Island Pointe Sub Single Family Homes For Sale in Winter Garden - 3 homes

Remarks: Welcome to a home that feels right the moment you arrive. Set beneath the shade of mature oak trees on a 100-foot-wide lot in Winter Garden’s golf cart district, this beautifully maintained single-story home in Island Pointe invites you to slow down, breathe a little deeper, and truly enjoy where you live. The wide, covered front porch stretches across the entire front of the home, creating the perfect place for morning coffee, evening conversations, and everything in between. Step inside and you’re greeted by soaring vaulted ceilings and natural light that pours in from every angle, giving the home an open, airy feel that lives larger than its footprint. The layout flows effortlessly with multiple living and dining spaces designed for both connection and flexibility. At the center of it all is a generously sized kitchen with abundant counter space and a center island that opens seamlessly to the family room. This is where life happens. Holidays, casual dinners, and late-night conversations all find their place here. The split floor plan offers privacy and comfort. The owner’s suite is tucked away and serves as a peaceful retreat with a walk-in closet and a spacious en-suite bath featuring dual sinks, a garden tub, and a separate shower. On the opposite side of the home, two additional bedrooms provide the ideal setup for family, guests, or a home office. This home has been lovingly cared for and offers something buyers are always searching for but rarely find: solid construction with major system updates already done, including a newer roof, updated HVAC, and a brand new water heater. The finishes reflect its original character, giving you the opportunity to modernize at your own pace and build meaningful equity along the way. But what truly sets this home apart is the lifestyle. Located in the highly sought-after Golf Cart District of historic Downtown Winter Garden, you are just minutes from everything that makes this area so special. Hop on your golf cart or bike and head to Plant Street where you’ll find charming boutiques, incredible dining, live music, festivals, and the beloved Saturday Farmers Market. Enjoy local favorites like Crooked Can Brewery and Food Hall and Scoops Ice Cream only a quick ride away. Spend your weekends exploring the West Orange Trail or relaxing at nearby Newton Park, the City Pool, playground, fishing pier, and public boat ramp. Whether it’s a morning ride, an afternoon on the water, or an evening out, everything you need is right at your fingertips. Daily convenience is just as impressive, with multiple grocery options nearby and shopping along Highway 50. You are also close to top-rated schools, Winter Garden Village, AdventHealth, and have easy access to the 429 and Florida Turnpike. All of this, paired with low HOA dues and a welcoming, established neighborhood, makes this home not just a great purchase, but a smart investment in both lifestyle and long-term value. Homes like this do not come around often. A single-story layout, a prime location, strong bones, and the chance to make it truly your own. Come see it in person. Walk the space. Feel the openness. Sit on the front porch and imagine life unfolding here.

Listing is courtesy of: UPWELL REALTY LLC (407-926-9960)

Listing Agent: Kyle Madorin Pa (407-504-9247)

Remarks: Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer-construction single-story home offers a blend of modern comfort and timeless style that’s sure to impress. As you enter, custom tile in the foyer sets the tone, with a versatile flex room to the right—perfect for a home office, formal dining room, playroom, or whatever suits your lifestyle.The open-concept design seamlessly connects the kitchen, dining, and family areas, creating an ideal space for entertaining. The large kitchen island is perfect for cooking, casual meals, or hosting friends and family. Sliding glass doors open to create an effortless indoor-outdoor living experience—perfect for those quintessential Florida days. The split floor plan offers privacy, with the primary suite serving as a true retreat, complete with high ceilings, a double vanity, and a spa-like shower. On the opposite side of the home, you’ll find three additional spacious bedrooms, each with plantation shutters and high end laminate flooring. After a long day, unwind on your fully screened back porch with space for multiple seating areas, or head to the side yard to tend your garden. The thoughtfully designed outdoor living space offers plenty of room for grilling, dining, and relaxing—an entertainer’s dream. Just minutes from your front door, Winter Garden’s vibrant Plant Street awaits, offering an award-winning farmer’s market, local dining, boutique shopping, art galleries, Crooked Can Brewery, the West Orange Trail, and year-round festivals.This is a rare opportunity to own a beautifully crafted home in one of Winter Garden’s most desirable neighborhoods—where modern living meets small-town charm. Call for your private showing today.

Listing is courtesy of: MAINFRAME REAL ESTATE (407-513-4257)

Listing Agent: Katie Bray (407-779-6677)

Remarks: LUXURY RENOVATED 4-BED HOME WITH NEW ROOF + AC — OVERSIZED 3-CAR GARAGE — MOVE-IN READY This beautifully renovated 4-bed, 2.5-bath single-family home in the heart of Winter Garden (34787) is truly move-in ready — offering a luxury 2025 redesign from top to bottom. Located in the highly desirable Golf Cart District, this home sits on a quiet cul-de-sac just minutes from Downtown Winter Garden, Plant Street Market, and the West Orange Trail. The interior features a bright open floor plan with dramatic double-height ceilings, brand-new tile flooring downstairs and durable LVP upstairs, all-new baseboards and trim, and a fully updated 2025 kitchen with stone countertops and modern cabinetry. The spa-style primary suite includes two walk-in closets, a glass walk-in shower, and a soaking tub. Major upgrades include a new roof, new AC, updated electrical and plumbing, and fresh exterior paint — making this home feel like new construction. The oversized 3-car garage provides rare extra storage and golf cart space. Only 4 minutes to Newton Park with a public boat ramp — perfect for lake access, sunsets, and outdoor recreation. Schedule your private showing today!

Listing is courtesy of: SAVVY AVENUE, LLC (888-490-1268)

Listing Agent: Moe Mossa (888-490-1268)