Luxury Homes for Sale in
Windermere, Florida

Windermere is one of Central Florida’s most prestigious addresses, a lakefront town of gated estates and tree-lined brick streets minutes from Orlando and Walt Disney World. B | LIVE helps buyers and sellers navigate every Windermere community, from Isleworth to Keene’s Pointe.

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Luxury Windermere Properties

Explore featured homes across Windermere’s finest lakefront and gated communities, then let our team match you to the right property.

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Search homes for sale across Windermere, Isleworth, Keene’s Pointe, and the Butler Chain of Lakes.

Oscar Rodriguez
& Daniela Ledo

Oscar and Daniela’s mission is to serve Windermere buyers and sellers with the highest ethical standards. Expertise and integrity guide every step, from your first showing to closing day on your new home.

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Years Of Experience

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+23

Years Of Experience

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Residential Listings in Windermere

Set beneath a canopy of majestic live oaks along the shores of the Butler Chain of Lakes, this timeless estate has been comprehensively reimagined to blend enduring architecture with modern luxury. Rebuilt with uncompromising attention to detail, every major component of the home has been replaced, including the roof, windows & doors, HVAC systems, water heaters, pool equipment, dock, and landscaping. The home is also complete with a professionally curated furnishing package by Wassers. A refined palette of natural materials and exceptional craftsmanship defines every space, including custom Italian cabinetry, a premium SKS appliance suite, Taj Mahal quartzite countertops and full-height backsplashes, imported Portuguese limestone extending seamlessly from the interior to the pool terrace, and wide-plank light oak flooring throughout the upper level. Arched impact-rated windows and doors frame picturesque lake views while filling the home with natural light. Privately positioned to maximize the home's spectacular waterfront setting, the primary suite serves as a luxurious retreat featuring its own fireplace, a spacious sitting area, and a private balcony overlooking the lake. The spa-inspired bath rivals those found in the world's finest resorts, showcasing a dramatic wet room with a hand-carved marble soaking tub, handcrafted marble vanity, exquisite limestone, and an extraordinary custom Italian wardrobe system. Designed for effortless indoor-outdoor living, the private courtyard is inspired by timeless Mediterranean estates and framed by graceful arcades, tapered stone columns, restored architectural lanterns, and custom lighting. A freeform pool and elevated spa create a tranquil focal point, while the fully equipped summer kitchen, multiple covered terraces, and expansive entertaining spaces provide an exceptional setting for lakeside gatherings. Beyond the courtyard, beautifully landscaped grounds lead to a restored private dock and covered boathouse with direct access to the renowned Butler Chain of Lakes. No detail was overlooked, with additional highlights including a private elevator, custom wine room, designer lighting, thoughtfully restored architectural details, and curated finishes that create a timeless residence balancing warmth, elegance, and seamless indoor-outdoor living. Situated on renowned 2nd Avenue just moments from downtown Windermere, this remarkable residence establishes an entirely new benchmark for luxury renovation. Meticulously executed, flawlessly designed, and unlike anything else available today, this is more than a home it is a legacy property destined to become one of Central Florida's most iconic waterfront estates. $5,999,000 Active

800 W 2nd Avenue Windermere, Florida

5 Beds 5 Baths 5,511 SqFt 0.45 Acres

Welcome to an extraordinary lakefront estate on the prestigious shores of Lake Butler with 182 feet of water frontage, where timeless architecture, exceptional craftsmanship, and resort-style amenities come together in one of Windermere's most coveted locations. Built in 2024 and spanning approximately 6,900 square feet under air (10,400 total square feet), this custom residence sits on a rare one-acre homesite along the iconic, paved Second Avenue, renowned for its festive holiday displays, spectacular sunsets, and unmatched charm. Designed for both everyday luxury and grand scale entertaining, this 6 bedroom, 7.5 bathroom home offers en-suite bedrooms with walk-in closets, including a private first floor guest suite. The stunning primary retreat features a spa inspired bathroom and a private balcony overlooking the lake, creating the perfect setting to enjoy breathtaking sunsets and nightly Disney fireworks. The heart of the home is a designer chef's kitchen featuring exquisite Cristallo countertops, premium Miele appliances, and seamless flow into the expansive living and entertaining spaces. A dramatic floating wood staircase with a striking stone accent wall serves as an architectural centerpiece, while an elevator provides effortless access to every level. Additional highlights include a custom onyx sink in the powder bath, elegant 8-foot solid wood core doors throughout, motorized blinds, and laundry rooms on both the first and second floors. Step outside to experience a true private resort. The heated infinity edge saltwater pool features a unique acrylic glass viewing wall, allowing swimmers to enjoy underwater lake views unlike anything else. The expansive summer kitchen is equipped with two oversized Big Green Egg grills, a hibachi grill, and generous entertaining areas perfect for hosting unforgettable gatherings. A spacious game room with a full bar, dedicated fitness room, and professionally designed dog run complete the home's exceptional lifestyle offerings. Boating enthusiasts will appreciate the impressive two story private dock with multiple lifts, providing direct access to the famed Butler Chain of Lakes. Car collectors will love the oversized four car garage with an automotive lift, an additional golf cart garage, and an exceptionally long driveway offering abundant guest parking, a rare luxury on Second Avenue. Constructed with impact-rated windows and doors, spray foam insulation, and energy-efficient systems, this home was thoughtfully built to provide superior comfort, security, and efficiency. Combining impeccable design, world-class amenities, spectacular waterfront views, and one of the finest addresses in Central Florida, this remarkable Lake Butler estate represents a rare opportunity to own a nearly new custom home in one of Windermere's most sought after neighborhoods. Be sure to click on the virtual tour links. $7,500,000 Active

