Homes for Sale Near West Orange High in Winter Garden - 166 homes

Remarks: Short Sale. Don't miss this beautifully updated 2-bedroom, 2-bathroom townhouse offering the perfect blend of comfort, convenience, and unbeatable location. Tucked away in a quiet community, this home is just minutes from all the charm and excitement of downtown Winter Garden, known for its boutique shopping, top-rated restaurants, farmers market, splash pad, and the scenic West Orange Trail. Inside, you'll find a thoughtfully updated interior offering easy, low-maintenance living. Perfect for first-time buyers, downsizers, or investors looking for a move-in ready property in one of Central Florida's most sought-after towns. With its prime location close to shopping, dining, parks, and major roadways, this townhouse offers an unbeatable opportunity to enjoy the best of downtown Winter Garden living without the downtown price tag. Schedule your showing today!

Listing is courtesy of: REAL BROKER, LLC (407-922-8986)

Listing Agent: Denise Pellegrino (352-978-9720)

Remarks: WOW!!! OVER $40,000 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)

Remarks: Virtually Staged. Step into a home designed for the way you truly want to live. From its elevated concrete construction to its hurricane-rated engineering, this residence offers the rare combination of luxury, security, and effortless comfort. Natural light fills the interior, where level-5 walls, rich wood flooring, crown molding, and custom shutters create a warm, refined atmosphere. The heart of the home is the open living and kitchen area—perfect for gathering, cooking, and connecting. A gas range, pot filler, and handcrafted cabinetry make everyday meals feel elevated. Slide open the dramatic retractable pocket door and the entire space transforms into an indoor-outdoor retreat. The back porch is built for hosting: pecky cypress bar, industrial finishes, automated screens, garage-style doors, mini-split A/C, 1/2 bath, and room for everyone to unwind. The primary suite is a sanctuary of its own, offering a spa-inspired bath with dual shower heads, soaking tub, and digital controls. A custom closet and private concrete safe room add both convenience and peace of mind. With a butler’s kitchen, wine bar, dedicated office, and whole-home CAT-5 wiring, this home is designed for modern living at its finest—where every detail supports a lifestyle of ease, elegance, and connection. Upstairs, the bonus/game room and oversized balcony access create the perfect hangout zone. You won't complain about storage or closet space as most rooms have walk-in closets and the additional closets are oversized as well. Let your imagination run wild because the possibilities are endless with the finished two-story garage loft that is pre-plumbed and air conditioned! Mother-in-law suite, man cave with a golf simulator or a gym, home office or game room. Outside, the home is framed by curated Florida landscaping, gas lanterns, an architectural driveway, and a built-in heated concrete hot tub with Wi-Fi controls—ideal for quiet evenings or weekend entertaining. Fiber-cement siding, Ipe hardwood porch, impact windows, and full foam insulation ensure long-lasting beauty and efficiency. Prime location near Downtown Winter Garden’s brick-lined streets, upscale dining, boutique shopping, award-winning Farmers Market, Plant Street Market, Crooked Can, the West Orange Trail, and the historic Garden Theatre — a truly elevated lifestyle.

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

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

Remarks: Bedrooms & bathrooms Bedrooms: 3 Bathrooms: 2.5 Cooling Central Appliances Included: Dishwasher, Dryer, Garbage disposal, Microwave, Range / Oven, Refrigerator, Washer Features Flooring: Tile, Carpet

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Fina Perez (407-780-6680)

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)

