Winter Garden Real Estate

Winter Garden Real Estate

Welcome to Winter Garden, Florida – a charming city nestled in the heart of Orange County that beautifully blends small-town charm with modern conveniences. Just a stone’s throw from the bustling city of Orlando, Winter Garden offers a serene escape while still providing easy access to urban amenities and attractions.

Known for its picturesque downtown area, Winter Garden boasts a vibrant Main Street lined with quaint shops, delightful cafes, and a rich array of dining options. The historic district, with its beautifully preserved buildings, invites residents and visitors alike to explore its unique character and charm. The city is also home to the West Orange Trail, a multi-use path that stretches over 22 miles, perfect for walking, jogging, or biking, and offers stunning views of the surrounding natural beauty.

For families, Winter Garden is an excellent place to call home, with top-rated schools and a strong sense of community. The city hosts numerous events throughout the year, including farmers' markets, art festivals, and seasonal celebrations, fostering a welcoming atmosphere for residents of all ages.

Nature enthusiasts will appreciate the nearby parks and recreational areas, including the beautiful Lake Apopka, where you can enjoy fishing, bird watching, and tranquil picnics. With its ideal location, rich history, and friendly community, Winter Garden is not just a place to live; it’s a place to thrive. Come discover the warmth and charm of Winter Garden, where your dream home awaits!

Newest Listings in Winter Garden

13160 Dendy Way, Winter Garden

13160 Dendy Way, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code

Welcome to this beautifully upgraded, nearly new, one-owner home featuring 3 bedrooms, 2.5 bathrooms, and a versatile FLEX ROOM that can serve as a 4th bedroom or home office! This move-in-ready residence showcases modern elegance and thoughtful upgrades throughout. The open-concept living area features an impressive 16-foot sliding glass door, bringing in abundant natural light. The stunning gourmet kitchen boasts quartz countertops with a waterfall-edge island, premium GE Café appliances, ceiling-height backsplash, and under-cabinet lighting. The spacious primary suite offers a spa-inspired bathroom with a freestanding soaking tub, quartz countertops, and a generous walk-in closet. Additional highlights include decorative feature walls, upgraded tile flooring, smart home features, window blinds, a whole-house water filtration system, and an EV charging outlet in the garage. Ideally located within walking distance of the new school Ovation Elementary School and just minutes from Disney, shopping, dining, and major highways. A perfect combination of luxury, comfort, and prime location. Schedule your private showing today!

13160 Dendy Way, Winter Garden

9901 Avalon Woods Drive, Winter Garden

9901 Avalon Woods Drive, Winter Garden

3 Beds ⋅ 2 Baths ⋅ 001 SubDv. ⋅ 34787 Zip Code

Auction Property. Discover the quieter side of Winter Garden. Set back from the roadway in an established rural setting, this property offers a sense of seclusion and a spacious, larger-lot environment. The surrounding area features acreage homes, wooded parcels, and open land, creating a distinctive country atmosphere. Enjoy the appeal of a peaceful setting with shopping, dining, and everyday conveniences available in the greater Winter Garden and Clermont areas. A unique auction opportunity for those seeking privacy and a location beyond the typical subdivision.

9901 Avalon Woods Drive, Winter Garden

6262 Argent Wood Drive, Winter Garden

6262 Argent Wood Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Silverleaf Oaks/Hamlin Ph 3a SubDv. ⋅ 34787 Zip Code

Virtually Staged. THIS IS IT! Skip the builder and SAVE TIME and MONEY buy this practically NEW "Scarlett" floorplan by Pulte. Seller picked a premium lot (NO REAR NEIGHBOR), selected a ton of upgrades in the design center AND then after they moved in... added a gorgeous outdoor kitchen, travertine paver deck, motorized screen and LED soffit lighting and then had to relocate so their loss is your gain. This incredible floorplan features dual primary suites (one upstairs and one downstairs) plus 3 additional bedrooms and a huge loft/den. The kitchen is features upgraded level 4 quartz, built-in stainless steel oven, microwave and cooktop, soft close cabinets and a huge walk in pantry. Tons of natural light and upgrades in every room. Close to Publix, Walmart, tons of restaurants and walking distance to Hamlin Elementary AND Hamlin Middle school. Check out the virtual 360 Walkthrough link.

