Explore Homes for Sale in Winter Garden, FL
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Discover Your Dream Home: Explore Winter Garden, FL Homes For Sale with The Nest Group

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Winter Garden, FL, offers a vibrant real estate market with diverse homes for sale, perfect for every lifestyle. From charming historic bungalows in the downtown area to modern family residences in master-planned communities like Hamlin and Horizon West, prospective buyers will discover unparalleled opportunities. The Nest Group specializes in helping you navigate the unique offerings of Winter Garden, ensuring you find a property that perfectly matches your dreams. Explore the latest listings, experience the welcoming community spirit, and imagine life amidst beautiful natural surroundings and convenient access to Central Florida's best attractions. Your ideal Winter Garden home awaits.

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Winter Garden, FL Communities

Exploring Winter Garden's Diverse Real Estate Landscape

A Spectrum of Homes for Sale in Winter Garden, FL

Winter Garden, Florida, consistently ranks as one of Central Florida's most sought-after locations for new residents. Consequently, the inventory of homes for sale here is remarkably varied, appealing to a wide array of preferences and budgets. Whether you're seeking a quaint starter home or an expansive luxury estate, the Winter Garden real estate market presents a compelling selection.

Historic Charm Meets Modern Living: Downtown Winter Garden Homes

For those enchanted by character and community, downtown Winter Garden homes offer a unique appeal. Nestled around the iconic Plant Street, you'll find beautifully preserved and meticulously renovated bungalows and historic properties for sale. These residences provide direct access to the vibrant Plant Street Market, local eateries, boutiques, and the scenic West Orange Trail, embodying a truly walkable lifestyle.

New Construction Homes in Horizon West & Beyond

On the flip side, the sprawling Horizon West area, a significant part of Winter Garden, is a hub for new construction homes. Neighborhoods like Hamlin, Lakeside Village, Summerport, Independence, and Storey Grove feature an abundance of newly built homes for sale, often within master-planned communities. These areas are renowned for their state-of-the-art amenities, top-rated schools, and family-friendly environments, offering modern designs and energy-efficient features perfect for contemporary living.

Lifestyle & Community: What Makes Winter Garden Homes So Desirable?

Embrace the Winter Garden Lifestyle

Beyond the impressive selection of homes for sale, Winter Garden boasts a lifestyle that truly sets it apart. Residents enjoy a harmonious blend of small-town charm and big-city conveniences. Weekends can be spent cycling the West Orange Trail, exploring the Farmers Market, or enjoying live music and events on Plant Street. The close-knit community actively participates in local festivals and gatherings, fostering a genuine sense of belonging.

Family-Friendly Amenities and Top-Rated Schools

Families consistently choose Winter Garden for its exceptional quality of life. The community is home to numerous parks, recreational facilities, and highly-rated public and private schools, making it an ideal place to raise children. When considering homes for sale, the proximity to these essential family amenities often plays a crucial role in the decision-making process for many prospective buyers.

Finding Your Perfect Match: Types of Homes for Sale in Winter Garden

Single-Family Homes: Space and Serenity

The majority of homes for sale in Winter Garden are single-family residences, offering diverse architectural styles and lot sizes. From spacious suburban homes with private yards to elegant properties in gated communities like Oakland Park, there's a single-family home to suit every family's needs, providing ample space for growth and personalization.

Townhomes & Villas: Convenient Winter Garden Living

For those seeking a lower-maintenance lifestyle without compromising on location or amenities, Winter Garden also offers an excellent selection of townhomes and villas for sale. These properties are often found in communities with shared amenities like pools and clubhouses, presenting an attractive option for first-time buyers, downsizers, or those seeking a convenient lock-and-leave lifestyle near all local conveniences.

