Location: Winter Garden
Keyword(s): West Orange High
Keyword(s) High School: West Orange High
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2107 REDMARK LN, WINTER GARDEN, FL 34787
$649,90020 Days on yellowkey MLS ID: O6423037
0 Days Off yellowkey (back on 7/10/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2826 Built: 2009Monthly Fee: $90 Tax: $10,319 (2025)Community: Carriage Pointe A-I & LSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,319
Elementary School: Whispering Oak Elem
High School: West Orange High
Tax Year: 2025
Middle School: Hamlin Middle
Remarks: Under contract-accepting backup offers. Welcome to this beautifully maintained residence in the highly sought-after gated community of Carriage Pointe in Winter Garden. Built in 2009, this spacious residence offers 2,826 square feet, 4 bedrooms, 3 full bathrooms, and a full 3-car garage, all thoughtfully designed around an ideal three-way split floor plan that provides privacy and flexibility for families and guests alike. From the moment you arrive, you'll be welcomed by a charming covered front porch complete with a porch swing—the perfect place to relax and enjoy the neighborhood. Inside, soaring ceilings, plantation shutters, engineered hardwood flooring throughout the main living areas, updated lighting and ceiling fans, and elegant crown and chair rail molding in the formal dining room create a warm and inviting first impression. Formal living and dining rooms greet you at the front of the home before opening into the heart of the house. The spacious kitchen is designed for both everyday living and entertaining, featuring granite countertops, an oversized island with bar seating, stainless steel appliances, 42-inch upper cabinets with crown molding, a decorative herringbone tile backsplash, and abundant cabinet and counter space. The kitchen flows seamlessly into the expansive great room, where large sliding glass doors showcase one of the home's most spectacular features—the private backyard oasis. Step outside to your own resort-style retreat featuring a gas-heated saltwater plunge pool, an expansive covered lanai, and a fully fenced backyard. The elevated homesite overlooks peaceful conservation with no rear neighbors, creating exceptional privacy and a boutique resort feel that's rarely found. Whether you're enjoying a quiet morning coffee or entertaining friends and family, this outdoor living space is truly the centerpiece of the home. The spacious primary suite is privately situated at the rear of the home and enjoys tranquil backyard views, a tray ceiling, abundant natural light, a custom-designed walk-in closet, and private access to the covered lanai. The luxurious primary bathroom features separate vanities, a garden tub, and an oversized walk-in shower. The thoughtfully designed three-way split floor plan offers exceptional privacy, with one guest bedroom and full bath tucked away near the center of the home, while two additional bedrooms share a full pool bath with direct access to the outdoor living area. Additional upgrades include a brand-new roof (2026), AC (2023), and water heater (2022)—meaning all of the home's major mechanical systems have already been updated, providing tremendous peace of mind for the next owner. The oversized 3-car garage is equally impressive with premium Husky storage cabinets, wall-mounted organization systems, two ceiling-mounted storage racks, and wiring already in place for a future electric vehicle charger. Additional improvements include whole-house surge protection and a spacious interior laundry room complete with a utility sink and upper cabinetry. Residents of Carriage Pointe enjoy the security of two gated entrances along with community amenities including a playground, tennis court, and soccer field. Conveniently located near Winter Garden's shopping, dining, major roadways, and top-rated schools, this exceptional home offers the perfect combination of thoughtful upgrades, resort-style outdoor living, and peaceful conservation views. Make an appointment so see this home today!
Listing is courtesy of: THE WILKINS WAY LLC (407-874-0230)
Listing Agent: William Wygle (407-375-9005)
13412 FOX GLOVE ST, WINTER GARDEN, FL 34787
$829,900121 Days on yellowkey MLS ID: G5110319
REDUCED by $20,000 (2.4%) on 07/10/2026
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3954 Built: 2005Monthly Fee: $243 Tax: $5,889 (2025)Community: Stoneybrook West Un 06Spa: YesSingle Family
Taxes:$5,889
Middle School: SunRidge Middle
Remarks: WOW!!! OVER $60,000 RECENT PRICE REDUCTION!! BRAND NEW AC SYSTEM INSTALLED LAST WEEK (7/2/26) Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. The property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Juli Onorata (407-864-7701)
2241 WHITE FEATHER LOOP, WINTER GARDEN, FL 34787
$525,00059 Days on yellowkey MLS ID: O6411576
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2152 Built: 2018Monthly Fee: $105 Tax: $4,991 (2025)Community: Oakland Trls Ph 1Single Family
Taxes:$4,991
