Homes for Sale Near West Orange High in Winter Garden - 174 homes

Remarks: Under contract-accepting backup offers. Welcome to this exceptional 4-bedroom, 4-bath residence with a private office, expansive loft, and 2,831 square feet of beautifully designed living space in the highly sought-after McKinnon Square at Oakland Park, nestled within Winter Garden's coveted golf cart district. Perfectly positioned on a private corner end lot, this stunning home is complemented by a welcoming front porch and showcases timeless architecture, upscale designer finishes, and exceptional attention to detail. Step inside to discover soaring ceilings, abundant natural light, and beautiful white oak luxury vinyl plank flooring throughout the main living areas. A private office just off the foyer provides the ideal work-from-home space or flex room, while custom window treatments, plantation shutters, designer wallpaper, elegant accent walls, and custom built-ins create a warm yet sophisticated atmosphere. At the heart of the home, the gourmet chef's kitchen features custom cabinetry with upgraded hardware, quartz countertops, an oversized island with designer pendant lighting, a gas cooktop, custom vent hood, built-in wall oven, decorative tile backsplash, and abundant storage. The open-concept design flows effortlessly into the spacious family room, where custom built-ins create the perfect gathering space for entertaining or relaxing. The thoughtfully designed floor plan includes a private first-floor guest suite with a full bath, ideal for guests or multigenerational living. Upstairs, an expansive loft offers flexible living space perfect for a media room, game room, or second family room. The luxurious primary suite is privately situated away from the secondary bedrooms and offers tray ceilings, designer accent walls, a spacious walk-in closet, and a spa-inspired en-suite bath featuring dual quartz vanities, a soaking garden tub, and a separate walk-in shower. Two additional upstairs bedrooms each feature walk-in closets, with one offering its own private en-suite bath, while another full bath serves the remaining bedroom and loft. Even the laundry room has been elevated with designer wallpaper, quartz folding countertops, and an included washer and dryer. Outside, the private corner homesite enhances both curb appeal and privacy, offering additional green space and a peaceful setting to enjoy the Florida lifestyle. Living in Oakland Park means embracing one of Winter Garden's most desirable lifestyles. This award-winning, master-planned community of Oakland Park features tree-lined streets, scenic parks, resort-style pools, playgrounds, and miles of walking and biking trails, including direct access to the renowned West Orange Trail. Residents enjoy a true neighborhood atmosphere just a golf cart ride from Historic Downtown Winter Garden, where you'll find award-winning restaurants, boutique shopping, breweries, coffee shops, live entertainment, and the nationally recognized Winter Garden Farmers Market. With convenient access to Florida's Turnpike, SR-429, downtown Orlando, and Central Florida's world-famous attractions, this exceptional residence offers the perfect blend of luxury, convenience, community, and lifestyle.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Erica Sadelfeld (407-427-0398)

Remarks: Welcome to this beautifully maintained 5-bedroom, 3-bathroom single-story home in the highly sought-after gated community of Belle Meade — zoned for Whispering Oak Elementary (10/10 GreatSchools rating, top 5% of all schools in Florida), SunRidge Middle, and West Orange High School. With 2,918 square feet of thoughtfully designed living space, a 3-car garage, and a fenced corner lot spanning 0.27 acres, this home offers the space, privacy, and top-tier school access today's families are searching for. Major systems have already been taken care of for you — enjoy true peace of mind with a brand new roof (February 2024), backed by a CertainTeed SureStart warranty that's fully transferable to the new owner, and a brand new Trane 5-ton AC system (2025) with a 10-year warranty through 2035. No surprise repairs, no looming replacements — just move in and relax. Inside, soaring cathedral and vaulted ceilings, tray ceilings, crown molding, and wood flooring create an elegant, open feel throughout. A separate laundry room adds everyday convenience, and the fifth bedroom functions as a versatile den/utility space — ideal for a home office, playroom, or guest suite. The primary suite is a true retreat, featuring dual walk-in closets, dual vanities, a spa-style soaking tub, a separate standing shower, and a private water closet. Step outside to your fully screened and covered patio — perfect for entertaining or simply enjoying Florida's year-round sunshine, rain or shine — overlooking the private, fenced backyard. Belle Meade is a secure, gated community known for its lush landscaping, sidewalks, welcoming neighbors, and an on-site dog park. You're just minutes from Winter Garden Village at Fowler Groves — Central Florida's premier outdoor shopping and dining destination — and a short drive from historic Downtown Winter Garden's Plant Street, home to the award-winning Saturday Farmers Market, Crooked Can Brewing Company, and some of the area's best restaurants. Lake Apopka and several highly rated golf courses, including West Orange Country Club and Orange County National Golf Center (home to PGA Tour and LIV Golf events), are also just minutes away. Commuters and theme park lovers alike will appreciate the unbeatable location: Walt Disney World is approximately 15–25 minutes away via SR 429, with Universal Studios and SeaWorld each roughly 20–30 minutes via the Florida Turnpike. Downtown Orlando is approximately 20–25 minutes away via SR 408 or SR 50, and Orlando International Airport is about 30–35 minutes via the Turnpike. This is a rare opportunity to own a move-in ready home with major systems already updated, zoned for one of Florida's top-rated elementary schools, in one of Winter Garden's most desirable gated communities. Schedule your private showing today!

