Windermere, FL Homes

/20
$377,900
- 3 Beds
- 2.5 Baths
- 1,462 Sq Ft
5235 Keenes Pheasant Dr, Windermere, FL 34786

Charming 3-Bedroom Townhome in a Prime Location!Welcome home to this beautifully maintained 3-bedroom, 2.5-bath townhome offering 1,462 sq. ft. of comfortable living space. The spacious open-concept floor plan features a roomy kitchen, cozy family room, and a flex space that could be used as a home office—all conveniently located downstairs. Upstairs, you’ll find all three bedrooms, including

Ronda Shively COMPASS FLORIDA LLC

5235 Keenes Pheasant Dr, Windermere, FL 34786
/80
$3,250 per month
- 4 Beds
- 3.5 Baths
- 2,600 Sq Ft
- House for Rent
13426 Chariho Ln, Windermere, FL 34786

Welcome to this beautifully maintained 4-bedroom, 3-bath home with a loft and office located in a highly sought-after gated community in Windermere. This spacious residence offers a fresh, move-in-ready feel with fairly new carpeting throughout the stairs and second floor. The thoughtfully designed floor plan features a first-floor master suite, providing privacy and convenience, along with a

Courtney James LA ROSA REALTY ORLANDO LLC

13426 Chariho Ln, Windermere, FL 34786
/2
$1,094,508 Sold Apr 22, 2025

14256 Crest Palm Ave, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,764 Sq Ft
- Built 2025
Last Sold Summary
- 2% Below List Price
- $291/SF
- 128 Days On Market
Current Estimated Value $1,103,980

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14256 Crest Palm Ave, Windermere, FL 34786

/2
Est $559,551 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

/35
$420,000 Pending
- 3 Beds
- 2.5 Baths
- 1,748 Sq Ft
12838 Strode Ln, Windermere, FL 34786

Motivated Seller offering $5,000 Flex Cash to help make this home yours! With a recently replaced roof providing added peace of mind, this beautifully maintained residence also features upgraded flooring throughout—no carpet, just a clean, modern look designed for easy living. The spacious primary suite boasts a walk-in closet and private en-suite bath, while the rear-entry 2-car garage enhances

Luis Leon Medina LA ROSA REALTY LLC

12838 Strode Ln, 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
$390,000 Sold Aug 25, 2025

12884 Calderdale Ave, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,565 Sq Ft
- Built 2010
Last Sold Summary
- 2% Below List Price
- $249/SF
- 26 Days On Market
Current Estimated Value $389,448

Last Listing Agent Shirley Botansky RE/MAX PRIME PROPERTIES

12884 Calderdale Ave, Windermere, FL 34786

/2
Est $2,296,966 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

$579,990 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
/49
$5,900 per month
- 4 Beds
- 3 Baths
- 3,190 Sq Ft
- House for Rent
307 W 4th Ave, Windermere, FL 34786

Executive rental pool home located in the charming town of Windermere! The location is just two block from Main st and all that downtown Windermere has to offer! This single-story, 4-bedroom (2 primary bedrooms), 3-bathroom home, sits on an oversized corner lot in the shade of majestic oak trees. Enjoy a gourmet kitchen featuring stainless steel appliances, two brand new refrigerators, a

Katie Bray MAINFRAME REAL ESTATE

307 W 4th Ave, Windermere, FL 34786
/2
$1,085,000 Sold Dec 03, 2025

14389 Crest Palm Ave, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 4,443 Sq Ft
- Built 2024
Last Sold Summary
- 10% Below List Price
- $244/SF
- 10 Days On Market
Last Listing Agent Cindy Sapp OLYMPUS EXECUTIVE REALTY INC

14389 Crest Palm Ave, Windermere, FL 34786

/2
Est $805,967 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

/80
$2,995,000 Pending
- 6 Beds
- 5.5 Baths
- 6,819 Sq Ft
2828 Marquesas Ct, Windermere, FL 34786

Under contract-accepting backup offers. Gorgeous Private Lakefront Custom Brick Estate over 10,000 sq ft under roof, just under 7,000 sq ft under HVAC. First Time Ever on Market! Step thru the Gorgeous Leaded Glass Doors into this Magnificent Estate the Entry made for Royalty Custom Magnolia Curved Staircase with custom Italian Marble Flooring installed 2024. Updated Massive Chandler with Sconces

Carolyn Cook DALTON WADE INC

2828 Marquesas Ct, Windermere, FL 34786
/2
$1,500,000 Sold Feb 01, 2025

216 Magnolia St, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,787 Sq Ft
- Built 2016
Last Sold Summary
- $396/SF
- 2 Days On Market
Current Estimated Value $1,513,723

Last Listing Agent Mark Allen REALTY INTERNATIONAL LLC

216 Magnolia St, Windermere, FL 34786

/53
Est $1,120,581 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

/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 EXP REALTY LLC

9721 Carillon Park Dr, 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 $909,466

Last Listing Agent Hojin Chang RE/MAX PRIME PROPERTIES

12614 Hawkstone Dr, Windermere, FL 34786

/42
Est $912,935 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

/4
$2,756,995 Pending
- 6 Beds
- 6.5 Baths
- 6,996 Sq Ft
1821 Windermere Rd, Windermere, FL 34786

Under contract-accepting backup offers. 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.

Matthew Matthews ORLANDO TBI REALTY LLC

1821 Windermere Rd, 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 $1,099,500

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14378 Crest Palm Ave, Windermere, FL 34786

/2
Est $470,161 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

/57
$3,400,000
- 4 Beds
- 4 Baths
- 4,877 Sq Ft
9731 Chestnut Ridge Dr, Windermere, FL 34786

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.

