Windermere, FL Homes

/95
$2,199,000
- 4 Beds
- 3.5 Baths
- 3,525 Sq Ft
505 Jennifer Ln, Windermere, FL 34786

Villa Casablanca | Luxury Windermere Estate on 1-Acre. Some homes are built. this was transformed. Set on a rare private acre within one of Windermere’s most privately held enclaves— this estate makes an immediate architectural statement. A circular motor court, tiered fountain, and mature canopy trees establish presence before you ever step inside.What unfolds within is architectural

Ahmad Hassan COMPASS FLORIDA LLC

505 Jennifer Ln, Windermere, FL 34786
/46
$3,275 Per Month
- 4 Beds
- 3.5 Baths
- 2,665 Sq Ft
- House for Rent
12706 Westside Village Loop, Windermere, FL 34786

Great House, Great Location! 4 beds and 3.5 baths just a few years old around the corner from the Lakeside Village Center in Windermere. This home is right across the street from the playground and pool center. With decorative pavers for the driveway, huge covered front porch. Choose to run across the street to take a dip in the gorgeous community pool, or sit on the front porch watching your

Bryce Rysewyk SPRING REALTY ONE LLC

12706 Westside Village Loop, Windermere, FL 34786
/2
$484,000 Sold Jun 16, 2025

12285 Joshua Tree Trail, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,149 Sq Ft
- Built 2015
Last Sold Summary
- 15% Below List Price
- $225/SF
- 161 Days On Market
Current Estimated Value $491,452

Last Listing Agent Erin Legler CHARLES RUTENBERG REALTY ORLANDO

12285 Joshua Tree Trail, Windermere, FL 34786

/33
Est $1,034,287 Not Listed For Sale

9127 Tintori Ln, Windermere, FL 34786
- 5 Beds
- 4 Baths
- 3,393 Sq Ft
- Built 2011
9127 Tintori Ln, Windermere, FL 34786

Last Sold Summary
- 5% Below List Price
- $321/SF
- 3 Days On Market
- Last Sold Price $1,090,000
- Mar 28, 2024
Last Listing Agent Yousef Zeidan RE/MAX

/66
$1,999,900
- 5 Beds
- 4.5 Baths
- 5,922 Sq Ft
5421 Tildens Grove Blvd, Windermere, FL 34786

Welcome to one of Windermere’s finest offerings — an impressive 5-bedroom, 4.5-bath estate spanning almost 6,000 sq ft on a premium 0.62-acre direct water-view lot in the exclusive 24-hour guard-gated community of Tildens Grove. This is a luxury build that combines sophistication with fun and accommodates an active lifestyle for family and entertaining: a custom private movie theater,

Mike Derenthal DERENTHAL REALTY

5421 Tildens Grove Blvd, Windermere, FL 34786
/15
$2,450 Per Month
- 3 Beds
- 2.5 Baths
- 1,406 Sq Ft
- Townhouse for Rent
8658 Brookvale Dr, Windermere, FL 34786

Beautiful townhome 3 BED, 2.5 BATH + 2 CAR GARAGE. Lake Reams is one of best kept secrets of the highly desired Windermere area of Orlando. Plenty of natural light, nice high ceilings. Block walls between units, all the way through the second floor. Park in your own two-car garage, and enjoy your own gorgeous private courtyard. This community has walking trails, surrounding reservation areas, and

Isabel Sirizzotti SUNNY 365 REALTY GROUP

8658 Brookvale Dr, Windermere, FL 34786
/2
$539,900 Sold Nov 20, 2025

11091 Bagley Aly, Windermere, FL 34786
- 4 Beds
- 2.5 Baths
- 2,222 Sq Ft
- Built 2018
Last Sold Summary
- 2% Below List Price
- $243/SF
- 123 Days On Market
Current Estimated Value $536,315

Last Listing Agent Mariana Cezar Ovalle WRA BUSINESS & REAL ESTATE

11091 Bagley Aly, Windermere, FL 34786

/34
Est $448,852 Not Listed For Sale

13829 Ingelnook Dr, Windermere, FL 34786
- 2 Beds
- 2.5 Baths
- 1,904 Sq Ft
- Built 2017
13829 Ingelnook Dr, Windermere, FL 34786

