Windermere, FL Homes

/42
$1,333,000
- 5 Beds
- 4.5 Baths
- 3,190 Sq Ft
2828 Ingeborg Ct, Windermere, FL 34786

Welcome to this Mediterranean dream home tucked away at the end of a quiet cul-de-sac in Windermere, just steps from beautiful Lake Down. Sitting on over an acre of fenced land, this property is one of the most unique opportunities in the area. From the moment you arrive, the curb appeal stands out with a circular driveway that flows into a full side driveway leading to an oversized detached

Tiffany Pantozzi

ALIGN REAL ESTATE LLC

(689) 314-6947

2828 Ingeborg Ct, Windermere, FL 34786
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/117

$1,617 - $6,442 per month

Venetian Isle

1 - 3 Beds

6506 San Francesco Way, Windermere, FL 34786

A beautiful community with luxury one, two and three-bedroom apartment homes with a Mediterranean flair.We invite you to transport yourself to an upgraded level of luxury right at your front door. Every finish is hand-selected with the finest touch to make every day surpass the next. Our elegant, resort-inspired amenities have a level of sophistication youll find awe-inspiring day and night.

6506 San Francesco Way, Windermere, FL 34786
/2
$830,000 Sold Oct 30, 2025
- 3,151 Sq Ft
- $263/SF
- 136 Days On Market
- 5 Beds
- 4 Baths
- Built 2004
1638 Whitney Isles Dr, Windermere, FL 34786

Welcome to luxury living in the highly desirable gated community of Belmere, located in Windermere. This beautifully upgraded 5 bedroom, 4 bath pool home offers the perfect blend of elegance, comfort, and functionality. Featuring new luxury vinyl flooring, upgraded appliances, and an open concept split floor plan, the home is flooded with natural light that enhances its spacious and inviting

Morgan Horsley THE REAL ESTATE COLLECTION LLC

1638 Whitney Isles Dr, Windermere, FL 34786

/40
Est $734,854 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,988 Sq Ft
9150 Outlook Rock Trail, Windermere, FL 34786

9150 Outlook Rock Trail, Windermere, FL 34786

/32
$1,500,000
- 6 Beds
- 4.5 Baths
- 4,522 Sq Ft
17538 Black Rail St, Windermere, FL 34786

Spacious 6-bedroom, 4-bath Windermere home with dual master suites, pond views, and a fenced yard. Built in 2014, this residence features an open layout with a gourmet kitchen, granite counters, stainless steel appliances, and 42” cabinets. Upstairs includes a loft/media room and generously sized bedrooms. Enjoy serene water views, a private backyard, and a 3-car garage. Located in a desirable

Elaine Garcia

GARCIA REALTY GROUP

(689) 312-9273

17538 Black Rail St, Windermere, FL 34786
/27
$2,500 per month
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
- Townhouse for Rent
14284 Desert Haven St Unit 806, Windermere, FL 34786

VACANT! Great location! Great Home! Move in this Great home inside the lovely Oasis Cove community in the very desirable town of Windermere. This house is full of upgrades and is an Energy Star certified home. Downstairs has all tiled floor. It oversees the front porch. Kitchen has all fully appliances and granite counter top. You can also enjoy Disney firework at night. Upstairs has a large

Daniel Zheng CINO INTERNATIONAL INC

14284 Desert Haven St Unit 806, Windermere, FL 34786
/2
$789,000 Sold Oct 29, 2025
- 2,642 Sq Ft
- $299/SF
- 224 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2005
13413 Hopkinton Ct, Windermere, FL 34786

Newly Renovated Home near Disney!Stunning cul-de-sac Windermere residence, just minutes away from the enchanting world of Disney! 4 spacious bedrooms offering comfort and privacy for the whole family with 3.5 well-appointed bathrooms ensuring convenience and luxury. The 3-car garage providing ample space and storage options. with a host of state of the art features! Step into a space where

Jennifer Olmeda WRA BUSINESS & REAL ESTATE

13413 Hopkinton Ct, Windermere, FL 34786

/34
Est $518,463 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
13335 Overstreet Rd, Windermere, FL 34786

13335 Overstreet Rd, Windermere, FL 34786

/52
$414,999
- 3 Beds
- 2.5 Baths
- 1,461 Sq Ft
13808 Ancilla Blvd, Windermere, FL 34786

