Windermere Homes with Traditional Architectural style

Windermere Homes with Traditional Architectural style

Welcome to Windermere, Florida—a picturesque town nestled in Orange County that perfectly blends small-town charm with modern convenience. Known for its stunning lakes and lush landscapes, Windermere offers a serene escape from the hustle and bustle of city life, making it an ideal location for families and professionals alike.

Windermere is renowned for its traditional architectural style homes, which reflect the timeless elegance of Southern living. These exquisite residences often feature classic elements such as gabled roofs, brick facades, and spacious porches that invite you to relax and enjoy the warm Florida sunshine. With an emphasis on craftsmanship and detail, many of these homes are designed to create a welcoming atmosphere, perfect for hosting gatherings or enjoying quiet evenings with family.

As you stroll through the tree-lined streets of Windermere, you’ll discover a vibrant community that values its history while embracing a forward-thinking vision. The town boasts an array of recreational activities, from boating and fishing on the pristine Butler Chain of Lakes to exploring the local parks and trails. The close-knit community hosts various events throughout the year, fostering connections among residents and creating a sense of belonging.

Windermere is also conveniently located near major highways, making it easy to access nearby attractions, shopping centers, and dining options. Whether you’re seeking a family home or a tranquil retreat, Windermere’s traditional homes offer the perfect blend of comfort, style, and community spirit. Come and experience the charm of Windermere—where your dream home awaits!

Newest Windermere Homes with Traditional Architectural style

$3,100,000
6 Beds ⋅ 5 Baths ⋅ Lake Hancock Shores SubDv. ⋅ 34786 Zip Code
Virtually Staged. Luxury Lakefront Living with No HOA on an Oversized Lot! Welcome to this exceptional 6-bedroom lakefront estate situated on an oversized lot with no HOA and an oversized 3-car garage. Recently and completely updated, this stunning home showcases designer finishes throughout, offering the perfect blend of luxury, comfort, and modern style. 12 FOOT CEILING IN LIVING AREA WITH 10 FT CEILINGS IN BEDROOMS Recent improvements include new flooring throughout, a beautifully remodeled kitchen, a designer backsplash, and updated finishes. Every bathroom has been completely renovated with new sinks, showers, toilets, and designer tile extending from floor to ceiling. The home has also been freshly painted inside and out, complemented by new designer light fixtures and custom closet systems, creating a truly move-in-ready home. At the heart of the home is the spacious kitchen overlooking the expansive family room. The kitchen features an oversized walk-in pantry complete with a full-size refrigerator, coffee bar, abundant storage, and a sunny breakfast area, making it ideal for everyday living and entertaining. The oversized family room is filled with natural light and features French doors that open to the covered lanai, resort-style pool, and picturesque lake. Just beyond, the impressive bonus room is the ultimate entertainment space, offering plenty of room for a pool table, golf simulator, or game room. A custom wet bar makes hosting family and friends effortless. The elegant formal dining room also features French doors leading to the covered patio, creating seamless indoor-outdoor living while enjoying beautiful lake views. A private office or den is located at the front of the home. Conveniently positioned across from a full pool bath, this flexible space can easily serve as a 6th bedroom, guest suite, or home office. As you enter, you’ll immediately notice the soaring ceilings, open floor plan, and breathtaking views that draw your eyes toward the pool and lake. The thoughtfully designed split-bedroom floor plan provides exceptional privacy for the luxurious primary suite. The spacious primary retreat features large windows overlooking the pool and lake, along with French doors providing private access to the lanai. A custom walk-through closet leads into the spa-inspired en-suite featuring dual vanities, a dedicated makeup area, a soaking tub, and an oversized walk-in shower with designer finishes. The 5th bedroom is currently being enjoyed as a relaxing yoga studio and features an oversized closet, making it a versatile space for fitness, hobbies, or guests. Bedrooms 3rd and 4th are connected by a Jack-and-Jill bathroom, while the oversized second bedroom serves as a true secondary primary suite with a large walk-in closet and a beautifully remodeled en-suite bath featuring designer tile from floor to ceiling and a spacious walk-in shower. Step outside to your private backyard retreat where the covered lanai, sparkling pool, and peaceful lake views provide the perfect setting for relaxing or entertaining. With no HOA, an oversized homesite, premium updates throughout, and an ideal layout for large families or multigenerational living, this extraordinary lakefront property offers luxury living at its finest. Cruise over and enjoy the spectacular Disney fireworks from the comfort of your own boat.

