Windermere, FL Homes

/4
$395,000
- 3 Beds
- 2.5 Baths
- 1,520 Sq Ft
8638 Brookvale Dr, Windermere, FL 34786

Great opportunity to own this wonderful townhouse in the beautiful Lake Reams community near Disney World! This townhouse features 3bedrooms, 2.5 bathrooms, a 2-car garage, and a spacious courtyard for outdoor gatherings, a fully equipped kitchen that opens up into a living room. All bedrooms are located upstairs for privacy. The primary bedroom offers high ceilings and a spacious walk-in

Karina Aumaitre AK GLOBAL REALTY LLC

8638 Brookvale Dr, Windermere, FL 34786
/11
$4,500 per month
- 4 Beds
- 2.5 Baths
- 2,588 Sq Ft
- House for Rent
12025 Lake Butler Blvd, Windermere, FL 34786

Welcome to your 4-bedroom, 3-bathroom, three car garage sanctuary! As you open your beautiful door, expect to be wowed at your perfect masterpiece. You are greeted by your huge family room leading into the living room with a wood burning fireplace. Your living room boasts lighting through your rear doors leading to your gorgeous, screen enclosed patio. This home has a layout picture-perfect for

Camille Simon MCO REALTY

12025 Lake Butler Blvd, Windermere, FL 34786
/2
$925,000 Sold Apr 29, 2025

12614 Hawkstone Dr, Windermere, FL 34786
- 3 Beds
- 3.5 Baths
- 3,125 Sq Ft
- Built 2007
Last Sold Summary
- 3% Above List Price
- $296/SF
- 2 Days On Market
Current Estimated Value $911,066

Last Listing Agent Hojin Chang RE/MAX PRIME PROPERTIES

12614 Hawkstone Dr, Windermere, FL 34786

/35
Est $424,682 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,629 Sq Ft
11716 Water Run Aly, Windermere, FL 34786

11716 Water Run Aly, Windermere, FL 34786

/30
$560,000 Pending
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
7011 Nobleton Dr, Windermere, FL 34786

Under contract-accepting backup offers. Don't miss an Opportunity to own this Great Craftsman Home overlooking a serene Wooded View, located in the community of Lakes of Windermere. Impeccably maintained and Move-in ready, this 4-bedroom, 2.5-bath home offers numerous Upgrades and Touches throughout. Such as all new kitchen appliances, newly painted interior, new A/C, Hardwood flooring, Water

Sean Flatley KELLER WILLIAMS REALTY AT THE PARKS

7011 Nobleton Dr, Windermere, FL 34786
/50
$5,900 per month
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
- House for Rent
307 W 4th Ave, Windermere, FL 34786

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 outdoor spaces. The residence features four

Rob Gaudreau MAINFRAME REAL ESTATE

307 W 4th Ave, Windermere, FL 34786
/2
$1,400,000 Sold Jan 09, 2026

11474 Claymont Cir, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,238 Sq Ft
- Built 2001
Last Sold Summary
- 4% Above List Price
- $432/SF
- 5 Days On Market
Last Listing Agent Sue Webb WATSON REALTY CORP.

11474 Claymont Cir, Windermere, FL 34786

/2
Est $518,209 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
6352 Golden Dewdrop Trail, Windermere, FL 34786

6352 Golden Dewdrop Trail, Windermere, FL 34786

/35
$5,860,000
- 4 Beds
- 7 Baths
- 7,872 Sq Ft
12264 Montalcino Cir, Windermere, FL 34786

Lakefront, Luxurious, Fully Furnished Home with Private Pool in Windermere.A True Paradise!Discover this rare gem in the heart of Windermere, located in the gated community of Casa Del Lago — a spectacular residence that combines sophistication, comfort, and stunning lake views. Fully furnished, with over eight expertly designed rooms, this home was carefully customized by the builder

