Homes In Orlando For Sale Search
$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
$1,895,000
4 Beds ⋅ 5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside, wide-plank white oak hardwood floors, soaring ceilings and expansive black-framed glass doors create a bright, modern aesthetic while drawing the lake into the main living areas. The European-inspired kitchen anchors the home with an oversized island, quartz countertops, sleek cabinetry and smart appliances, flowing seamlessly into the dining and living spaces for easy everyday living and entertaining. The primary suite continues the home's refined design with a spa-like bath featuring a freestanding soaking tub, floating wood vanity, dual sinks and an oversized walk-in shower. Contemporary finishes and a light, neutral palette carry throughout the residence. Outdoors, a private heated pool and spa create a resort-like retreat, while the lakefront setting offers approximately 100 feet of frontage on Lake Bessie with the option to add a private dock. There is also a two car covered parking area. From morning sunrises and lake breezes to afternoons spent boating or fishing, the setting captures the relaxed lifestyle that makes Windermere so desirable. Just a short walk or golf cart ride from Downtown Windermere, the home places the weekly farmers market, parks, tennis courts, boat ramp to Lake Butler and Bessie, dining, local shops and a brewery within easy reach. Modern architecture, direct lake frontage and an exceptional in-town location come together for a rare opportunity to experience contemporary waterfront living in Windermere

930 East Boulevard, Windermere
$1,600,000
4 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Virtually Staged. 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. This option would be $3.9MM

212 W 1st Avenue, Windermere
$1,099,000
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
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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 mostly in the 1970s. Homes are block and stucco. Most homes fall between about 1,700 and 4,600 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, Fernwood Park, Palmer Park, Horizon Foods and New Academy Inc sit inside the subdivision.

What the homes are

  • Built Mostly built in the 1970s, with homes from 1910 to 2026.
  • Construction Block and stucco. Shingle roofs are near universal.
  • Style Traditional, Contemporary, Ranch. Predominantly two story.
  • Size Most homes fall between about 1,700 and 4,600 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 toTimeMiles
Downtown Orlando26 min12.2
Walt Disney World23 min12.0
Orlando International Airport31 min20.5
Universal Orlando15 min5.9

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

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 19 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 September 2026.

What homes sold for in Windermere Town

$900,000Median sale price
$384Median per square foot
35 daysMedian days to contract
19Homes sold in 12 months

Sale prices ran from $752,500 to $2,350,000, which is a wide spread and the reason a single neighborhood median is a starting point rather than an answer.

By size

Home sizeSalesMedian priceMedian $/sq ftMedian days
2,000 to 3,000 sq ft10$856,000$36320 days
3,000 sq ft and up7$2,171,470$480107 days

Larger homes usually show a lower price per square foot. That is normal and it is why a price per foot taken from the whole neighborhood should never be applied straight to one house.

Homes priced right sold far faster

Median days to go under contract. Shorter is better.

Never reduced 12 sales, closed at 95.4% of asking18 days
Reduced at least once 7 sales, closed at 94.7% of the reduced price113 days

Sellers who priced correctly and held their number went under contract in a median 18 days. Sellers who had to reduce took 113 days and still closed at 94.7% of their already reduced price, after a typical cut of $45,000. Opening high costs time and money, in that order.

Seller concessions

16%Of sales included a seller credit
$7,500Typical credit when there was one
3 of 19Sales 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 sales58%
Cash 7 sales37%
VA 1 sales5%

Cash was 37% 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 25 September 2025 through 20 September 2026, refreshed monthly and current as of September 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.