Homes for Sale Near Olympia High in Windermere - 63 homes

Remarks: Welcome to Isleworth Golf & Country Club. This home features a grand entrance that welcomes you with a spacious open foyer featuring a custom bar and a dramatic two-story living room with a fireplace, creating an impressive yet inviting setting for entertaining. Providing access from all rooms to the outdoor living area, the thoughtfully designed floor plan blends elegance and functionality throughout. The kitchen is designed for both everyday living and entertaining, featuring Thermador appliances, including a cooktop, double ovens, warming drawer, microwave, dishwasher, icemaker, and beverage refrigerator. The space overlooks a generous dinette area with direct access to the patio, seamlessly connecting indoor and outdoor living. A formal dining room and a spacious great room provide additional gathering spaces for family and guests. The primary suite, located on the first floor, is a private retreat complete with three closets and a spa-inspired bath showcasing a large walk-in shower, soaking tub, and dual vanities. A second ensuite bedroom is also conveniently located on the main level, along with a well-appointed laundry room featuring built-in cabinetry. Upstairs, the travertine staircase with iron railing leads the way to a large game room with wet bar and French doors opening to an expansive balcony overlooking the pool and golf course. Two additional ensuite bedrooms complete the upper level. Throughout the home, you’ll find plantation shutters, travertine flooring, and hardwood floors, adding warmth and sophistication. The property also features an oversized three-car garage with storage and a large driveway for ample parking.Outdoor living is truly exceptional, with a large swimming pool, covered patio with half bath, and summer kitchen with beverage refrigerator—perfect for entertaining while enjoying serene golf course views. The oversized fenced backyard offers privacy and space to relax or play. Conveniently located to shopping, dining and expressways, as well as top-rated public and private schools, this home has it all!

Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)

Listing Agent: Teresa Stewart (407-493-3057)

Remarks: Majestic and stately, this castle inspired residence sits on a 1.2 acre homesite within the privately gated enclave of Lake Down Crest. Its commanding presence is defined by patterned stone and brickwork, gabled rooflines, slate accents, wooden beams, and a shimmering grand fountain that sets an unforgettable first impression. Double front doors open to an impressive foyer flanked by formal living and dining rooms, while a step down home theater or richly paneled den—with custom built ins—creates a dramatic focal point. The well appointed kitchen features an island with prep sink, stainless appliances, gas cooktop, pantry, and a bright breakfast nook, making it ideal for both entertaining and everyday living. The inviting family room showcases a fireplace, custom millwork, and wood flooring, with French doors that lead to a Travertine patio overlooking the pool, elevated spa with waterfall, iron fencing, and paver decking. The primary retreat is a sanctuary of its own, complete with a private entrance foyer, bedroom with ceiling niche, fireplace, alcove, separate den or nursery, and a luxurious bath featuring a double headed pass through shower, jetted tub, marble topped vanities, and a spacious walk in closet. A secondary guest suite is also conveniently located on the main level. Upstairs, three additional bedrooms accompany a massive bonus room over the garage—perfect as a game room, theater, sixth bedroom, or private guest wing. A rare Florida feature, the finished basement offers exceptional flexibility for a game room, office, or substantial storage. A four and a half car drive through garage provides entrances on both sides and abundant storage. The home is nestled within an exclusive 32 residence community in East Windermere, offering top tier schools and effortless access to SR 408, downtown Orlando, I 4, Mall at Millenia, Walt Disney World, Universal Orlando, and Central Florida’s premier attractions.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)

Remarks: Nestled on a rare half-acre lot in one of Windermere’s most sought-after communities, Windsor Hills, this FULLY RENOVATED luxury home delivers the ultimate move-in-ready, like-new lifestyle buyers are searching for. Featuring 4 spacious bedrooms, 4 beautifully updated bathrooms, and a highly desirable open-concept layout, every inch of this residence has been meticulously redesigned with today’s modern buyer in mind. The stunning chef’s kitchen is a true showpiece, appointed with brand-new premium Thermador appliances, custom cabinetry, designer finishes, and elegant lighting that elevate the entire living experience. Wide-plank luxury vinyl flooring flows seamlessly throughout the home, combining sophistication with durability and low-maintenance living. Designed for both everyday comfort and entertaining, the flexible floor plan includes an oversized upstairs BONUS ROOM, with a built-in-closet and a full bathroom, ideal for a home theater, game room, executive office, fitness studio, or private guest retreat/in-law suite. Major upgrades provide exceptional value and peace of mind, including a 2021 roof, dual high-efficiency HVAC systems (2 units/ 2026), new water heater, upgraded sliding glass doors, and an epoxy-coated garage. The expansive backyard offers endless possibilities to create your dream outdoor oasis, resort-style pool, or entertaining space. Located just minutes from the renowned Butler Chain of Lakes, championship golf courses, upscale dining, shopping, and top-rated schools, this exceptional property combines luxury, privacy, and convenience in one of Central Florida’s most desirable locations. Rarely does a fully updated home with this level of quality, land, and location become available. Some photos have been virtually staged. Furnishings shown are for illustrative purposes only and are not included in the sale.

Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)

Listing Agent: Dianna Desboyaux (407-920-4601)

Remarks: Under contract-accepting backup offers. 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 theater. Vaulted ceilings rise to a dramatic 14-foot peak as skylights and expansive double-pane windows flood the interiors with natural light. A sculptural chandelier crowns the volume, while a full-height stone fireplace ascends as the focal point. French glass doors frame panoramic views of the private rear oasis — pool, pergola, and mature canopy beyond — creating a seamless connection between interior grandeur and outdoor serenity. The chef’s kitchen commands attention. A grand Taj Mahal quartzite island defines the center. White oak cabinetry spans floor to ceiling. The Thor range and sculpted hood rise against a full-height stone backdrop. pot filler., Viking refrigerator. Glass pendants hover overhead -- Every finish carries presence. The scullery unfolds unexpected, elevated, and unforgettable — Deep olive custom cabinetry, textured tile, LED-lit shelving, beverage refrigeration, and layered storage make it as functional as it is striking. A split plan introduces the primary suite — vaulted, private, composed. A sculptural chandelier anchors the ceiling while tailored wall moldings define the room. Dual concealed walk-in closets preserve symmetry. The primary bath is a statement of design: matte stone soaking tub beneath clerestory light, full-height stone extending into a curbless marble shower, dual tailored vanities with brushed brass accents, and patterned marble floor grounding the space in immersive opulence. An adjoining vaulted extension captures pool views and opens to the lanai. The powder room shifts tone — charcoal paneled walls, sculptural marble sink, polished brass fittings, arched mirror, and bold tile creating a rich, moody presence. A formal office behind glass French doors offers focused productivity and polished presentation. An arched corridor leads to the secondary wing where three additional bedrooms offer privacy and versatility. One suite provides direct exterior access, functioning as a cabana retreat with its own en suite bath — ideal for guests or seamless indoor-outdoor living. Outdoors, the property transforms into a private compound. A covered veranda spans the rear with classical columns and herringbone flooring. The fully equipped summer kitchen, custom wood pergola lounge, expansive lawn, fresh sod, rear gate access, and lush landscaping offer scale impossible to replicate in today’s market. Villa Casablanca is not comparable to new construction. It is rarer. Extensively renovated inside out with a long list of brand new finishes - Roof, HVAC, Double pane windows, plumbing, pool refinish, level 5 drywall smooth finish and much more. Schedule your showing today.

Listing is courtesy of: COMPASS FLORIDA LLC (407-203-9441)

Listing Agent: Ahmad Hassan, Pa (718-641-9358)

Remarks: Pre-Construction. To be built. 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, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. ** Also listed as vacant land MLS S5147532 for $1,650,000

Listing is courtesy of: HOME WISE REALTY GROUP, INC. (407-712-2000)

Listing Agent: Eric Powell (407-720-1833)

Remarks: Gorgeous canal-front home with direct access to the Butler Chain of Lakes and just four blocks from the heart of downtown Windermere, this 2024 luxury remodel offers the perfect blend of modern living and small-town charm. Minutes from Food Truck Fridays, local cafés, parks, tennis courts, and year-round community events, this home blends modern elegance with the warmth of small-town living. Step inside to an open, grand gathering space framed with natural wood beams, a gas fireplace, and a seamless flow into a chef-inspired kitchen. Featuring state-of-the-art GE Monogram appliances, a Taj Mahal quartzite island, restaurant-quality crushed ice, a 100+ bottle wine cooler, a full bar and coffee lounge, and a spacious walk-in kitchen pantry—this home invites effortless entertaining. Throughout, new wide-plank laminate wood floors set a refined, cohesive tone. Additional highlights include professional designer wallpaper in the dining room and powder bath, smart bidet in the primary bath, and a fully integrated smart-home lighting, shade, and security system. The primary suite is a private sanctuary, complete with a fully reimagined spa bath wrapped in marble and porcelain, a freestanding soaking tub, and two custom-designed closets. There are three more en suite bedrooms offering privacy and convenience. This corner-lot haven is framed by mature oak trees and newly installed landscaping and irrigation. A beautiful outdoor deck and built-in fire pit creates a cozy retreat for gatherings. Follow the canal behind the home to access the world-renowned Butler Chain of Lakes. The boathouse features an electric lift, dual Sea-Doo floating docks, and instant access to some of Florida’s most coveted waterways.

Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)

Listing Agent: David Warzycha (863-860-3365)

Remarks: Experience elevated lakefront living in this one-of-a-kind estate, offering breathtaking views of Lake Bessie and unforgettable Florida sunsets. A private gated entry welcomes you to this exceptional residence, featuring 3 bedrooms and 3.5 bathrooms, plus a private in-law suite with its own full bath bringing the total to 4 bedrooms and 4.5 bathrooms. Thoughtfully designed for both everyday living and elegant entertaining, this home offers the perfect blend of comfort, privacy, and sophistication. The main level features formal living and dining rooms with a fireplace, along with a private office just off the foyer. The gourmet kitchen is a chef’s dream, showcasing custom cabinetry, built-in wine rack, wine refrigerator, Sub-Zero refrigerator, custom lighting, gas range, and a spacious pantry. A convenient half bath and oversized laundry room are also located on the main floor. Upstairs, you’ll find two private suites, each with its own full bathroom, plus the luxurious owner’s retreat offering stunning lake views, custom tile floors and walls, a separate walk-in shower, jetted soaking tub, custom lighting, and a large walk-in closet with built-in cabinetry. Step outside to your resort-style oasis featuring large pool with expansive deck and water feature. Two additional outdoor entertaining areas include a dedicated space with an outdoor kitchen. The pool house offers large windows with panoramic views, custom cabinetry, granite countertops, upgraded tile flooring, a Murphy bed, and a full custom bathroom, perfect for guests. Complete with a covered boat dock and located just a few blocks from downtown Windermere and nearby shopping, this extraordinary home blends luxury, comfort, and the ultimate Florida lifestyle.

Listing is courtesy of: ELITE GLOBAL REAL ESTATE LLC (407-758-2604)

Listing Agent: Maria Sarmiento Webel (305-793-6614)

Remarks: Under contract-accepting backup offers. 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 millwork, rich hardwood floors, and an updated chef’s kitchen featuring Viking and Thermador appliances. Warm natural light streams in through expansive window packages bracketed by plantation shutters, making the main level warm and welcoming. French doors and windows throughout the newly painted living space, breakfast room and primary suite provide sweeping views of the covered lanai and private pool in this tranquil oasis. The primary suite, with two walk in closets and a spacious bathroom with jetted tub, is on the main floor, while the second level provides an additional five bedrooms, including a versatile mini-master- perfect for multigenerational families, an au pair suite, or a flexible bonus space. An oversized side-entry 3 car garage comes equipped with built in closets, storage shelving, and car charging unit. The expansive front and back yards are unique for this neighborhood, allowing for a myriad of outdoor living options, as well as providing a sense of peace and privacy. Landscaping was recently updated after the 2026 freeze and includes one of the coveted centennial legacy trees from the town of Windermere. This gem has been well maintained, including a NEW ROOF (2021), WHOLE HOME GENERATOR with 500 gallon in ground propane tank (2023), gas fireplace remodel (2022), new AC units (2023, 2023, 2018), a built in Thermador coffee maker (2025), and a Pool Heater/Chiller (2025) that encourages swimming year round. This is truly the perfect family home- it is ideally positioned within minutes of downtown Windermere and is zoned for A rated Windermere Elementary (right around the corner). Come experience the Windermere lifestyle - a unique blend of of lake life, vibrant community, and small town charm. Residents of this neighborhood have access to the Town of Windermere Chain of Lakes private BOAT RAMPs, and downtown Windermere, with its enchanting shopping district, farmer’s market, local restaurants and brewery, is only a short bike or golf cart ride away. With easy access to major highways, downtown Orlando, Disney World, Universal Studios, Winter Garden and Restaurant Row, as well as two major hospitals, are all just minutes away. Don’t miss this rare opportunity to own a home of this caliber in the sought-after Manors at Butler Bay. Washer/Dryer, breakfast and dining rooms light fixtures do not convey.

