Windermere, FL Homes

/29
$629,000
- 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
$340,000 Sold Feb 06, 2026

12716 Langstaff Dr, Windermere, FL 34786
- 2 Beds
- 2.5 Baths
- 1,181 Sq Ft
- Built 2003
Last Sold Summary
- 9% Below List Price
- $288/SF
- 85 Days On Market
Current Estimated Value $335,435

Last Listing Agent Ann Wargo UPSIDE REAL ESTATE INC

12716 Langstaff Dr, Windermere, FL 34786

/2
Est $790,861 Not Listed For Sale

6884 Trellis Vine Loop, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,409 Sq Ft
- Built 2019
6884 Trellis Vine Loop, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $242/SF
- 6 Days On Market
- Last Sold Price $825,000
- Nov 06, 2024
Last Listing Agent Jennifer Mitchell CLOCK TOWER REALTY

/81
$5,000,000
- 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 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 FEATURES: • Five bedrooms plus DETACHED GUEST HOUSE and OFFICE— providing exceptional space and

Dianna Desboyaux DOUGLAS ELLIMAN

9721 Carillon Park Dr, Windermere, FL 34786
/2
$498,000 Sold Aug 01, 2025

4813 River Gem Ave, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,085 Sq Ft
- Built 2006
Last Sold Summary
- 9% Below List Price
- $239/SF
- 55 Days On Market
Current Estimated Value $512,040

Last Listing Agent Suzanne Hosmer RE/MAX SELECT GROUP

4813 River Gem Ave, Windermere, FL 34786

/2
Est $666,013 Not Listed For Sale

7201 Rambling Water Way, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,432 Sq Ft
- Built 2015
7201 Rambling Water Way, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $280/SF
- 8 Days On Market
- Last Sold Price $680,000
- Dec 20, 2024
Last Listing Agent Jacquie Sosa EXP REALTY LLC

/3
$1,130,000
- 8 Beds
- 5 Baths
- 4,830 Sq Ft
6152 Golden Dewdrop Trail, Windermere, FL 34786

More pictures coming soon. Beautiful and spacious 8-bedroom, 5-bathroom corner home offering 4,830 sqft of living space. This well-designed property features a generous layout with plenty of room for comfortable living and entertaining. The fenced backyard provides a great outdoor space, perfect for relaxing or enjoying time outside. Located on a desirable corner lot, offering added space and

Vitor Silva VESTI LLC

6152 Golden Dewdrop Trail, Windermere, FL 34786
/2
$1,560,000 Sold Aug 11, 2025

8437 Lake Burden Cir, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,797 Sq Ft
- Built 2005
Last Sold Summary
- 16% Below List Price
- $411/SF
- 105 Days On Market
Current Estimated Value $1,538,529

Last Listing Agent Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENT

8437 Lake Burden Cir, Windermere, FL 34786

/53
Est $1,087,387 Not Listed For Sale

8799 Crescendo Ave, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 4,502 Sq Ft
- Built 2015
8799 Crescendo Ave, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $244/SF
- 19 Days On Market
- Last Sold Price $1,100,000
- Dec 14, 2023
Last Listing Agent Karen Costa FLORIDA CAPITAL REALTY

/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

Matt Matthews ORLANDO TBI REALTY LLC

1821 Windermere Rd, Windermere, FL 34786
/2
$3,350,000 Sold Jul 15, 2025

5801 Marleon Dr, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,968 Sq Ft
- Built 1997
Last Sold Summary
- 7% Below List Price
- $481/SF
- 5 Days On Market
Current Estimated Value $3,346,557

Last Listing Agent Michelle Brierley COLDWELL BANKER REALTY

5801 Marleon Dr, Windermere, FL 34786

/42
Est $881,401 Not Listed For Sale

11859 Gold Creek Trail, Windermere, FL 34786
- 6 Beds
- 4 Baths
- 3,804 Sq Ft
- Built 2012
11859 Gold Creek Trail, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $239/SF
- 8 Days On Market
- Last Sold Price $910,000
- May 07, 2024
Last Listing Agent Flavio Melo BB GROUP REALTY CORP

/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
$740,000 Sold Jan 08, 2026

11849 Cave Run Ave, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,414 Sq Ft
- Built 2014
Last Sold Summary
- 11% Below List Price
- $217/SF
- 86 Days On Market
Current Estimated Value $743,333

Last Listing Agent Any Alves WRA BUSINESS & REAL ESTATE

11849 Cave Run Ave, Windermere, FL 34786

/2
Est $450,136 Not Listed For Sale

8673 Coventry Park Way, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,760 Sq Ft
- Built 2016
8673 Coventry Park Way, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $267/SF
- 101 Days On Market
- Last Sold Price $470,000
- Dec 16, 2024
Last Listing Agent Yogini Bhave CHARLES RUTENBERG REALTY ORLANDO

