Windermere Homes with Pool Community Features

Windermere Homes with Pool Community Features

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County that perfectly combines small-town charm with modern conveniences. Known for its stunning lakes, lush landscapes, and friendly community, Windermere offers a serene escape from the hustle and bustle of city life while still being conveniently located just a short drive from Orlando's vibrant attractions.

One of the highlights of living in Windermere is the abundance of homes featuring inviting pools, providing the perfect oasis for relaxation and recreation. Imagine stepping into your backyard to find a sparkling pool surrounded by tropical landscaping, ideal for family gatherings, summer barbecues, or simply unwinding after a long day. With many homes in this community designed with outdoor living in mind, you’ll find ample space for entertaining or enjoying quiet moments in the sun.

Windermere is not just about beautiful homes; it’s also a community that values connection and leisure. Residents can take advantage of nearby parks, walking trails, and scenic waterfronts, making it easy to embrace an active lifestyle. The town hosts various events throughout the year, fostering a sense of camaraderie among neighbors and creating lasting memories.

With its blend of natural beauty, family-friendly amenities, and a welcoming atmosphere, Windermere is truly a place to call home. Whether you’re looking for a tranquil retreat or a vibrant community, this charming town has something for everyone. Come discover the allure of Windermere, where your dream home with a pool awaits!

Newest Windermere Homes with Pool Community Features

7663 Bramwell Street, Windermere
$369,990
3 Beds ⋅ 3 Baths ⋅ Wickham Park 04 05 06 09 10 11 12 01 SubDv. ⋅ 34786 Zip Code
Welcome to 7663 Bramwell Street, a well-kept 3-bedroom townhome in Windermere’s Wickham Park community, offering low-maintenance living in one of West Orange County’s most in-demand areas. With 1,510 sq ft, the home features an open main level where the living, dining, and kitchen areas flow together, ideal for everyday living and entertaining. The kitchen offers an open layout , a French door fridge and spacious bar and island. Upstairs, sits the primary suite, joined by two additional bedrooms with generous closet space and a full bath. Additional highlights include a 5 year old roof and ac, an inside laundry area, and an detached 2 -car garage. The HOA covers [exterior maintenance/lawn care/community pool], so you can spend more time enjoying Central Florida. Conveniently located near Winter Garden–Vineland Road, you’re minutes from shopping, dining, and major roadways, with easy access to the theme parks and the Horizon West area. Whether you’re a first-time buyer, downsizing, or adding to your investment portfolio, this townhome is a must-see. Schedule your showing today!

7663 Bramwell Street, Windermere
13731 Calera Alley, Windermere
$465,000
3 Beds ⋅ 3 Baths ⋅ Vineyards/Horizons West Ph 2b SubDv. ⋅ 34786 Zip Code
Welcome home to this highly upgraded, move-in ready outside end unit in the Vineyards of Horizons West. This unit features a fenced side yard with patio, walkway to garage, front porch and landscaping, pond and open views. The front of the unit has a quiet courtyard setting. Inside you will find a beautiful large gourmet kitchen w/upgraded cabinets and sink, including a large kitchen island. A very large open great room and dining area. The first floor is wood look "porcelain tile" with sealed grout for minimal upkeep. Downstairs also features a spacious half bath and a large storage area under the stairs and separate laundry area. The garage is oversized with a finished floor. Upstairs are three bedrooms and a loft. Bath in the primary has been upgraded to frameless glass, a large spacious closet with extra racks added. $48K in upgrades from the builder when new. Pond and open space views from the first and second floor make the setting of this unit even more appealing. A quiet community with a park-like atmosphere, community pool and playground, and walking distance to Windermere High School.

13731 Calera Alley, Windermere
5021 Carillon Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Welcome to this beautiful home in a highly desirable community known for its top-rated schools and beautifully maintained surroundings. Lush landscaping, graceful palm trees, and a covered front porch create a warm welcome. Inside, the foyer opens to a formal dining room with an elegant chandelier and a home office enclosed by glass French doors. Neutral tones, arched walkways, and wood laminate flooring are found throughout the main living areas. The spacious, open floor plan flows into the kitchen featuring shaker cabinets, granite countertops, a decorative backsplash, stainless steel appliances, a wine rack, and a large custom pantry with built-in storage. A dedicated laundry area with folding space adds convenience. The light-filled living room opens to a breakfast nook with a stylish rattan light fixture, bay window seating, and sliding glass doors leading to the pool. The private primary suite features double-door entry, a custom walk-in closet with extensive built-ins, and a spa-inspired bathroom with dual vanities, a large soaking tub, and a separate glass-enclosed shower. Three additional bedrooms and two full guest bathrooms with tub/shower combinations provide plenty of space for family and guests. Step outside to your own tropical retreat, complete with a screened-in pool, shaded gazebo, and vinyl fencing for added privacy. Updates include HWT 2023, HVAC 2019, and roof replacement in 2020. Conveniently located near entertainment, shopping and dining at Winter Garden Village, Walt Disney World, and major roadways including Florida's Turnpike, this home offers both comfort and accessibility. Schedule your private showing today!

