Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida, a captivating city nestled in the heart of Orange County. Just a stone’s throw from the bustling attractions of Orlando, Winter Garden offers a delightful blend of small-town charm and modern conveniences, making it an ideal place to call home.

Known for its picturesque landscapes and vibrant downtown area, Winter Garden boasts a rich history that dates back to the 19th century. Strolling through the historic district, you'll find beautifully preserved buildings that house a variety of boutique shops, cozy cafes, and local restaurants that serve up delicious cuisine. The famed Plant Street Market is a must-visit, featuring an array of artisanal vendors and a lively atmosphere perfect for family outings or a casual weekend stroll.

Outdoor enthusiasts will fall in love with Winter Garden’s abundant parks and recreational opportunities. The West Orange Trail, a scenic 22-mile long pathway, invites residents to enjoy walking, biking, and jogging amidst lush greenery. For those who appreciate nature, the nearby Lake Apopka offers stunning views and diverse wildlife, perfect for birdwatching or a peaceful afternoon by the water.

Families will appreciate the excellent schools and community spirit that Winter Garden fosters. With numerous events throughout the year, including farmers' markets and holiday celebrations, there’s always something happening to bring the community together.

Whether you’re seeking a serene suburban lifestyle or a vibrant community with plenty of activities, Winter Garden is a hidden gem that promises to enchant and inspire. Come explore this charming city and discover your perfect place to call home!

Newest Listings in Winter Garden

3 Beds ⋅ 2 Baths ⋅ Summerlake Pd Phase 2a And 2b SubDv. ⋅ 34787 Zip Code

This charming one-story single-family home offers the perfect blend of comfort, functionality, and an exceptional location in one of Winter Garden’s most desirable areas. Ideally located JUST MINUTES FROM THE VIBRANT HAMLIN TOWN CENTER, this beautifully maintained home is conveniently close to shopping, dining, entertainment, top-rated schools, and major highways. Featuring 3 spacious bedrooms and 2 full bathrooms, this home offers a comfortable and functional layout designed for easy everyday living. As you enter, you are welcomed by an inviting open-concept living area that seamlessly connects the living room, dining space, and kitchen. Large windows fill the home with natural light, creating a bright and welcoming atmosphere. The kitchen offers ample cabinet space, modern appliances, and a convenient breakfast bar, making it ideal for both everyday meals and entertaining. The DISHWASHER AND MICROWAVE ARE NEW, adding convenience and value to this well-appointed kitchen. The spacious primary suite provides a peaceful retreat with a generous walk-in closet and a private bathroom featuring dual sinks, a soaking tub, and a separate shower. The additional bedrooms are well-sized and share a full bathroom. ROOF REPLACED IN 2026! INTERIOR/EXTERIOR PAINT COMPLETED IN 2026! These recent updates add significant value and peace of mind for the new owner. The entire home features TILE FLOORING THROUGHOUT, offering durability, easy maintenance, and a clean, cohesive look. The home is also located JUST ONE BLOCK FROM THE COMMUNITY CLUBHOUSE, providing exceptionally convenient access to the neighborhood amenities. The attached garage features a SPLIT A/C UNIT, providing added comfort and flexibility for the space. It can be enjoyed as a convenient additional area for hobbies, recreation, storage, or other personal needs. The covered lanai also features SCREEN ENCLOSURE, creating a comfortable outdoor space to relax and enjoy the Florida lifestyle. The location adds even more value. Enjoy being just minutes from Hamlin Town Center, with convenient access to Summerlake Elementary, Hamlin Middle School, and Horizon High School, as well as Publix, Walmart, restaurants, cafés, boutique shopping, Cinépolis Luxury Cinemas, PopStroke, Urban Air Adventure Park, and SR-429. As a resident of the highly desirable Summerlake community, you will enjoy an impressive selection of amenities, including a clubhouse, fitness center, community pool, tennis courts, playgrounds, walking trails, and lawn maintenance included through the HOA. Move-in ready and thoughtfully maintained, this home combines desirable upgrades, low-maintenance living, and a PRIME WINTER GARDEN LOCATION. With a new roof and fresh interior and exterior paint completed in 2026, new kitchen appliances, tile flooring throughout, a screened lanai, and the clubhouse just one block away, this home is an excellent opportunity to enjoy everything Winter Garden has to enjoy. Schedule your private showing today!

