Windermere, FL Homes

/51
$1,575,000 Open Sun 1PM - 4PM
- 5 Beds
- 3 Baths
- 3,300 Sq Ft
13124 Filly Ct, Windermere, FL 34786

Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As

Marcelo Brandao HOME N OFFICES INTERNATIONAL

13124 Filly Ct, Windermere, FL 34786
/48
$3,000 per month
- 4 Beds
- 2.5 Baths
- 1,638 Sq Ft
- Condo for Rent
14200 Oasis Cove Blvd Unit 3301, Windermere, FL 34786

Amazing opportunity to live in the exclusive and highly desirable Windermere area! This stunning corner townhouse in the sought-after gated community of Oasis Cove features 4 spacious bedrooms and 2.5 bathrooms, offering an abundance of natural light and a functional layout. The home boasts a beautiful lake view that provides a serene backdrop for daily living, complemented by a private fenced

Carola Garcia De Montenegro AGENT TRUST REALTY CORPORATION

14200 Oasis Cove Blvd Unit 3301, Windermere, FL 34786
/2
$730,000 Sold Aug 15, 2025

9025 Horizon Pointe Trail, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,264 Sq Ft
- Built 2014
Last Sold Summary
- 1% Below List Price
- $224/SF
- 19 Days On Market
Current Estimated Value $723,302

Last Listing Agent Erin Fang FLORIDA REALTY INVESTMENTS

9025 Horizon Pointe Trail, Windermere, FL 34786

/2
Est $889,958 Not Listed For Sale

8243 Procida Isle Ln, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,226 Sq Ft
- Built 2018
8243 Procida Isle Ln, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $282/SF
- 81 Days On Market
Last Sold Price $910,000

Last Listing Agent Mariana Haddad LA ROSA REALTY LLC

/60
$795,000 Pending
- 4 Beds
- 2.5 Baths
- 2,766 Sq Ft
12905 Strode Ln, Windermere, FL 34786

Under contract-accepting backup offers. Completely remodeled in 2021! Welcome home to your stunning 4-bedroom craftsman with contemporary finishes in the highly sought after community of Windermere Sound. This well-maintained waterfront home with no rear neighbors has it all. At first glance you will immediately notice the amazing curb appeal with its charming architecture, manicured landscaping,

Simon Simaan THE SIMON SIMAAN GROUP

12905 Strode Ln, Windermere, FL 34786
/37
$3,500 per month
- 4 Beds
- 2.5 Baths
- 3,011 Sq Ft
- House for Rent
12761 Bideford Ave, Windermere, FL 34786

Beautiful 4-bedroom 2.5 bath home located in the desirable Lakes of Windermere community. This two-story corner lot home has everything you can ask for, formal living and dining rooms, kitchen with granite countertops, stainless steel appliances, and a breakfast bar that opens to a large family room, on the first floor you also have a massive master bedroom suite, with a large closet and the

Paul Moscoso Donoso SHINING OAK REALTY

12761 Bideford Ave, Windermere, FL 34786
/2
$330,000 Sold Oct 22, 2025

11565 Mizzon Dr Unit 208, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Built 2006
Last Sold Summary
- 6% Below List Price
- $229/SF
- 10 Days On Market
Current Estimated Value $327,828

Last Listing Agent Gisele Abrantes Trautman DALTON WADE INC

11565 Mizzon Dr Unit 208, Windermere, FL 34786

/37
Est $1,593,396 Not Listed For Sale

1214 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 4.5 Baths
- 4,396 Sq Ft
- Built 2019
1214 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $353/SF
- 39 Days On Market
Last Sold Price $1,550,000

Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

/22
$399,900 Pending
- 3 Beds
- 2.5 Baths
- 1,468 Sq Ft
7361 Brightland St, Windermere, FL 34786

Under contract-accepting backup offers. New Price! Nestled in the heart of Windermere, this two-story townhome is a perfect blend of charm, comfort, and modern living. As you approach, the cute front porch entrance welcomes you, hinting at the warmth that lies within. The exterior is adorned with stone columns and crowned with a stylish barrel-tiled roof, adding character to this inviting abode.

