Windermere, FL Homes

/60
$2,799,000
- 4 Beds
- 3.5 Baths
- 5,764 Sq Ft
13025 Water Point Blvd, Windermere, FL 34786

Waterford Pointe - highly sought after gated/attended community in Windermere. This award winning Mediterranean design with nearly 200 feet of commanding water frontage on Lake Roberts boasts panoramic lake views from nearly every room. Entertaining is ideal for intimate gatherings yet amply appointed for elegant affairs, both inside and poolside! Entering through the leaded glass double doors

Teresa Stewart SOUTHERN REALTY GROUP LLC

13025 Water Point Blvd, Windermere, FL 34786
/36
$5,550 per month
- 4 Beds
- 4 Baths
- 3,730 Sq Ft
- House for Rent
11349 Shandon Park Way, Windermere, FL 34786

One or more photo(s) has been virtually staged. Available Now! Luxurious + Spacious POOL home with 3-car garage located in the 24 hour GUARD GATED community of Reserve at Belmere in Windermere. Situated on a premium corner lot with a big yard and screened in pool area that is perfect for entertaining and all kinds of outdoor activities. Meticulously landscaped - both lawn and pool maintenance are

Brian Lemay ROMAN REALTY GROUP, LLC

11349 Shandon Park Way, Windermere, FL 34786
/2
$653,250 Sold Mar 28, 2025
- 2,463 Sq Ft
- $265/SF
- 9 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2018
12761 Westside Village Loop, Windermere, FL 34786

come take look this newly build energy efficient home by Meritage , spacious 3 bedroom 2.5 bath house with office and the den 3 car garage just installed the vinyl plank floor at the living area beautiful tile roof with charming front porch for you to have morning coffee , once step in , the private office on your right , and walk in you will see the beautiful kitchen with beautiful counter top

Eric Jia NUMBER 1 BROKER, LLC

12761 Westside Village Loop, Windermere, FL 34786

/16
Est $355,542 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
14214 Desert Haven St Unit 3604, Windermere, FL 34786

14214 Desert Haven St Unit 3604, Windermere, FL 34786

/35
$475,000
- 3 Beds
- 2.5 Baths
- 1,760 Sq Ft
8643 Coventry Park Way, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to this beautifully updated townhome in the highly sought-after Windermere Trails community. Perfectly positioned across from a tranquil water view, this home invites you to enjoy peaceful mornings by the pond and magical evenings watching a full display of Disney fireworks.Inside, you'll find a spacious and flexible floor plan. A front flex

Tala Nijmeh COLDWELL BANKER REALTY

8643 Coventry Park Way, Windermere, FL 34786
/22
$2,850 per month
- 3 Beds
- 2.5 Baths
- 1,588 Sq Ft
- Townhouse for Rent
7242 Shadeview Alley, Windermere, FL 34786

Modern 3-Bedroom Townhouse in Windermere’s Ashlin Park – Available July 1st!Discover stylish living in this nearly new 3-bedroom, 2.5-bathroom townhouse, nestled in the highly sought-after Ashlin Park Community in Windermere. Designed with an open floor plan, this home boasts wood-look laminate flooring throughout, and abundant natural light.The heart of the home is the spacious

Brynn Munro CORCORAN PREMIER REALTY

7242 Shadeview Alley, Windermere, FL 34786
/2
$485,000 Sold Mar 28, 2025
- 2,093 Sq Ft
- $232/SF
- 34 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2019
13805 Bressler Alley, Windermere, FL 34786

Welcome to your dream home in Windermere! Nestled in the highly sought-after Vineyards of Horizon West, this stunning townhome combines contemporary style with resort-inspired living. The bright, open floor plan is flooded with natural light, creating a seamless flow between the spacious living, dining, and kitchen areas. The gourmet kitchen is a chef’s delight, featuring high-end appliances,

Kenneth Wilder CREEGAN GROUP

13805 Bressler Alley, Windermere, FL 34786

/60
Est $744,589 Not Listed For Sale
- 5 Beds
- 4 Baths
- 3,365 Sq Ft
13431 Swansea Ave, Windermere, FL 34786

