Windermere Homes with Association Recreation - Owned Community Features

Windermere Homes with Association Recreation - Owned Community Features

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County that beautifully blends small-town charm with modern conveniences. Known for its stunning lakes, lush landscapes, and serene atmosphere, Windermere offers residents a unique lifestyle that feels both tranquil and vibrant. With its close-knit community feel and friendly neighbors, it’s no wonder why so many families and individuals choose to call this enchanting town home.

Windermere is renowned for its stunning homes, many of which are located within association-managed communities. These homes boast a variety of architectural styles and are designed to cater to diverse tastes and lifestyles. One of the standout features of living in these communities is access to exceptional recreational amenities. Residents can enjoy beautifully maintained parks, sparkling swimming pools, and state-of-the-art fitness centers, all within the comfort of their neighborhood. Whether you prefer a leisurely afternoon by the pool, a morning jog on scenic trails, or engaging in friendly matches at tennis courts, these community features enhance the quality of life for Windermere residents.

In addition to recreational opportunities, Windermere is conveniently located near top-rated schools, shopping centers, and dining options, making it easy to enjoy everything this charming town has to offer. With its stunning natural beauty, welcoming community, and abundant amenities, Windermere is not just a place to live – it’s a place to thrive. Discover your dream home in this idyllic Florida town and experience the perfect blend of relaxation and recreation. Welcome to Windermere, where your new chapter awaits!

Newest Windermere Homes with Association Recreation - Owned Community Features

$1,305,741
6 Beds ⋅ 5 Baths ⋅ Palms At Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. Under Construction. SWEETWATER H - Our beautiful huge 2 story home, located on a conservation lot, with 6 Bedrooms and 4.5 Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. The living area has an extension to the room, 9' hidden sliding glass doors and a huge lanai that runs the width of the home. Downstairs flex room works well as an office or study. Upstairs, find 5 large bedrooms most with walk in closets, 3 full baths, and a second laundry room,(that's right! 1 upstairs, and 1 downstairs). Common areas upstairs include a spacious bonus room with wet bar, and a second flex room that works well as a theatre room. SAMPLE IMAGES

14213 Crest Palm Avenue, Windermere
$4,495,000
4 Beds ⋅ 7 Baths ⋅ Keenes Pointe 46/104 SubDv. ⋅ 34786 Zip Code
Experience refined luxury in this extraordinary custom estate overlooking the 17th tee of the Jack Nicklaus Signature Golden Bear Club, nestled within the prestigious guard-gated community of Keene’s Pointe in Windermere. Completely reimagined with exceptional attention to detail, this residence seamlessly blends timeless architecture with sophisticated contemporary design. From the moment you enter, soaring ceilings accented by exposed wood beams, expansive porcelain flooring, designer lighting, custom millwork, and walls of glass create an atmosphere of understated elegance and warmth. Designed for both everyday living and grand-scale entertaining, the impressive great room is anchored by a striking floor-to-ceiling porcelain fireplace with custom illuminated built-ins. The gourmet kitchen is beautifully appointed with premium Viking appliances, custom European-style cabinetry, quartz countertops, an oversized center island, and a separate catering kitchen that makes hosting effortless. The luxurious primary suite offers a peaceful private retreat featuring custom-designed walk-in closets and a spa-inspired bath with dual vanities, a freestanding soaking tub, a walk-in shower, and exceptional designer finishes throughout. Spacious guest suites provide comfort and privacy for family and visitors alike. One of the home’s most remarkable features is the expansive climate-controlled lanai, thoughtfully designed as a true extension of the interior living space. Complete with a fully equipped summer kitchen, multiple gathering areas, and panoramic golf course views, it offers the perfect setting for year-round indoor-outdoor living and unforgettable entertaining. One of the very few homes on Valhalla Drive to feature a four-car garage, this residence provides exceptional space for automobiles, golf carts, and additional storage. The pool and spa overlook the beautifully manicured fairways, creating a tranquil backdrop that captures the beauty and serenity of one of Central Florida’s premier private golf communities. Located in one of Windermere’s most sought-after addresses, Keene’s Pointe offers 24-hour guarded security, picturesque tree-lined streets, and an exceptional lifestyle centered around the renowned Golden Bear Club. Residents enjoy convenient access to top-rated schools, upscale shopping, fine dining, world-class attractions, and Orlando International Airport. This is more than a luxury home. It is an exceptional opportunity to own a beautifully renovated residence in one of Windermere’s most distinguished private golf communities.