Peter Luu REAL BROKER, LLC

7361 Brightland St, Windermere, FL 34786
/29
$2,650 per month
- 3 Beds
- 2.5 Baths
- 1,690 Sq Ft
- Townhouse for Rent
8973 Matriarca Aly, Windermere, FL 34786

Beautiful two-level end Unit townhouse 3 bedrooms and 2.5 bath in the Legado community of Windermere,42" cabinets with stainless Steel appliance, with attached 2 car garage, beautiful water view at the front,3-minutes' drive to Magic Kingdom and Publix shopping areas, you will enjoy the community pool/Cabana and Playground, Green Parks, Dog Waste Station.

Jiu Feng Wei AAA GLOBAL VENTURES PA

8973 Matriarca Aly, Windermere, FL 34786
/2
$960,000 Sold May 30, 2025

10986 Ledgement Ln Unit 2, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,080 Sq Ft
- Built 2003
Last Sold Summary
- 4% Below List Price
- $312/SF
- 30 Days On Market
Current Estimated Value $950,205

Last Listing Agent Mandy Morgan TEAM DONOVAN

10986 Ledgement Ln Unit 2, Windermere, FL 34786

/62
Est $2,380,954 Not Listed For Sale

13334 Bellaria Cir, Windermere, FL 34786
- 5 Beds
- 7 Baths
- 5,734 Sq Ft
- Built 2014
13334 Bellaria Cir, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $427/SF
- 189 Days On Market
Last Sold Price $2,450,000

Last Listing Agent María Gabriela Lara CENTURY 21 CARIOTI

/50
$1,119,990 New Construction
- 6 Beds
- 4.5 Baths
- 3,692 Sq Ft
14354 Crest Palm Ave, Windermere, FL 34786

TIDEWATER W/BONUS - Our beautiful huge 2 story home, located on a beautiful conservation lot, with 6 Bedrooms and 4.5Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42 wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8 glass enclosure, an additional rainfall shower head, and

Dream Finders Homes Builder

14354 Crest Palm Ave, Windermere, FL 34786
/26
$2,450 per month
- 3 Beds
- 2.5 Baths
- 1,720 Sq Ft
- Townhouse for Rent
7314 Brightland St, Windermere, FL 34786

Experience the beauty and comfort of this stunning 3-bedroom, 2.5-bathroom townhouse in Windermere. With an exceptional layout, all bedrooms are thoughtfully situated upstairs for added privacy. The modern kitchen features upgraded stainless steel appliances, and the home includes a convenient front-loading washer and dryer. Enjoy outdoor living with a charming patio and a detached 2-car garage.

Carissa Lawhun FLORIDA REALTY INVESTMENTS

7314 Brightland St, Windermere, FL 34786
/2
$485,000 Sold Sep 24, 2025

7837 Berkshire Oak Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,904 Sq Ft
- Built 2018
Last Sold Summary
- 1% Below List Price
- $255/SF
- 3 Days On Market
Current Estimated Value $483,197

Last Listing Agent Cara Edwards ALL REAL ESTATE & INVESTMENTS

7837 Berkshire Oak Aly, Windermere, FL 34786

/80
Est $2,486,000 Not Listed For Sale

11628 Waterstone Loop Dr, Windermere, FL 34786
- 5 Beds
- 7 Baths
- 5,161 Sq Ft
- Built 2015
11628 Waterstone Loop Dr, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $475/SF
- 9 Days On Market
Last Sold Price $2,450,000

Last Listing Agent Patricia Mascarenhas Bonina Zimath CHARLES RUTENBERG REALTY ORLANDO

/15
$979,990 New Construction
- 3 Beds
- 2.5 Baths
- 2,226 Sq Ft
Plant at Lake Cawood Cove - Traditional, Windermere, FL 34786