14931 Porter Rd, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 2c 2d 2e SubDv. ⋅ 34787 Zip Code

LAKEFRONT LUXURY IN SUMMERLAKE! Stunning 4BR/3BA townhome with bonus room, open concept living, brand new roof, state of the art appliances & decorative lighting included! Enjoy breathtaking lake views, nightly Disney fireworks, and a private fenced brick paver courtyard perfect for morning coffee or relaxing. Spacious 2-car garage. Resort-style amenities include clubhouse, gym, pool, soccer field, walking trails & fishing dock. Minutes to Disney, Downtown Winter Garden & endless dining! A MUST-SEE! Buyer to verify room sizes and all measurements. Public records reflect 3BR/2BA; actual configuration is 4BR/3BA plus bonus room

8174 Bluejack Oak Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code

BACK ON THE MARKET WITH A PRICE IMPROVEMENT! Don’t miss this highly upgraded Toll Brothers townhome in Westhaven at Ovation. Built in 2024, this popular floor plan that is NO LONGER AVAILABLE FROM THE BUILDER. The open-concept main level features a beautifully upgraded kitchen with quartz countertops, designer cabinetry and backsplash, stainless steel appliances, and an oversized island. Step outside to your private courtyard featuring a hot tub that can come along—perfect for relaxing and enjoying the Florida lifestyle. Additional upgrades include upgraded finishes throughout. Upstairs, the spacious primary suite offers a walk-in closet and upgraded en-suite bath, plus two additional bedrooms. Located approximately 2 MINUTES FROM THE NEARBY ELEMENTARY SCHOOL and close to Horizon West, Hamlin, shopping, dining, entertainment, and major roadways. Multiple upgrades, included spa, prime Winter Garden location, and a floor plan you can no longer purchase from the builder!

13953 Easdale Alley, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Tuscany SubDv. ⋅ 34787 Zip Code

**GOLF CART COMMUNITY** Welcome to this charming home located at 1631 Charlemagne Ct in Winter Garden, FL. This beautiful house features three spacious bedrooms, a dedicated office, 2 full bathrooms, living room, dining room (currently using as a second office) laundry room and a two car garage, providing ample space for comfortable living. A beautifully maintained and thoughtfully upgraded home tucked away on a quiet cul-de-sac in one of Winter Garden's most desirable residential neighborhoods. Sitting on a large, fully fenced lot, this property delivers privacy, peace, and timeless appeal, with mature Oak trees providing lots of shade for outdoor entertaining. With a generous living area of 2,035 square feet, this home accords an inviting layout appropriate for relaxation and entertaining. Step inside and you're immediately greeted by cathedral ceilings in the living room and kitchen, creating an open, airy atmosphere filled with natural light. Tile flooring throughout the entire home adds a clean, cohesive look while offering durability and easy maintenance. The chef-inspired kitchen is the heart of the home, showcasing upgraded custom cabinetry, and granite countertops. The kitchen features abundant cabinet space and a large pantry offering exceptionally storage for all your kitchen essentials. Included are Bosch appliances and a charming nook overlooking the beautiful mature landscaping. The primary bedroom suite is a truly spacious sanctuary, complete with elegant plantation shutters, a Jacuzzi tub, dual sinks and his-and-her walk-in closets. Two additional bedrooms and a full bath provide comfort and flexibility for family or guests. The laundry room has built-in cabinetry, countertop and additional overhead shelf for added storage. A hall linen closet has extra-large storage providing plenty of space for additional household essentials. Major upgrades bring peace of mind and value including a new roof (2021), exterior freshly painted (2021), Brand-new AC (2024), Newly planted sod in back yard (2026) and upgraded Irrigation Control Panel (2026). Hop on your golf cart just minutes to historic downtown Winter Garden and enjoy your favorite restaurants, events and farmers market. Or take a relaxing nature walk or bike ride on the West Orange trial. This home is move in ready!