6262 Argent Wood Drive, Winter Garden

728 Garden West Terrace, Winter Garden

728 Garden West Terrace, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Garden West SubDv. ⋅ 34787 Zip Code

Welcome to this stunning custom home crafted by the renowned Pioneer Builders in 2022, nestled in one of Winter Garden's most coveted locations. Just steps from the beloved West Orange Trail and the charming Golf Cart District of Historic Downtown Winter Garden, this home offers the best of the Winter Garden lifestyle right at your doorstep. Whether you're pedaling the trail at sunrise or cruising downtown in your golf cart for dinner and live music, this location makes it easy to enjoy everything this vibrant community has to offer. From the moment you step inside, the quality and craftsmanship are undeniable. Engineered hardwood floors flow seamlessly throughout the home, while custom cabinetry adds timeless elegance to every space. The open living areas feature top-of-the-line Fisher & Paykel appliances, blending elevated design with everyday functionality. Plantation shutters throughout the main house add a classic, refined touch, while an automatic gate provides an added layer of privacy and convenience. The main level features a private ensuite bedroom and full bath, ideal for guests or multigenerational living, along with a convenient powder bath for visitors. Upstairs, the primary suite serves as a true retreat, complete with two oversized walk-in closets and a luxurious ensuite bath. Two additional bedrooms share a well-appointed Jack-and-Jill bathroom, while an upstairs laundry room adds everyday convenience. Added in 2024, the private apartment above the garage is a rare and exceptional bonus, complete with a kitchenette, dedicated office space, full bath, and in-unit laundry. Whether envisioned as a private guest suite, in-law quarters, a dedicated work-from-home retreat, or an income-producing rental, the possibilities are endless. Winter Garden's Golf Cart District is more than a novelty—it's a way of life. Residents enjoy cruising to the award-winning Farmers Market, exploring boutique shops and local restaurants, visiting breweries, and taking part in the community events that make Historic Downtown Winter Garden one of Central Florida's most vibrant destinations. The West Orange Trail, spanning more than 22 miles of scenic, paved pathways, is a paradise for cyclists, joggers, and walkers. With this home's prime proximity, outdoor recreation is always within easy reach. This is more than a home—it's a lifestyle. Don't miss the opportunity to own a distinctive property offering timeless finishes, versatile living spaces, added privacy, and an exceptional location in one of Central Florida's most sought-after communities.

728 Garden West Terrace, Winter Garden

17138 Arrowhead Boulevard, Winter Garden

17138 Arrowhead Boulevard, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Arrowhead Lakes SubDv. ⋅ 34787 Zip Code

Prime location! Spring fed lakefront charm. Well-built and maintained 2 bedroom, 2 bath home high and dry. Nice layout inside out with private pond and lake access. Outdoor pet enclosure for your furry friends. The enclosed metal garage can protect all your toys. Mature landscaping. Established neighborhood. Tons of natural life with fishing opportunities. 11 minutes to Disney World. 14 minutes to Orange County National Golf Center and Lodge. A2zoning, A schools and No HOA.

