Windermere, FL Homes

/100
$3,450,000
- 4 Beds
- 3.5 Baths
- 5,273 Sq Ft
10577 Down Lakeview Cir, Windermere, FL 34786

Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with

Simon Simaan THE SIMON SIMAAN GROUP

10577 Down Lakeview Cir, Windermere, FL 34786
/22
$12,000 Per Month
- 3 Beds
- 3 Baths
- 2,646 Sq Ft
- House for Rent
6131 Payne Stewart Dr, Windermere, FL 34786

Looking for Luxurious home in a prime location? Look no further! Located in the Isleworth Country Club, this stunning single-family home at 6131 Payne Stewart Drive is now available for rent. Situated in a fantastic waterfront location on Lake Chase, which is part of the Butler Chain of Lakes, this home is a short walk away from the world-renowned Isleworth Golf and Country Club. With breath

Jill Irwin IRWIN REALTY GROUP LLC

6131 Payne Stewart Dr, Windermere, FL 34786
/2
$700,000 Sold Feb 13, 2026

9792 Wild Oak Dr, Windermere, FL 34786
- 3 Beds
- 3.5 Baths
- 3,102 Sq Ft
- Built 1982
Last Sold Summary
- 26% Below List Price
- $226/SF
- 106 Days On Market
Current Estimated Value $747,901

Last Listing Agent Suzette Berkhalter KELLER WILLIAMS ADVANTAGE III

9792 Wild Oak Dr, Windermere, FL 34786

/69
Est $338,337 Not Listed For Sale

8110 Enchantment Dr Unit 1704, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,371 Sq Ft
- Built 2011
8110 Enchantment Dr Unit 1704, Windermere, FL 34786

Last Sold Summary
- 6% Below List Price
- $263/SF
- 19 Days On Market
- Last Sold Price $360,000
- Jul 30, 2023
Last Listing Agent Homes Orlando MAGIC KEY REALTY

/51
$1,575,000
- 5 Beds
- 3 Baths
- 3,300 Sq Ft
13124 Filly Ct, Windermere, FL 34786

Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As

Marcelo Brandao HOME N OFFICES INTERNATIONAL

13124 Filly Ct, Windermere, FL 34786
/100
$6,500 Per Month
- 2 Beds
- 2 Baths
- 1,680 Sq Ft
- House for Rent
812 East Blvd, Windermere, FL 34786

Ready for immediate occupancy. No HOA. Welcome to Sunrise on The Lake, an exceptional, fully remodeled one-story retreat in the heart of downtown Windermere with stunning views over Lake Bessie. Wake up to breathtaking sunrises and, on clear evenings, enjoy the rare treat of watching rocket launches from Cape Canaveral right your home. Inside, every detail feels elevated, solid wood floors, level

Simon Simaan THE SIMON SIMAAN GROUP

812 East Blvd, Windermere, FL 34786
/2
$1,050,000 Sold Oct 31, 2025

65 Oakdale St, Windermere, FL 34786
- 4 Beds
- 2 Baths
- 2,191 Sq Ft
- Built 1959
Last Sold Summary
- 12% Below List Price
- $479/SF
- 34 Days On Market
Current Estimated Value $1,089,673

Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

65 Oakdale St, Windermere, FL 34786

/31
Est $360,983 Not Listed For Sale

8167 Enchantment Dr Unit 1501, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,786 Sq Ft
- Built 2010
8167 Enchantment Dr Unit 1501, Windermere, FL 34786

Last Sold Summary
- 9% Below List Price
- $221/SF
- 1 Day On Market
- Last Sold Price $395,000
- Mar 18, 2024
Last Listing Agent Melanie Gocinski REAL BROKER, LLC

/22
$399,900 Pending
- 3 Beds
- 2.5 Baths
- 1,468 Sq Ft
7361 Brightland St, Windermere, FL 34786

Under contract-accepting backup offers. New Price! Nestled in the heart of Windermere, this two-story townhome is a perfect blend of charm, comfort, and modern living. As you approach, the cute front porch entrance welcomes you, hinting at the warmth that lies within. The exterior is adorned with stone columns and crowned with a stylish barrel-tiled roof, adding character to this inviting abode.

