Windermere Homes with Community Mailbox Community Features

Windermere Homes with Community Mailbox Community Features

Welcome to Windermere, Florida – a picturesque gem nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and a charming small-town atmosphere, Windermere offers a unique blend of tranquility and modern living. This vibrant community is a haven for families, professionals, and retirees alike, boasting top-rated schools, diverse recreational activities, and a welcoming spirit that makes every resident feel at home.

One of the standout features of Windermere is its beautiful homes, many of which are part of communities that offer a community mailbox system. This thoughtful design fosters a sense of camaraderie among neighbors, encouraging social interaction and community bonding. Imagine stepping out of your front door, strolling to the community mailbox, and exchanging friendly greetings with fellow residents. It’s these little moments that create lasting memories and a strong sense of belonging.

Windermere is also known for its abundant outdoor activities. With numerous parks, walking trails, and access to pristine lakes for boating and fishing, there is always something to do. The nearby Butler Chain of Lakes provides a stunning backdrop for water enthusiasts and nature lovers alike.

In addition to its natural beauty, Windermere is conveniently located near major highways, making it easy to access the vibrant cultural offerings of Orlando, including world-class dining, shopping, and entertainment.

Whether you’re looking for a serene place to raise a family or a vibrant community to enjoy your retirement, Windermere’s charm and sense of community make it the perfect place to call home. Come explore the beauty and warmth of Windermere today!

Newest Windermere Homes with Community Mailbox Community Features

$7,000,000
5 Beds ⋅ 6 Baths ⋅ Isleworth West SubDv. ⋅ 34786 Zip Code
Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans nearly 7,000 square feet with 5 bedrooms- of which, four are on the ground floor – plus office, gym, library, storage room, upstairs media room and downstairs bonus room, perched along Lake Louise, the only lake on the Butler Chain surrounded by Isleworth. Expansive formal and living spaces are highlighted by picturesque lake views. The seamless flow from room to room takes full advantage of a layout built for living. The chef’s kitchen with island, gas cooktop, stainless appliances, hidden walk-in pantry, and built-in hutch offer an abundance of space for entertaining or family gatherings. The primary retreat offers an escape from the ordinary with peaceful lake views, a master bath with jetted tub, garden and water view shower, and a showstopping two-story custom closet that will be the envy of all. The executive office with wood walls and built-in shelving offers a luxurious setting for attending to business from home. Three secondary bedrooms on the main floor are all spacious and feature ensuite bathrooms. Upstairs is a fourth bedroom, gym, library, and open media room with balcony. Outdoor amenities include a screened patio with summer kitchen, oversized resort-style pool with travertine decking, large green space, and private dock with covered boat lift plus dock-mounted jet-ski lifts, and 3-car garage. Home also includes a full-house generator. This coveted location within Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional membership opportunities.

6055 Louise Cove Drive, Windermere
$6,650,000
5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Positioned along the back nine of Isleworth’s renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagined through an extensive three-year renovation. Showcasing timeless architecture with a fresh, sophisticated aesthetic, the residence blends elegant European influences with light-filled interiors, superior craftsmanship and refined contemporary finishes. Custom French doors open to a breathtaking foyer, where soaring double-height ceilings introduce beautifully redesigned living spaces. Beautiful new flooring, designer lighting and a striking stone fireplace create an elegant backdrop, while expansive windows frame views of the sparkling pool, spa and outdoor living areas. Designed for both everyday living and effortless entertaining, the home's central gathering spaces include a warm and inviting family room with a fully modernized media display featuring handmade wooden slats and a custom fireplace, seamlessly connected to the spectacular new kitchen. Anchored by an oversized island, the kitchen features custom cabinetry, premium Wolf and Sub-Zero appliances and generous seating, creating a welcoming space for family and guests alike. The primary suite serves as a tranquil retreat, offering direct access to its own lanai along with a beautifully renovated spa-inspired bath featuring a walk-in shower, soaking tub and dual vanities. Four spacious en-suite guest bedrooms provide exceptional comfort and privacy, while the home office offers an ideal work-from-home setting. Upstairs, the original 19th Hole-inspired game room showcases a custom bar and opens to a private balcony overlooking the 16th green. Outside, meticulously manicured grounds provide a private resort-style setting. Offering an impressive sense of scale, the expansive covered lanai features soaring volume ceilings and beautiful new oversized stone tile flooring that elevate the space's timeless architecture. A fully equipped summer kitchen overlooks the custom swimming pool and spa, while generous areas for lounging and dining create an inviting extension of the home's beautifully reimagined interiors. Together, they create the perfect environment for year-round outdoor entertaining and relaxation in one of Central Florida's most prestigious golf communities.

