neighborhood, this beautiful 4-bedroom, 2-bath home offers the space, style, and location today's buyers are searching for. From the moment you step inside, you'll appreciate the bright, open layout designed for making memories. The heart of the home is the spacious kitchen, featuring upgraded cabinetry, stainless steel appliances, and plenty of room to gather with family and friends. Whether you're hosting holiday celebrations, enjoying a quiet morning coffee, or helping with homework while preparing dinner, this home was designed for the moments that matter most. The private owner's retreat provides a peaceful escape at the end of the day, while the additional bedrooms offer flexibility for family, guests, a home office, or a fitness space. Step outside to your fully fenced backyard, perfect for weekend barbecues, pets, playtime, or simply relaxing under the Florida sunshine. What truly sets this home apart is its incredible Winter Garden location. Just minutes from Historic Downtown Winter Garden, the award-winning West Orange Trail, Winter Garden Village, top-rated schools, dining, shopping, and entertainment, you'll enjoy the best of Central Florida living right outside your door.
Listing is courtesy of: THE C SMITH REAL ESTATE GROUP LLC (407-705-7797)
Listing Agent: Rick Coles (321-299-4981)
10089 SALT POINT DR, WINTER GARDEN, FL 34787
$465,00072 Days on yellowkey MLS ID: O6392385
REDUCED by $10,000 (2.1%) on 06/05/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1654 Built: 2022Monthly Fee: $260 Tax: $6,886 (2025)Community: Waterleigh Ph 2ETownhouse
Taxes:$6,886
Elementary School: Avalon Elem
High School: Horizon High School
Middle School: Water Spring Middle
Remarks: It can be negotiated along with the furniture. Welcome to this beautifully maintained 3-bedroom, 3-bathroom townhouse located in the highly desirable Waterleigh community. This modern home offers a functional and inviting open-concept layout, perfect for both everyday living and entertaining. The property features spacious bedrooms, well-appointed bathrooms, and a thoughtfully designed living area filled with natural light. The kitchen stands out with contemporary finishes, ample cabinetry, and a seamless flow into the dining and living spaces. Furniture can be negotiated, providing a convenient move-in-ready opportunity. Residents of Waterleigh enjoy a resort-style lifestyle, including multiple clubhouses, sparkling pools, fully equipped fitness centers, scenic walking trails, playgrounds, sports courts, and beautifully maintained green spaces. The community is known for its welcoming atmosphere and well-planned design. Ideally located, this home offers easy access to everyday essentials and top destinations, including Horizon West, Hamlin Town Center, and the popular Walt Disney World Resort. Enjoy a wide variety of nearby shopping, dining, and entertainment options, along with convenient access to major highways. This is an excellent opportunity to enjoy comfort, convenience, and one of the most sought-after communities in the area.
Listing is courtesy of: AUTHENTIC REAL ESTATE TEAM (407-440-1010)
Listing Agent: Tiago Ferreira (407-440-1010)
617 MARSH REED DR, WINTER GARDEN, FL 34787
$750,00042 Days on yellowkey MLS ID: O6402724
REDUCED by $9,000 (1.2%) on 06/05/2026
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2828 Built: 2016Monthly Fee: $128 Tax: $5,746 (2025)Community: Johns Lake PointeSingle Family
Taxes:$5,746
Elementary School: SunRidge Elementary
High School: West Orange High
Middle School: SunRidge Middle
Remarks: From the moment you arrive, this home feels like a place to slow down, settle in, and truly enjoy the best of Winter Garden living. Set within a quiet community, it offers a welcoming blend of comfort, natural light, and thoughtfully designed spaces that make everyday life feel just a little more special. Inside, the home is filled with bright, natural light that enhances its open and inviting feel. Careful attention to design creates a sense of warmth and refinement throughout, offering spaces that are both functional and comfortable for daily living or hosting guests. Step outside to a stunning covered pool area that becomes the heart of the home. Whether you are enjoying a quiet morning or gathering with friends, this private outdoor space offers the perfect setting to relax and unwind while taking full advantage of Florida living year-round. The surrounding community adds another layer of appeal, offering access to amenities such as a clubhouse, pool, and tennis courts that support both recreation and connection. The neighborhood setting encourages time outdoors while maintaining a peaceful and well-kept environment. Location is where this home truly shines. Just minutes from the vibrant Horizon West and Hamlin area, you will enjoy easy access to shopping, dining, and everyday conveniences. Nearby major roadways make commuting and travel simple, while local attractions and outdoor spaces provide endless opportunities to explore and enjoy your surroundings. This home offers a unique balance of comfort, convenience, and lifestyle, creating a space where both everyday moments and special occasions feel effortless. Schedule your private showing to experience it in person and see how it fits your next chapter.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Stacey Vazquez (407-874-5751)
