Windermere, FL Homes

/37
$1,298,000 Pending
- 4 Beds
- 3.5 Baths
- 3,751 Sq Ft
6533 Cartmel Ln, Windermere, FL 34786

Under contract-accepting backup offers. Tucked away in the prestigious guard-gated community of The Reserve at Lake Butler Sound, this exceptional 4-bedroom, 3.5-bath single-storypool home blends timeless Mediterranean style with modern sophistication. Set on over half an acre in a quiet cul-de-sac, the home welcomesyou with a paver driveway, lush mature landscaping, and an elegant entry

Andy Neal THE AGENCY FL

6533 Cartmel Ln, Windermere, FL 34786
/31
$2,400 per month
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
- Townhouse for Rent
8145 Serenity Spring Dr Unit GE, Windermere, FL 34786

Beautiful townhome 3 BED, 2.5 BATH, 1 CAR GARAGE in resort style gated community. Stainless steel kitchen appliances, washer & dryer, upgraded wood cabinets, granite kitchen counter tops. All three bedrooms are upstairs, where there is carpet in the bedrooms and tile in the bathrooms & laundry. The community offers a community resort pool, fitness center, large pond with walking trails around the

Isabel Sirizzotti SUNNY 365 REALTY GROUP

8145 Serenity Spring Dr Unit GE, Windermere, FL 34786
/2
$1,000,000 Sold Sep 03, 2025

1947 Broadleaf Ct, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,646 Sq Ft
- Built 1989
Last Sold Summary
- 20% Below List Price
- $274/SF
- 64 Days On Market
Current Estimated Value $986,746

Last Listing Agent Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

1947 Broadleaf Ct, Windermere, FL 34786

/58
Est $609,420 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

Last Listing Agent Isabel Sirizzotti SUNNY 365 REALTY GROUP

/3
$1,174,935 Pending
- 4 Beds
- 3 Baths
- 3,100 Sq Ft
14250 Crest Palm Ave, Horizon West, FL 34786

One or more photo(s) has been virtually staged. Under Construction. Sample Image Experience the perfect blend of elegance, comfort, and practicality with this beautifully crafted new home in Windermere. Every element of this residence has been thoughtfully designed to create a space that feels both luxurious and inviting. With soaring ceilings—up to 10 feet on the first floor and 9 feet on the

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14250 Crest Palm Ave, Horizon West, FL 34786
/47
$9,999 per month
- 3 Beds
- 3 Baths
- 3,255 Sq Ft
- House for Rent
5243 W Lake Butler Rd, Windermere, FL 34786

Experience Lakefront Luxury Living - where every day feels like a vacation. Prepare to be captivated by this fully renovated three-bedroom, three-bath lakefront home on the highly sought-after Lake Butler. Part of the Butler Chain of Lakes, featuring 13 connected lakes. A true retreat that blends resort-style amenities with refined design. Nestled on pristine waterfront, this property offers

Steve Simpson 407 PROPERTIES

5243 W Lake Butler Rd, Windermere, FL 34786
/2
$840,000 Sold Oct 17, 2025

4509 Indian Deer Rd, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,412 Sq Ft
- Built 2006
Last Sold Summary
- 1% Below List Price
- $348/SF
- 10 Days On Market
Current Estimated Value $817,463

Last Listing Agent Clementine Costantini KELLER WILLIAMS REALTY AT THE LAKES

4509 Indian Deer Rd, Windermere, FL 34786

/51
Est $838,506 Not Listed For Sale

4240 Blue Major Dr, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,345 Sq Ft
- Built 2015
4240 Blue Major Dr, Windermere, FL 34786

Last Sold Summary
- 10% Below List Price
- $277/SF
- 55 Days On Market
Last Sold Price $928,000

Last Listing Agent Adriana Muzzi WRA BUSINESS & REAL ESTATE

/32
$1,495,000 Open Sun 2PM - 5PM
- 6 Beds
- 4.5 Baths
- 5,316 Sq Ft
17521 Black Rail St, Windermere, FL 34786

*** Now priced under $1.5M offering strong value at approximately $281/SF compared to similar Windermere homes*** PRIME opportunity for a LIKE NEW spacious MOVE-IN READY Windermere pool home just 1.5 miles from Windermere Preparatory School, and conveniently located near other top-rated public and private schools. Offering over 5,300 sq ft of thoughtfully designed living space, this 6 bedroom/4.5

Rebecca Puig CHARLES RUTENBERG REALTY ORLANDO

17521 Black Rail St, Windermere, FL 34786
/20
$2,750 per month
- 3 Beds
- 2.5 Baths
- 1,912 Sq Ft
- Townhouse for Rent
13718 Beckman Dr, Windermere, FL 34786

Beautiful TOWHOME AT WINDERMERE AREA. kitchen with upgraded 42`` cabinets, stainless steel appliances. Upstairs vinyl floor, Master suite with walk in closet ,bathroom with dual sinks. Club house with pool.

