Windermere Town Homes for Sale

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

$3,450,000

4 Beds ⋅ 5 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

Exceptional waterfront living on the prestigious Butler Chain of Lakes. Discover an extraordinary expression of waterfront luxury in the charming Town of Windermere, where timeless Tuscan and Mediterranean architecture meets the elegance of refined Florida living. Ideally along the shores of Lake Down, part of the desired Butler Chain of Lakes, this exceptional residence offers a rare opportunity to experience breathtaking water views, sophisticated interiors and an unparalleled boating lifestyle. From moment you arrive, exquisite stone detailing and custom wrought-iron double entry doors establish a sense of architectural distinction. Beyond the grand entrance, soaring ceilings, expansive living spaces, and thoughtfully curated design elements create an atmosphere of understated elegance and effortless sophistication. Designed for grand-scale entertaining and intimate gatherings, the home's gracious formal dining room provides an elegant setting for memorable occasions. At the heart of the residence, an expansive great room seamlessly integrates a gourmet kitchen, casual dining area, custom bar and inviting natural gas fireplace. Framed by captivating waterfront views, this exceptional gathering space offers the ideal balance of luxury, comfort and functionality. The main-level primary suite serves as a private sanctuary, offering serene views of Lake Down and a beautifully appointed en-suite bath featuring dual vanities, two spacious walk-in closets, a luxurious jetted soaking tub and an oversized travertine shower. An additional main-level bedroom provides exceptional versatility, ideally suited for guest accommodations, a private executive office, fitness studio or creative retreat. Upstairs, two generously proportioned bedrooms provide additional privacy and comfort. Thoughtfully reconfigured from the home's original three-bedroom upper-level layout, one of these bedrooms has been transformed into an exceptionally spacious retreat, complete with its private balcony. Abundant storage throughout the residence, a spacious laundry room with a recently updated washer and dryer, and a three-car garage further enhance the home's everyday convenience. Beyond the interiors, an extraordinary outdoor oasis awaits. An expansive covered and screened lanai, custom swimming pool, lush, mature landscaping and picturesque waterfront surroundings create a private resort-inspired setting. Whether hosting elegant outdoor gatherings, enjoying a leisurely afternoon poolside, or simply taking in the tranquil beauty of the lake, every moment invites relaxation and enjoyment. For boating enthusiasts, the property's enclosed boathouse offers a distinctive waterfront amenity, featuring a protected boat area and an inviting screened retreat. With direct access to the 13 interconnected lakes of the Butler Chain, an exceptional lifestyle of boating, waterskiing, wakeboarding, paddleboarding and waterfront exploration awaits just beyond your doorstep. Adding to its appeal is the timeless charm of Windermere itself. Enjoy the town's celebrated weekly farmers market, boutique shops, inviting restaurants, local brewery, wine market and cherished community events. All this is complemented by convenient access to Orlando's premier shopping, acclaimed dining destinations, world-renowned attractions and Orlando International Airport.

703 E 6th Avenue, Windermere

$1,280,000

4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Experience the charm of Old Windermere at 104 E 1st Ave, ideally situated in the heart of one of Central Florida’s most sought-after communities. Set on an oversized 0.45-acre corner lot surrounded by mature landscaping, this beautifully reimagined single-story home offers 4 bedrooms, 2.5 bathrooms, 2,441 square feet of living space, and a 2-car garage. Transformed through an extensive renovation by Davila Homes, the residence was thoughtfully redesigned and expanded, creating the feel of a brand-new home while preserving the charm of its Old Windermere setting. The interiors showcase elevated finishes throughout, including a beautifully designed gourmet kitchen with top-of-the-line appliances, sophisticated living spaces, and carefully selected details throughout. Outside, the home embraces the Florida lifestyle with a private pool and outdoor kitchen, creating an ideal setting for entertaining, weekend gatherings, or simply enjoying the privacy and space of nearly half an acre. What truly sets this property apart is its Old Windermere location. Enjoy the character and lifestyle of living within the Town of Windermere, surrounded by tree-lined streets and just moments from local parks, dining, shopping, community events, and everything that makes this area so special—all with no HOA. Combining the character of Old Windermere with the quality, design, and finishes of a beautifully renovated home, 104 E 1st Ave offers a rare opportunity to enjoy nearly half an acre, exceptional indoor-outdoor living, and a truly turnkey residence in the heart of Windermere.

