Windermere, FL Homes for Sale

/38
$1,775,000
- 3 Beds
- 3 Baths
- 3,135 Sq Ft
12001 Lake Butler Blvd, Windermere, FL 34786

Exceptional Contemporary Estate in the Heart of Windermere! Discover the perfect blend of modern design, timeless comfort, and unmatched location with this beautifully updated estate home, ideally situated on a 1-acre lot in the desirable Town of Windermere. Surrounded by multi-million-dollar residences, and just moments from the famed Butler Chain of Lakes, this property offers a rare

Michael Julian JULIAN PROPERTIES, INC.

12001 Lake Butler Blvd, Windermere, FL 34786
/66
$3,699,000
- 3 Beds
- 5 Baths
- 4,262 Sq Ft
4812 Alexandra Garden Ct, Windermere, FL 34786

Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a

Rob Rahter STOCKWORTH REALTY GROUP

4812 Alexandra Garden Ct, Windermere, FL 34786
/30
$3,200,000
- 5 Beds
- 5 Baths
- 4,500 Sq Ft
13161 Lake Butler Blvd, Windermere, FL 34786

Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. Beautiful 5-bedroom, 3/2-bathroom Mediterranean-style home with inlaid marble medallion

Karolina Taylor EPIQUE REALTY, INC.

13161 Lake Butler Blvd, Windermere, FL 34786
/81
$5,000,000
- 6 Beds
- 9 Baths
- 8,305 Sq Ft
9721 Carillon Park Dr, Windermere, FL 34786

Welcome to 9721 Carillon Park Dr, Windermere, FL 34786, a stunning estate inside the guard-gated community of Keene’s Pointe.This extraordinary residence offers 8,305 square feet of luxury living space with refined architectural details, elegant wood beams, and designer finishes throughout. MAIN FEATURES: • Five bedrooms plus DETACHED GUEST HOUSE and OFFICE— providing exceptional space and

Dianna Desboyaux DOUGLAS ELLIMAN

9721 Carillon Park Dr, Windermere, FL 34786
/57
$3,400,000
- 4 Beds
- 4 Baths
- 4,877 Sq Ft
9731 Chestnut Ridge Dr, Windermere, FL 34786

Nestled within the gates of the renowned Isleworth Golf & Country Club, this beautiful four-bedroom estate offers nearly 5,000 square feet and showcases an elegant transitional style. The main level welcomes you with gracious formal living and dining rooms, each crowned with sparkling chandeliers and framed by oversized windows that capture elevated views of the resort-style pool and spa below.

Monica Lochmandy ISLEWORTH REALTY LLC

9731 Chestnut Ridge Dr, Windermere, FL 34786
/50
$670,000
- 4 Beds
- 3.5 Baths
- 2,297 Sq Ft
8582 Powder Ridge Trail, Windermere, FL 34786

AN IRRESISTIBLE INVESTMENT OPPORTUNITY — OR YOUR FIRST HOME!Welcome to this stunning Kipling model offering serene lake views and a host of exceptional upgrades. This home features fully paid-off solar panels, electric vehicle charging outlets, and a whole-house water filtration system for maximum efficiency and comfort. Step inside and enjoy the spacious loft above the garage, new carpeting,

Mariana Rondon LPT REALTY, LLC

8582 Powder Ridge Trail, Windermere, FL 34786
/81
$2,970,000
- 5 Beds
- 4 Baths
- 3,737 Sq Ft
10203 Trout Rd, Orlando, FL 32836

Discover this exquisite lakefront property nestled on over 1.9 acres with more than 100 feet of water frontage on LAKE TIBET and part of the Butler Chain of Lakes. This home offers breathtaking views and absolutely stunning sunsets. As you drive onto the winding paver circular driveway with lovely fountain and beautiful landscaping, you will notice the terracotta tile roof and the undeniable

Darlene O'Hara HOMEVEST REALTY

10203 Trout Rd, Orlando, FL 32836
/35
$599,990
- 3 Beds
- 2 Baths
- 2,077 Sq Ft
6315 Clearmeadow Ct, Windermere, FL 34786

***Freshly painted throughout and new carpet as 0f 3/23 for this move in ready home.*** New photos coming this week.This must-see home is ready to welcome you to the exclusive and upscale gatedsubdivision of Glenmuir. This spacious property is in an A-rated school district justminutes from Disney, Universal, Sea World, Downtown Windermere, and WinterGarden. Located on a quiet