Elementary School: Tildenville Elem
Middle School: Lakeview Middle
Remarks: Welcome to Oakland Trails, one of Oakland’s most desirable communities! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect blend of comfort, style, and location. Built in 2018, the home features a bright, open-concept floor plan with spacious living areas, a modern kitchen, and plenty of room for both everyday living and entertaining. Step outside and enjoy all the amenities that make Oakland Trails so special, including a resort-style community pool and playground. Outdoor enthusiasts will love being just minutes from the renowned West Orange Trail, offering miles of scenic paths for walking, running, and biking through some of Central Florida’s most beautiful landscapes. Conveniently located near historic downtown Winter Garden, shopping, dining, and major roadways, this home combines small-town charm with everyday convenience. Whether you're relaxing at the pool, exploring the nearby trail system, or enjoying all that the area has to offer, this property delivers the Florida lifestyle you've been looking for.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Brynn Allen (407-617-8963)
720 LAKE BRIM DR, WINTER GARDEN, FL 34787
$1,699,000145 Days on yellowkey MLS ID: O6387519
1 Days Off yellowkey (back on 7/9/2026)
REDUCED by $26,000 (1.5%) on 06/14/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3781 Built: 2020Monthly Fee: $208 Tax: $14,831 (2025)Community: Oakland ParkSpa: NoSingle Family
Taxes:$14,831
Remarks: Under contract-accepting backup offers. PARADE of HOMES-OAKLAND PARK! Experience refined Florida living in the heart of Winter Garden, where timeless architecture, thoughtful design, & an unbeatable location come together in this exceptional custom-built residence. Situated on an expansive corner lot (~1/4 acre) overlooking one of the community’s most beloved PARKS, this four-bedroom (w/ room for a 5th & office), four-bath luxury HEATED POOL home offers privacy, space, & picturesque views. You’re moments from stunning sunsets, a walk by the LAKE, multiple parks & playgrounds, the community clubhouse, & direct access to the scenic WEST ORANGE TRAIL— a 22-mile paved trail ideal for biking, jogging, & casual strolls. From the moment you arrive, the stunning brick-accented front porch sets the tone, offering a welcoming space to relax while enjoying tranquil park views. Inside, rich wood flooring flows throughout the main living areas, complementing the home’s elevated finishes, such as crown molding, wainscoting, trim work, & custom built-ins. The chef’s kitchen is a true showpiece. Outfitted with premium Thermador & JennAir appliances, QUARTZITE counters, custom cabinetry, designer fixtures, a walk-in pantry, & spacious gathering space, this kitchen was designed for both everyday living & elegant entertaining. The adjacent dining & living areas are bathed in natural light, enhanced by multiple French doors that frame panoramic views of the pool and backyard retreat. The indoor-outdoor connection is simply spectacular. Step outside to your private oasis featuring a sparkling resort-style pool (runs with an ozonator) with travertine decking, generous covered lanai, & an outdoor kitchen equipped with a mini fridge & 48 inch griddle. Each of the four bedrooms is generously sized, offering comfort & versatility for family & guests. One generously sized bedroom is downstairs, which has access to the pool & park through French doors. The primary suite serves as a luxurious retreat with a spa-like bath & dual closets, while all four baths (three en-suite) are thoughtfully designed with quality finishes (marble upstairs, quartzite downstairs). Need an elevator? There's space for the addition! A well-appointed MUDROOM adds everyday convenience & organization, seamlessly blending practicality with style. Additional FEATURES: whole house water filtration system, in-ceiling speakers in the living room, the lanai by the pool, & front porch, tankless water heaters, hard wired cameras inside/out, ample storage, landscape lighting, Cat 6 wiring w/ WiFi access points, & an OVERSIZED garage (~2 1/2). Just a short GOLF CART ride away, you’ll find the charm & vibrancy of Historic Downtown Winter Garden, known for its award-winning restaurants, boutique shopping, outdoor dining, farmers market, & events. This is more than a home — it’s a lifestyle defined by luxury, walkability, community connection, & the unmatched charm of Winter Garden living. This golf-cart-approved WATERFRONT community offers year-round activities, from golf cart parades to book clubs & social gatherings, making it an extraordinary place to call home. The community features parks, playgrounds, two pools, a clubhouse, dog park, & trails. Don’t miss this opportunity to live in one of the areas most sought-after neighborhoods, with easy access to interstate travel, shops, restaurants, golf courses, & world-renowned theme parks. Custom built POOL homes are RARE to market in Oakland Park. Make this DREAM home your reality today!
Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)
Listing Agent: Ashley Boyd (321-209-5540)
346 CRYSTAL WOOD DR, WINTER GARDEN, FL 34787
$899,00020 Days on yellowkey MLS ID: O6423640
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3147 Built: 2026Monthly Fee: $240 Tax: $1,955 (2025)Community: Winter GroveSpa: NoSingle Family
Taxes:$1,955
Elementary School: SunRidge Elementary
Remarks: Under Construction. Welcome to Winter Grove in the charming city of Winter Garden. Located 1 mile from Winter Garden Village and 3 miles from historic downtown Winter Garden. This intimate gated new community features single-family homes on large homesites without a CDD. Residents enjoy all the proximity to shopping, dining, and entertainment this area is known for. The beautifully designed 4 bedroom with an enclosed flex room, 3 bathroom, 2 car garage Coral Grand home offers the perfect blend of luxury, comfort, and functionality. As you step inside, you are greeted by a grand foyer that opens to the second floor, creating an inviting and open atmosphere. To your one side, a spacious secondary bedroom and full bath provide ideal accommodations for guests. Adjacent, an enclosed flex room offers endless possibilities – whether it’s a private office, hobby room, or a cozy reading nook. Travel deeper into the heart of the home, and you’ll find an expansive open concept layout that seamlessly connects the gathering room, kitchen, and cafe. Large windows throughout the main living areas flood the space with natural light, creating a warm and welcoming ambiance. The chef’s dream kitchen is a showstopper, complete with a built-in cooktop, stainless steel appliances, quartz countertops, and soft-close cabinetry. Step outside to enjoy the covered lanai, complete with two sliding glass doors that create a seamless transition between indoor and outdoor living. The owner's suite, located conveniently on the first floor, provides a private retreat with ample space, and is complemented by a luxurious en-suite bathroom with a spa-like walk-in shower with rain shower head, a quartz-topped dual vanity, a private water closet, and an expansive walk-in closet. The laundry room is also thoughtfully located on the first floor, complete with built-in cabinetry and a quartz trimmed utility sink, adding to the home’s convenience and ease of living. Upstairs, you’ll find two additional bedrooms, a full bathroom, and a spacious loft, offering plenty of room for everyone. Shaw wood-look luxury vinyl plank spans the first floor living areas and owner’s suite, beautiful tile flooring adds durability in the bathrooms, and laundry room, and plush, stain-resistant carpet covers the upstairs loft and secondary bedrooms. For those who appreciate the convenience of technology, this home comes equipped with a smart thermostat, video doorbell, and LED downlights, ensuring your home is as connected as it is beautiful. Experience the luxury of modern living with timeless design – schedule a tour today and see all that this exceptional home has to offer!
Listing is courtesy of: PULTE REALTY OF NORTH FLORIDA LLC (407-250-9131)
Listing Agent: Adrienne Escott (407-250-9131)
14067 JOMATT LOOP, WINTER GARDEN, FL 34787
$1,099,00021 Days on yellowkey MLS ID: O6422734
Bed: 6 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4741 Built: 2018Monthly Fee: $75 Tax: $7,802 (2026)Community: Cypress Reserve Ph 2Spa: NoSingle Family
Taxes:$7,802
Tax Year: 2026
Remarks: Experience luxury living in this exceptional 6-bedroom, 5-bathroom residence located in the highly sought-after Cypress Reserve community of Winter Garden. Perfectly positioned on a premium homesite with no rear neighbors, this impressive home offers exceptional privacy, tranquil conservation views, and a versatile floor plan designed for today’s lifestyle. The open-concept design showcases beautifully appointed living spaces throughout both floors, making it ideal for multigenerational living or hosting extended family and guests. A dramatic second-floor loft overlooks the main living area, creating an open and inviting atmosphere while providing additional living space. Upstairs also features a second primary suite, three additional spacious bedrooms, a dedicated theater/media room, and a flex room that serves perfectly as a home office, den, or playroom. At the heart of the home is a chef-inspired gourmet kitchen designed to impress, featuring stainless steel appliances, a gas cooktop, double wall ovens, quartz countertops, and an oversized center island with an undermount sink, generous seating, and double-sided cabinetry that provides exceptional storage for both everyday living and entertaining. Motorized shades throughout the main living area add a touch of sophistication and everyday convenience. The spacious family room opens effortlessly to the outdoor living space through triple pocket sliding glass doors, creating a seamless indoor-outdoor lifestyle. Relax year-round on the screened lanai overlooking peaceful conservation views or entertain with ease around the sparkling pool and fully equipped outdoor kitchen featuring a Paradise Grill, built-in sink, and refrigerator. Luxurious owner's suite is a private retreat featuring a spa-inspired bath with dual vanities, a relaxing garden tub, a zero-entry walk-in shower with seamless glass enclosure, and double-door entry to an expansive custom-designed walk-in closet that is sure to impress. A private hallway just off the main living area leads to a spacious guest suite with direct access to the pool, along with a generously sized laundry room for added convenience. Upstairs, you'll find a second primary suite, three additional bedrooms, an expansive loft, a dedicated theater/media room, and a versatile flex room—offering abundant space for family, guests, a home office, fitness room, or additional living area. Additional highlights include a three-car tandem garage offering abundant storage and ample room for a home gym, workshop, or hobby space. LOCATED just minutes from Downtown Winter Garden, the award-winning Winter Garden Farmers Market, Winter Garden Village, shopping, dining, top-rated schools, and major roadways including State Road 429 and Florida’s Turnpike, this exceptional home offers the perfect blend of luxury, comfort, convenience, and location *** This is a rare opportunity to own one of Cypress Reserve’s premier residences and experience the very best of the Winter Garden and true Florida lifestyle. ***
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Kimberly Beach Byerly (407-516-7780)
225 SOUTHERN PECAN CIR #208, WINTER GARDEN, FL 34787
$279,900147 Days on yellowkey MLS ID: O6383422
REDUCED by $9,000 (3.1%) on 07/08/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1264 Built: 2005 Tax: $3,728 (2025)Community: Southern Pines CondoCondo
Taxes:$3,728
Remarks: Beautiful 2-bedroom, 2-bathroom condo just under 1,300 sq ft in one of the most desirable areas of Winter Garden. Both bedrooms feature large walk-in closets, and the layout is exceptionally well designed, making the home feel spacious and comfortable. The unit COMES WITH A 1-CAR GARAGE, a rare and valuable feature. All appliances are BRAND NEW, including refrigerator, microwave, stove, and dishwasher. A washer and dryer are also included. The flooring has been completely renovated to elegant wood flooring throughout. The main living area offers a separate flex space that is PERFECT for a home office or a kids’ play area. Conveniently located next to the community car wash, with resort-style amenities that include an amazing clubhouse, pool area with barbecue grills, fully equipped gym, tennis courts, basketball courts, and more.