Listing is courtesy of: REIKI REALTY LLC (407-435-8909)

Listing Agent: Nipul Shah (407-435-8909)

Remarks: Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere with excellent walkability. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are anchored by a striking floor-to-ceiling stone fireplace and beautiful library with rolling ladder, while upstairs bedrooms and bonus room are thoughtfully designed for comfort and quiet, complemented by quality finishes throughout. Recent updates include a newly installed roof (2024) and windows (2025), enhancing both peace of mind and long-term value. A spacious three-car garage adds both convenience and functionality. Outdoors, the home transitions easily to an entertainer’s retreat with covered porches, fireplace, outdoor kitchen, circular firepit, cabana bath, Tiki hut and lush landscaping. The property also offers the opportunity to add a FRONT GATE for enhanced privacy and security, and allows for a FUTURE POOL ADDITION, giving buyers flexibility to further customize the outdoor living experience. Deeded town resident access to the Butler Chain of Lakes and a prime location within Windermere’s vibrant town center with its new redevelopment complete this rare offering where architectural integrity meets a fun and functional Florida lifestyle.

Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)

Listing Agent: Kari Fleck (407-925-5283)

Remarks: 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.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)

Remarks: Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)

Listing Agent: Monica Lochmandy (407-230-6888)

Remarks: Pre-Construction. To be built. Pre-Construction. To be built. Pre-Construction | To Be Built | Designed for Unparalleled Luxury Discover an extraordinary opportunity to own a masterfully designed luxury residence in this Windermere community. This exquisite estate, crafted by the renowned Supreme Construction, offers a perfect blend of sophistication, innovation, and timeless elegance. Property Highlights: • Total Living Area: 3,889 Sq. Ft. | Total Building Area: 5,516 Sq. Ft. • 4 Bedrooms | 4 Full Baths | 1 Powder Room | 1 Pool Bath • Expansive Living Spaces with High Ceilings & Open Floor Plan • Great Room | Dining Room | Gourmet Kitchen with Nook & Pantry • Private Elevator & Multiple Open Decks • 2-Car Garage First-Floor Features: • Grand Foyer with Staircase & High Ceilings • Great Room & Elegant Dining Room • Chef’s Gourmet Kitchen with custom cabinetry, quartz countertops, Subzero appliances, and a spacious island • Guest Suite with Private Bath & Walk-in Closet • Laundry Room & Powder Bath • Pool Bath (Outdoor Access) Second-Floor Features: • Lavish Master Suite with Private Balcony, Spa-Inspired Bath & Custom Walk-in Closet • Two Additional Bedrooms with Walk-in Closets & Shared Designer Bathroom • Two Expansive Open Decks for Outdoor Enjoyment Luxury Amenities & Smart Home Features: • State-of-the-Art Smart Home Integration • Hurricane Impact Windows for Safety & Efficiency • Custom California Closets in All Bedrooms • Heat & Glow Fireplaces in the Living Room & Master Suite • Large Format Porcelain Tile & High-End Finishes Throughout • Flat Tile Roof & Metal Truss Construction for Durability Outdoor Oasis & Entertainment Haven: • Resort-Style Custom Pool & Spa (Separate Permit) • Sunken Outdoor Kitchen & Lounge Area for Elevated Entertaining • Landscaped Backyard with Ample Space for Relaxation & Gatherings Prime Windermere Location – Unmatched Lifestyle & Convenience: • Minutes from Isleworth, Home to Celebrities & Sports Icons • Access to the Pristine Butler Chain of Lakes – Ideal for Boating & Water Sports • A-Rated Schools, Parks, & Year-Round Community Activities • Close to Luxury Shopping, Fine Dining, Golf Courses & Entertainment • Easy Access to Disney, Universal, and Orlando’s Top Attractions This exceptional luxury estate embodies a lifestyle of sophistication, exclusivity, and modern convenience. Secure this once-in-a-lifetime opportunity to own a masterpiece of design and craftsmanship in the heart of Windermere. For more details, floor plans, and customization options, contact us today!