5021 Carillon Lane, Windermere
8516 Danforth Drive, Windermere
$350,000
2 Beds ⋅ 3 Baths ⋅ Lakes/Windermere - Lake Reams Townhomes SubDv. ⋅ 34786 Zip Code
Live Where the Magic Happens! This beautifully maintained, FULLY FURNISHED 2-bedroom, 2.5-bath Townhome is located in the coveted Windermere area, perfectly situated just minutes from DISNEY’S BACKYARD!! A quiet placement towards the rear of the community, this unit provides peaceful views of the conservation and walking trail surrounded by majestic oak-lined streets that capture the charm and serenity of this sought-after community. Step inside to an inviting open-concept layout with tile flooring throughout the main level and a seamless flow between the Living, Dining and Kitchen areas, perfect for everyday living or entertaining. Stunningly renovated Kitchen features Granite countertops, Stainless Steel Appliances, Island, Stone Backsplash and Dinette space. Upstairs, all bedrooms provide comfort and privacy with newer carpet. The Primary Bedroom boasts a walk-in closet and ensuite Bathroom with garden tub/shower combo. The second Bedroom also features an ensuite bathroom. Relax outdoors in your private, fenced courtyard with artificial turf, the perfect spot for morning coffee or evening gatherings, leading to your detached 2-car rear entry garage. Have complete peace of mind with the big-ticket expenses that have been recently taken care of: Roof 2021, Hot Water Heater 2021, AC 2021 and new Plumbing shut off valves and main water pressure reducer valve 2024. Low HOA includes a sparkling Community Pool and walking trails throughout! Zoned for top-rated Schools and conveniently close to major Theme Parks, and fantastic Shopping and Dining in Lakeside Village and Winter Garden Village. Experience the best of Florida living: Quiet Nature, Disney Magic and Windermere Charm - all in one!

8516 Danforth Drive, Windermere
14500 Bridgewater Crossings Boulevard, Windermere
$400,000
4 Beds ⋅ 3 Baths ⋅ Tennyson Pk/Summerport SubDv. ⋅ 34786 Zip Code
Morning coffee at Foxtail, an evening walk for Kelly’s Homemade Ice Cream, and a move-in-ready home waiting when you get back. At 14500 Bridgewater Crossings Boulevard, that can be your everyday routine. Located in Windermere’s Summerport community, this 4-bedroom, 2.5-bath townhome combines a convenient neighborhood setting with fresh interior paint throughout, new luxury vinyl plank flooring upstairs, and no carpet anywhere in the home. A main-floor primary suite is a standout feature, offering the convenience of having your bedroom and private bathroom downstairs, with three additional bedrooms, a full bathroom, and a loft upstairs. Whether you need room for guests, a dedicated home office, or a second gathering space, the layout gives you options. Downstairs, the living and dining areas, kitchen, and guest half bath keep everyday activities on the main level. A courtyard provides an outdoor spot for plants, coffee outside, or unwinding at the end of the day, while a covered walkway connects the home to the two-car garage. And the neighborhood gives you plenty of reasons to step outside. Walk across the street for your favorite coffee or a scoop of ice cream, enjoy nearby Summerport Park, and appreciate the convenience of having Keene’s Crossing Elementary close by. Summerport’s community pool, clubhouse, fitness center, tennis courts, playgrounds, and walking paths make it easy to fit recreation into your routine without planning an entire day around it. Beyond the neighborhood, Publix at Cornerstone at Summerport keeps grocery runs convenient, while Winter Garden Village and Hamlin offer nearby shopping, restaurants, and entertainment. Walt Disney World is also within easy reach, whether your plans call for a full park day or a spontaneous evening out. With fresh updates already completed, a main-floor primary suite, and neighborhood favorites just a walk away, this home is ready for you to settle in and start enjoying everything beyond the front door. Schedule your private showing today.

