Windermere, FL Homes

/54
$1,795,000 Pending
- 4 Beds
- 4.5 Baths
- 3,670 Sq Ft
830 Oakdale St, Windermere, FL 34786

Under contract-accepting backup offers. RARE FIND IN DOWNTOWN WINDERMERE!! This immaculate home defines where luxury meets contemporary, nestled in the heart of downtown Windermere. Pull up into your drive of Italian laced pavers and enter into your new home through custom French doors. You will be met by 2 story open floor plan where the oversized family room overlooks an outdoor oasis. A

Jay Martin

CORCORAN PREMIER REALTY

(407) 904-4148

830 Oakdale St, Windermere, FL 34786
/46
$13,000 per month
- 5 Beds
- 5.5 Baths
- 5,498 Sq Ft
- House for Rent
11051 Coniston Way, Windermere, FL 34786

Highly sought after custom home in Reserve at Lake Butler Sound. Beautiful iron arched double doors welcome you to an open floor plan with travertine floors and a view to the pool/lanai. Wrought iron chandeliers adorn the entry and spacious dining area. Upgraded features are aplenty in this beautiful home including top-of-the-line appliances, 2 gas fireplaces, and high ceilings. The large gourmet

Teresa Stewart SOUTHERN REALTY GROUP LLC

11051 Coniston Way, Windermere, FL 34786
/2
$765,000 Sold Sep 10, 2025
- 2,568 Sq Ft
- $298/SF
- 30 Days On Market
- 4 Beds
- 3 Baths
- Built 2001
9447 Westover Club Cir, Windermere, FL 34786

Welcome to this stunning Windermere pool home, located behind the iron gates of the desirable Westover Club community. This spacious 4-bedroom, 3-bathroom residence offers a thoughtfully designed 3-way split floor plan, perfect for both everyday living and entertaining. Private Backyard Paradise: Enjoy a serene outdoor space with an expanded paver patio, screen enclosure, a covered lanai and

Erica Sadelfeld THE REAL ESTATE COLLECTION LLC

9447 Westover Club Cir, Windermere, FL 34786

/34
Est $525,730 Not Listed For Sale
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
13335 Overstreet Rd, Windermere, FL 34786

13335 Overstreet Rd, Windermere, FL 34786

/2
$2,500,000 Pending
- 3 Beds
- 2 Baths
- 2,348 Sq Ft
10121 Lone Tree Ln, Orlando, FL 32836

A rare opportunity awaits with this exceptional triple-lot property on the renowned Butler Chain of Lakes—just minutes from the coveted Dr. Phillips area and with no HOA restrictions. Offering prime lakefront access, this oversized parcel is priced primarily for its land value and is the perfect canvas for creating your dream estate.The current residence is dated but move-in ready, giving

Ursula Garcia Moraes

PRISTINE INTERNATIONAL REALTY LLC

(321) 334-2943

10121 Lone Tree Ln, Orlando, FL 32836
/51

$1,776 - $2,795 per month

Arya at Windermere 55+ Active Adult Living

1 - 2 Beds

1231 Arya Way, Ocoee, FL 34761

Enjoy a vibrant lifestyle at Arya at Windermere, a 55+ community in Ocoee, FL offering unparalleled luxury amenities, including a massage room, steam room, outdoor putting green and a micro market. Arya features open concept 1 and 2-bedroom apartments with chef-inspired kitchens, granite countertops, stainless steel appliances, breakfast bar, wood-style plank floors, walk-in shower, washer and

1231 Arya Way, Ocoee, FL 34761
/2
$670,000 Sold Sep 09, 2025
- 2,084 Sq Ft
- $321/SF
- 7 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
9473 Palm Tree Dr, Windermere, FL 34786

Beautifully Renovated Pool Home in Silver Woods Now Available! This gorgeous home offers 3 Bedrooms, 2 Bathrooms, a Dedicated Office, and Open Floor Plan. Fully Remodeled and Meticulously Maintained. Amenities include: Quartz & Marble Counters, Stainless Steel Appliances (incl. 36" gas range), Solid Core Doors, Luxury Hardware & Lighting (Restoration Hardware/Pottery Barn), Slate & Woods

Mike Long COLDWELL BANKER RESIDENTIAL RE

9473 Palm Tree Dr, Windermere, FL 34786

/30
Est $540,728 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

/41
$435,000
- 3 Beds
- 2.5 Baths
- 1,461 Sq Ft
13808 Ancilla Blvd, Windermere, FL 34786