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Matthew Hughes (407-619-4717)

Remarks: Lakefront estate on Lake Down in the Butler Chain of Lakes with over 150 feet of frontage and no HOA in Sunset Bay. Built in 1983, this 5 bedroom, 4 bath pool home offers nearly 7,000 square feet across three levels and presents a rare opportunity to renovate a true chain-of-lakes property to your own style and standards. Home retains much of its original character and is priced accordingly, creating strong value for buyers seeking premier waterfront frontage, square footage, and long-term upside in one of Windermere’s most desirable locations. Main level includes kitchen, dining area, secondary bedrooms, full baths, oversized laundry room, and sliding doors opening to covered outdoor living and lake views. A few steps down, the sunken living room features a bar, fireplace, storage, and direct water views. Upstairs, the primary suite includes a fireplace, large walk-in closet, dual vanities, tub, separate shower, and screened balcony overlooking the lake. This level also includes a private office. The lower level is a standout feature, offering a full basement living space with its own kitchen, living room, bedroom, full bath, and direct pool access, ideal for extended family, guests, or multigenerational living. An additional reinforced interior room provides flexible use as a secure safe room, storm shelter, private storage room, or secluded flex space. Outdoor features include a screened pool, covered entertaining area, fenced yard, and private dock with space for two boats and two jet skis. Garage space accommodates up to 6 cars, plus a 2-car carport and a large circular driveway that provides additional parking for guests, larger households, or recreational vehicles. Additional storage areas and the lower-level garage create excellent space for boat gear, kayaks, paddle boards, trailers, and lakefront equipment. Home is priced in line with its recent appraisal, with the value reflecting both its current condition and the renovation investment a future owner may choose to make. For buyers seeking a large lakefront footprint, multigenerational layout, extensive parking, and the ability to modernize to today’s standards, this property offers a rare value on the Butler Chain. Located minutes from downtown Windermere, Restaurant Row, golf, shopping, and major attractions.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Phil Mariani (407-257-3609)

Remarks: ADU A beautiful home located in the heart of downtown Windermere offering 4-bedrooms, 3-bathrooms, with a perfect blend of comfort and convenience. The house features hardwood floors throughout, and large sliders that open to a beautiful backyard. This is a great home for entertaining or relaxing. This property features a fully equipped ADU with one-bedroom, one-bathroom space, ideal for in-laws, guests, or use as a private office. Located minutes from boat ramps and local amenities. Please schedule your viewing today.

Listing is courtesy of: IRIS INTERNATIONAL (407-448-5085)

Listing Agent: Robert Trien (407-484-8474)

Remarks: Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.

Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)

Listing Agent: Dianna Desboyaux (407-920-4601)

Remarks: Under contract-accepting backup offers. Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the property's beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Florida's finest communities.

Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)

Listing Agent: Monica Lochmandy (407-230-6888)

Remarks: Welcome to a residence that transcends even the highest expectations of luxury living! This is a once-in-a-lifetime estate where architecture, scale, and location combine to create an experience that is as rare as it is breathtaking. From the moment you arrive, the home commands attention with a grand, Mediterranean-inspired façade that opens to interiors of soaring scale and meticulous marble craftsmanship. Light cascades through walls of glass, illuminating a series of living spaces designed for entertaining at the highest level. Every detail speaks of refinement: bespoke millwork, hand-selected stone, intricate ceiling treatments, and custom finishes curated with an uncompromising standard. The expansive chef’s kitchen blends culinary excellence with artful design, while the bar, wine room, and multiple gathering spaces ensure that every occasion, from intimate family dinners to grand celebrations, is unforgettable. The state-of-the-art theater begs you to slow down and enjoy the latest movie release. Conveniently adjacent to the theater is a home gym and lakefront cardio room that rivals most commercial gyms! Once the day winds down, the private retreats within the home offers warmth and convenience so you never have to leave. The first floor conveniently offers a full guest suite, and the second floor boasts an additional four bedrooms all with en-suite bathrooms. Additionally located on the second floor is a kid’s study, playroom, guest apartment and handsome cigar room. Outdoors, the estate transforms into a private resort. A sweeping terrace frames an oversized resort style pool and spa, surrounded by gardens, fountains, and tranquil seating venues. Enjoy the piece of your surroundings, from al fresco dining beneath the pergola to evenings spent overlooking Lake Olivia, one of Central Florida’s most sought-after ski lakes. Beyond the main residence, a detached guest retreat and showcase garages offering space for up to 14 cars will satisfy the most serious car collector. Set on a significant 4.43 acre parcel of land, the estate is both sanctuary and statement, offering numerous spaces to live, create, and entertain. Enjoy living in the heart of it all without compromising your privacy. Plus, with easy access to major highways, theme parks, downtown Windermere, and less than 10 minutes from Whole Foods, Restaurant Row, and championship golf courses, you’re never far from the very best of what Central Florida has to offer. Perfectly positioned with easy access to Windermere Prep, Lake Highland, and Montverde Academy...this location does not get any better! Rarely does a property of this magnitude become available. This is not simply a home — it is an heirloom, a landmark, and an invitation to experience luxury on a level few will ever know. Call today for an exclusive private showing.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Julie Bettosini, Pa (321-689-9594)