17138 Arrowhead Boulevard, Winter Garden

3275 Buoy Circle, Winter Garden

3275 Buoy Circle, Winter Garden

5 Beds ⋅ 5 Baths ⋅ Lakeview Preserve SubDv. ⋅ 34787 Zip Code

Virtually Staged. SPACIOUS LUXURY LIVING + 5 BEDROOMS + 4.5 BATHROOMS + 2 FLEX SPACES + GATED COMMUNITY! Welcome to this stunning YORKSHIRE MODEL in the highly desirable LAKEVIEW PRESERVE community of Winter Garden! Designed with space, comfort, and versatility in mind, this beautifully appointed home offers an exceptional floor plan ideal for MULTIGENERATIONAL LIVING, WORKING FROM HOME, AND ENTERTAINING. Featuring 5 generously sized bedrooms, 4 full bathrooms, a half bath, TWO FLEX SPACES—ONE ON EACH LEVEL, and an oversized lot with an open green backyard, there's room for everyone to spread out and enjoy! From the moment you enter, you'll appreciate the thoughtfully designed layout, 8-foot interior doors, abundant natural light, and stylish designer finishes. The OPEN-CONCEPT FLOOR PLAN flows seamlessly from the spacious gathering room into the dining area and GOURMET KITCHEN, featuring QUARTZ COUNTERTOPS, 42-INCH SOFT-CLOSE CABINETRY, BUILT-IN APPLIANCES, a decorative wood canopy hood, designer tile backsplash, oversized center island, and walk-in pantry. Expansive POCKET SLIDING GLASS DOORS open to the impressive 22-FOOT COVERED LANAI, NOW SCREENED IN BY THE CURRENT OWNERS, creating the perfect setting for indoor-outdoor entertaining while overlooking the spacious backyard. One of this home's greatest advantages is its FLEXIBLE, MULTIGENERATIONAL-FRIENDLY FLOOR PLAN. The FIRST-FLOOR GUEST SUITE WITH PRIVATE EN-SUITE BATHROOM AND WALK-IN CLOSET provides an ideal retreat for extended family, overnight guests, or anyone seeking additional privacy. A versatile FIRST-FLOOR FLEX SPACE offers the perfect opportunity for a home office, playroom, or additional living area. Upstairs, a SECOND SPACIOUS FLEX SPACE provides even more possibilities for a media room, game room, study area, or separate gathering area, allowing everyone to enjoy their own space. The upstairs PRIMARY SUITE is a relaxing private retreat featuring a large walk-in closet and a beautifully appointed en-suite bathroom with DUAL QUARTZ-TOPPED VANITIES, AN OVERSIZED WALK-IN SHOWER, and a private water closet. Three additional upstairs bedrooms, including one with its own EN-SUITE BATHROOM, offer comfortable accommodations and generous closet space. The upgraded laundry room adds convenience with cabinetry, quartz countertops, and a utility sink. Additional highlights include PORCELAIN TILE FLOORING throughout the main first-floor living areas, designer bathroom finishes, ample storage throughout, outdoor kitchen pre-plumbing, and a 2-CAR GARAGE WITH NEWLY ADDED EPOXY FLOORING for a clean, finished look. Located within the sought-after GATED COMMUNITY OF LAKEVIEW PRESERVE, residents enjoy RESORT-STYLE AMENITIES, including a sparkling pool with splash pad, clubhouse, fitness center, playground, picnic areas, and KAYAK LAUNCH WITH ACCESS TO JOHNS LAKE. Even better, the community has NO CDD FEE! Just approximately 5 miles from charming DOWNTOWN WINTER GARDEN and minutes from SR 429, you'll enjoy convenient access to shopping, dining, entertainment, and major Central Florida roadways. Experience the space, flexibility, and lifestyle this exceptional Winter Garden home has to offer. Schedule your private showing today!