7720 Ficquette Road, Windermere
$979,500
3 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Luxury Pool Home in the Keene’s Pointe Golf Community – Windermere Nestled within the highly sought-after Keene’s Pointe golf community in the charming Town of Windermere, this beautifully maintained luxury pool home offers an exceptional blend of elegance, comfort, and timeless design. Just moments from the renowned Golden Bear Club and convenient to the Butler Chain of Lakes, this residence places you in the heart of one of Central Florida’s premier lifestyle communities, with nearby golf, boating, fine dining, boutique shopping, and the popular Windermere Farmers Market. From the moment you arrive, you’ll appreciate the mature landscaping, newly paved driveway, and outstanding curb appeal. Throughout the neighborhood, beautifully maintained parks, gazebos, playgrounds, walking areas, and manicured common spaces create a welcoming atmosphere that makes Keene’s Pointe one of Windermere’s most desirable addresses. Inside, elevated tray and coffered ceilings, designer lighting, and expansive transom windows fill the home with abundant natural light while creating a spacious, streamline feel. Custom window treatments, built-in features, and premium finishes are showcased throughout. The private office is beautifully appointed with custom built-in cabinetry, custom blinds, tray ceiling, recessed lighting, and an elegant designer fixture, creating the perfect work-from-home environment. Designed for entertaining, the gourmet chef’s kitchen is truly the centerpiece of the home. The magnificent oversized island—one of the largest you’ll find—offers exceptional prep and gathering space and includes a prep sink, recessed microwave, designer lighting, and custom wine bar. High-end custom cabinetry, a spacious pantry, farmhouse sink, stainless steel dishwasher, GE Monogram refrigerator and freezer, double Thermador ovens, and a six-burner Thermador gas range complete this exceptional culinary space. The adjoining family room showcases stunning coffered ceilings, a custom built-in media center, hand-blown designer light fixture, Infinity surround sound speakers, and custom draperies, creating an inviting space for relaxing or entertaining. The luxurious primary suite features tray ceilings, custom designer draperies, surround sound speakers, a spa-inspired bath with dual granite vanities, premium fixtures, an oversized glass-enclosed walk-in shower, private water closet, and an impressive customized walk-in closet. Guests will appreciate the beautifully finished secondary bedrooms and baths featuring granite countertops, quality fixtures, designer finishes, and a convenient pool bath with direct outdoor access. Step outside to your own private tropical retreat. The covered lanai overlooks a stunning lagoon-style swimming pool complete with a recessed fountain, Bose outdoor speakers, ceramic tile flooring, and screened enclosure—perfect for year-round Florida living. The lanai also provides convenient access to both the pool bath and the primary suite. Additional highlights include impact-resistant double-pane windows, expansive sliding glass doors with transom windows overlooking the pool, designer fixtures throughout, built-in office furniture, custom media center, surround sound systems, and exceptional attention to detail. Offering luxury, quality craftsmanship, and an unparalleled lifestyle, this exceptional Windermere pool home is a rare opportunity to own in one of Central Florida’s premier golf course communities.