One or more photo(s) has been virtually staged. Beautiful 3-bedroom, 2.5-bath townhome located in the desirable SUMMERPORT community of Windermere. Residents enjoy fantastic amenities, including a CLUBHOUSE, a resort-style community swimming pool, tennis court, Volleyball court, basketball court, and a fitness center, multiple playground park and green spaces to enjoy beauty and nature, plus a

Carlos German

EXP REALTY LLC

(407) 329-6677

13808 Ancilla Blvd, Windermere, FL 34786
/18
$2,750 per month
- 3 Beds
- 2 Baths
- 1,926 Sq Ft
- House for Rent
6679 Duncaster St, Windermere, FL 34786

Discover this stunning 3-bedroom, 2-bathroom home with a spacious 2-car garage in the heart of Windermere! Step inside to find a move-in ready property designed for comfort and convenience. Zoned for top-rated schools, this home also offers the peace of mind of landscaping included in the rent—so you can enjoy a beautifully maintained yard without the work. Perfectly situated near shopping,

Tatiana Diaz FLORIDA LAKES REALTY

6679 Duncaster St, Windermere, FL 34786
/2
$625,000 Sold Sep 08, 2025
- 2,837 Sq Ft
- $220/SF
- 85 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2012
12867 Woodmere Close Dr, Windermere, FL 34786

Now Vacant & Drastically Reduced! Incredible opportunity in highly sought-after Lake Sawyer. This beautifully designed home is move-in ready and offers exceptional value for homeowners or investors. Set against serene pond and conservation views, the home boasts an elegant, open layout with formal living and dining areas, plus a first-floor oversized master retreat featuring a spa-like bathroom

nicoletta buonaccordo ALTIS REALTY

12867 Woodmere Close Dr, Windermere, FL 34786

/22
Est $1,036,619 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

/62
$1,649,985
- 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
/25

$1,691 - $2,578 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
$2,750,000 Sold Sep 08, 2025
- 3,316 Sq Ft
- $829/SF
- 169 Days On Market
- 4 Beds
- 4.5 Baths
- Built 1990
5524 Sail Ct, Orlando, FL 32819

One or more photo(s) has been virtually staged. LAKEFRONT GATED HOME, located in North Bay Neighborhood in Dr. Philips with access to Butler Chain of lakes. This remarkable home provides stunning marble and Travertine floors throughout, Gourmet kitchen, Gas Stove High-M Appliances, Splendid walking Wine Cellar with two Wood Burning Fireplaces and Stunning view in the Master Bathroom.

Miguel Osorio CENTURY 21 CARIOTI

5524 Sail Ct, Orlando, FL 32819

/40
Est $549,726 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

/56
$2,895,000
- 5 Beds
- 6.5 Baths
- 6,105 Sq Ft
11209 Macaw Ct, Windermere, FL 34786

A Masterpiece on the 4th Hole – Keene’s Pointe Luxury LivingPerfectly poised on a premium golf-front lot in the gorgeous, guard-gated community of Keene’s Pointe, this custom-built residence by Unnerstall blends refined craftsmanship with thoughtful design and breathtaking views of the Golden Bear Club’s 4th hole and tranquil water features.Boasting over 6,100 square feet of

Jay Martin

CORCORAN PREMIER REALTY

(407) 594-7145

11209 Macaw Ct, Windermere, FL 34786
/43
$6,500 per month
- 4 Beds
- 4 Baths
- 3,196 Sq Ft
- House for Rent
11357 Preserve View Dr, Windermere, FL 34786

Ideally situated on a corner lot within the prestigious, 24-hour guard-gated community of Keene’s Pointe in Windermere, this residence offers the perfect blend of elegance and comfort. Keene’s Pointe is renowned for its exceptional amenities, including fitness facilities, swimming, tennis, golf, and dining, all while being just minutes from Disney, shopping, and fine restaurants.The home

Janet Quinones MAGNUS REALTY GROUP LLC

11357 Preserve View Dr, Windermere, FL 34786
/2
$910,000 Sold Sep 05, 2025
- 2,608 Sq Ft
- $349/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 2002
1009 Algare Loop, Windermere, FL 34786