6719 Valhalla Way, Windermere
$325,000
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Virtually Staged. Imagine coming home to a resort-style community just minutes from Walt Disney World! This beautiful 3 Bed + 2 Bath top-floor unit is located in the highly sought-after Horizon West area of Windermere, where comfort, convenience, and an exceptional location come together. Perfectly situated directly across from the clubhouse with easy elevator access, this bright and spacious home offers relaxing views from the private screened balcony overlooking the community's extensive amenities. The open, split floor plan features tile flooring throughout the main living areas, carpet in the bedrooms, and gorgeous crown molding. The lovely kitchen has granite countertops, 42" maple cabinetry, quality appliances, upgraded fixtures, and a large walk-in pantry. Lakeside's amenities include two resort-style pools, fitness center, volleyball courts, and a spacious clubhouse. Located just minutes from Disney, Lake Side Shoppes, Hamlin Town Center, tons of restaurants and top-rated schools! Call today to schedule a viewing!

8168 Boat Hook Loop Unit 724, Windermere
$1,075,000
4 Beds ⋅ 3 Baths ⋅ Willows At Lake Rhea SubDv. ⋅ 34786 Zip Code
In Windermere homes can be renovated. Locations like this cannot be recreated. Set on more than half an acre with tranquil water views and exceptional privacy, this beautifully renovated residence offers a lifestyle that’s increasingly difficult to find. Spend weekends boating on the Butler Chain of Lakes, enjoying a match of tennis or pickleball, or unwinding by your private pool as peaceful water views become the backdrop to everyday life. Just a golf cart ride from downtown Windermere’s beloved Farmers Market, waterfront parks, dining, and community events—and with Windermere Elementary and many of Central Florida’s premier public and private schools nearby—this is a home that blends convenience with an unmatched sense of place. Inside, thoughtfully reimagined interiors pair contemporary finishes with effortless livability, creating a turnkey home where the lifestyle is every bit as compelling as the home itself. Residents of The Willows enjoy an outstanding lifestyle with neighborhood amenities including walking trails, a playground, volleyball, basketball, tennis, and pickleball courts. Windermere Elementary is within walking distance and Windermere High School and many premier private schools close by. Extensively renovated with today's most sought after finishes and design elements and designed for both everyday living and elegant entertaining, the spacious floor plan features four bedrooms and three baths. The private owner's retreat is a true sanctuary, offering direct access to the pool area and peaceful water views. A grand dining room with soaring 12-foot vaulted ceilings creates a sophisticated setting for gatherings, while the inviting living room showcases beautiful outdoor vistas. At the heart of the home, the gourmet kitchen flows seamlessly into the breakfast nook and family room, creating an open and welcoming space that extends to the covered lanai and pool area. Whether hosting guests or enjoying a quiet evening at home, the indoor/outdoor connection embodies the very best of Florida living. The thoughtfully designed split bedroom layout provides privacy and functionality, with two secondary bedrooms with walk-in closets, charming window seats with built-in storage are connected by a Jack and Jill bath. A dedicated laundry room, and abundant storage throughout add to the home's exceptional livability. Additional highlights include a central vacuum system, three-car side-entry garage, and circular driveway with ample guest parking. Convenient access to major roadways, shopping, healthcare, golf, Orlando International Airport, and world-famous attractions further enhances the appeal. Offering an unparalleled combination of location, luxury, recent renovations, and lifestyle, this remarkable property presents a rare opportunity to own one of Windermere's most desirable homes. Schedule your private showing today!