14500 Bridgewater Crossings Boulevard, Windermere
5650 Nectarine Drive, Windermere
$1,475,000
5 Beds ⋅ 5 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code
NEWLY BUILT HOME WITH LAKE CAWOOD ACCESS ON APPROXIMATELY 1.70 ACRES! Discover refined lake living in this Ashton Woods Duval residence in Lake Cawood Cove, Windermere, with the opportunity to build your own PRIVATE BOAT DOCK. With approximately 3,612 square feet of living space, 5 BEDROOMS, 4 FULL BATHROOMS, 1 HALF BATHROOM, and a 3-CAR TANDEM GARAGE, this home combines generous space with thoughtfully selected upgrades. 10-FOOT CEILINGS ON THE FIRST FLOOR, 9-FOOT CEILINGS ON THE SECOND FLOOR, and 8-FOOT DOORS enhance the spacious feel. NEW LUXURY VINYL PLANK FLOORING extends throughout the home, including the staircase, while the bathrooms and laundry room feature tile flooring. The impressive great room features a SOARING 2-STORY CEILING, creating an open, airy atmosphere that connects seamlessly to the GOURMET KITCHEN and breakfast area. Designed for everyday enjoyment and entertaining, the kitchen features a SPACIOUS ISLAND, an upgraded appliance package, UPGRADED CABINETRY, additional storage cabinets at the back of the island, and a customized pantry layout. A separate dining room provides space for special gatherings. The FIRST-FLOOR BEDROOM SUITE includes a closet and private full bathroom, creating a comfortable retreat for guests. Upstairs, the spacious PRIMARY SUITE features a TRAY CEILING, a LARGE WALK-IN CLOSET, and a private bathroom with separate vanities and a walk-in shower. An additional bedroom suite includes its own full bathroom, while 2 more bedrooms share another full bathroom. A versatile LOFT and conveniently located laundry room complete the second floor. Carefully selected enhancements include UPGRADED BATHROOM TILE with wall tile extending to the ceiling, upgraded toilets, LIGHTING UPGRADES, and wood stair railings. Additional features include sound insulation in selected walls, FOAM INSULATION in the block walls of the living space and garage, and prewiring for ceiling fans, security, and 2 additional wireless access points. An UPGRADED FRENCH DOOR opens to the COVERED LANAI, creating an inviting connection to outdoor living. SUMMER KITCHEN PLUMBING AND ELECTRICAL PROVISIONS provide the flexibility to customize your outdoor entertaining space. A conservation area toward Lake Cawood provides a peaceful, natural backdrop. Enjoy convenient access to Windermere Preparatory School, Windermere High School, Publix, Aldi, shopping, dining, Winter Garden Village, the 429 Expressway, and world-famous theme parks. With its desirable Windermere location, stylish finishes, and spacious layout, this newly built home provides an exceptional opportunity to enjoy the Florida lifestyle. Schedule your private showing today! VIDEO, 3D TOUR, AND FLOOR PLAN LINKS ABOVE.

5650 Nectarine Drive, Windermere
11267 Grander Drive, Windermere
$435,000
3 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph 2 #35 36 SubDv. ⋅ 34786 Zip Code
Stunning modern townhome in the desirable Lake Burden community of Windermere! This beautifully designed 3-bedroom, 2.5-bathroom corner-lot townhome offers 1,743 sq ft of living space with all bedrooms upstairs, including a primary suite with walk-in closet. The modern kitchen features dark wood cabinets, granite countertops, a spacious island with room for three barstools, and slate stainless steel GE appliances. High ceilings and an open floor plan create a bright, inviting space perfect for entertaining. Two-car garage. Currently tenant-occupied with a lease through 12/31/2026 - a great opportunity for investors seeking immediate rental income, or for buyers planning ahead. Short walk to the community clubhouse with a large resort-style pool, shaded seating and picnic areas. Lake Burden is a nature lover's paradise featuring a fishing pier, a scenic lake with a mile-long walking and biking trail, outdoor fitness stations, playground and tennis courts, with trails connecting to Downtown Windermere. Zoned for Sunset Park Elementary, Horizon West Middle and Windermere High School. Short-term rentals are not permitted. Schedule your showing today!

11267 Grander Drive, Windermere
8867 Herencia Alley, Windermere
$405,000
3 Beds ⋅ 3 Baths ⋅ Legado SubDv. ⋅ 34786 Zip Code
Welcome to this beautiful townhome in the desirable Legato community in Windermere! This spacious 3-bedroom, 2.5-bathroom home features an open floor plan and a 2-car garage, offering comfort, functionality, and convenience. Enjoy the community swimming pool and a prime location near Walt Disney World, shopping centers, restaurants, and everyday amenities. The property is currently vacant and ready for its next owner. With HOA allowing long-term rentals, this home presents an excellent opportunity for both owner-occupants and investors seeking a rental property in a desirable location. Don’t miss this opportunity!