3275 Buoy Circle, Winter Garden

2199 White Feather Loop, Oakland

2199 White Feather Loop, Oakland

3 Beds ⋅ 3 Baths ⋅ Oakland Trails Ph 1 SubDv. ⋅ 34787 Zip Code

Stunning 3-bedroom, 2.5-bath bungalow nestled in the highly desirable community of Oakland, offering picturesque views of the community park, lush green spaces, and direct access to local walking trails. Built in 2018 and impeccably maintained, this home features an open-concept layout with towering 10-foot ceilings throughout. The main level boasts gorgeous tile flooring, a built-in office desk, a convenient wet bar, and carefully curated interior lighting that enhances the home's warm character and sophisticated ambiance. The gourmet kitchen shines with 42-inch refinished maple cabinets, updated hardware, quartz countertops, a stunning center quartz island, and a striking ceiling-height marble backsplash. Upstairs, enjoy the warmth of bamboo stairs and beautiful bamboo flooring across all bedrooms, each equipped with walk-in closets. Additional notable upgrades include quartz countertops in all bathrooms, beautiful zebra blinds, a 2026 refrigerator, and an epoxy-finished two-car garage. Step outside to exceptional exterior enhancements added in 2025 and 2026, including striking exterior accent lighting that delivers incredible nighttime curb appeal and presence, a fully sealed paver driveway, a welcoming front porch with ceiling fans, and an extended paver pathway wrapping around the house. Practical features include a brand-new gutter system connected to a downpour drainage system, plus a reliable irrigation system. Located in a top-rated school district, this home places you moments away from the scenic Oakland Nature Preserve, community parks like Speer Park, vibrant local farmers markets, rich cultural attractions like the historic Garden Theatre, and nearby dining favorites. Don't miss this incredible gem!

2199 White Feather Loop, Oakland

618 Sigler Drive, Winter Garden

618 Sigler Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Bayview floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

618 Sigler Drive, Winter Garden

15725 Signature Drive, Winter Garden

15725 Signature Drive, Winter Garden

6 Beds ⋅ 3 Baths ⋅ Signature Lakes Ph 02 A B H I J SubDv. ⋅ 34787 Zip Code

MOVE-IN READY & EASY TO SHOW! Nestled in the highly sought-after Independence community of Winter Garden, this beautifully maintained Lennar “Rio” floor plan offers the perfect combination of location, lifestyle, and resort-style amenities. This spacious two-story home features 6 bedrooms, 3 full baths, a versatile loft, and 2,714 sq. ft. of living space, all situated on a desirable corner lot. Freshly painted, vacant, and in impeccable condition, this home is ready for its next owner. The thoughtfully designed layout offers generous living spaces, a spacious kitchen with solid wood cabinetry and granite countertops, stainless steel appliances, an interior laundry room, smart thermostat, security cameras, and a private side - backyard. Additional improvements include a newer A/C system, insulated garage, and garage door opener. A covered and screened outdoor area provides additional space to relax and enjoy the Florida lifestyle. Independence is one of Horizon West’s desirable master-planned communities, offering an exceptional array of amenities including clubhouses, resort-style community pools, fitness facilities, tennis courts, playgrounds, parks, sidewalks, and private community boat ramps with lake access. Ideally located near shopping, dining, entertainment, schools, and everyday conveniences, with easy access to SR-429 and Central Florida’s world-famous attractions. Enjoy convenient access to the growing Horizon West area, Winter Garden destinations, restaurants, cinemas, Publix, Walmart, and Walt Disney World Resort. Immaculate, spacious, vacant, and truly move-in ready, this is an exceptional opportunity to enjoy the Independence lifestyle in one of Winter Garden’s most desirable locations. Schedule your private showing today!