11462 Claymont Circle, Windermere
$644,900
4 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere Ph 2a SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautifully maintained 2,683-square-foot home located in the highly desirable Lakes of Windermere community! Offering the perfect blend of comfort, functionality, and Florida living, this spacious residence features an open-concept floor plan designed for both everyday living and entertaining. Thoughtfully updated for peace of mind, the home features a roof installed approximately five years ago, a new pool motor and filter, and a new water heater installed just two years ago. Inside, you'll find laminate flooring and ceramic tile throughout, along with beautifully upgraded secondary bathrooms that add style and modern appeal. Step outside to your own private backyard oasis, complete with a sparkling pool and peaceful scenic views, creating the perfect setting to relax or entertain family and friends. Residents of Lakes of Windermere enjoy low HOA fees and an exceptional array of amenities, including a clubhouse just steps from the home, tennis, basketball, volleyball, and soccer courts, three playgrounds, a lake dock with fishing access, and scenic walking trails perfect for your daily stroll. Ideally located near top-rated schools, shopping, dining, and everyday conveniences, this home is just minutes from Walt Disney World, Horizon West, Winter Garden Village, and major highways, providing easy access to everything Central Florida has to offer. Whether you're searching for your forever home or an excellent investment opportunity, this move-in-ready property offers exceptional value in one of Windermere's most sought-after communities. Schedule your private showing today and experience all that this beautiful home has to offer!

12830 Cragside Lane, Windermere
$1,049,000
3 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Timeless Charm in the Heart of Downtown Windermere. Nestled beneath a canopy of majestic oak trees on one of Windermere’s most picturesque streets, this beautifully maintained three bedroom, two and half bath residence offers the perfect blend of classic Florida charm and modern comfort. Situated on a spacious 0.38 acre fenced homesite, this exceptional property features 2,795 square feet of living space and 4,163 total square feet, providing plenty of room to live, work, and entertain. From the moment you arrive, you will appreciate the peaceful setting and inviting curb appeal that make Oakdale Street one of the town’s most desirable locations. Inside, thoughtful craftsmanship is evident throughout with custom trim work, rich stone and wood flooring, double pane windows and doors, and a warm family room centered around a natural gas fireplace. The well appointed kitchen features a natural gas range, while the expansive air conditioned Florida room offers the perfect place to relax year round as you overlook the private backyard. Car enthusiasts, hobbyists, and those needing extra space will love the 4 car garage along with the detached air conditioned building, ideal as a home office, fitness studio, art studio, workshop, guest retreat, or whatever your heart desires. Recent improvements provide peace of mind, including: Roof replaced in 2019, newer HVAC system and water heater (4 years old) and a newer well pump (9 months old). Living in the Town of Windermere is more than owning a home, it’s embracing a lifestyle. Enjoy the beloved weekly farmers market, monthly food truck nights, festive holiday celebrations, and a charming downtown just a short walk away featuring a new Italian restaurant, breakfast café, coffee shop, wine bar, tennis courts, and more. Residents also enjoy exclusive access to community boat ramps on both Lake Butler and Lake Bessie, making it easy to experience the renowned Butler Chain of Lakes. If you have been searching for a home that offers character, generous space, exceptional flexibility, and one of Central Florida’s most treasured small town lifestyles, this is an opportunity you won’t want to miss. Be sure to click on the virtual tour links.