The Plant is a one-story home offering three bedrooms, two full bathrooms, one half bathroom, and a two-car garage. The spacious kitchen features a large island and flows seamlessly into the dining and family rooms. A private primary suite includes a walk-in closet, while a generously sized den and covered lanai provide versatile living spaces for work, relaxation, and outdoor enjoyment. Modern

Ashton Woods Builder

5432 Winter Garden Vineland Rd Unit 37932781, Windermere, FL 34786
/39
$2,750 per month
- 3 Beds
- 2.5 Baths
- 2,028 Sq Ft
- Townhouse for Rent
14235 Desert Haven St Unit 3503, Windermere, FL 34786

Discover the charm of this stunning 3-bedroom, 2.5-bath townhome nestled in the highly sought-after Oasis Cove neighborhood. Boasting 2,000square feet of elegant living space spread over two floors, this home offers an inviting layout perfect for modern living. On the first floor, you’llfind the luxurious master suite with an en-suite bath and a spacious walk-in closet. The open-concept

Joel Ramones KELLER WILLIAMS LEGACY REALTY

14235 Desert Haven St Unit 3503, Windermere, FL 34786
/2
$3,600,000 Sold May 12, 2025

11306 Bridge House Rd, Windermere, FL 34786
- 5 Beds
- 7 Baths
- 6,742 Sq Ft
- Built 2007
Last Sold Summary
- 10% Below List Price
- $534/SF
- 52 Days On Market
Current Estimated Value $3,691,585

Last Listing Agent Loren Williams LAKESIDE REALTY WINDERMERE INC

11306 Bridge House Rd, Windermere, FL 34786

/2
Est $1,353,910 Not Listed For Sale

17550 Black Rail St, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 4,908 Sq Ft
- Built 2015
17550 Black Rail St, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $272/SF
- 44 Days On Market
Last Sold Price $1,335,000

Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

/2
$855,990 New Construction
- 4 Beds
- 2.5 Baths
- 2,712 Sq Ft
Tidewater Plan at Palms at Windermere, Windermere, FL 34786

The Tidewater floorplan offers a versatile and spacious two-story layout, featuring 4 bedrooms and 2.5 bathrooms. Spanning 2,712 sq. ft., this home includes a large two-car garage for ample storage and convenience. The first floor boasts an inviting great room connected to an open kitchen and dining area, perfect for entertaining. The owner’s suite provides a private retreat with a generous

Dream Finders Homes Builder

14207 Crest Palm Ave Unit 36489841, Windermere, FL 34786
/45
$2,900 per month
- 3 Beds
- 2.5 Baths
- 2,203 Sq Ft
- House for Rent
13040 Overstreet Rd, Windermere, FL 34786

$500 OFF BEFORE MOVING IN 03/31/2026!!! Beautiful 3-Bedroom Home in Windermere Sound – Prime Location with Top-Rated Schools. Owner spent more than 10K to upgrade and add a screened porch! Welcome to this gorgeous 3-bedroom single-family home located in the highly desirable Windermere Sound community, known for its top-rated schools and exceptional lifestyle. This home offers the perfect blend of

Amanda Yuan MULTI CHOICE REALTY LLC

13040 Overstreet Rd, Windermere, FL 34786
/2
$742,000 Sold Jun 02, 2025

12971 Westside Village Loop, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,694 Sq Ft
- Built 2018
Last Sold Summary
- 1% Below List Price
- $201/SF
- 72 Days On Market
Current Estimated Value $762,521

Last Listing Agent Eric Jia NUMBER 1 BROKER, LLC

12971 Westside Village Loop, Windermere, FL 34786

/34
Est $520,990 Not Listed For Sale

13335 Overstreet Rd, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
- Built 2013
13335 Overstreet Rd, Windermere, FL 34786

Last Sold Summary
- 2% Below List Price
- $258/SF
- 6 Days On Market
Last Sold Price $530,000

