Windermere Homes with Private Mailbox Exterior Features

Windermere Homes with Private Mailbox Exterior Features

Welcome to Windermere, Florida, a picturesque town nestled in the heart of Orange County. Known for its stunning lakes, lush landscapes, and charming neighborhoods, Windermere offers a unique blend of tranquility and vibrant community life. Just a stone’s throw from the bustling attractions of Orlando, this quaint town provides residents with the perfect escape while keeping them connected to the excitement of city living.

One of the standout features of homes in Windermere is the allure of private mailbox exterior features. Imagine stepping out of your front door to a beautifully designed mailbox that complements your home’s architecture and adds a touch of personal flair. These private mailboxes not only enhance curb appeal but also provide a sense of individuality, making your home truly stand out in the neighborhood.

Windermere’s real estate market boasts a variety of properties, from elegant single-family homes to luxurious estates, many of which include these charming private mailboxes. This thoughtful detail reflects the town's commitment to aesthetics and community spirit, encouraging residents to take pride in their homes.

With a rich history, excellent schools, and an array of recreational activities, Windermere is more than just a place to live; it’s a lifestyle. Whether you’re enjoying a day on the water at one of the local lakes or exploring the quaint shops and eateries, you’ll find that Windermere is a delightful place to call home. Come discover the magic of this enchanting town, where the beauty of nature meets the warmth of community.

Newest Windermere Homes with Private Mailbox Exterior Features

2925 Butler Bay Drive N, Windermere
$2,200,000
5 Beds ⋅ 5 Baths ⋅ Butler Bay SubDv. ⋅ 34786 Zip Code
Virtually Staged. LUXURY LAKEFRONT ESTATE | 0.64-ACRE LOT | PRIVATE DOCK | PRIVATE POOL | OUTDOOR SUMMER KITCHEN | 3-CAR GARAGE Experience luxury living at its finest in this stunning contemporary lakefront estate, set on an impressive 0.64-acre lot. Featuring two levels of thoughtfully designed living space, this exceptional residence combines elegant architecture, upscale finishes, and breathtaking panoramic lake views. Upon entering through the beautiful solid wood double doors, you are welcomed by an impressive formal living room and a spacious formal dining area. Large panoramic windows frame the spectacular lake views, bringing natural light into the home and creating a seamless connection with the surrounding landscape. A beautifully appointed private office provides the perfect setting for working from home. The gourmet kitchen is truly a chef's dream, featuring high-quality custom cabinetry, quartz countertops, an oversized island, a spacious pantry, and generous workspace. Designed for both everyday living and entertaining, the kitchen flows effortlessly into the inviting family room, complete with custom built-in shelving and a gas fireplace. The luxurious primary suite is a private retreat, featuring elegant wood flooring, separate walk-in closets, and magnificent views of the pool and lake. The spa-inspired primary bathroom offers a large soaking tub and an expansive walk-in shower with dual showerheads. The lower level features three generously sized bedrooms, including one private en-suite bedroom. The remaining two bedrooms share a beautifully designed Jack-and-Jill bathroom, providing comfort and functionality for family members and guests. Additional interior highlights include a fully equipped laundry room with custom cabinetry and a convenient half bathroom with direct access to the pool area. The three-car side-entry garage features built-in storage cabinets, an electric vehicle charging station, and durable epoxy flooring. Step outside and discover your own private paradise! The covered lanai overlooks the beautiful pool and surrounding lake views, creating the perfect setting for relaxation and entertaining. The fully equipped outdoor summer kitchen features a sink, refrigerator, and built-in grill, making outdoor dining and entertaining effortless. Adding to this exceptional property is a private covered dock, offering a unique opportunity to enjoy the waterfront lifestyle. This remarkable lakefront estate brings together space, privacy, luxury, and spectacular views in one extraordinary property. A rare opportunity to own a truly exceptional home where every detail has been thoughtfully designed to elevate everyday living. SCHEDULE YOUR PRIVATE SHOWING TODAY AND EXPERIENCE THIS EXTRAORDINARY LAKEFRONT LIFESTYLE!