1061 PORTMOOR WAY, WINTER GARDEN, FL 34787
$535,0006 Days on yellowkey MLS ID: G5113349
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1804 Built: 2001Monthly Fee: $243 Tax: $6,801 (2025)Community: Stoneybrook West 44/134Single Family
Taxes:$6,801
Elementary School: Whispering Oak Elem
Remarks: Welcome to 1061 Portmoor Way, a single-story 4-bedroom, 2-bathroom home located in the highly desirable Stoneybrook West community—a 24-hour manned, guard-gated golf community known for its resort-style living. This home features inviting modern living spaces that flow seamlessly to a fully fenced backyard with a patio, creating the perfect setting for outdoor relaxation and entertaining. New Roof installed in 2020, water heater installed in 2022, stainless steel appliances, modernized kitchen, tiled floor in kitchen, bathrooms and laundry room. Residents of Stoneybrook West benefit from an outstanding amenity lifestyle, including 24-hour security, a clubhouse, fitness center, resort-style pool, tennis, basketball and volleyball courts, playground, fishing dock, and a boat ramp with access to Black Lake. The community is also home to Stoneybrook West Golf Club and SB Prime restaurant and bar. HOA dues include internet and Spectrum TV, offering added convenience and value. Ideally located minutes from Winter Garden Village, downtown Winter Garden, and SR-429, this home provides easy access to shopping, dining, entertainment, and everyday essentials while still offering a peaceful, gated community setting.
Listing is courtesy of: ENGEL & VOLKERS CLERMONT (407-905-6700)
Listing Agent: Lisa Reed (407-509-7995)
2123 PORTCASTLE CIR, WINTER GARDEN, FL 34787
$389,0008 Days on yellowkey MLS ID: O6412643
0 Days Off yellowkey (back on 6/4/2026)
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1606 Built: 2006Monthly Fee: $46 Tax: $5,857 (2025)Community: Stone Creek Unit 4Single Family
Taxes:$5,857
Remarks: One or more photo(s) has been virtually staged. Welcome to your family's next home in the highly desirable Stone Creek community of Winter Garden. This spacious two-story residence features 4 bedrooms, 2.5 bathrooms, and a versatile upstairs loft, perfect for a home office, playroom, or additional living space. Step inside to an open-concept living and dining area with stylish flooring throughout—no carpet throughout! The thoughtfully designed floor plan offers all four bedrooms upstairs, providing privacy and separation from the main entertaining areas. The spacious primary suite features an en-suite bathroom with dual vanities and a walk-in closet. Conveniently located downstairs, you'll find the laundry room and a half bath for guests. Families will appreciate being zoned for Whispering Oak Elementary School, a National Blue Ribbon School and one of the highest-rated schools in the Orlando area. Enjoy an unbeatable location just minutes from Winter Garden Village, Hamlin Town Center, and historic Downtown Winter Garden, with easy access to State Road 429 and the Florida Turnpike. Plus, Disney World and Orlando's top attractions are only a short drive away. Don't miss this opportunity to own a beautiful home in one of Winter Garden's most sought-after communities.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Erica Diaz (407-897-5400)
15615 HONEYBELL DR, WINTER GARDEN, FL 34787
$389,90029 Days on yellowkey MLS ID: O6406267
1 Days Off yellowkey (back on 6/5/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1584 Built: 2017Monthly Fee: $418 Tax: $6,085 (2025)Community: Hamlin ReserveTownhouse
Taxes:$6,085
Elementary School: Independence Elementary
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated townhome in the highly desirable Hamlin Reserve community of Winter Garden, offering the perfect blend of comfort, style, and low-maintenance living. This move-in ready home stands out from the competition with fresh interior paint and brand new flooring, creating a clean, modern feel from the moment you walk in. Featuring a functional and spacious layout, this property is ideal for both primary residence buyers and investors seeking a well-maintained home in a prime location. Bright, open living spaces flow seamlessly, making it perfect for everyday living and entertaining. Located in Hamlin Reserve, you’ll enjoy easy access to Hamlin Town Center, shopping, dining, and major highways, and you are just a short drive to Walt Disney World, making this area highly attractive for both homeowners and long-term investment potential. You’re also minutes from Horizon West and everything Winter Garden has to offer. As a townhome, it provides the benefit of lower maintenance compared to single-family homes, making it an excellent option for busy homeowners or those looking for a lock-and-leave lifestyle. With its recent upgrades, prime location, and standout condition, this home is a rare opportunity in today’s market. Schedule your private showing today.
Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)
Listing Agent: Arturo Ortiz (407-502-8752)
15625 BOGGY OAK CIR #108B, WINTER GARDEN, FL 34787
$340,00022 Days on yellowkey MLS ID: G5112579
REDUCED by $4,900 (1.4%) on 06/05/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1419 Built: 2010 Tax: $3,605 (2025)Community: Tucker Oaks Ph 8Condo
Taxes:$3,605
Remarks: Beautifully maintained 3-bedroom, 2.5-bath townhome located in the gated Tucker Oaks community in Winter Garden. This home features an open-concept floor plan with abundant natural light, a functional layout, and an attached garage for added convenience. The kitchen offers ample cabinet and counter space and overlooks the living and dining areas. Upstairs, the primary suite includes a private bath and walk-in closet, while the additional bedrooms provide flexibility for guests, work-from-home space, or other uses. Recent updates include a new roof, dishwasher, and garbage disposal installed in August 2024, along with an HVAC system replaced in 2022. Community amenities include a pool, playground, basketball courts, scenic areas, and dog parks — including one conveniently located on the same cul-de-sac as the condo. Conveniently located near Downtown Winter Garden, Winter Garden Village, SR-429, Florida’s Turnpike, shopping, dining, hospitals, and area attractions. This property offers low-maintenance living with convenient access to major commuter routes and Central Florida destinations.
Listing is courtesy of: SCATES REALTY & INVESTMENT PRO (352-404-8960)
Listing Agent: Carla Connelly (352-805-8650)
3208 SAILING PIER AVE, WINTER GARDEN, FL 34787
$1,049,90046 Days on yellowkey MLS ID: O6402332
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3998 Built: 2023Monthly Fee: $208 Tax: $12,135 (2024)Community: Ests/Lakeview PreserveSingle Family
Taxes:$12,135
Tax Year: 2024
Remarks: Welcome to 3208 Sailing Pier Ave, the original model home at The Estates at Lakeview Preserve. Built in 2023, this stunning residence offers 5 bedrooms, 4 bathrooms, and nearly 4,000 square feet of living space. It is being sold fully furnished with designer-selected pieces, representing turnkey luxury at its finest. The first level features an open-concept layout filled with natural light, a chef-style kitchen with quartz countertops and a walk-in pantry, a spacious living and dining area, a private flex room, and a serene and elegant primary suite. Two additional bedrooms are also located on the first floor. The second level offers a second living area, two more bedrooms, and a beautifully furnished family/game room, perfect for entertaining and relaxing. As a former model home, every detail was professionally designed, and all furnishings are included. The expansive backyard provides the perfect space to create your dream outdoor oasis. Located in the gated community of Estates at Lakeview Preserve, residents enjoy resort-style amenities including a pool, clubhouse, fitness center, playground, and scenic lakeside trails. The home is just minutes from SR-429, Disney, Winter Garden Village, and top-rated schools. Move-in ready and meticulously maintained, this home offers exceptional style, convenience, and value. Schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Mireille Stewart (786-553-6246)
16754 OAKBORO ST, WINTER GARDEN, FL 34787
$535,00034 Days on yellowkey MLS ID: O6404652
REDUCED by $4,000 (0.7%) on 06/05/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2477 Built: 2020Monthly Fee: $254 Tax: $8,808 (2025)Community: Waterleigh Ph 3B 3C 3DSingle Family
Taxes:$8,808