HIGHEST AND BEST BY 8-12-25 by 12 NOON Stop the car, this is the home you will fall in love with! Unique opportunity to purchase a beautifully RENOVATED POOL home with WATER VIEW in the desired, GATED Belmere community. Exceptional home, meticulously cared for! This MOVE-IN ready home will check most of your boxes! Spacious layout all on one floor. Great SPLIT FLOORPLAN for privacy, NEW CUSTOM

Petra Bukalo FLORIDA REALTY INVESTMENTS

1009 Algare Loop, Windermere, FL 34786

/40
Est $648,781 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

/38
$370,000 Open Fri 5PM - 7PM
- 4 Beds
- 2.5 Baths
- 2,067 Sq Ft
14234 Desert Haven St Unit 14234, Windermere, FL 34786

Spacious and well-appointed, this 4-bedroom, 2.5-bath townhome is the largest floor plan available in the community, offering over 2,000 square feet of comfortable living space. The layout includes a 2-car garage, screened-in patio, and a private fenced courtyard—perfect for relaxing outdoors or grilling with friends.Inside, the first floor features all tile flooring—durable, stylish, and

Debi Roldan

KELLER WILLIAMS ADVANTAGE III

(407) 975-5312

14234 Desert Haven St Unit 14234, Windermere, FL 34786
/35

$1,620 - $4,585 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
$440,000 Sold Sep 05, 2025
- 1,881 Sq Ft
- $234/SF
- 9 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2014
11420 Center Lake Dr, Windermere, FL 34786

Welcome to your dream townhome in the heart of Windermere!This beautifully maintained end-unit with gorgeous water frontage offers 3 spacious bedrooms plus a versatile den, 2.5 baths, and an inviting layout designed for both comfort and style. Located in the highly sought-after Lake Burden community, this home checks all the boxes for modern Florida living.Step inside to discover a

Millie Brockmeyer RE/MAX INNOVATION

11420 Center Lake Dr, Windermere, FL 34786

/49
Est $1,352,968 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

/51
$745,000
- 4 Beds
- 3.5 Baths
- 2,745 Sq Ft
13519 Bicton Ln, Windermere, FL 34786

Live Just Minutes from the Magic – Stunning 4-Bedroom Home in Gated Windermere Community. Welcome to 13519 Bicton Dr, a beautifully maintained 4-bedroom, 3.5-bathroom home offering nearly 3,000 square feet of thoughtfully designed living space with countless upgrades in one of Windermere's most sought-after gated communities. With a 3-car garage, a new roof, and new windows, this home combines

Tiphany Weeks DIAMOND REAL ESTATE GROUP

13519 Bicton Ln, Windermere, FL 34786
/17
$2,900 per month
- 4 Beds
- 2.5 Baths
- 1,997 Sq Ft
- Townhouse for Rent
7681 Fordson Ln, Windermere, FL 34786

Beautiful townhome for rent in the highly desirable community of Windermere Sound! This spacious property offers 4 bedrooms and 2.5 bathrooms, featuring ceramic tile flooring in the main areas and carpet in the bedrooms. The open floor plan is perfect for entertaining and includes a convenient second master bedroom with a private bath on the first floor, a modern kitchen with stainless steel

Reina Mendez REILE REALTY CORP

7681 Fordson Ln, Windermere, FL 34786
/2
$2,500,000 Sold Sep 05, 2025
- 4,667 Sq Ft
- $536/SF
- 0 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1977
2624 Midsummer Dr, Windermere, FL 34786

Beautiful lot on Midsummer Dr.

Jay Martin CORCORAN PREMIER REALTY

2624 Midsummer Dr, Windermere, FL 34786

/2
Est $757,734 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

/40
$589,900
- 4 Beds
- 2 Baths
- 1,798 Sq Ft
9319 Woodbreeze Blvd, Windermere, FL 34786

WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you

Steven Looper CHARLES RUTENBERG REALTY ORLANDO

9319 Woodbreeze Blvd, Windermere, FL 34786
/35

$1,688 - $4,062 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
$635,000 Sold Sep 05, 2025
- 2,884 Sq Ft
- $220/SF
- 43 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2007
13978 Darchance Rd, Windermere, FL 34786

Welcome to this beautiful 4-bedroom, 3.5-bathroom home with a 3-car garage, located in the highly desirable Enclave at Berkshire Park in Windermere. This spacious home offers a thoughtfully designed open floor plan with both a formal living room and a formal dining room, providing plenty of space for family gatherings and entertaining. The upgraded wood railing staircase makes a stunning first

