373 houses for sale in Winter Oaks, Winter Garden city Winter Garden-Ocoee CCD Orange County Florida

Back on market! Wow! Recent price drop by $10,000 and $3500 lender credit offered with jason baker at primis mortgage! Welcome to this stunning 5 Bed, 3 Bath Pool home located on the 14TH HOLE in the esteemed community of Stoneybrook West in Winter Garden! Offering more than 3,000 square feet of living space, this residence combines elegance with functionality. You’ll be greeted by beautiful landscaping with stone accent columns as you walk up the pavered driveway to the front door. Step inside to the open floor plan with formal living room and dining room to each side of the foyer, and high ceilings and modern light fixtures throughout the home. Double doors open up to a bonus room, that can be used as a bedroom, game room, office, or other flexible space. The spacious kitchen boasts modern appliances, cabinetry with crown moulding, tile backsplash and a massive wrap-around breakfast bar overlooking the family room. A dinette is conveniently located just off the kitchen. The huge prim

Rare Gated Lakefront Retreat with Grandfathered Boat Access on Lake Luntz Discover resort-style living in this one-of-a-kind gated lakefront home in the heart of Winter Garden. Nestled on a quiet, tree-lined cul-de-sac, this 5-bedroom, 5-bathroom, 4,365 Sq Ft home offers a smart layout designed for both everyday living and entertaining. The first-floor bedroom and full bath are ideal for guests or multi-generational living, while upstairs includes a loft, media room, and three additional bedrooms, including one en-suite and a Jack-and-Jill setup. Enjoy endless lake views from the screened pool with grotto seating and waterfall, or entertain indoors in the Florida Grillu002FBar room featuring a refrigerator, freezer, deep fryer, griddle, bar sink, dishwasher, and full poolu002Fguest bath. The primary suite is a true retreat with double walk-in closets, spa-style bath, garden tub, walk-in shower, and dual water closets. Lake enthusiasts will love the boathouse, covered dock, and boat lif

One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown m

Under contract-accepting backup offers. Canopy Oaks, located in Winter Garden, Florida, is a unique blend of high-end luxury homes and suburban tranquillity. This gated enclave, developed by the distinguished home builder A. R. Bailey, features 49 classic estates. The meticulously crafted community is designed to cater to the specific needs and desires of homeowners, and includes a scenic nature trail, a children’s play park, and a community post office. From the moment you arrive at this Mediterranean POOL estate home, it makes a BOLD statement with its 8-foot Solid Wood Arched double entry doors. You are greeted with cathedral ceilings, solid wood oversized French doors to the private office, elegant hand forged custom iron railings, and a unique wine cellar with a custom hand forged iron gate. Luxury details and fine craftsmanship are inside this 5 BR/4.5 Ba/2-car garage POOL home. Open Floor plan leads pleasantly into the chef-style kitchen with the perfect layout for entertaining.

Under Construction. Introducing an extraordinary luxury estate by Element Home Builders in the sought after Briley Farm community, where timeless design, exceptional craftsmanship, and modern elegance come together on a beautiful oversized, nearly half acre corner lot. This remarkable 6-bedroom, 6.5-bath custom residence offers an unparalleled living experience with every detail thoughtfully curated for comfort, sophistication, and style. From the moment you arrive, the home commands attention with its architectural presence and grand entryway. Inside, soaring ceilings, designer finishes, and expansive living spaces create a refined yet inviting atmosphere. The heart of the home is the gourmet chef’s kitchen, seamlessly connected to the main living areas and perfect for both intimate gatherings and large-scale entertaining. A private office provides the ideal work-from-home environment, while multiple ensuite bedrooms ensure comfort and privacy for family and guests. The 4-car garage o

Welcome to your next home in the heart of Winter Garden—where location, lifestyle, and upgrades come together seamlessly. This beautifully updated 3-bedroom, 2-bathroom home with an additional 135-square-foot flex space is perfectly positioned just 20 minutes from Disney, 15 minutes from Downtown Winter Garden, and only 10 minutes to Winter Garden Village, giving you easy access to everything Central Florida has to offer. Step inside to find brand-new luxury vinyl flooring, fresh exterior paint (2024), and a bright, open feel that makes the home both inviting and functional. The additional 135-square-foot living space under air conditioning, complete with elegant French doors, offers endless possibilities as a home office, playroom, fitness room, or second living area. Out back, enjoy your own private putting green—ideal for unwinding or entertaining guests. And with HOA-maintained landscaping, you can say goodbye to yard work and hello to low-maintenance living. Major updates bring pe