Last Listing Agent Ryan Langley FLORIDA REALTY INVESTMENTS

/64
$2,100,000
- 6 Beds
- 5.5 Baths
- 5,430 Sq Ft
9057 Balmoral Mews Square, Windermere, FL 34786

Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath luxury estate sits on an expansive 3⁄4-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water fountain,

Ryan Rogers REAL BROKER, LLC

9057 Balmoral Mews Square, Windermere, FL 34786
/28
$2,775 per month
- 3 Beds
- 2.5 Baths
- 2,332 Sq Ft
- Townhouse for Rent
13841 Ancilla Blvd, Windermere, FL 34786

AVAILABLE AFTER APRIL 10TH. Spacious 3/2.5 townhouse, located in Summerport Community in Windermere! Summerport Community offers residents a pool, fitness center, volleyball courts, tennis courts, playground, and clubhouse. This 2-story townhome provides a warm welcome, with a paved walkway leading to a cozy front porch area for relaxation. The interior has been painted a lovely neutral gray

Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

13841 Ancilla Blvd, Windermere, FL 34786
/2
$700,000 Sold Feb 13, 2026

9792 Wild Oak Dr, Windermere, FL 34786
- 3 Beds
- 3.5 Baths
- 3,102 Sq Ft
- Built 1982
Last Sold Summary
- 26% Below List Price
- $226/SF
- 106 Days On Market
Current Estimated Value $881,311

Last Listing Agent Suzette Berkhalter KELLER WILLIAMS ADVANTAGE III

9792 Wild Oak Dr, Windermere, FL 34786

/22
Est $1,022,829 Not Listed For Sale

12525 Montalcino Cir, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 3,117 Sq Ft
- Built 2013
12525 Montalcino Cir, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $317/SF
- 20 Days On Market
Last Sold Price $989,000

Last Listing Agent MELANIE BIGIO OLYMPUS EXECUTIVE REALTY INC

/61
$499,000
- 4 Beds
- 2.5 Baths
- 2,092 Sq Ft
10624 Reams Rd, Windermere, FL 34786

Welcome to this beautiful 4-bedroom, 2.5-bath home in the highly desirable Windermere Trails community. Just minutes from Disney World, you can enjoy nightly fireworks right from your front porch. The kitchen features 42" maple cabinets, granite countertops, and under-cabinet lighting. An open-concept design connects the spacious living and with the kitchen, perfect for entertaining. The primary

Jeff Taulbee CHARLES RUTENBERG REALTY ORLANDO

10624 Reams Rd, Windermere, FL 34786
/13
$2,250 per month
- 2 Beds
- 1 Bath
- 891 Sq Ft
- House for Rent
721 Magnolia St, Windermere, FL 34786

This Charming Fully Renovated Home is available for rent in the Heart of Downtown Windermere Welcome to this beautifully remodeled 2-bedroom, 1-bathroom gem, ideally located within short distance to the vibrant shops, restaurants, and parks of downtown Windermere, as well as the scenic Chain of Lakes. Step inside to discover a fresh, modern interior where everything is brand new—from the sleek

Ronald Fuenmayor EXP REALTY LLC

721 Magnolia St, Windermere, FL 34786
/2
$1,050,000 Sold Oct 31, 2025

65 Oakdale St, Windermere, FL 34786
- 4 Beds
- 2 Baths
- 2,191 Sq Ft
- Built 1959
Last Sold Summary
- 12% Below List Price
- $479/SF
- 34 Days On Market
Current Estimated Value $1,086,601

Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

65 Oakdale St, Windermere, FL 34786

/40
Est $531,654 Not Listed For Sale

12160 Canyon Sun Trail, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,184 Sq Ft
- Built 2015
12160 Canyon Sun Trail, Windermere, FL 34786

Last Sold Summary
- 6% Below List Price
- $259/SF
- 2 Days On Market
Last Sold Price $565,000

Last Listing Agent Pilar Fernandez SIX STAR REALTY GROUP LLC

/30
$649,000
- 3 Beds
- 2 Baths
- 2,147 Sq Ft
13622 Darchance Rd, Windermere, FL 34786