Listing is courtesy of: THE FLORIDA PROPERTY SHOP SALE (352-346-7857)

Listing Agent: Nikhil Vashist (352-901-3786)

Remarks: Located in the highly desirable Stoneybrook West community, this beautifully maintained 4-bedroom, 2-bath home offers the perfect blend on comfort, style, and convenience. Featuring a newer roof installed in 2019, brand-new 2025 central air conditioning system, newer refrigerator, new range/oven, and new dishwasher. The home welcomes you with abundant natural light, an open concept layout, and spacious living areas enhanced by attractive laminate flooring throughout. One of the home's standout features is the serene pond view from the screened lanai. With four bedrooms and versatile living spaces, this home easily accommodates families of all sizes.

Listing is courtesy of: SUSANA JORDAN STUTSMAN (321-278-0334)

Listing Agent: Susana Stutsman (321-278-0334)

Remarks: Welcome to this exceptional pool home in the highly sought-after gated community of Hickory Hammock in Winter Garden. Offering more than 3,600 square feet beautifully designed living space, this impressive five bedroom, four bathroom, 4 car garage residence blends timeless elegance with everyday functionality. From the moment you step inside, you'll be captivated by soaring ceilings, georgous formal dining space, elegant coffered and wainscoting details, custom built-ins, and an abundance of natural light. The open concept floor plan creates an effortless flow, making the home ideal for both intimate gatherings and grand entertaining. At the heart of the home, the gourmet kitchen overlooks the expansive living and dining areas, it features quartz counter tops, abundant cabinetry, generous prep space, and a layout designed for both entertaining and everyday living. A downstairs private home office offers a refined work from home setting, while the expansive upstairs loft is an entertainer's dream, complete with a projector and oversized movie screen, creating the perfect setting for cinematic experiences, game days, or a stylish media lounge. The luxurious primary suite serves as a peaceful retreat with a spacious walk-in closet and spa-inspired ensuite bath. Thoughtfully designed secondary bedrooms and bathrooms provide comfort and privacy for family and guests. Step outside to your own private outdoor oasis where a screened resort-style pool and covered lanai create the ultimate setting for year-round Florida living. Whether hosting guests or enjoying a quiet evening at home, this backyard is designed for relaxation and entertaining. Recent enhancements that showcase true pride of ownership, including a freshly repainted interior, whole home pressure washing, new landscape, and a professionally serviced and cleaned air conditioning system. Residents of the gated community of Hickory Hammock enjoy an exceptional lifestyle with resort-style amenities including a clubhouse, fitness center, community pool, playgrounds, dog park, scenic walking trails, fishing pier, and boat ramp access to the beauty of Johns Lake. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, top rated schools, shopping, dining, SR 429, Walt Disney World, and Orlando's world class attractions, this remarkable home offers the perfect balance of luxury, lifestyle, and convenience. Schedule your showing today!