1631 Charlemagne Court, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Ph 3 SubDv. ⋅ 34787 Zip Code

Experience refined Florida living in this beautifully appointed 2024-built residence, ideally situated within the gated community of Del Webb Oasis. Thoughtfully designed with 2 bedrooms plus a versatile bonus room—perfect as a 3rd bedroom, private home office, den, or sitting room—the home offers a desirable split-bedroom floor plan that provides both privacy and comfort. upgrades are showcased throughout, including luxury vinyl flooring, recessed lighting, and contemporary finishes. At the heart of the home, the stylish kitchen features Tier 3 upgraded finishes complemented by Whirlpool appliances, creating an inviting space that seamlessly blends modern design with everyday functionality. Step outside to the screened-in lanai, an ideal setting for peaceful morning coffee, outdoor dining, or relaxing Florida evenings. The 2-car garage is equally well appointed with sleek epoxy flooring and an EV charger for added convenience. Beyond the home, Del Webb Oasis offers a gated, amenity-rich lifestyle designed for recreation, relaxation, and connection. Association fees include cable and internet, while the community provides an exceptional setting to stay active, socialize, and enjoy the best of Florida living. Adding to its appeal, the property is approximately 20 minutes from the Walt Disney World Resort area, depending on traffic—placing world-class dining, shopping, entertainment, and recreation within easy reach. Built in 2024 and beautifully upgraded throughout, this exceptional residence delivers the perfect combination of modern luxury, low-maintenance living, and resort-style convenience.

13418 Princess Street, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Orchard Pk/Stillwater Xing Ph SubDv. ⋅ 34787 Zip Code

WELCOME TO 3019 CHERRY ORCHARD LANE, A BEAUTIFULLY REMODELED HOME IN THE HEART OF WINTER GARDEN! This stunning residence has just undergone an impressive transformation, offering a fresh, modern, move-in-ready interior that truly stands out in the neighborhood. The home features NEW INTERIOR AND EXTERIOR PAINT (2026), a COMPLETELY RENOVATED KITCHEN, and BEAUTIFULLY UPDATED BATHROOMS, all thoughtfully redesigned with contemporary finishes and attention to detail. Custom-designed office with built-in cabinetry and a Murphy bed seamlessly integrated into the cabinetry. Every improvement was carefully selected to create a bright, stylish, and welcoming atmosphere throughout the home. This is a rare opportunity to own a beautifully renovated property offering a level of updates and finishes that is difficult to find in the surrounding area. Ideally located in desirable Winter Garden, with convenient access to shopping, dining, entertainment, parks, major roadways, and everything this highly sought-after area. MOVE-IN READY and beautifully refreshed from the inside out, schedule your private showing and come see what makes this home truly special!

3019 Cherry Orchard Lane, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

FULLY FURNISHED/TURNKEY LUXURIOUS 3/3 Corner Unit at The Grove Resort & Spa, Orlando Welcome to your dream oasis at The Grove Resort & Spa Orlando! This magnificent corner unit boasts the LARGEST floor plan available, featuring 3 spacious bedrooms and 3 elegant bathrooms. Experience the ultimate blend of comfort and luxury in this stunning condo-hotel located just six miles from Walt Disney World® Theme Parks, The Grove Resort & Spa offers unparalleled access to Orlando’s world-famous attractions. Enjoy daily transportation to Walt Disney World®, Universal Orlando, and SeaWorld, making it effortless to explore all that Orlando has to provide. Indulge in a variety of resort amenities designed for both relaxation and adventure. The Surfari Water Park features thrilling water slides, a lazy river, and the exhilarating FlowRider® Double surf simulator. Unwind at The Springs Pools, with three full-sized pools, an oversized hot tub, and poolside bar service. At Lake Austin, engage in catch-and-release fishing, paddle boating, or simply savor the serene views of the surrounding nature preserve. Stay active with a fully-equipped fitness center and scenic jogging paths. Families will love Flip Flop’s Family Fun Center, offering the latest arcade games and a glow-in-the-dark mini golf course. This corner unit is designed with a modern touch, offering a spacious open-plan living area, a gourmet kitchen, and stylish furnishings throughout. Each bedroom is a private retreat, complete with luxurious bedding and ample storage. Owning a unit at The Grove Resort & Spa offers not only a luxurious vacation spot but also a fantastic stress-free investment opportunity. Don’t miss the opportunity to own a piece of paradise at The Grove Resort & Spa, where every day feels like a vacation. Contact us today to schedule a private viewing and experience the exceptional lifestyle that awaits you.

