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$4,995,000
6 Beds ⋅ 7 Baths ⋅ Sunset Bay SubDv. ⋅ 34786 Zip Code
Nestled behind the gates in the heart of Windermere, this exceptional lakefront estate commands sweeping views across the renowned Butler Chain of Lakes. Designed for refined living and effortless entertaining, the residence offers six bedrooms, six full baths, and a powder bath — including a fully equipped private guest apartment ideal for extended family or long-term visitors. From the moment you arrive, the home’s striking architectural presence is undeniable. A dramatic entry with soaring ceilings and intricate iron detailing introduces expansive living spaces crafted with both grandeur and comfort in mind. Walls of glass and retractable doors blur the line between indoors and out, inviting natural light and panoramic lake vistas into nearly every room. The main level showcases elegant formal spaces, a richly appointed study, and a music room, along with a stunning lakefront family room and game room complete with a stylish wet bar. At the heart of the home, the gourmet kitchen features premium finishes, abundant workspace, and seamless flow for hosting gatherings large or intimate. The primary suite and an additional guest suite are thoughtfully positioned on the first floor for privacy and convenience. Upstairs, guests are treated to elevated lake views from a spacious lounge with kitchenette, multiple bedroom suites, a private theater with adjoining sitting area, and a spectacular balcony overlooking the water. Outdoor living is simply extraordinary. A heated saltwater pool and spa anchor the expansive terrace, complemented by a summer kitchen, bar seating, and a fireplace — the perfect setting for sunset evenings on the water. A private boathouse offers direct access for boating, paddleboarding, or fishing along one of Central Florida’s most coveted waterways. Despite its serene setting, the home is just minutes from upscale shopping, dining, and world-class attractions, including Walt Disney World, and approximately 20 minutes to Orlando International Airport. With the owners preparing for their next chapter, this extraordinary waterfront retreat presents a rare opportunity to own on the Butler Chain at a compelling value. A lifestyle of privacy, beauty, and convenience awaits.

5070 Down Point Lane, Windermere
$1,396,000
6 Beds ⋅ 5 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
Stunning Two-Story Pool Home in Prime Windermere Location Welcome to this exceptional two-story residence located in the highly desirable Windermere area, offering the perfect blend of luxury, space, and comfort. With 6 generously sized bedrooms and an open, airy design, this home is ideal for families seeking both elegance and functionality. The primary suite is a true retreat, featuring a spacious layout and a walk-in closet, while the remaining bedrooms are equipped with built-in closets for added convenience and organization. The home offers 4 full bathrooms and 1 half bathroom, thoughtfully designed to accommodate both residents and guests with ease. As you enter, you are welcomed by an open floor plan enhanced by high ceilings that create a bright and expansive atmosphere throughout. The living room and dining room are impressively spacious, perfect for entertaining or enjoying everyday living in style. The beautifully designed kitchen features solid wood cabinets, stone countertops, and included appliances, combining timeless finishes with modern practicality. Step outside to your private outdoor oasis, where a fully equipped outdoor kitchen overlooks a large and stunning in-ground private pool. This space is ideal for hosting gatherings, relaxing, and enjoying Florida living year-round. The home also includes a 2-car attached garage and is located in a prime area with easy access to major roads and top-rated schools. This is a rare opportunity to own a remarkable home in one of Windermere’s most sought-after locations. Schedule your private showing today and experience everything this exceptional property has to offer.