11217 Willow Gardens Drive, Windermere
$755,000
4 Beds ⋅ 4 Baths ⋅ Ashlin Park Ph 2 SubDv. ⋅ 34786 Zip Code
***PRICE IMPROVEMENT***Welcome to this stunning FORMER MODEL HOME in the sought-after ASLIN PARK, a community in the heart of WINDERMERE. This former CUSTOM CARLISLE model was designed and built by renowned ASHTON HOMES. Perfectly positioned on a premium corner lot with not rear neighbor and pond view, located in one of Windermere desired subdivision. This exceptional former model home blends timeless architecture, upscale finishes, and a thoughtfully designed floor plan tailored for both refined entertaining and comfortable everyday living. Surrounded by tranquil lakes, beautifully manicured streets, and a picturesque neighborhood setting, the home offers an impressive sense of arrival, beginning with its inviting covered front porch and attractive curb appeal. Inside, a welcoming foyer introduces gracious formal living and dining spaces that create an elegant backdrop for gatherings, celebrations, or quiet evenings at home. Just beyond, the sunlit family room serves as the heart of the residence, featuring soaring 20-foot wood ceilings that add warmth, character, and dramatic visual impact while seamlessly connecting to the gourmet kitchen. Designed with both beauty and functionality in mind, the kitchen is appointed with an expansive quartz island with double sinks, premium stainless-steel appliances, abundant custom cabinetry, generous workspace, and convenient access to the powder room and attached two-car garage, making daily routines and entertaining effortless. A striking wood staircase with an iron handrail enhances the home’s architectural appeal and leads to the second level, where the layout continues to provide comfort, privacy, and versatility for a variety of living needs. The private primary suite serves as a relaxing retreat, complete with a custom walk-in closet and a spa-inspired bath featuring dual sinks and a separate shower. Two well-appointed secondary bedrooms share a spacious Jack & Jill bathroom with a garden tub, while the junior suite offers its own private full bath with a walk-in shower, ideal for guests, multigenerational living, or anyone seeking additional privacy. A flexible bonus room provides space for a media room, playroom, office, or lounge, and the centrally located laundry room adds everyday convenience. Outdoors, the peaceful backyard extends the living space with a private tree-lined deck that creates a serene setting for al-Fresco dining, weekend entertaining, or unwinding in the shade after a long day. Spanning 3,161 square feet, the residence is enriched with upscale details throughout, including quartz countertops, generous walk-in closets, refined interior finishes, and a wired security system that adds peace of mind. An attached private Studio further enhances the home’s versatility, offering a comfortable and separate space for extended family, In-Laws, long-term guests, or roommates, with its own distinct access through the main entrance while remaining connected to the property. Beyond the home itself, residents enjoy access to top-rated schools and an impressive selection of community amenities, including a resort-style pool, clubhouse, playgrounds, and scenic walking and biking trails that wind around picturesque ponds and lakes, creating a lifestyle that is as desirable as the home itself. Just few miles to Disney Spring and amusement attractions. Don't miss the opportunity to own this gem perfectly located in the desired Ashlin Park community!!