9921 Lake Louise Drive, Windermere
$579,857
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
$420,000
3 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twnh SubDv. ⋅ 34786 Zip Code
Located in one of Windermere’s most desirable communities, this beautifully updated 3-bedroom, 2.5-bath townhouse offers the perfect blend of style, comfort, and convenience. Just minutes from Disney, Horizon West, premier shopping, dining, and major highways Step inside to discover a bright, open-concept floor plan filled with natural light and designed for both everyday living and effortless entertaining. The modern kitchen features elegant quartz countertops, stainless steel appliances, ample cabinetry, and overlooks the spacious living and dining areas, creating the perfect gathering space for family and friends. One of the home’s standout features is the private fenced courtyard—an inviting outdoor retreat ideal for relaxing, grilling, entertaining, or simply enjoying Florida’s beautiful weather. The detached two-car garage provides added convenience and extra storage. Upstairs, the spacious primary suite offers a walk-in closet and private en-suite bathroom, while two additional bedrooms and a full bath provide flexibility for family, guests, or a home office. Residents enjoy a low HOA along with outstanding community amenities, including a resort-style swimming pool, playground, sidewalks, and scenic surroundings that make this neighborhood one of Windermere’s most sought-after communities. Zoned for highly desirable schools and located in the heart of the thriving Windermere/Horizon West area, this exceptional home combines modern updates, an unbeatable location, and outstanding value. Don’t miss this incredible opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations. Schedule your private showing today!

12744 Langstaff Drive, Windermere
$382,000
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
$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
$485,000
3 Beds ⋅ 3 Baths ⋅ Windermere Trls Prcl 3 SubDv. ⋅ 34786 Zip Code
Welcome to this charming two-story townhome in the highly desirable Windermere Trails community! Featuring 3 bedrooms, 2.5 bathrooms, and 1,631 sq. ft. of comfortable living space, this home offers an open-concept main floor seamless for daily living and entertaining. The kitchen is appointed with granite countertops, stainless steel appliances, a breakfast bar, and a spacious pantry. Upstairs, you will find all bedrooms, including a private owner's suite complete with an an-suite bathroom and generous closet space. Enjoy outdoor living with your private enclosed courtyard connecting the home to the detached 2-car garage. Community amenities include a resort-style pool, splash pad, dog park, playground, and scenic walking trails. Superb location with top-rated Orange County schools nearby and easy access to Disney, Horizon West dining, and major expressways. Schedule your private showing today!

8386 Iron Mountain Trail, Windermere
$1,090,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. *** BRAND NEW ROOF AUG 2026 *** 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. 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
$460,000
4 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph 2 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Seller may consider buyer concessions if made in an offer ~ Enjoy the best of Windermere living in this beautifully maintained 4-bedroom, 2.5-bath townhome with a rear facing 2-car garage in the sought-after Lake Burden South community! Offering a spacious, LOW MAINTENANCE LIFESTYLE, this home combines an ideal SPLIT BEDROOM floor plan with timeless finishes and an unbeatable location just steps from shopping, dining, and everyday conveniences. A charming covered front entry, attractive landscaping, and durable concrete TILE ROOF create welcoming CURB APPEAL. Inside, TILE & WOOD LAMINATE FLOORING flow throughout the home, while the light-filled OPEN CONCEPT design makes everyday living and entertaining effortless. FRENCH DOORS extend the living space to a private COURTYARD PAVER PATIO, creating the perfect spot to unwind, grill, or gather with friends. The kitchen is designed to be both functional and inviting, featuring rich cabinetry, granite countertops, a tiled backsplash, STAINLESS STEEL APPLIANCES, pantry storage, and a breakfast bar that overlooks the living and dining areas. The highly desirable MAIN FLOOR PRIMARY SUITE offers privacy and convenience with a generous WALK-IN CLOSET and a well-appointed en-suite bath. Upstairs, a versatile LOFT provides the perfect flex space for a home office, media room, or play area, while three additional bedrooms, a full bath, and upstairs laundry offer plenty of room for family, guests, or hobbies. Residents of Lake Burden South enjoy a COMMUNITY POOL and one of Windermere's most convenient locations, with easy access to Winter Garden Vineland Road, the area's beautiful lakes, Downtown Windermere, Disney, Winter Garden, Restaurant Row, shopping, dining, and major roadways. Whether you are looking for a full-time residence, a seasonal getaway, or a smart investment in one of Central Florida's most desirable communities, this exceptional townhome is ready to impress. Call today to schedule your tour and fall in love with Brownstone Street!