Remarks: Welcome to the highly sought-in the desirable Waterleigh community of Horizon West — where resort-style living meets everyday convenience! From the moment you enter, you’re greeted by a grand, palm tree-lined entrance that sets the tone for a private tropical retreat. Waterleigh is thoughtfully designed around picturesque ponds and lakes, with beautifully maintained landscaping throughout the community — all included in the HOA — making it one of the most visually stunning neighborhoods in the area. Residents enjoy an impressive array of resort-style amenities, including multiple swimming pools, splash pads, a fully equipped fitness center, tennis courts, sand volleyball courts, fishing piers, scenic walking trails, dog parks, and a grand clubhouse with a full-service event hall. This community perfectly balances the feel of a private resort with a warm, welcoming neighborhood atmosphere. This move-in ready home features 4 spacious bedrooms, 3 full and one a half bathrooms,, and approximately 2,477 square feet of living space, offering the perfect blend of comfort, style, and modern design to suit today’s lifestyle. Located in a golf cart-friendly community, the home is just minutes from Publix, top-rated schools, and the best shopping, dining, and entertainment that Horizon West has to offer. Enjoy unbeatable convenience with Walt Disney World only 15 minutes away, Orlando International Airport just 30 minutes away, and quick access to Highway 429 for easy travel throughout Central Florida. Waterleigh also hosts weekly and monthly community events, fostering a strong sense of connection and pride among residents. Don’t miss this rare opportunity to own one of Winter Garden’s most desirable homes — where luxury, convenience, and resort-style living come together. Schedule your private showing today and experience the very best of Waterleigh living!
Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)
Listing Agent: Chun Cai (951-699-4983)
5139 LAKE HAMLIN TRL, WINTER GARDEN, FL 34787
$645,00034 Days on yellowkey MLS ID: O6404614
REDUCED by $10,000 (1.5%) on 06/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2742 Built: 2023Monthly Fee: $271 Tax: $8,755 (2025)Community: Lakeside At HamlinSpa: NoSingle Family
Taxes:$8,755
Elementary School: Hamlin Elementary
Middle School: Hamlin Middle
Remarks: The property boasts a prime location with convenient access to SR 429 and Avalon Road, providing easy connectivity to Horizon West and downtown Winter Garden. The surrounding area continues to experience rapid growth, bringing an exciting mix of new restaurants, entertainment options, and highly rated public and private schools. Whether you are looking for a home that perfectly blends comfort, lifestyle, and location, or seeking an investment opportunity in one of Central Florida’s most sought-after and fast-growing areas, this property is an exceptional choice. Water view home, Davis model, Awesome location in the heart of Horizon West right off the 429 at Independence and Avalon. This 4-2.5 with 2802sf sits right across the street from large pond so you can enjoy sitting on your front porch and take in the scenery. Inside, open floor plan, great room and dining look into the gourmet kitchen, with built in oven, built in cooktop and stove hood. Sink island with breakfast bar. Beautiful tiled back splash, crown molding with white granite counters on white cabinets. First floor master bedroom, large walk-in closet, dual sinks, separate toilet, separate shower and stand alone tub. Second floor has bedrooms 2, 3, and 4 each have walk in closets. Laundry room upstairs with washer and dryer and hall bath. Front large loft through door is 14x20. Off the kitchen is back door to back covered porch and covered walk to garage. This home has 2 ac units for more efficiency, and fiber optic cable and lawn care is included. This community is right near the 429 exit at Independence, near the hospital and tons of new shops and restaurants.