7211 Still Pond Lane, Windermere
$699,000
5 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 05 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Enjoy exceptional privacy with beautiful conservation views behind & expansive green space beside the home, creating a peaceful setting rarely found in the community. Tucked away on a desirable homesite, 7906 Jailene Drive offers 2,618 SF, 5 bedrooms, 3 full bathrooms, 2-car garage, all filled with thoughtfully designed living spaces & ample dedicated guest parking conveniently located nearby. A welcoming front porch sets the tone as you enter the home, where a custom wood accent wall in the foyer creates a warm and inviting first impression. The open-concept layout offers spacious living & dining areas that flow seamlessly into the kitchen & family room. A dramatic two-story ceiling in the family room fills the space with natural light creating an impressive sense of openness, making it the perfect place to gather & entertain. The kitchen features granite stone countertops, abundant solid wood cabinetry, ample prep space, a kitchenette area & a functional layout overlooking the main living areas. Fresh interior paint, luxury vinyl flooring throughout & charming designer light fixtures add style and warmth throughout the home. The versatile floor plan includes a first-floor study/den which can also be used as a 5th bedroom with full bathroom. This space is ideal for a home office, family, guests, or multi-generational living. Upstairs, you’ll find four additional bedrooms, including the spacious primary suite, along with two full bathrooms & a conveniently located laundry room. Step outside to the screened lanai with tranquil conservation views, embracing nature at its best with exceptional privacy. Enhanced by a hand-painted decorative concrete finish, this outdoor retreat provides the perfect space for morning coffee, outdoor dining, or relaxing evenings, especially with a fully-fenced backyard. Located in the highly desirable Lake Sawyer community, residents enjoy access to a community pool, playground, park, and scenic sidewalks throughout the neighborhood. The home is zoned for sought-after schools, including Sunset Park Elementary, Horizon West Middle School, and Windermere High School. Just minutes from Horizon West and Hamlin Town Center, you’ll enjoy convenient access to shopping, dining, entertainment, and everyday conveniences. Major roadways are nearby, providing easy access to Walt Disney World, Disney Springs, downtown Orlando, Orlando International Airport, and all that Central Florida has to give. Combining privacy, functionality, thoughtful updates, and an exceptional location, this move-in-ready home presents a rare opportunity in one of Windermere’s most sought-after communities. Additional highlights include a brand-new roof (June 2026), HVAC 2024, abundant storage & a desirable location close to shopping, dining, schools, & major roadways. Combining privacy, functionality, & modern updates, this move-in-ready home is ready to welcome its next owners!

7906 Jailene Drive, Windermere
$2,195,000
4 Beds ⋅ 4 Baths ⋅ Kelso On Lake Butler SubDv. ⋅ 34786 Zip Code
Opportunities like this in Windermere rarely reach the open market and are often treasured for generations.Welcome to an extraordinary lakefront estate in the highly coveted community of Kelso on Lake Butler, where timeless architecture, unmatched privacy and the ultimate Florida lifestyle come together on over 2 pristine acres along the shores of private Lake Davis. This sprawling custom one-story estate offers almost 4000 square feet of thoughtfully designed living space with breathtaking sunset views, a private sandy shoreline,private boat ramp and covered boat dock on Lake Davis. Residents of Kelso on Lake Butler also enjoy exclusive access to a private community boat ramp, fishing pier and park on the world-renowned Butler Chain of Lakes,connecting you to 13 interconnected ski lakes and more than 5,000 acres of recreational paradise just moments from your front door. From the moment you arrive, the heavily landscaped grounds,massive brick paver driveway,lush tropical landscaping & mature oak trees create a commanding first impression.Oversized double entry doors open to soaring 14-foot ceilings and an incredible open-concept living space designed for both grand entertaining and everyday comfort.The impressive great room (34x25) is anchored by a dramatic wall of custom built-ins, stunning stonework and an electric fireplace that creates an incredible focal point. The chef’s kitchen is equally spectacular,featuring an oversized gathering island,separate Sub-Zero refrigerator and freezer,custom cabinetry and a showstopping Wolf freestanding range,vented hood and pot filler.This space was designed to bring people together and will quickly become the centerpiece of every gathering. The owner’s retreat is a true private sanctuary , massive custom walk-in closet with additional full sized W & D, massive spa and secluded outdoor shower. On the opposite side of the home, a bonus/flex room leads to an additional ensuite bedroom and two oversized secondary bedrooms connected by a Jack and Jill bath provide exceptional privacy and flexibility for family and guests. A secondary garage exit also allows this area to easily be converted into an in law suite. One of the home’s most captivating features is the massive pocketing glass wall that completely opens the interior to the enormous covered & screened lanai, creating a seamless indoor-outdoor living experience. Tongue & groove ceilings,a summer kitchen and panoramic lake views transform this space into the ultimate entertaining destination.Every evening feels special as you enjoy postcard-worthy sunsets over Lake Davis from the comfort of your own backyard. Additional highlights include a climate-controlled garage,irrigation sourced directly from the lake for reduced waterbill &a durable metal roof designed for decades of drama free ownership. Kelso on Lake Butler is one of Windermere’s most sought-after luxury lakefront communities,known for its canopy oak-lined streets,estate homes and unmatched access to the Butler Chain of Lakes.Tucked away in one of Windermere’s best-kept secrets,yet only minutes from top-rated schools, dining, shopping and major attractions,this location perfectly balances tranquility and convenience. This is more than a home,it is a rare legacy property and a true unicorn opportunity in the Windermere luxury real estate market. Opportunities like this are few and far between.Do not miss your chance to own one of Central Florida’s most special lakefront estates.