Monica Lochmandy ISLEWORTH REALTY LLC

9731 Chestnut Ridge Dr, 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 $1,588,438

Last Listing Agent Jacquelyn Voigt KELLER WILLIAMS REALTY AT THE LAKES

2115 Lake Crescent Ct, Windermere, FL 34786

/2
Est $3,157,814 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

/66
$3,250,000
- 6 Beds
- 6.5 Baths
- 6,308 Sq Ft
13448 Bellaria Cir, Windermere, FL 34786

Buyer walked days before closing due to personal reasons! All inspections and milestones clean/clear!! - This exceptional Florida residence is perfectly sited on an acre within the exclusive guard-gated community of Bellaria. Thoughtfully designed to balance sophistication with comfort, the home welcomes you with an abundance of natural light streaming through broad front windows, highlighting

Shawn Kennedy KENNEDY REALTY GROUP LLC

13448 Bellaria Cir, 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 $496,053

Last Listing Agent Shawn McCormick ERA GRIZZARD REAL ESTATE

7201 Halton Ct, Windermere, FL 34786

/21
Est $793,857 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,775 Sq Ft
8736 Peachtree Park Ct, Windermere, FL 34786

8736 Peachtree Park Ct, Windermere, FL 34786

/37
$345,000
- 2 Beds
- 2.5 Baths
- 1,181 Sq Ft
12716 Langstaff Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. BACK ON THE MARKET!( due to Financial issues) . Take ADVANTAGE of this OPPORTUNITY ! LUXURY TOWNHOME LIVING IN PRIME WINDERMERE LOCATION! Call today to secure this pristine 2-bedroom, 2.5-bathroom townhouse offering the ideal central Florida lifestyle! Located in a highly sought-after Windermere community, you'll be just minutes from Disney theme

Ann Wargo UPSIDE REAL ESTATE INC

12716 Langstaff Dr, 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 $1,815,698

Last Listing Agent Ye Kang ONE STOP SERVICE REALTY INC

8130 Tibet Butler Dr, Windermere, FL 34786

/2
Est $532,303 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,136 Sq Ft
6322 Golden Dewdrop Trail, Windermere, FL 34786

6322 Golden Dewdrop Trail, Windermere, FL 34786

/63
$765,000 Pending
- 4 Beds
- 3.5 Baths
- 3,414 Sq Ft
11849 Cave Run Ave, Windermere, FL 34786

Immaculate and light-filled 4-bedroom, 3.5-bath home with a huge bonus room and flex space, located in the desirable Windermere Trails community. Just one block from the elementary school and right across from a playground that feels almost private. This spacious two-story property features an open-concept kitchen with granite waterfall-edge countertops, stainless steel appliances, and views of

Any Alves WRA BUSINESS & REAL ESTATE

11849 Cave Run Ave, 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 $1,446,200

Last Listing Agent Jacky Herrera COMPASS FLORIDA LLC

9032 Tavolini Terrace, Windermere, FL 34786

/2
Est $1,234,678 Not Listed For Sale
- 8 Beds
- 5 Baths
- 4,740 Sq Ft
6020 Golden Dewdrop Trail, Windermere, FL 34786

6020 Golden Dewdrop Trail, Windermere, FL 34786

/91
$3,775,000
- 4 Beds
- 4.5 Baths
- 6,054 Sq Ft
12812 Jacob Grace Ct, Windermere, FL 34786

Experience Unmatched Lakeside Luxury in a Custom-Built MasterpieceDiscover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined

Alireza Partovi EXP REALTY LLC

12812 Jacob Grace Ct, 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 $646,447

Last Listing Agent Luciana Amorim Panajotti FLORIDA CONNEXION PROPERTIES

13272 Roxboro Rd, Windermere, FL 34786

/2
Est $590,477 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,322 Sq Ft
8014 Jailene Dr, Windermere, FL 34786

8014 Jailene Dr, Windermere, FL 34786

/31
$940,000
- 4 Beds
- 3.5 Baths
- 3,080 Sq Ft
11314 Ledgement Ln Unit 1, Windermere, FL 34786

Located in the exclusive Glenmuir community, this beautifully appointed residence delivers refined living with timeless elegance. A grand entrance through glass French doors welcomes you into an OPEN FLOOR PLAN enhanced by elegant ceramic tile throughout. The GOURMET KITCHEN is a chef’s dream, featuring 42" cabinetry, stainless steel appliances, an oversized island, custom tile backsplash, and a

Mark Vescio MARK SPAIN REAL ESTATE

11314 Ledgement Ln Unit 1, 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 ACME REAL ESTATE FLORIDA LLC

5148 Sun Palm Dr, Windermere, FL 34786

/2
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
8136 Serenity Spring Dr, Windermere, FL 34786

8136 Serenity Spring Dr, Windermere, FL 34786

/29
$999,000
- 5 Beds
- 4 Baths
- 3,516 Sq Ft
2046 Westover Reserve Blvd, Windermere, FL 34786

Welcome to Westover Reserve, a gated Windermere enclave celebrated for its tree-lined streets, strong community identity, and central convenience. Inside, vaulted ceilings, expansive windows, and an open layout give this 5-bedroom, 4-bath WITH BONUS home an immediate sense of volume and light. The newly renovated kitchen anchors the main level with 42" cabinetry, quartz counters, an oversized

Hilary Hall COMPASS FLORIDA LLC

2046 Westover Reserve Blvd, Windermere, FL 34786

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