Remarks: Motivated Seller! Don't miss your opportunity with this Winter Garden home - offering elegance, convenience and affordability. Situated inside the desirable Waterside community, you will find this beautifully designed residence, blending timeless sophistication with modern comfort, offering an open floor plan, designer finishes, and exceptional indoor-outdoor living. From the moment you arrive, the charming covered front porch, mature landscaping, and inviting curb appeal set the tone. Inside, you're greeted by wide-plank luxury vinyl flooring, soaring ceilings, crown molding, and sun-filled living spaces designed for both everyday living and effortless entertaining. The gourmet kitchen is a true showpiece featuring granite countertops, an oversized center island with seating, farmhouse sink, white shaker cabinetry, stainless steel appliances, gas cooktop, double ovens, subway tile backsplash, a custom, handmade hood and designer pendant lighting. Flowing seamlessly into the spacious dining area and family room, this home is ideal for gathering with family and friends. Large sliding glass doors open to an expansive covered lanai with a stunning wood-finished ceiling, creating the perfect space to dine outdoors or just relax. The fully fenced backyard provides privacy, while maintaining a low-maintenance lifestyle. As you journey to the second level, you are greeting by a spacious loft, creating a retreat for unwinding and more closet space. Two large, additional bedrooms and a full bathroom are set off from the primary suite. Escape to your luxurious primary suite, offering a spacious walk-in closet and a beautifully upgraded spa-inspired bath, complete with a custom dual-sink vanity with quartz countertops, elegant gold fixtures, an oversized walk-in shower, and designer tile extending to the ceiling. Additional highlights include double-pane windows, custom window treatments, upgraded light fixtures, abundant storage, an oversized laundry room and pantry and thoughtful designer touches throughout. Residents enjoy outstanding resort-style amenities including a lakeside community pool, clubhouse, fitness center, playground, unfenced dog park and community dock. Ideally located in the heart of Winter Garden, this exceptional home is just minutes from shopping, dining, entertainment, theme parks, major highways, and top-rated schools. This isn't just a home; it's a lifestyle. Book your showing today!

Listing is courtesy of: ERA GRIZZARD REAL ESTATE (352-394-5900)

Listing Agent: Wendy Moore (678-575-5596)

Remarks: 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)

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)

Remarks: Just remolded!!!Large 4-bedroom home + 2 large Bonus rooms. This 2782sf 7-year-old home is in the awesome community of Lakeside just west of the Winter Garden Village about 4 miles. The home has tons of space, humungous kitchen and Master bedroom downstairs along with bedroom #2 and 3, and with a full bath. The first floor is gorgeous tile from the front door throughout up to the bedrooms. Coffered details in high ceilings, arched openings and a back yard looking over a green retention area. This Hampshire plan has a split plan with 2 bedrooms and full bath near the front of the house first floor. Walking past the flex room that can be used for formal dining, office, etc to the main open living area with living, dining, and kitchen. The kitchen is large with TONS of tall 42 inch raised panel cabinetry and walk-in pantry. The beautiful light brown speckled granite is accented by medium Brown cabinets and all stainless-steel appliances with the stove fueled with gas. A walk-in pantry and Island sink with breakfast bar look out to the open living room and dinette. Dinette has large windows on 3 sides to embrace the outside nature. The main living area has a 3-panel slider door to open wide to the paved, covered Lania that overlooks a good-sized back yard with a large field retention area beyond. Past the living room through the arched entry into the large primary bedroom. Ceiling fan and high coffered detailed ceilings and a huge bath with a seated walk-in shower separating two individual vanities on large cabinets for lots of storage. Large walk-in closet, separate toilet room, and linen closet. Washer and dryer have their own room near the garage. Take a quick step upstairs to a HUGE open loft, 4th bedroom and 3rd full bath. full bath. This home has a 2 car garage and gas heated Tankless water heater. This home is located in the awesome community of Waterside at Johns lake, with an incredible huge pool lakeside, playground, dock, clubhouse, state-of-the-art fitness center

Listing is courtesy of: SPRING REALTY ONE LLC (407-340-1754)

Listing Agent: Chun Cai (951-699-4983)