9189 BUSACO PARK WAY, WINTER GARDEN, FL 34787
$1,300,00010 Days on yellowkey MLS ID: O6410698
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3424 Built: 2015Monthly Fee: $158 Tax: $7,174 (2025)Community: Watermark Ph 1BSpa: NoSingle Family
Taxes:$7,174
Elementary School: Panther Lake Elementary
Remarks: Welcome to an exceptional residence where luxury, lifestyle, and location converge in one of Winter Garden’s most desirable communities. Situated on a hard to find oversized premium corner lot, this stunning 4-bedroom, 4-full bath home offers 3,424 square feet of thoughtfully designed living space, perfectly positioned to capture serene park views in the front and tranquil pond vistas in the rear. From the moment you arrive, the home’s elevated presence and expansive setting set the tone. Inside, you are greeted by a light-filled, open-concept layout designed for both elegant entertaining and everyday comfort. The spacious floor plan flows seamlessly, enhanced by refined finishes and generous living areas. At the heart of the home, the kitchen and great room spaces connect effortlessly to the outdoors, where your private resort-style retreat awaits, outdoor living at its finest! Step outside to your private POOL (built in 2022)—a true showpiece designed for relaxation and entertaining. The fully fenced backyard with a sleek metallic fence offers both privacy and unobstructed views, creating the perfect balance of security and openness. Whether hosting gatherings or enjoying a quiet evening, the backdrop of the pond and open skies delivers an unparalleled sense of tranquility. And as the sun sets, prepare for a truly magical experience—nightly views of the MAGIC KINGDOM FIREWORKS right from your backyard create a one-of-a-kind ambiance that elevates everyday living into something extraordinary. INTERIOR HIGHLIGHTS: 4 Bedrooms | 4 Full Bathrooms. A spacious DEN located in the first floor is currently set as a guest room, with the convenience of a full bathroom in the first floor with access to the pool. A spacious BONUS ROOM located on the second floor– ideal for a media room, office, or playroom. Expansive GREAT ROOM and entertaining areas including a STUDY SPACE off of the kitchen and a DINETTE SPACE. A thoughtfully designed layout with functional flow! Recent Update:A/C UNIT REPLACED in late 2025, offering peace of mind and energy efficiency for years to come. Park views from the front – providing openness and privacy. Pond views from the rear – creating a serene and picturesque backdrop. Oversized corner lot enhances curb appeal and outdoor space. This is more than just a home—it’s a lifestyle property that blends natural beauty, luxury amenities, and a prime location. From quiet mornings overlooking the pond to evenings watching Disney fireworks, every day here feels elevated.
Listing Agent: Sulamit Sanchez (305-528-7778)
17552 LAKE STAR RD, WINTER GARDEN, FL 34787
$999,000256 Days on yellowkey MLS ID: O6344668
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 2605 Built: 2023Monthly Fee: $83 Tax: $12,990 (2024)Community: Northlake/Ovation Ph 1Single Family
Taxes:$12,990
Elementary School: Water Spring Elementary
Remarks: Welcome to this stunning brand-new single-story home, perfectly located in the sought-after Horizon West community in Winter Garden. This 4-bedroom, 3-bath residence with a 2-car garage combines modern design, energy efficiency, and a lifestyle of comfort and elegance. Step inside and be amazed by the bright open-concept floorplan, highlighted by natural light and a fresh, modern color palette. The chef’s kitchen is a true showstopper with 42-inch shaker cabinets in light tones, gorgeous quartz countertops, a large island ideal for gatherings, and premium stainless steel appliances—including refrigerator, range, dishwasher, microwave, washer, and dryer. The home’s efficient construction ensures comfort and savings, while the spacious lanai invites you to relax and enjoy serene views of the Star Lake and lush conservation area—your private piece of paradise, right in your backyard. Opportunities like this don’t last long in Horizon West! Don’t miss your chance to own this extraordinary single-story lakeside retreat. Schedule your private showing today and make this dream home yours!