13596 Gorgona Isle Drive, Windermere
$7,250,000
5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
A masterfully reimagined golf-front estate, this residence offers an unparalleled standard of luxury within the acclaimed guard-gated community of Isleworth. Completely reimagined and expanded, the residence offers over 7,000 square feet of refined living space, including a 2,400+ square-foot second-story addition designed by acclaimed architect Mark Nasrallah. Situated on over half an acre, the two-story home features 5 bedrooms, 6.5 bathrooms, and a seamless blend of timeless modern design and resort-style living. A striking 10-foot custom pivot door welcomes you into light-filled interiors, where elegant European porcelain tile and expansive open living spaces create a bright, elevated ambiance. Designed for both entertaining and everyday living, the main living areas flow effortlessly through expansive sliding glass doors to a stunning outdoor retreat, complete with a fully retractable screen enclosure. The chef’s kitchen serves as the centerpiece of the home, appointed with top-of-the-line appliances, custom European cabinetry, designer countertops, and an oversized island. A hidden chef’s pantry and temperature-controlled wine cellar enhance both functionality and style. The main-level primary suite offers a private, resort-inspired retreat, featuring a custom walk-in closet, a versatile bonus room ideal for fitness or wellness, and a dedicated in-home spa room. The spa-like primary bath includes a soaking tub, expansive walk-in shower, and a tropical outdoor shower, creating a tranquil escape. Upstairs, the newly constructed addition includes a secondary primary suite with a luxurious bath and walk-in closet, additional en-suite bedrooms, a spacious game room with access to a grand balcony overlooking panoramic golf course views, and a refined home theater. Outdoor living is equally impressive, featuring a sleek pool and heated spa, outdoor kitchen, wet bar, surround sound, and lush, manicured landscaping designed for privacy and enjoyment. Additional highlights include a fully integrated Crestron smart home system controlling lighting, audio, climate, and security, as well as a brand-new Generac generator for uninterrupted comfort. Fully remodeled and upgraded throughout, this residence presents a rare opportunity to own a like-new luxury estate in one of Central Florida’s most prominent communities.

5074 Isleworth Country Club Drive, Windermere
$560,000
4 Beds ⋅ 3 Baths ⋅ Windermere Trls Ph 3b SubDv. ⋅ 34786 Zip Code
Beautiful 4-Bedroom Home in Windermere, FL – Prime Location and Comfort for the Whole Family! Discover this amazing home located in one of Florida’s most desirable neighborhoods – Windermere! Featuring 4 spacious bedrooms, 2 full bathrooms and a half bath, this property offers the ideal space and layout for families seeking comfort and quality of life. The home is vacant and move-in ready, perfect for those looking to relocate quickly and easily! Located in a gated community with excellent recreational amenities, you'll enjoy access to a pool, playground, sports courts, and more – all in a warm, family-friendly environment. Close to major supermarkets, local shops, hospitals, and shopping centers Easy access to main roads and highways Situated in an area with A-rated schools, ideal for families who value top-quality education If you're looking for a complete home in a highly sought-after area with everything nearby, this is the perfect opportunity. Schedule your visit today and come see this charming home in Windermere for yourself

8225 Bryce Canyon Avenue, Windermere
$2,099,000
6 Beds ⋅ 6 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
Seller is offering up to $40,000 toward Buyer’s allowable closing costs, prepaids, and/or rate buy-down with acceptable offer. 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.... 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.

713 Main Street, Windermere
$779,900
5 Beds ⋅ 3 Baths ⋅ Summerport Ph 05 SubDv. ⋅ 34786 Zip Code
This beautiful MOVE-IN-READY two-story home is located in the highly desired community of Summerport in Windermere! The Wow factor begins the moment the front door opens to a towering cathedral ceiling making for a dramatic and elegant entry into the main living area. The open floor plan creates a seamless flow throughout the home, whereby the family room opens to the kitchen and dinette space, with brand New beautiful Gray Travertine throughout all countertops, that provides the perfect entertaining opportunity! A freshly painted neutral color palette, additional recessed lighting added downstairs, and luxury vinyl flooring in all the entertaining areas are just some of the exceptional design elements. Natural gas range and stainless-steel appliances, coffee/wine station, and a huge center island with breakfast bar creates a gourmet kitchen. Large windows and sliding glass doors allow for an abundance of natural lighting and beautiful views overlooking a screen enclosed Lanai with a gazebo to enjoy relaxing evenings. Upstairs are four of the five bedrooms and two full baths, completely Renovated with Galaxy stones From. floor to ceiling, and other bathroom renovated also with High technology toilet flushing by itself ; the fifth guest bedroom is located on the first floor with direct access to the third full bathroom. All Flooring New and recently changed upstairs. The Primary Suite boasts an enormous walk-in closet, and en-suite with double bowl vanity, private water closet, a large soaking tub and separate shower stall. The upstairs Theater with 4 cinema chairs is a great place for movies and popcorn with an oversized 9' projection screen! 2 New Air Conditioners-1 replaced in 2021, 2nd unit replaced in June 2022. Brand New Roof Sept /2023 (Lifetime warranty) Summerport residents enjoy the beautiful community Clubhouse with an oversized swimming pool, tennis/pickleball and basketball courts, workout room, and walking/jogging paths. Located in TOP RATED school zones, this fabulous home is close to all major shopping and boutiques, fine dining as well as Disney attractions with easy access to Downtown Orlando and the Orlando International airport.