One or more photo(s) has been virtually staged. Back on the Market! Buyer’s financing fell through — their loss is your gain! During the transaction, the sellers installed a brand-new A/C unit, so the home is ready for its next owners to move in with comfort and peace of mind. Beautiful 3-bedroom, 2.5-bath townhome located in the desirable SUMMERPORT community of Windermere. Residents enjoy

Carlos German

EXP REALTY LLC

(407) 329-6677

13808 Ancilla Blvd, Windermere, FL 34786
/25

$1,676 - $2,603 per month

Casa Mirella

1 - 3 Beds

101 Casa Mirella Way, Windermere, FL 34786

Welcome to Casa Mirella Apartments, where lakeside living meets luxury in the heart of Windermere, FL. Enjoy sunny Florida days by the resort-style swimming pool, stay active in the fully equipped fitness center, or relax with friends at the picnic area with outdoor grills. Your furry friend will love the dog park at our luxury apartments in Windermere, FL, and you’ll appreciate the peace of mind

101 Casa Mirella Way, Windermere, FL 34786
/2
$595,000 Sold Oct 28, 2025
- 2,727 Sq Ft
- $218/SF
- 242 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2002
11313 Via Andiamo, Windermere, FL 34786

One or more photo(s) has been virtually staged. This beautiful Mediterranean-style home in a sought-after gated Windermere community is ready for you. Meticulously maintained, it features a kitchen with new stainless-steel appliances, 42" upgraded cabinets, and plenty of storage. The master suite boasts a large private balcony, while a second balcony is available in the guest bedroom. The home

Sean Popat BUYER REBATES REALTY

11313 Via Andiamo, Windermere, FL 34786

/30
Est $541,727 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
6442 Golden Dewdrop Trail, Windermere, FL 34786

6442 Golden Dewdrop Trail, Windermere, FL 34786

/62
$1,639,985
- 6 Beds
- 7 Baths
- 3,625 Sq Ft
11342 S Camden Commons Dr, Windermere, FL 34786

SELLER MOTIVATED. SOLD PARTIALLY FURNISHED. Situated at highly coveted community of Keenes Point in Windermere, this exquisitely home refined luxury living. FULLY REMODELED, Featuring six expansive bedrooms and five impeccably full bathrooms, and two half baths, every detail of this residence has been thoughtfully elevated.At the heart of the home lies a chef-inspired kitchen, appointed

Laura Teixeira

NOBSKA REAL ESTATE LLC

(407) 974-4620

11342 S Camden Commons Dr, Windermere, FL 34786
/15
$2,375 per month
- 3 Beds
- 2.5 Baths
- 1,644 Sq Ft
- Townhouse for Rent
8265 Maritime Flag St Unit 101, Windermere, FL 34786

Built in 2012, this spacious 3-bedroom, 2.5-bath townhouse offers the perfect blend of comfort, convenience, and community living. Step inside to find a bright and open floor plan featuring a large kitchen, dining area, and living room, perfect for entertaining or relaxing at home. All bedrooms are conveniently located on the second floor, providing added privacy. The home includes all major

Carissa Lawhun FLORIDA REALTY INVESTMENTS

8265 Maritime Flag St Unit 101, Windermere, FL 34786
/2
$830,000 Sold Oct 27, 2025
- 2,582 Sq Ft
- $321/SF
- 70 Days On Market
- 4 Beds
- 2 Baths
- Built 1986
616 Magnolia St, Windermere, FL 34786

Great Open Floorplan - 1 Story Ranch - Large Covered Rear Screened Porch - 4 bedrooms - 2 baths - Vaulted Ceilings - Large Fenced Lot - Located on the East side of Main Street and 1 House South of Conroy makes this home easy to get to - New Roof - Recently updated Kitchen - Tile Floors - Spacious Bedrooms - County Water - Natural Gas - Covered Parking in Backyard for Boat or RV - No HOA - Town of

Darrell Nunnelley VINTAGE REALTY GROUP LLC

616 Magnolia St, Windermere, FL 34786

/22
Est $1,050,346 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,117 Sq Ft
12525 Montalcino Cir, Windermere, FL 34786