2925 Butler Bay Drive N, Windermere
105 Forest Street, Windermere
$2,700,000
5 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Virtually Staged. Pre-Construction. To be built. Experience bespoke living without the guesswork. Perfectly positioned on an expansive ~0.38-acre corner homesite in the heart of historic downtown Windermere, this pre-construction luxury estate offers a fully curated, turnkey vision where every architectural nuance and designer finish has already been expertly selected. Spanning 4,430 heated square feet (5,961 total under roof), this two-story transitional masterpiece balances warm natural textures with crisp, modern lines. The striking exterior pairs smooth stucco, organic stone cladding, bronze-framed windows, and a generous three-car garage. Inside, a two-story foyer and engineered hardwood floors lead to an expansive gathering room anchored by wood-wrapped ceiling beams, a paneled feature wall, and a gas fireplace set into a custom plaster surround. Culinary enthusiasts will fall in love with the chef’s kitchen, detailed with semi-custom cabinetry, light oak accents, reeded woodwork, solid stone surfaces, a substantial statement island, a custom plaster range hood, and a hidden walk-in pantry. The main level also hosts the owner’s retreat—a restful sanctuary complete with exposed ceiling beams, a morning beverage bar, an oversized custom closet, and a spa-grade bath equipped with a freestanding soaking tub, dual stone vanities, and a walk-in shower. Every square foot is thoughtfully calibrated for versatile modern living and entertaining. The main level balances productivity and wellness with a private executive study and a dedicated home fitness room, while an expansive second-story loft and media/flex theater provide effortless spaces for relaxation and hosting. Daily convenience is elevated through bespoke utility spaces, including a custom mudroom, an oversized laundry suite, and a dedicated pet spa complete with a built-in wash station. Outside, the living space expands onto an all-season covered lanai finished with rich wood ceiling details, natural stone accents, a full summer kitchen, and dedicated lounge and dining zones designed for year-round entertaining. Enjoy Windermere’s quintessential golf cart lifestyle: ride to weekly farmers' markets, stroll canopy-lined streets along the lakes, and take advantage of deeded Butler Chain of Lakes access, local tennis courts, golf clubs, top-tier schools, and world-class dining.

105 Forest Street, Windermere
8582 Powder Ridge Trail, Windermere
$630,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trls Ph 3b SubDv. ⋅ 34786 Zip Code
Virtually Staged. EXCELLENT OPPORTUNITY TO LIVE OR INVEST! This impressive Kipling model with lake views offers an exceptional combination of comfort, upgrades, and flexibility. The property features fully paid-off solar panels, a whole-house water filtration system, and electrical connections in the parking area with the option to install EV chargers. The main home has been thoughtfully updated. All bathrooms have been renovated, including 3 smart toilets with heated seats. The flooring throughout the main home has been replaced with high-quality waterproof luxury vinyl, providing a modern, seamless look that is both stylish and easy to maintain. The primary bedroom features a private balcony, offering an inviting additional space to relax and unwind. The kitchen features stainless steel KitchenAid appliances, granite countertops, backsplash, and LED-lit cabinetry. The spacious loft above the garage provides even more versatility and additional living space. The main home is currently VACANT and easy to show. Only the attached in-law suite is currently rented on a month-to-month basis, and the property can be delivered completely vacant at closing, ready for its new owners to move in. One of the property's greatest advantages is the in-law suite with a private entrance, making it ideal for extended family, guests, or as an opportunity to generate additional rental income. The parking area also offers the option to add a separate washer and dryer for the future occupant or guest of the in-law suite. This flexibility makes the property an excellent option for first-time homebuyers, families looking for additional space, or investors seeking additional income potential. Outside, the property features fencing and paver walkways, creating welcoming spaces to enjoy the outdoors. Strategically located just minutes from Disney, restaurants, shopping, and Central Florida's major attractions, this property combines location, upgrades, and multiple possibilities under one roof. Ready for its next owner!