Last Sold Summary
- 3% Below List Price
- $244/SF
- 59 Days On Market
- Last Sold Price $465,000
- Sep 08, 2023
Last Listing Agent Kayla Korvenmaa ALIGN REAL ESTATE LLC

/81
$1,390,000 Pending
- 4 Beds
- 3.5 Baths
- 4,437 Sq Ft
13734 Lake Cawood Dr, Windermere, FL 34786

Under contract-accepting backup offers. NEW PRICE - SELLER MOTIVATED!Welcome to this stunning single-story luxury estate located in the highly sought-after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly a full acre at the end of a cul-de-sac, this beautifully maintained four-bedroom, three-and-a-half-bathroom home offers over 4,400 square feet of spacious,

Angela Schifano CHARLES RUTENBERG REALTY ORLANDO

13734 Lake Cawood Dr, Windermere, FL 34786
/23
$1,995 Per Month
- 2 Beds
- 2 Baths
- 1,161 Sq Ft
- Condo for Rent
8264 Maritime Flag St Unit 1419, Windermere, FL 34786

Beautiful Lakeside at Lakes of Windermere 2nd floor 2 bedroom condo with an open floor open, 42" cabinets, under cabinet lighting, breakfast bar and crown molding. Master bedroom has a large walk in closet and the master bath comes with a large vanity and walk in shower. All appliances including washer and dryer are included, along with water, sewer and valet trash. World class amenities include

Amanda Beckman RED DOOR INVESTMENT GRP LLC

8264 Maritime Flag St Unit 1419, Windermere, FL 34786
/2
$560,000 Sold Aug 13, 2025

6539 Chagford Ln, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,265 Sq Ft
- Built 2007
Last Sold Summary
- 2% Below List Price
- $247/SF
- 19 Days On Market
Current Estimated Value $555,316

Last Listing Agent Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

6539 Chagford Ln, Windermere, FL 34786

/2
Est $1,605,688 Not Listed For Sale

5856 Marleon Dr, Windermere, FL 34786
- 5 Beds
- 6.5 Baths
- 4,506 Sq Ft
- Built 2015
5856 Marleon Dr, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $347/SF
- 13 Days On Market
- Last Sold Price $1,563,888
- Jan 24, 2025
Last Listing Agent Xiaoyu Su RATIO REAL ESTATE, LLC

/20
$1,600,000
- 4 Beds
- 2 Baths
- 2,627 Sq Ft
212 W 1st Ave, Windermere, FL 34786

Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage and a dedicated boat dock, New boat house has been approved and permitted just waiting for you to build. The property captures sweeping views across Wauseon Bay. There is an option to build a new 3500

Eric Powell HOME WISE REALTY GROUP, INC.

212 W 1st Ave, Windermere, FL 34786
/32
$3,600 Per Month
- 3 Beds
- 2.5 Baths
- 3,212 Sq Ft
- House for Rent
5610 W Lake Butler Rd, Windermere, FL 34786

Exceptional opportunity to rent a lovely home in Windermere with easy access to Lake Butler Rd, top schools, and everyday conveniences. Enjoy comfort, privacy, and a welcoming neighborhood atmosphere.

Priscila Lima WRA BUSINESS & REAL ESTATE

5610 W Lake Butler Rd, Windermere, FL 34786
/2
$590,000 Sold Aug 06, 2025

5263 Beach River Rd, Windermere, FL 34786
- 4 Beds
- 3 Baths
- 2,432 Sq Ft
- Built 2004
Last Sold Summary
- 1% Below List Price
- $243/SF
- 26 Days On Market
Current Estimated Value $583,724

Last Listing Agent Ariel Vargas EXP REALTY LLC

5263 Beach River Rd, Windermere, FL 34786

/2
Est $1,861,381 Not Listed For Sale

5608 Marleon Dr, Windermere, FL 34786
- 5 Beds
- 5.5 Baths
- 5,228 Sq Ft
- Built 2015
5608 Marleon Dr, Windermere, FL 34786

