Windermere Homes with Mediterranean Architectural style

Windermere Homes with Mediterranean Architectural style

Welcome to Windermere, Florida, a picturesque town nestled in the heart of Orange County. Known for its lush landscapes and serene lakes, Windermere offers a unique blend of small-town charm and modern elegance. This vibrant community is surrounded by the stunning Butler Chain of Lakes, providing residents with abundant opportunities for outdoor activities such as boating, fishing, and hiking. With its friendly neighborhoods and top-rated schools, Windermere is an ideal place for families and individuals seeking a tranquil yet engaging lifestyle.

One of the standout features of Windermere is its captivating Mediterranean architectural style homes. These stunning residences are characterized by their warm, earthy tones, red-tiled roofs, and intricate stucco exteriors, evoking a sense of timeless elegance and sophistication. Inside, you'll find spacious open floor plans, grand archways, and luxurious finishes that create an inviting atmosphere perfect for entertaining or relaxing. Many of these homes boast expansive outdoor living spaces, complete with lush gardens and sparkling pools, allowing you to fully embrace the Florida sunshine.

Living in Windermere means enjoying a close-knit community with easy access to upscale shopping, dining, and recreational activities. Whether you’re strolling through the charming downtown area or participating in local events, you’ll find a welcoming environment that makes you feel right at home. If you’re dreaming of a life filled with beauty and tranquility, explore the Mediterranean-style homes in Windermere and discover your perfect oasis in this enchanting town.

Newest Windermere Homes with Mediterranean Architectural style

11103 Bridge House Road, Windermere
$6,750,000
5 Beds ⋅ 8 Baths ⋅ Reserve At Lake Butler Sound 45/120 SubDv. ⋅ 34786 Zip Code
Elegance defines this lakefront estate perched along the shores of Lake Butler, set behind the guarded-gates of the coveted Reserve at Lake Butler Sound—one of Windermere’s signature communities. This commanding residence offers 5 bedrooms, including 4 in the main house and a private guest-house suite that also features a show-stopping movie theatre and a downstairs entertainment room complete with bar and stage. A dramatic foyer introduces the formal living room, where soaring arched windows frame serene lakefront views beyond the resort-style pool and tropical surroundings. The upscale ambiance is elevated by a floor-to-ceiling custom stone fireplace, classic columns, tile flooring, and a seamless flow into the polished formal dining room, enhanced by an air-conditioned, glass-enclosed wine wall. The chef’s kitchen showcases rich wood cabinetry, a marble-topped island with seating, and ornate pendant lighting. Dark stone countertops, a custom tile backsplash, Wolf appliances, gas cooktop, Sub-Zero refrigerator, and built-in vegetable steamer create a refined and highly functional workspace, all enriched by natural light and warm architectural details. The breakfast area and spacious family room open to the outdoor living spaces through fully retractable L-shaped doors. The primary suite features new carpeting, a sitting area, French doors to the pool patio, and a luxurious bath with soaking tub, generous walk-in shower with triple showerheads, and a spiral staircase leading to a flex space transformed into an oversized closet. Also on the main level are an office, half bath, laundry room, and mudroom. A dramatic staircase leads to the second-floor family room and three additional bedroom suites. Outdoor living includes a covered family room with fireplace, tranquil koi pond surrounded by lush landscaping, tiled pool decking, heated saltwater pool and spa, and a covered boat dock on Lake Butler. Additional features include Savant whole-home music, a Generac generator powering 75% of the home, and distinguished neighborhood with roving security, community park, fishing pier, and back gate access to SR 535 and Windermere Prep. Home furnishings available separately.

11103 Bridge House Road, Windermere
7230 Sangalla Drive, Windermere
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Casa De Lago Rep SubDv. ⋅ 34786 Zip Code
Original-owner David Weekley Mediterranean in gated Casa Del Lago, on the coveted east side of Windermere near Isleworth and Keenes Pointe, minutes from Walt Disney World and an easy walk to Sunset Park Elementary.From the moment you step inside, rich hardwood floors draw you through the study, formal dining room, family room, and primary suite, giving the home a warmth and continuity rarely found at this price point. The gourmet kitchen is the heart of it all, with 42" cabinetry, granite counters, a cooktop crowned by a designer vent hood, and stainless GE appliances, all open to the family room so no one misses the conversation. Sliders lead to an expansive covered lanai and a generous backyard with plenty of room for a pool, a garden, or simply space to breathe. A 3-car garage handles vehicles, toys, and storage with ease. Cared for by a single owner since David Weekley handed over the keys, this home delivers the Windermere address buyers are searching for. Gated privacy, top-rated schools, and Winter Garden Village shopping and dining are all minutes away, with quick access to the 429 and the charm of Downtown Windermere.

