Explore Windermere, FL Homes for Sale Between $1,750,000 to $2,000,000

Windermere, FL Homes for Sale Between $1,750,000 to $2,000,000 Map Search

Homes for Sale in Windermere, FL Between $1,750,000 to $2,000,000

Welcome to your dedicated resource for Homes for Sale Between $1,750,000 to $2,000,000 in Windermere, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Windermere, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $1,750,000 to $2,000,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Windermere, FL Homes for Sale Between $1,750,000 to $2,000,000

8229 Tibet Butler Drive, Windermere
$1,999,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style outdoor living and the coveted Windermere lifestyle come together beautifully. Perfectly positioned on 0.35 acres overlooking the 8th fairway of The Golden Bear Club’s Jack Nicklaus Signature golf course, this extensively updated 4-bedroom, 4-bath residence offers 3,912 square feet of living space designed for both elegant entertaining and comfortable everyday living. From the moment you enter, thoughtful upgrades and sophisticated finishes set the tone. Rich wood floors, designer lighting, custom window treatments and beautifully renovated living spaces flow into the heart of the home: a show-stopping gourmet kitchen featuring quartz countertops, an impressive 9-foot island, six-burner gas cooktop, wine refrigerator and stand-alone ice maker. Whether hosting a celebration or enjoying a quiet evening at home, this kitchen was made to gather around. The home's flexible floor plan is one of its greatest luxuries. Three bedrooms and three full baths are conveniently located on the first floor, including an expansive primary suite with a spa-inspired bath, oversized walk-in jetted shower and spectacular 12x14 ft. closet. A generously sized secondary primary bedroom features its own en-suite bath, while a dedicated home office with French doors provides a private and polished work-from-home environment. Upstairs becomes a retreat of its own, with a spacious bonus/gathering room, full bath and large bedroom accommodating two queen beds—an ideal arrangement for extended family, older children, visiting guests or a private second living area. Then step outside to your own Florida resort. The screen-enclosed Gunite pool has been completely resurfaced with new inset tile and is complemented by a new pool heater, pump and motor. A covered outdoor kitchen and bar invite year-round entertaining, the perfect setting for evenings under the stars—all framed by peaceful views across the golf course. And the improvements go far beyond what you can see. Recent investments include a new Carrier HVAC system with Wi-Fi-enabled Ecobee smart thermostats and UV systems, a refurbished whole-house Briggs & Stratton generator, enhanced landscape lighting, whole-house water purification, automated electric blinds in the primary suite, an EV charging outlet and overhead garage storage. Country Club living at its membership opportunities at The Golden Bear Club offer golf, tennis, fitness, swimming, dining, clubhouse amenities and an active social lifestyle. This is more than a beautifully renovated home. It is a thoughtfully designed sanctuary offering the space to gather, the privacy to retreat, and an extraordinary setting in which to enjoy the very best of Windermere living. Turnkey luxury. Golf-course views. Resort-style outdoor living. Welcome home to Keene’s Pointe.

8229 Tibet Butler Drive, Windermere

7467 Lake Albert Drive, Windermere
$1,870,000
6 Beds ⋅ 7 Baths ⋅ Lake Burden South Ph 2 SubDv. ⋅ 34786 Zip Code
Welcome to lakefront living in Windermere! Set along the shores of Lake Burden, this impressive 6-bedroom, 6.5-bath home offers more than 5,100 square feet of living space, a 3-car garage, and a flexible layout designed for both everyday living and entertaining. Featuring the builder’s major upgrades and owned by just one owner since purchased directly from the builder, this home has been exceptionally well maintained. Inside, soaring ceilings and generous living spaces create an immediate sense of openness, while expansive sliding doors bring the beautiful lake views right into the heart of the home. The spacious kitchen is ready for everything from quiet family dinners to a full house of guests. With two primary suites — one downstairs and one upstairs — plus an additional first-floor bedroom, the floor plan offers great flexibility for guests, multigenerational living, or a home office setup. Upstairs, oversized bedrooms, a large bonus room, and private balconies provide even more room to spread out and enjoy the views. The outdoor space is just as special, featuring an extended covered lanai, outdoor kitchen, mature landscaping, and a peaceful lakefront backdrop. Morning coffee by the water, weekend barbecues, sunset dinners — this home was made for Florida living. Located in Lake Burden South, in the heart of Windermere, this home offers a peaceful residential setting with convenient access to shopping, dining, entertainment, and everything the area has to offer. Big home, beautiful setting, fantastic layout — and a lake view that never gets old. Come see this one in person!