Last Sold Summary
- 1% Above List Price
- $354/SF
- 128 Days On Market
- Last Sold Price $1,850,000
- Aug 27, 2024
Last Listing Agent Kyle Madorin UPWELL REALTY LLC

/57
$1,500,000
- 4 Beds
- 3.5 Baths
- 4,319 Sq Ft
5825 Oxford Moor Blvd, Windermere, FL 34786

Completely Remodeled 2022 | Single Story |Gated Windermere Community | Set on nearly three-quarters of an acre in the gated Oxford Moor community, this fully remodeled single-story home delivers the kind of space and finish level that's genuinely hard to find. Wide-open living areas, high ceilings, oversized rooms, and a modern aesthetic.The kitchen provides a large island, full stone

Jeffrey Funk EXP REALTY LLC

5825 Oxford Moor Blvd, Windermere, FL 34786
/12
$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
$975,000 Sold Oct 20, 2025

635 Butler St, Windermere, FL 34786
- 3 Beds
- 3 Baths
- 2,353 Sq Ft
- Built 1924
Last Sold Summary
- 2% Below List Price
- $414/SF
- 0 Days On Market
Current Estimated Value $982,950

Last Listing Agent Scott Arthur KELLER WILLIAMS REALTY AT THE LAKES

635 Butler St, Windermere, FL 34786

/2
Est $1,655,291 Not Listed For Sale

5566 Marleon Dr, Windermere, FL 34786
- 5 Beds
- 6 Baths
- 4,675 Sq Ft
- Built 2015
5566 Marleon Dr, Windermere, FL 34786

Last Sold Summary
- 3% Above List Price
- $342/SF
- 1 Day On Market
- Last Sold Price $1,600,000
- Aug 16, 2024
Last Listing Agent Paul Baker RE/MAX

/60
$1,250,000 Open Sat 1PM - 3PM
- 4 Beds
- 3 Baths
- 3,349 Sq Ft
2127 Lilypad Ln, Windermere, FL 34786

Welcome to a rare opportunity in the highly sought-after Willows at Lake Rhea, where incredible design, extensive upgrades, and an elevated Windermere lifestyle come together on a private 1⁄2-acre cul-de-sac lot in one of Central Florida’s most desirable luxury communities. This exceptional 4-bedroom, 3-bath residence features a thoughtfully designed split floor plan with two dedicated home

Angela Jaspon UNITED REAL ESTATE PREFERRED

2127 Lilypad Ln, Windermere, FL 34786
/12
$8,500 Per Month
- 4 Beds
- 3.5 Baths
- 3,062 Sq Ft
- House for Rent
8122 Whitford Ct, Windermere, FL 34786

GOLF FRONT!! Beautiful 4-Bed, 3-Bath Home for Rent in the Exclusive Keene’s Pointe Golf Community Nestled in the sought-after and secure gated community of Keene’s Pointe, this stunning single-story home offers a rare opportunity to live in a neighborhood renowned for its strong sense of community and premium amenities. Community Features: • Gated with 24/7 Manned Security: Peace of mind and

Hans Welbergen WINDERMERE INTERNATIONAL REALTY

8122 Whitford Ct, Windermere, FL 34786
/2
$635,000 Sold Sep 05, 2025

13978 Darchance Rd, Windermere, FL 34786
- 4 Beds
- 3.5 Baths
- 2,884 Sq Ft
- Built 2007
Last Sold Summary
- 4% Below List Price
- $220/SF
- 43 Days On Market
Current Estimated Value $635,929

Last Listing Agent Sean Popat BUYER REBATES REALTY

13978 Darchance Rd, Windermere, FL 34786

/22
Est $402,205 Not Listed For Sale

11637 Water Run Aly, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,466 Sq Ft
- Built 2017
11637 Water Run Aly, Windermere, FL 34786

Last Sold Summary
- 6% Below List Price
- $292/SF
- 4 Days On Market
- Last Sold Price $427,500
- May 14, 2024
Last Listing Agent Kris Ibrahim HOME WISE REALTY GROUP, INC.