Sean Popat BUYER REBATES REALTY

13978 Darchance Rd, Windermere, FL 34786

/67
Est $1,551,076 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

/90
$6,799,000
- 5 Beds
- 8 Baths
- 8,443 Sq Ft
11103 Bridge House Rd, Windermere, FL 34786

Step into timeless elegance, luxury, and sophisticated living. Located in the exclusive man-gated community of Lake Butler Sound—one of Central Florida’s most prestigious communities. From the moment you enter, you're greeted by high-end finishes, open-concept living space, and meticulous attention to detail. This stunning residence offers nearly 9,000 sqft of elevated living space featuring 5

Ayoub Aitelhaj THE SIMON SIMAAN GROUP

11103 Bridge House Rd, Windermere, FL 34786
/32
$2,800 per month
- 3 Beds
- 2.5 Baths
- 1,743 Sq Ft
- Townhouse for Rent
11267 Grander Dr, Windermere, FL 34786

READY TO MOVE-IN!!! Come see this beautiful modern townhome located in the subdivision of Lake Burden in Windermere FL. 3 BR 2 1/2 BA with den that could be used as an office space or guest bedroom. Light gray walls throughout, dark wood kitchen and bathroom cabinets, granite countertops in the kitchen and kitchen island. Very spacious kitchen island that fits 3 barstools comfortably. Open floor

Tiago Ferreira MANAGER PROP

11267 Grander Dr, Windermere, FL 34786
/2
$3,040,000 Sold Sep 05, 2025
- 5,874 Sq Ft
- $518/SF
- 65 Days On Market
- 6 Beds
- 5.5 Baths
- Built 1990
2937 Butler Bay Dr N, Windermere, FL 34786

**Video tour and 3D floorplan experience available.** Indulge in ultimate luxury at this gated Lake Crescent retreat. Enjoy water-skiing on a private lake, fishing from your private boat dock, and marveling at rocket launches, stunning sunsets, and pontoon plane landings—all from your own backyard. Embrace Florida living with a heated saltwater pool and spa waterfall surrounded by a spacious

Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

2937 Butler Bay Dr N, Windermere, FL 34786

/17
Est $706,164 Not Listed For Sale
1348 Lake Olivia Ln, Windermere, FL 34786

1348 Lake Olivia Ln, Windermere, FL 34786

/44
$1,089,000 Open Thu 5PM - 7PM
- 5 Beds
- 3.5 Baths
- 3,407 Sq Ft
12530 Climbing Vine Ct, Windermere, FL 34786

Welcome to this beautifully upgraded 5-bedroom, 3.5-bath home, just 11 minutes from Disney, where you can enjoy magical firework views from your second floor. Step inside to find a thoughtfully designed layout, featuring a front bedroom with an ensuite bath—perfect for guests or multigenerational living. The spacious kitchen is a chef’s dream, complete with a large island, double ovens, induction

Abby Nelson RE/MAX 200 REALTY

12530 Climbing Vine Ct, Windermere, FL 34786
/17
$2,350 per month
- 3 Beds
- 2 Baths
- 1,455 Sq Ft
- Condo for Rent
8192 Boat Hook Loop Unit 411, Windermere, FL 34786

This property at 8192 Boat Hook Loop features 3 bedrooms and 2 bathrooms within a total of 1,455 square feet. The living room offers ample space for relaxation and entertainment. The kitchen is equipped with a dishwasher and includes in-unit washer and dryer for convenience. The bathrooms provide essential amenities for daily use. The property is smoke-free and includes air conditioning for

8192 Boat Hook Loop Unit 411, Windermere, FL 34786
/50
$3,275,000 Sold Sep 05, 2025
- 8,047 Sq Ft
- $407/SF
- 67 Days On Market
- 6 Beds
- 8 Baths
- Built 2020
4065 Isabella Cir, Windermere, FL 34786

One or more photo(s) has been virtually staged. Step into elegance with this stunning, fully updated pool home, perfectly situated in one of Windermere’s most sought-after communities. Boasting sophisticated upgrades and timeless finishes throughout, this nearly new estate offers the ideal blend of modern luxury and comfort with a Control4 Smart System. Enjoy 5 massive bedrooms, 2 bonus rooms,

Tala Watkins Local Real Estate LLC

4065 Isabella Cir, Windermere, FL 34786

/30
Est $445,707 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,712 Sq Ft
11600 Water Run Alley, Windermere, FL 34786

11600 Water Run Alley, Windermere, FL 34786

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