724 W 2nd Avenue Windermere, Florida

6 Beds 8 Baths 6,874 SqFt 1.1 Acres

Timeless Charm in the Heart of Downtown Windermere. Nestled beneath a canopy of majestic oak trees on one of Windermere’s most picturesque streets, this beautifully maintained three bedroom, two and half bath residence offers the perfect blend of classic Florida charm and modern comfort. Situated on a spacious 0.38 acre fenced homesite, this exceptional property features 2,795 square feet of living space and 4,163 total square feet, providing plenty of room to live, work, and entertain. From the moment you arrive, you will appreciate the peaceful setting and inviting curb appeal that make Oakdale Street one of the town’s most desirable locations. Inside, thoughtful craftsmanship is evident throughout with custom trim work, rich stone and wood flooring, double pane windows and doors, and a warm family room centered around a natural gas fireplace. The well appointed kitchen features a natural gas range, while the expansive air conditioned Florida room offers the perfect place to relax year round as you overlook the private backyard. Car enthusiasts, hobbyists, and those needing extra space will love the 4 car garage along with the detached air conditioned building, ideal as a home office, fitness studio, art studio, workshop, guest retreat, or whatever your heart desires. Recent improvements provide peace of mind, including: Roof replaced in 2019, newer HVAC system and water heater (4 years old) and a newer well pump (9 months old). Living in the Town of Windermere is more than owning a home, it’s embracing a lifestyle. Enjoy the beloved weekly farmers market, monthly food truck nights, festive holiday celebrations, and a charming downtown just a short walk away featuring a new Italian restaurant, breakfast café, coffee shop, wine bar, tennis courts, and more. Residents also enjoy exclusive access to community boat ramps on both Lake Butler and Lake Bessie, making it easy to experience the renowned Butler Chain of Lakes. If you have been searching for a home that offers character, generous space, exceptional flexibility, and one of Central Florida’s most treasured small town lifestyles, this is an opportunity you won’t want to miss. Be sure to click on the virtual tour links. $1,049,000 Active

725 Oakdale Street Windermere, Florida

3 Beds 3 Baths 2,795 SqFt 0.38 Acres

Welcome to a rare opportunity in the highly sought-after The Manors at Butler Bay, in the heart of Windermere. This custom-built home is situated on nearly three-quarters of an acre and a corner lot. This impressive single-story residence offers 3,478 square feet of thoughtfully designed living space with 4 bedrooms, 3 full bathrooms, a side-entry 2-car garage, an extended driveway, and a screen-enclosed pool and spa. Step through the front door into a grand foyer that opens to a spacious, flowing floor plan. The formal living room sits adjacent to the formal dining room, creating ideal space for entertaining. The expansive family room features soaring ceilings, a cozy wood-burning fireplace, and french doors that lead to the fully enclosed florida room. The oversized primary suite is a true retreat, featuring double-door entry, high ceilings, ample room for a sitting area, a walk-in closet, and french doors opening to the florida room. The spacious primary bath was remodeled approximately four years ago and offers dual vanities, a garden tub, separate shower, and a private toilet room. The open layout provides privacy and flexibility. Two secondary bedrooms share a full bathroom, while the fourth bedroom is tucked away on the opposite side of the home with its own ensuite bath, ideal for guests or multigenerational living. The kitchen is designed for both everyday living and entertaining with granite countertops, a center island with cooktop, built-in oven, dinette area, and more french doors leading to the florida room. The laundry room includes a utility sink and built-in cabinetry for added convenience. Wood-look tile flooring extends throughout the home, with carpet only in the enclosed florida room. One of the home's standout features is the expansive L-shaped florida room that wraps around the side and rear of the home, creating an abundance of bright, versatile space perfect for relaxing, entertaining, a home office, hobby room, fitness area, or additional living space, all while enjoying year-round comfort. Additional updates include an approximately 4-year-old HVAC system and 7-year-old roof, offering peace of mind for the next owner. The Manors at Butler Bay is an intimate community nestled along the shores of beautiful Lake Crescent in southwest Orange County. Residents enjoy a low HOA, golf cart friendly streets, a park with picnic area and access to Lake Crescent for launching non-motorized watercraft such as kayaks and canoes. As a resident of the Town of Windermere, you'll also enjoy access to town amenities including tennis courts and the Lake Butler boat ramp, providing entry to the renowned Butler Chain of Lakes (also known as the Windermere Chain), a 5,000-acre network of 13 interconnected lakes. Renowned for crystal-clear waters, prime bass fishing, luxury waterfront estates, and connects via 32 navigable canals for boating and water sports. The home is conveniently located within a top-rated school district and close to shopping, dining, and major roadways. This exceptional home offers the perfect combination of space, location, and lifestyle. Don't miss your opportunity to own this rare one-owner home in one of Windermere's most desirable communities! $1,100,000 Active

