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$1,495,000
4 Beds ⋅ 5 Baths ⋅ Winter Garden Shores 2nd Add SubDv. ⋅ 34787 Zip Code
Discover elevated living and the Winter Garden lifestyle in downtown's newest custom residence! Ideally positioned off the shores of Lake Apopka and within the beloved golf cart district, this exceptional home offers effortless access to Plant Street’s charming shops, restaurants, Farmers Market, Brewery and West Orange Trail. Thoughtfully designed by locals with a deep appreciation for the character of this historic city, this exquisite 4 bedroom, 4.5-bath home blends timeless charm with refined modern finishes throughout. Majestic oaks beautifully frame the home’s craftsman-inspired architecture, while the expansive front porch invites relaxation. Inside, an open-concept design and modern kitchen are curated for both everyday comfort and endless entertaining. Inviting living spaces are complemented by elevated finishes, a wine bar, custom built-ins, a butler’s pantry & outdoor kitchen. Creatively designed to include a drop zone with a one-of-a-kind dog wash station. All bedrooms feature ensuites and custom closets. Don't miss this one-of-a-kind opportunity. Schedule your private showing today!

412 N Boyd Street, Winter Garden
$1,349,000
5 Beds ⋅ 4 Baths ⋅ Cooper & Sewell Add SubDv. ⋅ 34787 Zip Code
Experience the best of Historic Winter Garden living in this brand-new Craftsman-style home, ideally located just steps from downtown dining, shopping, entertainment, and the renowned West Orange Trail. Originally a charming 1950s bungalow, the 576 sq. ft. home has been completely renovated and thoughtfully expanded into a stunning 2,800 sq. ft. residence offering 5 bedrooms, 4 bathrooms, and exceptional modern upgrades throughout. Relax on the inviting front porch and enjoy the charm and atmosphere of this idyllic golf cart community. Inside, a bright and spacious open floor plan welcomes you with designer finishes, 10-foot ceilings, luxury waterproof vinyl plank flooring, plantation shutters, 8-foot doors, and elegant architectural details throughout. The heart of the home is the spectacular chef’s kitchen featuring premium LG stainless steel appliances, built-in oven and microwave, induction cooktop, wine fridge, oversized island with seating and storage, 42” refrigerator, and an enormous walk-in pantry complete with an additional retro-style refrigerator. The adjoining family room showcases a custom fireplace with built-in storage and two sets of French doors opening to a large covered lanai with summer kitchen, overlooking the beautifully landscaped and fully fenced backyard with additional deck space for entertaining and relaxing. The luxurious primary suite offers custom walk-in closets, a spa-inspired en-suite bath, and private French doors leading to a secluded patio and deck area. A separate lower-level wing includes two additional bedrooms, a full bath, and utility room, creating endless possibilities for an in-law suite, home office, theater room, or private guest retreat. Upstairs, you’ll find two spacious bedrooms, including one with en-suite bath, an additional full bath, linen storage, and generous extra storage space. Additional highlights include a covered carport with EV charging outlet, oversized driveway with parking for at least 6 cars, 2-zone A/C system, gutters with leaf guards, upgraded lighting, charming picket fencing, lush landscaping, and a 10x8 storage/workshop. Live the coveted Winter Garden lifestyle with golf cart access to charming boutiques, restaurants, breweries, parks, the weekly farmers market, Lake Apopka, splash pad, and more. This exceptional home perfectly combines historic charm with luxurious modern living in one of Central Florida’s most sought-after communities. Don’t miss this rare opportunity!

217 W Bay Street, 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
$225,000
2 Beds ⋅ 2 Baths ⋅ The Grove Resort SubDv. ⋅ 34787 Zip Code
Welcome to The Grove Resort & Water Park in Winter Garden, FL. This fully furnished 2-bedroom, 2-bathroom condo-hotel unit offers an open floor plan designed for functionality and comfort. The kitchen features modern appliances, solid surface countertops, and ample cabinet space. The living and dining areas provide direct access to a private screened balcony. The primary suite includes an en-suite bathroom with a soaking tub, separate glass-enclosed shower, and dual vanities. The second bedroom is well-sized and located near a full bathroom, providing additional accommodation flexibility. The Grove Resort amenities include multiple pools, water park with slides and lazy river, surf simulator, fitness center, full-service spa, on-site dining, and 24-hour front desk service. The property participates in a rental program, offering short-term rental capability. Conveniently located near Walt Disney World and major Orlando attractions, with access to shopping, dining, and highways. Schedule a showing to learn more.

14501 Grove Resort Avenue Unit 1343, Winter Garden
$695,000
4 Beds ⋅ 4 Baths ⋅ Signature Lakes Ph 3b-4, 3b-5 & 3b-7 83/27 Lot 184 SubDv. ⋅ 34787 Zip Code
Price Improvement – Welcome to 5966 Cypress Hill Rd, located in the highly sought-after Independence community of Winter Garden. This well-maintained home offers a rare blend of privacy, space, and lifestyle amenities. Situated on a larger-than-average lot with no rear neighbors, the home backs up to an open area, creating a peaceful and private setting—perfect for relaxing or entertaining. Features include a covered side lanai, extended driveway, and detached garage, offering both functionality and additional space. Enjoy resort-style living in Independence, including: • Two private boat ramps with access to Lake Speer and Lake Hancock • Two clubhouses, pools, fitness centers, and sports courts • Internet included through Spectrum as part of the HOA • Walking trails, parks, and frequent community events • Internet included through Spectrum as part of the HOA The home is zoned for top-rated schools and conveniently located near shopping, dining, and major highways. Solar System: Property includes a solar system with an existing loan. Buyer to assume solar loan. Note: Water softener not included but may be purchased separately. Solar loan assumption required; details available upon request.

5966 Cypress Hill Road, Winter Garden
$2,500,000
4 Beds ⋅ 5 Baths ⋅ 34787 Zip Code
Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with approximately 844 linear feet of lakefront property on Lake Roper. Home could also be built as a multigen and could be larger if needed with ample room for multiple garage spaces as well. This is a RARE OPPORTUNITY to acquire this much lakefront property and land but be in close proximity to city center, major thoroughfares, restaurants, theme parks, international airports. Value is in the land -- get a free house!

13377 Lake Butler Boulevard, Winter Garden