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Daniel Pavel (407-747-3408)
9468 KOMIKA LN, WINTER GARDEN, FL 34787
$459,90014 Days on yellowkey MLS ID: S5150415
0 Days Off yellowkey (back on 6/5/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1705 Built: 2020Monthly Fee: $300 Tax: $7,605 (2025)Community: Waterleigh Ph 3ASingle Family
Taxes:$7,605
Remarks: One or more photo(s) has been virtually staged. 9468 Komika Lane is the kind of home that makes people slow down when they drive by. Between the curb appeal, charming front elevation, and rear-entry garage - a feature you rarely find in Florida - this 3-bedroom, 2-bath home stands out from the moment you arrive. Located in Waterleigh, the community offers the kind of amenities people actually use: a swimming pool, clubhouse, fitness center, sports courts, dog park, and playground - creating the feeling of a neighborhood where weekends don’t always require leaving home. Everyday conveniences are close by with Publix near the community entrance, plus shopping, dining, coffee spots, and entertainment around Flamingo Crossings, Hamlin, and Winter Garden Village. And when you want a little extra magic, Walt Disney World is close enough for spontaneous fireworks nights, resort dinners, or quick park days without turning it into an all-day event. *Some marketing images have been AI-assisted and virtually staged to illustrate the property’s potential layout, design, use of space, and possible aesthetic enhancements. Certain photos may include digitally enhanced visualization of furnishings, décor, finishes, landscaping, or cosmetic elements for marketing and illustrative purposes only. Actual property conditions, features, finishes, fixtures, and appearance may vary, and buyers are encouraged to independently inspect the property to verify all present conditions.*
Listing is courtesy of: PROFESSIONAL REAL ESTATE TEAM (407-483-4964)
Listing Agent: Jany Perez (407-483-4964)
16283 HONEY HARVEST ST, WINTER GARDEN, FL 34787
$649,00054 Days on yellowkey MLS ID: O6399528
REDUCED by $21,000 (3.1%) on 06/04/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2927 Built: 2024Monthly Fee: $229 Tax: $9,705 (2025)Community: Harvest/OvationSingle Family
Taxes:$9,705
Remarks: One or more photo(s) has been virtually staged. This 2024-built Baldwin in Harvest at Ovation offers nearly 2,900 total square feet with 5 bedrooms and 4.5 bathrooms, *set on a premium CONSERVATION LOT with no rear neighbors.* The main home features an open-concept layout with a first-floor bedroom and en suite full bath, spacious living and dining areas, and a gourmet kitchen with quartz countertops, upgraded cabinetry, and a walk-in pantry. Above the garage, a fully detached private suite adds approximately 530 square feet, complete with its own entrance, living area, kitchenette, bedroom, and full bath - ideal for guests, multigenerational living, or a private workspace. Located minutes from Walt Disney World, Hamlin Town Center, and Flamingo Crossings in one of Horizon West’s most desirable communities.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
241 N DILLARD ST, WINTER GARDEN, FL 34787
$1,499,999233 Days on yellowkey MLS ID: O6353975
REDUCED by $100,001 (6.3%) on 04/13/2026
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3507 Built: 1953 Tax: $2,959 (2024)Community: J L Dillard Sub 3Single Family
Taxes:$2,959
Elementary School: Dillard Street Elem
Middle School: Lakeview Middle
Remarks: Seller financing opportunity!!! Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden. Set on a lot boasting an expansive 214 feet of frontage, a rare and highly sought after feature that enhances both privacy and presence. 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.
8955 LAKESHORE POINTE DR, WINTER GARDEN, FL 34787
$639,990285 Days on yellowkey MLS ID: O6337042
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2539 Built: 2018Monthly Fee: $600 Tax: $8,886 (2024)Community: Lakeshore Preserve Ph 1Townhouse
Taxes:$8,886
Remarks: Welcome to this elegant and beautiful townhome, fresh interior paint throughout and designed by an architect. This property is being offered for the first time since its original purchase in 2018. It has an open concept, full of upgrades and details. Wall papers bring a cozy atmosphere and elevate harmony. This home has ceiling speakers, security camera and ring door bell. As you walk in you feel the modern layout with a charming patio to enjoy family, friends and Florida weather. Main level with kitchen, 1/2 bath, living and dining area. At the living area you can enjoy the natural light, lovely crown-molding, and blinds for privacy. A Wine Refrigerator adds a touch of elegance. Dining area with wall paper and Borserie. Beautiful 1/2 Bath with wall paper. Sophisticated gourmet kitchen with granite, backsplash, gray color cabinets, double sink and spacious kitchen island. Sliding doors bring extra natural light and take you to back patio. Upgraded stairs to second floor with a cozy carpet. Elegant Master Bedroom with wall paper, and walk in closet. Master Bathroom with 2 sinks, niche, shower inclosure, shower tiles up to ceiling, private commode, and handheld private bided. Extra two bedrooms, with wall paper, brand new custom closets, blinds and curtains. Second bathroom with niche, shower enclosure, creme color cabinet, 2 sinks and handheld toilet bidet. Laundry room with granite, cabinet and laundry sink. The surprise is the additional bonus apartment on top of garage with mini kitchen, full bathroom, wall paper, blinds and walk in closet. To wrap this masterpiece listing, a 2 car garage with epoxy. Sellers never lived at the property, as it was their secondary home. Seller is giving a new kitchen refrigerator as credit at closing. Schedule a tour as you will fall in love! There is a you tube link with a video of the property!