8867 Herencia Alley, Windermere
8276 Maritime Flag St Unit 1204, Windermere
$324,900
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lk/Windermere Ph 12 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combination of location, comfort, and investment potential, this property is an excellent opportunity for both homeowners and investors looking for a rental property in the heart of Central Florida. Conveniently located near Walt Disney World, Windermere, shopping, restaurants, and major roadways including I-4 and the 429, this condo offers easy access to the area's top attractions, employment centers, and everyday conveniences. Its location also makes it an appealing option for renters seeking proximity to Disney, the Windermere area, and nearby schools. Inside, you'll find a functional open-concept split floor plan with quality laminate flooring throughout. The kitchen features beautiful wood cabinetry, granite countertops, modern appliances, and plenty of counter space. The spacious dining area and great room create an inviting setting for entertaining family and friends. The generously sized primary bedroom accommodates a king-size bedroom suite and features a walk-in closet. The primary bathroom includes dual sinks, ample cabinetry, and a bathtub/shower combination. Two additional bedrooms are situated on the opposite side of the condo, conveniently located near the second full bathroom and laundry closet. Step through the sliding glass doors to enjoy your private screened-in patio, perfect for relaxing and enjoying Florida's year-round outdoor lifestyle. Residents enjoy a variety of community amenities, including a gated entrance, valet trash service, a beautiful clubhouse, a resort-style destination pool, a sand volleyball court, and a barbecue area. An Excellent Investment Opportunity you don't want to miss!!

8276 Maritime Flag St Unit 1204, Windermere
5944 Caymus Loop, Windermere
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
AVAILABLE FOR SALE OR LEASE. Keene's Pointe, 24-hour gated/attended golf community. Tucked adjacent to the Butler Chain of Lakes this home offers 4 bedrooms, 3 baths, formal living and dining and an office/den. As you enter this one level home you will find 3-way split functional plan. Boasting the primary ensuite separate from the three additional bedrooms with a spacious bath and TWO WALK-IN CLOSETS, and access to the covered/screened lanai. Spacious kitchen with an abundance of cabinetry, convenient desk area and island. Newer stainless Steel appliances. The kitchen, dinette and great room feature two sets of French doors that give way to the covered screened lanai and back yard. Beyond the screened lanai is an oversized paved patio and custom pergola seating. Privacy is included with the 6 ft vinyl fence. New Roof ('20), AC units(’18/’19), Hot Water Heater (’21/Natural Gas), Exterior Paint(’20) Shallow well for irrigation, termite bond, 5 Camera Ring System (8/21) including Flood lights and doorbell, expanded paver driveway (2025) for additional parking, blinds and plantation shutters, central vacuum system, and new septic pump('22) are just a few of the great features of this home. Located close to dining, shopping, expressways, tourist attractions, and top-rated public and private schools, this home and community has it all!

5944 Caymus Loop, Windermere
12785 Westside Village Loop, Windermere
$769,000
4 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code
NEW PRICE! MOVE-IN READY WINDERMERE HOME WITH PEACEFUL CONSERVATION VIEWS + $12,000 DECOR/RATE BUY DOWN CREDIT! Discover the perfect blend of comfort, style, and location in desirable Westside Village! This beautifully maintained 4-bedroom, 3.5-bath home features an inviting open-concept floor plan, classic tile roof, professionally landscaped yard, and spacious front porch. Enjoy tranquil conservation views from the backyard, creating a peaceful backdrop for relaxing or entertaining. The light-filled kitchen is designed for everyday living and effortless entertaining, featuring granite countertops, stainless steel appliances, and an oversized center island with abundant storage and seating. The kitchen flows seamlessly into the living room and breakfast nook, while French doors open to the patio for easy indoor-outdoor living. Enjoy a $12,000 decor credit toward a flooring upgrade and EV charger, offering an opportunity to personalize your home and add modern convenience. Westside Village offers an exceptional lifestyle with resort-style amenities, including a community pool, clubhouse, playground, paved walking trails, and scenic water features. Conveniently located near top-rated schools, shopping, dining, major highways, and just minutes from Walt Disney World, this home combines peaceful surroundings with easy access to everything Central Florida has to offer.

12785 Westside Village Loop, Windermere
11963 Vermillion Avenue, Windermere
$430,000
3 Beds ⋅ 3 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Virtually Staged. LOCATION, LOCATION, LOCATION! Welcome to Windermere Trails, one of Windermere’s most desirable communities. This beautiful 3-bedroom, 2.5-bath townhome offers 1,676 sq. ft. of living space, a 2-car garage, and an unbeatable location just steps from Bay Lake Elementary School. Enjoy the convenience of having shopping, dining, and everyday essentials nearby, including Publix at Lakeside Village, while being just minutes from Walt Disney World and major roadways. The home features an open and functional floor plan, stainless steel appliances, ceramic tile throughout the first floor, and spacious living areas designed for comfortable everyday living. Windermere Trails offers resort-style community amenities including a pool, splash pad, playground, dog park, open-air pavilion, walking areas, and beautiful green spaces. Exceptional Windermere location, convenient access to highly regarded area schools, shopping, dining, entertainment, and everything the Horizon West area has to offer. Schedule your showing today!

11963 Vermillion Avenue, Windermere
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