Windermere, FL Homes

/36
$650,000
- 4 Beds
- 3 Baths
- 2,371 Sq Ft
6841 Helmsley Cir, Windermere, FL 34786

***NEW ROOF being installed on 2.10.26*** Step inside this home from anywhere! To experience a fully immersive walk-through of this home click on the Video or Virtual Tour button on this page. Nestled within the highly desirable Preston Square community, this elegant four-bedroom, three-bathroom pool home showcases serene pond and conservation views, offering both privacy and picturesque

Bobby Christiano COLDWELL BANKER RESIDENTIAL RE

6841 Helmsley Cir, Windermere, FL 34786
/2
$544,000 Sold Dec 01, 2025

11340 Rapallo Ln, Windermere, FL 34786
- 4 Beds
- 2 Baths
- 2,165 Sq Ft
- Built 2002
Last Sold Summary
- 3% Below List Price
- $251/SF
- 5 Days On Market
Last Listing Agent Petra Bukalo PA FLORIDA REALTY INVESTMENTS

11340 Rapallo Ln, Windermere, FL 34786

/47
Est $378,007 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,786 Sq Ft
14005 Oasis Springs Ln Unit 906, Windermere, FL 34786

14005 Oasis Springs Ln Unit 906, Windermere, FL 34786

/16
$546,300 Pending
- 5 Beds
- 2.5 Baths
- 2,521 Sq Ft
11813 Via Lucerna Cir, Windermere, FL 34786

Under contract-accepting backup offers. Auction Property. AUCTION. List price $546300 with an undisclosed reserve. Spacious 5 bed, 2.5 home offers ample space to relax and entertain with a large living area, dining area adjacent to the open kitchen, and a family room. The back porch offers views of the large lot offering the perfect space for your outdoor activities. The home has an attached 2

Andrea Butcher Thomas REALHOME SERVICE & SOLUTIONS INC

11813 Via Lucerna Cir, Windermere, FL 34786
/2
$1,280,580 Sold Mar 19, 2025

14267 Crest Palm Ave, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 4,443 Sq Ft
- Built 2025
Last Sold Summary
- $288/SF
- 0 Days On Market
Current Estimated Value $1,263,500

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14267 Crest Palm Ave, Windermere, FL 34786

/45
Est $1,652,698 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 3,585 Sq Ft
9012 Pinnacle Cir, Windermere, FL 34786

9012 Pinnacle Cir, Windermere, FL 34786

/57
$459,000 Pending
- 3 Beds
- 2.5 Baths
- 1,919 Sq Ft
12333 Via Derna Place, Windermere, FL 34786

Welcome to this beautifully updated 1,919 sq/ft townhome in the highly desirable Carrington community of Windermere. This spacious 3-bedroom, 2.5-bath residence features a freshly renovated family room, kitchen, and shared bathroom, offering a modern and inviting living experience from the moment you enter. The open-concept layout provides excellent flow for everyday living and entertaining,

Marco Romero YELLOW ROCK REALTY CORP

12333 Via Derna Place, Windermere, FL 34786
/2
$1,470,000 Sold Jun 16, 2025

5530 Oxford Moor Blvd, Windermere, FL 34786
- 5 Beds
- 5 Baths
- 5,188 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $283/SF
- 2 Days On Market
Current Estimated Value $1,489,963

Last Listing Agent Marcy Walsh REAL BROKER, LLC

5530 Oxford Moor Blvd, Windermere, FL 34786

/17
Est $688,105 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,926 Sq Ft
8712 Crescendo Ave, Windermere, FL 34786

8712 Crescendo Ave, Windermere, FL 34786

/55
$815,000 Open Sat 1PM - 3PM
- 5 Beds
- 4 Baths
- 3,294 Sq Ft
8337 Vivaro Isle Way, Windermere, FL 34786

Price adjustment! One or more photos have been virtually staged. Located minutes from the Disney attractions this property offers the unique advantage of being near one of Florida's most sought-after destinations! Welcome to a remarkable residence with a large back yard located in the highly sought community of Windermere Isle! This spacious home and location, ideal for families seeking comfort

