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

Presenting this exquisite modern residence standing alone without neighbors in either side or rear in a neighborhood of almost 150 homes showcasing souring ceilings, designer finishes, and an open-concept living space bathed in natural light. A gourmet kitchen that anchors the home, while expansive glass doors reveal a resort-style screened pool and outdoor lounge. Architecture, luxurious details inside all bathrooms and kitchen, and seamless indoor-outdoor living create an exceptional retreat for refined entertaining. An amazingly fancy electric chimney gives the living room area warmth and elegance. AC units are of high efficiency with hotel fragrance throughout the entire home. Come and see it soon! AC units is 3 years. New roof to be installed

Welcome to this charming single-family residence in the highly desirable Black Lake Park community of Winter Garden. This well-maintained home features 4 (3 bedrooms + 1 study) and 2 full bathrooms with a functional open floor-plan that seamlessly connects living, dining, and kitchen areas — perfect for everyday living and entertaining. The spacious interior offers approximately 2,365 sq. Ft. of living area on a ±8,178 sq. Ft. lot with no rear neighbors and lush landscaping for added privacy. Situated in a vibrant community with amenities including tennis and basketball courts, playground, pool and outdoor recreation areas, this property is conveniently located minutes from Winter Garden Village dining and shopping, major roadways (including the 429), and top-rated schools

Price improvement! This exquisite gem has endless opportunities: a wellness center, wedding event venue, and Airbnb. Not looking to own a bed and breakfast? This would also make a fantastic stately residential home! This distinctive 19th-century Oakland Manor House sits on an. 8-acre park-like setting in the charming town of Oakland. Carefully restored to preserve and enhance its original beauty with abundant woodworking, tall windows, 10’ ceilings, and elegant staircases. French doors connect the formal dining and living room to a grand Florida room with a hot tub and outdoor porch. A modern island kitchen features stainless steel appliances, 3 sinks, and a large pantry. A luxury updated master suite with a soaking tub is on the first floor, along with a private apartment with its own kitchen and separate entrance. The 2nd floor offers 4 themed bedroom suites, an upstairs living roomu002F lounge, and a porch with views of Lake Apopka. All rooms have an internet-based locking system. T

Move-in ready home located in the highly desirable guard-gated community of Stoneybrook West. This well-maintained property offers a bright and open layout with a functional split-bedroom floor plan designed for comfortable everyday living. The spacious primary suite features a walk-in closet, dual vanities, soaking tub, separate shower, A flexible bonus area just off the suite can easily serve as a home office, nursery, or additional bedroom. The kitchen provides ample storage and flows seamlessly into the main living space, making it ideal for both daily use and entertaining. The family room is highlighted by a cozy fireplace, adding warmth and charm. Enjoy the fully screened backyard with plenty of room to relax or entertain outdoors. Stoneybrook West residents have access to resort-style amenities, including lake access, multiple sports courts, a community pool, playground, fitness center, and an active Town Centre. Conveniently located near shopping, dining, and major highways, th

One or more photo(s) has been virtually staged. Welcome to 940 Marsh Reed Drive, a beautifully upgraded 5 bedroom, 3 bathroom, SOLAR HEATED POOL HOME offering just under 3,500 square feet of well-designed living space in the highly sought-after Johns Lake Pointe community! Additional office and loft u002f bonus room. Solar panels are paid off! From the moment you arrive, the home makes a strong impression with its tile roof, enhanced landscaping, and well manicured appearance, setting the tone for what’s inside. The interior opens to a bright, expansive layout with high ceilings, neutral finishes, and multiple living and dining areas designed for both everyday comfort and entertaining. The heart of the home is the open-concept kitchen, featuring abundant cabinetry, walk-in pantry, granite countertops, stainless steel appliances, extended butler's pantry style prep area, and a large center island that flows seamlessly into the main living area. Natural light fills the space, creating an

Pre-Construction. To be built. This is a pre-construction opportunity in partnership with Vazquez Family Builders. Final floor plan, square footage, and sales price will be determined by the buyer based on selected model and upgrades. Positioned on a desirable corner lot in the heart of Winter Garden, this pre-construction ranch-style home presents an exceptional opportunity to create your ideal living space. This home is planned for 1713 square feet of meticulously designed living space, featuring 4 spacious bedrooms, two full bathrooms, and an attached two-car garage. The open-concept layout will seamlessly connect the main living areas, creating an inviting environment for everyday life and entertaining. The absence of stairs makes this home highly accessible and a perfect 'forever home or vacation property. '