13431 Swansea Ave, Windermere, FL 34786

/39
$1,050,000
- 3 Beds
- 2.5 Baths
- 2,614 Sq Ft
6037 Caymus Loop, Windermere, FL 34786

Tucked behind the gates of Windermere’s coveted Keene’s Pointe, this reimagined Key West-style home sits gracefully on a quiet cul-de-sac, overlooking the 14th fairway of The Golden Bear Club. With a fresh, sophisticated update that includes new flooring, trim, paint, lighting, and more, the home feels both refined and relaxed, like your favorite boutique hotel, only better. Spanning over 2,600

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

6037 Caymus Loop, Windermere, FL 34786
/20
$4,000 per month
- 3 Beds
- 2 Baths
- 1,784 Sq Ft
- House for Rent
415 E 6th Ave, Windermere, FL 34786

Stunning 3 bedroom, 2 bath pool home in the heart of Windermere is available for lease. This beauty features an open and modern floor plan. Beautifully appointed kitchen boasts sleek marble counter tops, a huge kitchen island and high end appliances. Wood floors thought-out home. Living area includes a wood-burning fireplace, large wall to wall sliding glass doors over looking a screened in salt

Cristina Porretto THE AGENCY ORLANDO

415 E 6th Ave, Windermere, FL 34786
/2
$1,123,743 Sold Mar 28, 2025
- 3,764 Sq Ft
- $299/SF
- 87 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2025
14304 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Under Construction. A Perfect Balance of Private and Social SpacesStep into a world where every square foot serves a purpose. The Deerfield's first floor showcases a luxurious primary suite, offering a peaceful retreat complete with a spa-inspired bathroom and generous walk-in closet. Your private home office provides the ideal setting for

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14304 Crest Palm Ave, Windermere, FL 34786

/40
Est $805,613 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,304 Sq Ft
8705 Lookout Pointe Dr, Windermere, FL 34786

8705 Lookout Pointe Dr, Windermere, FL 34786

/8
$899,000
- 4 Beds
- 3 Baths
- 2,748 Sq Ft
9538 Lavill Ct, Windermere, FL 34786

LOCATION, LOCATION, LOCATION!!! Seize this opportunity to REMODEL or REBUILD on this rare ONE-ACRE estate located in LAKE DOWN VILLAGE in renowned WINDERMERE. FLORIDA. Current 4br/3ba pool home has GREAT POTENTIAL, however it is in need a new vision and caring family. Grab your Architect and favorite GC and create your own masterpiece today!

Jim Kernohan SOUTHERN HERITAGE REALTY, INC

9538 Lavill Ct, Windermere, FL 34786
/25
$2,695 per month
- 3 Beds
- 2 Baths
- 1,492 Sq Ft
- House for Rent
9142 Sabal Palm Cir, Windermere, FL 34786

This recently remodeled HOME has 3-bedroom, 2-bathroom with spacious open living area, perfect for entertaining and everyday comfort. Inside, you'll find elegant ceramic tile flooring, adding a sleek and modern touch throughout the home. The kitchen is equipped with granite countertops and stainless-steel appliances. The primary bedroom offers a private retreat with a well-appointed bathroom,

Johany Utrera AVID REALTY LLC

9142 Sabal Palm Cir, Windermere, FL 34786
/2
$1,058,044 Sold Mar 28, 2025
- 3,764 Sq Ft
- $281/SF
- 50 Days On Market
- 5 Beds
- 3.5 Baths
- Built 2025
14409 Crest Palm Ave, Windermere, FL 34786

Under Construction. SAMPLE IMAGE The Deerfield floorplan is a spacious two-story home designed for growing families, featuring 5 bedrooms and 3.5 bathrooms. This layout offers an ideal combination of private retreats and open gathering spaces. The first floor includes the primary bedroom suite, complete with a luxurious bathroom and walk-in closet, a separate study perfect for working from home,

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14409 Crest Palm Ave, Windermere, FL 34786

/2
Est $514,275 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,211 Sq Ft
7742 Brofield Ave, Windermere, FL 34786