2512 Tryon Place Windermere, Florida

4 Beds 3 Baths 3,478 SqFt 0.73 Acres

Welcome to 20 Oakdale Street, an exceptional waterfront luxury residence in the highly sought-after Town of Windermere with direct access to Lake Down and the Butler Chain of Lakes offering an ideal blend of elegance, privacy, and Florida lifestyle, this beautiful home is perfectly positioned to enjoy the area's charming small-town atmosphere while remaining just minutes from world-class dining, shopping, golf, and attractions * Incredible backyard * Summer Kitchen with Pizza Oven * Firepit with Stone Seating * Boathouse * Viking 6 Burner Gas Cooktop * Viking Fridge * Built in 2004 * 2 Suites on 1st Floor * Step inside to discover spacious living areas filled with natural light, soaring ceilings, and thoughtfully designed spaces perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into inviting gathering spaces, while the generous bedrooms provide comfort and privacy for family and guests. * Outside, enjoy your own private retreat with beautifully landscaped grounds, ample outdoor living space, and the opportunity to experience everything that makes Windermere one of Central Florida's most desirable communities. Whether relaxing by the pool, hosting friends, or taking advantage of nearby lakes and recreation, this home offers the lifestyle you've been searching for. * Located within close proximity to top-rated schools, renowned golf courses, the Butler Chain of Lakes, and just a short drive to downtown Orlando and major theme parks, this is a rare opportunity to own a premier property in one of Florida's most coveted addresses. $1,499,000 Active

20 Oakdale Street Windermere, Florida

3 Beds 3 Baths 2,188 SqFt 0.42 Acres

OUTDOOR LIVING, ONE-STORY COMFORT & IN-TOWN WINDERMERE LIFESTYLE COME TOGETHER AT THIS RARE 1.27-ACRE WINDERMERE OAKS PROPERTY. Set within the TOWN OF WINDERMERE, this beautifully maintained one-story pool home offers privacy, space & the lifestyle buyers hope to find, with NATURAL GAS, mature landscaping, a PARTIAL BUTLER CHAIN LAKE VIEW, and exceptional outdoor living that feels like a true extension of the home.The screened pool area is the heart of the property, beautifully finished with brick pavers & designed for everyday enjoyment as well as memorable entertaining. The 35' X 20' IRREGULAR-SHAPED POOL is complemented by multiple water features, a separate step-in spa with bubbler, a custom firepit, and a highly functional summer kitchen with bar seating, grill, ice maker & refrigerator. With approximately 812 SQ FT OF OPEN FINISHED PORCH/LANAI AREA, including a main lanai approximately 62' X 12', there is room to dine, gather, relax, watch the game, host friends, or simply enjoy the peaceful setting in every season.The PRIMARY SUITE is a true highlight of the home, privately positioned and beautifully finished with a spacious bedroom, direct access to the outdoor living area, and a STUNNING PRIMARY BATH that feels calm, elegant & luxurious. Thoughtful details, generous closet space, quality finishes, and a retreat-like feel make this suite stand apart.Inside, the home offers a warm, livable floor plan with NO STAIRS & generous gathering spaces. The main living areas connect comfortably to the outdoor spaces, creating an easy flow for entertaining & everyday life. The kitchen is positioned at the center of the home with generous prep & storage space, natural gas cooking, and a connection to the main living & dining areas that keeps everyone together. Additional bedrooms & flexible rooms provide options for guests, work, hobbies, fitness, or multigenerational living. The ONE-STORY design offers long-term comfort & convenience without sacrificing space or privacy.The setting is what makes this property so special. With 1.27 ACRES inside the Town of Windermere, there is a sense of privacy & breathing room that is increasingly hard to find. Mature trees, established landscaping, and a long residential feel create a peaceful backdrop, while the partial lake view adds a lovely connection to the Butler Chain lifestyle without making the home solely about the view.Life in WINDERMERE OAKS means you are close to the charm of downtown Windermere, weekly farmers markets, community events, local parks, brick streets & the small-town character that makes this area so loved. You are also minutes from top schools, shopping, dining, major roadways & Central Florida attractions, making the location as practical as it is beautiful.This is the kind of Windermere property buyers hope to find but rarely do: 1.27 private acres, ONE-STORY LIVING, NATURAL GAS, exceptional outdoor living, a beautiful PRIMARY SUITE, a PARTIAL BUTLER CHAIN LAKE VIEW, and a setting that makes home feel like the best place to be. It invites you to slow down, gather often, celebrate outside & enjoy the lifestyle that makes the TOWN OF WINDERMERE so special. $1,295,000 Pending

