Windermere Homes with Pool Amenities

Windermere Homes with Pool Amenities

Welcome to Windermere, Florida, a picturesque town nestled in the heart of Orange County, where stunning landscapes and a vibrant community come together to create an idyllic living experience. Known for its charming small-town atmosphere, Windermere offers residents a unique blend of tranquility and access to the excitement of nearby Orlando. With its scenic lakes, lush parks, and beautiful tree-lined streets, this enchanting town is perfect for families, retirees, and anyone seeking a serene lifestyle.

One of the standout features of Windermere is its selection of homes with pool amenities. Imagine stepping out of your back door to dive into your own private oasis, where you can soak up the Florida sun or host delightful gatherings with family and friends. Whether you're looking for a cozy single-family home or a luxurious estate, Windermere boasts an impressive array of properties equipped with sparkling pools that cater to every lifestyle.

Many of these homes are located in friendly neighborhoods, complete with excellent schools, recreational facilities, and easy access to shopping and dining options. The community spirit in Windermere is palpable, as residents often come together for local events, farmers' markets, and seasonal festivities.

With its perfect blend of natural beauty, modern amenities, and a welcoming community, Windermere is not just a place to live—it's a place to thrive. Explore the charming homes with pool amenities available in this stunning town, and discover your dream home in Windermere today!

Newest Windermere Homes with Pool Amenities

3 Beds ⋅ 3 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code

Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Design upgrades include 42" cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless steel appliances. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and practical design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living.

5577 Lemon Orchard Bend, Windermere

3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code

Welcome to Berkshire Park, a highly sought-after community where timeless style, everyday comfort, and low-maintenance living come together in the heart of Windermere. This impeccably maintained 3-bedroom, 2.5-bath townhome offers 1,644 square feet of beautifully designed living space, combining tasteful finishes with exceptional functionality. The beautifully appointed kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a newly purchased refrigerator and microwave. A spacious dining area provides the perfect setting for everything from casual breakfasts to holiday gatherings, while a walk-in pantry with ample storage keeps the space organized and functional. French doors lead from the kitchen to a private, fenced patio, creating an inviting outdoor retreat for dining al fresco, entertaining guests, or simply relaxing in the Florida sunshine. Backing to conservation land with picturesque views of mature trees, the backyard offers a peaceful and private setting rarely found in townhome living. Seamlessly connected to the kitchen, the spacious living room offers a warm and welcoming atmosphere, highlighted by an electric fireplace, which is included with the sale of the home. A detached two-car garage completes the property, providing additional storage and everyday convenience. Upstairs, the spacious primary suite serves as a private retreat, complete with a walk-in closet, dual vanities, and an oversized walk-in shower. Two additional bedrooms share a full bathroom, offering comfortable accommodations for family, guests, or a dedicated home office. Residents of Berkshire Park enjoy an exceptional lifestyle with amenities designed for both recreation and relaxation, including a community pool, tennis courts, basketball courts, and scenic walking trails winding around tranquil ponds beneath a canopy of mature trees. The HOA further enhances the ease of homeownership by providing landscaping, structural exterior maintenance, and pest control, allowing you to spend more time enjoying everything this beautiful community has to offer. Ideally located just minutes from Walt Disney World, Winter Garden Village, Hamlin Town Center, premier shopping and dining, major roadways, and top-rated schools, this move-in-ready residence offers the perfect balance of location, lifestyle, and convenience. Whether you're searching for your primary residence, a seasonal retreat, or an investment opportunity, 12914 Vennetta Way presents an exceptional opportunity to own a beautifully maintained home in a highly sought-after Windermere community.