Peter Luu REAL BROKER, LLC

7361 Brightland St, Windermere, FL 34786
/54
$6,000 Per Month
- 5 Beds
- 4 Baths
- 3,805 Sq Ft
- House for Rent
311 E 8th Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Luxury Lakefront Executive Rental in Downtown Windermere on Lake Bessie. Now offered at a newly adjusted price, this rare 5-bedroom lakefront home presents one of the most compelling rental opportunities in Windermere.Set on Lake Bessie, this renovated residence offers panoramic water views, flexible living spaces, and true indoor-outdoor Florida

Karen O'Neil COLDWELL BANKER REALTY

311 E 8th Ave, Windermere, FL 34786
/2
$890,000 Sold Jul 31, 2025

235 Oakdale St, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,562 Sq Ft
- Built 1971
Last Sold Summary
- 11% Below List Price
- $347/SF
- 274 Days On Market
Current Estimated Value $931,627

Last Listing Agent Simon Simaan THE SIMON SIMAAN GROUP

235 Oakdale St, Windermere, FL 34786

/43
Est $2,824,836 Not Listed For Sale

5054 Sawyer Cove Way, Windermere, FL 34786
- 5 Beds
- 6.5 Baths
- 5,353 Sq Ft
- Built 2020
5054 Sawyer Cove Way, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $525/SF
- 7 Days On Market
- Last Sold Price $2,810,000
- Nov 01, 2023
Last Listing Agent Julie Davis, LLC COLDWELL BANKER REALTY

/15
$979,990 New Construction
- 3 Beds
- 2.5 Baths
- 2,226 Sq Ft
Plant at Lake Cawood Cove - Traditional, Windermere, FL 34786

The Plant is a one-story home offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The spacious kitchen features a large island and flows seamlessly into the dining and family rooms. A private primary suite includes a walk-in closet, while a generously sized den and covered lanai provide versatile living spaces for work, relaxation, and outdoor enjoyment. Modern

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932781, Windermere, FL 34786
/20
$3,100 Per Month
- 4 Beds
- 2.5 Baths
- 2,618 Sq Ft
- House for Rent
4542 Blue Major Dr, Windermere, FL 34786

VACANT! Great location! Great Home! Move into this Great home inside the lovely SUMMERPORT/WINDERMERE community. This house is full of upgrades and is an Energy Star certified home. Downstairs it has all tiled floors and new laminate. Kitchen has all full appliances and granite countertops. You can also enjoy Disney fireworks at night. Upstairs there is a large master bedroom, and three bedrooms.

Daniel Zheng CINO INTERNATIONAL INC

4542 Blue Major Dr, Windermere, FL 34786
/2
$520,000 Sold Jun 26, 2025

12880 Holdenbury Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 3,103 Sq Ft
- Built 2006
Last Sold Summary
- 13% Below List Price
- $168/SF
- 67 Days On Market
Current Estimated Value $686,491

Last Listing Agent Jacquie Sosa EXP REALTY LLC

12880 Holdenbury Ln, Windermere, FL 34786

/41
Est $1,458,228 Not Listed For Sale

1121 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 3,493 Sq Ft
- Built 2017
1121 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $409/SF
- 41 Days On Market
- Last Sold Price $1,430,000
- Jun 23, 2023
Last Listing Agent John Crescenti LOKATION

/2
$855,990 New Construction
- 4 Beds
- 2.5 Baths
- 2,712 Sq Ft
Tidewater Plan at Palms at Windermere, Windermere, FL 34786

The Tidewater floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 2.5 bathrooms. Spanning 2,712 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a generous

Dream Finders Homes Builder

14207 Crest Palm Ave Unit 36489841, Windermere, FL 34786
/75
$3,800 Per Month
- 3 Beds
- 2.5 Baths
- 1,988 Sq Ft
- House for Rent
7307 Ella Ln, Windermere, FL 34786

Welcome to your new home!! Conveniently situated within the charming Windermere area, you'll find this gem House, fully furnished, 1-Master Suite, 2-bedrooms, 2 and 1/2 bathrooms, nestled within the Windermere Sound community. Opening the entry door (with a digital code locker), you will find a beautiful spacious living room, well decorated and plenty of natural light coming trough the double

Sergio Figueiredo NOVA REAL ESTATE SERVICES INC

7307 Ella Ln, Windermere, FL 34786
/2
$8,500,000 Sold Sep 05, 2025

5271 Isleworth Country Club Dr, Windermere, FL 34786
- 7 Beds
- 13 Baths
- 11,403 Sq Ft
- Built 2013
Last Sold Summary
- 3% Below List Price
- $745/SF
- 206 Days On Market
Current Estimated Value $8,232,855

Last Listing Agent Monica Lochmandy ISLEWORTH REALTY LLC

5271 Isleworth Country Club Dr, Windermere, FL 34786

/8
Est $2,150,683 Not Listed For Sale

7085 Horizon Cir, Windermere, FL 34786
- 5 Beds
7085 Horizon Cir, Windermere, FL 34786

Last Sold Summary
- 19% Above List Price
- $319/SF
- 113 Days On Market
- Last Sold Price $1,800,000
- Jun 22, 2023
Last Listing Agent Carlos Roche, PA GLOBAL FLORIDA REALTY