12525 Montalcino Cir, Windermere, FL 34786

/51
$675,000 Open Sat 12PM - 3PM
- 3 Beds
- 2.5 Baths
- 3,094 Sq Ft
6734 Bridgewater Village Rd, Windermere, FL 34786

Luxury and privacy converge in Windermere’s sought-after Vineyards of Horizon West. This 3-bedroom, 2.5-bath home sits on an oversized conservation lot and combines modern design, natural tranquility, and top-rated schools - all under $1M in Windermere, Florida. From the moment you arrive, the paver driveway and fresh exterior paint (2024) set the tone for timeless curb appeal. Inside, you’ll

Alexis Bress

EXP REALTY LLC

(689) 345-8480

6734 Bridgewater Village Rd, Windermere, FL 34786
/35

$1,670 - $4,850 per month

MAA Crosswater

1 - 3 Beds

7826 Crosswater Trail, Windermere, FL 34786

TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Discover resort-style living at MAA Crosswater in Windermere, FL. Garden tubs, double vanity sinks, and washer/dryer units are featured in these one-, two-, and three-bedroom apartment homes. Admire the lake view from our sparkling swimming pool and cabana, or dig your toes in the sand \"beach\" lounging area.

7826 Crosswater Trail, Windermere, FL 34786
/2
$1,165,000 Sold Oct 27, 2025
- 4,565 Sq Ft
- $255/SF
- 0 Days On Market
- 6 Beds
- 4.5 Baths
- Built 2024
14404 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Under Construction. The Sweetwater Experience: Living in the Sweetwater means embracing a lifestyle where luxurymeets practicality. Start your day in the spa-like owner's suite, where dual walk-in closets eliminate the morning rush. Enjoy coffee on thecovered patio while the kids prepare for school in their own well-appointed spaces.

Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14404 Crest Palm Ave, Windermere, FL 34786

/40
Est $524,387 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,184 Sq Ft
12160 Canyon Sun Trail, Windermere, FL 34786

12160 Canyon Sun Trail, Windermere, FL 34786

/30
$1,575,000
- Land
- 2.12 Acres
- $742,925 per Acre
10948 Down Park Ln, Windermere, FL 34786

BUILD YOUR DREAM HOME in this incredibly rare vacant lot located in the highly sought after Town of Windermere! Zoned for single family residential and offering over 2.12 acres of land, this property is located on a lovely pond with 2 fountains and is in close proximity to the Butler Chain of Lakes offering the possibility for views of Lake Down which is situated incredibly close by! The private

Andrew Kincaid

BHHS FLORIDA REALTY

(689) 314-5758

10948 Down Park Ln, Windermere, FL 34786
/26
$2,200 per month
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Condo for Rent
8156 Boat Hook Loop Unit 303, Windermere, FL 34786

Third floor condo with three bedrooms, two full bathrooms at Lakeside at Lakes of Windermere. Private corner unit with elevator access in building. Tile in living area, and new laminate flooring in bedrooms, no carpet. Screened in balcony with sliding door access. Fully equipped kitchen with new kitchen appliances. Laundry closet with washer/dryer included. Entire interior was just repainted.

Rafael Pierluisi ALFANO PROPERTY MANAGEMENT

8156 Boat Hook Loop Unit 303, Windermere, FL 34786
/2
$1,000,000 Sold Oct 27, 2025
- Land
- 0.68 Acre
- $1,470,588 per Acre
- 211 Days On Market
5235 W Lake Butler Rd, Windermere, FL 34786

A rare opportunity to own over half an acre of direct lakefront property on prestigious Lake Butler. This prime vacant lot offers breathtaking views of Lake Butler and Bird Island. Design and build your custom dream estate in Windermere, one of Orlando’s most desirable communities. With direct access to the renowned Butler Chain of Lakes, enjoy unparalleled waterfront living—boating, fishing, and

Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

5235 W Lake Butler Rd, Windermere, FL 34786

/40
Est $630,635 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,208 Sq Ft
7230 Rambling Water Way, Windermere, FL 34786