12914 Vennetta Way, Windermere

3 Beds ⋅ 2 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code

Welcome to this beautifully maintained one-story home in the highly desirable Summerport community of Windermere! Offering 3 bedrooms, 2 bathrooms, and a versatile office/den, this home reflects true pride of ownership and is ready for its next owners. From the moment you arrive, you'll appreciate the excellent curb appeal and inviting exterior. Inside, the spacious open floor plan features elegant tray ceilings, crown molding, luxury vinyl flooring, upgraded ceiling fans throughout, a formal dining room, and a stylish modern kitchen complete with stainless steel appliances, a gas range, a large center island, and an oversized breakfast bar that's perfect for everyday living and entertaining. All appliances, including the washer and dryer, are included for your convenience. The private primary suite offers a beautiful barn door, California Closets, dual vanities, and a relaxing retreat at the end of the day. Throughout the home you'll find plantation shutters, adding both charm and functionality. Step outside to your own backyard oasis featuring a screened lanai overlooking a beautifully landscaped backyard and sparkling pool, only 2.5 years old, with the required safety door locks already in place. The home also includes a water softener, an epoxy-coated garage floor, a gas water heater, and energy-efficient double-pane windows installed in 2026. Additional updates include a new A/C installed in 2024 and the interior and exterior professionally painted in 2025. A two-car garage plus an extended driveway provide plenty of parking. Ideally located just minutes from Winter Garden Village, you'll enjoy easy access to shopping, restaurants, entertainment, major roadways, and the Florida Turnpike. Summerport is known for its outstanding amenities, scenic walking trails, parks, playgrounds, community pool, fitness center, tennis and basketball courts, and picturesque lakes. This exceptional home combines comfort, style, thoughtful upgrades, and an unbeatable location—don't miss the opportunity to make it yours!

13160 Sunkiss Loop, Windermere

3 Beds ⋅ 2 Baths ⋅ Lake Sawyer South Ph 01 SubDv. ⋅ 34786 Zip Code

Virtually Staged. Discover this beautifully maintained 3-bedroom, 2-bath corner-lot home in Windermere. Surrounded by tree-lined streets and a welcoming neighborhood atmosphere, this home combines timeless charm with everyday convenience. Enjoy relaxing on the covered front porch, perfect for morning coffee, visiting with the neighbors or unwinding after a long day. Inside, the thoughtfully designed floor plan offers comfortable living spaces that are ideal for both everyday life and entertaining. The home features a galley style kitchen positioned between a cozy breakfast nook and the dining room, allowing for both casual and traditional dining options. The split-bedrooms provide added privacy. The on-suite primary bathroom features a soaking tub, dual vanities and a separate stand alone shower. The shower glass and tile were replaced in the fall of 2025. The home features real bamboo hardwood flooring in all interior areas except the kitchen, nook, bathrooms and laundry room. From the living room, open the sliders and step into your oversized patio. This patio has a generous covered area and a screened portion, allowing you to comfortably enjoy outdoor living while being protected from the Florida sun, weather and insects. The fully vinyl fenced backyard has two access gates and is ideal for pets, play or outdoor gatherings. New gutters and water heater were added in 2026, offering added peace of mind. Residents of this community enjoy access to a resort-style pool, basketball court, tennis/pickleball courts and a walking path, offering endless opportunities for recreation, relaxation and an active lifestyle. Whether you are searching for your first home, looking to downsize, or simply wanting to enjoy the charm and lifestyle that Windermere is known for, this property offers an exceptional opportunity in a highly sought-after location. Conveniently located near excellent schools, shopping, dining, theme parks and major roadways, this home offers easy access to everything Central Florida has to share. Don’t miss this opportunity - schedule your showing today.

13231 Roxboro Road, Windermere

5 Beds ⋅ 5 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code

Welcome to this exceptional two-story luxury home in one of Windermere's most sought-after communities. Situated on a beautifully landscaped 0.38-acre lot, this meticulously maintained 5-bedroom, 4.5-bathroom residence offers 3,036 square feet of elegant living space designed for comfort, functionality, and entertaining. A long private driveway and charming front courtyard create a grand first impression. Inside, you'll discover spacious living and entertaining areas filled with natural light, soaring ceilings, and an inviting floor plan that flows effortlessly from room to room. Whether hosting holiday gatherings or enjoying quiet evenings at home, every space has been thoughtfully designed for comfortable living. The gourmet kitchen serves as the heart of the home and features abundant cabinetry, generous counter space, and premium appliances. Included with the sale are the kitchen refrigerator, stove/range, built-in wine refrigerator, built-in espresso machine, washer, and dryer, allowing the next owner to move in with ease. One of this home's most distinctive features is its private detached suite, located separately from the main residence with its own private entrance and full bathroom. This versatile space is ideal as an in-law suite, private guest quarters, executive home office, fitness studio, creative workspace, or media room, offering endless possibilities while maintaining privacy from the main living areas. The second story offers generously sized bedrooms and comfortable accommodations for family and guests. The staircase and upstairs bedroom carpeting were replaced approximately 1.5 years ago, while one upstairs bedroom showcases beautiful hardwood flooring, adding warmth and character. Step outside into your own private backyard retreat. The fully fenced backyard provides both privacy and security while creating the perfect setting for outdoor entertaining, pets, or simply relaxing in your own personal oasis. The sparkling swimming pool offers exceptional flexibility, as it can be operated as either a traditional chlorine pool or converted to saltwater, depending on the owner's preference. Recent upgrades include a new pool motor and complete pool filter assembly installed in 2025, and all existing pool equipment is included with the sale. The existing wicker patio furniture also conveys, allowing the next owner to begin enjoying the outdoor living space immediately. The property has been meticulously maintained, with all HVAC units receiving regular service, one HVAC unit replaced, and the tile roof professionally maintained annually, including semiannual soft washing, tile replacement, and recementing as needed to preserve both appearance and longevity. The garage features epoxy flooring, an insulated garage door, its own air-conditioning unit, built-in shelving, and a workbench, while a backyard storage shed provides additional storage. Conveniently located just minutes from top-rated schools, championship golf courses, world-class dining, upscale shopping, Disney, and the Butler Chain of Lakes, this exceptional home offers the perfect blend of luxury, flexibility, and everyday convenience. Whether you're looking for multigenerational living, a private home office, or simply an impeccably maintained luxury residence, this Windermere gem is truly move-in ready.