/67
$1,899,000
- 6 Beds
- 5.5 Baths
- 5,430 Sq Ft
9057 Balmoral Mews Square, Windermere, FL 34786

Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath 4 car garage luxury estate sits on an expansive 3⁄4-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water

Ryan Rogers REAL BROKER, LLC

9057 Balmoral Mews Square, Windermere, FL 34786
/29
$3,700 Per Month
- 4 Beds
- 3.5 Baths
- 2,350 Sq Ft
- House for Rent
7401 Ella Ln, Windermere, FL 34786

Spectacular Windermere home offering elegance, comfort, and a highly functional layout. Freshly painted with brand-new luxury vinyl flooring throughout, this 4-bedroom, 3.5-bathroom residence is located in the desirable Windermere Sound community. The home features bright, open living spaces with a seamless flow between the kitchen, dining, and living areas, ideal for daily living and

Fernanda Berretta AUTHENTIC REAL ESTATE TEAM

7401 Ella Ln, Windermere, FL 34786
/2
$480,000 Sold Sep 26, 2025

13715 Bressler Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
- Built 2019
Last Sold Summary
- 9% Below List Price
- $224/SF
- 215 Days On Market
Current Estimated Value $480,017

Last Listing Agent Irene Calderon PREFERRED REAL ESTATE BROKERS

13715 Bressler Aly, Windermere, FL 34786

/59
Est $1,870,821 Not Listed For Sale

13407 Bellaria Cir, Windermere, FL 34786
- 4 Beds
- 6 Baths
- 3,640 Sq Ft
- Built 2014
13407 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $522/SF
- 10 Days On Market
- Last Sold Price $1,900,000
- Jun 27, 2024
Last Listing Agent Susan Wilkinson ORANGE TREE REALTY

/31
$899,990
- 4 Beds
- 3.5 Baths
- 3,133 Sq Ft
12688 Salomon Cove Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. Step into a home that truly has it all. From the moment you arrive, the curb appeal stands out with its stone-accented elevation, paver driveway, and inviting entry. Inside, you’ll find a thoughtfully designed open floor plan with wood-look tile throughout the main living areas, crown molding throughout the entire home, and a layout that balances

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

12688 Salomon Cove Dr, Windermere, FL 34786
/56
$5,475 Per Month
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
- House for Rent
307 W 4th Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Available for lease, this refined single-story pool residence is located in the Town of Windermere, just moments from Main Street and the downtown district’s dining, shopping, and community amenities. Positioned on an oversized corner lot beneath mature oak trees, the property offers a private and well-composed setting with thoughtful indoor and

Rob Gaudreau MAINFRAME REAL ESTATE

307 W 4th Ave, Windermere, FL 34786
/2
$930,000 Sold Nov 10, 2025

5141 Autumn Ridge Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,390 Sq Ft
- Built 1990
Last Sold Summary
- 2% Below List Price
- $389/SF
- 91 Days On Market
Current Estimated Value $907,353

Last Listing Agent Deb Schroeder INFINITY REALTY GROUP LLC

5141 Autumn Ridge Ln, Windermere, FL 34786

/58
Est $1,696,741 Not Listed For Sale

11603 Vinci Dr, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,672 Sq Ft
- Built 2013
11603 Vinci Dr, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $449/SF
- 60 Days On Market
- Last Sold Price $1,650,000
- Nov 17, 2023
Last Listing Agent Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

/61
$487,000
- 4 Beds
- 2.5 Baths
- 2,092 Sq Ft
10624 Reams Rd, Windermere, FL 34786

Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trails community. Just minutes from Disney World, you can enjoy nightly fireworks right from your front porch. The kitchen features 42" maple cabinets, granite countertops, and under-cabinet lighting. An open-concept design connects the spacious living and with the kitchen, perfect for entertaining. The primary

Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

10624 Reams Rd, Windermere, FL 34786
/10
$13,500 Per Month
- 5 Beds
- 5.5 Baths
- 5,498 Sq Ft
- House for Rent
11051 Coniston Way, Windermere, FL 34786

This exquisite custom residence in the Reserve at Lake Butler Sound community offers unparalleled luxury and sophistication. Striking wrought-iron arched double entry doors open to a seamless, airy floor plan featuring elegant travertine flooring and captivating views of the pool and lanai area.Elegant wrought-iron chandeliers grace the welcoming foyer and generous dining space. This home is

Juan Delgado LA ROSA REALTY LLC

11051 Coniston Way, Windermere, FL 34786
/2
$518,000 Sold May 14, 2025

5014 Wise Bird Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,342 Sq Ft
- Built 2004
Last Sold Summary
- 13% Below List Price
- $221/SF
- 102 Days On Market
Current Estimated Value $526,119