Luxury & Waterfront Homes for Sale in Winter Garden

Winter Garden's real estate market also caters to the luxury segment, featuring exquisite estates and waterfront homes for sale. Properties overlooking Lake Apopka or situated in exclusive enclaves offer premium finishes, expansive living spaces, and often private docks or stunning natural views. These luxury homes represent the pinnacle of Winter Garden living, combining elegance with a coveted Central Florida address.

Navigating the Winter Garden Real Estate Market

The Nest Group: Your Local Winter Garden Real Estate Experts

Successfully navigating the dynamic Winter Garden real estate market requires local expertise and insight. As your dedicated real estate partners, The Nest Group brings unparalleled knowledge of Winter Garden's neighborhoods, market trends, and hidden gems. We are committed to helping you discover the ideal homes for sale that align with your vision and lifestyle in this beautiful Central Florida community.

Newest Homes for Sale in Winter Garden, FL

$595,000
4 Beds ⋅ 3 Baths ⋅ Regency Oaks F SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. SEVERAL PHOTOS HAVE BEEN VIRTUALLY STAGED !Welcome to this beautifully updated 4-bedroom, 2.5-bath home in the highly sought-after Regency Oaks community. Thoughtfully upgraded for long-term peace of mind, this residence features a newly replaced roof, a 2023 HVAC system (both indoor and outdoor units), and a 2023 water heater—major improvements that add exceptional value and confidence for the next owner. Step inside to discover a bright, open floor plan with luxury vinyl flooring throughout, offering durability, modern style, and easy maintenance. The remodeled kitchen showcases sleek modern cabinetry and quartz countertops, creating a fresh, contemporary space perfect for everyday living and entertaining. The spacious primary suite provides a comfortable retreat, complemented by three additional bedrooms ideal for family, guests, or a home office. With two full bathrooms and a convenient half bath, the layout is designed for both functionality and comfort. Enjoy Florida living at its best with a screen-enclosed patio and a fully paved backyard, offering a low-maintenance outdoor oasis perfect for gatherings, grilling, or quiet relaxation. Located just 15 minutes from Universal Studios and Disney Parks and less than a 2-minute walk to AdventHealth, this home is perfectly positioned for both families and professionals. Regency Oaks offers resort-style amenities including a sparkling pool, clubhouse, tennis courts, playground, and a scenic park—enhancing the lifestyle experience beyond your front door. This move-in-ready home combines modern upgrades, unbeatable convenience, and exceptional community features—an outstanding opportunity to enjoy the best of Winter Garden and Orlando living.

13212 Social Lane, Winter Garden
$425,000
3 Beds ⋅ 2 Baths ⋅ Stone Crk SubDv. ⋅ 34787 Zip Code
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.

15187 Harrowgate Way, Winter Garden
$250,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
Welcome to resort-style living at its absolute finest. This Superior View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior views, the most updated and designer-curated décor in the entire property, and access to an unparalleled collection of amenities, this is more than a home — it's a five-star experience every single day. When you're not enjoying it yourself, let your investment work for you. This property sits within a prestigious hotel-managed rental program, meaning a professional, on-site operator handles everything — from bookings and guest services to housekeeping and maintenance. Completely hands-off ownership with income flowing in while the resort does all the heavy lifting. Owners enjoy access to resort amenities including pools, restaurants, spa, fitness facilities, and more — all maintained to the highest hospitality standards. Whether you're seeking a personal escape, a vacation retreat, or a smart investment vehicle, this unit checks every box. Newest tower. Most updated finishes. Superior views. World-class amenities. Professionally managed income potential. Financials available. Opportunities like this are rare — and they don't stay on the market long.