Listing is courtesy of: HOGAN REALTY GROUP INC (321-474-2004)

Listing Agent: Kaitlin Sidders (407-797-2985)

Remarks: Along a charming brick street in one of the desirable areas of southwest Orange County, this beautifully updated 1938 cottage-style home offers a blend of historic character and modern convenience in the heart of downtown Winter Garden. On an oversized, fully fenced corner lot within the sought-after golf cart district, this rare gem is just blocks from historic Plant Street, the famed Plant Street Market, weekend farmers market, premier dining, shopping, entertainment and scenic West Orange Trail. This inviting three-bedroom, two-bath home features 1,273 square feet of thoughtfully updated living space with stylish laminate and ceramic tile flooring throughout, blending timeless charm with modern finishes. Inside, you'll find a functional layout with inside laundry, a warm and welcoming atmosphere, and a newer air-conditioning system for added peace of mind. Enjoy quiet mornings or relaxing evenings from the desired front and rear porches overlooking the fully fenced yard, ideal for entertaining, pets or simply enjoying the Florida lifestyle. The oversized double carport and extended driveway provide abundant parking, while the exterior storage room within the carport offers exceptional flexibility for hobbies, tools, golf cart accessories or additional storage needs. Homes with this level of charm, character and accessibility rarely become available in downtown Winter Garden. Combining an unbeatable location, oversized corner lot and the convenience of golf cart living just near everything Plant Street has to offer, this is a special opportunity to own a piece of one of Central Florida's beloved historic communities.

Listing is courtesy of: PREMIER SOTHEBYS INT'L REALTY (407-480-5014)

Listing Agent: Michael Mitchell, Jr (352-768-1712)

Remarks: Location! Location! Welcome to this wel maintained 3 beds 2 bath single family home located in the desirable community of Stone Creek in Winter Garden. This home offers a spacious living room, dining area, spacious master bedroom with double sink and walking closet, 2 extra bedrooms and sharing bath, 2 car garage, screened porch and generous fenced back yard. This property is convenient located near shops, restaurants, and the highly rated Elementary School is located inside the community with walking distance. Also, near Winter Garden village Mall, Stonybrook West Golf Club, Tucker Ranch Wellness Park (in construction) And easy acces to the Highway and Airport.

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Maria Howard (410-422-3518)

Remarks: Finding nearly 4,000 sqft of beautifully UPDATED living space on an oversized CORNER LOT is increasingly rare. Add a full-width BALCONY overlooking the GOLF course, extensive RENOVATIONS throughout, and a backyard that extends well beyond the existing fence line, and this home immediately stands out. From the moment you step inside, you'll notice how effortlessly this unfurnished home flows. Whether you're looking for multiple living areas, a dedicated home office, fitness space, media room, or simply room to spread out, this flexible layout adapts to the way you live. At the heart of the home is the beautifully REMODELED KITCHEN, redesigned in 2022 with quartz countertops, an oversized island, abundant cabinetry, and a Samsung Bespoke appliance suite installed in 2024. It creates a natural gathering space before flowing seamlessly into the family room, where the fireplace provides a warm focal point for everyday living and entertaining. Luxury vinyl plank flooring runs throughout the home, while EVERY BATHROOM has been tastefully RENOVATED and FRESH interior PAINT gives the home a bright, contemporary, move-in-ready feel. Upstairs, the expansive LOFT has already been transformed into an impressive HOME CINEMA, complete with in-ceiling surround sound, dedicated audio equipment, a high-performance subwoofer, and discreet in-wall cable management. It also offers exceptional flexibility as an additional living area, games room, or creative workspace. One of the home's most distinctive features is the impressive full-width balcony spanning the rear of the property. Accessible from both the primary suite and the adjoining bedroom or office, it's the kind of OUTDOOR SPACE you'll genuinely use, whether that's enjoying your morning coffee overlooking the golf course, catching the evening breeze, or simply taking a quiet moment at the end of the day. Outside, the sense of space continues. The backyard feels like an extension of the home's living space, with a PRIVATE PUTTING GREEN, artificial turf, upgraded deck, patio lighting, and refreshed landscaping creating an inviting setting for relaxing or entertaining outdoors. The FENCED YARD provides a wonderful private outdoor space, but what many buyers won't immediately realise is that the property extends significantly beyond the current fence line, giving you even more usable land than first meets the eye. Combined with the generous side yard afforded by this oversized corner homesite, the amount of outdoor space is truly impressive. Equally valuable are the updates you may not immediately notice. Major improvements include a NEW ROOF (2022), high-efficiency HVAC system (2022), whole-home SOLAR system (2022), whole-home WATER SOFTENER and filtration system (2025), automatic irrigation system with timer, Alexa-compatible smart home features and an electric vehicle charging station. Set within the GUARD-GATED community of Stoneybrook West, residents enjoy championship golf, a WATERFRONT CLUBHOUSE overlooking Lake, resort-style pool, FITNESS center, TENNIS and BASKETBALL courts, playgrounds, PRIVATE BOAT RAMP with lake access, community boat storage, and 24-hour guarded security. Conveniently positioned near one of the community entrances, the home offers quick access to Winter Garden Village, shopping, dining, schools, and major roadways, combining exceptional convenience with one of Winter Garden's most sought-after lifestyles.