725 Oakdale Street, Windermere
$1,114,900
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. This is your opportunity to own a home in Keene's Pointe, a 24-hour guard-gated golf community on the Butler Chain of Lakes and home to the Golden Bear Club. Built by David Weekley and proudly offered by its original owner, this 4-bedroom, 4-bathroom home offers 3,646 square feet of flexible living space, including a dedicated home office, a flex room, and a spacious upstairs bonus room that could serve as a potential fifth bedroom, media room, or game room. Upstairs is also equipped with a full bathroom. A tandem three-car garage provides room for multiple vehicles, a golf cart, additional storage, or a workshop area. A brand-new roof is scheduled to be installed in early August. Inside, the thoughtfully designed floor plan begins with a formal dining room and dedicated home office just off the foyer. A secondary bedroom and full bathroom are conveniently located near the front of the home, while the open-concept family room and kitchen create the heart of the home. The kitchen features a center island, cabinetry, and countertop space. There is an existing electric range, but the community is connected to natural gas, offering the option to convert the existing electric range. Sliding glass doors open to the covered lanai and private backyard, extending the living space outdoors. The spacious first-floor primary suite offers plenty of room for a sitting area or reading nook. The primary bathroom features dual vanities, a walk-in shower, garden tub, and a spacious closet. Two additional bedrooms are privately situated on the opposite side of the home and are separated by a flex room, making it ideal as a study area, hobby space, or additional sitting room. A full bathroom with direct access to the covered lanai completes this wing of the home. Residents of Keene's Pointe enjoy private boardwalks to Lake Tibet of the Butler Chain of Lakes, community boat ramp to Lake Burden, four playgrounds, scenic green spaces, and neighborhood events. Optional membership to the Golden Bear Club offers championship golf course, tennis, a swimming pool, fitness center, dining, and an active social calendar. In order to utilize these amenities, a Golden Bear Club membership is needed. Conveniently located near Walt Disney World, shopping, dining, everyday conveniences and services, this home offers an opportunity to enjoy the lifestyle and amenities of Keene's Pointe. Disclosure: Artificial Intelligence has been utilized in public remarks and removal of some personal property.

8344 Bowden Way, Windermere
$395,000
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
$899,999
3 Beds ⋅ 2 Baths ⋅ Manors At Butler Bay Ph 01 SubDv. ⋅ 34786 Zip Code
Incredible Opportunity to own a pool home with a huge lot in a fantastic neighborhood * The 1st picture is the proposed new elevation * Call for details about the proposed changes and package price * Good Floorplan * Close to Everything * Home has 3 Bedrooms * Separate Office * Formal Living Room * Breakfast Nook with Open Kitchen * Formal Dining Room * Pool Bath * Vaulted Ceilings * Inside Laundry * Screened & Covered Pool with Large Deck * Formal Dining Room * Large Family Room with Fireplace * Must see to fully appreciate the home & get more details for the remodel options

2630 Stanton Hall Court, Windermere
$1,250,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Nestled on a quiet cul-de-sac in the desirable Hamilton Village section of Keene's Pointe, this beautifully maintained one-story Golf Villa offers the perfect blend of comfort, elegance, and low-maintenance living. Featuring 4 bedrooms, 3 bathrooms, and nearly 2,900 square feet of thoughtfully designed living space, this residence showcases extensive hardwood flooring, upgraded cabinetry, granite countertops, and an inviting open layout ideal for both everyday living and entertaining. Recent improvements provide peace of mind and exceptional value, including a brand-new metal roof, new a/c unit and fresh interior and exterior paint, enhancing both the home's appearance and long-term durability. The spacious floor plan offers generous gathering areas filled with natural light, while the well-appointed kitchen opens seamlessly to the main living spaces. The private primary suite provides a relaxing retreat, and the guest accommodations are thoughtfully positioned to offer comfort and privacy for family and visitors alike. Step outside to the screened lanai and enjoy Florida living year-round. Complete with a summer kitchen and fenced backyard, the outdoor space is perfect for dining, entertaining, or simply unwinding in a peaceful setting. Additional highlights include a two-car garage plus a dedicated golf cart garage, custom closet storage, and mature landscaping. Located within the 24-hour guard-gated community of Keene's Pointe, residents enjoy access to one of Central Florida's premier golf and lifestyle communities, with optional membership opportunities at The Golden Bear Club. Conveniently located near top-rated schools, dining, shopping, and major roadways, this exceptional Windermere home offers an outstanding opportunity to enjoy the Keene's Pointe lifestyle. Virtual Floorplan available.