14501 Grove Resort Avenue Unit 2423, Winter Garden
$999,900
5 Beds ⋅ 4 Baths ⋅ Sunset Lakes SubDv. ⋅ 34787 Zip Code
Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including the Primary Bedroom), with the 5th Bedroom, a full bath and a bonus loft located on the second level. Inside, the home features designer ENGINEERED HARDWOOD FLOORING throughout the main living areas and the downstairs primary suite. The CHEF'S KITCHEN is a showpiece, boasting THREE SLABS OF PERMIUM CALCUTTA QUARTZ, an ITALIAN MARBLE BACKSPLASH, 60-inch DOUBLE-STACKED ALL WOOD SHAKER CABINTRY, a handy FOOD PREP ISLAND, a BREAKFAST BAR and TOP-OF-THE-LINE SAMSUNG APPLIANCES! The family room features AUTOMATIC ROLLER SHADES and is open to the kitchen and features Cathedral ceilings, a huge picture window and French Doors to the inviting lanai and sparkling pool. The primary suite is a retreat of its own, offering a FULLY-RENOVATED, SPA-INSPIRED bathroom with floor to ceiling CALCUTTA TILE, a frameless glass shower, a freestanding soaking tub, tall custom cabinetry with WHITE EXOTIC CARERRA QUARTZ COUNTERS and a massive walk-in closet! Architectural details elevate every room, including Plantation Shutters, multiple sets of French Doors, tray ceilings, volume and cathedral ceilings, extensive crown molding, transom windows, recessed lighting, bead boarding and elegant custom millwork. Step outside to a stunning outdoor oasis. The completely remodeled pool and spa area is surrounded by 2100 sq. ft. of travertine decking that extends across the covered lanai and additional outside patio space—perfect for entertaining! The lanai ceiling is finished with tongue and groove wood planks, adding warmth and sophistication. Other major upgrades include NEW DOUBLE-PANE, THERMAL WINDOWS (2023), a 2019 ROOF a 2019 AC SYSTEM and rain gutters. The extended brick paver driveway and matching walkway enhance curb appeal, while the well-fed irrigation system coupled with the well water (filtered by the whole house WATER SOFTENER) help keep utility costs low. Note: The wooden planter at the back of the pool and the retaining wall at the back of the lot needs some work and conveys 'AS IS.' All of this is just 5 minutes from the 429, offering quick access to Orlando and surrounding areas. Downtown Winter Garden & Winter Garden Village are also nearby as well as numerous championship golf courses for all your shopping, dining and recreational needs! Nearby top-rated schools are just another plus! Call for your showing today if you want to be the lucky one to snag this one-of-a-kind home before someone else does!

13536 Sunset Lakes Circle, Winter Garden
$614,000
4 Beds ⋅ 2 Baths ⋅ Summerlake Grvs SubDv. ⋅ 34787 Zip Code
Welcome to this exquisitely appointed residence, gracefully positioned on a private corner lot with no neighboring home on one side, offering a rare sense of seclusion and tranquility. The outdoor living space is thoughtfully designed, featuring an inviting patio ideal for refined entertaining or quiet relaxation. A freshly painted exterior (2024) enhances the home’s sophisticated curb appeal. Inside, the bespoke kitchen is a true centerpiece, showcasing custom finishes, under-cabinet lighting, a sleek glass tile backsplash, and a suite of recently upgraded appliances including a new dryer, dishwasher, disposal, and range. The formal living room is bathed in natural light from expansive windows and offers exceptional versatility, perfect as an elegant home office or curated hobby space. This residence effortlessly blends timeless style with modern convenience. Residents of Summerlake enjoy access to an array of resort-caliber amenities, including a clubhouse, pool, tennis courts, playground, parks, and scenic walking trails. Ideally situated near top-rated schools, upscale shopping, fine dining, major thoroughfares, and Orlando’s premier attractions, this exceptional home presents a rare opportunity to experience elevated living at its finest.