8582 Powder Ridge Trail, Windermere
14038 Bluebird Park Road, Windermere
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Summerport Ph 02 SubDv. ⋅ 34786 Zip Code
Rare Windermere opportunity with water on TWO sides... Direct waterfront on one, and scenic water views on the other. Set on a premium 1.08-acre homesite with pond access and only one neighboring residence, this 4-bedroom, 4-bath home offers privacy, panoramic views, a private pool and spa, and nearly 3,400 square feet of living space. With more than $70,000 in recent improvements, the property combines an expansive indoor layout with exceptional outdoor living. Inside, soaring ceilings, designer finishes, and a grand staircase create a striking first impression. Designed for both everyday living and entertaining, the home features two spacious living areas, a well-appointed kitchen, formal dining room, butler’s pantry, dedicated office, and a custom home theater. Outfitted with a Sony 4K projector, Philips 110-inch film screen, Dolby Atmos surround-sound speakers, and seating for eight, the theater delivers an exceptional cinematic experience at home. Recent improvements include fresh interior paint, custom accent walls, a striking fireplace feature wall, updated designer lighting, a built-in Sub-Zero/Viking refrigerator, an undercounter ice maker, and reverse-osmosis water filtration. Additional highlights include a 2021 architectural roof and gutters, two HVAC systems replaced in 2020, and a split three-car garage with a climate-controlled third bay currently configured as a fitness space. Step outside to a private waterfront retreat with a pool and spa, stone firepit, expansive brick-paver lanai, and custom MegaView screen enclosure. The outdoor setting showcases panoramic water views with minimal visual obstructions, while the spacious driveway and welcoming front porch add to the home’s functionality. The backyard also provides views of Disney fireworks. Summerport amenities include a neighborhood park, playground, community beach, dock, walking and biking paths, clubhouse, community pool, fitness center, tennis and basketball courts, and gathering spaces. This Windermere residence offers a rare combination of acreage, privacy, direct waterfront, scenic water views, and resort-style outdoor living.

14038 Bluebird Park Road, Windermere
9621 Windy Ridge Road, Windermere
$6,750,000
9 Beds ⋅ 16 Baths ⋅ Windsor Hill SubDv. ⋅ 34786 Zip Code
Under Construction. Cant beat the location and land in this area is scarce !!!AS IS ....Great piece of land with the best location with main exterior done !!!!

9621 Windy Ridge Road, Windermere
1113 Dingens Avenue, Windermere
$4,100,000
6 Beds ⋅ 7 Baths ⋅ Gotha Town SubDv. ⋅ 34786 Zip Code
Thoughtfully designed and crafted by Brilliant Custom Homes, this new Windermere residence brings together warm architectural details, refined finishes and inviting spaces for everyday living and entertaining. Five bedrooms and five-and-a-half baths are complemented by a private in-law suite, bringing the total to six bedrooms and six-and-a-half baths, along with a four-car garage. Natural stone and warm wood tones establish the home’s understated elegance. Just inside, a private office at the front of the home welcomes natural light through a floor-to-ceiling window. Wide-plank light oak flooring continues into the main living spaces, where wood ceiling beams and a fireplace create a sense of warmth. Ten-foot sliding glass doors frame views of the pool and open the interior to the covered lanai. At the heart of the home, the kitchen pairs custom light oak cabinetry with Taj Mahal countertops and a paneled Thermador appliance package. The cohesive design carries into a separate butler’s pantry with a secondary refrigerator, freezer and ice machine. Ample counter space keeps small appliances conveniently accessible while preserving the main kitchen’s clean, uncluttered appearance. The primary suite offers a quiet retreat with wood ceiling beams, a morning bar and a custom walk-in closet. In the bath, a freestanding soaking tub and expansive porcelain slab shower bring a serene, spa-like quality to the space. Everyday comforts are thoughtfully considered, with dedicated laundry rooms on both the first and second floors. Generous storage throughout the home includes space beneath the staircase, while epoxy-finished floors give the four-car garage a polished appearance. Step outside to discover your own private resort. The pool and heated spa anchor an outdoor setting designed for gathering and unwinding, with bamboo planted along the rear of the property providing a natural privacy screen. A tongue-and-groove ceiling adds warmth to the covered lanai, where roll-down screens and two ceiling fans provide comfort throughout the year. A fully equipped summer kitchen and dedicated TV area make the transition from afternoon swimming to evening entertaining feel effortless. Overlooking the pool, the private in-law suite offers a welcoming retreat for extended family or guests. Accessible from the lanai or the side of the home, it includes its own living room, kitchenette, bedroom, bathroom and walk-in closet. Centralized lighting, whole-home audio and integrated security complete a residence where thoughtful design and modern convenience come together in the details.