11434 Rapallo Lane, Windermere

5 Beds ⋅ 4 Baths ⋅ Windermere Isle Ph 2 SubDv. ⋅ 34786 Zip Code

Experience the perfect blend of elegance, comfort, and modern convenience in this exceptional 5-bedroom, 4-bathroom home in the highly sought-after Windermere Isle community. Enjoy nightly Disney fireworks from the second floor! A charming covered front porch welcomes you inside, where the foyer showcases beautiful wood-look tile flooring that flows seamlessly throughout the main living areas. Thoughtfully designed with both functionality and flexibility in mind, this home offers space for a variety of lifestyles. Just off the entry is a spacious first-floor bedroom with a large walk-in closet and convenient access to a full bath, making it ideal for guests, a home office, fitness room, or creative space. The elegant formal dining room with tray ceiling is ready to host everything from holiday gatherings to intimate dinners. Designed to impress, the chef’s kitchen features quartz countertops, sleek gray shaker cabinetry, stainless steel appliances, built-in double convection ovens, a 5-burner gas cooktop, French door refrigerator, stylish subway tile backsplash, a spacious island with seating, and plenty of room for casual dining. A butler’s pantry and oversized walk-in pantry provide exceptional storage. Step outside and discover your own private Florida oasis. The heated saltwater pool and spa, panoramic screen enclosure, summer kitchen, extended paver patio, and oversized fenced backyard create the perfect setting for entertaining, outdoor dining, or simply relaxing in the Florida sunshine. The staircase with modern metal balusters leads to an expansive loft that provides additional living space perfect for movie nights, gaming, hobbies, or a quiet retreat. The luxurious primary suite offers two generous walk-in closets and a spa-inspired bath featuring dual vanities, a freestanding soaking tub, and a separate glass-enclosed shower. Three additional spacious bedrooms, all with walk-in closets—including one with a private en-suite bath—complete the second floor. Engineered hardwood flooring installed throughout the upper level in 2024 adds warmth, style, and durability. Additional highlights include overhead garage storage, a side-by-side refrigerator, bike racks, a convenient drop zone, and a washer and dryer that convey with the home. Fully paid whole-house solar panels were added in 2024, along with a Westinghouse whole-house water softener, filtration system, and drinking water purification system. Outside, you’ll enjoy beautifully landscaped gardens, mature lemon and orange trees, and generous green space. Community amenities include a resort-style pool with cabana and playground. HOA dues include lawn fertilization and mowing for both front and rear yards, pest control, cable television, and high-speed internet. Located just minutes from Walt Disney World, with approximately 11 minutes to the Magic Kingdom parking lot and 13 minutes to EPCOT, this home also offers convenient access to exceptional shopping, dining, entertainment, and highly rated schools. This is more than just a beautiful home—it’s a place to relax, entertain, and create lasting memories. Home is where your story begins… let me help you start your story.