Listing is courtesy of: SERHANT (786-296-8626)

Listing Agent: Zoe Attwood (407-516-9009)

Remarks: Virtually Staged. Built by the owner with uncompromising construction standards, this Winter Garden masterpiece delivers the kind of quality and engineering you simply don’t find in today’s market. And with the seller just reducing the price, this luxury home is now an even more exceptional opportunity. Concrete structural design, hurricane-rated engineering, impact windows, full foam insulation, fiber-cement siding, and an Ipe hardwood porch set the tone for durability and refinement. Inside, natural light pours across level-5 walls, rich wood flooring, crown molding, and custom shutters—creating a warm, polished, magazine-worthy aesthetic. The open living and chef’s kitchen are built for elevated living: gas range, pot filler, handcrafted cabinetry, and a dramatic retractable pocket door that dissolves the boundary between indoors and out. The resort-style back porch is a showpiece—pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, and a half bath—perfect for hosting unforgettable evenings. The primary suite is pure indulgence, featuring a spa-inspired bath with dual shower heads, soaking tub, digital controls, a custom closet, and a private concrete safe room. A butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring elevate everyday convenience. Upstairs, the bonus/game room and oversized balcony create a luxe hangout zone. Storage is abundant with walk-in closets throughout. And the finished two-story garage loft—pre-plumbed and air-conditioned—offers endless possibilities: in-law suite, golf simulator lounge, gym, office, or creative studio. Outside, curated landscaping, gas lanterns, an architectural driveway, and a heated concrete hot tub with Wi-Fi controls complete the experience. All just moments from Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre. A rare blend of craftsmanship, luxury, and location—now at an even more compelling price.

Listing is courtesy of: HOMEVEST REALTY (407-897-5400)

Listing Agent: Lora King (407-947-7653)

Remarks: Under contract-accepting backup offers. Welcome to 1209 Castleport Rd — your next chapter in Stoneybrooke West, a gorgeous golf-course community where everyday feels like a getaway. From the moment you arrive you’ll love the manicured fairways, peaceful walking paths, and neighborhood pride that make this community stand out. Step inside and imagine family mornings and movie nights in the bright, open living spaces. This home offers 5 spacious bedrooms and 3 full bathrooms — plenty of room for guests, a home office, or a hobby room. Thoughtful finishes and flexible room spaces make entertaining effortless and daily life comfortable. Location is everything: you’re minutes from theme parks, with fast highway connections for stress-free commutes and weekend escapes, plus easy access to shopping, dining, and services. Whether you’re teeing off on the greens, grabbing dinner nearby, or heading out for a day at the parks, 1209 Castleport Rd combines comfort, convenience, and that warm, community feel you’ve been looking for.

Listing is courtesy of: THE PROPERTY STOP LLC (407-744-5557)

Listing Agent: Angela Magac (407-744-5557)