1113 Dingens Avenue, Windermere
9601 Ambleside Drive, Windermere
$1,160,000
4 Beds ⋅ 3 Baths ⋅ Lake Down Shores Rep SubDv. ⋅ 34786 Zip Code
Virtually Staged. Move in. Reimagine. Or build new. Welcome to the Lake Down Shores lifestyle, where one-acre homesites and private community access to the Windermere Chain of Lakes offer a special opportunity. Set on a beautiful corner lot just a few homes from the lake, 9601 Ambleside Drive offers something increasingly difficult to find: a move-in-ready home today, an exceptional amount of land, and the flexibility to imagine something entirely different for the future. Situated on a full, flat acre, the property offers a generous front yard while still leaving an enormous backyard with incredible possibilities. Offering more than 3,000 square feet of single-story living, 4 bedrooms, 2.5 baths, and garage parking for four vehicles, the home has been refreshed with a roof replaced in 2021, one of two HVAC systems replaced in 2022, new interior and exterior paint, lighting and fixtures, updated bathrooms, new door hardware, new front door, new carpet in many rooms, plumbing updates, new water softener, and new water heater. Generously sized rooms and an interconnected floor plan make this a wonderful home for entertaining. Wood flooring complements the main gathering areas, while expansive near-floor-to-ceiling windows and Solatubes bring in abundant natural light. The family room connects to the kitchen and air-conditioned Florida room, which features casement windows and plantation shutters. Updated in 2020, the kitchen features abundant cabinetry with wood pull-out drawers, a large island, quartz countertops, stainless-steel Samsung and LG appliances, and a glass-top convection range. The spacious primary suite features an ensuite bath and walk-in closet, plus French doors leading to a flexible bonus room ideal for a home office, nursery, or sitting room. Three additional bedrooms are also generously sized, and a large laundry room provides additional storage. What truly distinguishes this property is the opportunity it presents. Enjoy the beautifully refreshed residence today, reimagine the existing home through a comprehensive transformation, or create an entirely new custom residence on this exceptional one-acre homesite. Additional features include a 2-car attached garage plus a separate 2-car detached garage, dedicated irrigation well, and septic system pumped in April 2026. Lake Down Shores residents enjoy access to the community’s private HOA boat ramp onto the Windermere Chain of Lakes. The seller, an experienced luxury home builder, has already developed concepts specifically for the property, including plans for both a complete renovation of the existing residence and new construction. These concepts offer a compelling vision of what this remarkable homesite could become while letting the next owner choose the path that best reflects their lifestyle. Conceptual plans are available for review and are presented for inspiration only; future improvements and construction are subject to applicable governmental and HOA approvals. To experience the builder’s design aesthetic, finishes, and portfolio of completed residences, please ask to view Web Link 1.

9601 Ambleside Drive, Windermere
13019 Garridan Avenue, Windermere
$620,000
4 Beds ⋅ 4 Baths ⋅ Windermere Sound Ph 2 SubDv. ⋅ 34786 Zip Code
Fully remodeled modern kitchen, Remodeled guest bath, Roof replaced in 2026, so no big-ticket surprises, TWO primary suites, each with a walk-in closet and a double-vanity bath, 3 full baths + half bath, Screened patio between the house and garage, Whole-house water filtration, impeccably maintained. ***No renovations. No repairs. No compromises. Just unpack and start living. Homes like this don't last. Call today and see it before someone else does!