Jennifer Olmeda WRA BUSINESS & REAL ESTATE

12264 Montalcino Cir, Windermere, FL 34786
/2
$7,500 per month
- 4 Beds
- 3.5 Baths
- 3,328 Sq Ft
- House for Rent
2844 Midsummer Dr, Windermere, FL 34786

Fabulous gated one acre Windermere Chain of Lakes Estate with Private tennis court is currently available for lease, This 5 bedroom 3 1/2 bath includes in-law suite with private entrance. New boat dock for the avid boater along with sandy beach for ultimate waterfront entertainment. Enjoy the beautiful west facing sunsets from your large covered patio or dine beside your double sided wood burning

Dennis Conklin WINDERMERE COCOA BEACH CENTER

2844 Midsummer Dr, Windermere, FL 34786
/2
$1,122,346 Sold Aug 28, 2025

14378 Crest Palm Ave, Windermere, FL 34786
- 6 Beds
- 4 Baths
- 4,222 Sq Ft
- Built 2025
Last Sold Summary
- $266/SF
- 0 Days On Market
Current Estimated Value $1,132,000

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14378 Crest Palm Ave, Windermere, FL 34786

/33
Est $519,786 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,841 Sq Ft
8553 Crescendo Ave, Windermere, FL 34786

8553 Crescendo Ave, Windermere, FL 34786

/47
$699,815 Pending
- 3 Beds
- 2 Baths
- 1,784 Sq Ft
415 E 6th Ave, Windermere, FL 34786

Under contract-accepting backup offers. Here is an opportunity to truly make this exceptional 3-bedroom, 2-bath pool home your own in the heart of Windermere. Offering 1,784 sq ft of fully renovated living space, this residence features a refined open-concept layout with high-end vinyl flooring throughout, a statement kitchen with an oversized waterfall-edge island, and a private attached office

Omar Sousan LPT REALTY, LLC

415 E 6th Ave, Windermere, FL 34786
/2
$1,575,000 Sold May 23, 2025

2115 Lake Crescent Ct, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 3,597 Sq Ft
- Built 1989
Last Sold Summary
- 17% Below List Price
- $438/SF
- 91 Days On Market
Current Estimated Value $1,577,188

Last Listing Agent Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

2115 Lake Crescent Ct, Windermere, FL 34786

/2
Est $518,701 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,065 Sq Ft
8308 Bryce Canyon Ave, Windermere, FL 34786

8308 Bryce Canyon Ave, Windermere, FL 34786

/75
$9,999,000
- 6 Beds
- 8 Baths
- 6,783 Sq Ft
6149 Grosvenor Shore Dr, Windermere, FL 34786

Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home

Teresa Stewart SOUTHERN REALTY GROUP LLC

6149 Grosvenor Shore Dr, Windermere, FL 34786
/2
$490,000 Sold Jun 23, 2025

7201 Halton Ct, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,852 Sq Ft
- Built 2006
Last Sold Summary
- 5% Below List Price
- $265/SF
- 17 Days On Market
Current Estimated Value $491,075

Last Listing Agent Shawn McCormick ERA GRIZZARD REAL ESTATE

7201 Halton Ct, Windermere, FL 34786

/2
Est $549,901 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,710 Sq Ft
8797 Peachtree Park Ct, Windermere, FL 34786

8797 Peachtree Park Ct, Windermere, FL 34786

/60
$3,300,000 Open Sat 12PM - 2PM
- 4 Beds
- 5 Baths
- 4,693 Sq Ft
10870 Bayshore Dr, Windermere, FL 34786

Set against the shimmering waters of Little Lake Down, this extraordinary lakefronthome offers an elevated expression of luxury living. Thoughtfully designed to maximizesweeping water views, the residence delivers a refined yet inviting atmosphere ideal forboth intimate living and grand entertaining. As you step inside you are greetedby a spacious open floor plan, highlighted by a