6124 Foxfield Court, 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
$1,595,000
4 Beds ⋅ 5 Baths ⋅ Waterstone SubDv. ⋅ 34786 Zip Code
Situated within the beautiful gated community of Waterstone, this impeccably designed custom residence blends timeless architecture, refined finishes, and resort-inspired outdoor living into one extraordinary offering. Encompassing 3,396 square feet, the thoughtfully crafted floor plan features 4 bedrooms, 4 full bathrooms, and 1 half bath, all centered around a stunning private courtyard that creates a seamless connection between indoor and outdoor spaces. Walls of glass flood the home with natural light while framing picturesque views of the pool and outdoor living areas from nearly every room. At the heart of the home, the gourmet kitchen was designed for both everyday living and effortless entertaining. Rich custom cabinetry, exotic stone countertops, premium Bosch stainless steel appliances, a natural gas cooktop, oversized center island, and designer finishes combine to create a space as functional as it is beautiful. The adjacent great room offers a warm yet elegant gathering space, highlighted by exposed wood beam ceilings, a striking gas fireplace, integrated surround sound, and elegant architectural details throughout. The luxurious primary suite serves as a private retreat, featuring direct access to the courtyard and a spa-inspired bath complete with dual vanities, a soaking tub, walk-in shower, and thoughtfully curated finishes. A separate guest suite with its own private exterior entrance offers exceptional flexibility for multigenerational living, extended-stay guests, a home office, or a private retreat. Additional bedrooms are generously sized and well-appointed, providing comfort and privacy for family and visitors alike. Outside, the home's private courtyard transforms into a true resort sanctuary. A screened saltwater pool and raised spa are surrounded by expansive travertine decking and complemented by a beautifully appointed outdoor cabana featuring a masonry fireplace—creating the perfect setting for year-round entertaining or quiet relaxation. Constructed with both quality and efficiency in mind, the residence includes a tankless natural gas water heater, foam insulation, Low-E insulated windows and doors, and high-efficiency HVAC systems. Meticulously maintained and thoughtfully designed throughout, this exceptional Waterstone residence offers an ideal balance of luxury, comfort, and privacy in one of Windermere's most sought-after gated communities.

11832 Waterstone Loop Drive, Windermere
$824,900
4 Beds ⋅ 5 Baths ⋅ N/A SubDv. ⋅ 34786 Zip Code
Welcome home, to a bright and spacious 4 bedroom, 3 full and 2 half baths home in a highly desirable Windermere area. With no HOA where you can bring your boat or RV and your vision for the property you've looking for. Open living space with soaring ceilings, offers a flexible layout full of potential. The master suite includes private bath with hot tub and separate shower, kitchen features ample storage and eat in bar, the upstairs has three bedrooms with two full baths given family and guest room to spread out. Out back, a pool and patio are ready for quiet mornings and weekends BBQs-with plenty of space to make it your own. All this minutes from downtown Windermere, top-rated schools, Orlando's best attractions and major highways. Opportunities like this - space, location no HOA - rarely come available. Come and make it your own.

11994 Mckinnon Road, Windermere
$2,999,000
4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set on an elevated corner homesite within Isleworth, this four-bedroom residence presents a unique opportunity to secure a coveted address in one of Central Florida's most distinguished private golf communities. Encompassing more than 4,700 square feet, the property offers exceptional potential for renovation, customization, or the creation of a new vision tailored to today's luxury lifestyle.Positioned overlooking the 6th tee of Isleworth's renowned championship golf course and across from a scenic pond with water features, the homesite enjoys a picturesque setting with golf and water views and mature landscaping. Existing amenities include a pool, summer kitchen, circular driveway, and a three-car garage.For buyers seeking an opportunity to personalize a home within Isleworth or establish a long-term presence in this exceptional community, few properties offer such a compelling combination of location, scale, and potential. Surrounded by the Butler Chain of Lakes and secured by four staffed guard gates, Isleworth is renowned for its championship golf, exceptional amenities, and unparalleled lifestyle, with club membership available separately.

5073 Latrobe Dr, Windermere
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