Price Improvement! Exceptional new value. Seller motivated. Welcome to this beautifully maintained 4-bedroom, 2-bathroom single-family home located in the highly desirable Garden Heights community of Winter Garden, offering a prime location with NO HOA. Recently improved in price, this home now presents an even stronger opportunity in today’s market, combining location, upgrades, and value in one of Winter Garden’s most sought-after areas. Thoughtfully designed with a functional split floor plan, this residence offers 1,700 sq ft of living space filled with natural light and two separate living areas that provide both comfort and flexibility. Sliding glass doors open to a brand-new screened patio (2025), creating the perfect indoor-outdoor lifestyle for relaxing or entertaining. The interior features a beautifully updated kitchen and bathrooms, luxury vinyl plank flooring throughout, and modern upgrades including a whole-house water filtration system. Set on an expansive 0.29-acre lot,

Welcome to an extraordinary Winter Garden retreat where luxury, flexibility, and resort-style living come together in one remarkable residence. Situated on a premium corner lot, this expansive 7-bedroom, 4-bath home offers over-the-top living spaces designed for entertaining, multi-generational living, and creating unforgettable memories. Step inside to soaring ceilings, abundant natural light, and an open-concept floor plan that effortlessly blends elegance with everyday comfort. The chef-inspired kitchen serves as the heart of the home, featuring an oversized island, breakfast bar, abundant cabinetry, and seamless flow into the spacious family room and café dining area. The thoughtfully designed layout includes both the owner's suite and a guest bedroom on the main level, providing ideal accommodations for extended family or visitors. Upstairs, a sprawling game room, dedicated home theater, and additional bedrooms create the ultimate entertainment hub for family and guests alike. Out

Located in a quiet, gated community within a highly rated school zone, this well-maintained home offers comfort, privacy, and thoughtful upgrades. The home features two AC systems, including a main unit with an electronic air cleaner, a high-efficiency water heater, and a whole-house reverse osmosis and water softening system, along with updated double-pane windows on the back of the home. A new roof (2024) adds long-term peace of mind. Inside, you'll find 18.5-foot ceilings in the family room, plantation shutters, custom drapes, and ceiling fans, with wood flooring and travertine tile that complement each other throughout. The kitchen is finished with granite countertops, tile backsplash, a cherry wood bar top, and quality appliances. With a private backyard that is great for cookouts you can enjoy the gated living in a home ideally located near major highways, Central Florida attractions, and Downtown Winter Garden. Schedule your tour today!

Virtually Staged. One or more photos are virtually staged. Location. Luxury. Architectural character. Welcome to The Sanibel, affectionately known as “The Castle, ” an award-winning home just minutes from the charm and energy of Historic Downtown Winter Garden. This stunning residence blends timeless Italian-inspired architecture with modern comforts, creating a home that feels both elegant and inviting. From the moment you arrive, the home makes a memorable first impression with its arched wood double doors, custom soffit lighting, and classic concrete tile roof. Step inside and you’re greeted by soaring ceilings, detailed beams, and crown molding that add warmth and sophistication to the open-concept living spaces—perfect for both everyday living and entertaining. The gourmet kitchen is designed to impress, featuring premium KitchenAid appliances, a natural gas cooktop, built-in refrigerator, 42” custom cabinetry, a hidden walk-in pantry, and a reverse osmosis water system. Whether h

Step into a custom residence where calmness, grace, and thoughtful design greet you from the moment you arrive. In the quiet part of community, overlooking peaceful pond views, this luxury home features an open, airy floor plan filled with natural light, upscale laminate planks throughout, large lot. The gourmet kitchen is a true centerpiece here, offering a commercial-grade hood ideal for entertaining, gas stove, Bosch appliances, pot filler, walk-in pantry, and an appliance garage. The living area flows seamlessly to the outdoors through fully retractable sliding glass doors, complemented by surround sound and custom-tinted windows for comfort and privacy. With 4 bedrooms and 3 full baths—including one with direct patio access—the layout is designed for both convenience and flexibility. One bedroom is located on the main level, while upstairs you’ll find a Jack-and-Jill setup and a spacious primary suite featuring a tray ceiling, spotlight accents, and a spa-inspired bath with walk-i

Under Construction. Estimated Completion: September 2026. This beautiful Iris townhome is ideally situated on a peaceful pond-view homesite in the highly desirable Magnolia Reserve community. This thoughtfully designed home blends modern style, functional space, and an exceptional location. The main level features soaring 9’4” ceilings and an open-concept layout filled with natural light and vinyl plank flooring throughout the first floor. The gourmet kitchen is a true showstopper, offering 42” white shaker cabinets, stainless steel appliances, a walk-in pantry, and abundant cabinet and quartz countertop space—perfect for both everyday living and entertaining. Triple sliding glass doors open to a private paver patio overlooking serene pond views, creating seamless indoor-outdoor living. Upstairs, a large loft provides flexible space ideal for a home office, media room, play area, or homework zone. The second level also features a walk-in laundry room for added convenience and two spaci