Remarks: Welcome to luxury lakefront living in the gated community of Hickory Hammock at Johns Lake. Situated on an oversized homesite overlooking beautiful Lake Burnett, this exceptional 5-bedroom, 4-bathroom home with a 3-car garage and resort-style pool offers the perfect blend of elegance, comfort, and modern updates. From the moment you step inside, you'll be captivated by the rich hardwood floors that flow throughout the entire home, exquisite crown molding, and thoughtfully designed spaces. The versatile formal living room features a stunning accent wall, while the formal dining room and beautifully detailed staircase with decorative tile risers create an inviting atmosphere for entertaining. A first-floor bedroom and full bath offers exceptional flexibility for a variety of living arrangements while enjoying serene lake views. The fully updated gourmet kitchen is a chef's dream, featuring a large center island, double wall ovens, cooktop, pantry, new refrigerator, dishwasher, upgraded quiet garbage disposal, and seamless views into the spacious family room with custom solid wood built-in cabinetry. Through the expansive 8-foot glass slider, you'll discover your private outdoor oasis complete with a sparkling pool and spa, sunken gas fire pit, Covered Patio with remote screens and breathtaking lake views, and a gas stub already in place for a future outdoor kitchen or grill. The Second floor offers a generous loft provides additional living space, while the luxurious primary suite offers a private sitting area, a massive custom walk-in closet by The Container Store, and a recently renovated spa-inspired bath featuring dual vanities, adjustable lighted mirrors, marble accents, herringbone flooring, an oversized soaking tub, and a spacious walk-in shower. The upstairs laundry room is beautifully appointed with custom cabinetry, a solid wood folding counter, hanging bar, and designer tile accent wall. Bedroom three includes its own en-suite bath and walk-in closet, and the spacious second floor entertainment room showcases a Chicago brick accent wall and custom sliding barn door. Bedrooms four and five are equally inviting with designer finishes and custom closet systems. Surrounded by natural beauty and abundant wildlife, Hickory Hammock has it all. With a community resort pool with zero entry, clubhouse, fitness center, tennis courts, volleyball courts, playground & miles of walking paths around this lake community! This extraordinary property offers the tranquility of lakefront living while being conveniently located near major roadways, shopping, dining, and top-rated schools. This is more than a home—it's a lifestyle.

Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)

Listing Agent: Steve Glose (407-616-7286)

Remarks: Exceptional Downtown Winter Garden Investment Opportunity! Located in one of the most desirable areas of Downtown Winter Garden, this property presents an outstanding opportunity to build your dream home or complete a substantial renovation in an area where redevelopment continues to thrive. The existing 1924 home is approximately 912 square feet with 2 bedrooms and 1 bathroom and is being sold AS-IS, with the value primarily in the location and land. Public records indicate a 5,024-square-foot lot zoned R. Enjoy the unmatched lifestyle that Downtown Winter Garden is known for, with convenient access to Plant Street's award-winning restaurants, boutique shopping, the weekly Farmers Market, Crooked Can Brewing Company, live entertainment, and the West Orange Trail. Whether you're a builder, investor, or buyer looking to create a custom home in one of Central Florida's most sought-after downtown districts, this is a rare opportunity to secure a property with tremendous potential in a location where new construction and beautifully renovated homes continue to command premium values. Don't miss your chance to invest in the future of Downtown Winter Garden!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Corey Cannon (407-615-0215)

Remarks: Beautiful maintained 3 bedroom 2.5 bath townhome located in the highly desirable DANIELS LANDING community in WINTER GARDEN. This property features recent mayor updates including brand new carpet. Rooms on second floor. It has a screened porch to enjoy the afternoons with family and friends. Spacious layout, ideal location and low maintenance living make this property a standout. Top rated schools. Community amenities included gated access, pool, a clubhouse, fitness center and a playground. Conveniently located near Winter Garden Villages that offers shopping and gathering opportunities for everyone needs! Close to Mayor highways Turnpike, 429 and I-4. Minutes from Disney World and many other attractions! Great as a primary home or investment opportunity. A must see today!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Julieta Kraponick (407-432-5102)

Remarks: Welcome to this beautifully designed 5-bedroom, 4-bath home located in a gated Winter Garden community, offering an exceptional blend of elegant finishes, functional living spaces, and resort-style outdoor living. With soaring ceilings and an inviting open entry, this home is filled with architectural details including crown molding, coffered and tray ceilings that add character throughout. Designed for both everyday living and entertaining, the thoughtfully crafted floor plan offers formal living and dining areas while maintaining an open flow between the kitchen and family room. Tile flooring extends through the main living areas and luxury vinyl in the primary suite and entire upstairs, providing both style and durability. The spacious kitchen serves as the heart of the home with granite countertops, abundant cabinetry, generous counter space, bar seating, a separate dinette, and seamless views into the family room. Expansive pocket sliding glass doors create a true indoor-outdoor living experience, opening the family room to the covered lanai and pool area—perfect for entertaining family and friends. The first-floor primary suite is a private retreat featuring abundant natural light, direct access to the lanai, dual walk-in closets, separate vanities, a walk-in shower, and a relaxing soaking tub. A dedicated office with built-in shelving and closet space provides an ideal work-from-home setup. Two additional bedrooms and bathrooms are also located downstairs, including a private en-suite with direct access to the pool. Upstairs offers exceptional flexibility with a spacious loft that can serve as a second living area, game room, or playroom, along with a fourth bedroom and full bath. A fifth bedroom is currently configured as a media room with surround sound and projector hookups, making it ready for movie nights or easily converted back to a bedroom. Step outside to your own backyard retreat featuring a sparkling pool with a natural rock waterfall, a unique swim-up table, and a spacious covered lanai. The fully fenced backyard provides both privacy and room to relax, play, or entertain. Additional highlights include a three-car garage and an ideal location just minutes from Winter Garden Village, offering shopping, grocery stores, restaurants, and healthcare. With convenient access to SR-429 and Historic Downtown Winter Garden, this home combines the comfort of a gated community with easy access to everything Central Florida has to offer.

