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$599,999
4 Beds ⋅ 3 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
Virtually Staged. This is the one in Winter Garden's Golf Cart District. SELLER BONUS: from now until July 31st, the seller will credit up to $5,000 toward a privacy fence on any full-price contract. A fully renovated 4-bed, 2.5-bath home on a corner lot in the golf cart community of Island Pointe, and it is move-in ready. The 2025 updates cover everything: new roof, new AC, updated electrical, updated plumbing, new tile downstairs, LVP upstairs, and a brand new kitchen with stone countertops and modern cabinetry. Double-height ceilings and natural light greet you at the entry, and the kitchen flows right into the living space so the home feels open and connected. The kitchen has stone countertops, soft-close cabinets, a farmhouse deep sink, and real counter space that works for everyday life. The primary suite is its own retreat, with two walk-in closets, a glass walk-in shower, and a soaking tub. Three additional bedrooms give you room to grow. Outside you get a 3-car garage, a corner lot, and a quiet cul-de-sac, all inside the Island Pointe golf cart community. HOA runs $68 a month. Hop on your golf cart and you are minutes from Plant Street, the Saturday farmers market, the West Orange Trail, and some of the best restaurants and coffee in downtown Winter Garden.

1005 Chase Drive, Winter Garden
$563,500
4 Beds ⋅ 3 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to ISLAND POINTE, one of Winter Garden’s most desirable communities, ideally located in the area's sought-after GOLF COURSE DISTRICT, just minutes from Historic Downtown Winter Garden and the vibrant Plant Street corridor. Here, you can embrace the true Florida lifestyle—hop on your golf cart and enjoy easy access to award-winning restaurants, boutique shopping, breweries, the famous Winter Garden Farmers Market, and year-round community events. This beautifully maintained CUSTOM BUILT home offers nearly 3,000 square feet of thoughtfully designed living space, featuring 4 spacious bedrooms, 3 full bathrooms, a DEDICATED OFFICE, and a highly functional open floor plan perfect for today's lifestyle. From the moment you enter, you'll appreciate the architectural character of the elegant rounded corners, soaring living spaces, and abundant natural light. Designed with both privacy and functionality in mind, the home features a highly desirable three-way split bedroom floor plan, making it ideal for families, guests, multigenerational living, or those who work from home. The dedicated office provides the perfect remote workspace while maintaining separation from the bedroom wings. At the heart of the home is a chef-inspired kitchen designed for entertaining, featuring an OVERSIZED BREAKFAST BAR, DOUBLE PANTRIES, abundant cabinetry, and generous prep space. The kitchen flows seamlessly into the main living area, where a stunning three-panel pocket sliding glass door opens the home to the outdoors, creating the ultimate indoor-outdoor Florida lifestyle. The spacious primary suite serves as a private retreat, while the secondary bedrooms are thoughtfully positioned throughout the home for maximum comfort and privacy. Outside you will find your private backyard retreat, complete with a covered lanai and a convenient outdoor shower, perfect after gardening, outdoor activities, or future pool days. The FULLY FENCED backyard offers plenty of room to design and build the custom pool of your dreams, while still leaving ample space for outdoor entertaining, pets, play areas, or gardening. Major updates include ROOF(2019) WATER HEATER(2021) and two HVAC systems, ensuring comfort and efficiency throughout the home. Car enthusiasts will love the OVERSIZED DRIVEWAY with a 2-car garage and extended space specifically designed to accommodate a golf cart or even just extra storage making it easy to take advantage of Winter Garden's golf-cart-friendly lifestyle. Combining a prime location, flexible floor plan, major system updates, and room to create your own backyard oasis, this home offers an exceptional opportunity in one of Winter Garden's most sought-after neighborhoods. Schedule your private showing today.