7230 Rambling Water Way, Windermere, FL 34786

/12
$1,204,835 Pending
- 6 Beds
- 4.5 Baths
- 4,443 Sq Ft
14389 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Step into your next home at Palms at Windermere with the stunning Sweetwater floor plan. Offering over 4,400 square feet, this spacious two-story design features 6 bedrooms and 4.5 baths, blending luxury and function for today’s lifestyle. The first-floor owner’s suite is a private retreat with dual walk-in closets and a spa-inspired bath. A flex

Cindy Sapp

OLYMPUS EXECUTIVE REALTY INC

(689) 265-5806

14389 Crest Palm Ave, Windermere, FL 34786
/35

$1,708 - $4,563 per month

MAA Windermere

1 - 3 Beds

11598 Lachlan Ln, Windermere, FL 34786

TOUR YOUR WAY! We have a tour to fit your needs- virtual, self-guided, or agent-guided. Call MAA Windermere home in Windermere, FL. Our one-, two-, and three-bedroom apartment homes have all of the modern conveniences you're looking for. Select apartments feature spacious showers, double vanities, and soaking tubs. All units come with a washer/dryer and lots of natural light. Enjoy an expansive

11598 Lachlan Ln, Windermere, FL 34786
/2
$1,700,000 Sold Oct 27, 2025
- 3,255 Sq Ft
- $522/SF
- 211 Days On Market
- 3 Beds
- 3 Baths
- Built 1996
5243 W Lake Butler Rd, Windermere, FL 34786

One or more photo(s) has been virtually staged. Stunning Windermere Lakefront Retreat on the Butler Chain. Experience the epitome of lakefront living in this beautifully remodeled home, nestled on over half an acre with breathtaking views of Lake Butler and Bird Island. Whether you're boating, fishing, or simply relaxing by the pool, this retreat offers the perfect combination of luxury and

Andrew Burgard CHARLES RUTENBERG REALTY ORLANDO

5243 W Lake Butler Rd, Windermere, FL 34786

/49
Est $1,377,331 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,493 Sq Ft
1152 Estancia Woods Loop, Windermere, FL 34786

1152 Estancia Woods Loop, Windermere, FL 34786

/10
$1,048,337 Open Sat 1PM - 5PM
- 6 Beds
- 4.5 Baths
- 3,628 Sq Ft
7007 Windy Palm Way, Windermere, FL 34786

One or more photo(s) has been virtually staged. The Ellington II offers the perfect balance of space, comfort, and style. This modern two-story home features 5 bedrooms, 3 baths, and over 3,500 square feet of living space designed for today’s lifestyle. The open-concept main level includes a spacious kitchen, dining area, and great room ideal for entertaining. The private owner’s suite provides a

Cindy Sapp

OLYMPUS EXECUTIVE REALTY INC

(689) 407-6441

7007 Windy Palm Way, Windermere, FL 34786
/31
$2,200 per month
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Condo for Rent
11562 Amidship Ln Unit 208, Windermere, FL 34786

Freshly updated three bedroom, two full bathroom condo at Lakeside at Lakes of Windermere. Second floor unit with elevator access in building. Tile and new laminate flooring, no carpet. Screened in balcony with sliding door access. Fully equipped kitchen and laundry closet with washer/dryer. Community features, beach volleyball courts, pool, and fitness center. Two car assigned parking. Great

Rafael Pierluisi ALFANO PROPERTY MANAGEMENT

11562 Amidship Ln Unit 208, Windermere, FL 34786
/2
$1,290,000 Sold Oct 24, 2025
- 3,379 Sq Ft
- $382/SF
- 6 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2003
13527 Lake Cawood Dr, Windermere, FL 34786

You have a great opportunity to own this custom 5-bedroom home with a heated saltwater pool, private volleyball court, 3 car garage, on a 1-acre lot with lake views, in a gated Windermere neighborhood with one of the best public-school ratings from kindergarten to 12th grade. This home has an amazing curb appeal with its timeless Mediterranean architecture surrounded with lush, manicured

Simon Simaan THE SIMON SIMAAN GROUP

13527 Lake Cawood Dr, Windermere, FL 34786

/2
Est $727,453 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,424 Sq Ft
13302 Roskin Ln, Windermere, FL 34786

13302 Roskin Ln, Windermere, FL 34786

/2
$1,099,198 Open Sat 1PM - 5PM
- 4 Beds
- 3.5 Baths
- 3,404 Sq Ft
7019 Windy Palm Way, Windermere, FL 34786