Listing is courtesy of: JOHN SILVA REALTY & ASSOCIATES (407-420-7908)
Listing Agent: John Silva (407-420-7908)
243 ZACHARY WADE ST, WINTER GARDEN, FL 34787
$1,300,000132 Days on yellowkey MLS ID: O6391909
REDUCED by $74,500 (5.4%) on 07/08/2026
Bed: 5 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3097 Built: 2004Monthly Fee: $58 Tax: $6,565 (2025)Community: Lakeview Reserve 46/149Single Family
Taxes:$6,565
Remarks: PRICE IMPROVEMENT! Refined Waterfront Living in Winter Garden’s Coveted Golf Cart District! Set within one of Downtown Winter Garden’s most desirable gated enclaves, this exceptional waterfront residence offers a rare blend of sophistication, privacy, and effortless Florida living—perfectly positioned in the highly sought-after golf cart district. Designed to maximize light and livability, the interiors are bright and inviting. Recent enhancements include new exterior paint (2026), a tankless water heater (2026), and a added ensuite bathroom (2026) making two primary suites on the second floor. Generous storage is thoughtfully integrated with expansive closet space, while a whole-home water softener and purification system, including an under-sink filter, ensures elevated everyday comfort. At the heart of the home, the gourmet kitchen is both functional and beautifully appointed, featuring dual sinks, a dedicated prep island, and upgraded soft-close cabinetry. The oversized three-car garage provides ample room for vehicles, storage, or recreational needs. Outdoors, the lifestyle truly unfolds. A recently resurfaced covered boat dock—complete with lift, lighting, fan, and sink—offers direct access to one of Florida’s largest spring-fed lakes, part of the Harris Chain and extending to the St. Johns River and Atlantic Ocean. The expansive grounds are enriched by mature, fruit-bearing trees including mango, avocado, star fruit, and citrus, creating a lush, private retreat. Surrounded by natural beauty, the property attracts an impressive array of wildlife. Unforgettable sunrises and sunsets can be enjoyed from multiple vantage points, including the living spaces, patio, dock, and three north-facing bedrooms with water views. This is a home that seamlessly balances elegance and ease—offering a rare opportunity to experience serene waterfront living in one of Winter Garden’s most iconic settings.
Listing is courtesy of: REGENCY REAL ESTATE LLC (407-469-5021)
Listing Agent: Alexis Anderson (561-670-5901)
13759 GOLDEN RUSSET DR, WINTER GARDEN, FL 34787
$309,00069 Days on yellowkey MLS ID: O6409757
REDUCED by $19,500 (5.9%) on 07/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1647 Built: 2007Monthly Fee: $333 Tax: $855 (2025)Community: Orchard A1-A26 B1 B2 C D1-D4Townhouse
Taxes:$855
Remarks: This home provides modern comfort, thoughtful design, and an unbeatable Winter Garden location. This beautifully maintained home features an open and inviting floor plan with plenty of natural light, creating a warm and welcoming atmosphere from the moment you walk in. The spacious kitchen is designed for both everyday living and entertaining, complete with generous counter space, ample cabinetry, and seamless flow into the main living areas. The bedrooms provide flexibility for family, guests, or a home office setup, while the primary suite provides a relaxing private escape with well appointed finishes and plenty of space to unwind. The photos of the living room and bedrooms have been virtually staged to showcase the home's beautiful potential and help buyers envision the possibilities. Enjoy living just minutes from shopping, dining, entertainment, and top rated schools, with convenient access to Hamlin, downtown Winter Garden, Disney, and major roadways throughout Central Florida. Residents also enjoy community amenities including a pool area, playground, scenic surroundings, and a strong sense of community. This is an incredible opportunity to own a home in one of Winter Garden’s most sought after locations.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
15680 ORANGE HARVEST LOOP, WINTER GARDEN, FL 34787
$530,00026 Days on yellowkey MLS ID: O6422130
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2011 Built: 2016Monthly Fee: $365 Tax: $6,270 (2025)Community: Hickory Hammock Ph 1CTownhouse
Taxes:$6,270
Remarks: Welcome to your own private retreat, where every day feels like a vacation. Nestled within a gated community with no direct rear neighbors, providing added privacy and open space behind the home, this beautifully maintained 3-bedroom, 2.5-bath townhouse, built in 2016, offers over 2,200 square feet of thoughtfully designed living space, a spacious 2-car garage, and premium upgrades throughout. The monthly HOA fee of just $366 provides exceptional value while supporting the community's outstanding amenities and low-maintenance lifestyle. This exceptional home features a whole-house water filtration system, durable epoxy-coated garage floors, and double-pane, hurricane-impact tinted windows that provide enhanced energy efficiency, comfort, storm protection, and added privacy. From the moment you step inside, you'll feel right at home. The open-concept floor plan is warm and inviting, creating the perfect setting for everyday living and unforgettable gatherings. The modern kitchen flows effortlessly into the spacious living and dining areas, making it easy to stay connected with family and friends. Step outside to your private covered lanai, where you can enjoy your morning coffee, unwind after a long day, and relax in the privacy of your backyard with no direct rear neighbors—the perfect setting for peaceful mornings, quiet evenings, and enjoying the beauty of nature. Upstairs, a generous loft provides the flexibility today's