7467 Lake Albert Drive, Windermere

4282 Mckinnon Road, Windermere
$1,845,000
6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
A rare opportunity in Windermere for the buyer who values space, privacy and flexibility. Set on approximately 1.15 acres with no HOA, 4282 McKinnon Road offers nearly 5,900 square feet, six bedrooms, six baths, a pool and three-car garage — all in a highly sought-after Windermere location. The floor plan is exceptionally well suited for modern luxury living, with the primary suite, guest suite and private office all on the first floor, plus expansive additional living space upstairs. It works beautifully for multigenerational living, extended guests, work-from-home needs or simply for buyers who want room to spread out without sacrificing function. Recent improvements include new windows, newer HVAC systems, a 2018 roof, updated flooring, fresh paint and additional upgrades throughout — allowing the next owner to enjoy the scale and flexibility of an estate property without taking on a long list of immediate projects. What truly sets this property apart is the freedom it offers: over an acre, no HOA, substantial living space, a pool and room for future possibilities such as additional garage or guest space, subject to applicable zoning and approvals. Zoned for Windermere Elementary, Bridgewater Middle and Windermere High School, and also conveniently located near Windermere Preparatory School and Foundation Academy, the home is just minutes from downtown Windermere, approximately 20 minutes to Disney and offers easy access to the 429. 4282 McKinnon is compelling not simply because of its size, but because of how difficult this combination is to duplicate in Windermere. For the buyer looking for a more private, flexible and substantial way to live, this is one worth seeing.

4282 Mckinnon Road, Windermere

11051 Hawkshead Court, Windermere
$1,795,000
5 Beds ⋅ 6 Baths ⋅ Reserve At Lake Butler Sound SubDv. ⋅ 34786 Zip Code
Back on market due to buyer non-performance WITH PRICE ADJUSTMENT!! Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a seamless blend of sophistication and comfort. Spanning a thoughtfully designed single-story layout, the residence features five bedrooms, four full baths, and two half baths, all curated with impeccable attention to detail. From the moment you enter, soaring ceilings and an abundance of natural light highlight exquisite porcelain marble flooring that flows seamlessly throughout the main living areas—completely carpet-free for a clean, modern aesthetic. The bedrooms feature rich hardwood flooring, adding warmth and contrast. The open-concept design creates an inviting yet refined atmosphere, ideal for both intimate living and grand entertaining. At the heart of the home, the gourmet chef’s kitchen is a true showpiece, appointed with premium Viking stainless steel appliances, rich granite countertops, and bespoke custom cabinetry. Whether hosting elegant gatherings or enjoying everyday moments, this space is designed to impress. Step outside to your private resort-style sanctuary. The covered lanai, complete with a fully equipped outdoor kitchen and grill, overlooks a beautifully redesigned pool framed by lush, mature landscaping—creating a serene and secluded backdrop for relaxation or entertaining under the Florida sun. This home has been extensively upgraded with no detail overlooked, including a complete pool renovation with new equipment, a new screen enclosure, fresh exterior paint and lighting, two new HVAC systems, updated garage interiors and openers, EV charging capability, a new septic system, and a reverse osmosis water treatment system. Residents of this distinguished community enjoy 24-hour guard-gated security, private fishing dock on Lake Butler, and impeccably maintained surroundings—all just minutes from world-class attractions, fine dining, upscale shopping, top-rated schools, and major thoroughfares. This is more than a home—it is a statement of refined living in one of Central Florida’s most coveted addresses. Schedule your private tour today and experience it for yourself.

11051 Hawkshead Court, Windermere

6560 Lake Burden View Drive, Windermere
$1,799,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Experience refined, single-level living in this exceptional custom home located within Keene’s Pointe, Windermere’s premier guard-gated golf and lakefront community. Designed with both privacy and comfort in mind, this beautifully appointed residence offers 4 bedrooms, 4 full baths, a private office, and a resort-style pool and spa. At the front of the home, the dedicated office enjoys tranquil water views, creating an inspiring workspace. Inside, expansive windows frame the sparkling pool and spa, filling the living spaces with natural light and creating a seamless indoor-outdoor ambiance. Contemporary interior updates lend a true “jewel box” feel, with luxury finishes throughout. Neutral designer tones, upgraded Viking appliances, two newer A/C units, and custom iron Cantera double entry doors add both elegance and sophistication. The spacious three-car garage is discreetly tucked at the rear of the property, allowing the home’s striking front elevation and exceptional curb appeal to shine. Situated on an oversized one-third-acre lot overlooking the Camden River, the property offers generous green space and picturesque water views that enhance its impressive setting. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.