11429 Brownstone Street, Windermere
$330,000
2 Beds ⋅ 3 Baths ⋅ Oasis Cove I/Lakeside Village Ph 01 SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhome-style condominium nestled in the gated community of Oasis Cove at Lakeside Village in the heart of Windermere. Offering the perfect blend of comfort, style, and convenience, this move-in ready home features an open-concept floor plan with abundant natural light, creating an inviting space for both everyday living and entertaining. Residents of Oasis Cove enjoy resort-style amenities, including a community pool, fitness center, playground, clubhouse, and beautifully maintained grounds, all within a secure gated entrance. In addition to the resort-style amenities the association fees also include water, internet, cable, ground maintenance and exterior maintenance for all homes. Ideally located just minutes from Disney, Horizon West, Winter Garden Village, major highways, shopping, dining, and top-rated schools, this home offers easy access to everything Central Florida has to offer. Whether you're looking for your primary residence, a second home, or an investment opportunity, this exceptional property checks all the boxes. Don't miss your chance to own a beautiful home in one of Windermere's most desirable communities—schedule your private showing today! *New Roof + New HVAC!!*

14030 Sparkling Cove Lane Unit 603, Windermere
$6,700,000
8 Beds ⋅ 10 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located in the prestigious 24-hour guard gated community of Keene’s Pointe. Situated on a private cul-de-sac, this one of a kind residence rests on a spectacular 0.78 acre homesite with 518 feet of combined waterfront overlooking a serene pond and the beautiful waters of Lake Burden. Offering 8,133 square feet under air and 10,971 total square feet, this exceptional home features 8 bedrooms, 7 full bathrooms, and 3 half bathrooms with unparalleled craftsmanship and luxury finishes throughout. A grand marble foyer welcomes you with soaring ceilings, designer lighting, wood beams, and rich solid oak flooring. The stunning chef’s kitchen features custom solid wood cabinetry, stunning countertops, Thermador paneled refrigerator and freezer with white wine refrigeration, Wolf range, built-in convection oven, microwave, and a custom exhaust hood. The expansive great room showcases a natural stone fireplace and wall to wall sliders that open to breathtaking views of the infinity edge saltwater pool, spa, backyard oasis, and Lake Burden. The luxurious primary suite offers panoramic water views, custom illuminated walk-in closets, a spa inspired bathroom with a massive shower, designer fixtures, and a freestanding soaking tub. Additional highlights include a temperature controlled wine cellar, hidden elevator, executive study with custom built-ins, five spacious main level bedrooms, and a spectacular second floor featuring a private gym with reinforced insulation, custom theater, loft with kitchenette, balcony overlooking the water, and three ensuite bedrooms. Outdoor living is designed for entertaining with your summer kitchen including a heavy duty grill and hood, motorized screens for the entire lanai, multiple gathering areas, fire pit, private putting green, and a nature path leading to your covered boat dock with boat lift for endless Lake Burden adventures on a 125 acre skiable lake. A four-car garage with built in ceiling lighting tracks and electric vehicle charging completes this exceptional residence. Keene’s Pointe offers an unmatched lifestyle with the Golden Bear Club, featuring a championship golf course, clubhouse, fitness center, tennis courts, resort-style pool, and numerous parks and recreation areas. Ideally located just minutes from Walt Disney World, world class dining, shopping, and top rated schools, with close proximity to Windermere Preparatory School. This rare never been lived in lakefront estate is being offered for the first time and represents a unique opportunity to own one of Central Florida’s finest custom homes. Be sure to click on the virtual tour links.

8342 Boyla Court, Windermere
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