homeowners desire. Whether you envision a cozy media room, productive home office, children's playroom, fitness area, or a second family room, this versatile space easily adapts to your lifestyle. Beyond your front door, you'll discover a community designed for relaxation and recreation. Residents enjoy resort-style amenities, including a sparkling swimming pool, an elegant clubhouse, scenic walking trails, a private boat dock with beautiful water views, and a family-friendly park with open green spaces perfect for picnics, outdoor activities, and creating lasting memories. Perfectly located, this home offers the ideal blend of convenience, privacy, and low-maintenance living. Families will appreciate the proximity to Whispering Oak Elementary, Hamlin Middle School, and West Orange High School. You'll also be just minutes from healthcare facilities, Publix, shopping, dining, entertainment, and major highways, making commuting throughout Central Florida quick and convenient. Whether you're searching for your first home, upgrading your lifestyle, or looking for the perfect low-maintenance retreat, this home offers more than just beautiful living space—it offers comfort, quality, and a place where lasting memories are made. Move in with confidence and enjoy the perfect combination of modern upgrades, resort-style amenities, and a prime location. Schedule your private showing today and discover why this exceptional home is the perfect place to begin your next chapter.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Fina Perez (407-780-6680)
217 W STORY RD, WINTER GARDEN, FL 34787
$450,00036 Days on yellowkey MLS ID: O6417750
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1952 Tax: $6,017 (2025)Community: Pleasant ParkSpa: NoSingle Family
Taxes:$6,017
Elementary School: Dillard Street Elem
Remarks: Welcome to 217 W. Story Road, a beautifully located home in Downtown Winter Garden, Florida, offering the walkable, golf cart friendly lifestyle that has made Winter Garden real estate some of the most sought after in Central Florida. Situated just a few blocks from the iconic Plant Street Market, this home places you in the center of everything that makes historic Downtown Winter Garden one of the area's premier destinations. Enjoy convenient access to local restaurants, boutique shopping, coffee shops, breweries, and the award winning West Orange Trail. Spend your weekends at the popular Winter Garden Farmers Market, live entertainment events, and seasonal festivals, all just minutes from your front door. Located in the highly desirable golf cart district, residents can easily access Downtown Winter Garden's newest restaurants and exciting developments that continue to enhance the area's charm and long term appeal. With close proximity to Winter Garden Village, major highways, Walt Disney World, and all that Central Florida has to offer, this location combines small town character with modern convenience. Whether you're searching for a home near Plant Street Market, a property in the golf cart district, or a home in historic Downtown Winter Garden, 217 W. Story Road offers a rare opportunity to experience one of the most desirable lifestyles in Winter Garden, FL.
Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)
Listing Agent: Matthew Mckee (407-948-0658)
15340 OAK APPLE COURT CT #16B, WINTER GARDEN, FL 34787
$350,00034 Days on yellowkey MLS ID: O6419809
0 Days Off yellowkey (back on 7/3/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1544 Built: 2008Monthly Fee: $282 Tax: $4,127 (2025)Community: Tucker Oaks Condo Ph 4Condo
Taxes:$4,127
Remarks: Under contract-accepting backup offers. Welcome to Tucker Oaks, one of Winter Garden's most desirable gated communities! This beautifully maintained 3-bedroom, 2.5-bathroom townhome-style condo offers 1,544 square feet of comfortable living space, an attached two-car garage providing secure parking and additional storage, and a prime location just minutes from Historic Downtown Winter Garden. Step inside to discover a bright and inviting interior featuring laminate flooring installed throughout the living areas and bedrooms, complemented by ceramic tile in the kitchen and bathrooms. Fresh interior paint creates a clean, modern feel, while crown molding adds an elegant touch to the main living area. The well-appointed kitchen is designed for both style and function, featuring granite countertops, 42-inch cabinetry, updated countertops, a new kitchen sink, decorative backsplash, and an abundance of workspace. A huge under-stair storage area provides valuable extra storage rarely found in similar homes. Upstairs, all three bedrooms are thoughtfully positioned for privacy. The spacious primary suite features crown molding, an en-suite bath and ample closet space, while two additional bedrooms offer flexibility for family, guests, or a home office. Additional upgrades and features include a recently replaced A/C system (2021), washer and dryer (2024).Residents of Tucker Oaks enjoy access to a community pool and low-maintenance living in a peaceful setting. Ideally located just 1.4 miles from Historic Downtown Winter Garden and the popular Plant Street Market, you'll enjoy easy access to boutique shopping, dining, entertainment, farmers markets, and year-round community events. Outdoor enthusiasts will appreciate the nearby West Orange Trail, Oakland Nature Preserve, and Oakland Arts & Heritage Center. Commuters will love the quick access to Florida's Turnpike and major highways, while the new Costco in Clermont adds even more convenience.Move-in ready and meticulously cared for, this exceptional home offers the perfect combination of comfort, convenience, and location. Schedule your private showing today!