Drew Wolski CORE REAL ESTATE GROUP

6315 Clearmeadow Ct, Windermere, FL 34786
/44
$3,200,000
- 4 Beds
- 4.5 Baths
- 3,745 Sq Ft
4819 Alexandra Garden Ct, Windermere, FL 34786

Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private

Michelle Corbin ISLEWORTH REALTY LLC

4819 Alexandra Garden Ct, Windermere, FL 34786
/45
$760,000
- 4 Beds
- 3.5 Baths
- 3,382 Sq Ft
11922 Angle Pond Ave, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to this beautifully maintained four-bedroom, three-and-a-half-bath home in the highly sought-after Windermere Trails community, located less than two minutes from Walt Disney World. The front of the home offers multiple flexible living spaces ideal for a home office, sitting room, or hobby area. The open family room flows into a spacious

Erica Diaz HOMEVEST REALTY

11922 Angle Pond Ave, Windermere, FL 34786
/45
$1,650,000
- 5 Beds
- 5.5 Baths
- 3,837 Sq Ft
1087 Jack Nicklaus Ct, Kissimmee, FL 34747

tunning, custom Bears Den property on an exceptional corner walled lot, backing onto a park for extra privacy, WITH ACTIVE REUNION MEMBERSHIP, & has 5 beds & 5.1 baths. This Bears Den property is absolutely breathtaking, offering an array of luxurious amenities and a meticulously designed living space. The impressive upgrades, including the high ceilings and engineered wood floors, create a sense

Penny Stokes Hilton TOP VILLAS REALTY LLC

1087 Jack Nicklaus Ct, Kissimmee, FL 34747
/91
$3,699,888
- 4 Beds
- 4.5 Baths
- 6,054 Sq Ft
12812 Jacob Grace Ct, Windermere, FL 34786

Experience Unmatched Lakeside Luxury in a Custom-Built MasterpieceDiscover the pinnacle of elegance and tranquility in this exquisite custom-built estate, ideally positioned on an expansive lot within an exclusive guard-gated community. With direct access to a crystal-clear spring-fed lake that permits private boat docks, this home offers a rare blend of relaxation, recreation, and refined

Alireza Partovi EXP REALTY LLC

12812 Jacob Grace Ct, Windermere, FL 34786
/19
$834,000
- 4 Beds
- 3.5 Baths
- 3,068 Sq Ft
6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786

New price reflects a fantastic opportunity for today’s buyers. Welcome to 6631 Crestmont Glen Lane, a stunning executive home nestled in the highly sought-after gated community of Glenmuir in Windermere, Florida. This beautifully maintained residence offers the perfect blend of comfort, elegance, and functionality on a spacious, landscaped lot.Featuring 4 bedrooms and 3 1/2 bathrooms, this home

Gonzalo Senior IRM INVEST., REAL EST.& MGMT.

6631 Crestmont Glen Ln Unit 1, Windermere, FL 34786
/62
$1,277,000
- 5 Beds
- 4.5 Baths
- 3,449 Sq Ft
11333 Camden Park Dr Unit 7, Windermere, FL 34786

One or more photo(s) has been virtually staged. Nestled within highly sought after guard gated community, this exceptionally maintained two-story residence combines timeless elegance offering the ideal blend of style, comfort, and functionality. The home features 5 spacious bedrooms, 4.5 bathrooms, dinning room, separate living room from family room and a generously sized loft—ideal for a

Cynthia Noto KARDOSH REALTY

11333 Camden Park Dr Unit 7, Windermere, FL 34786
/43
$769,000
- 5 Beds
- 3 Baths
- 3,357 Sq Ft
7409 Fairgrove Ave, Windermere, FL 34786

Enjoy resort-style living in the heart of Windermere! Located just minutes from major attractions, top-rated schools, and Downtown Orlando, this beautifully maintained 5-bedroom, 3-bath home offers the perfect blend of comfort, space, and community lifestyle. Neighborhood amenities include a resort-style pool, tennis and basketball courts, a playground and several green spaces for outdoor

Cristina De Jesus DALTON WADE INC

7409 Fairgrove Ave, Windermere, FL 34786
/26
$1,000,000
- Land
- 0.5 Acre
- $2,000,000 per Acre
2504 Windermere Reserve Ct, Windermere, FL 34786

Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of

Carolina Dumit CORCORAN PREMIER REALTY

2504 Windermere Reserve Ct, Windermere, FL 34786
/31
$1,630,000
- 3 Beds
- 2 Baths
- 2,238 Sq Ft
11923 Lake Butler Blvd, Windermere, FL 34786

Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large

Michael Julian JULIAN PROPERTIES, INC.