8031 Navel Orange Lane, Winter Garden
$579,900
4 Beds ⋅ 3 Baths ⋅ Johns Lake Pointe A & S SubDv. ⋅ 34787 Zip Code
Back on Market due to buyer unable to secure funding. Their loss, your opportunity. Location! Location! Located just 10 minutes from historic downtown Winter Garden and adjacent to the John Lake Conservation Area, you'll also enjoy easy walking and biking access to Tucker Ranch, the future site of a holistic wellness center, teaching farm, playground and family activity hub. Welcome to your move-in ready haven in Winter Garden's highly desirable Johns Lake Pointe community! This expansive 2,626 sq. ft. home sits on a generous 0.25-acre corner lot. Enjoy the comfort of a newer A/C unit and handler installed in January 2025 and freshly painted interiors (2022) that create a crisp, modern ambiance. The spacious eat-in kitchen features a large island with seating for four, ample cabinetry, a custom pantry, and extensive counter space—perfect for gatherings or morning routines. The first floor features a flexible private bonus room that can easily serve as a home office, study, or a welcoming fifth bedroom for overnight guests. The primary suite includes a beautifully crafted walk-in closet, while the custom laundry room offers built-in cabinetry and a convenient hanging bar for added functionality. Just beyond the living space, the screened-in lanai invites you to relax and unwind. Situated on a prime corner lot, the property also boasts a generously sized yard with endless potential for outdoor enjoyment. The epoxy-coated two-car garage is both functional and stylish, freshly painted and equipped with motion-sensor lighting for your convenience. This Meritage home is solid construction with 6 panel doors throughout and spray foam insulation in the attic. Community amenities include a pool, clubhouse, fitness center, yoga studio, pickleball and tennis courts—everything you need for a vibrant, active lifestyle. With its thoughtful design, abundant amenities, and unbeatable location, this home offers the perfect blend of comfort, convenience, and community.

15058 Sawgrass Bluff Drive, Winter Garden
$1,100,000
5 Beds ⋅ 5 Baths ⋅ Lakeshore Preserve Ph 2 SubDv. ⋅ 34787 Zip Code
OVERSIZED CORNER LOT. 3- CAR GARAGE. NEW OUTDOOR GOURMET AREA. FIRST-FLOOR SUITE. HUGE LOFT. 5 BEDROOMS Welcome to this beautifully appointed home in the highly desirable Lakeshore community in Winter Garden, offering an exceptional combination of space, comfort, and location. Situated in a prime area close to top-rated schools, shopping, dining, and major roads, this residence is ideal for buyers seeking both convenience and an outstanding lifestyle. This spacious home features 5 bedrooms, 4 full bathrooms, and 1 half bath, with a highly functional and attractive floor plan. Upon entry, you are welcomed by a private first-floor suite, perfect for guests, in-laws, or a home office with added privacy. Upstairs, you will find the remaining bedrooms, including the generous primary suite, along with a huge loft that offers endless possibilities for a media room, playroom, second living area, or home workspace. The home also features a formal dining room, while the kitchen, breakfast area, and family room flow seamlessly together in an open-concept layout that is ideal for both everyday living and entertaining. Step outside to enjoy the brand-new outdoor gourmet area, creating the perfect setting for gatherings, weekend barbecues, and relaxed Florida living. Residents of Lakeshore enjoy access to excellent community amenities, including a well-appointed clubhouse, fitness center, and playground, all contributing to a vibrant and welcoming neighborhood atmosphere. This is a rare opportunity to own a spacious, well-located home in one of Winter Garden’s most attractive communities. The spacious backyard offers excellent potential for a future pool. Some images have been virtually enhanced to help illustrate the outdoor possibilities. Pool shown in renderings is not currently installed.

15161 Canoe Place, Winter Garden
$339,000
2 Beds ⋅ 2 Baths ⋅ East Garden Manor Add 03 SubDv. ⋅ 34787 Zip Code
Seller its offering $6,000 for buyers closing costs. Move in ready, completed renovated, property offers two bedrooms and 2 bathrooms, brand new bathrooms, brand new kitchen, new appliances, new windows, ceramic trough the house, new roof, new plumbing, close to major roads, schools, minutes to Winter Garden dawn town.