Listing is courtesy of: COLEDEV REAL ESTATE LLC (407-915-0456)
Listing Agent: Aileen Frauman (407-928-0211)
107 TRADITIONS DR, WINTER GARDEN, FL 34787
$429,975134 Days on yellowkey MLS ID: S5145650
0 Days Off yellowkey (back on 7/6/2026)
REDUCED by $15,000 (3.4%) on 07/02/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1582 Built: 1999Monthly Fee: $45 Tax: $1,458 (2024)Community: Traditions SubSingle Family
Taxes:$1,458
Tax Year: 2024
Remarks: Under contract-accepting backup offers. New Price! Location!!! The family will love this beautiful, Former Model home in Traditions! Blocks away from Downtown Winter Garden! Golf carts welcome! This 3/2 split plan has wood laminate flooring in living room & the master bedroom. Kitchen is open, Ceramic tile & eat-in space overlooking backyard. Master Bedroom is spacious with Walk-in shower and separate tub. Private / separate laundry room. Separate office or workshop in garage is UNDER AIR UNDER & perfect for the handyman! The backyard is fully fenced. Enjoy the restaurants, famer's market & shops all in walking distance or use a golf cart! Separate Workshop room. AC 2019. Easy access to the turnpike, 429, 408 to downtown Orlando or OIA! Great Schools!
Listing is courtesy of: WATSON REALTY CORP (407-298-8800)
Listing Agent: Rick Evans, Ii (407-538-9295)
1349 CASTLEPORT RD, WINTER GARDEN, FL 34787
$720,000148 Days on yellowkey MLS ID: O6377923
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3673 Built: 2001Monthly Fee: $250 Tax: $9,122 (2024)Community: Stoneybrook West 44/134Single Family
Taxes:$9,122
Remarks: This beautiful renovated 5-bedroom home located in the guard-gated golf community of Stoneybrook West, in Winter Garden, offers two primary suites, three additional bedrooms, and a large loft/flex space, ideal for multi-generational living or a home office. New stair and loft railings have been installed to enhance safety and functionality. The open-concept floor plan features abundant natural light and a seamless layout for entertaining. Enjoy a spacious fenced backyard with room for a pool or outdoor living area. Stoneybrook West offers a boat ramp, fishing areas, and lake access for water enthusiasts, a clubhouse, fitness center, and a large resort-style community pool. Residents can enjoy tennis courts, a golf course, basketball court, a playground, and feel at ease with a 24-hour guard-gated entrance ensuring a secure and peaceful living environment with scenic walking and biking trails. Conveniently located near shopping, dining, top-rated schools, and major roadways with easy access to Orlando and area attractions. Resort-style living in a prime Winter Garden location.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
638 AUTUMN OAKS LOOP, WINTER GARDEN, FL 34787
$594,00048 Days on yellowkey MLS ID: G5113531
2 Days Off yellowkey (back on 7/4/2026)
REDUCED by $26,000 (4.2%) on 06/18/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2044 Built: 2005Monthly Fee: $146 Tax: $3,096 (2025)Community: Winter OaksSpa: NoSingle Family
Taxes:$3,096
Remarks: Under contract-accepting backup offers. Experience the quintessential Winter Garden lifestyle in this exceptional 3 bedroom/2.5 bathroom home, perfectly positioned within the highly sought-after Golf Cart District. This residence offers a rare park-side setting, providing picturesque views of majestic oaks with green space. For those who enjoy active community life, you are just steps away from the neighborhood pool and playground. Just a few minutes away from Downtown Winter Garden! Exceptional Curb Appeal & Interior Elegance: from the moment you arrive, the covered front porch welcomes you with outdoor column lights, coach lights, landscaping and a framed transom over the front door. The first-floor features stylish Bahama shutters, formal living room with a double paddle ceiling fan, spacious dining area, a family room that features a gas fireplace, with tile flooring, engineered wood floors and LVP throughout the first floor. Chef-Inspired Kitchen : The heart of the home is the kitchen, which has been upgraded from an electric to a gas stove and features a redesigned pantry to maximize storage. You will also find under-cabinet lighting and modern lighting. Primary suite: The 1st floor Primary Bedroom suite serves as a private sanctuary with new flooring throughout the bedroom, closet, and bathroom, as well as a completely remodeled primary bathroom. The second story split floor plan: The transition to the second floor is highlighted by a staircase and balcony where traditional wood newels have been replaced with elegant rod iron. The second story features 2 spacious bedrooms , a full sized guest bathroom and at center stage of the upstairs landing is a bonus area for additional lounging area/home office or play area. Outdoor Oasis: Step outside to your private retreat: a rear enclosed screened-in room that perfectly encompasses the lanai and soaker pool area. The outdoor space is further enhanced by: An extended patio deck around the pool, a new fan on the lanai for year-round comfort, a rebuilt pool pump with pool equipment housing, a new fence with a leveled concrete retaining wall base, accented by fence and landscape lighting. Systems & StorageSolutions: This home offers incredible peace of mind with a new roof (installed 11/2020) and a brand-new AC condenser and coils ) with a transferable warranty. Storage is a priority here, with a garage featuring built-in file cabinets, recessed ceiling lights, shelves, appliance storage, and overhead shelving, plus additional attic storage. Functional extras include a built-in wall safe, a generator pad, and a security camera at the rear of the home. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ELITE PARTNERS III REALTY (321-527-5111)