4415 Blue Major Drive, Windermere
$4,750,000
7 Beds ⋅ 8 Baths ⋅ Gotha Town SubDv. ⋅ 34786 Zip Code
Discover “Bella Olivia”: a grand mediterranean estate perched high above Lake Olivia showcasing sweeping lake views, private gates, and an expansive luxury residence spanning over 8,900 square feet of living space across 7 bedrooms, including two primary suites, two guest apartments, garage space for 6 cars, an enormous screened enclosure with resort-style pool and spa, over 5.4 acres and no HOA. This private palace with brand new roof impresses with large circular paver drive, 3-tiered fountain, 10-foot iron front doors, 35-foot high ceilings, custom iron railings, and marble and travertine flooring – plus, coffered ceilings and elegant details throughout. Home has been extensively updated and lovingly cared for to highlight classic style and luxury to compliment today’s sophisticated lifestyle. The main kitchen features beautiful marble counters, three islands, two preparation sinks, custom cabinetry, and stainless appliances including two dishwashers, two microwaves, double ovens, and a Viking gas stove. The first-floor primary retreat is dressed with hardwood flooring, tray ceiling, and triple crown molding, and an exceptional bathroom with tiled shower, jetted tub, dual vanities, and expansive double closets. The main living spaces are abundant and stately with two first-floor family rooms, billiards room, living room, dining room, theater, and guest suite – upstairs is a third family room, secondary master suite, and three additional guest suites, plus a large balcony with screens. A separate entrance off the kitchen provides access to a private guest apartment with a kitchenette, family room, and bedroom. Plus, a second private apartment (978 sq feet, not included in the listed 8,931 sq feet) is accessible from the outside and is located over the 4-car garage and features family room, sink, and bedroom. Functional outdoor living space is extended to the mammoth screened enclosure to encompass a sitting area off the master and an additional family room with fireplace, tv, and full summer kitchen across the pool deck that can be separated by an electric additional privacy screen. The showstopping infinity edge pool is colossal in size and includes a sun shelf for shallow water relaxing and an infinity hot tub. Both sides of the house have all been paved with a new drainage system and ramps for easy access for boats and watercraft to Lake Olivia. The 150 ft refreshed covered dock has two cradles: currently set for a boat and two jet skis. There’s also a sitting area for lounging lakeside. Experience the best of Windermere with this lakefront retreat built for privacy, luxury, and lifestyle.

9575 Westover Roberts Road, Windermere
$680,000
5 Beds ⋅ 4 Baths ⋅ Lakes Windermere Ph 01 49 108 SubDv. ⋅ 34786 Zip Code
With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual pantries that actually hold it all. The primary suite sits privately on the main floor with with a large walk in closet, and ensuite, while three additional bedrooms offer room to spread out — perfect for guests, a home office, or both. The main-level guest bath keeps accessibility in mind with a sleek zero-entry shower, while a nearby half bath makes life easier for everyday traffic. Upstairs, a full suite with its own bath creates the ideal spot for visitors, multi-generational living, or a tucked-away retreat when you need a breather. Covered porches in both the front and back extend your living outdoors, while a rear-entry two-car garage keeps the curb appeal clean. Inside the garage, a wheelchair ramp provides easy access from the garage — and can be removed by the seller if not needed. Major updates are already handled: newer roof (2021), water heater (2018), and one of two HVACs replaced in 2021. Low HOA dues get you high-return perks — a resort-style pool, lake pier for fishing and star-gazing, tennis, volleyball, basketball, playgrounds, and open green space for everything else. All of it just minutes from Windermere’s shops, dining, and top-rated schools. High ceilings, natural light, updates for modern comfort — this is the Windermere vibe, done right.