4.5 acres in Ocoee, FL close to everything! This parcel is nestled down a dirt road and offers a haven of privacy. Surrounding properties host commercial uses, opening the door to various commercial possibilities; however, it's advisable to consult with the City of Ocoee to ensure compatibility with your intended use as this property is currently zoned R-1. While a significant portion of the property is designated as flood zone AE, the city proactively addressed drainage concerns by digging a ditch along the western edge of the property a few years ago. This ensures that the property drains quickly and has efficient water management. The existing structure is likely a tear down, but the true value lies in the expansive 4.5 acres of land. This presents an exciting opportunity for those envisioning a large food forest or wanting to utilize the space for large format storage needs. Whether you're dreaming of a commercial venture or a unique agricultural project, this acreage offers a canv

Welcome to this beautifully maintained home located in the highly desirable Independenceu002FHorizon West community of Winter Garden! This spacious home showcases thoughtful upgrades and a bright open layout designed for modern living. The gourmet kitchen is the centerpiece of the home, featuring luxury cabinets, premium finishes, and ample counter space that flow seamlessly into the family and dinning areas. Elegant crown molding adds a touch of sophistication throughout, while European-style blinds bring a modern and functional design element to every room. The primary suite offers a peaceful retreat with a walk-in closet, complemented by well-sized secondary bedrooms. Enjoy Florida living with a covered patio, landscaping backyard, and two-car garage for convenience. Located just minutes from Disney, Hamlin Town Center, top-rated schools, shopping, dining, and major highways, this home is perfectly situated for both comfort and lifestyle. Don't miss the opportunity to own this beaut

One or more photo(s) has been virtually staged. Welcome to 15558 Sandfield Loop, a refreshed residence offering a turn-key lifestyle within one of Winter Garden’s most exclusive and hard-to-find GATED community. This house has been freshly updated from top to bottom, including new interior and exterior paint that makes the whole place feel brand new. The first thing you'll notice when you walk in is the massive, two-story high ceiling in the living area—it brings in tons of natural light and gives the home a great, airy feel. The kitchen has been fully redone with modern two-tone cabinets and beautiful quartz countertops. Throughout the home, you will find fresh paint and new flooring that perfectly complement the contemporary aesthetic. Situated within a highly-rated school zone, this MOVE IN READY property combines the security of a premier gated community with grand architectural features and stylish updates

Discover this beautiful Mediterranean-style two-story home in the gated community of Wesmere, off Maguire Road in Ocoee, Florida. Featuring 4 bedrooms and 2.5 bathrooms, this home offers an open, light-filled layout with tile flooring throughout the first floor. The spacious living area includes a versatile dining space, a bar area outside the kitchen perfect for entertaining, and a half bath with a modern vanity and LED-lit mirror. The kitchen has large cabinets, sleek countertops, energy-efficient stainless steel appliances, and a cozy breakfast nook overlooking the fenced backyard ideal for pets and gatherings. Notably, there’s no carpet throughout the home for easy maintenance. Upstairs, enjoy a luxurious master retreat with an en suite bath featuring a soaking tub, glass shower, and double vanities. Three additional bedrooms share a second full bathroom with a double vanity and sliding shower. The home is energy-efficient and includes an upstairs laundry room for added convenience

Welcome to 831 Lost Grove Circle in Winter Garden, FL! Located in the established Grove Park community built by M/I Homes just 5 minutes to Historic Downtown Winter Garden, resale opportunities don't arise in this intimate community often. This expansive home with lush landscaping and over 3,400 square feet features 5 bedrooms, 4 bathrooms, a 3-car garage, heated pool and spa (custom designed in 2020) + enclosed paver pool deck, and sits on an oversized fully fenced in lot with no rear neighbors. Recent updates include a brand-new roof, brand-new water heater, and two newer hvac units installed in 2022. The first floor includes a living room with a stunning pool view, large kitchen with dining nook, quartz countertops with wall to wall cabinetry, formal dining room, flex room, one bedroom, a full bathroom, and a laundry room. Upstairs, there’s a large loft, the primary bedroom (large walk-in closet, office/sitting nook, dual vanities, walk-in shower, and soaking tub) PLUS three additio