7230 Sangalla Drive, Windermere
8214 Serenity Spring Drive Unit 2405, Windermere
$350,000
3 Beds ⋅ 3 Baths ⋅ Oasis Cove 2/Lakeside Village Ph X SubDv. ⋅ 34786 Zip Code
Live about as close to the magic as you can get without a Disney address. This home in gated Oasis Cove sits just 3 minutes from Disney property, so park days, dinner reservations, and fireworks nights are a quick drive instead of a trip. The 3 bed, 2.5 bath layout offers 1,512 sq ft and a 1-car garage, with upgraded flooring on the stairs and throughout the upper level. The HOA covers the roof, lawn care, and water, so electricity is your only utility bill, and the HVAC was replaced in 2024. Spend your free time at the resort-style pool and community amenities, or at the parks down the road, instead of maintaining a home. It works equally well for full-time residents and seasonal owners. Zoned for A-rated schools from elementary through high school. Buyer to verify school assignment, HOA coverage.

8214 Serenity Spring Drive Unit 2405, Windermere
11066 Ullswater Lane, Windermere
$3,600,000
5 Beds ⋅ 7 Baths ⋅ Reserve At Lake Butler Sound SubDv. ⋅ 34786 Zip Code
Experience luxury living in the heart of Orlando, with a 24-hour guard-gated Reserve at Lake Butler Sound in Windermere! Situated on an expansive 0.83-acre homesite, this stunning Mediterranean-inspired estate offers over 7,200 square feet of elegant living space, featuring 5 bedrooms, 6.5 bathrooms, and a spacious 4-car garage. Impressive architectural details, soaring ceilings, elegant finishes, and generous living areas create the perfect blend of sophistication and comfort. The beautifully designed kitchen opens to inviting gathering spaces, while the luxurious primary suite offers a private retreat. Step outside to your own resort-style oasis featuring a sparkling pool, outdoor kitchen, and expansive grounds ideal for entertaining. Ideally located near premier shopping, dining, golf, and world-class attractions. A rare opportunity to own an exceptional estate in one of Windermere's most sought-after communities. Schedule your private showing today!

11066 Ullswater Lane, Windermere
17538 Black Rail Street, Windermere
$1,189,000
5 Beds ⋅ 5 Baths ⋅ Enclave SubDv. ⋅ 34786 Zip Code
WATER VIEW! DISNEY FIREWORKS! 4,999 SQ FT OF LIVING SPACE! TWO PRIMARY SUITES, ONE ON EACH FLOOR! 3 CAR GARAGE! Located in the desirable Enclave community of Windermere, this spacious 5 bedroom home offers an exceptional floor plan with a primary suite on the first floor and a generously sized primary retreat upstairs. Highlights include expansive living areas, formal dining room, private office, dedicated Media Room, and a large upstairs Loft, offering plenty of space for entertaining, relaxing, and everyday living. The spacious kitchen features a pantry and ample storage, complemented by a covered lanai overlooking the water. A well designed Mudroom with extensive custom cabinetry and generous storage, plus a central vacuum system, adds everyday convenience. Beautifully maintained, this residence combines generous living space, comfort, and versatility, with excellent potential to personalize its interiors to your own style. Enjoy the best of Windermere living with beautiful water views, Disney fireworks in the distance, and an exceptional combination of space, functionality, and location.

17538 Black Rail Street, Windermere
5092 Isleworth Country Club Drive, Windermere
$8,500,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

5092 Isleworth Country Club Drive, Windermere
9310 Isleworth Gardens Drive, Windermere
$3,595,000
3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pantry. A stone fireplace provides a focal point in the living room, while the spacious family room opens through panoramic sliding doors to a covered lanai, extending the living spaces naturally outdoors.The primary suite offers a private retreat with a morning bar, sitting area, spa-inspired bath and generous walk-in closet. A wood-floored study with custom built-ins provides an elegant setting for work, while additional bedrooms offer comfort and privacy for family and guests. Additional interior highlights include the laundry room, powder bath, and a three-car garage.Beyond the interiors, the home embraces its lush garden setting with tranquil pond views and an expansive outdoor living area. The covered lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa, creating a private setting for relaxed afternoons and beautiful entertaining. The Gardens of Isleworth offer convenient living in a beautiful setting within Central Florida’s most iconic golf course community.