Listing is courtesy of: REVEL REALTY LLC (407-876-6448)

Listing Agent: Chris Sapp (407-574-1002)

Remarks: Located in the highly desirable gated community of Glynwood in Winter Garden, this spacious 5-bedroom, 4-bath pool home offers over 3,500 square feet of living space on a private cul-de-sac lot. The versatile floor plan features a first-floor owner's suite, dedicated office/den, formal and casual living areas, and an upstairs bonus/media room with an additional bedroom and bath—ideal for guests, multi-generational living, or a home theater. The screened pool and spa create a private backyard retreat, while the 3-car garage (AC by Modern Wall Unit and Upgraded Garage Floor Coating) provides ample storage and parking. Residents enjoy access to community amenities including a pool, tennis courts, playground, and gated entry. Conveniently located near Winter Garden Village, historic downtown Winter Garden, major highways, shopping, dining, and area attractions.

Listing is courtesy of: CHOICEPOINTE REALTY, INC. (888-246-5758)

Listing Agent: Mary Dees (407-468-8285)

Remarks: Welcome to this exceptional ONE-OWNER CUSTOM HOME, sitting on a ONE-ACRE HOMESITE in one of Oakland’s most sought-after locations. Offering 3,515 square feet of living space (4,890 total square feet), this thoughtfully designed 4-bedroom, 3.5-bath residence combines timeless Old Florida charm with OUTSTANDING QUALITY CONSTRUCTION, FEATURING ALL-STEEL CONSTRUCTION—INCLUDING STEEL ROOF TRUSSES—for exceptional durability and peace of mind. A circular driveway and side-entry OVERSIZED TWO-CAR GARAGE create impressive curb appeal, while double front doors welcome you into a spacious, OPEN FLOOR PLAN with 17.5' VAULTED CEILINGS in living area and 10' CEILING HEIGHT in bedrooms.This home has been designed for both everyday living and entertaining. At the heart of the home is a stunning DOUBLE-SIDED FIREPLACE with Tennessee Stone which creates a beautiful focal point between the formal living room and the inviting family room. The living areas flows seamlessly into the kitchen, separated only by a short wall between the kitchen and dining room that preserves the home’s open, airy feel. The EXPANSIVE KITCHEN is designed to bring everyone together, featuring TWO SINKS, a WRAPAROUND BREAKFAST BAR with seating for up to eight, a center ISLAND WITH COOKTOP, generous eat-in dining area, WALK-IN PANTRY with custom built-in shelving, and abundant countertop workspace. The open layout allows the kitchen, dining, and living areas to remain connected, making this home ideal for entertaining, holidays, and family gatherings. The desirable THREE-WAY SPLIT FLOOR PLAN offers both privacy and flexibility. Two secondary bedrooms and a full bath are located toward the front of the home, while a separate guest wing features an additional bedroom, full bath, oversized laundry room with storage, and a convenient half bath. Privately tucked away on the opposite side of the home, the spacious primary suite offers two walk-in closets and an ensuite bath with a walk-in shower. Double glass doors open to an expansive screened lanai that extends the living space outdoors, complete with a summer kitchen and peaceful views of the lush backyard. Additional updates include a tile roof (2015), HVAC ductwork (2020), exterior stucco upgrades and fresh paint (2021), one water heater replaced in 2018 and the second in February 2025, Connection to city water in 2019, The well was retained exclusively for lawn irrigation. Perfectly located with convenient access to the Florida Turnpike, Highway 50, shopping, dining, and area attractions. This meticulously maintained custom home offers the rare combination of quality construction, timeless design, generous living spaces, and an unbeatable Oakland location. This is Florida living at its finest.