Laurel Kellett CORCORAN PREMIER REALTY

8337 Vivaro Isle Way, Windermere, FL 34786
/2
$570,000 Sold Dec 03, 2025

11316 Rapallo Ln, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,925 Sq Ft
- Built 2002
Last Sold Summary
- 6% Below List Price
- $296/SF
- 153 Days On Market
Last Listing Agent Sherry Hutchins PREMIUM REALTY ADVISORS LLC

11316 Rapallo Ln, Windermere, FL 34786

/39
Est $766,377 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,136 Sq Ft
13207 Orange Isle Dr, Windermere, FL 34786

13207 Orange Isle Dr, Windermere, FL 34786

/36
$649,900 Pending
- 4 Beds
- 3 Baths
- 2,285 Sq Ft
6368 Sedona Leaf Ct, Windermere, FL 34786

Beautifully updated one-story home in Eden Isle, a cozy lakefront community with a private boat ramp in Windermere! This 4-bedroom, 3-bath property boasts a brand-new roof, fresh interior paint, and new carpet in all bedrooms. The open layout offers spacious living areas, while the split-bedroom design provides ample privacy for all, and a versatile layout suitable for life’s everchanging needs.

Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

6368 Sedona Leaf Ct, Windermere, FL 34786
/2
$1,325,000 Sold Jun 12, 2025

9501 Hempel Cove Blvd, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 4,789 Sq Ft
- Built 1996
Last Sold Summary
- 12% Below List Price
- $277/SF
- 100 Days On Market
Current Estimated Value $1,320,479

Last Listing Agent Rebekkah Boskovich REVEL REALTY LLC

9501 Hempel Cove Blvd, Windermere, FL 34786

/48
Est $770,336 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,834 Sq Ft
13608 Gorgona Isle Dr, Windermere, FL 34786

13608 Gorgona Isle Dr, Windermere, FL 34786

/31
$2,449,000
- 5 Beds
- 5.5 Baths
- 4,094 Sq Ft
11113 Lake Butler Blvd, Windermere, FL 34786

Welcome to this beautiful, unique and modern home. Recently built in 2023. Secluded in a great sized lot and within the sought-after and exclusive City of Windermere, known for its lush nature landscape trails, recreation parks, restaurants, cozy stores, beautiful lakes, great schools and much more!!! This luxury property also has a HOA 1/24th private deeded land with lake access, dock and ramp

Stella Freeman QUATTRO R E SOLUTIONS LLC

11113 Lake Butler Blvd, Windermere, FL 34786
/2
$302,500 Sold Dec 23, 2025

12748 Langstaff Dr, Windermere, FL 34786
- 2 Beds
- 2.5 Baths
- 1,380 Sq Ft
- Built 2004
Last Sold Summary
- 11% Below List Price
- $219/SF
- 31 Days On Market
Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

12748 Langstaff Dr, Windermere, FL 34786

/23
Est $715,049 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,985 Sq Ft
9216 Outlook Rock Trail, Windermere, FL 34786

9216 Outlook Rock Trail, Windermere, FL 34786

/47
$3,500,000
- 4 Beds
- 4.5 Baths
- 4,676 Sq Ft
6130 Grosvenor Shore Dr, Windermere, FL 34786

Remarkable Waterview Estate in Keene’s Pointe! Heated Saltwater Pool, Main-Floor Living, and Expansive Outdoor Living Space. Discover an exceptional custom Goehring & Morgan home offering the perfect blend of functionality and breathtaking outdoor living, located in a cul-de-sac of the exclusive Grosvenor Village within Keene’s Pointe, known for its privacy, guard-gated security, and Golden Bear

Dianna Desboyaux DOUGLAS ELLIMAN

6130 Grosvenor Shore Dr, Windermere, FL 34786
/2
$657,500 Sold Jun 12, 2025

11045 Belmere Isles Ct, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,606 Sq Ft
- Built 2002
Last Sold Summary
- 12% Below List Price
- $252/SF
- 215 Days On Market
Current Estimated Value $659,357

