Explore Overlook at Hamlin, Winter Garden, FL Homes for Sale

Homes for Sale with a Pool in Overlook at Hamlin, Winter Garden, FL

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Welcome to your dedicated resource for homes for sale with a pool in Overlook at Hamlin, Winter Garden, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Overlook at Hamlin, Winter Garden, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Overlook at Hamlin, Winter Garden, FL

4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code

Designed to impress and crafted for everyday living, 5513 Thomas Square Drive is a beautifully upgraded pool home in one of Hamlin's most sought-after communities. Offering 4 bedrooms, 3.5 bathrooms, a private office, an oversized loft, a versatile flex room, and a saltwater pool, this exceptional residence seamlessly blends timeless design with modern comfort. From the moment you arrive, the stone-accented elevation, oversized driveway, and manicured landscaping create unforgettable curb appeal. Inside, soaring ceilings, abundant natural light, crown molding, custom trim work, 8-foot doors, and wood-look tile flooring establish an elegant yet welcoming atmosphere. The dramatic two-story great room is the undeniable centerpiece of the home, showcasing a custom floor-to-ceiling built-in with cabinetry, open shelving, and a heat-producing electric fireplace, beautifully complemented by decorative wood ceiling beams that add warmth and architectural character. The open-concept kitchen is equally impressive, featuring white cabinetry, granite countertops, an oversized center island, stainless steel appliances, a gas cooktop, walk-in pantry, expansive butler's pantry, and a dedicated breakfast nook overlooking the backyard. Privately tucked away on the first floor, the primary suite offers engineered hardwood flooring, dual walk-in closets with custom shelving, and a spa-inspired bath with separate vanities, a soaking tub, and an oversized walk-in shower. A private office with matching engineered hardwood flooring, formal dining room, laundry room, and powder bath complete the main level. Upstairs, three spacious bedrooms, two full bathrooms, an oversized loft, and a flexible bonus room provide endless possibilities for a media room, fitness space, playroom, or potential fifth bedroom. Step outside to your own private retreat featuring a saltwater pool with water features, covered lanai, fenced backyard, and the added privacy of no rear neighbors. Thoughtful enhancements throughout the home include the custom family room built-in with electric fireplace, decorative ceiling beams, engineered hardwood flooring in the primary suite and office, permanent exterior architectural trim lighting, a whole-home security camera system, overhead garage storage, newer kitchen appliances, a new microwave, a newer pool pump, and spray foam insulation for enhanced energy efficiency. Residents enjoy resort-style amenities including a clubhouse, community pool, playground, and dog park, all just minutes from Hamlin Town Center, top-rated schools, shopping, dining, major highways, and Walt Disney World. Blending timeless design, quality craftsmanship, and an unbeatable location, 5513 Thomas Square Drive is a rare opportunity to own a truly move-in-ready home in the heart of Winter Garden.