5624 W Lake Butler Road, Windermere
$299,500
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks SubDv. ⋅ 34786 Zip Code
Discover comfort and convenience in this well-appointed first-floor condo located in the heart of Windermere. Unit 109 offers a functional split-bedroom layout with inviting living spaces, generous natural light, and easy ground-level access. The kitchen opens seamlessly to the main living area, creating a welcoming flow that works equally well for everyday living or entertaining guests. The primary suite features a spacious walk-in closet and private bath, while the additional bedrooms provide flexibility for guests, a home office, or family living. Step outside to enjoy the covered patio — a perfect spot for morning coffee or winding down at the end of the day. Situated within a gated community with resort-style amenities, residents enjoy access to a pool, fitness center, playground, walking areas, and more. Conveniently located near shopping, dining, major roadways, and Central Florida attractions, this property combines low-maintenance living with an unbeatable location.

8180 Boat Hook Loop Unit 109, Windermere
$940,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene's Pointe - 24-hour gated/attended community in Windermere, Florida. 4 bedroom/3 bath home with formal living and dining rooms, kitchen and great room. This quaint home features a functional floor plan. Kitchen with newer stainless appliances, open concept floor plan joining the kitchen, nook and great room and private primary with walk-in closet and bath with dual vanities, shower and garden tub. Enjoy peaceful evenings in the private back yard with spacious lanai, screened oversized pool and large yard. The fourth bedroom is currently being used as a den with French doors. NEW ROOF IN 2022, WATER HEATER 2020, two car garage with storage, and much more. Discover all this community has to offer, including The Golden Bear Club, a private 18-hole golf course designed by Jack Nicklaus offering golf, tennis, swimming, dining and clubhouse. Located close to shopping, dining, expressways and top-rated public and private schools, this home is perfect as a primary home or vacation home. Call today for you private viewing.

8525 Bowden Way, Windermere
$510,000
3 Beds ⋅ 3 Baths ⋅ Lakes Windermere Ph 01 49 108 SubDv. ⋅ 34786 Zip Code
Price Reduced 10K for a quick sale. Seller very Motivated ! Welcome to this stunning 2-story home in the highly desirable Lakes of Windermere, featuring 3 bedrooms, 2.5 bathrooms, and a spacious bonus room that can easily serve as a home office, gym, media room, or playroom. The expansive primary suite offers soaring vaulted ceilings, a large walk-in closet, and a spa-inspired in-suite bathroom with a relaxing jacuzzi tub. Upstairs, you'll find beautiful wood flooring throughout—no carpet—along with elegant plantation shutters that add warmth and timeless style to every room. Thoughtfully updated for comfort and peace of mind, this home features impact windows, stainless steel appliances, Laundry room with washer and dryer, and ceiling fans in both the living room and primary suite. Step outside to your private, fully fenced backyard—perfect for entertaining, family gatherings, or simply relaxing. Enjoy a mature mango tree, a charming pergola, and an irrigation system using reclaimed water to keep the landscaping lush while conserving resources. The extended rear driveway with alley access provides generous guest parking, while the 2-car garage offers epoxy flooring, built-in storage cabinets, an extra refrigerator, and a new garage door opener for added convenience. Located in the sought-after Lakes of Windermere community, residents enjoy beautifully maintained parks, Gazebo, scenic lake Sawyer View, playgrounds, and a Community Recreation Area with pool, tennis, volleyball and basketball. Nestled House on a quiet single-entry loop surrounded by elegant homes, this property is just minutes from shopping, dining, top-rated schools, Disney, and major roadways.