Monica Duran MD3 HOMES LLC

13718 Beckman Dr, Windermere, FL 34786
/2
$315,000 Sold Nov 14, 2025

8271 Maritime Flag St Unit 109, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,363 Sq Ft
- Built 2011
Last Sold Summary
- 12% Below List Price
- $231/SF
- 155 Days On Market
Last Listing Agent Daniela de Rodriguez B LIVE COMMERCIAL AND RESIDENT

8271 Maritime Flag St Unit 109, Windermere, FL 34786

/16
Est $324,526 Not Listed For Sale

11564 Mizzon Dr Unit 904, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
- Built 2006
11564 Mizzon Dr Unit 904, Windermere, FL 34786

Last Sold Summary
- 14% Below List Price
- $260/SF
- 1 Day On Market
Last Sold Price $379,000

Last Listing Agent Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

/39
$1,400,000
- 5 Beds
- 4.5 Baths
- 4,257 Sq Ft
11044 Hawkshead Ct Unit 2, Windermere, FL 34786

Stunning home in the Reserve at Lake Butler Sound-Windermere. This luxury living at its finest located in the prestigious 24 hour guarded community. The property features 5 bedrooms, 4.5 bathrooms, a 3-car garage, and a private heated pool, perfect for relaxing or entertaining. The owner has invested more than $100,000 upgrades..... newly renovated kitchen boasts brand new cabinetry and

Jennie Ho MAY HO REALTY

11044 Hawkshead Ct Unit 2, Windermere, FL 34786
/18
$2,800 per month
- 4 Beds
- 2.5 Baths
- 1,997 Sq Ft
- Townhouse for Rent
7681 Fordson Ln, Windermere, FL 34786

Experience modern, energy-efficient living with SOLAR PANELS that provide sustainable power and an exceptionally low electric bill! This beautiful townhome for rent is located in the highly desirable community of Windermere Sound. Offering 4 bedrooms and 2.5 bathrooms, this spacious property features ceramic tile flooring in the main areas and carpet in the bedrooms for added comfort. The open

Reina Mendez REILE REALTY CORP

7681 Fordson Ln, Windermere, FL 34786
/32
$575,000 Sold May 15, 2025

5140 Honeynut Ln, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,819 Sq Ft
- Built 1987
Last Sold Summary
- 4% Below List Price
- $316/SF
- 35 Days On Market
Current Estimated Value $573,373

Last Listing Agent Daniel Waldron MAINFRAME REAL ESTATE

5140 Honeynut Ln, Windermere, FL 34786

/46
Est $1,163,455 Not Listed For Sale

7219 Sangalla Dr, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 3,818 Sq Ft
- Built 2012
7219 Sangalla Dr, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $300/SF
- 6 Days On Market
Last Sold Price $1,145,000

Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

/36
$1,349,000 Pending
- 4 Beds
- 3 Baths
- 2,937 Sq Ft
5837 Caymus Loop, Windermere, FL 34786

Under contract-accepting backup offers. Completely renovated and thoughtfully reconfigured in 2023, this stunning 4-bedroom, 3-bath home is located in the highly sought-after, 24-hour gated and guarded community of Keene’s Pointe. Designed for modern living, the home features an open and refreshed layout with new flooring throughout and elegant paneling details that elevate the interior design.

Jay Stewart SOUTHERN REALTY GROUP LLC

5837 Caymus Loop, Windermere, FL 34786
/61
$4,475 per month
- 6 Beds
- 3.5 Baths
- 3,764 Sq Ft
- House for Rent
14415 Crest Palm Ave, Windermere, FL 34786

Be the First to Call This Home Yours! Brand New Luxurious 2025! Move-In Ready! Pet Friendly! 2-Car Garage! Smart Home! Stunning 6 Bedrooms, Loft, Bonus Room, Stylish Upgrades! Internet & WiFi Included! Step into luxurious, modern living in this expansive 6-bedroom, 3.5-bath, two-story smart home featuring a bright, open-concept layout that seamlessly connects the gourmet kitchen, family room, and

Katrina Anarumo RENT A FLORIDA HOME

14415 Crest Palm Ave, Windermere, FL 34786
/2
$2,075,000 Sold Feb 09, 2026

647 Ridgewood Dr, Windermere, FL 34786
- 3 Beds
- 3 Baths
- 2,681 Sq Ft
- Built 1974
Last Sold Summary
- 12% Below List Price
- $774/SF
- 373 Days On Market
Current Estimated Value $2,173,832