11923 Lake Butler Blvd, Windermere, FL 34786
/70
$6,699,000
- 5 Beds
- 5.5 Baths
- 6,257 Sq Ft
9259 Tibet Pointe Cir, Windermere, FL 34786

Welcome to 9259 Tibet Pointe Circle, an extraordinary lakefront residence nestled within the highly sought after guard-gated community of Keene’s Pointe. Completely renovated in 2025, this exquisite home combines timeless elegance with modern luxury, offering breathtaking views and direct frontage on the pristine waters of Lake Tibet. This meticulously updated estate showcases high-end finishes

Teresa Stewart SOUTHERN REALTY GROUP LLC

9259 Tibet Pointe Cir, Windermere, FL 34786
/100
$14,250,000
- 5 Beds
- 5.5 Baths
- 9,511 Sq Ft
5525 Isleworth Country Club Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. Exceptional in both style and scale, this extraordinary Isleworth estate represents the pinnacle of luxury living in one of the finest golf club communities in the world. Designed by architect Terry Irwin and built by Ballard Construction, with interior designs by Faith Fournet, the property has been fully transformed and thoughtfully curated over

Monica Lochmandy ISLEWORTH REALTY LLC

5525 Isleworth Country Club Dr, Windermere, FL 34786
/100
$2,675,000
- 6 Beds
- 4 Baths
- 4,482 Sq Ft
9648 Weatherstone Ct, Windermere, FL 34786

Welcome to this exceptional lakefront estate in the exclusive gated community of Weatherstone, ideally situated on the serene shores of Lake Olivia in Windermere, Florida. This beautifully appointed residence offers 6 bedrooms, 4 full bathrooms & a rare combination of timeless architecture & modern luxury. From the moment you arrive, the home's curb appeal is undeniable. The expansive wrap-around

Olga Jakubowski ERA GRIZZARD REAL ESTATE

9648 Weatherstone Ct, Windermere, FL 34786
/28
$2,500,000
- 4 Beds
- 4.5 Baths
- 4,961 Sq Ft
13377 Lake Butler Blvd, Winter Garden, FL 34787

Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

Dawn Briggs BLUE MAGNOLIA REALTY LLC

13377 Lake Butler Blvd, Winter Garden, FL 34787
/19
$2,500,000
- Land
- 5 Acres
- $500,000 per Acre
13377 Lake Butler Blvd, Winter Garden, FL 34787

Fantastic opportunity to purchase 12+ acres of private, quiet lake front property in Winter Garden/Windermere area on West Lake Butler Blvd. with 4+ acres high and dry and no HOA. Property currently boasts dock with electricity and boat lift on a skiable lake. There is an existing house that could be remodeled or torn down and start fresh. Home is 4961 square feet and built in 1990 with

Dawn Briggs BLUE MAGNOLIA REALTY LLC

13377 Lake Butler Blvd, Winter Garden, FL 34787
/38
$414,900
- 3 Beds
- 2.5 Baths
- 1,644 Sq Ft
12930 Vennetta Way, Windermere, FL 34786

Welcome to this beautifully renovated 3-bedroom, 2.5-bathroom townhouse in Berkshire Park, a highly desirable community in the heart of Windermere, Florida. With 1,644 sq ft of meticulously maintained living space, this move-in ready home is perfect for anyone seeking comfort, style, and convenience—just minutes from Walt Disney World, top-rated schools, and all that Central Florida has to offer.

Albert Viamontes, Jr FLORIDA IN MOTION REALTY INC

12930 Vennetta Way, Windermere, FL 34786
/97
$1,939,999
- 3 Beds
- 3.5 Baths
- 3,240 Sq Ft
13137 Lake Butler Blvd, Windermere, FL 34786

Kitchen refresh...Quartz countertops, seamless oversized sink. A kitchen designed to gather, host, and impress. Welcome to a private Windermere estate where thoughtful design meets relaxed luxury—set on over an acre with no restrictions. This beautifully updated 3-bedroom, 3.5-bath home offers space, privacy, and versatility, all surrounded by natural beauty. Enter through oversized double wood

Tricia Davis KELLER WILLIAMS REALTY SMART

13137 Lake Butler Blvd, Windermere, FL 34786
/71
$3,999,999
- 5 Beds
- 8 Baths
- 6,248 Sq Ft
11002 Lake Butler Blvd, Windermere, FL 34786

Price Adjustment! Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more than just a home: it’s a lifestyle destination, purposefully designed to inspire connection, relaxation, and