1085 Chase Drive, Winter Garden
$535,000
2 Beds ⋅ 2 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
CUSTOM SALTWATER POOL HOME ON HALF-ACRE LOT WITH PRIVATE GARDEN OASIS! Set on a spacious treed lot backing up to conservation land—with no rear neighbors—this Winter Garden home offers the perfect blend of privacy and charm. Even better, it’s only a five-minute bike ride to Historic Downtown Winter Garden and has a low HOA. The outdoor space is truly the showstopper: a saltwater pool framed by lush greenery, winding garden paths, a wooden Adirondack swing, and hidden sitting areas. Nearly 1,000 sq. ft. of covered and screened porch space expands the living area outdoors, ideal for entertaining, a man cave, or flexible bonus space. Inside, the home features Brazilian solid-wood floors, custom cabinetry, granite counters, a stone backsplash, built-in oven/microwave, and display cabinets with under-cabinet lighting. The great room stuns with cathedral beamed ceilings, a gas fireplace, and floor-to-ceiling windows that overlook the gardens. The primary suite includes vaulted ceilings, a bay window, dual closets, and a spa-style bath with double vanities, garden tub, and separate shower. A secondary bedroom is large enough to serve as a second master. Additional details include wide interior doorways for accessibility, plaster walls, a leaded-glass entry, double-pane insulated windows, and a 16-SEER A/C. The roof, replaced in 2020, is now just about 5 years old, offering peace of mind for years to come. A transferable termite bond, thoughtful design, and prime location make this home a standout in Winter Garden.

975 Sadie Lane, Winter Garden
$469,000
3 Beds ⋅ 2 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
One or more photo(s) has been virtually staged. Active Under Contract - accepting back up offers. Welcome to this spacious 3-bedroom, 2-bath home with a 2-car garage, ideally situated in the highly desirable golf cart district of downtown Winter Garden. Step inside to discover a split bedroom floor plan with vaulted ceilings and a cozy living room with fireplace, seamlessly connected to the dining area—creating a warm, inviting space for gatherings. The chef-inspired kitchen serves as the heart of the home, featuring quartz countertops, stainless steel appliances, an eat-in breakfast bar, and ample cabinetry for storage and style. Enjoy the convenience of an indoor laundry room with a sink and extra storage. The primary suite offers comfort and privacy with a generous walk-in closet and a spa-like ensuite bath, while two additional bedrooms and a full bath with dual linen closets provide plenty of space for family or guests. Relax or entertain in the expansive Florida room overlooking the manicured backyard—perfect for morning coffee or evening gatherings. Additional highlights include luxury vinyl flooring in wet areas and new carpet in the bedrooms for added comfort. Perfectly located just a five-minute bike or golf cart ride from Historic Downtown Winter Garden, this home offers easy access to local shops, restaurants, the Saturday farmers market, Lake Apopka parks, and the West Orange Trail. With a low HOA and endless possibilities for personalization, this property combines comfort, convenience, and the coveted Winter Garden lifestyle. Don’t miss your chance to call this charming home yours—schedule your private showing today!

1041 Sadie Lane, Winter Garden
$465,000
3 Beds ⋅ 2 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
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.

1035 Chase Drive, Winter Garden
$385,000
4 Beds ⋅ 3 Baths ⋅ Island Pointe Sub SubDv. ⋅ 34787 Zip Code
Please read: Seller has a quote for $52,000 for full interior renovation, new roof, AC (seller is offering a $52,000 credit at full price offer). This listing is an opportunity to buy a dream home in an established neighborhood while picking all your own colors. Cash or low LTV loan that will accept a seller providing a $52,000 credit. This stunning 4-bedroom, 2,300+square foot home combines modern elegance with comfortable living floor plan, perfectly suited for both relaxation and entertainment. Exterior: As you approach the home, you'll be greeted by lush tropical landscaping and an inviting facade. The exterior features a combination of smooth stucco and stone accents, highlighting the Florida charm. A spacious driveway leads to a two-car garage, providing ample parking for family and guests. Interior: Upon entering the home, you’ll find a bright and airy open-concept layout. Large windows flood the space with natural light, creating a warm and inviting atmosphere. Kitchen: The modern kitchen layout is a chef's delight, Ample cabinetry ensures plenty of storage, while a pantry offers additional space for all your culinary needs. Adjacent to the kitchen is a cozy dining area, perfect for family gatherings. Bedrooms: The four spacious bedrooms provide ample space for family and guests. The master suite is a peaceful retreat, complete with a walk-in closet and an en-suite bathroom featuring dual vanities, a soaking tub, and a separate shower. The additional three bedrooms are designed with comfort in mind, featuring generous closet space and large windows. One of the guest bedrooms can easily be transformed into a home office or gym, catering to your personal needs. Bathrooms: In addition to the master bathroom, a full guest bathroom serves the three additional bedrooms, while a convenient powder room is situated near the main living areas for visitors. Outdoor Space: Wrap around oversized lot. A must see, she a blank canvas.

1005 Chase Drive, Winter Garden