8254 Procida Isle Lane, Windermere

5 Beds ⋅ 4 Baths ⋅ Belmere Village G-5 SubDv. ⋅ 34786 Zip Code

Virtually Staged. Welcome home to 11773 Bella Milano Ct — a 5-bedroom, 3.5-bath residence on a quiet cul-de-sac in the sought-after gated community of Belmere Village. Enjoy rare privacy with a wooded conservation view at the rear, bordering a park with no through-access, and a lot size just under a quarter acre. Inside, engineered hardwood and tile flooring flow through the main living areas (one living room is carpeted), beneath vaulted and 9'4"+ ceilings on the first floor. The spacious primary suite is a true retreat, featuring a garden tub, separate shower, dual vanities, private toilet closet, walk-in closet, and an adjoining sitting room with its own exterior entrance to the backyard. Four additional bedrooms deliver flexible space for family, guests, or a home office. The kitchen features stainless steel appliances. Seller offering up to $10,000 in concessions toward closing costs, rate buydown, and/or home upgrades. Major systems are well maintained: both HVAC units have been replaced (2023 and 2026), and the tile roof was resurfaced in 2023 with no major repairs since. A 2-car garage completes the home. Belmere's $130/month HOA includes a gated entrance, community pool, clubhouse, tennis courts, basketball court, sand volleyball court, playground, and fitness center — all within Windermere's top-rated school zone and minutes from the Butler Chain of Lakes and Winter Garden's Plant Street district.

11773 Bella Milano Court, Windermere

3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code

This Berkshire Place townhome offers a thoughtfully arranged two-story layout with three bedrooms, inviting living spaces, and a convenient Windermere location. The covered front porch opens to a bright living room with a ceiling fan, while the adjoining dining area creates an easy connection to the kitchen. Dark wood cabinetry, stainless-steel appliances, recessed lighting, a window above the sink, and a raised breakfast bar provide a functional kitchen setup with space for casual seating. A half bathroom completes the main level. Upstairs, the primary suite features windows on two sides, a walk-in closet, and an en suite bathroom with a long dual-sink vanity and enclosed shower. Two additional bedrooms, each with a ceiling fan and closet, share a full bathroom with a tub and shower combination. Just beyond the dining area, double glass doors open to an enclosed brick-paver courtyard that provides a low-maintenance setting for outdoor dining, grilling, or container gardening. The courtyard also connects directly to the rear-entry two-car garage, creating convenient access between the home and parking area. Berkshire Place offers tree-lined sidewalks, a playground, a community pool overlooking the water, and sports courts, adding opportunities to enjoy the outdoors close to home. Located in Windermere’s Lakeside Village area, the townhome is convenient to nearby grocery stores, shopping, restaurants, and everyday services, with access to Winter Garden Village, area theme parks, and destinations throughout Central Florida.

7712 Fordson Lane, Windermere

3 Beds ⋅ 2 Baths ⋅ Lake Sawyer South Ph 01 SubDv. ⋅ 34786 Zip Code

Set on a corner lot in Lake Sawyer South, this single-story Windermere home combines a new roof completed in May 2026 with a remodeled kitchen and bathrooms, custom woodwork, and inviting indoor-outdoor living. The three-bedroom, two-bath layout offers approximately 1,706 square feet with wood flooring through the main living areas and bedrooms, plantation shutters, crown molding, window casings, chair rail details, and an enhanced entry framed by custom trim. The main living room connects comfortably to the kitchen and breakfast area, while a separate front flex space can adapt to work-from-home needs, hobbies, or additional gathering space. The remodeled kitchen features white cabinetry, a blue subway-tile backsplash, an apron-front sink, stainless steel appliances, and breakfast-bar seating, with the refrigerator included. In the primary suite, the remodeled en suite bath offers dual sinks, a dedicated makeup vanity, and a glass-enclosed shower, while two additional bedrooms share an updated guest bath. Custom French-style sliding doors extend the living space to a tiled screened patio with all-season panels, creating a comfortable place to relax throughout the year. Beyond the enclosure, a full-length brick-paver patio and privacy-fenced yard provide additional outdoor space, while the covered front porch adds another welcoming spot to enjoy the corner-lot setting. Additional improvements include elastomeric exterior paint, a quiet-drive garage door opener, and an included washer and dryer. Community amenities include a pool, playground, tennis court, and basketball court, rounding out a home that blends thoughtful updates, character, and everyday convenience in the Horizon West area.