Remarks: Mediterranean Elegance Meets Lakeside Luxury on John's Lake! Welcome to your own private paradise, nestled in the exclusive, small gated waterfront enclave of John’s Cove. Step inside this gorgeous, custom-built estate and be instantly captivated by soaring 25-30 foot vaulted ceilings, a dramatic winding staircase, elegant Roman-style arches and columns and abundant natural light. In this spectacular 4-bedroom, 4.5-bath pool home you'll enjoy breathtaking views of the pristine, spring-fed John’s Lake from almost every room, delivering all the scenic beauty without the hassle, upkeep, or worries of lakefront maintenance! A formal dining room and formal living room, both with soaring ceilings, adorn each side of the grand staircase. The heart of the home is a gourmet kitchen featuring brand-new stone tile backsplash, granite countertops, abundant wood cabinetry with crown molding, and two islands, both with sinks and bar seating. The chef of the family will appreciate the newer stainless steel appliances, 5-burner gas cooktop with a pot filler and convenient “prep” sink in addition to a separate double-bowl sink. Enjoy sipping coffee while watching the sun rise through the trees, over the water in the cozy breakfast nook, which perfectly frames your gorgeous pool and lake views. The kitchen overlooks the spacious family room anchored by a custom mantel gas fireplace with French doors to the outdoor kitchen. The luxurious first-floor primary suite is a true retreat, offering tranquil views with private access to the outdoor pool patio. It features his-and-her walk-in closets—one uniquely doubling as a highly secure panic/safe room with a steel door and 12-inch concrete walls! The en-suite spa bath features an oversized tub, a circular walk-in shower, and dual vanities. A versatile fourth bedroom downstairs is conveniently located across a full bath, and provides excellent additional living space that can easily transition into a home office, den, or flex room. Upstairs, you will find two generously sized bedrooms—including a private suite with its own full bathroom—both boasting access to a second-floor balcony with sweeping treetop lake views. A splendid column-clad catwalk leads to the stadium-seating theatre room (which can easily serve as an additional home office or den) and a full hallway bath complete the second floor. Step outside to your spectacular outdoor oasis. The expansive screened patio encloses a resort-style heated pool and spa (built in 2017) complete with a sun shelf, fountain, and elegant pavered decking. Entertain with ease at the outdoor summer kitchen featuring a built-in grill, countertop space, and a mini-fridge. This home has a fresh coat of exterior paint, newer AC, new water heater, and direct lake access is just steps away via the private community boat ramp. Water enthusiasts will love the easy access for recreational boating, skiing, tubing, and sport fishing on this sprawling 2,500-acre lake that feels like a chain of lakes. You CAN have it all in this fabulous Florida oasis that feels miles away from it all, yet is just minutes from the Turnpike, SR 429, SR 408, downtown Winter Garden, as well as the best shopping, dining and entertainment in all of Central Florida!

Listing is courtesy of: GILKEY REAL ESTATE (407-712-3111)

Listing Agent: Jason Gilkey (407-712-3111)

Remarks: UPDATED TOWNHOME NEXT DOOR TO CROOKED CAN & PLANT STREET MARKET! Located in the heart of Downtown Winter Garden, 461 Geranium Park Way offers one of the most connected lifestyles available — coffee, dining, craft beer, the West Orange Trail, live music, community events, and the Saturday Farmers Market are all right outside your door. Inside, the home feels practically new, with fresh paint throughout and an exceptionally well-maintained interior that shows beautifully. Bright, polished, and truly move-in ready, the home features wood-look tile flooring, crisp white trim, crown molding, recessed lighting, modern door hardware, decorative wall trim, and a clean neutral design throughout. The open main living level is ideal for everyday living and entertaining, with the kitchen, dining, and living areas flowing together in one spacious, connected layout. The kitchen features light cabinetry, stone countertops, subway tile backsplash, stainless steel appliances, a NATURAL GAS RANGE, vent hood, pendant lighting, and an oversized island with seating. The dining and living areas offer generous space, abundant natural light, balcony access, and a comfortable layout that feels open, stylish, and easy to live in. The flexible three-level design includes three ensuite bedrooms, offering excellent privacy and flexibility for guests, family, work-from-home needs, hobbies, or multi-generational living. The first-floor ensuite bedroom creates a private retreat away from the main living areas, while upstairs, the spacious primary suite offers a beautifully updated bath with dual vanities, new flooring, and a BRAND NEW STEAM SHOWER with floor-to-ceiling tile, built-in bench, recessed niche, decorative tile accent, and a spa-inspired look. An additional ensuite bedroom, laundry, excellent storage, and an ELEVATOR-READY layout add to the home’s long-term functionality. Additional highlights include NATURAL GAS SERVICE, tankless water heater, updated fixtures, two-car garage, landscaped courtyard setting, and a cohesive modern feel throughout. With its fresh interior, updated finishes, open main living level, natural gas features, flexible floor plan, and unmatched Downtown Winter Garden location, this home offers a rare blend of comfort, convenience, and everyday enjoyment. Spend Saturday mornings at the Farmers Market, meet friends on Plant Street, hop on the West Orange Trail, and come home to a beautifully updated, low-maintenance townhome just steps from it all. Schedule your private showing today.