Last Listing Agent Hong Lu CHARLES RUTENBERG REALTY ORLANDO

5014 Wise Bird Dr, Windermere, FL 34786

/31
Est $764,581 Not Listed For Sale

8748 Peachtree Park Ct, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,514 Sq Ft
- Built 2017
8748 Peachtree Park Ct, Windermere, FL 34786

Last Sold Summary
- 9% Above List Price
- $278/SF
- 0 Days On Market
- Last Sold Price $700,000
- Jun 01, 2023
Last Listing Agent Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

/30
$629,900
- 3 Beds
- 2 Baths
- 2,147 Sq Ft
13622 Darchance Rd, Windermere, FL 34786

Welcome home to Berkshire Park. This 3bedroom, 2bath residence offers a balance of comfort and convenience in a quiet residential setting. Ideally located just minutes from world-class attractions including Walt Disney World, as well as shopping, dining, and major highways, this property places you at the center of Central Florida living. The community is surrounded by nearby schools, adding

Javin Lopez AVANTI WAY REALTY LLC

13622 Darchance Rd, Windermere, FL 34786
/16
$2,850 Per Month
- 3 Beds
- 2.5 Baths
- 2,306 Sq Ft
- House for Rent
13231 Overstreet Rd, Windermere, FL 34786

Vacant! Great Location! Great House!! Must See!!! Move into this home inside the lovely Berkshire Park community in the very desirable town of Windermere. This house is full of upgrades and is an Energy Star certified home. Downstairs has tiled floors, and a private study room. It oversees the front porch. Kitchen has all appliances and granite countertop. It opens to the Great Room and provides

Daniel Zheng CINO INTERNATIONAL INC

13231 Overstreet Rd, Windermere, FL 34786
/2
$390,000 Sold Apr 28, 2026

8226 Serenity Spring Dr Unit 2402, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,028 Sq Ft
- Built 2013
Last Sold Summary
- 2% Below List Price
- $192/SF
- 28 Days On Market
Current Estimated Value $395,382

Last Listing Agent Garrett Turner EXP REALTY LLC

8226 Serenity Spring Dr Unit 2402, Windermere, FL 34786

/2
Est $3,142,686 Not Listed For Sale

4261 Isabella Cir, Windermere, FL 34786
- 6 Beds
- 9 Baths
- 7,129 Sq Ft
- Built 2016
4261 Isabella Cir, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $456/SF
- 37 Days On Market
- Last Sold Price $3,250,000
- Sep 13, 2024
Last Listing Agent Chad Going SERHANT

/13
$1,135,990 New Construction
- 5 Beds
- 4.5 Baths
- 3,542 Sq Ft
Duval Plan at Lake Cawood Cove - Traditional, Windermere, FL 34786

The Duval is a two‐story home offering five bedrooms, four full bathrooms, one half bathroom, and a two‐car garage. A bright kitchen with breakfast nook anchors the open main floor, while a second‐floor loft overlooks the family room below. The private second‐floor primary suite, optional butler’s pantry, and centrally located laundry room add convenience and luxury to this spacious plan.

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932788, Windermere, FL 34786
/2
$2,650 Per Month
- 3 Beds
- 2.5 Baths
- 1,624 Sq Ft
- Property for Rent
11642 Water Run Aly, Windermere, FL 34786

3 bedroom 2 bathroom townhouse.Ashlin Park is a peaceful community located in the beautiful town of Windermere. This neighborhood offers a community pool and clubhouse for your comfort and convenience. Ashlin Park is an ideal location due to its proximity to the Lakeside Shopping Center, many highly rated K-12 schools and Walt Disney World.1 Year Lease HOA Approval might be required.

Rafael Izquierdo Lasaracina VS INTERNATIONAL PROPERTIES

11642 Water Run Aly, Windermere, FL 34786
/2
$745,000 Sold Jul 28, 2025

9676 Wild Oak Dr, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,856 Sq Ft
- Built 1977
Last Sold Summary
- 21% Below List Price
- $261/SF
- 102 Days On Market
Current Estimated Value $774,277

Last Listing Agent Hardy Edwards, III BHHS FLORIDA REALTY

9676 Wild Oak Dr, Windermere, FL 34786

/58
Est $611,744 Not Listed For Sale

7610 Brofield Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,610 Sq Ft
- Built 2010
7610 Brofield Ave, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $230/SF
- 95 Days On Market
- Last Sold Price $600,000
- Jan 26, 2024
Last Listing Agent Isabel Sirizzotti SUNNY 365 REALTY GROUP

Showing Results 161 - 200, Page 5 of 18

Florida Orange County Windermere

How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Windermere, FL Homes

Real Estate & Homes