13019 Garridan Avenue, Windermere
6518 Sawyer Shores Lane, Windermere
$2,190,000
5 Beds ⋅ 6 Baths ⋅ Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
Virtually Staged. Under Construction. Estimated completion: January 2027. Commanding architecture, soaring interiors and access to Lake Sawyer define this new contemporary residence in sought-after Windermere. Set on a wide 0.39-acre lot, its striking facade makes an immediate impression, while approximately 100 feet of canal frontage opens the door to a lifestyle on the water. As the first home along the canal from the lake, the property enjoys a short waterway connection to Lake Sawyer, with an existing floating platform designed for a personal watercraft. Offering 3,582 square feet of conditioned living space and 4,865 total square feet, the home features five bedrooms, each with an en-suite bathroom, plus a powder room, dedicated office and three-car garage. Twelve-foot ceilings on both floors and a dramatic double-height space create an exceptional sense of scale. The open layout connects the kitchen, dining and living areas for effortless everyday living and entertaining, while the main-floor primary suite offers a comfortable retreat with a walk-in closet and spacious bathroom. Extensive cabinetry and built-ins bring a tailored aesthetic throughout the home. Planned finishes include stone countertops, porcelain tile and warm wood-look flooring, complemented by a gas cooktop and an electric fireplace. The design balances contemporary presence with inviting spaces that feel comfortable to live in. Outside, a private heated pool and covered rear lanai with a grill and sink set the scene for relaxed afternoons and evenings with guests. Planned artificial turf around the pool, hardscape surfaces and landscaping complete an outdoor setting designed for enjoyment with easy upkeep. With no HOA, this property pairs the appeal of new construction with a waterfront setting close to the lake. Within walking distance of Windermere Preparatory School, ranked No. 1 among private high schools in Orange County by Niche for 2027, and conveniently located near Windermere High School. Public schools listed for this address are Windermere Elementary, Bridgewater Middle and Windermere High, all earning an A in Florida's 2026 school grades. Buyers should verify current school zoning. Limited personalization may be considered, subject to builder approval and construction timing. Discover a home where the arrival is memorable, the interiors feel expansive and time on Lake Sawyer can become part of everyday life. Images include architectural renderings and virtual staging; final materials and finishes may vary.

6518 Sawyer Shores Lane, Windermere
7231 Sangalla Drive, Windermere
$1,348,000
5 Beds ⋅ 5 Baths ⋅ Casa Del Lago-Replat SubDv. ⋅ 34786 Zip Code
Virtually Staged. Set behind the gates of Casa Del Lago, 7231 Sangalla Drive offers a fresh interpretation of Windermere living, pairing nearly 4,000 square feet of interior space with a private pool and a location remarkably connected to the destinations that define Southwest Orlando. Recently refreshed, the residence features newly painted interiors and new light white oak luxury vinyl flooring throughout the home, excluding the bathrooms. The result is a lighter, more contemporary palette that carries naturally from room to room and gives the home an entirely new point of view. At the center of the main level, the kitchen combines granite countertops, an oversized island, stainless steel appliances, gas cooking and generous cabinetry and pantry storage. It opens to the living and breakfast areas, creating one continuous space for daily living and entertaining. A formal dining room and dedicated office add definition to the floor plan without interrupting its openness. The first-floor primary suite offers a spacious retreat with a walk-in closet, dual vanities and oversized walk-in shower. Additional bedrooms provide flexibility for guests, work or creative space, while the approximately 448-square-foot upstairs bonus room adds another layer of versatility for a media lounge, game room, fitness space or secondary living area. Outside, the architecture gives way to a distinctly Florida setting. A screened swimming pool, covered lanai and expansive paver deck extend the living space outdoors, complemented by low-maintenance turf and additional backyard space. A three-car garage completes the residence. Casa Del Lago is positioned within Windermere’s Lake Burden area, placing the home near Lakeside Village, Hamlin, Downtown Windermere, Golden Oak, Four Seasons Resort Orlando, Walt Disney World Resort and the Sand Lake Road dining district known as Restaurant Row. The location offers convenient access to shopping, dining, entertainment and major roadways while maintaining the privacy of a gated residential setting. A refreshed interior, private outdoor living and a Windermere address positioned at the center of it all.