6560 Lake Burden View Drive, Windermere

713 Main Street, Windermere
$1,999,000
6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
SIGNIFICANT PRICE IMPROVEMENT! Come experience the character and charm of Historic Olde Windermere in a home that simply cannot be duplicated. Thoughtfully custom-built, this one-owner Transitional Craftsman residence blends timeless architecture with exceptional livability, just steps from downtown's quaint lifestyle, multiple parks, weekly farmers market, tennis courts, playgrounds, and resident-only access to the Butler Chain of Lakes. From the moment you arrive, handcrafted timber details, natural stone accents, and inviting front porch creates a sense of warmth rarely found in newer construction. Inside, soaring wood ceilings, exposed pecky cypress beams, custom built-ins, and a dramatic floor-to-ceiling stone fireplace make this house both elegant and welcoming. Designed for everyday living as much as entertaining, the chef's kitchen features premium JennAir appliances, a striking stone cooking alcove, ceiling-height cabinetry, expansive island, generous walk-in pantry, and seamless connection to the dining and family rooms. The flexible floor plan offers six bedrooms and six baths, including two private owner's suites on the main level, making the home ideal for multi-generational living, long-term guests or one of many private spaces. Upstairs, 4 spacious secondary bedrooms and a large over-garage flex room provide endless possibilities as a home fitness studio, media room, hobby space, or home office. Outdoor living is equally impressive with a large covered porch, a wood-burning fireplace, outdoor kitchen, cabana bath, Tiki hut, circular fire pit, designed for year-round enjoyment. The backyard offers ample room to design the custom pool, allowing the next owner to create a backyard tailored to their lifestyle rather than inheriting someone else's design. Additional highlights include a newer roof (2024), commercial grade fire suppression, an oversized three-car garage with exceptional storage and workspace, and the opportunity to add a front gate for enhanced privacy off Main St. Storm hardy with underground electrical utility lines and public water. This is a home has been meticulously maintained and for buyers who appreciate exceptional craftsmanship, enduring quality, and the unique lifestyle that only Historic Windermere offers. Take a short stroll to the Downtown Redevelopment Project and shop at Victoria Jewelers, Ace Hardware, Solvino Wine Bar and Fresco's, one of Dr. Phillips' favorite Italian restaurants, adding even more charm and convenience to this incredible location. Pool Possibility! The accompanying video has been digitally altered to illustrate what the property could look like with a pool added. The property currently does not include a pool; however, there is potential to add one....

713 Main Street, Windermere

12001 Lake Butler Boulevard, Windermere
$1,775,000
3 Beds ⋅ 3 Baths ⋅ Lake Butler Estates SubDv. ⋅ 34786 Zip Code
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 opportunity to enjoy luxury living in one of Central Florida’s most desirable communities. Step inside and be greeted by natural light pouring through every room, highlighting fresh interior paint (2025) and warm wood flooring. The open-concept floor plan creates an effortless flow between living, dining, and entertaining spaces, anchored by a cozy wood-burning fireplace. Offering incredible flexibility, the home features two primary suites—perfect for multi-generational living or guest accommodations—along with a dedicated flex room to adapt to your lifestyle. Designed for both relaxation and recreation, the home’s outdoor living spaces are a true highlight. A screen-enclosed pool and spa, expansive covered lanai, and lush surroundings create the perfect backdrop for year-round Florida living. For those with a passion for travel or hobbies, the oversized 48x20 recreational garage provides exceptional space for a motor coach, RV, or boat. With a brand-new roof (2025), freshly painted exterior (2025), and durable block construction, this home is move-in ready while still offering room for expansion. Located within the coveted A-rated school district, close to charming downtown Windermere, world-class golf, and renowned shopping and dining, this residence offers not just a home, but a lifestyle. Owner finance options available. Don’t miss your chance to own a piece of Windermere luxury — where contemporary elegance, everyday comfort, and premier location meet.

12001 Lake Butler Boulevard, Windermere

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