Listing is courtesy of: ANA TEIXEIRA REALTY (321-624-4325)
Listing Agent: Ana Paula Teixeira (321-624-4325)
9355 TYRELLA PINE TRL, WINTER GARDEN, FL 34787
$459,00077 Days on yellowkey MLS ID: O6391856
REDUCED by $8,000 (1.7%) on 05/30/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1670 Built: 2016Monthly Fee: $148 Tax: $657 (2025)Community: Watermark Ph 1BSingle Family
Taxes:$657
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. PRICE REDUCTION - SELLER SAYS "BRING OFFERS" Experience the perfect blend of modern upgrades and an unbeatable location in this move-in-ready 3-bedroom, 2.5-bathroom home within the premier Watermark community. This residence has been meticulously maintained, boasting exterior paint (2023), a new garage lift (2024), and a brand-new water heater (2025). The home welcomes you with a huge covered front porch and an open-concept first level featuring tile flooring throughout, a chef-inspired kitchen with stainless steel appliances, rich cabinetry, and a breakfast bar. Upstairs, a versatile loft and convenient laundry room connect the primary suite to two generously sized guest bedrooms. Residents enjoy world-class community amenities including a resort-style pool, fitness center, tennis courts, and playground, all while being walking distance to the brand-new "The Mark" shopping center. Perfectly situated for families and commuters alike, zoned for Top Rated Schools, and just minutes from Hamlin Town Center, the 429 expressway, and Disney property. With alley-access parking and easy access to Winter Garden’s unique charm, this home offers the ultimate Horizon West lifestyle. Tour today! SOLAR PANELS ARE PAID IN FULL!
Listing is courtesy of: REDFIN CORPORATION (407-708-9747)
Listing Agent: Jo Holton (307-690-7219)
16783 TURTLE HATCH DR, WINTER GARDEN, FL 34787
$1,199,99933 Days on yellowkey MLS ID: O6404708
REDUCED by $1 (0.0%) on 05/20/2026
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3513 Built: 2019Monthly Fee: $240 Tax: $13,161 (2025)Community: Waterside/Johns Lk-Ph 1Single Family
Taxes:$13,161
Remarks: An exceptional expression of refined living, this luxury estate is nestled within the exclusive gated enclave of Waterside at Johns Lake in Winter Garden. Boasting 5 bedrooms and 5.5 baths, this impeccably designed residence showcases a seamless blend of sophistication and comfort. The expansive open-concept layout is enhanced by elegant wood plank tile flooring throughout the main level and anchored by a chef-inspired gourmet kitchen, thoughtfully appointed for both everyday living and upscale entertaining. The lavish primary suite serves as a private sanctuary, featuring a spa-caliber bath and an oversized walk-in closet designed to impress. Step outside to your own resort-style retreat, where a screened-in pool and spa create the perfect setting for relaxation, complete with a dedicated pool bath for added convenience. The upper level offers a versatile bonus room along with a private guest suite, providing ideal accommodations for visitors or multigenerational living. Distinguished features include a 3-car garage, stately slate tile roof, charming courtyard entry, and a fully integrated irrigation system—every detail curated for both elegance and ease. Residents enjoy access to an array of resort-style amenities, including a clubhouse, state-of-the-art fitness center, community pool, fishing dock, scenic walking paths, parks, and playgrounds. Perfectly positioned just minutes from the charm of Historic Downtown Winter Garden, Winter Garden Village, Hamlin, and Horizon West, with convenient access to major thoroughfares and Central Florida’s premier attractions
Listing is courtesy of: SIERRA REALTY GROUP LLC (407-557-3119)
Listing Agent: Sylvester Harding (407-557-3119)
13526 FOX GLOVE ST, WINTER GARDEN, FL 34787
$845,00078 Days on yellowkey MLS ID: O6388630
1 Days Off yellowkey (back on 5/1/2026)
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3866 Built: 2005Monthly Fee: $243 Tax: $11,960 (2025)Community: Stoneybrook WestSpa: YesSingle Family
Taxes:$11,960