/78
$1,900,000
- 4 Beds
- 4 Baths
- 3,196 Sq Ft
6110 Keenes Pointe Dr, Windermere, FL 34786

Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades.This 4-bedroom plus office, 4-bath home features a highly

Donna Calhoun KELLER WILLIAMS CLASSIC

6110 Keenes Pointe Dr, Windermere, FL 34786
/30
$2,650 Per Month
- 3 Beds
- 2.5 Baths
- 1,556 Sq Ft
- Townhouse for Rent
8913 Matriarca Aly, Windermere, FL 34786

Beautiful fully furnished townhouse located in the desirable Windermere area, just minutes from Walt Disney World and world-class resorts. This move-in ready home features a bright open-concept layout with a spacious kitchen, large island, and comfortable living spaces perfect for everyday living and entertaining. Conveniently located near top-rated schools, shopping centers, restaurants, grocery

Liz Henriques LA ROSA REALTY ORLANDO LLC

8913 Matriarca Aly, Windermere, FL 34786
/2
$710,000 Sold Feb 19, 2026

415 E 6th Ave, Windermere, FL 34786
- 3 Beds
- 2 Baths
- 1,784 Sq Ft
- Built 1986
Last Sold Summary
- 1% Above List Price
- $398/SF
- 8 Days On Market
Current Estimated Value $720,819

Last Listing Agent Omar Sousan LPT REALTY, LLC

415 E 6th Ave, Windermere, FL 34786

/36
Est $336,087 Not Listed For Sale

14335 Oasis Cove Blvd Unit 2004, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
- Built 2013
14335 Oasis Cove Blvd Unit 2004, Windermere, FL 34786

Last Sold Summary
- 8% Below List Price
- $241/SF
- 2 Days On Market
- Last Sold Price $363,800
- May 31, 2023
Last Listing Agent Lori Lucente-Nelson RE/MAX

/73
$1,475,000
- 6 Beds
- 4.5 Baths
- 4,027 Sq Ft
2635 Tryon Place, Windermere, FL 34786

Come tour the epitome of southern charm mixed with stately elegance located in the heart of Windermere- this beautiful colonial estate was masterfully crafted by Jim Akers and sits on an expansive 0.78 acre lot within the premier Manors at Butler Bay, offering shady oak trees within minutes of downtown Windermere and her chain of lakes. The home was custom built and showcases exceptional

Nipul Shah REIKI REALTY LLC

2635 Tryon Place, Windermere, FL 34786
/24
$2,800 Per Month
- 3 Beds
- 2.5 Baths
- 1,644 Sq Ft
- Townhouse for Rent
8470 Iron Mountain Trail, Windermere, FL 34786

Welcome to this pristine 3-bedroom, 2.5-bath townhome located in the highly sought-after Windermere Trails community in the heart of Windermere. Available starting May 1st. Requires one month security deposit. This two-story home features a spacious and functional layout, including a modern kitchen with 42" cabinets, granite countertops, stainless steel appliances, and a large island perfect for

Francis Acosta LPT REALTY, LLC

8470 Iron Mountain Trail, Windermere, FL 34786
/2
$385,000 Sold Jan 26, 2026

8625 Coventry Park Way, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 1,554 Sq Ft
- Built 2016
Last Sold Summary
- 6% Below List Price
- $248/SF
- 146 Days On Market
Last Listing Agent Alexandra Mateu BAHIA INTERNATIONAL REALTY

8625 Coventry Park Way, Windermere, FL 34786

/37
Est $525,509 Not Listed For Sale

11607 Black Rail St, Windermere, FL 34786
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
- Built 2012
11607 Black Rail St, Windermere, FL 34786

Last Sold Summary
- 2% Above List Price
- $242/SF
- 3 Days On Market
- Last Sold Price $517,000
- Jul 19, 2023
Last Listing Agent Camille Quidgley RE/MAX

/44
$1,599,000 Pending
- 5 Beds
- 5 Baths
- 3,520 Sq Ft
6001 Caymus Loop, Windermere, FL 34786