Welcome home to Berkshire Park. This 3bedroom, 2bath residence offers a balance of comfort and convenience in a quiet residential setting. Ideally located just minutes from world-class attractions including Walt Disney World, as well as shopping, dining, and major highways, this property places you at the center of Central Florida living. The community is surrounded by nearby schools, adding

Javin Lopez AVANTI WAY REALTY LLC

13622 Darchance Rd, Windermere, FL 34786
/33
$2,775 per month
- 2 Beds
- 2 Baths
- 1,155 Sq Ft
- Townhouse for Rent
13845 Ancilla Blvd, Windermere, FL 34786

Welcome to this beautifully updated corner-unit townhome, offering the perfect blend of comfort, convenience, and stunning views. Featuring 2 spacious bedrooms, 2 bathrooms, and a host of desirable features, this home is a true gem. Interior Highlights:- Neutrally painted interior, creating a bright and inviting ambiance- A fully equipped kitchen with all appliances included, ready for

Francisco Nieves-Taranto CT HOMES REALTY CORPORATION

13845 Ancilla Blvd, Windermere, FL 34786
/2
$1,295,922 Sold Mar 31, 2025

14207 Crest Palm Ave, Windermere, FL 34786
- 6 Beds
- 4 Baths
- 4,222 Sq Ft
- Built 2024
Last Sold Summary
- $307/SF
- 0 Days On Market
Current Estimated Value $1,212,000

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14207 Crest Palm Ave, Windermere, FL 34786

/40
Est $638,514 Not Listed For Sale

7230 Rambling Water Way, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,208 Sq Ft
- Built 2016
7230 Rambling Water Way, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $281/SF
- 18 Days On Market
Last Sold Price $620,000

Last Listing Agent Heather Spirazza REGENCY REAL ESTATE LLC

/27
$485,000 Pending
- 4 Beds
- 3 Baths
- 1,980 Sq Ft
7028 Ventnor Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. PRISTINE 4 Bedroom 3 Bath End Unit Townhome in Beautiful Preston Square Windermere with Brand New Roof and exterior paint. Charming Front Porch invites you into this fabulous two-story home. Lots of Natural light with wrap around windows and 10-foot ceilings. Stunning hardwood floors, new 6” baseboards in main living areas. Family Room has a stylish

Amanda Black PA UPSIDE REAL ESTATE INC

7028 Ventnor Dr, Windermere, FL 34786
/61
$6,995 per month
- 5 Beds
- 4 Baths
- 3,694 Sq Ft
- House for Rent
3265 Hidden Lake Dr, Winter Garden, FL 34787

Rarely Available Lakefront Boater's Dream in Winter Garden/Windermere area at an amazing price! This home sits on a massive 1.5+ acre lot on the waterfront of Lake Roper. The home is a sprawling 3700 SF one story home with extremely high ceilings. The main room is an enormous Great room plan combining the Kitchen, Living Great room, Formal Dining Room and Office flex room ALL overlooking the

Billy Cannon, Jr BHHS FLORIDA REALTY

3265 Hidden Lake Dr, Winter Garden, FL 34787
/2
$890,000 Sold Jul 31, 2025

235 Oakdale St, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 2,562 Sq Ft
- Built 1971
Last Sold Summary
- 11% Below List Price
- $347/SF
- 274 Days On Market
Current Estimated Value $913,375

Last Listing Agent Simon Simaan THE SIMON SIMAAN GROUP

235 Oakdale St, Windermere, FL 34786

/67
Est $1,562,197 Not Listed For Sale

1220 Estancia Woods Loop, Windermere, FL 34786
- 4 Beds
- 5 Baths
- 4,007 Sq Ft
- Built 2018
1220 Estancia Woods Loop, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $381/SF
- 72 Days On Market
Last Sold Price $1,525,000

Last Listing Agent Angela Rodriguez DREAM FINDERS REALTY GROUP CORP

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