Remarks: Under contract-accepting backup offers. Homes of this size, FULLY REMODELED, with a HEATED POOL, SOLAR PANEL and beautiful views rarely become available in this highly sought-after GATED COMMUNITY in Winter Garden. Featuring 24-hour GUARD-GATED SECURITY, resort-style amenities, exclusive access to Black Lake, golf course and on-site restaurant; this community truly offers a lifestyle like no other. With a TOP-RATED elementary school just across the street — kids often ride their bike, scooter, or even golf cart to school — and an unmatched community atmosphere, this is a rare opportunity. | This beautifully updated home offers 5 bedrooms, 3 bathrooms, and 3,866 square feet of thoughtfully designed living space. Fully renovated on the inside, it also features a NEW ROOF, solar panels, and fresh exterior paint. Even better, the home is being sold FULLY FURNISHED, offering a true turnkey experience so you can move in and start enjoying it from day one. | FIRST FLOOR includes a bedroom and a full bath, SECOND FLOOR includes the Master Bedroom, three other bedrooms and one additional full bath; you also have a massive loft creating endless possibilities — movie room, game room, or an additional living area tailored to your lifestyle. | Step outside to your private heated pool and amazing sunrise views. This home also includes a spacious THREE CAR GARAGE featuring epoxy flooring and ELECTRIC VEHICLE CHARGING STATION, sink and fridge. | Residents of this community enjoy an exceptional array of amenities, including multiple pools, tennis, basketball, volleyball, and pickleball courts, playgrounds, and private fishing piers. With direct access to Black Lake, it’s ideal for boating and jet ski enthusiasts, while golf lovers can take advantage of the on-site course with resident-friendly membership options. | Ideally situated just minutes from Winter Garden Village, offering a wide variety of shops and restaurants, with quick access to the State Road 429, and only 10 minutes from both Downtown Historic Winter Garden and the growing Hamlin district, this home perfectly balances convenience and lifestyle. Homes like this — FULLY RENOVATED, ENERGY EFFICIENT, FULLY FURNISHED, AND WITH THIS LEVEL OF SPACE & UPGRADES ARE RARELY AVAILABLE IN THIS COMMUNITY. (Click on Virtual Tour Link 1 for complete tour)
Listing Agent: Mariana Cezar Ovalle (407-427-3559)
68 N PARK AVE, WINTER GARDEN, FL 34787
$1,799,00054 Days on yellowkey MLS ID: O6400066
REDUCED by $50,000 (2.7%) on 06/05/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3555 Built: 2021Monthly Fee: $325 Tax: $15,594 (2025)Community: 30 North ParkTownhouse
Taxes:$15,594
Elementary School: Tildenville Elem
Remarks: Experience the ultimate in luxury urban living at 68 N Park Ave, a stunning 3-story townhome with rooftop deck located in the heart of Historic Downtown Winter Garden. This sophisticated 4-bedroom, 4.5-bathroom residence offers over 3,500 sq. ft. of meticulously designed space, seamlessly blending modern elegance with the charm of the historic district. The open-concept main level features soaring 11-foot ceilings, expansive industrial-style windows, and a chef’s dream kitchen equipped with an oversized quartz island, natural gas appliances, and custom artisan cabinetry. Accessibility is effortless with your own private elevator serving all floors. Retreat to the third-floor master suite, featuring a spa-inspired bath and massive walk-in closet, or host guests in the versatile first-floor bedroom suite. The "wow factor" continues on the 1,200 sq. ft. private rooftop terrace, offering panoramic views of the city skyline—the perfect spot for evening cocktails or watching local fireworks.Location is everything. Leave your car in the 2-car garage and embrace the golf-cart-friendly lifestyle. You are just steps away from: The award-winning Winter Garden Farmers Market, The vibrant Plant Street Market and Crooked Can Brewing Co, The world-class West Orange Trail for biking and running, Boutique shopping, fine dining, and the historic Garden Theatre. Don’t miss this rare opportunity to own a piece of downtown luxury. Schedule your private showing today!
Listing is courtesy of: VISTA CAY REALTY COMPANY (407-996-4656)
Listing Agent: Mauro Costa (321-231-6800)
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