15725 Signature Drive, Winter Garden

1444 Kenny Court, Winter Garden

1444 Kenny Court, Winter Garden

3 Beds ⋅ 2 Baths ⋅ Kenny Court SubDv. ⋅ 34787 Zip Code

Welcome to this inviting 3-Bedroom, 2-Bath single-story home in a DESIRABLE LOCATION near Winter Garden, offering a spacious CORNER LOT, NO HOA and plenty of room to make the most of Florida living! Set on NEARLY A QUARTER ACRE, the property features MATURE SHADE TREES, a large driveway with ample parking and a welcoming setting. Inside, BEAUTIFUL LVP FLOORING and NEW LEVELOR BLINDS throughout, create a fresh, cohesive look, while NEW AC (2026) and a ROOF REPLACED IN 2022 add peace of mind. The OPEN FLOOR PLAN allows the Living Room, Dining Room and Kitchen to flow together seamlessly, creating a comfortable setting, while NATURAL LIGHT fills the space, enhancing the bright and airy feel. The Kitchen offers plenty of SOLID WOOD WHITE CABINETRY, solid-surface countertops and a center island with breakfast bar seating. A RECENTLY UPDATED TILE BACKSPLASH adds a stylish finishing touch, while STAINLESS STEEL APPLIANCES—including a GAS STOVE—make meal preparation a pleasure. A window above the sink brings in NATURAL LIGHT and provides a view of the backyard, and a CONVENIENT LAUNDRY ROOM is located just off the Kitchen. Down the hallway, you’ll find THREE BEDROOMS, each featuring a STYLISH CEILING FAN and WALK-IN CLOSET for comfortable living and convenient storage. The Primary Suite presents a private retreat with its own en suite Bath, complete with a MODERN VANITY AND TILED WALK-IN SHOWER. A SECOND FULL BATH with a modern vanity and tub/shower combination, is conveniently located near the additional Bedrooms.The Kitchen provides access to the backyard, where there's an OPPORTUNITY to create an outdoor space that reflects your own style, whether you envision a GARDEN, entertaining area or a place to relax under the Florida sunshine. With its GENEROUS CORNER LOT, mature shade trees and NO HOA, there’s room to make this property your own. Enjoy a GREAT LOCATION, just 2 miles from the charm and character of HISTORIC DOWNTOWN WINTER GARDEN, where you can explore local shops and restaurants, browse the popular PLANT STREET MARKET, visit the SATURDAY FARMERS MARKET or catch a show at the GARDEN THEATRE. Outdoor enthusiasts will appreciate the nearby WEST ORANGE TRAIL, ideal for biking, jogging and leisurely strolls, and with CONVENIENT ACCESS to Florida's Turnpike and SR-429, you can easily reach Orlando’s WORLD-FAMOUS THEME PARKS. Families will appreciate the nearby GREAT SCHOOLS including, A-RATED William Maxey Elementary and West Orange High School, adding to the appeal. With its thoughtful updates, GENEROUS LOT and convenient access to everything WINTER GARDEN has to offer, this home is FULL OF POTENTIAL and ready for its next chapter. Call and schedule your private tour today!

1444 Kenny Court, Winter Garden

622 Sigler Drive, Winter Garden

622 Sigler Drive, Winter Garden

3 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Gardenia floor plan, offering 3 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, Calacatta countertops, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

622 Sigler Drive, Winter Garden

620 Sigler Drive, Winter Garden

620 Sigler Drive, Winter Garden

4 Beds ⋅ 3 Baths ⋅ Lakeview Village Estates SubDv. ⋅ 34787 Zip Code

Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Under Construction. Welcome to Lakeview Village Estates — an exclusive new community by award- winning Davila Homes, featuring just 40 homes that seamlessly blend timeless architecture, superior construction, and the quiet elegance of true exclusivity. Sophistication is built into Lakeview’s DNA. From the carefully selected finishes to the premium appliances that elevate every kitchen, each detail was chosen to enhance comfort, durability, and aesthetic excellence. The Bayview floor plan, offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed open-concept layout. This residence showcases upgrades, including engineered hardwood flooring throughout, and a chef’s kitchen designed for both functionality and style. Location is everything — and Lakeview Village Estates delivers. Perfectly situated in the heart of the Golf Cart District, you’re just steps from Plant Street, the Farmers Market, Crooked Can Brewery, and more. From vibrant farmers’ markets and celebrated dining to community parks and cultural centers — this is where quality of life effortlessly thrives. *All renderings, floor plans, and marketing materials are conceptual and for illustrative purposes only. Actual home design, materials, finishes, dimensions, and specifications may vary and are subject to change without notice. *The estimated completion date is early January 2027.

620 Sigler Drive, Winter Garden

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