Beautifully updated home featuring an open-concept layout with soaring high ceilings and tile flooring throughout the main living areas. The bedrooms are upgraded with luxury vinyl flooring, while the spacious loft showcases elegant bamboo flooring. The gourmet kitchen is a true showpiece, equipped with premium Thermador appliances, including a built-in refrigerator, cooktop, hood, oven, and microwave. A massive cook’s island with abundant storage underneath makes this space perfect for cooking and entertaining. This home offers 5 bedrooms and 3 full bathrooms, including a stunning primary suite with a double shower head and a separate soaking tub, separate vanities. Step outside to a private outdoor patio ideal for relaxing, grilling, or enjoying Florida evenings with family and friends. Located in the highly desirable Cambridge Crossing community, this home is zoned for excellent schools, including Lake Whitney Elementary, SunRidge Middle School, and West Orange High School. The neig

Virtually Staged. Solar system will be paid off by the seller at closing, $65,000 value! Seller offering RATE BUY-DOWN so Buyer will enjoy lower monthly payments! Nestled on this beautifully remodeled and RECENTLY PAINTED home located on a premier OVERSIZED CORNER LOT within the guard-gated enclave of STONEYBROOK WEST, this stunning 5-bedroom, 3-bathroom residence offers the ultimate Winter Garden lifestyle. The home has been meticulously enhanced with MODERN UPDATES, ensuring a MOVE-IN-READY experience for today’s discerning buyer. Save on utility bills with the whole house solar system and electric car charger. Inside, the open-concept layout is anchored by a SPACIOUS KITCHEN featuring quartz countertops, a central island, and HIGH-END STAINLESS STEEL APPLIANCES, all flowing into a spacious family room warmed by a classic fireplace. High-volume ceilings—reaching 9.25 feet on the main floor and an impressive 10.50 feet in the massive upstairs bonus room—create an airy, grand atmospher

Experience a lifestyle defined by elegance, privacy, and exceptional design in this luxury residence within the gated community of Canopy Oaks in Winter Garden. Built by A. R. Bailey Homes, this sought-after Delray floor plan offers nearly every feature today's discerning buyer desires, blending sophisticated architecture with functional living spaces designed for entertaining, multigenerational living and everyday comfort. Within an intimate enclave of just 49 homesites, this residence enjoys a premier location, minutes from historic downtown Winter Garden, Winter Garden Village, top-rated schools, dining, shopping, recreation and major commuter routes. A striking exterior presentation sets the tone with a paver driveway, concrete tile roof, stone-accented elevation, wood-look garage doors and grand solid wood double-entry doors. Beyond the entry, thoughtfully designed interiors showcase expansive gathering spaces, architectural ceilings, elegant finishes and abundant natural light. T

Virtually Staged. Rare space, privacy, and lifestyle come together in this beautifully refreshed Winter Garden home on a stunning 1.1-acre lot with no rear neighbors. Designed for both everyday comfort and entertaining, this 4-bedroom, 3-bath residence features fresh interior paint, a newer roof, new range, recently installed water heater, and an updated screened-in pool and spa. The expansive screened porch creates a true indoor-outdoor living experience, with multiple access points from the home and a kitchen window that opens directly to the entertaining area. The flexible layout includes a full bath with convenient access for guests, pool use, or potential in-lawu002Fextended stay needs. Outside, enjoy rare acreage, privacy, and room to breathe, plus a large backyard storage building. The community offers private access to Lake Tilden, along with a boat ramp, tennis court, pavilion, and peaceful neighborhood setting. Just minutes from Winter Garden Village, Downtown Winter Garden,

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 loftu002Fflex 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 eas

Under contract-accepting backup offers. *This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment. *. Welcome to 14170 Jomatt Loop in Winter Garden, a beautifully maintained home in the sought after Cypress Reserve community. This residence offers spacious living with 4 bedrooms and 3 bathrooms and an open floorplan ideal for both everyday living and entertaining. The gourmet kitchen features generous counter space, modern finishes, a gas range and opens seamlessly to the main living areas. The living room is warm and inviting with a fireplace accented by shiplap and custom wooden shelving, while board and batten wainscoting flows through the entryway and main living spaces, adding timeless character. Three of the four bedrooms include built in closets, and the laundry room has been enhanced with upgraded cabinetry for added functionality and storage. Step outside to your pr

This townhome in Longleaf at Oakland features a bright, open layout with plank vinyl flooring, granite countertops, fans new carpet and recessed lighting. The main level offers seamless flow for everyday living and entertaining. Upstairs, three well-appointed bedrooms provide comfortable and functional space. A private courtyard-style patio adds an inviting outdoor area for relaxing or grilling. Community amenities include a pool and playground, with nearby nature trails for walking and biking. Convenient access to major highways, shopping, dining, and downtown Winter Garden makes this location highly desirable