104 E 1st Avenue, Windermere

$3,300,000

4 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living. Original house was built in 1961 but completely expanded and remodeled in 2000 - present owner made upgrades in 2023 - call for details

515 W 2nd Avenue, Windermere

$1,300,000

5 Beds ⋅ 4 Baths ⋅ Town Of Windermere SubDv. ⋅ 34786 Zip Code

Virtually Staged. Nestled in the heart of Windermere, and featuring more than $300,000 in recent improvements including a brand new roof September 2026, this character-rich home offers nearly 4,200 square feet of versatile living space just steps from Windermere's charming downtown. Situated on nearly half an acre, this five-bedroom, four-bath residence pairs distinctive architectural character with thoughtful updates, abundant natural light and exceptional flexibility. The main living level brings together the kitchen, dining area and expansive great room, where high ceilings and a striking gas fireplace create a warm and inviting gathering space. Four sets of beautiful, new sliding glass doors open to an expansive balcony overlooking the screened pool, extending the living and entertaining space outdoors. A private-entry in-law suite adds another compelling feature to this unique home, offering exceptional possibilities for multigenerational living, extended-stay guests or a private work-from-home space. This lower level includes two bedrooms, two full baths, spacious living area, and a wet bar with mini-refrigerator. The fifth bedroom, currently enjoyed as a home gym, is also perfect for an office, playroom or hobby room. Privately positioned on its own level, the generous primary suite provides a peaceful retreat with a spacious sitting area and private balcony. Recent, significant investments throughout the property include new windows and doors, three newer HVAC units, new roof September 2026, interior and exterior paint, updated astroturf in the side yard, as well as numerous other improvements, all while preserving the character and scale of this established Windermere home. The pool and patio, featuring a screen enclosure just added in 2020, and newer cabanas, perfect for entertaining, relaxing and enjoying Florida living year-round. The location offers a lifestyle all its own, with downtown Windermere’s weekly farmers market, community events, parks and small-town charm just a short walk or golf cart ride away. Town of Windermere residents also enjoy private access to a boat ramp on the renowned Butler Chain of Lakes, as well as to the town tennis and pickleball courts! Zoned for top rated Windermere Elementary and Olympia High, and situated just minutes from the shopping and dining of The Grove at Isleworth and Restaurant Row, this distinctive home delivers a rare combination of space, flexibility, and character all in a desirable, downtown Windermere location.

101 Lee Street, Windermere

$1,845,000

6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

A rare opportunity in Windermere for the buyer who values space, privacy and flexibility. Set on approximately 1.15 acres with no HOA, 4282 McKinnon Road offers nearly 5,900 square feet, six bedrooms, six baths, a pool and three-car garage — all in a highly sought-after Windermere location. The floor plan is exceptionally well suited for modern luxury living, with the primary suite, guest suite and private office all on the first floor, plus expansive additional living space upstairs. It works beautifully for multigenerational living, extended guests, work-from-home needs or simply for buyers who want room to spread out without sacrificing function. Recent improvements include new windows, newer HVAC systems, a 2018 roof, updated flooring, fresh paint and additional upgrades throughout — allowing the next owner to enjoy the scale and flexibility of an estate property without taking on a long list of immediate projects. What truly sets this property apart is the freedom it offers: over an acre, no HOA, substantial living space, a pool and room for future possibilities such as additional garage or guest space, subject to applicable zoning and approvals. Zoned for Windermere Elementary, Bridgewater Middle and Windermere High School, and also conveniently located near Windermere Preparatory School and Foundation Academy, the home is just minutes from downtown Windermere, approximately 20 minutes to Disney and offers easy access to the 429. 4282 McKinnon is compelling not simply because of its size, but because of how difficult this combination is to duplicate in Windermere. For the buyer looking for a more private, flexible and substantial way to live, this is one worth seeing.