Julie Christensen ONE LUXURY INTERNATIONAL LLC

10870 Bayshore Dr, Windermere, FL 34786
/2
$2,500,000 Sold Jan 05, 2026

2828 Marquesas Ct, Windermere, FL 34786
- 6 Beds
- 5.5 Baths
- 6,819 Sq Ft
- Built 1989
Last Sold Summary
- 33% Below List Price
- $367/SF
- 207 Days On Market
Last Listing Agent Carolyn Cook DALTON WADE INC

2828 Marquesas Ct, Windermere, FL 34786

/2
Est $2,368,854 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 4,339 Sq Ft
3992 Isabella Cir, Windermere, FL 34786

3992 Isabella Cir, Windermere, FL 34786

/36
$849,000 Pending
- 4 Beds
- 3 Baths
- 2,773 Sq Ft
9495 Westover Club Cir, Windermere, FL 34786

Welcome home to modern luxury living in the gated community of Westover Club. This impressive residence, situated on a generous 1/3-acre parcel, has been COMPLETELY updated, top to bottom/front to back with NO expense spared to offer a fresh, neutral, contemporary, move-in ready experience. The interior has NO CARPET and features NEW/2024 European white oak engineered wood flooring that flows

Jeff Powell ALL FLORIDA PREMIER REALTY GROUP LLC

9495 Westover Club Cir, Windermere, FL 34786
/70
$1,800,000 Sold Mar 10, 2025

8130 Tibet Butler Dr, Windermere, FL 34786
- 5 Beds
- 5 Baths
- 4,475 Sq Ft
- Built 2001
Last Sold Summary
- 8% Below List Price
- $402/SF
- 168 Days On Market
Current Estimated Value $1,809,395

Last Listing Agent Ye Kang ONE STOP SERVICE REALTY INC

8130 Tibet Butler Dr, Windermere, FL 34786

/2
Est $790,527 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,409 Sq Ft
6884 Trellis Vine Loop, Windermere, FL 34786

6884 Trellis Vine Loop, Windermere, FL 34786

/29
$799,000
- 4 Beds
- 2 Baths
- 2,373 Sq Ft
17514 Black Rail St, Windermere, FL 34786

New painting interior and doors and baseboards. This elegant single-level detached home features soaring 10-foot ceilings throughout, creating a bright and spacious atmosphere rarely found in one-story living. The home is thoughtfully positioned with a tranquil pond at the rear, offering both beautiful water views and exceptional privacy. A classic tiled roof adds timeless character and

He Gao U S GLORY REALTY

17514 Black Rail St, Windermere, FL 34786
/2
$1,468,000 Sold Jul 31, 2025

9032 Tavolini Terrace, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 5,247 Sq Ft
- Built 2007
Last Sold Summary
- 8% Below List Price
- $280/SF
- 42 Days On Market
Current Estimated Value $1,436,004

Last Listing Agent Jacky Herrera COMPASS FLORIDA LLC

9032 Tavolini Terrace, Windermere, FL 34786

/2
Est $669,135 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,432 Sq Ft
7201 Rambling Water Way, Windermere, FL 34786

7201 Rambling Water Way, Windermere, FL 34786

$580,990 New Construction
- 3 Beds
- 2.5 Baths
- 1,714 Sq Ft
Butler Plan at Lake Cawood Cove - Townhomes, Windermere, FL 34786

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932782, Windermere, FL 34786
/2
$650,000 Sold Jun 06, 2025

13272 Roxboro Rd, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,469 Sq Ft
- Built 2008
Last Sold Summary
- 13% Below List Price
- $263/SF
- 204 Days On Market
Current Estimated Value $647,028

Last Listing Agent Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

13272 Roxboro Rd, Windermere, FL 34786

/53
Est $1,115,952 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 4,502 Sq Ft
8799 Crescendo Ave, Windermere, FL 34786

8799 Crescendo Ave, Windermere, FL 34786

/29
$699,000
- 5 Beds
- 3.5 Baths
- 2,960 Sq Ft
12936 Droxford Rd, Windermere, FL 34786