Listing is courtesy of: CARIS REALTY AND INVESTMENTS INC (407-595-0009)

Listing Agent: Janelle Conway (407-595-0009)

Remarks: Priced to sell and ready to fall in love with. Welcome home to 17224 Old Country Lane. Tucked behind a private gate on over 2.3 sprawling acres, this completely renovated farmhouse-style retreat delivers the rare combination of space, privacy, and location that rarely comes together like this. With 6 bedrooms, 3.5 bathrooms, and 3,629 square feet of thoughtfully designed open-concept living all on one level this home was made for gathering, entertaining, and simply living well. Step outside to your own private oasis: a sparkling pool and spa framed by a screened-in patio, perfect for lazy Florida mornings and unforgettable evenings under the stars. A separate garage offers flexible storage for a boat or additional vehicles, while new septic systems, a private well, and a new electric fence add peace of mind to the property's undeniable charm. All of this just minutes from the shops, dining, and energy of Hamlin, and zoned for sought-after A-rated schools. Homes like this with this much land, this much privacy, and this much heart don't come around often. Schedule your private showing today before it's gone.

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Kerstin Crow (615-428-7046)

Remarks: Nestled in the highly coveted Courtlea Oaks community, within Winter Garden’s sought-after golf cart district, this beautifully updated home offers the perfect blend of timeless charm and modern luxury. Enjoy the lifestyle that has made historic downtown Winter Garden one of Central Florida’s most beloved destinations—just minutes away you’ll find award-winning restaurants, boutique shopping, the renowned Saturday Farmers Market, live entertainment, festivals, and miles of the West Orange Trail. Situated on an oversized .33-acre homesite, this exceptional residence offers 2,765 square feet with three bedrooms, two-and-a-half baths, and thoughtfully designed living spaces filled with architectural character. From the moment you enter, you’ll be welcomed by soaring ceilings, rich hardwood flooring, custom board-and-batten millwork, crown molding, and a stunning two-story foyer that creates an unforgettable first impression. At the heart of the home is a beautifully renovated kitchen featuring custom white cabinetry, a center island, farmhouse sink, professional-style gas range with pot filler, stainless steel appliances, and generous workspace—perfectly designed for both everyday living and effortless entertaining. The kitchen flows seamlessly into the spacious family room and sun-filled dining area overlooking the backyard oasis. Upstairs, the expansive loft provides exceptional flexibility as a media room, home office, fitness space, or could easily accommodate a fourth bedroom. The secondary bedrooms are generously sized, including one with a charming custom-built window desk. The beautifully updated bathrooms continue the home’s timeless design with quality finishes throughout. Step outside to your own private retreat featuring a sparkling pool, expansive brick paver deck, lush landscaping, and plenty of room for entertaining or simply relaxing under the Florida sun. Homes in Courtlea Oaks are rarely available. Combining an exceptional location, beautiful updates, timeless architecture, and one of Winter Garden’s most desirable lifestyles, this is a home you’ll be proud to call your own.

Listing is courtesy of: LAKESIDE REALTY WINDERMERE INC (407-876-5575)

Listing Agent: Jennifer Coon (321-948-8056)

Remarks: Some homes are simply updated. This one has a personality all its own. Welcome to this one-of-a-kind 4-bedroom, 4-bath home in the gated community of Carriage Pointe, where artistic design, modern renovations, and exceptional indoor-outdoor living come together to create a truly unforgettable home. This oversized 0.34-acre corner lot sits on a quiet dead-end street with no neighbors to the left or rear. Mature privacy hedges surround the fenced backyard, creating a peaceful retreat, while two gated community entrances provide convenient access to shopping, dining, and major roadways. From the moment you arrive, the home impresses with its stacked stone façade, paver driveway, oversized 3-car garage, and professionally landscaped grounds featuring majestic oak trees, palms, agave, and decorative rock landscape beds. Inside, every detail has been thoughtfully designed. Updated flooring, beautifully renovated bathrooms, plantation shutters, and brand-new Reece impact-rated windows provide modern comfort, while artistic finishes add a distinctive character rarely found in residential homes. The welcoming foyer and formal living and dining spaces feature custom faux brick and textured wall finishes created by an artist who contributed to the Wizarding World attractions at Universal Orlando. The beautifully renovated kitchen is designed for everyday living and entertaining with dramatic black-and-white quartz countertops, a full-height matching backsplash, a stunning waterfall-edge island, abundant cabinetry, breakfast bar seating, and a sunny breakfast nook overlooking the spacious family room. The spacious primary suite offers a private retreat with a custom designer accent wall, dual walk-in closets, and a luxurious bath featuring dual vanities, a soaking tub, and a large frameless glass shower. Two secondary bedrooms share a convenient Jack-and-Jill bath, while the fourth bedroom and additional full bath provide flexibility for family, guests, or a home office. A standout feature is the private upstairs bonus room with its own full bath. Professionally soundproofed and currently used as a DJ studio, this versatile space can easily become a recording studio, podcast room, theater, gaming lounge, fitness space, office, or private guest suite. Enjoy Florida living year-round in the enclosed sunroom with insulated ceiling, creating a comfortable extension of the home's living space. Beyond awaits an incredible backyard retreat featuring a beautifully designed raised paver gathering space anchored by a grand wood-burning fireplace, creating the perfect outdoor setting for entertaining, relaxing, and enjoying evenings under the stars. Professional landscape lighting and mature privacy landscaping complete this special outdoor escape, with plenty of room to play, garden, or add a future pool. If you've been searching for a home that feels anything but ordinary, you've found it. With its creative design, thoughtful updates, versatile spaces, and unforgettable backyard, this is more than a home - it’s a place where memories are made.