Listing is courtesy of: THE ROSENBLOOM TEAM (407-376-4454)

Listing Agent: Cindy Rosenbloom (407-876-9175)

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 (646-480-7665)

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

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)

Remarks: Virtually Staged. Nestled in the highly sought-after Oakland Park community, this beautifully maintained 3-bedroom, 3-bath home is the definition of move-in ready living. Featuring desirable upgrades throughout, including gas appliances, elegant plantation shutters, and a turnkey design, this home offers the perfect blend of comfort, style, and convenience. Enjoy open-concept living spaces filled with natural light, spacious bedrooms, and a layout designed for modern living and entertaining. Pride of ownership shines in every detail, making this home truly stand out. Located in a charming golf cart community with resort-style amenities, residents enjoy access to parks, schools, walking trails, and more. Just minutes from vibrant Downtown Winter Garden, you'll love being close to the award-winning farmers market, lively festivals, boutique shopping, dining, and entertainment. This is your opportunity to own a well-maintained, upgraded home in one of Winter Garden's most desirable communities!

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

Listing Agent: Erica Diaz (407-897-5400)

Remarks: Virtually Staged. Tucked away on a cul-de-sac within the gated community of Wintermere Pointe, this spacious 5-bedroom, 4-bath pool home is situated on an oversized homesite of more than 1/4 acre with a beautiful wooded backdrop. The private backyard provides an inviting setting for outdoor living, featuring a screened pool and patio that create the perfect space for entertaining or simply enjoying the natural surroundings. Designed with one of the community’s most sought-after floor plans, this home offers exceptional flexibility with generous living spaces throughout. The formal living and dining rooms are sized to accommodate large furniture, while the centrally located family room flows seamlessly into the kitchen and outdoor living areas. The home office is thoughtfully positioned adjacent to the primary suite, making it equally suitable as a fifth bedroom, nursery, den, or private workspace. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, abundant cabinet storage, and a full appliance package, including a 5-burner glass cooktop range with a convection oven. The adjacent dinette overlooks the pool and backyard, while replacement sliding glass doors installed in 2017 provide direct access from the living room, dinette, family room, and primary suite to the screened patio and pool. The spacious primary suite features wood flooring, coffered ceilings, double closets, and oversized sliding glass doors that open directly to the pool area. The ensuite bath features dual vanities with stone countertops, a relaxing garden tub, a separate shower, and a private water closet. The secondary bedrooms are generously sized and conveniently located for easy access to the home’s full bathrooms, each enhanced with updated vanities and mirrors. A full bath located just off the family room also serves as an ideal pool bath. Just beyond the kitchen and laundry room, a hallway provides access to the 3-car garage and a wood staircase leading to the expansive bonus room. Complete with a full bath, walk-in closet, and newer windows overlooking the oversized backyard and wooded backdrop, this versatile space is ideal as a guest suite, sixth bedroom, recreation room, media room, home gym, or private retreat. Numerous updates provide added value and peace of mind, including multiple replacement windows (2015), a new roof (2016), replacement sliding glass doors and front entry door (2017), a new paver driveway (2020), a new water heater (2020), and a new HVAC system (2025). Wintermere Pointe is a gated community offering residents a playground and tennis courts. Conveniently located with access to Lake Whitney Elementary, SunRidge Middle School, and West Orange High School, the home also provides easy access to shopping, dining, major roadways, and many of Central Florida’s most popular destinations.

Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)

Listing Agent: David Dorman (407-948-8295)

Remarks: Welcome to this beautifully renovated single-story gem nestled in the heart of Historic Winter Garden, one of Central Florida’s most sought-after communities. Perfectly situated just two blocks from vibrant downtown Winter Garden and iconic Plant Street, this home offers the ultimate blend of historic charm, modern luxury, and walkable convenience. Located within the highly desirable golf cart district and just moments from the renowned West Orange Trail, you’ll enjoy easy access to cobblestone streets, boutique shopping, coffee houses, award-winning restaurants, and the beloved Saturday Farmer’s Market — all right outside your door. Completely renovated from top to bottom, inside and out, this move-in ready home showcases exceptional attention to detail and thoughtful upgrades throughout. Step inside to discover a bright open floor plan enhanced by luxury vinyl plank flooring, upgraded 6-inch baseboards, updated light fixtures, neutral designer finishes, and ceiling fans in every bedroom. The stunning remodeled kitchen serves as the heart of the home, featuring crisp white cabinetry, elegant quartz countertops, modern backsplash, dark designer hardware, LED lighting, stainless appliances, and an oversized island with seating for six — perfect for entertaining family and friends. The bathrooms have been tastefully updated to blend timeless character with modern functionality, while the inside laundry room and abundant storage, including two hallway closets near the secondary bedrooms, add everyday convenience. Outdoor living shines with a newly added tiled screened lanai complete with new sliding doors and windows that create seamless indoor-outdoor flow. The expansive fenced backyard is a private oasis featuring fresh landscaping, a Magnolia tree, Orange tree, and Avocado tree — the perfect setting to relax and enjoy Florida living year-round. Additional highlights include a brand-new AC unit, anti-slip garage floor coating, and a 6-foot white vinyl privacy fence. This one-of-a-kind home perfectly captures the charm of Historic Winter Garden while offering the modern updates today’s buyers desire. WELCOME HOME.