4282 Mckinnon Road, Windermere

$1,388,000

4 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Virtually Staged. Owner/developer is swamped with other projects currently... BOAT INCLUDED IN PURCHASE PRICE: Recent appraisal $1.6M. Although the value is heavily weighted towards the land this home is move-in-ready. A $3.5M modern home has been approved for building and permits are in place but the buyer has the flexibility to leave the house as-is, renovate it, build the already approved home, or bring their own builder to build their dream home. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity in the Town of Windermere. Boasting approximately 65 feet of private frontage and a dedicated boat dock, the property captures sweeping views across Wauseon Bay. The current home is in good condition and ready to move in. The interior showcases a refined yet comfortable cabin style with some modern flair and a open-concept layout, four bedrooms and thoughtfully updated living spaces. A beautifully appointed kitchen features custom cabinetry, quartz surfaces, and premium appliances, while restored hardwood flooring adds timeless character throughout. The primary suite opens to a private balcony overlooking the water, creating a serene retreat. Outdoors, the property offers a fenced yard and a rare combination of circular driveway and rear-access garage. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. There is an option to build a new home and boat dock, Permits have been approved to build a new modern home 3,500sf and 900sf covered boat dock with lift.

212 W 1st Avenue, Windermere

$1,089,000

4 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

A beautiful home in the heart of downtown Windermere, this property offers four bedrooms and three bathrooms with a perfect blend of comfort, style, and convenience. The main residence features hardwood floors throughout, spacious living areas, and large sliding doors that open to a serene, beautiful backyard — ideal for both entertaining and unwinding. An added highlight is the fully equipped separate dwelling on the property offering a private one-bedroom, one-bathroom space perfect for entertaining, or a home office/gym. Situated just minutes from local shops, parks, boat ramps, and the renowned Windermere Chain of Lakes, this home places the best of the area right at your doorstep.

715 Magnolia Street, Windermere

$1,999,000

6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code

SIGNIFICANT PRICE IMPROVEMENT! 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. 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....

713 Main Street, Windermere

$2,175,000

4 Beds ⋅ 5 Baths ⋅ Windermere Town Rep SubDv. ⋅ 34786 Zip Code

Seller is Motivated and open to negotiate! Luxury new construction lakefront home in Windermere, newly completed. Situated on Lake Bessie, this modern custom residence delivers architectural elegance, premium finishes, and a prime location just steps from the Town Center. The home offers 3,136 sq ft of air-conditioned space, featuring 4 en-suite bedrooms, a dedicated office at the entry, 5 full bathrooms, an outdoor shower, and an oversized 3-car garage. A dramatic two-story living area sets the tone with clean lines, expansive glass, and natural light throughout. The chef’s kitchen pairs performance and elegance, with a waterfall-edge quartz island, full-height book-matched backsplash, custom cabinetry, and high-end appliances including a Sub-Zero refrigerator, Wolf vent hood, and a full Thermador suite with double ovens and microwave drawer. A hidden walk-in pantry blends seamlessly into the design for added utility and clean aesthetics.Upstairs, the owner’s suite offers lake views, a spacious layout, and a sleek en-suite bath with a large walk-in shower and dual vanity. Secondary bedrooms include en-suite baths and reach-in closets. The home is finished with oversized rectangular porcelain tile throughout the entire main level including the expansive covered lanai and wide plank engineered wood flooring from the staircase through the second floor. Additional highlights include a glass-framed staircase and an abundance of natural light in every space. Located just blocks from Downtown Windermere, this home places you at the center of a highly coveted lakefront lifestyle. Enjoy tennis courts, playgrounds, boat ramps on both Lake Bessie and the Butler Chain, plus a vibrant local culture with weekly farmers markets, food truck nights, and seasonal events in Town Square. Cruise oak-lined sandy streets by golf cart, or explore nearby dining, shops, and fitness at The Grove and along Restaurant Row. World-class golf, theme parks, and the airport are all within easy reach and with the hard work already done, all that’s left is to move in and enjoy. Private showings by appointment only. Seller is Motivated and open to negotiate! We completed the closets upgrades in this beautiful home, thoughtfully designed for the family who will soon call this place home.

436 E 7th Avenue, Windermere

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Orange County › Windermere › Windermere Town

Windermere Town, Windermere

Windermere Town is a neighborhood in Windermere, in the 34786 zip code, built most often in the 1970s. Homes are block and stucco. Most homes fall between about 1,700 and 5,300 square feet under air, the median lot is roughly a third of an acre, and a two car garage is standard.

Most of Windermere Town carries no mandatory HOA.

Central Park, Palmer Park and Horizon Foods sit inside the subdivision.