/65
$3,200,000
- 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
$837,000 Sold Jun 05, 2025

6550 Crestmont Glen Ln Unit 1, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 3,282 Sq Ft
- Built 2002
Last Sold Summary
- 8% Below List Price
- $255/SF
- 14 Days On Market
Current Estimated Value $856,889

Last Listing Agent Cheryl Roda-Wu CENTURY 21 BE3

6550 Crestmont Glen Ln Unit 1, Windermere, FL 34786

/18
Est $1,077,743 Not Listed For Sale

14268 Crest Palm Ave, Windermere, FL 34786
- 4 Beds
- 4 Baths
- 3,100 Sq Ft
- Built 2025
14268 Crest Palm Ave, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $350/SF
- 38 Days On Market
- Last Sold Price $1,086,000
- Mar 19, 2025
Last Listing Agent Mark Raumaker SERHANT

/26
$295,000
- 2 Beds
- 2 Baths
- 1,161 Sq Ft
11564 Mizzon Dr Unit 202 (919), Windermere, FL 34786

Windermere Renovated Condo | Elevator | Resort Amenities | Near Disney & Shopping Renovated and move-in ready, this light-filled second-floor condo with elevator access is ideally located in one of Windermere’s most convenient areas—just minutes from Disney, Winter Garden Village, and directly across from Lakeside Village Center offering everyday shopping and dining. Designed for effortless

Nilufer Rohleder COLDWELL BANKER REALTY

11564 Mizzon Dr Unit 202 (919), Windermere, FL 34786
/2
$704,000 Sold Sep 18, 2025

1220 Glenheather Dr, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,695 Sq Ft
- Built 2002
Last Sold Summary
- 3% Below List Price
- $261/SF
- 22 Days On Market
Current Estimated Value $708,401

Last Listing Agent Dominick Florio RE/MAX TOWN & COUNTRY REALTY

1220 Glenheather Dr, Windermere, FL 34786

/2
Est $3,407,501 Not Listed For Sale

5006 Sawyer Cove Way, Windermere, FL 34786
- 4 Beds
- 7 Baths
- 5,727 Sq Ft
- Built 2018
5006 Sawyer Cove Way, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $611/SF
- 1 Day On Market
- Last Sold Price $3,500,000
- Aug 16, 2024
Last Listing Agent Shawna Tree MEGAN DOWDY REALTY, LLC

/91
$3,699,888
- 4 Beds
- 5.5 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
$4,475,000 Sold Mar 25, 2026

6474 Deacon Cir, Windermere, FL 34786
- 6 Beds
- 5.5 Baths
- 5,853 Sq Ft
- Built 1989
Last Sold Summary
- $765/SF
Current Estimated Value $4,357,796

Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

6474 Deacon Cir, Windermere, FL 34786

/21
Est $757,986 Not Listed For Sale

8736 Peachtree Park Ct, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,775 Sq Ft
- Built 2017
8736 Peachtree Park Ct, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $284/SF
- 172 Days On Market
- Last Sold Price $789,000
- Jun 24, 2024
Last Listing Agent Michael Velasquez THE SIMON SIMAAN GROUP

/35
$5,760,000
- 4 Beds
- 7 Baths
- 7,872 Sq Ft
12264 Montalcino Cir, Windermere, FL 34786

Lakefront, Luxurious, 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. with over eight expertly designed rooms, this home was carefully customized by the builder down to the smallest detail — from

Jennifer Olmeda WRA BUSINESS & REAL ESTATE

12264 Montalcino Cir, Windermere, FL 34786
/2
$2,460,000 Sold Dec 18, 2025

11019 Ullswater Ln, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 5,916 Sq Ft
- Built 2006
Last Sold Summary
- 2% Below List Price
- $416/SF
- 23 Days On Market
Current Estimated Value $2,455,129

Last Listing Agent Ken Pozek REAL BROKER, LLC

11019 Ullswater Ln, Windermere, FL 34786

/2
Est $528,387 Not Listed For Sale

6322 Golden Dewdrop Trail, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,136 Sq Ft
- Built 2012
6322 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- $247/SF
- 64 Days On Market
- Last Sold Price $527,500
- Oct 30, 2024
Last Listing Agent James Martinez CHARLES RUTENBERG REALTY ORLANDO

/78
$1,900,000
- 4 Beds
- 4 Baths
- 3,196 Sq Ft
6110 Keenes Pointe Dr, Windermere, FL 34786

Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades.This 4-bedroom plus office, 4-bath home features a highly

Donna Calhoun KELLER WILLIAMS CLASSIC

6110 Keenes Pointe Dr, Windermere, FL 34786
/2
$880,000 Sold Mar 16, 2026

11314 Ledgement Ln Unit 1, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,080 Sq Ft
- Built 2002
Last Sold Summary
- 7% Below List Price
- $286/SF
- 125 Days On Market
Current Estimated Value $894,065