Listing is courtesy of: KEENE'S POINTE REALTY (407-876-8879)

Listing Agent: Angela Durruthy (407-496-5811)

Remarks: Under contract-accepting backup offers. Welcome to Hickory Hammock in famous Winter Garden. This 5 bedroom, 4 bath home features wood look plank tile flooring throughout the ground level, with wood ceiling beams and custom built in cabinetry in the family room. With dual water views this lovely home is situated a short distance to the amenity rich clubhouse, with zero entry pool, indoor lounge with kitchen, tennis courts, volleyball court, full gym, and playground. Also residents have access to nature trails, a dock on Johns Lake and 2 dog parks. The vibrancy of Winter Garden is well known with its historic Downtown Plant St just minutes away. A farmer’s market, splash pad, many shops and restaurants, and the West Orange Trail make this one of the most active small towns in Central Florida. Being closely connected to HWY 429 provides easy access to all else Florida has available. Highly rated schools. MORTGAGE IS ASSUMABLE. Note: Please refer to floorplan at end of photos to illustrate additional bedroom and walk-in closet. These rooms are not shown in virtual walkthrough for home office privacy. Can be toured at showings.

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Hardy Edwards (213-924-7010)

Remarks: Space, privacy, and thoughtful design define this beautifully maintained 5-bedroom, 3-bath residence in the gated community of Wintermere Harbor. With 3,249 square feet of living space, a 0.33-acre lot, private saltwater pool and a three-car garage, this home offers the kind of everyday functionality that's increasingly difficult to find. A grand entry welcomes you into elegant formal living and dining rooms for more formal occasions while the expansive family room and kitchen create a comfortable gathering place at the heart of the home. Whether hosting holiday dinners, celebrating milestones, or enjoying a quiet evening in, the layout adapts effortlessly to every season of life. Positioned on its own side of the home, the primary suite offers a welcome sense of separation from the secondary bedrooms featuring its own private entry/exit to the pool deck. The spacious primary bath is designed for comfort, featuring dual vanities, a relaxing garden tub, a separate shower, and two walk-in closets that provide exceptional storage and organization.The thoughtfully designed layout continues with five generously sized bedrooms and two additional full bathrooms providing flexibility for growing households. Upstairs, a spacious bonus room awaits, adding another layer of possibility as a media lounge, game room, home office, or even a 6th bedroom with the addition of a closet. Beyond the interior, the home's outdoor living space invites you to slow down and stay awhile. A fully fenced backyard offers privacy, room for pets to roam while the screened enclosure surrounds the sparkling saltwater pool, creating a comfortable setting for morning swims, weekend gatherings, or evening entertaining. Located within one of Winter Garden's most established gated communities, Wintermere Harbor offers a peaceful residential setting just minutes from Historic Downtown Winter Garden, Winter Garden Village, SR-429, the Florida Turnpike, shopping, dining, golf, and Orlando's celebrated attractions. Some homes simply offer more square footage. Others offer a floor plan that lives beautifully. Schedule your private showing today and discover everything this exceptional Winter Garden home has to offer!

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: John Chiumento (850-591-1689)