Windermere Homes for Sale

Welcome to Windermere, Florida – a picturesque subdivision that embodies the perfect blend of luxury living and serene natural beauty. Nestled in the heart of Orange County, Windermere is renowned for its charming, tree-lined streets, stunning waterfront views, and a welcoming community atmosphere. This idyllic locale is just a stone's throw away from the vibrant attractions of Orlando, making it an ideal choice for those seeking both tranquility and convenience.

Windermere offers an impressive array of homes for sale, catering to a variety of lifestyles and preferences. From elegant single-family residences to modern townhomes, each property is designed with meticulous attention to detail. Many homes feature expansive layouts, gourmet kitchens, and private outdoor spaces perfect for entertaining or enjoying Florida's year-round sunshine. With lush landscaping and scenic views of the nearby lakes, living in Windermere feels like a daily retreat.

Residents of Windermere enjoy access to top-rated schools, upscale shopping, and a plethora of recreational activities, including golf courses and parks. The community also hosts various events throughout the year, fostering a strong sense of camaraderie among neighbors.

Whether you're a first-time homebuyer or looking to upgrade to your dream home, Windermere presents an unparalleled opportunity in the Florida real estate market. Explore the available homes for sale today and discover why so many choose to call this enchanting community their home. Embrace the Windermere lifestyle – where luxury meets comfort in a stunning natural setting!

Newest Windermere Homes for Sale

$1,995,000

6 Beds ⋅ 6 Baths ⋅ O6432910 MLS

Welcome to 4282 McKinnon Rd, a beautifully updated Windermere estate offering exceptional space, privacy, and flexibility on approximately 1.15 acres—with NO HOA. Featuring 6 bedrooms, 6 baths, nearly 5,900 square feet of living space, a private pool, and 3-car garage, this custom home combines an impressive floor plan with extensive recent improvements. Move-in ready and refreshed inside and out, the home features new windows and doors, new interior and exterior paint, new flooring, new AC systems, a new water heater, and a beautifully renovated pool. The thoughtfully designed floor plan is a standout, beginning with a spacious first-floor primary suite offering privacy and convenience. Also on the main level is a separate guest suite, ideal for visitors or multigenerational living, along with a private dedicated office for working from home. Generous living and entertaining spaces are filled with natural light, while the spacious kitchen offers abundant cabinetry, a center island, walk-in pantry, breakfast bar, and casual dining area. Upstairs, a junior primary suite with a private balcony creates another inviting retreat. Additional bedrooms provide plenty of room for family and guests, while the large bonus room over the garage offers endless possibilities as a home theater, game room, fitness studio, playroom, or additional living space. Step outside to enjoy the Florida lifestyle from the covered lanai and renovated private pool, surrounded by an expansive homesite and mature landscaping. With over an acre to enjoy and NO HOA, there is a rare sense of freedom, privacy, and breathing room. Offering extensive updates, multiple bedroom suites, a private office, oversized bonus room, pool, 3-car garage, over an acre of land, and NO HOA, 4282 McKinnon Rd delivers an exceptional combination of space and versatility in sought-after Windermere.

4282 Mckinnon Road, Windermere

Listing courtesy of COMPASS FLORIDA LLC. 407-203-9441

$348,000

3 Beds ⋅ 2 Baths ⋅ 2158722 MLS

Move-in ready and beautifully updated, this 3-bedroom, 2-bath home is tucked away on a quiet cul-de-sac in the desirable Mandarin Windermere community. Inside, you'll find luxury vinyl plank flooring throughout with no carpet, vaulted ceilings, clerestory windows that fill the home with natural light, and an open, inviting layout. The updated kitchen features granite countertops, while both bathrooms have been tastefully renovated with marble tile and modern fixtures. Fresh interior and exterior paint, newer windows, and a 2014 roof and HVAC provide added peace of mind. Enjoy the privacy of the backyard, plus a screened porch and patio perfect for relaxing or entertaining. No HOA or CDD fees. Convenient Mandarin location just minutes from I-295, I-95, shopping, dining, and parks.

4446 Tyne Court, Jacksonville

Courtesy of COLDWELL BANKER VANGUARD REALTY

Listing courtesy of COLDWELL BANKER VANGUARD REALTY.

Listing courtesy of JOHN BAYER from COLDWELL BANKER VANGUARD REALTY.

$7,500,000

6 Beds ⋅ 8 Baths ⋅ O6426995 MLS

Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links.

724 W 2nd Avenue, Windermere

Listing courtesy of THE SIMON SIMAAN GROUP. 407-558-1396

$290,000

3 Beds ⋅ 2 Baths ⋅ 2154180 MLS

**NEW APPLIANCES*LARGE LOT*17K IN CONCESSIONS FOR FLOORING*NEW ROOF** Nestled in the highly coveted area of Mandarin, this 3 bed/2 bath home sits in a great neighborhood with NO HOA OR CDD! Inside, a gorgeous living room boasts a stone FIREPLACE and a vaulted ceiling, while the kitchen features a double sink, a breakfast bar, and NEW APPLIANCES. The spacious primary suite offers a large walk-in closet. Once the builder's model home, the garage retains its previous climate-controlled setup, making it incredibly easy to ADD over 400 sqft of bonus space that can be an extra bedroom, or whatever you need. Outside, enjoy a FENCED BACKYARD, a huge side yard with fruit trees, a storage shed, and plenty of room for your RV or boat. Commuting, shopping, and dining are a breeze with easy access to I-295! Plus, the seller is offering $17,000 in concessions so buyers can select and install their dream flooring, perfectly pairing with the roof and HVAC that were both replaced within the last 5 year s. Don't miss this opportunity!