6712 Thornhill Circle, Windermere
$809,500
4 Beds ⋅ 4 Baths ⋅ Peachtree Park SubDv. ⋅ 34786 Zip Code
Recent price adjustment creates a compelling opportunity in Peachtree Park, a boutique Windermere community of just 28 homes located across from Walt Disney World. This Ashton Woods Bimini model offers 4 bedrooms, 3.5 baths, a private office, formal dining room, upstairs loft, and thoughtfully designed living spaces throughout. Highlights include wood flooring on the first level, a gourmet kitchen with quartz countertops, butler’s pantry with wine cooler, custom breakfast-nook seating, and a spacious primary suite with a custom walk-in closet. Outdoor living is a standout feature, with more than 1,000 sq. ft. of decking under screen enclosure, overlooking a peaceful pond and wooded backdrop. A rare combination of privacy, space, upgrades, and location in one of Windermere’s most distinctive communities. Schedule your private showing today.

8724 Peachtree Park Court, Windermere
$4,778,000
6 Beds ⋅ 9 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
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 privacy. • Expansive master suite with private sitting room, balcony overlooking the pond, dual closets, fireplace, and breakfast area. • Chef’s kitchen with a large island, seating area, top-of-the-line appliances, and a hidden walk-in pantry. • Bar and game room featuring real wood finishes and picturesque pond views. • Private GYM with SAUNA for health and relaxation. • Nine-seat HOME THEATER with plush carpet flooring for an immersive movie experience. • Four-car split garage (2/2), ELEVATOR, and downstairs laundry room. * Additional laundry closet inside the upstairs primary bedroom closet. OUTDOOR & LIFESTYLE: Seamlessly blending indoor and outdoor living, the open floor plan connects to a heated pool and spa area, surrounded by tranquil pond views and lush landscaping. The fully retractable sliding doors make it ideal for entertaining year-round. RECENT UPGRADES INCLUDE: • Five new AC units (2023) • Hurricane-impact windows and ADT smart security system • New pool equipment (2022) • Exterior repaint (2023) • Full surround-sound system throughout the home COMMUNITY & LOCATION: Located within the prestigious Keene’s Pointe community, residents can enjoy The Golden Bear Club, featuring a Jack Nicklaus Signature golf course, clubhouse, fitness center, and dining. Windermere is renowned for its lakes, top-rated schools, and luxury lifestyle just minutes from downtown Orlando and Disney attractions. This home represents the pinnacle of luxury living in Windermere, offering elegance, privacy, and resort-style amenities. Schedule your private tour today and experience the sophistication of this remarkable estate.

9721 Carillon Park Drive, Windermere
$1,630,000
3 Beds ⋅ 2 Baths ⋅ Lake Butler Estates SubDv. ⋅ 34786 Zip Code
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 center island and ample space to prepare gourmet meals. Enjoy the Florida lifestyle year-round from the screened-in lanai overlooking the serene, tree-lined backyard. Additional highlights include a side-entry 2-car garage and a detached private workshop or storage building with electricity—perfect for hobbies, home projects, or extra storage. As a resident of the Town of Windermere, you'll enjoy exclusive access to two private boat ramps on the Butler Chain of Lakes, six lighted tennis courts, multiple parks and playgrounds, frisbee golf, and scenic lakefront beaches. The town also hosts vibrant community events including weekly farmers markets, monthly food truck nights, and seasonal festivals. Zoned for top-rated schools and just minutes from world-class golf, premier shopping and dining, hospitals, and Central Florida’s renowned theme parks, this home offers the best of both serenity and convenience. Schedule your private showing today and discover the charm and lifestyle that only Windermere can offer!

11923 Lake Butler Boulevard, Windermere
$745,000
6 Beds ⋅ 6 Baths ⋅ Belmere Village G2 48 65 SubDv. ⋅ 34786 Zip Code
This stunning 6-bedroom Park Square home in Windermere combines elegance and functionality is NOW VACANT. 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 spacious additional bedrooms. Located in the gated Belmere Village, residents benefit from low HOA fees and exceptional amenities, including a clubhouse, fitness center, resort-style pool, playground, basketball, volleyball courts and newly added pickleball courts. Conveniently near major highways and Orlando's theme parks, this home offers the perfect blend of luxury and location. Don't miss this opportunity—schedule a showing today!

11410 Rapallo Lane, Windermere