5513 Thomas Square Drive, Winter Garden

4 Beds ⋅ 4 Baths ⋅ Overlook 2/Hamlin Ph 2 & 5 SubDv. ⋅ 34787 Zip Code

Welcome to this spacious 4-bedroom, 3.5-bath pool home offering 4,000 square feet in the highly sought-after Overlook at Hamlin community in Horizon West. Showcasing Lake Hancock views throughout the home and Disney fireworks in the distance, this property combines generous living space, impressive architecture, and an unbeatable location in one of Winter Garden's most desirable communities. From the moment you arrive, you'll appreciate the paver driveway, fresh landscaping, side-entry two-car garage, and curb appeal. Step inside to find a formal dining room and home office. Continue into the heart of the home where soaring ceilings and a dramatic two-story design create a bright, open atmosphere. The expansive family room showcases picturesque pool and lake views, while the open-concept layout flows seamlessly into the kitchen and casual dining area, making it ideal for everyday living and entertaining. The kitchen features granite countertops, light cabinetry, two oversized islands, abundant prep space, a walk-in pantry, and a butler's pantry ideal for a coffee station. Stainless steel appliances include a Monogram built-in oven and microwave, Monogram dishwasher, and a Monogram five-burner natural gas cooktop. The first-floor primary suite offers a private retreat with pool views, two walk-in closets, and an ensuite bath complete with dual vanities, a garden tub, and a large glass-enclosed shower. An impressive staircase with decorative iron balusters leads to the second floor, where an open overlook adds to the home's spacious feel. Upstairs you'll find three additional bedrooms, all with walk-in closets, two full bathrooms, a large loft perfect for a media room or secondary living area, and a versatile flex room that can serve as a home gym, study, playroom, hobby room, or potential fifth bedroom. Combined with the dedicated first-floor office, these flexible spaces provide exceptional versatility for remote work, multi-generational living, or growing households. Two upstairs bedrooms enjoy Lake Hancock views. Step outside to the expansive screened lanai with space for outdoor dining, relaxing, and entertaining. The saltwater pool and Lake Hancock views create an exceptional outdoor setting. Residents of Overlook at Hamlin enjoy access to a clubhouse, fitness center, resort-style pool, playgrounds, golf cart-friendly streets, and community lake access. Located just minutes from Hamlin Town Center, you'll enjoy convenient access to shopping, dining, waterfront restaurants, grocery stores, PopStroke, Cinépolis Luxury Cinemas, Urban Air, and everyday conveniences. A rare opportunity to own a spacious pool home with Lake Hancock views in the heart of Horizon West and Winter Garden's thriving Hamlin area.

15264 Shonan Gold Drive, Winter Garden

5 Beds ⋅ 7 Baths ⋅ Overlook 2/Hamlin Ph 3 & 4 SubDv. ⋅ 34787 Zip Code

Experience the pinnacle of lakefront luxury in this extraordinary custom estate situated along the shores of Lake Hancock, offering over 104 feet of private waterfront frontage. Encompassing more than 5,600 square feet of meticulously designed living space, this remarkable residence seamlessly blends timeless elegance with modern comfort. Upon entering, you are welcomed by soaring ceilings, expansive living spaces, abundant natural light, and designer finishes throughout. The thoughtfully designed open floor plan is ideal for both everyday living and grand-scale entertaining. At the heart of the home, the gourmet chef’s kitchen features premium appliances, custom cabinetry, generous prep space, and a spacious breakfast area overlooking the water. The luxurious first-floor primary suite serves as a private retreat, showcasing breathtaking lake views, a spa-inspired bathroom, and an oversized walk-in closet. Each additional bedroom is generously appointed with its own en-suite bath, providing exceptional comfort and privacy for family and guests alike. Upstairs, enjoy an immersive cinematic experience in the fully equipped private home theater. Step outside to discover a true resort-style setting, complete with an infinity-edge saltwater pool, covered lanai with fireplace, and a fully equipped outdoor kitchen designed for year-round entertaining. A private dock extends into Lake Hancock, providing direct access for boating, fishing, paddleboarding, or simply enjoying spectacular sunset views. As evening falls, take in the magical sight of Walt Disney World fireworks reflecting across the water. Located within one of Horizon West’s most desirable communities, residents enjoy an exceptional lifestyle with access to resort-style amenities including a community pool, tennis courts, fitness center, banquet facilities, scenic walking paths, and neighborhood parks. Conveniently located just minutes from premier shopping, fine dining, entertainment, and top-rated schools, this is a rare opportunity to own one of Central Florida’s most impressive waterfront estates.

15138 Shonan Gold Drive, Winter Garden

2 Beds ⋅ 3 Baths ⋅ Overlook 2/Hamlin Ph 1 & 6 SubDv. ⋅ 34787 Zip Code

Come see 5545 Bowman Dr, recently updated with fresh interior paint and partial flooring replacement throughout. The kitchen features a backsplash and a convenient island providing additional workspace. The primary bedroom includes a spacious walk in closet, and the primary bathroom is equipped with double sinks for enhanced utility. Outside, a covered patio extends to a fully fenced in backyard, completing the exterior amenities. Enjoy updated comfort and practical features in this exceptional residence. Included 100-Day Home Warranty with buyer activation

5545 Bowman Drive, Winter Garden

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