7742 Brofield Ave, Windermere, FL 34786

/51
$1,149,000 Open Sat 1PM - 3PM
- 5 Beds
- 3.5 Baths
- 3,210 Sq Ft
2138 Kane Park Way, Windermere, FL 34786

Nestled in the heart of The Willows at Lake Rhea, this breathtaking 5-bedroom, 3.5-bath POOL home sits on a spacious .60-Acre Cul-De-Sac lot, offering both privacy (green area across the street) and a serene pond view. From the moment you walk through the LEADED GLASS DOUBLE FRONT DOORS, you're greeted with A MASIVE WINDOW That Frames the Sparkling SOLAR-HEATED Pool, GAS-HEATED POOL SPA,

Adam Eisen PLATINUM REALTY GROUP FLORIDA INC

2138 Kane Park Way, Windermere, FL 34786
/37
$2,450 per month
- 3 Beds
- 2.5 Baths
- 1,516 Sq Ft
- Townhouse for Rent
12315 Langstaff Dr, Windermere, FL 34786

Charming 3 Bed, 2.5 Bath Townhouse in Windermere Located in the desirable Lake Ream Townhouse subdivision by Ashton Woods Homes, this pristine townhouse offers the perfect blend of comfort and convenience. Zoned for A-RATED schools! Key Features: Fresh and Modern: New carpet, fresh new paint, and recently cleaned A/C with sanitized ducts. Kitchen Delight: Stainless steel appliances, granite

Michael Wald MASTER INTERNATIONAL REALTY GR

12315 Langstaff Dr, Windermere, FL 34786
/2
$485,000 Sold Mar 28, 2025
- 2,092 Sq Ft
- $232/SF
- 170 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2014
10710 Reams Rd, Windermere, FL 34786

LOCATION, LOCATION, LOCATION!!! Beautiful and cozy residence located in the desirable WINDERMERE area. This single-family - bungalow style home offers four bedrooms, two-and-a-half baths and a two-car garage. There's a LOFT UPSTAIRS, perfect for a TV or office/study room. With an open floor plan and ENERGY-EFFICIENT built, the kitchen features stainless steel appliances, overlooking the family

Huafeng Fang MAGICMIND REALTY LLC

10710 Reams Rd, Windermere, FL 34786

/20
Est $479,282 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,912 Sq Ft
13731 Beringer St, Windermere, FL 34786

13731 Beringer St, Windermere, FL 34786

/42
$895,000
- 4 Beds
- 3 Baths
- 2,823 Sq Ft
9248 Legado Dr, Windermere, FL 34786

WOW! Don’t miss this stunning 4 bedroom / 3 bathroom home tucked away on a quiet cul-de-sac with no rear neighbors and incredible fireworks views! This beautifully maintained Windermere home in the Legado neighborhood offers the perfect blend of comfort, privacy, and entertainment-ready features. From the moment you step inside, you’ll feel welcomed by the warm and open layout, complete with a

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

9248 Legado Dr, Windermere, FL 34786
/25
$5,300 per month
- 4 Beds
- 3 Baths
- 2,984 Sq Ft
- House for Rent
5944 Caymus Loop, Windermere, FL 34786

Keenes Pointe, 24-hour gated/attended community built around The Golden Bear Club, an 18-hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, dining and swimming (membership required), and tucked adjacent to the Butler Chain of Lakes. This well-maintained property is ready for immediate occupancy. Features formal living and dining, private office, kitchen/family room,

Teresa Stewart SOUTHERN REALTY GROUP LLC

5944 Caymus Loop, Windermere, FL 34786
/2
$6,175,000 Sold Mar 28, 2025
- 8,203 Sq Ft
- $753/SF
- 204 Days On Market
- 5 Beds
- 7.5 Baths
- Built 2003
5518 Worsham Ct, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to this stunning estate, a masterpiece of design and functionality, where every detail has been meticulously crafted to create the perfect family retreat. Within the Isleworth Golf and Country Club community, this expansive property boasts over 8,000 square feet of luxurious living space, featuring a complete remodel with structural add-ons

Monica Lochmandy ISLEWORTH REALTY LLC

5518 Worsham Ct, Windermere, FL 34786

/34
Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,117 Sq Ft
6043 Savannah Oak Alley, Windermere, FL 34786