Nestled just minutes northeast of Orlando, this beautiful home in Winter Garden offers unparalleled convenience and charm. Located near Advent Health and Rollins College, it provides easy access to Central Florida’s most popular attractions and amenities. Disney World is just a short 20-30 minute drive, making spontaneous weekend family outings a breeze. Universal Studios Orlando and other top theme parks are also nearby, offering endless entertainment options. Whether you're an adventure seeker or someone who enjoys a more laid-back lifestyle, this location offers the perfect balance of both. These beautifully designed model homes under construction in Winter Garden offer the perfect combination of style, comfort, and convenience. Ideally located near Advent Health and Rollins College, the community provides easy access to Central Florida’s top attractions and everyday amenities. Downtown Winter Garden is ideal for leisurely strolls, with its picturesque streets lined with boutique sh

Golf cart district motivated seller Beautiful single-story home is nestled in a serene cul-de-sac in the heart of downtown Winter Garden. It is just an 8-minute drive to downtown Winter Garden, 5 minutes away from Publix, 10 minutes to Walmart, 14 minutes to target in winter garden village, easy access to SR-429 and Florida turnpike, offering exceptional convenience. This cozy 3-bedroom, 2-bathroom and an office can be an easy 4th bedroom. Modern single-story home provides 2,035 square feet of comfort and style. Fully renovated in 2022, featuring no carpeting throughout with dual offices, the kitchen has been updated with refinished cabinets and stainless steel appliances. Additionally, the roof and air conditioning were replaced in 2020, making it an ideal choice for buyers seeking a quick-move-in home!

PRICE ADJUSTED to reflect recent appraisal, this rare parcel presents immediate value. With vacant land ready for expansion or additional income potential with future development. Discover an exceptional property in the heart of highly desirable GOLF CART DISTRICT of Winter Garden. Situated on an expansive parcel totaling 3/4 of an acre, this unique estate offers unmatched space, charm and potential with NO HOA. All within short distance to the 22 mile long West Orange Trail, Winter Garden Farms Market, Plant Street dining, shopping and breathtaking sunsets over Lake Apopka. This beautifully maintained three-bedroom, two-bath home features an office with custom wood built-ins and a light-filled breezeway framed in windows, perfect for a sunroom or additional living space. Gorgeous hardwood floors flow throughout, and the newly renovated bathroom showcases modern, floor-to-ceiling tile for a luxurious touch. Storage is abundant, including an oversized two-car garage with a half bath, id

Virtually Staged. Welcome to this beautiful and spacious 4-bedroom, 2-bath home located in the desirable Fullers Crossing Community in charming Winter Garden. This well-maintained residence has over 2,500 square feet of comfortable living space, perfect for families and those who love to entertain. Step inside to discover a bright open floor plan featuring generous living and dining areas, a large kitchen with plenty of cabinet space, and a welcoming family room that flows seamlessly for everyday living. Conveniently located just minutes from shopping, dining, major highways, and the historic downtown district of Winter Garden, known for its popular farmers market, scenic trails and vibrant community events. You couldn't miss this incredible opportunity to own a beautiful home in one of the Central Florida's most sought-after areas. Contact agent to request your showing today! Some photos have been virtually staged

Immaculate FULLY FURNISHED three bedroom, two bath home plus an additional dedicated office, located on a premium pond-front corner lot in Longleaf at Oakland. This single. Level residence showcases extensive upgrades throughout. Features include luxury vinyl plank flooring, plantation shutters, custom feature wall with electric fireplace, built in cabinetry in the office and laundry room, upgraded kitchen cabinets, built in oven and cooktop, and upgraded refrigerator. Other highlights include trey ceilings with crown molding, fans in every room inside and out, Walk in showers, tiled to the ceiling, custom closet in the Primary, and the HVAC system is equipped with dual UV air purification lights. Exterior standouts include full hardy board siding (no stucco), beautiful curb appeal with professional concrete landscaping edging, and the garage is extended to 24 feet deep w/premium epoxy flooring. Move-in ready and truly turnkey—this home shows like a model! Location is prime with just 3

Located in the gated community of Oxford Chase, this beautifully designed 4-bedroom, 3-bath home offers a desirable split floor plan and a spacious 3-car garage. A welcoming front porch sets the tone for this inviting residence. The living room overlooks the private backyard and sparkling swimming pool, creating the perfect setting for relaxing or entertaining. The kitchen features white cabinetry, stainless steel appliances, a center island with a sit-in bar, and a separate dining area ideal for gatherings. There is also a versatile space perfect for a home office. The primary suite includes a sitting area and is adjacent to a well-appointed primary bathroom with dual sinks, a garden tub, and a walk-in shower. Step outside to the patio protected by a motorized screen, which opens directly to the pool area—perfect for enjoying Florida living year-round. Conveniently located just minutes from historic Downtown Winter Garden, Winter Garden Village at Fowler’s Grove, and Hamlin, you’ll en