Listing Agent: Lorie Gullian (407-928-8078)
2230 ROMANUM DR, WINTER GARDEN, FL 34787
$565,000139 Days on yellowkey MLS ID: O6389947
1 Days Off yellowkey (back on 5/17/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2562 Built: 2014Monthly Fee: $207 Tax: $8,425 (2025)Community: Alexander RdgSingle Family
Taxes:$8,425
Elementary School: Hamlin Elementary
Remarks: Motivated seller – bring your offers! Location, Location, Location! Don't miss the opportunity to own this beautiful and cozy 4-bedroom, 4-bath home featuring thoughtfully designed living spaces that combine comfort, functionality, and inviting charm. The main floor features all four bedrooms, offering convenience and privacy for everyday living. Upstairs, you’ll find a spacious bonus room with a full bathroom, perfect for a media room, game room, home office, or additional living space. This is the only area of the home with carpet, creating a comfortable and cozy environment for relaxation or entertainment. Throughout the main living areas, the home features luxury vinyl flooring, providing durability and a modern look while enhancing the overall warmth of the home. The kitchen opens beautifully to the main living area, creating a welcoming space for gathering with family and friends. The kitchen cabinets were recently refinished and painted, giving the kitchen a refreshed and updated appearance. Step outside and enjoy the screen-enclosed patio, offering a comfortable outdoor space where you can relax and enjoy Florida living with added protection from insects. The home also features attractive landscaping and brick pavers on the driveway and entrance, creating great curb appeal and a welcoming first impression. Additionally, the property includes solar panels, contributing to improved energy efficiency. This home offers a warm and inviting atmosphere with well-distributed spaces that make it perfect for both everyday living and entertaining. Schedule your private showing today and come experience the comfort and charm this home has to offer in a perfect location!
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Marcelle Da Silva Sampaio (407-369-3621)
2022 BOSS HEWETT ST, WINTER GARDEN, FL 34787
$679,00041 Days on yellowkey MLS ID: O6417697
1 Days Off yellowkey (back on 7/2/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2281 Built: 2022Monthly Fee: $171 Tax: $7,948 (2025)Community: Hull Island/Oakland Ph 2Single Family
Taxes:$7,948
Remarks: Under contract-accepting backup offers. This turnkey, better-than-new single-story home offers an elegant and modern retreat within Oakland’s highly desirable waterfront community of Hull Island. Nestled in a friendly neighborhood surrounded by nature, the property immediately welcomes you with tasteful customizations, upgraded lighting, and stylish accent walls that bring warmth and character to the entire layout. The thoughtfully crafted split floor plan features four bedrooms and three bathrooms, maximizing both privacy and efficiency for daily living and entertaining. Right off the foyer, a comfortable guest bedroom boasts its own ensuite bath, creating an ideal setup for visitors or multi-generational families. The main living area flows seamlessly into a beautifully upgraded kitchen equipped with quartz countertops, under-cabinet lighting, a tile backsplash, and premium stainless steel appliances including a cooktop with a hood and a built-in oven and microwave. Tucked quietly away at the back of the home, the primary suite serves as a private oasis with an expansive spa-like bathroom featuring separate vanities, sleek quartz counters, a large shower, and dual walk-in closets with custom storage systems. The remaining bedrooms are equally impressive, offering ample space, custom closets, and electronic shades. The sophisticated interior transitions smoothly to a private backyard retreat where a covered lanai, extensive pavers, and a full screen enclosure set the perfect stage for relaxed Florida outdoor living. Practical needs are also effortlessly met in the two-car garage, which showcases durable epoxy flooring and a modern electric vehicle charger. Beyond the property lines, the Hull Island community provides an exceptional lifestyle centered around outdoor recreation and convenience. Residents enjoy access to a resort-style pool, a playground, a dog park, and a scenic boardwalk that winds its way to a community dock and fishing pier on Lake Apopka. Nature lovers will appreciate the neighborhood's private entrance to the 120-acre Oakland Nature Preserve, as well as close proximity to the famous 22-mile West Orange Trail, local golf courses, and pickleball courts. Complete with fast access to the Turnpike, 408, and 429, this location connects you quickly to excellent shopping, dining, and the charming downtown districts of Winter Garden, Clermont, and Oakland, while keeping Orlando’s theme parks and international airport within easy reach.