Remarks: 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 private courtyard featuring a glistening pool adorned with a cascading waterfall from the pergola. An expansive covered patio houses a summer kitchen, pool bath, and attached third bedroom accessed only from the courtyard. The heart of this home is a chef's dream, with a gourmet kitchen featuring top-of-the-line Wolf appliances, striking custom cabinetry, and an open design that seamlessly connects to the family room and dining areas. The grand primary suite offers a private sitting area overlooking the peaceful pond, double walk-in closets, and a spa-like bath complete with a Jacuzzi tub and an expansive walk-in shower. The third garage was converted into a gym with air conditioning and can be converted back to additional garage space. Garden villas offer carefree living with exterior grounds maintenance included in the separate monthly fees. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Rob Rahter (407-497-4526)

Remarks: 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 spanning more than 14,444 square feet of living space and 11 bedrooms across both residences. Welcome to this one-of-a-kind haven of privacy and prominence showcasing the best of Central Florida living. Set on a rare 3.75 acres commanding enviable views on the northern shore of Lake Butler, every detail has been thoughtfully designed to celebrate both refinement and tranquility. The impressive palatial main residence boasts 10,649 square feet of living space with 6 bedrooms plus a one-bedroom guest retreat and an array of curated spaces. The Spanish Eclectic interior fuses classic craftsmanship with modern sophistication, creating an inviting and awe-inspiring escape from the ordinary. On entrance be greeted by sweeping floor to ceiling windows to allow breathtaking water vistas, double-sided gas fireplace, a grand colonnade hallway, and architectural details throughout. The gourmet chef’s kitchen features top of the line appliances, gas range with multiple burners, ovens, island with second sink, and walk-in pantry. A sports bar games room and showstopping home theater provide an abundance of entertaining options. Other notable amenities include a Castilian wine cellar, bay windows, two wet bars, private salon, elevator, gym, steam room and sauna. Outdoors, a generous summer kitchen with automatic roller screens provide an outdoor oasis for al fresco dining, cooking, or relaxing. The zero-entry infinity pool and vast resort decking provide a breathtaking vantage point for panoramic views of Lake Butler’s radiant sunsets, while the shaded Zen garden and white sandy beach offer a tranquil retreat for quiet reflection. With many distinct outdoor venues, serenity is never far away. The estate’s private island, accessed by an electric drawbridge, and a boat ramp provide unmatched exclusivity to Lake Butler and the world-famous Butler Chain of Lakes. The two-story detached guest house offers 3,795 sq feet of living space across two, 2-bedroom apartment homes, each with kitchens, laundry rooms, an elevator, and attached two-car garage. Built for a large multi-generational family, guest quarters, or on-site caretakers, the possibilities are endless. Truly a picture-perfect unmistakable showplace offering the very best for the most discriminating buyer.

Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)

Listing Agent: Julie Bettosini, Pa (321-689-9594)

Remarks: This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent upgrades—including a new roof, new insulation, new tile floors, new kitchen cabinets and countertops, new stainless steel appliances, fresh interior and exterior paint, and updated lighting fixtures-add modern elegance throughout. The east-facing design bathes every room in golden sunsets, creating a warm and inviting atmosphere. Set on 1.4 acres with no mandatory HOA, the property boasts a huge driveway with space for RV or boat parking, along with a twin boat slip dock and covered boat house. Perfectly located near top-rated schools, shops, restaurants, attractions, and major roads, this home is ideal for those seeking the Floridian way of life—where swimming, fishing, jet skiing, and year-round relaxation are just steps from your back door.

Listing is courtesy of: INTERNATIONAL NETWORK REALTY (407-963-8539)

Listing Agent: Wui Keong Goh (407-963-8539)