Last Listing Agent Linda O'Grady PREMIER SOTHEBYS INT'L REALTY

647 Ridgewood Dr, Windermere, FL 34786

/43
Est $2,801,166 Not Listed For Sale

13100 Bellaria Cir, Windermere, FL 34786
- 6 Beds
- 6.5 Baths
- 6,011 Sq Ft
- Built 2012
13100 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $457/SF
- 40 Days On Market
Last Sold Price $2,750,000

Last Listing Agent Leonardo Pereira KAZA REAL ESTATE LLC

$1,166,989 New Construction
- 6 Beds
- 4 Baths
- 3,550 Sq Ft
14383 Crest Palm Ave, Windermere, FL 34786

ELLINGTON II - Our beautiful huge 2 story home, with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area along with a formal dining room, gourmet kitchen, extended 42 cabinets and an extended island. Primary Suite on 1st floor along with an additional bedroom & bath. The primary bath also contains a spa package with upgraded 3/8 glass enclosure, an

Dream Finders Homes Builder

14383 Crest Palm Ave, Windermere, FL 34786
/7
$1,275 per month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- House for Rent
2156 Merrybells Dr, Kissimmee, FL 34746

Welcome to this beautifully appointed mother-in-law suite featuring a spacious bedroom with ample natural light, a full bathroom, and a separate living area ideal for relaxing or entertaining. The suite also includes a kitchenette with modern cabinetry, a dedicated entrance for added privacy, and direct access to the main home when desired. Thoughtfully designed with neutral finishes and tile

Mayling Marrero KELLER WILLIAMS ADVANTAGE III

2156 Merrybells Dr, Kissimmee, FL 34746
/2
$330,000 Sold Jul 16, 2025

14320 Desert Haven St Unit 3906, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
- Built 2012
Last Sold Summary
- 3% Below List Price
- $179/SF
- 94 Days On Market
Current Estimated Value $336,966

Last Listing Agent Vicente Virgilio ALTIS REALTY

14320 Desert Haven St Unit 3906, Windermere, FL 34786

/2
Est $821,650 Not Listed For Sale

13303 Roskin Ln, Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 3,609 Sq Ft
- Built 2011
13303 Roskin Ln, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $236/SF
- 70 Days On Market
Last Sold Price $850,000

Last Listing Agent Margaret Gay THREE MOUNTAINS REALTY

/35
$1,350,000 Pending
- 4 Beds
- 3 Baths
- 3,888 Sq Ft
10506 Down Lakeview Cir, Windermere, FL 34786

Under contract-accepting backup offers. Welcome Home to “The Lakes” — Windermere’s Hidden GemTucked away in the ultra-private The Lakes community of Windermere, this beautiful residence sits on a rare 1-acre lot with breathtaking views of Lake Down, part of the renowned Butler Chain of Lakes.With just 60 homes in the entire neighborhood, exclusivity and serenity come standard. Picture

Obdulia Dobbins LA ROSA REALTY LLC

10506 Down Lakeview Cir, Windermere, FL 34786
/42
$17,950 per month
- 6 Beds
- 8 Baths
- 6,881 Sq Ft
- House for Rent
3999 Isabella Cir, Windermere, FL 34786

Exquisite Luxury Retreat in Prime Windermere Location Welcome to 3999 Isabella Cir, an architectural masterpiece nestled within the prestigious community of Casabella at Windermere, FL. This opulent estate is a true embodiment of refined living, offering a harmonious blend of elegant design, impeccable craftsmanship, and unparalleled comfort. Situated on an expansive half acre lot, this

Lucas DeSouza DELUCA REAL ESTATE SERVICES CORP

3999 Isabella Cir, Windermere, FL 34786
/2
$370,000 Sold Feb 03, 2026

5235 Keenes Pheasant Dr, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,462 Sq Ft
- Built 2004
Last Sold Summary
- 14% Below List Price
- $253/SF
- 186 Days On Market
Current Estimated Value $370,091

Last Listing Agent Ronda Shively COMPASS FLORIDA LLC

5235 Keenes Pheasant Dr, Windermere, FL 34786

/2
Est $329,648 Not Listed For Sale

8259 Maritime Flag St Unit 6, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,460 Sq Ft
- Built 2011
8259 Maritime Flag St Unit 6, Windermere, FL 34786

Last Sold Summary
- 4% Below List Price
- $236/SF
- 94 Days On Market
Last Sold Price $345,000