Listing is courtesy of: COLDWELL BANKER REALTY (407-333-8088)

Listing Agent: Peyton Blanton (407-462-7891)

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)

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: Under contract-accepting backup offers. This beautifully updated 3 bedroom, 1 bathroom home offers modern comfort at an unbeatable value. With 814 sq ft of living space, it features a brand-new roof, newer A/C, fresh interior and exterior paint, a fully remodeled kitchen with a new fridge, and brand new remodeled bathrooms—giving you peace of mind and a move-in ready lifestyle. Located in the heart of Winter Garden, this home is close to shops, dining, and entertainment, all while being tucked into a welcoming neighborhood. Whether you’re a first-time buyer, downsizing, or looking for an investment property, this gem checks all the boxes. Don’t miss this rare opportunity to own a beautifully renovated home in one of Central Florida’s most sought-after communities—for less than $300K! **All measurements must be verified by the buyer.**

Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)

Listing Agent: Christopher Sukhram (407-558-8460)

Remarks: An Irreplaceable Gated Estate: Unmatched Scale, Double-Lot Privacy, & Private Oasis Behind the gates of the highly coveted Waterside community, 16614 Harbor Sail Way breaks the mold of standard luxury builds. This is not a high-density, cookie-cutter residence; it is an established, substantial family estate defined by an extraordinary sense of space, meticulous craftsmanship, and structural authority. Positioned beautifully on an expansive, premium lot that nearly doubles the community average, this rare property offers a refined lifestyle designed for those who value space to breathe, long-term permanence, and effortless entertaining. While typical Mansfield floor plans in the neighborhood occupy a standard lot, this home’s visionary owners secured the adjacent parcel, resulting in a commanding 14,973-square-foot footprint. This unique layout introduces a majestic private turning circle with dedicated parking for an additional six vehicles (bringing total driveway capacity to ten)—ideal for hosting executive gatherings or multi-generational families. Beyond the striking courtyard entry, the residence spans an impressive 4,882 square feet of meticulously maintained living space, delivering structural scale that effortlessly handles the demands of modern family life. The heart of the home centers on a dramatic great room bathed in natural light, seamlessly connecting to a gourmet kitchen equipped with premium finishes and gas cooking. Every corner of the main level emphasizes functional luxury, including a private home office, formal dining room, a secluded guest suite, and a magnificent primary sanctuary. Ascending to the second level reveals a sprawling, open flex room suspended over the main living area that opens to a fully enclosed, private balcony, creating an incredible architectural anchor. This level features four additional large bedrooms and media room, offering families the chance to spend time together, or unwind in complete peace. For ultimate daily convenience, a built-in central vacuum system services the ground floor of the home. While neighboring homes may provide "room for a future pool," this estate delivers the ultimate outdoor lifestyle immediately. The west-facing backyard is a private, sun-drenched sanctuary featuring a spectacular custom salt-water pool and integrated spa. Surrounded by extended paver decking and lush, manicured grassed areas made possible by the expanded double-lot footprint, this outdoor space offers complete privacy with no direct rear neighbors—perfect for enjoying vibrant Central Florida sunsets. Living in Waterside means enjoying a resort-style lifestyle with access to a premier clubhouse, fitness center and community pool. You are uniquely positioned just minutes from Horizon West’s top-rated schools (Hamlin Elementary/Middle), West Orange (High), the charm of downtown Winter Garden, major executive corridors (SR-429, Turnpike), and premier dining and shopping. This is more than a home; it is a strategic asset of scarcity, privacy, and generational quality. Schedule your private tour to experience it firsthand.

Listing is courtesy of: GLOBAL FLORIDA REALTY (407-380-3030)

Listing Agent: Garry Walmsley (407-923-2134)