Last Listing Agent Ryan Rogers REAL BROKER, LLC

11045 Belmere Isles Ct, Windermere, FL 34786

/60
Est $676,565 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,015 Sq Ft
7949 Jailene Dr, Windermere, FL 34786

7949 Jailene Dr, Windermere, FL 34786

/11
$549,900
- 4 Beds
- 3.5 Baths
- 2,461 Sq Ft
7349 Ella Ln, Windermere, FL 34786

JUST REDUCED!!!! Live just 2 miles from Magic Kingdom and enjoy nightly views of the fireworks from your own backyard! This beautifully maintained home offers 4 bedrooms, 3.5 bathrooms, and a spacious open-concept layout perfect for both everyday living and entertaining.The kitchen shines with 42” cabinets, granite countertops, stainless steel appliances, and a large island with a breakfast

Jason Nagassar CASTLE REALTY PROFESSIONAL GROUP LLC

7349 Ella Ln, Windermere, FL 34786
/2
$1,165,000 Sold Oct 27, 2025

14404 Crest Palm Ave, Windermere, FL 34786
- 6 Beds
- 4.5 Baths
- 4,565 Sq Ft
- Built 2024
Last Sold Summary
- 3% Below List Price
- $255/SF
- 0 Days On Market
Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14404 Crest Palm Ave, Windermere, FL 34786

/28
Est $2,814,000 Not Listed For Sale
- 4 Beds
- 7 Baths
- 5,561 Sq Ft
9950 6th St, Windermere, FL 34786

9950 6th St, Windermere, FL 34786

/50
$670,000
- 4 Beds
- 3.5 Baths
- 2,297 Sq Ft
8582 Powder Ridge Trail, Windermere, FL 34786

AN IRRESISTIBLE INVESTMENT OPPORTUNITY — OR YOUR FIRST HOME!Welcome to this stunning Kipling model offering serene lake views and a host of exceptional upgrades. This home features fully paid-off solar panels, electric vehicle charging outlets, and a whole-house water filtration system for maximum efficiency and comfort. Step inside and enjoy the spacious loft above the garage, new carpeting,

Mariana Rondon LPT REALTY, LLC

8582 Powder Ridge Trail, Windermere, FL 34786
/77
$1,450,000 Sold Dec 15, 2025

8117 Whitford Ct, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 3,264 Sq Ft
- Built 2004
Last Sold Summary
- 9% Below List Price
- $444/SF
- 11 Days On Market
Last Listing Agent Mary Tisdale Keller Williams Realty Emerald

8117 Whitford Ct, Windermere, FL 34786

/41
Est $451,914 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,912 Sq Ft
13760 Calera Aly, Windermere, FL 34786

13760 Calera Aly, Windermere, FL 34786

/37
$2,249,000
- 4 Beds
- 3.5 Baths
- 4,440 Sq Ft
6134 Keenes Pointe Dr, Windermere, FL 34786

Welcome to a rare fully furnished opportunity in the heart of Keene’s Pointe, Windermere’s most acclaimed community. This renovated residence, with over 4,400 square feet of living space, has been reimagined to deliver not just a home, but an extraordinary lifestyle where every detail speaks of elegance, comfort, and sophistication. Move in ready and fully furnished!!! From the moment you step

Babi Hennemann WRA BUSINESS & REAL ESTATE

6134 Keenes Pointe Dr, Windermere, FL 34786
/2
$735,000 Sold Jul 14, 2025

12880 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 3,769 Sq Ft
- Built 2018
Last Sold Summary
- 8% Below List Price
- $195/SF
- 118 Days On Market
Current Estimated Value $752,410

Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

12880 Westside Village Loop, Windermere, FL 34786

/33
Est $1,345,028 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,493 Sq Ft
1109 Estancia Woods Loop, Windermere, FL 34786