6043 Savannah Oak Alley, Windermere, FL 34786

/70
$4,200,000
- 5 Beds
- 5.5 Baths
- 7,561 Sq Ft
13125 Casabella Dr, Windermere, FL 34786

Welcome to Your Fully Automated Home in Casabella at WindermereIntroducing a spectacular 7,561 sq. ft. estate home perfectly positioned on a half-acre lot with tranquil pond views at both the front and rear. This 5-bedroom, 5.5-bath masterpiece offers total privacy, elegance, and cutting-edge technology. Fully integrated with Alexa and smart home controls, manage the entire property via iPad

Eduardo Pavone ON ME REALTY

13125 Casabella Dr, Windermere, FL 34786
/28
$2,900 per month
- 3 Beds
- 2.5 Baths
- 1,992 Sq Ft
- House for Rent
8371 Lookout Pointe Dr, Windermere, FL 34786

Energy efficient home in the Winderemere Trails. Property features solar panels. Granite counter tops, stainless steel appliances, decorative back splash, tile downstairs and carpet upstairs. The master bedroom features a walk in closet has an additional storage closet. All bedrooms are upstairs. Community pool and playground. Great schools zoned for this community. Conveniently located to Theme

Jessica Martinez Cestero HAMPTON & HAMPTON MGMT LEASING

8371 Lookout Pointe Dr, Windermere, FL 34786
/2
$3,750,000 Sold Mar 28, 2025
- 5,802 Sq Ft
- $646/SF
- 236 Days On Market
- 5 Beds
- 5.5 Baths
- Built 2002
5000 Down Point Ln, Windermere, FL 34786

Welcome to 5000 Down Point Lane in Windermere, a luxurious retreat situated on 2 acres of pristine lakefront property. This entirely renovated home offers breathtaking sunsets over Sunset Bay, providing a picturesque backdrop for daily living.The master suite, office, entertainment room and an additional suite are conveniently located on the main floor, while three more bedrooms and bonus

Dianna Desboyaux

5000 Down Point Ln, Windermere, FL 34786

/37
Est $466,644 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,760 Sq Ft
8368 Iron Mountain Trail, Windermere, FL 34786

8368 Iron Mountain Trail, Windermere, FL 34786

/72
$990,000
- 4 Beds
- 3.5 Baths
- 3,315 Sq Ft
8724 Peachtree Park Ct, Windermere, FL 34786

Windermere's Peachtree Park is a charming enclave of just 28 homes, uniquely situated directly across the street from Walt Disney World. The Key West-inspired architecture and meticulous craftsmanship of this home evoke feelings of comfort and elegance. The tranquil backyard paradise overlooks a serene pond and acres of uninhabited forest, providing a stunning backdrop for Florida sunrises.

Marcelo Machado VITORIA REALTY CORPORATION

8724 Peachtree Park Ct, Windermere, FL 34786
/36
$2,290 per month
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
- Condo for Rent
8276 Maritime Flag St Unit 207 (1214), Windermere, FL 34786

The BIGGEST floor plan in the Lakeview Community. Elegant and bright 3-bedroom, 2-bath condominium with an inviting open floor plan allowing abundant NATURAL LIGHT – an ideal setup for entertaining! ELEVATORS available for your convenience !!! The kitchen boasts a pantry, ample cabinets, and STAINLESS STEEL appliances GRANITE COUNTERTOPS. In-unit washer and dryer add convenience. The master suite

Maria Ubillus FOLIO REALTY LLC

8276 Maritime Flag St Unit 207 (1214), Windermere, FL 34786
/2
$355,000 Sold Mar 27, 2025
- 1,280 Sq Ft
- $277/SF
- 35 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2004
12557 Langstaff Dr, Windermere, FL 34786

Expect to be impressed with this charming townhome in the desirable Lake Reams Townhomes community. Immaculate and ready for you to move right in! Quality updates include: (1) Fresh interior paint in trendy neutral color (Jan., 2025), (2) New water heater (Jan., 2025), (3) Roof (home and detached garage) new in April, 2020, and (4) A/C only 3 years old. Layout features common living area on the