Lakes of Windermere STUNNER! This Ashton Woods Kensington model comes with an amazing bonus room and much more! The well-established neighborhood is out of a Norman Rockwell painting, lined with trees, 15 minutes from Disney, and loaded with charm. All you will need are a couple of Adirondack chairs for the front patio and a glass of sweet tea to become part of this amazing neighborhood. The

Leo Rico UNITED REAL ESTATE PREFERRED

12936 Droxford Rd, Windermere, FL 34786
/2
$420,000 Sold Jul 09, 2025

5148 Sun Palm Dr, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,819 Sq Ft
- Built 1987
Last Sold Summary
- $231/SF
- 0 Days On Market
Last Listing Agent Amanda Salazar PREMIER SOTHEBYS INT'L REALTY

5148 Sun Palm Dr, Windermere, FL 34786

/42
Est $899,200 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,804 Sq Ft
11859 Gold Creek Trail, Windermere, FL 34786

11859 Gold Creek Trail, Windermere, FL 34786

/30
$1,130,735 Pending
- 4 Beds
- 3.5 Baths
- 3,199 Sq Ft
14261 Crest Palm Ave, Windermere, FL 34786

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. The Tidewater with BonusSpacious Living Refined - 3,199 Square Feet of Thoughtful DesignDiscover the perfect blend of space and sophistication in the Tidewater with a Bonus floor plan. This impressive two-story home offers 4 bedrooms and 3.5 bathrooms within its generous 3,199 square feet of living

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14261 Crest Palm Ave, Windermere, FL 34786
/2
$307,500 Sold Feb 20, 2025

8276 Maritime Flag St Unit 201, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Built 2007
Last Sold Summary
- 2% Below List Price
- $213/SF
- 7 Days On Market
Current Estimated Value $316,220

Last Listing Agent Marti Purdy MARTI PURDY PROPERTIES INC

8276 Maritime Flag St Unit 201, Windermere, FL 34786

/2
Est $467,409 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,760 Sq Ft
8673 Coventry Park Way, Windermere, FL 34786

8673 Coventry Park Way, Windermere, FL 34786

/81
$5,489,000
- 6 Beds
- 9 Baths
- 8,305 Sq Ft
9721 Carillon Park Dr, Windermere, FL 34786

Welcome to 9721 Carillon Park Dr, Windermere, FL 34786 - a stunning FULLY FURNISHED (furniture included-with exception of a few items) , professionally designed estate inside the guard-gated community of Keene’s Pointe.This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout. MAIN

Dianna Desboyaux DOUGLAS ELLIMAN

9721 Carillon Park Dr, Windermere, FL 34786
/2
$6,200,000 Sold Sep 15, 2025

11019 Bridge House Rd Unit R, Windermere, FL 34786
- 7 Beds
- 11 Baths
- 9,376 Sq Ft
- Built 2008
Last Sold Summary
- $661/SF
- 0 Days On Market
Current Estimated Value $5,694,702

Last Listing Agent Ronald Ziolkowski RE/MAX PRIME PROPERTIES

11019 Bridge House Rd Unit R, Windermere, FL 34786

/2
Est $3,268,231 Not Listed For Sale
- 4 Beds
- 7 Baths
- 5,727 Sq Ft
5006 Sawyer Cove Way, Windermere, FL 34786

5006 Sawyer Cove Way, Windermere, FL 34786

/19
$4,276,160 Pending
- 5 Beds
- 6.5 Baths
- 6,401 Sq Ft
1821 Windermere Rd, Windermere, FL 34786

Pre-Construction. To be built. Discover an unparalleled opportunity to acquire a sovereign 1.16-acre estate homesite in the heart of Windermere. This meticulously positioned property, oriented east-west for optimal light, is ensconced within a private setting and borders a permanent conservation area, ensuring absolute privacy and serene, unimpeded vistas. The absence of an HOA affords complete

Matthew Matthews ORLANDO TBI REALTY LLC

1821 Windermere Rd, Windermere, FL 34786

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