483 Pennsylvania Avenue, Winter Garden
$655,500
4 Beds ⋅ 3 Baths ⋅ Highland Ridge SubDv. ⋅ 34787 Zip Code
Stunning Corner Lot Home Welcome to this beautifully designed, home situated on a desirable corner lot in the sought-after Highland Ridge community in Winter Garden, FL. Built by Meritage Homes, this residence offers the perfect blend of modern style, comfort, and energy efficiency. The open-concept first floor features a spacious great room and dining area that flow seamlessly together, creating an ideal space for entertaining and everyday living. The gourmet kitchen is the heart of the home, complete with a large island overlooking the main living areas and patio—perfect for gatherings with family and friends. Upstairs, the private primary suite offers a relaxing retreat with an oversized walk-in closet, dual vanities, and a sleek walk-in shower. Thoughtfully designed throughout, the home showcases professionally curated finishes, including elegant granite or quartz countertops and stylish tile flooring. Additional highlights include a detached two-car garage, ample natural light, and smart, energy-efficient features designed to provide long-term savings, improved comfort, and healthier living. Located in a vibrant community with top-rated schools and convenient access to major employment centers, shopping, and dining, this home truly offers the best of modern Florida living. Furnishings may be negotiable, offering a convenient, move-in-ready opportunity for buyers.

14006 Frasier Street, Winter Garden
$299,000
34787 Zip Code
Developer alert! Secure this rare residential lot that has plans for the construction of FOUR (4) RESIDENTIAL UNITS. Incredible opportunity to secure a multi-family development site complete with fully drafted architectural plans for a 4-unit building. Skip months of initial design work and the associated architectural expenses because these plans are completed and ready for submission to the city for permitting. The property features a flat and clear lot located in a high-demand area with strong rental and resale potential. Ideal project for a builder or investor looking to streamline their timeline and maximize returns. Buyer to verify all utilities, zoning requirements, and city permitting processes. Sold as-is with plans included.

9th Street, Winter Garden
$249,500
3 Beds ⋅ 2 Baths ⋅ Grove Resort And Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Looking for a Vacation Home in Orlando, this unit is a rare find with the Best Views in the Resort! This stunning 7th-floor condo at The Grove Resort & Spa offers breathtaking water views and front-row unobstructed seats to Disney fireworks reflecting over the lake each night. This fully furnished, all-inclusive condo-hotel provides a truly hands-off investment opportunity with onsite property management and a full-service rental program. Located in Building 1, this luxury 3-bedroom, 2-bath unit is perfectly situated just steps from restaurants, pool and resort amenities. Features an open floor plan with modern furnishings and all necessary housewares. The spacious primary suite includes a king bed, while both guest bedrooms have queen beds for comfortable guest accommodations. The fully equipped kitchen features stainless steel appliances, including refrigerator, range, microwave, and dishwasher. A private laundry closet with washer and dryer adds convenience for guests. Owners and guests alike will enjoy relaxing on the private screened balcony overlooking the water.The Grove Resort has exceptional amenities including multiple resort pools, Surfari Surf Park, Lake Austin with fishing dock and paddleboats, Escape Spa, fitness center, on-site restaurants, sundry shop, arcade, and youth activity center. Ideally located just minutes from Walt Disney

14501 Grove Resort Avenue Unit 1721, Winter Garden
$584,000
4 Beds ⋅ 3 Baths ⋅ Westhaven At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Toll Brothers New Construction at Winter Garden Horizon West. Estimate completion end of 2026. Single family Bungalow. The Montpelier home features a covered entry that leads to a spacious foyer and an expansive guest suite. The living area includes a dining room, with breakfast bar, great room, and access to the courtyard. The second-floor features 2 bedrooms and a primary suite is highlighted by a large walk-in closet and a private bath with dual vanities, separate shower, and private water closet. There's still time to personalize this home with your preferred design upgrades.

13014 Sunset Garden Lane, Winter Garden
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