Stephanie Pitts KELLER WILLIAMS CLASSIC

12557 Langstaff Dr, Windermere, FL 34786

/50
Est $583,547 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,214 Sq Ft
7861 Berkshire Oak Alley, Windermere, FL 34786

7861 Berkshire Oak Alley, Windermere, FL 34786

/25
$795,000
- 4 Beds
- 4 Baths
- 3,239 Sq Ft
9227 Outlook Rock Trail, Windermere, FL 34786

Beautiful home in Windermere Trails, where luxury and convenience come together in the heart of one of Central Florida's most desirable communities. This stunning 4-bedroom, 4-bathroom home is ideally situated just a short stroll from Lakeside Village Center, offering easy access to Publix, charming local restaurants, and boutique shops. Perfectly zoned for top-rated Windermere schools, including

Steve Healy CORCORAN PREMIER REALTY

9227 Outlook Rock Trail, Windermere, FL 34786
/49
$6,450 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
$665,000 Sold Mar 27, 2025
- 2,967 Sq Ft
- $224/SF
- 47 Days On Market
- 5 Beds
- 3 Baths
- Built 2006
12706 Bideford Ave, Windermere, FL 34786

Reduced by 10K and New Roof prior to closing! This beautifully appointed 5-bedroom, 3-bathroom pool home offers the perfect combination of functionality and refined style. Upon entering, your eyes are immediately drawn to a breathtaking grand staircase that serves as the centerpiece of the entryway. Adjacent to the foyer is a formal dining area, ideal for hosting gatherings or enjoying intimate

Sangita Khatri BRIC REALTY LLC

12706 Bideford Ave, Windermere, FL 34786

/25
Est $394,829 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,505 Sq Ft
12852 Calderdale Ave, Windermere, FL 34786

12852 Calderdale Ave, Windermere, FL 34786

/49
$839,000
- 4 Beds
- 3.5 Baths
- 3,064 Sq Ft
12755 Westside Village Loop, Windermere, FL 34786

Come check this 4 bedroom 3.5 bath house with tile roof and the big porch at the front and the dining room and the living room combo great for indoor entertainment and has a spacious family room that’s open to an expansive kitchen , French door lead to the oversize the lanai , over look the community pool owner also upgrade all the light fixture give modern and contemporary feeling and office

Eric Jia NUMBER 1 BROKER, LLC

12755 Westside Village Loop, Windermere, FL 34786
/37
$4,200 per month
- 4 Beds
- 4 Baths
- 2,588 Sq Ft
- House for Rent
7282 Backwoods Trail, Windermere, FL 34786

Move into this AMAZING FULLY FURNISHED 4 bedroom, 4 full bath home located in Ashlin Park by Ashton Woods. 2 car garage, very nicebackyard, upstairs bonus room. *Guest Suite on the first floor.* Enjoy the amenities: community pool, club house, park area, tot-lot,conservation area, ponds, and bike trail access. Nearby parks include Walt Disney World, R.D. Keene Park, and Tibet-Butler

Maria Ubillus FOLIO REALTY LLC

7282 Backwoods Trail, Windermere, FL 34786
/2
$1,750,000 Sold Mar 27, 2025
- 5,110 Sq Ft
- $342/SF
- 233 Days On Market
- 6 Beds
- 4 Baths
- Built 2005
6215 Little Lake Sawyer Dr, Windermere, FL 34786

Looking for a move-in ready lakefront custom home in Windermere? Then look no further. This 6 bedroom, 4 full bath home with huge bonus room, pool and spa, sits on tranquil Little Lake Sawyer. With the lagoon style pool and enormous lot overlooking your own private dock, the backyard will become your own private oasis with panoramic views of the water morning, noon, and night. And speaking of

Shane Croft COLDWELL BANKER RESIDENTIAL RE

6215 Little Lake Sawyer Dr, Windermere, FL 34786

/37
Est $417,482 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,028 Sq Ft
8213 Mystic View Way Unit 2903, Windermere, FL 34786

8213 Mystic View Way Unit 2903, Windermere, FL 34786

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