1109 Estancia Woods Loop, Windermere, FL 34786

/24
$479,000
- 3 Beds
- 3 Baths
- 1,891 Sq Ft
12305 Via Derna Place, Windermere, FL 34786

Easy living meets a prime Windermere location in this beautifully maintained 3-bedroom, 3-full bath Carrington townhome designed for low maintenance and convenience! Major updates include a NEW ROOF (2022), adding peace of mind and long-term value. From the moment you arrive, you will appreciate the inviting CURB APPEAL, mature landscaping, and covered front entry. Inside, TILE FLOORS flow

Jennifer Wemert WEMERT GROUP REALTY LLC

12305 Via Derna Place, Windermere, FL 34786
/2
$1,258,250 Sold May 29, 2025

1825 Lake Roberts Ct, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,754 Sq Ft
- Built 1995
Last Sold Summary
- $335/SF
- 27 Days On Market
Current Estimated Value $1,248,854

Last Listing Agent Daniel Ryan EXP REALTY LLC

1825 Lake Roberts Ct, Windermere, FL 34786

/71
Est $612,388 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,374 Sq Ft
6769 Merrick Landing Blvd, Windermere, FL 34786

6769 Merrick Landing Blvd, Windermere, FL 34786

/45
$625,000 Pending
- 5 Beds
- 2.5 Baths
- 2,759 Sq Ft
6891 Northwich Dr, Windermere, FL 34786

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Nestled within Lakes of Windermere sits a 5 BEDROOM, 2.5 BATH Craftsman inspired home priced BELOW MARKET VALUE with BRAND NEW HVAC, HOT WATER HEATER, and LVP flooring Upstairs. The welcoming front yard with flowing ground cover, shade providing magnolias, and flowering plants is located just across from the

Ashley Wilt TITAN REALTY GROUP LLC

6891 Northwich Dr, Windermere, FL 34786
/2
$615,000 Sold Jul 30, 2025

12524 Aldershot Ln, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
- Built 2003
Last Sold Summary
- 1% Below List Price
- $250/SF
- 7 Days On Market
Current Estimated Value $611,551

Last Listing Agent Tara Moore TARA MOORE REAL ESTATE

12524 Aldershot Ln, Windermere, FL 34786

/55
Est $1,118,243 Not Listed For Sale
- 6 Beds
- 4.5 Baths
- 4,511 Sq Ft
8388 Lookout Pointe Dr, Windermere, FL 34786

8388 Lookout Pointe Dr, Windermere, FL 34786

/51
$1,629,000 Pending
- 5 Beds
- 3.5 Baths
- 3,967 Sq Ft
6222 Lecco Way, Windermere, FL 34786

Custom Home in Prestigious Waterstone on Lake Butler. This stunning Mizner/Palm Beach–inspired residence offers timeless elegance with stone columns and wrought-iron detailing that welcome you into a private front courtyard—your first outdoor living oasis. Inside, the Grande Room impresses with a fireplace, intricate stone inlays, and a soaring 12-ft stained cypress ceiling. The newly remodeled

Matty Castillo EMPIRE NETWORK REALTY

6222 Lecco Way, Windermere, FL 34786
/2
$375,000 Sold Oct 14, 2025

7819 Hardenton St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
- Built 2012
Last Sold Summary
- 11% Below List Price
- $250/SF
- 144 Days On Market
Current Estimated Value $374,745

Last Listing Agent Cory Prado COLDWELL BANKER REALTY

7819 Hardenton St, Windermere, FL 34786

/43
Est $529,091 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,089 Sq Ft
11560 Charnock Dr, Windermere, FL 34786

11560 Charnock Dr, Windermere, FL 34786

/3
$3,200,000 New Construction
- 4 Beds
- 4.5 Baths
- 3,889 Sq Ft
2 Chase Rd, Windermere, FL 34786

Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property

Matthew Hughes REAL BROKER, LLC

2 Chase Rd, Windermere, FL 34786

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