Last Listing Agent Mark Vescio MARK SPAIN REAL ESTATE

11314 Ledgement Ln Unit 1, Windermere, FL 34786

/2
Est $1,255,383 Not Listed For Sale

6020 Golden Dewdrop Trail, Windermere, FL 34786
- 8 Beds
- 5 Baths
- 4,740 Sq Ft
- Built 2012
6020 Golden Dewdrop Trail, Windermere, FL 34786

Last Sold Summary
- 9% Above List Price
- $243/SF
- 30 Days On Market
- Last Sold Price $1,150,000
- Oct 17, 2024
Last Listing Agent Rick Brown KELLER WILLIAMS ADVANTAGE 2 REALTY

/65
$799,000 Pending
- 5 Beds
- 3.5 Baths
- 3,493 Sq Ft
5427 Nagami Dr, Windermere, FL 34786

Under contract-accepting backup offers. **HIGHEST AND BEST DUE TOMORROW APRIL 27th, 2026 (MONDAY) AT 6PM** Discover the lifestyle you've been searching for in this stunning two-story Windermere retreat on a peaceful cul-de-sac in the coveted Summerport community. Disney World & Universal are just 20 mins away, and the home is zoned for TOP-RANKED A+ SCHOOLS — Keenes Crossing Elementary,

Dominick Florio RE/MAX TOWN & COUNTRY REALTY

5427 Nagami Dr, Windermere, FL 34786
/2
$508,000 Sold Jan 30, 2026

12860 Penshurst Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
- Built 2003
Last Sold Summary
- 6% Above List Price
- $207/SF
- 3 Days On Market
Current Estimated Value $507,350

Last Listing Agent Jeffrey Funk EXP REALTY LLC

12860 Penshurst Ln, Windermere, FL 34786

/2
Est $564,430 Not Listed For Sale

8014 Jailene Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,322 Sq Ft
- Built 2012
8014 Jailene Dr, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $250/SF
- 5 Days On Market
- Last Sold Price $580,000
- Aug 30, 2024
Last Listing Agent Tina St Clair ST. CLAIR REALTY GROUP, LLC

/47
$875,000 Pending
- 3 Beds
- 2 Baths
- 2,386 Sq Ft
4 Chase Rd, Windermere, FL 34786

Under contract-accepting backup offers. FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge.Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and

Matthew Hughes REAL BROKER, LLC

4 Chase Rd, Windermere, FL 34786
/2
$650,000 Sold Jun 16, 2025

7036 Mapperton Dr, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 2,777 Sq Ft
- Built 2003
Last Sold Summary
- 14% Below List Price
- $234/SF
- 209 Days On Market
Current Estimated Value $647,195

Last Listing Agent Leila Ferrara WRA BUSINESS & REAL ESTATE

7036 Mapperton Dr, Windermere, FL 34786

/2
Not Listed For Sale

8136 Serenity Spring Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
- Built 2013
8136 Serenity Spring Dr, Windermere, FL 34786

Last Sold Summary
- $207/SF
- 63 Days On Market
- Last Sold Price $380,000
- Dec 02, 2024
Last Listing Agent Sophia Ferrara COLDWELL BANKER REALTY

/66
$1,895,000
- 5 Beds
- 6 Baths
- 3,728 Sq Ft
11051 Hawkshead Ct, Windermere, FL 34786

Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a

Ken Pozek REAL BROKER, LLC

11051 Hawkshead Ct, Windermere, FL 34786
/2
$9,000,000 Sold Oct 06, 2025

9832 Laurel Valley Dr, Windermere, FL 34786
- 6 Beds
- 10 Baths
- 11,100 Sq Ft
- Built 2004
Last Sold Summary
- 3% Below List Price
- $811/SF
- 0 Days On Market
Current Estimated Value $8,655,081

Last Listing Agent Dianna Desboyaux DOUGLAS ELLIMAN

9832 Laurel Valley Dr, Windermere, FL 34786

/2
Est $437,016 Not Listed For Sale

8972 Matriarca Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,692 Sq Ft
- Built 2020
8972 Matriarca Aly, Windermere, FL 34786

Last Sold Summary
- 6% Below List Price
- $275/SF
- 17 Days On Market
- Last Sold Price $465,000
- Sep 06, 2024
Last Listing Agent Jacob Hara RE/MAX

/91
$3,950,000
- 6 Beds
- 7 Baths
- 5,709 Sq Ft
12132 Montalcino Cir, Windermere, FL 34786

Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned on Lake Burden within the exclusive gated community of Casa Del Lago in Windermere. This elegant two-story residence combines refined design, functionality, and breathtaking panoramic lake views throughout.The gourmet kitchen features custom dark cabinetry, quartz

Caroline Perotti BELLA VIEW REALTY LLC

12132 Montalcino Cir, Windermere, FL 34786

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