13403 Riggs Way, Windermere

2 Beds ⋅ 2 Baths ⋅ Summerport Phase4 SubDv. ⋅ 34786 Zip Code

Location, Location, Location! Welcome to this charming one-story end-unit townhome in the highly desirable Summerport community of Windermere! Ideally situated to Keene's Crossing Elementary School and the community's exceptional amenities. The open-concept floor plan creates a bright, spacious atmosphere, seamlessly connecting the living room, dining area, and kitchen—perfect for everyday living and entertaining. The generously sized eat-in kitchen features a breakfast bar, LG appliances, 42-inch cabinetry, granite countertops, tile flooring, an attractive art niche, and French doors that open to a covered, screened porch. The primary suite boasts a double tray ceiling, walk-in closet, dual vanities, a relaxing soaking tub, and a linen closet. The secondary bedroom is conveniently located adjacent to the guest bathroom. Additional highlights include an inside laundry room with Maytag washer and dryer included, a spacious rear-entry two-car garage, and all ceiling fans, light fixtures, and window treatments conveying with the sale. Summerport residents enjoy an impressive array of amenities, including a clubhouse, resort-style pool, fitness center, tennis courts, basketball and volleyball courts, scenic walking trails, fishing docks, playgrounds, and more. Conveniently located near SR 429, Hamlin Town Center shopping, dining, world-famous theme parks, and countless Central Florida attractions, this home truly offers the perfect combination of location, lifestyle, and value!

14250 Sonco, Windermere

3 Beds ⋅ 3 Baths ⋅ Tennyson Pk/Summerport SubDv. ⋅ 34786 Zip Code

Virtually Staged. This one has it all! Welcome home to this beautifully updated townhome in the highly sought-after Summerport community, where charm, comfort, and picturesque water views come together to create an exceptional living experience. From the moment you arrive, you'll be captivated by the home's inviting curb appeal, featuring a spacious front porch, attractive architectural details, elegant exterior lighting, and landscaping that enhances its timeless character. Inside, you'll discover a bright and welcoming interior highlighted by fresh paint, stylish luxury vinyl plank flooring throughout, and thoughtfully designed living spaces that offer both comfort and functionality. The well-appointed kitchen features crisp white cabinetry, stainless steel appliances, and ample storage, creating the perfect setting for everything from casual meals to entertaining guests. The open-concept layout flows seamlessly into the living and dining areas, while ceiling fans throughout the home provide added comfort and energy efficiency. Large windows invite natural light inside and frame beautiful views of the lake, creating a peaceful backdrop for everyday living. Additional highlights include generous garage parking and a desirable location within one of the area's most established communities. Enjoy easy access to community amenities including parks, clubhouse, community pool, tennis and basketball courts, all while coming home to tranquil water views and a welcoming neighborhood atmosphere. This exceptional Summerport home offers the perfect blend of style, convenience, and scenic beauty—don't miss your opportunity to make it yours.

5579 Somersby Road, Windermere

4 Beds ⋅ 4 Baths ⋅ Keene's Pointe SubDv. ⋅ 34786 Zip Code

Something unexpected! Something unique! An amazing space! Welcome to 6241 Blakeford Drive, where the charm, character, and glamour of this custom-built jewel box home are sure to impress. Designed to capture natural light and stunning water views, this residence offers a floor plan that is both functional and unforgettable. At the heart of the home is a spectacular Great Room featuring soaring 30-foot ceilings and dramatic picture windows that frame breathtaking views of the pool, pond, and colorful Florida sunsets. Abundant natural light fills the space, creating an inviting atmosphere that seamlessly connects the main living areas. The thoughtfully designed split floor plan places the spacious primary suite in its own private wing, complete with French doors opening to the pool and a luxurious spa inspired bath showcasing exquisite custom tilework that is truly a work of art. On the opposite side of the home, you'll find a bright office or fifth bedroom with adjacent full bath, an additional guest bedroom, and a rear bedroom overlooking the garden and water, also with convenient pool access. The boutique-style kitchen is a showpiece, highlighted by a dramatic stacked-stone exhaust wall that beautifully complements the matching stone fireplace in the great room. Together, these elements create a warm and cohesive gathering space perfect for everyday living and entertaining. The formal dining room offers flexibility as a sitting room or entertaining space, while the breakfast nook is perfectly positioned to enjoy tranquil pond views and unforgettable sunsets. Upstairs, a spacious bonus room, fourth bedroom, full bath, and stackable washer/dryer closet create a private retreat ideal for guests, extended family, or multigenerational living. Situated on just over one-third acre with 90 feet of waterfront frontage, the property enjoys long pond views and stunning sunset vistas. The oversized three-car garage and prime location just steps from the Golden Bear Clubhouse add to the home's appeal. Move-in ready and worry free with new ACs and roof (2024) new quartz countertops (2023 & 2026), new flooring (2023) and newly painted exterior (2025).

6241 Blakeford Drive, Windermere

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