516 Jennifer Lane Windermere, Florida

3 Beds 3 Baths 3,021 SqFt 1.27 Acres

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Your Trusted Experts in
Windermere Real Estate

At B | LIVE, we know Windermere. From the guard gates of Isleworth and Keene’s Pointe to the lakefront estates of Lake Butler Sound, more than 23 years of local experience lets us guide you through each community’s HOA, lake access, and resale dynamics with confidence.

Explore Windermere Neighborhoods

Isleworth

Guard-gated golf & lakefront

Keene's Pointe

Golden Bear golf community

Lake Butler Sound

Exclusive lakefront estates

The Reserve at Belmere

Gated family community

Windermere Club

New luxury construction

Downtown Windermere

Historic brick streets

Reasons to Choose Us

+23

Years Of Experience

$11M

Major Transaction

+805

Sold Properties

+$1B

Total Transactions

Best Marketing Strategy

Listing your home in the MLS is not enough.

We make sure your Home is highlighted with those UNIQUE features each home has to offer. We want to impress potential buyers. In order to do so, we have an amazing team “behind the scenes” specialized in the latest trends in marketing online, a fantastic photographer that will take the best pictures, 3D Tours, Zillow Tours and a PERSONALIZED video that will show your home perfectly, specially to those out of state buyers.

All this amazing material we produce is used in the right platforms online with the best demographic strategy depending on the market flow in the moment you decide to list your home.

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Featured Luxury Communities We Represent

Isleworth

Windermere, FL
Keene’s Pointe
Windermere, FL

Bella Collina

Montverde, FL

Bay Hill

Orlando / Dr. Phillips, FL

Lake Nona Golf Club

Orlando / Lake Nona, FL

Winter Park

Winter Park, FL

Golden Oak

Lake Buena Vista / Orlando, FL

Lake Butler Sound

Windermere, FL

Windermere

Windermere, FL

Kissimmee

Kissimmee, FL

Ocoee

Ocoee, FL

Winter Garden

Winter Garden, FL

@bliveluxuryhomes

What People Say About Us

+42 5-star Reviews

01 Testimonial

To say Daniela and Oscar are the BEST at what they do is an understatement! They are a dynamic duo!!!! They leave no stone unturned in helping guide you, stage for sale, from start to finish they will be at your side. They are the utmost professionals, know their market like no other(s), create fantastic videos and ..

Jose Cedeno

Windermere, FL

02 Testimonial

Oscar has been fantastic to work with. He has been diligent, responsive, proactive, honest and effective. He helped me rent my property over 8 years ago and when I told him I was ready to sell, he layed out a plan, we executed the plan, and the property was sold in less than 2 weeks. Full price

Dianne Russell

Orlando, FL

Windermere Real Estate FAQ

Windermere home prices range from around $500,000 for townhomes and non-waterfront homes to well over $10 million for lakefront estates in Isleworth and Lake Butler Sound. Gated golf communities such as Keene’s Pointe generally start around $1 million.

The most sought-after gated communities include Isleworth, Keene’s Pointe, Lake Butler Sound, and The Reserve at Belmere, each offering security, large lots, and access to golf or the Butler Chain of Lakes.

Yes. Windermere is known for top-rated schools, low-key luxury, a lakefront lifestyle, and a location minutes from Orlando, Walt Disney World, and Restaurant Row.

Many do. Windermere sits on the Butler Chain of Lakes, a chain of 13 connected lakes, and numerous homes include private docks and boat access.

Inventory is limited and desirable lakefront and gated-community homes can sell quickly, so an experienced local broker helps you act fast and negotiate well.

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Whether you are buying a lakefront estate, selling your Windermere home, or exploring gated communities, our team is here to guide you with a refined and personal experience.

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