Under contract-accepting backup offers. Stunning Remodeled Golf Home in Keene’s Pointe – Windermere’s Premier Golf Community. Discover this unique, fully remodeled home in the highly sought-after Keene’s Pointe neighborhood, nestled in the picturesque lake community of Windermere. Offering privacy, breathtaking golf course views, and upgrades at every turn, this move-in-ready gem is the perfect

Stella Freeman QUATTRO R E SOLUTIONS LLC

6001 Caymus Loop, Windermere, FL 34786
/31
$2,399 Per Month
- 3 Beds
- 2.5 Baths
- 1,505 Sq Ft
- Property for Rent
7603 Bramwell St, Windermere, FL 34786

Reduce rental to live in Windermere, location, location Corner unit at Community of Windermere at Wickham Park . Step inside to find a bright and spacious great room that is perfect for entertaining. Gorgeous kitchen with 42” cabinets, granite counter tops up to backsplash. Private courtyard where you can relax in the sun. Second floor you will find the suite and 2 guest rooms. Very convenient as

Vivian Azuaje 1 ELEVEN REALTY

7603 Bramwell St, Windermere, FL 34786
/2
$1,069,499 Sold Nov 18, 2025

14365 Crest Palm Ave, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,628 Sq Ft
- Built 2025
Last Sold Summary
- 2% Above List Price
- $295/SF
- 0 Days On Market
Current Estimated Value $1,073,321

Last Listing Agent Nancy Pruitt OLYMPUS EXECUTIVE REALTY INC

14365 Crest Palm Ave, Windermere, FL 34786

/41
Est $309,792 Not Listed For Sale

Unlisted Address
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
- Built 2013
Unlisted Address

Last Sold Summary
- $205/SF
- 99 Days On Market
- Last Sold Price $310,000
- Mar 29, 2024
Last Listing Agent Vicente Virgilio ALTIS REALTY

/35
$430,000
- 3 Beds
- 2.5 Baths
- 1,589 Sq Ft
13366 Abuela Aly, Windermere, FL 34786

Welcome to this beautiful and move-in ready townhome located in the highly desirable Windermere area. Built in 2020, this modern residence offers the perfect combination of style, comfort, and low-maintenance living.This spacious home features 3 bedrooms, 2.5 bathrooms, and an open-concept layout ideal for both everyday living and entertaining. The kitchen showcases quartz countertops,

Alexandra Mateu BAHIA INTERNATIONAL REALTY

13366 Abuela Aly, Windermere, FL 34786
/60
$4,400 Per Month
- 4 Beds
- 2.5 Baths
- 2,236 Sq Ft
- House for Rent
11745 Via Lucerna Cir, Windermere, FL 34786

Experience luxury living in this beautifully updated 4-bedroom, 2.5-bathroom single-story home located in the 24/7 gated camera surveillance Belmere community in Windermere. This home has been completely and tastefully remodeled with luxury finishes throughout, transforming it into a modern sanctuary of comfort and elegance. Every detail has been upgraded with intention, blending sophistication,

Margaret Marambio LPT REALTY, LLC

11745 Via Lucerna Cir, Windermere, FL 34786
/2
$905,000 Sold Jun 16, 2025

6607 Crestmont Glen Ln, Windermere, FL 34786
- 5 Beds
- 3.5 Baths
- 3,199 Sq Ft
- Built 2002
Last Sold Summary
- 7% Below List Price
- $283/SF
- 126 Days On Market
Current Estimated Value $891,034

Last Listing Agent Joey Feeser WEICHERT REALTORS HALLMARK PR

6607 Crestmont Glen Ln, Windermere, FL 34786

/2
Est $9,169,143 Not Listed For Sale

9306 Blanche Cove Dr, Windermere, FL 34786
- 6 Beds
- 8 Baths
- 14,856 Sq Ft
- Built 2022
9306 Blanche Cove Dr, Windermere, FL 34786

Last Sold Summary
- 29% Below List Price
- $875/SF
- 132 Days On Market
- Last Sold Price $13,000,000
- Aug 12, 2024
Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

Showing Results 241 - 280, Page 7 of 18

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