6820 Thornhill Circle, Windermere
$4,300,000
3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Experience refined luxury living in this extraordinary 5,004-square-foot garden villa estate nestled within Isleworth Golf & Country Club. This impeccably designed residence offers three expansive bedrooms, each with its own beautifully appointed en-suite bathroom, along with two elegant half baths to accommodate guests with ease. From the moment you arrive, the home’s striking Mediterranean-inspired architecture, circular tower entry, and meticulously landscaped grounds set the tone for the sophistication that awaits inside. Step through the grand entrance into interiors defined by soaring ceilings, abundant natural light, and exquisite craftsmanship at every turn. The gourmet kitchen serves as the heart of the home, showcasing custom cabinetry, premium Sub-Zero appliances, an oversized center island, and designer finishes that seamlessly blend form and function—perfect for both intimate family moments and upscale entertaining. Flowing effortlessly into the main living areas, the open-concept layout creates a warm yet refined atmosphere, enhanced by elegant lighting, stone flooring, and thoughtful architectural details throughout. Retreat to the luxurious primary suite, a private sanctuary featuring a spa-inspired bathroom with soaking tub, walk-in shower, dual vanities, and custom finishes that evoke a five-star resort experience. Each additional bedroom offers generous proportions, privacy, ensuring comfort and convenience for family members and guests alike. The inclusion of two half bathrooms further elevates the home’s functionality for entertaining. The outdoor living spaces are equally impressive, offering the perfect backdrop for enjoying Florida’s year-round sunshine. Whether hosting gatherings or savoring quiet evenings, the seamless indoor-outdoor connection enhances the overall living experience. Located within the exclusive Isleworth community—renowned for its world-class golf, privacy, and unparalleled lifestyle, this residence presents a rare opportunity to own a home that embodies elegance, comfort, and timeless design in one of Central Florida’s most sought-after communities while being close to shopping, world class dining and attractions.

9144 Isleworth Gardens Drive, Windermere
$559,000
4 Beds ⋅ 3 Baths ⋅ Summerport Ph 5 SubDv. ⋅ 34786 Zip Code
Welcome to your new forever home in Summerport! This beautifully designed 4-bedroom, 3-bath home offers 2,411 square feet of spacious living with stunning golf course views and no rear neighbors, creating a sense of privacy that’s hard to find. A manicured front lawn welcomes you in, while inside, long hallways with tray ceilings and arched doorways set an elegant tone from the moment you enter. The heart of the home opens into a bright, open-concept living, dining, and kitchen space designed for effortless entertaining and easy every day living. The kitchen is truly expansive, featuring an oversized island, abundant counter space, built-in wine storage, crown-molded cabinetry, stainless steel appliances, and recessed lighting throughout. Overlooking the main living area, it’s a space that keeps everyone connected, whether hosting guests or enjoying a quiet night in. The primary suite makes a statement with double-door entry, high ceilings, and a spacious layout that feels like a true retreat. The en suite bathroom offers dual separate vanities, a large walk-in shower, and a beautiful garden tub, making it perfect for unwinding at the end of the day. Additional bedrooms provide flexibility for family, guests, or a home office, each offering comfort, natural light, and ample space. Step outside to a fully fenced backyard where four legged friends and little ones can roam freely, all while enjoying peaceful golf course views with no rear neighbors behind you. Roof replaced in 2022, A/C replaced in 2020 giving a peace of mind to the new owner. The community adds even more to love, featuring a clubhouse, resort-style pool, fitness center, playgrounds, tennis courts, and basketball courts, offering something for everyone just steps from home. Conveniently located near Hamlin Town Center, you’ll have easy access to top shopping, dining, and highly rated schools, with major attractions like Walt Disney World and Universal Studios just 20 minutes away. Don't miss out on this stunning home in an ideal location, schedule your private showing TODAY!!!

4627 Blue Major Drive, Windermere
Start Your Search