Welcome to Woodbridge on the Green—one of Winter Garden’s best-kept secrets, ideally situated next to West Orange Country Club. Enjoy your own private waterfront retreat, where tranquil surroundings and breathtaking sunsets over the water create the perfect setting to share unforgettable moments with family and friends! This beautifully maintained waterfront home offers exceptional curb appeal and a spacious, single-story layout designed for comfortable living. Step inside to an inviting open floor plan filled with natural light and waterfront views. High ceilings and stylish luxury flooring enhance the home’s modern feel, creating a bright and airy atmosphere throughout. The well-appointed kitchen features custom countertops, rich wood cabinetry, and a full appliance package, with culinary nook overlooking the peaceful & gorgeous waterfront—perfect for both everyday living and entertainment. The generously sized primary suite provides a peaceful retreat, complete with closet, dual van

Stunning two-story Mattamy Homes Kensington model, built in 2019, offering 3,202 sqft of beautifully designed living space on an oversized 11,056 sqft cul-de-sac lot. Situated on one of the most desirable lots in the community, this exceptional property offers outstanding privacy with no rear neighbors and a fully fenced backyard with endless possibilities—create your dream pool, outdoor terrace, garden, or any outdoor living concept you envision. As you enter, you are welcomed by a spacious flex area and 9-foot ceilings throughout the first floor, enhancing the open and airy feel. The heart of the home is the fully upgraded modern kitchen featuring white cabinetry, quartz countertops, stainless steel appliances, a built-in double oven, cooktop, large center island, and a spacious walk-in pantry, all opening seamlessly to the family room highlighted by a custom accent wall with built-in shelving—perfect for everyday living and entertaining. The first floor also features new luxury viny

Nestled in the highly desirable Wesmereu002FCheshire Woods community! This beautifully maintained 4-bedroom, 2-bath home offers comfort, space, and timeless appeal. Lovingly cared for by its original owner, it reflects true pride of ownership throughout. As you step inside, you’re welcomed by a formal living and dining room area that creates an elegant and inviting first impression. The layout then opens into a spacious kitchen and family room combination, ideal for both everyday living and entertaining. The kitchen features a bright bay window in the nook area, filling the space with natural light. All premium stainless steel kitchen appliances are included, an excellent added value for the new owners. Sliding glass doors from the family room lead to an expansive Florida Room, offering a versatile extension of the home perfect for a second living area or just a relaxing retreat. Residents of Wesmereu002FCheshire Woods can enjoy two gated entrances, tennis, pickleball and basketball co

Welcome to one of Windermere’s finest offerings — an impressive 6-bedroom, 4.5-bath estate spanning almost 6,000 sq ft on a premium 0.62-acre direct water-view lot in the exclusive 24-hour guard-gated community of Tildens Grove. This is a luxury build that combines sophistication with fun and accommodates an active lifestyle for family and entertaining. Enjoy a resort-style pool with spa and panoramic screen overlooking the water, gourmet kitchen, a dedicated gym, plus two generous family u002F entertainment spaces upstairs and down… all create a floor plan that handles both grand entertaining and relaxed everyday living. Updates to HVAC, lighting, fixtures, media systems, and wood flooring throughout. Soaring ceilings with architectural features, and elegant architectural details define every room. Bedroom layout creates a lot of options with one of the downstairs bedrooms featuring a separate side entry just off of the driveway with direct access to a full bathroom. Ideal for guests

Under Construction. Under Construction Custom Home by Element Home Builders. Welcome to your dream home in Briley Farm. Briley Farm is one of Central Florida's most desirable custom home communities. The property is a seamless blend of charming Old Florida and modern-day luxury. Briley Farm consists of 111 acres of lush landscape in Oakland, Florida. The personal residence is a custom blend of luxury finishes and stunning design. All measurements etc are estimates

Welcome Home to The Village of Wesmere 457 Mickleton Loop, Ocoee, FL 34761 4 Bedrooms | 2 Bathrooms | Screened Pool | Gated Community. Experience the perfect blend of modern life and resort-style living in the highly sought-after Cheshire Woods subdivision of Wesmere. This meticulously maintained residence offers a peaceful lifestyle within a premier gated community, designed for those who value comfort, connectivity, and convenience. Step inside to discover a bright, airy floor plan characterized by soaring vaulted ceilings and premium finishes. The heart of the home features porcelain tile flowing through the kitchen, dining, and family rooms. The kitchen opens seamlessly to the living areas—ideal for entertaining. Recent Refresh: Enjoy peace of mind with interior and exterior paint (2017), new carpeting in secondary bedrooms, and a new driveway and sidewalk (2019). Outdoor Oasis: Your private retreat awaits in the massive backyard. The screened-in pool is solar-heated for year-round