7231 Sangalla Drive, Windermere
8576 Powder Ridge Trail, Windermere
$597,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this exceptional, energy-efficient modern residence built in 2017, perfectly positioned with tranquil lake views in one of the area’s most desirable neighborhoods. Offering a spacious and thoughtfully designed main home alongside a full apartment—ideal as a private guest suite or a lucrative rental income opportunity—this property delivers unmatched versatility and lifestyle appeal. The main home features an expansive open-concept layout designed for daily living and sophisticated entertaining. The bright, airy living and dining area flow seamlessly into a modern kitchen, equipped with premium stainless steel appliances, abundant counter space, and extensive storage. A second family room offers additional possibilities for entertaining and comfort. Upstairs, the spacious primary suite features a dual-sink vanity and a walk-in shower. Two additional well-sized bedrooms offer exceptional flexibility for family, guests, or a home office. A large balcony spans the entire width of the home on both stories. A standout feature of this property is the fully independent detached granny flat, complete with its own kitchenette, bedroom, living room and full bathroom. Whether utilized for multi-generational living, visiting family, or leased out for steady rental income, this private space adds extraordinary value. Additional highlights include a secure two-car garage and patio. Situated in a vibrant community, residents enjoy resort-style amenities including a sparkling pool overlooking the lake, a dedicated dog park, playgrounds, scenic walking trails, and a picnic pavilion. This home boasts a few minute walk from top-rated schools, including Bay Lake Elementary, Horizon West Middle School and Windermere High School. This prime, highly sought-after location is just a few minute drive from historical downtown Windermere, equipped with charming boutiques and picturesque views, and in close proximity to top shopping and dining at Lakeside Village and Winter Garden Village, as well as world-famous Orlando attractions including Disney, Universal Studios, and SeaWorld. A rare find combining modern 2017 construction, income potential, and a premium neighborhood setting—schedule your private tour today!

8576 Powder Ridge Trail, Windermere
1815 Windermere Road, Windermere
$3,150,000
4 Beds ⋅ 5 Baths ⋅ 34786 Zip Code
ONE-STORY, NEW CONSTRUCTION, MODERN FARMHOUSE ELEGANCE ON 1.3 PRIVATE ACRES IN WINDERMERE. Experience an unparalleled synthesis of modern luxury and tranquil, natural beauty. This remarkable custom estate, expertly crafted by Hanson Custom Homes, presents a rare opportunity in a secluded Windermere setting. Flanked by three mature oaks trees at the entrance this generous 1.3-acres of land offers a picturesque retreat from the hustle and bustle of the city while remaining conveniently close to urban amenities. Upon approach, you are immediately impressed by the home's striking modern farmhouse aesthetic. The architecture seamlessly blends classic board-and-batten siding with contemporary clean lines. The expansive, single-story residence is designed to make a statement, centered around a private courtyard that features rich, natural wood-framed doors and a matching header that creates a warm and inviting entrance. The Hawksnest design is expertly focused on maximizing natural Florida views throughout the entire property. Backing up to a dedicated conservation area, the home offers the ultimate in privacy, framed by mature native trees and lush vegetation. This private courtyard not only serves as a welcoming entrance but also provides convenient, private access to the home office. The meticulously planned interior includes custom kitchen cabinetry and unique design features that are perfect for entertaining friends and family. The chef’s kitchen blends modern organic design with high-end functionality. Floor-to-ceiling custom warm wood cabinetry creates a seamless aesthetic, integrating panel-ready 30" Thermador refrigerator and freezer units alongside built-in pantry storage. A premium 48" six-burner range takes center stage beneath a custom plastered range hood, complemented by a wall-mounted brass pot filler and sleek vertical sconce lighting embedded directly in the full-height quartzite backsplash. Thick, mitered-edge Taj Mahal quartzite countertops stretch across the perimeter and onto an expansive center island, which comfortably accommodates five counter stools. Walk-in pantry offers a secondary refrigerator, tons of additional storage and hidden Thermador microwave. A sophisticated split floor plan ensures the primary suite remains private and separate from the other bedrooms. This primary bedroom boasts a very large walk-in closet with custom lighted cabinetry and a master bath filled with natural light from large windows and an overhead skylight. With 4 Bedrooms, 4 Full Baths, 1 Half bath, and additional dedicated spaces for a Exercise/Theater Room, Office, and Game Room, this home offers endless versatility. The property also features a oversized pool with spa and an oversized 3-Car Garage. Located just a five-minute drive from downtown Windermere or Winter Garden Village, you are perfectly situated to major highways, shopping, employment centers, and Orlando's major theme parks.

1815 Windermere Road, Windermere
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