Listing is courtesy of: BALDWIN PARK REALTY LLC (407-986-9800)
Listing Agent: Brian Cirillo (321-231-1068)
WINTER GARDEN, FL 34787
$217,50028 Days on yellowkey MLS ID: O6420656
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 942 Built: 2005Monthly Fee: $378 Tax: $2,727 (2025)Community: Southern Pines CondoSpa: NoCondo
Taxes:$2,727
Remarks: Beautiful 1BR/1BA condo with a bright open floor plan, spacious solarium/flex space, granite countertops, walk-in closet, and interior laundry. Located in the gated Southern Pines community featuring a resort-style pool, fitness center, indoor basketball and racquetball courts, tennis courts, playground, and clubhouse. Conveniently located near Downtown Winter Garden, Winter Garden Village, major highways, shopping, dining, and entertainment. Northeast-facing unit with abundant natural light and excellent community amenities.
Listing is courtesy of: IRM INVEST., REAL EST.& MGMT. (407-903-0134)
Listing Agent: Gonzalo Senior (407-353-8841)
2496 BARONSMEDE CT, WINTER GARDEN, FL 34787
$875,00033 Days on yellowkey MLS ID: G5114233
0 Days Off yellowkey (back on 7/2/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4184 Built: 2002Monthly Fee: $210 Tax: $8,903 (2025)Community: Stoneybrook West 47/78Spa: YesSingle Family
Taxes:$8,903
Remarks: Under contract-accepting backup offers. Welcome home to 2496 Baronsmeade Ct Winter Garden situated in the much sought after golfing community of Stoneybrook West !!! This 4 Bedroom, 41/2 Bath pool home backing onto the golf course offers over 4,000sqft of living space with so many upgrades and 3 car garage with paved driveway. The tile ROOF was replaced in 2022, the AC's were replaced in 2021, kitchen and bathrooms fully renovated, new flooring throughout, all windows have custom vinyl shutters to keep the Florida heat out and save on utility bills. As you enter the home we have a formal living and dining area with built in wine bar, a huge open space with double story entry. The kitchen was fully remodled with a large center Island with Quartz countertops with waterfall edge. Lots of cabinet space and a walk in pantry, bar seating and breakfast nook. The kitchen over looks the great room wih vaulted ceilings and a gas fireplace as the focal part of the room. New sliding glass doors lead out to the huge screaned lanai with a salt water pool and spa and a built in BBQ that comes with the sale of the home. Plenty of space to enjoy the Florida lifestyle with a full sized bathroom. The Primary bedroom is downstairs and offers a large bedroom with bonus living space/home office/work out area, walk in closet and a renovated bathroom with dual vanities, large walk in shower and separate tub. Upstairs we have a enourmous loft space with built in desk space, ideal for home office/pool table/media/living space. There are 3 additional oversized bedrooms and 2 additional bathrooms to complete the upstairs. The laundry room is situated downstairs just off the garage. Stoneybrook West has so much to offer with a golf course, Restaurant, Fitness Center, Olympic Sized Swimming Pool, Playground, tennis courts, pickle ball, bastket ball and so much more. The low HOA fee covers Cable/Internet/Guarded gated community and access to all the amenities. Ideally located next to major HWYs, Disney, short commute to Orlando, Restaurants and shopping. This home has so much to offer with all the major upgrades already completed. Call today for your own private tour !!!
Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)
Listing Agent: Sarah Gholami (352-346-7857)
14790 TULLAMORE LOOP, WINTER GARDEN, FL 34787
$675,000119 Days on yellowkey MLS ID: O6395287
REDUCED by $14,999 (2.2%) on 06/13/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3410 Built: 2005Monthly Fee: $100 Tax: $3,503 (2025)Community: Emerald RidgeSingle Family
Taxes:$3,503
Elementary School: Lake Whitney Elem
Remarks: Expansive and Inviting! Welcome home to 14790 Tullamore Loop. Location says it all! Convenient to restaurants, shopping, highways, theme parks, and more, this gated community remains one of the most popular communities in the area. This family-oriented neighborhood with a community pool is sure to please. With an oversized lot and plenty of room to roam, the open floor plan of this 4-bedroom / 2.5-bath home awaits to impress. Large formal living and formal dining rooms are the perfect venue for family gatherings. An elegant, open kitchen, overlooking the dinette into the family room, offers granite counters, 42” cabinets, double built-in ovens, a large breakfast bar, and a huge walk-in pantry allowing space for everyone to help the cook. When the day is done, retire to the oversized second-floor primary suite, which offers a spacious bath with a double-sink vanity, shower, garden tub, and a walk-in closet, completing this special and intimate space. Anchoring 3 large secondary bedrooms, this home beckons to an active family, offering the space you need. Enjoy your morning coffee or an evening barbecue, while enjoying the peace of your private pool, a HUGE private backyard! Complete with fruit trees (recovering from the freeze), including mango, sugar apple, sapodilla, guava, loquat, pear, jackfruit, fig, lemon, orange, neem, and banana, gives an instant farm-to-table experience. While certainly offering plenty of space for everyone to claim their own piece of paradise, you’ll find peace of mind that your investment is in a location that can’t be beat! Highlights include: Roof replaced in 2020. AC replaced in 2018. Appliances replaced in 2022. All blinds replaced 2022. Whole Home water filtration and softener system. Be sure to click the link for an interactive 3D Virtual Tour and floor plan!
Listing is courtesy of: FLORIDA REALTY INVESTMENTS (407-207-2220)
Listing Agent: Rita Phillips (407-928-0573)
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