Last Listing Agent Hortencia Aponte LPT REALTY, LLC

/51
$840,646 Pending
- 5 Beds
- 4.5 Baths
- 3,849 Sq Ft
4926 Indian Deer Rd, Windermere, FL 34786

Under contract-accepting backup offers. WOW! Check out this stunningly renovated Summerport multi-generational home! This expansive residence features 4 spacious bedrooms and 3 baths, PLUS a private multigenerational suite on the first floor complete with its own bedroom, full bath, and sitting area overlooking the serene pond.Designed with both comfort and versatility in mind, the home

Shelley Dawson COMPASS FLORIDA LLC

4926 Indian Deer Rd, Windermere, FL 34786
/50
$5,800 per month
- 3 Beds
- 2 Baths
- 1,725 Sq Ft
- House for Rent
12860 Lake Sawyer Ln, Windermere, FL 34786

Private LAKEFRONT estate home on that sits on almost 2 acres of land, gated for extreme privacy! Fully furnished with an open floorplan great for families and entertaining. This home features 3 cozy bedrooms with a king, queen, and full bed to accommodate all guests comfortably. Enjoy the convenience of 2 bathrooms, one with a relaxing jetted bathtub. Kitchen features butcher block countertops,

Aleem Kanji CROWN REALTY COMPANY

12860 Lake Sawyer Ln, Windermere, FL 34786
/2
$830,000 Sold Feb 27, 2026

9495 Westover Club Cir, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,773 Sq Ft
- Built 2001
Last Sold Summary
- 2% Below List Price
- $299/SF
- 3 Days On Market
Current Estimated Value $814,599

Last Listing Agent Jeff Powell ALL FLORIDA PREMIER REALTY GROUP LLC

9495 Westover Club Cir, Windermere, FL 34786

/37
Est $342,461 Not Listed For Sale

8259 Maritime Flag St Unit 1, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,601 Sq Ft
- Built 2011
8259 Maritime Flag St Unit 1, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $219/SF
- 85 Days On Market
Last Sold Price $350,000

Last Listing Agent Fernando Zucato CHARLES RUTENBERG REALTY ORLANDO

/78
$3,499,999
- 5 Beds
- 4.5 Baths
- 4,417 Sq Ft
5001 Latrobe Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. Don’t miss this rare opportunity to own a stunning estate home in the prestigious Isleworth Golf & Country Club, perfectly positioned on a quiet cul-de-sac along the 6th fairway with serene views of Lake Bessie. Offering 4,417 square feet of refined living space, this elegant two-story residence features five spacious bedrooms, four-and-a-half

Laura Diss Q BOUTIQUE SPECIALTY REALTY INC

5001 Latrobe 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
$418,000 Sold Jun 18, 2025

11746 Water Run Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,588 Sq Ft
- Built 2016
Last Sold Summary
- 4% Below List Price
- $263/SF
- 10 Days On Market
Current Estimated Value $415,489

Last Listing Agent Kris Ibrahim HOME WISE REALTY GROUP, INC.

11746 Water Run Aly, Windermere, FL 34786

/2
Est $1,192,145 Not Listed For Sale

6228 Roseate Spoonbill Dr, Windermere, FL 34786
- 8 Beds
- 5 Baths
- 4,751 Sq Ft
- Built 2012
6228 Roseate Spoonbill Dr, Windermere, FL 34786

Last Sold Summary
- 1% Below List Price
- $253/SF
- 201 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Camila Castrillon COLDWELL BANKER REALTY

/26
$1,000,000
- Land
- 0.5 Acre
- $2,000,000 per Acre
2504 Windermere Reserve Ct, Windermere, FL 34786

Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of

Carolina Dumit CORCORAN PREMIER REALTY

2504 Windermere Reserve Ct, 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
$1,435,000 Sold Nov 12, 2025

1450 Belfiore Way, Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 4,477 Sq Ft
- Built 2007
Last Sold Summary
- 4% Below List Price
- $321/SF
- 109 Days On Market
Current Estimated Value $1,401,608

Last Listing Agent Laura Teixeira NOBSKA REAL ESTATE LLC

1450 Belfiore Way, Windermere, FL 34786

/2
Est $290,636 Not Listed For Sale

11446 Jasper Kay Terrace Unit 1012, Windermere, FL 34786
- 2 Beds
- 2 Baths
- 1,161 Sq Ft
- Built 2007
11446 Jasper Kay Terrace Unit 1012, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $258/SF
- 130 Days On Market
Last Sold Price $300,000

Last Listing Agent Mark Bridges CHARLES RUTENBERG REALTY ORLANDO

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