4208 Queensway Drive, Jacksonville

Courtesy of CHAD AND SANDY REAL ESTATE GROUP

Listing courtesy of CHAD AND SANDY REAL ESTATE GROUP.

Listing courtesy of CHAD NEUMANN from CHAD AND SANDY REAL ESTATE GROUP.

$375,000

4 Beds ⋅ 3 Baths ⋅ 2151223 MLS

Nestled in the heart of Mandarin, this pool home features durable tile and vinyl flooring an expansive four-bedroom, three-bathroom layout. High ceilings flood the open-concept floor plan with natural light, seamlessly connecting the dining, living, and family spaces, which center around a cozy fireplace. Private backyard oasis complete with a large swimming pool, a low-maintenance paved seating area, and a jacuzzi that was freshly resurfaced in June 2024. Converted garage now serves as a spacious fourth bedroom with its own full bathroom. No HOA, New A/C and water heater (both installed June 2024) and Roof replaced in February 2021. Tour today!

10720 Knottingby Drive, Jacksonville

Courtesy of REDFIN CORPORATION

Listing courtesy of REDFIN CORPORATION.

Listing courtesy of HEATHER KRUAYAI from REDFIN CORPORATION.

$360,000

4 Beds ⋅ 2 Baths ⋅ 2139494 MLS

Welcome to this beautifully maintained home in the highly desirable Mandarin area of Jacksonville! Featuring soaring high ceilings and an open-concept floor plan, this property offers a bright, spacious, and inviting atmosphere perfect for both everyday living and entertaining. The remodeled kitchen is a true highlight, offering modern finishes and a seamless flow into the main living areas. Recent updates provide peace of mind, including a water heater just 2 years old, HVAC replaced in 2018, floors updated 3 years ago, and a roof approximately 8 years old. Fresh interior paint gives the home a clean, move-in-ready feel. Located in one of Jacksonville's most sought-after communities, this home combines comfort, style, and convenience with close proximity to shopping, dining, parks, and top commuter routes.

4235 Queensway Drive, Jacksonville

Courtesy of EXP REALTY LLC

Listing courtesy of EXP REALTY LLC.

Listing courtesy of DANIELLA OTTONE from EXP REALTY LLC.

$2,099,000

6 Beds ⋅ 6 Baths ⋅ O6368185 MLS

Seller is offering up to $40,000 toward Buyer’s allowable closing costs, prepaids, and/or rate buy-down with acceptable offer. Pool Possibility! The accompanying video has been digitally altered to illustrate what the property could look like with a pool added. The property currently does not include a pool; however, there is potential to add one.... Come experience the character and charm of Historic Olde Windermere in a home that simply cannot be duplicated. Thoughtfully custom-built, this one-owner Transitional Craftsman residence blends timeless architecture with exceptional livability, just steps from downtown's quaint lifestyle, multiple parks, weekly farmers market, tennis courts, playgrounds, and resident-only access to the Butler Chain of Lakes. From the moment you arrive, handcrafted timber details, natural stone accents, and inviting front porch creates a sense of warmth rarely found in newer construction. Inside, soaring wood ceilings, exposed pecky cypress beams, custom built-ins, and a dramatic floor-to-ceiling stone fireplace make this house both elegant and welcoming. Designed for everyday living as much as entertaining, the chef's kitchen features premium JennAir appliances, a striking stone cooking alcove, ceiling-height cabinetry, expansive island, generous walk-in pantry, and seamless connection to the dining and family rooms. The flexible floor plan offers six bedrooms and six baths, including two private owner's suites on the main level, making the home ideal for multi-generational living, long-term guests or one of many private spaces. Upstairs, 4 spacious secondary bedrooms and a large over-garage flex room provide endless possibilities as a home fitness studio, media room, hobby space, or home office. Outdoor living is equally impressive with a large covered porch, a wood-burning fireplace, outdoor kitchen, cabana bath, Tiki hut, circular fire pit, designed for year-round enjoyment. The backyard offers ample room to design the custom pool, allowing the next owner to create a backyard tailored to their lifestyle rather than inheriting someone else's design. Additional highlights include a newer roof (2024), commercial grade fire suppression, an oversized three-car garage with exceptional storage and workspace, and the opportunity to add a front gate for enhanced privacy off Main St. Storm hardy with underground electrical utility lines and public water. This is a home has been meticulously maintained and for buyers who appreciate exceptional craftsmanship, enduring quality, and the unique lifestyle that only Historic Windermere offers. Take a short stroll to the Downtown Redevelopment Project and shop at Victoria Jewelers, Ace Hardware, Solvino Wine Bar and Fresco's, one of Dr. Phillips' favorite Italian restaurants, adding even more charm and convenience to this incredible location.

713 Main Street, Windermere

Listing courtesy of THE REAL ESTATE COLLECTION LLC. 407-656-7814

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.