Sean Oakley SERENDIPITY REALTY LLC

11002 Lake Butler Blvd, Windermere, FL 34786
/62
$8,995,000
- 6 Beds
- 9 Baths
- 9,571 Sq Ft
6137 Grosvenor Shore Dr, Windermere, FL 34786

Experience luxury lakefront living on a grand scale in this custom-built Modern Mediterranean estate on Lake Tibet, part of the pristine Butler Chain of Lakes. The three-story residence spans 9,571 square feet of living space on over 2.2 acres in the guard-gated community of Keene’s Pointe in sought-after Windermere. Built by Goehring & Morgan, this architectural masterpiece offers refined

Mick Night PREMIER SOTHEBY'S INTL. REALTY

6137 Grosvenor Shore Dr, Windermere, FL 34786
/91
$18,500,000
- 7 Beds
- 8.5 Baths
- 10,649 Sq Ft
11900 Lake Butler Blvd, Windermere, FL 34786

Presenting Sunset Isle: an iconic waterfront estate compound capturing timeless elegance on Windermere’s largest and most prestigious Lake Butler, offering captivating unobstructed views from its 700 feet of lake frontage, a private island with moat and drawbridge, sandy beaches, two story double residence guest house, and a majestic and stunning grand mansion with additional guest retreat, all

Julie Bettosini STOCKWORTH REALTY GROUP

11900 Lake Butler Blvd, Windermere, FL 34786
/74
$3,590,000
- 8 Beds
- 7.5 Baths
- 8,203 Sq Ft
13643 Lake Cawood Dr, Windermere, FL 34786

Luxury HOME 8 Bedroom (all Suite) - with One acre lot in exclusive Lake Cawood Estates in Windermere. Built from ICF insulated concrete blocks for superior energy efficiency and hurricane protection with foam roof insulation, barrel tile roof and $25k whole house generator included. this home features the latest in technology and designer trends-whole house zoned audio system, multi point camera

Wenwen Wang JWJ REALTY LLC

13643 Lake Cawood Dr, Windermere, FL 34786
/62
$760,000
- 6 Beds
- 5.5 Baths
- 3,336 Sq Ft
11410 Rapallo Ln, Windermere, FL 34786

This stunning 6-bedroom Park Square home in Windermere combines elegance and functionality. The first floor features formal living and dining areas, a gourmet kitchen with stainless steel appliances and a gas stove, and a custom-designed patio garden with a water fountain and remote-controlled fans. Upstairs, enjoy luxury vinyl flooring, an oversized master suite with a walk-in closet, and

Rebeca Lima ORLANDO BROTHERS REAL ESTATE LLC

11410 Rapallo Ln, Windermere, FL 34786
/100
$7,950,000
- 7 Beds
- 10 Baths
- 8,362 Sq Ft
9343 Tibet Pointe Cir, Windermere, FL 34786

PRICE Improvenent!!Perfectly sited on pristine Lake Tibet in Keene's Pointe Country Club, this stunning lakefront Stonebridge custom home has been completelyupdated. The modern exterior color brightens the façade and creates a unique transitional style. The wrought iron and glass doors add a refined entry. Opening to the two-story formal areas featuring timeless elements of stone

Juan Delgado LA ROSA REALTY LLC

9343 Tibet Pointe Cir, Windermere, FL 34786
/31
$2,299,000
- 5 Beds
- 5.5 Baths
- 4,094 Sq Ft
11113 Lake Butler Blvd, Windermere, FL 34786

Welcome to this beautiful, unique and modern home. Recently built in 2023. Secluded in a great sized lot and within the sought-after and exclusive City of Windermere, known for its lush nature landscape trails, recreation parks, restaurants, cozy stores, beautiful lakes, great schools and much more!!! This luxury property also has a HOA 1/24th private deeded land with lake access, dock and ramp

Stella Freeman QUATTRO R E SOLUTIONS LLC

11113 Lake Butler Blvd, Windermere, FL 34786
/31
$1,475,000
- 4 Beds
- 4.5 Baths
- 4,257 Sq Ft
6443 Cartmel Ln, Windermere, FL 34786

Exquisitely appointed home being sold fully furnished. Nestled within the highly coveted Reserve at Lake Butler Sound community, this meticulously crafted residence epitomizes luxury living. Boasting classical architecture and spanning 4,257 square feet, this property offers a sophisticated retreat with unparalleled amenities. Upon entry, a raised travertine and marble foyer sets the tone for the