This beautiful townhouse is located in the gated community of Westyn Bay and offers modern 2015 construction, thoughtful updates, and true move-in-ready comfort. Well-maintained by the original owner, the home features brand-new carpet, a brand-new granite countertop, new GE stainless-steel refrigerator and dishwasher, and a new washer and dryer. The open-concept main floor provides great natural light and flexible living space. Upstairs, the split bedroom layout offers privacy, with a spacious primary suite featuring dual sinks and a walk-in shower. The upstairs laundry adds everyday convenience. Enjoy two outdoor living spaces: a welcoming front porch and a covered screened patio, perfect for morning coffee, relaxing evenings, or year-round entertaining. The home also includes a 1-car garage and a convenient under-stair storage space ideal for packages, pantry items, or everyday essentials. Westyn Bay offers beautiful landscaping and community amenities including a pool, basketball a

Charming 3-bedroom, 1.5-bath home on a spacious 0.34-acre corner lot in the heart of Ocoee. Recently Rented with one year lease ending in February 2027. This home features a bright, open layout with original character and recent updates, including a newer roof, newer water heater, and vinyl double-pane windows. The fully fenced yard offers plenty of space for pets, gardening, or entertaining. Located directly across from Central Park with a basketball court, baseball field, and a skate park next to a lake. No HOA and just minutes from downtown Ocoee, major highways, shopping, schools, and parks. A great opportunity for first-time buyers, investors, or anyone looking for a home with room to grow

Welcome to this beautifully maintained 5-bedroom, 3-bathroom home located in the highly desirable community of Crown Pointe Cove in Ocoee. Built in 2017 and offering nearly 2,600 square feet of living space, this spacious two-story residence combines modern design, functionality, and comfort which is perfect for growing families or those who love to entertain. Step inside to an inviting open-concept layout featuring a generous living and dining area that flows seamlessly into the kitchen which is ideal for hosting gatherings or everyday living. With multiple bedrooms and a flexible floor plan, this home offers plenty of space for guests, a home office, or multigenerational living. The home sits on a well-sized lot in a quiet, well-kept neighborhood, offering both privacy and community charm. Residents enjoy a peaceful setting while still being conveniently located near major roadways, shopping, dining, and top-rated schools. Located in the heart of Ocoee, you’re just minutes from Winte

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 u002F 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 bedr

Location location location! This beautiful 3 bedrooms, 2 1/2 baths, includes a spacious open floor plan with a breakfast bar in the kitchen area and Living Room/Dining Room Combo. Master Bedroom is located on the second floor, as well as two more bedrooms. This two car garage townhouse has a charming front porch which overlooks the pond and offers, not one, but two community pools and a playground area. The Vineyards of Horizon West community offers easy access to SR-429, SR-535, and US-192 and area employers, including Walt Disney World, Orange County National Golf Center and Lodge, and Universal Orlando Resort. The community is also close to several excellent dining and shopping options, including Winter Garden Village and downtown Windermere

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

Virtually Staged. Brand New HVAC May 29, 2026-. Welcome to this 3-bedroom, 2-bath pool home in the Cross Creek community of Ocoee—offering a spacious layout, high ceilings, and the indoor-outdoor lifestyle Central Florida buyers are looking for. Situated on a. 22-acre lot, this home combines functional living space with a private outdoor setting designed for year-round enjoyment. From the moment you enter, soaring ceilings and abundant natural light create an open, airy feel throughout the main living areas. The layout features formal living and dining spaces that flow seamlessly into the kitchen and family room—ideal for both entertaining and everyday living. The kitchen offers ample cabinet storage, all appliances, and a cozy dinette area, making it both practical and inviting. A dedicated laundry closet with washer and dryer adds convenience without sacrificing space. At the center of the home, the family room opens directly to the covered, screened patio and private pool, creating

Motivated Seller! Just reduced 20k! 2748 Palastro Way could be the one! Westyn Bay is a 24hr gatedu002Fguarded community with loads of amenities! Huge house! 5u002F3 3758 sq ft with 1u002F1 on 1st floor for guests or multi-generational living solutions. The wheel-chair friendly guest suite also has an outside entrance onto the downstairs covered porch. The formal living and dining room spaces are adjacent to a dramatic entryway. New roof in 2022, exterior paint in 2023 & both ac's replaced in 2024! Competitively priced for updates needed. The ISLAND KITCHEN overlooks the family room & back yard. It features a breakfast bar, elegant granite countertops with classic 42' maple cabinetry & walk-in pantry. Lots of light! Beazer Homes nailed it with this luxurious master suite in their Chardonnay floorplan! It features a tray ceiling, covered balcony access and a 10X12 SITTING AREA or WORK OUT SPACE just for you (pre-plumbed for a wet bar)! PLUS the en suite master bath featuring a soaker tu