One or more photo(s) has been virtually staged. Sample Image The Baldwin is a beautifully designed two-story home offering 4 bedrooms, 3.5 baths, and over 3,400 square feet of living space. The open-concept main level features a spacious great room and dining area that flow seamlessly into the kitchen—perfect for family gatherings or entertaining. The first-floor owner’s suite includes a private

Cindy Sapp

OLYMPUS EXECUTIVE REALTY INC

(689) 600-1926

7019 Windy Palm Way, Windermere, FL 34786
/20
$2,800 per month
- 3 Beds
- 2.5 Baths
- 1,818 Sq Ft
- WINDERMERE TRAILS - 3BR/2.5BA PLUS DEN - W...
8500 Iron Mountain Trail, Windermere, FL 34786

Check out this beautiful townhome, the primary bedroom is on the first floor, with an ensuite bathroom with dual sinks, and a large shower. The kitchen has 42" upper cabinets, double ovens, lots of storage, an eat in space, and an island. There is also a guest powder room. There is a nice private back patio/courtyard area, in between the home and 2 car garage. Upstairs is the laundry room

8500 Iron Mountain Trail, Windermere, FL 34786
/2
$1,099,995 Sold Oct 24, 2025
- 4,445 Sq Ft
- $247/SF
- 9 Days On Market
- 6 Beds
- 4.5 Baths
- Built 2001
9439 Westover Club Cir, Windermere, FL 34786

Welcome to Westover Club, a sought-after gated community in Windermere known for its tree-lined streets and excellent location. This well-maintained 6-bedroom, 4.5-bathroom pool home sits on a spacious 0.34-acre lot and offers a thoughtfully designed layout ideal for comfortable living and entertaining. Inside, you'll find an inviting open foyer, formal dining room, and dedicated office with

Sean Popat BUYER REBATES REALTY

9439 Westover Club Cir, Windermere, FL 34786

/67
Est $1,542,439 Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,007 Sq Ft
1220 Estancia Woods Loop, Windermere, FL 34786

1220 Estancia Woods Loop, Windermere, FL 34786

/3
$1,139,000 Open Sat 4PM - 7PM
- 6 Beds
- 4.5 Baths
- 4,443 Sq Ft
14225 Crest Palm Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Step into your next home at the Sweetwater in Palms at Windermere.With over 4,400 square feet, this expansive two-story floorplan offers six bedrooms and four and a half baths, blending luxury and function for today’s modern living.On the first floor, the owner’s suite is a private retreat with dual walk-in closets and a spa-inspired bath. A

Cindy Sapp

OLYMPUS EXECUTIVE REALTY INC

(407) 602-6772

14225 Crest Palm Ave, Windermere, FL 34786
/34
$2,850 per month
- 4 Beds
- 2.5 Baths
- 2,024 Sq Ft
- House for Rent
13892 Summerport Trail Loop, Windermere, FL 34786

... Move in ready... ... LAWN CARE, WASHER, and DRYER are included... ... This beautiful formal model home in Summerport and offers 4 bedroom/2.5 bath/2 car rear garage is loaded with a lot of upgrades... ... All bedrooms are located on the 2nd floor... ... Walking distance to Publix supermarket, Windermere High School, and local shopping... ...Community include the following amenities: fitness

Jennie Ho MAY HO REALTY

13892 Summerport Trail Loop, Windermere, FL 34786
/2
$392,000 Sold Oct 24, 2025
- 1,645 Sq Ft
- $238/SF
- 91 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2008
12975 Calderdale Ave, Windermere, FL 34786

Welcome to this beautifully maintained 3-bedroom, 2.5-bath end-unit townhouse nestled in the highly sought-after Wickham Park community in Windermere. Boasting an ideal layout and thoughtful features throughout, this home is perfect for comfortable everyday living and easy entertaining. Step inside to find tile flooring throughout the main level and plush carpeting upstairs. The spacious

Stephen Hachey FLAT FEE MLS REALTY

12975 Calderdale Ave, Windermere, FL 34786

/17
Est $713,971 Not Listed For Sale
1348 Lake Olivia Ln, Windermere, FL 34786

1348 Lake Olivia Ln, Windermere, FL 34786

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