14501 Grove Resort Avenue Unit 3201, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Orchard Hills Phase 2 SubDv. ⋅ 34787 Zip Code

Welcome to this bright and airy 4-bedroom, 2.5-bath home offering a comfortable and inviting layout. The spacious kitchen opens directly to the living room, creating a great flow for everyday living and entertaining, and features a large island with plenty of room for meal prep or gathering with family and friends. The open feel continues throughout the main living areas, with plenty of natural light adding to the welcoming atmosphere. The primary bedroom offers a private retreat with its own door leading to the balcony, providing a nice spot to step outside and enjoy the fresh air.

14354 Orchard Hills Boulevard, Winter Garden

4 Beds ⋅ 2 Baths ⋅ Stoneybrook West SubDv. ⋅ 34787 Zip Code

Welcome to the highly sought-after Brentwood model in the guard-gated golf community of Stoneybrook West! This 4-bedroom home offers a flexible floor plan with the option to use the fourth bedroom as a private home office, making it ideal for today’s lifestyle. The spacious kitchen opens to the family room, creating a comfortable gathering space highlighted by a cozy gas fireplace. Recent updates include a NEW HVAC system (2026), water heater (2023), roof (2018), new garbage disposal, gutters, and more. The primary suite features beautiful bay windows and a large walk-in closet. Enjoy Florida living year-round from the added covered and screened patio with tile flooring overlooking the fenced backyard. Additional highlights include attic storage with plywood flooring, providing valuable extra storage space. Located in the desirable Stoneybrook West community, residents enjoy an impressive array of amenities, including golf, clubhouse, pools, fitness facilities, tennis, pickleball, playgrounds, walking trails, and more. The community also offers lake access and boating for residents, including a private community boat launch. All of this is located in Winter Garden, one of Central Florida’s most sought-after and vibrant markets, offering convenient access to shopping, dining, entertainment, top-rated schools, major roadways, and everything the area has to offer. A flexible floor plan, important major-system updates, outdoor living space, and an exceptional guard-gated community make this Brentwood model a home worth seeing!

1118 Maidenmoor Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Harbor floor plan offers a smartly designed two-story townhome that caters to both convenience and space. With three bedrooms and two and a half bathrooms, this home ensures comfort on every level. All three bedrooms are located upstairs, providing privacy and quiet from the main living areas. The second floor also features a spacious primary suite with a walk-in closet and private bath, alongside two additional bedrooms. Downstairs, the open-concept layout connects the great room to the dining area, making it perfect for entertaining or family gatherings. The covered lanai offers a cozy outdoor retreat, ideal for relaxing at the end of the day. Completing the home is a detached two-car garage, ensuring ample parking and storage. The Harbor floor plan offers modern living tailored to meet everyday needs with style and functionality. Sample Image

17732 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Hamlin Meadows SubDv. ⋅ 34787 Zip Code

Virtually Staged. Under Construction. The Porter floorplan is an inviting two-story townhome designed with thoughtful spaces throughout. Featuring three bedrooms and two full bathrooms, the layout offers a smooth flow between living spaces. The first floor boasts a bright great room that opens into the dining area and lanai, perfect for entertaining or relaxation. Upstairs, all three bedrooms are thoughtfully arranged alongside a versatile loft, providing additional living space or an ideal work-from-home area. With a two-car garage and laundry room conveniently located on the second floor, the Porter combines functionality with comfort, making it a standout home choice. Sample Image!!

17728 Porter Road, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Storey Grove SubDv. ⋅ 34787 Zip Code

Virtually Staged. **Virtually Staged | Tenant Occupied | Great Investment Opportunity** Beautiful two-story home in the desirable Storey Grove community in Winter Garden, currently rented for the full year—ideal for investors seeking immediate rental income. This home offers 3 bedrooms, 2.5 bathrooms, approximately 1,717 sq. ft. of living space, peaceful pond views, and a detached two-car garage. The open-concept layout features a kitchen with island overlooking the family and dining areas. Upstairs, the primary suite includes an oversized bathroom and walk-in closet. Residents enjoy a clubhouse, fitness center, resort-style pool, hedge maze, and dog park. Conveniently located near SR-429, US-192, and SR-545, just minutes from Walt Disney World, Orange County National Golf Center, shopping, dining, and Walmart. A great opportunity in one of Winter Garden’s most sought-after communities.

11367 Great Rock Street, Winter Garden

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