Julie Bettosini STOCKWORTH REALTY GROUP

6443 Cartmel Ln, Windermere, FL 34786
/2
$625,000
- Land
- 0.44 Acre
- $1,420,455 per Acre
2 Chase Rd, Windermere, FL 34786

Almost half an acre located on Main Street in the Town of Windermere

Matthew Hughes REAL BROKER, LLC

2 Chase Rd, Windermere, FL 34786
/2
$575,000
- Land
- 0.47 Acre
- $1,223,404 per Acre
9802 6th St, Windermere, FL 34786

Corner residential lot in Gotha. Small town charm near Windermere. No HOA. Shaded with Oaks. Easy access to 408 and Florida Turnpike. Great location, desirable schools and convenient to shopping, hospital, restaurants and more.

Judy Plett UPSIDE REAL ESTATE INC

9802 6th St, Windermere, FL 34786
$1,099,989 New Construction
- 4 Beds
- 3.5 Baths
- 3,728 Sq Ft
14348 Crest Palm Ave, Windermere, FL 34786

The Baldwin floor plan is a thoughtfully designed two-story home featuring 4 spacious bedrooms and 3.5 bathrooms, offering over 3,400 square feet of living space. The first floor boasts an inviting open-concept design, with a large great room adjacent to a dining room, perfect for gatherings and entertaining. The owner’s suite, complete with a walk-in closet and private bath, offers a comfortable

Dream Finders Homes Builder

14348 Crest Palm Ave, Windermere, FL 34786
/13
$5,500,000 New Construction
- 6 Beds
- 8 Baths
- 6,442 Sq Ft
1330 Lake Olivia Ln, Windermere, FL 34786

One or more photo(s) has been virtually staged. Pre-Construction. To be built. This is a lakefront estate currently under construction in Windermere, set on the shores of Lake Olivia with wide, unobstructed water views and rare privacy. This future residence will have 6 bedrooms, 6 full baths, and 2 half baths across 6,400+ sq ft, with 12’ ceilings on the main level, 10’ ceilings above, and

Ana Rubio EMPIRE NETWORK REALTY

1330 Lake Olivia Ln, Windermere, FL 34786
/40
$1,108,989 New Construction
- 4 Beds
- 4 Baths
- 3,123 Sq Ft
14347 Crest Palm Ave, Windermere, FL 34786

Step into refined living with this exceptional 4-bedroom, 4-bath residence spanning 3,123 square feet of impeccably designed space. Showcasing a sophisticated open-concept layout, this home offers the perfect balance of elegance and functionality. The main level impresses with soaring 10-foot ceilings and seamless laminate flooring, creating a bright, expansive ambiance. The gourmet kitchen is a

Dream Finders Homes Builder

14347 Crest Palm Ave, Windermere, FL 34786
/4
$6,700,000 New Construction
- 5 Beds
- 5 Baths
- 4,723 Sq Ft
11 Main St, Windermere, FL 34786

Under Construction. Brand New Construction in the Heart of Downtown Windermere – Currently Under Construction! Walking distance to downtown events, the farmers market, food trucks, and the local brewery. Historic Windermere is golf cart friendly and known for its outdoor lifestyle with parks, recreation areas, tennis courts, public docks, and swimming areas. Bring your boat! This waterfront

Milena Fernandes GOLDEN GROUP REALTY LLC

11 Main St, Windermere, FL 34786
/22
$2,500,000 New Construction
- 5 Beds
- 4 Baths
- 5,516 Sq Ft
6606 Sawyer Shores Ln, Horizon West, FL 34786

One or more photo(s) has been virtually staged. Pre-Construction. To be built. One or more photo(s) has been virtually staged. UNIQUE CANAL-FRONT PROPERTY ON LAKE SAWYER | BUILD-READY | NO HOA | WINDERMERE An extraordinary opportunity awaits on the shores of Lake Sawyer, tucked along a picturesque canal, this beautiful parcel delivers the perfect blend of privacy and possibility. With no HOA fees

Nick Khela PREMIUM PROPERTIES R.E. SERVICE

6606 Sawyer Shores Ln, Horizon West, FL 34786
/84
$13,995,000 New Construction
- 6 Beds
- 10 Baths
- 9,770 Sq Ft
9323 Gladys Garden Ct, Windermere, FL 34786

Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled rooflines, and a custom metal arched front door set a tone of understated elegance from the moment of arrival. Concrete tile roofing, four-car garage

Steve Healy CORCORAN PREMIER REALTY

9323 Gladys Garden Ct, Windermere, FL 34786

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