What the homes are

Built Most often built in the 1970s (20% of homes), with homes from 1910 to 2027.
Construction Block and stucco. Shingle roofs on 73% of homes.
Style Traditional, Contemporary, Ranch
Size Most homes fall between about 1,700 and 5,300 square feet under air.
Bedrooms Four bedrooms is the most common plan, then three, then five.
Garage A two car garage is standard.
Lot The median lot is roughly a third of an acre.
HOA Most of the neighborhood carries no mandatory HOA. Confirm on a specific parcel before relying on it.

Where Windermere Town is

Windermere Town, centered at 28.493119, -81.532467. Drag to explore.

Street level, inside the neighborhood. Drag to look around.

Drive times below are measured on the road network from the center of Windermere Town, not straight-line distance, in free-flowing traffic. Treat them as the floor rather than the school-run average.

Driving to	Time	Miles
Downtown Orlando	26 min	12.2
Walt Disney World	23 min	12.0
Orlando International Airport	31 min	20.5
Universal Orlando	15 min	5.9

Public schools nearby

Windermere Elementary School 5 min, 1.6 mi
Olympia High School 6 min, 2.1 mi
Windy Ridge K-8 School 8 min, 2.9 mi
Thornebrooke Elementary School 9 min, 3.2 mi

Private schools nearby

New Academy Inc 2 min, 0.3 mi
Inspiring Minds Day School 6 min, 2.1 mi
Holy Family Catholic Church and School 7 min, 2.3 mi

Parks and recreation

Central Park 1 min, 0.3 mi
Fernwood Park 2 min, 0.3 mi
Palmer Park 4 min, 0.8 mi
R.D. Keene Park 6 min, 2.1 mi

Groceries and errands

Horizon Foods 2 min, 0.3 mi
Publix Super Market at The Grove 5 min, 1.8 mi
Walmart 5 min, 1.9 mi
Walmart Neighborhood Market 5 min, 1.9 mi

Useful local links

Nearest is not the same as zoned. The schools above are the closest ones to Windermere Town by distance. School attendance zones are set by the district, change from year to year, and can differ street to street inside one neighborhood. Confirm the assignment for a specific address with Orange County Public Schools before it matters to a decision.

Places and drive times from Google, checked 20 September 2026. Businesses open and close; if something here has changed, tell me and I will correct it.

This page tracks what homes in Windermere Town actually sold for over the last twelve months, how long they took, and what moved the price. It is built from 21 verified closed sales in the Stellar MLS feed, not from public estimates. Every figure is a net-of-concessions number, which is explained at the bottom. Updated November 2026.

What homes sold for in Windermere Town

$900,000Median sale price

$410Median per square foot

46 daysMedian days to contract

21Homes sold in 12 months

Sale prices ran from $690,000 to $2,334,700, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home size	Sales	Median price	Median $/sq ft	Median days
Under 2,000 sq ft	3	$752,500	$463	46 days
2,000 to 3,000 sq ft	11	$900,000	$377	25 days
3,000 sq ft and up	7	$2,171,470	$446	97 days

A price per foot taken from the whole neighborhood should never be applied straight to one house.

Price cuts and time to contract

Median days to go under contract. Shorter is better.

Never reduced 14 sales, closed at 96.7% of asking14 days

Reduced at least once 7 sales, closed at 94.7% of the reduced price100 days

Sellers who held their number went under contract in a median 14 days. Sellers who had to reduce took 100 days and still closed at 94.7% of their already reduced price, after a typical cut of $45,000.

Seller concessions

19%Of sales included a seller credit

$4,250Typical credit when there was one

4 of 21Sales carrying a credit

A seller credit covers part of the buyer's closing costs and comes off the seller's proceeds, so the headline sale price overstates what the seller kept. Budget for it if you are selling, and ask for it if you are buying.

How buyers paid

Conventional 11 sales52%

Cash 10 sales48%

Cash was 48% of purchases. A high cash share means a seller has buyers who do not depend on an appraisal, and a buyer using a loan is competing against offers that can close faster.

Questions about a specific home in Windermere Town, or want to know what yours would sell for?
Call or text Brenden Rendo at 407-616-9019 or send a message.

About this data. Source is the Stellar MLS feed for Windermere Town in Windermere, Orange County, covering closed sales from 8 November 2025 through 3 November 2026, refreshed monthly and current as of November 2026. Prices are net of seller concessions, so they reflect what the seller actually received rather than the headline number. One record was excluded as an off-market transfer rather than an open market sale. Data believed accurate but not guaranteed; listings and closings change daily.