9310 Isleworth Gardens Drive, Windermere
11532 Waterstone Loop Drive, Windermere
$2,199,000
4 Beds ⋅ 6 Baths ⋅ Waterstone SubDv. ⋅ 34786 Zip Code
SINGLE STORY LIVING and PRIVATE PEDESTRIAN-GATED ACCESS to WINDERMERE PREPARATORY SCHOOL from within the community distinguish this custom Waterstone home. Built in 2014 and located behind a staffed, guard-gated entrance, the residence offers approximately 4,169 square feet, four bedrooms, four full baths, two half baths, and a three-car garage. Two stately palms welcome you to the beautifully landscaped 0.44-acre homesite, while landscape lighting highlights the grounds after sunset. From the moment you enter, the view opens to the CENTRAL COURTYARD, SALTWATER POOL, and SPA. Direct access from the kitchen, family room, and primary suite makes the courtyard part of daily life. Covered lanais, generous lounging areas, a summer kitchen with a full-size motorized screen, and an outdoor fireplace provide space to gather and dine outdoors. The courtyard has been freshly painted, and the travertine pavers were recently sealed. Inside, soaring ceilings, tray details, crown molding, and expansive windows bring light and courtyard views into the living spaces. The kitchen features Wolf and Sub-Zero appliances, rich wood cabinetry, dual islands, bar seating, and a concealed walk-in pantry. The spacious primary suite includes hardwood flooring, a sitting area, two expansive custom walk-in closets, and a bath with a soaking tub, oversized rainfall shower, and generous vanity space. An adjoining flex room can serve as a home office, gym, or private retreat. Additional features include two newer air-conditioning units serving the multizone HVAC system, a sound system throughout the indoor and outdoor living areas, a whole-house Lorex camera system, a porte-cochère, and an expansive paver driveway. Waterstone is near Windermere High School, with convenient access to Winter Garden Village, Lakeside Village, Walt Disney World, and major Orlando routes. Schedule a private showing to experience this distinctive Windermere courtyard home.

11532 Waterstone Loop Drive, Windermere
8142 Tibet Butler Drive, Windermere
$2,685,000
5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf Course. Be welcomed by a grand foyer that flows seamlessly into a formal dining room: a refined, inviting space that blends timeless architectural character with luxury finishes. Framed by exposed wood beams, arched wall details, and wrought iron accents, the room feels warm yet grand. Nearby, the living room offers a more relaxed ambiance that elevates everyday living while providing a sophisticated backdrop for entertaining. An expansive primary bedroom and bathroom suite, office, and pool bath are located off the foyer. The chef’s kitchen feature stainless steel appliances—including a double oven and built in refrigerator—that create a seamless, upscale workflow, while the adjacent breakfast nook provides a sunlit place to enjoy morning coffee. A secondary suite on the first floor is perfect for visiting guests. Three upstairs bedroom suites share a common space for homework or socializing and a large bonus room with bar and balcony is a favorite place to entertain friends. A designated home theater is perfect for relaxing while enjoying favorite shows. Outside is a summer kitchen, fireplace, and lounge area for enjoying the Florida weather. The large resort-style pool and spa with waterfall complete the setting. Home is located across the street from the golf course driving range. 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.

8142 Tibet Butler Drive, Windermere
4201 Isabella Circle, Windermere
$3,990,000
6 Beds ⋅ 7 Baths ⋅ Casabella SubDv. ⋅ 34786 Zip Code
Welcome to this beautifully furnished luxury residence in the guard-gated community of Casabella in Windermere. Situated on a private half-acre homesite, this impressive Toll Brothers Villa Divina model offers approximately 6,881 square feet of thoughtfully designed living space featuring 6 bedrooms, and 7 full bathrooms. The home showcases elegant architectural details, soaring ceilings, abundant natural light, and expansive living areas designed for both everyday comfort and entertaining. The gourmet kitchen features premium appliances, custom cabinetry, an oversized island, generous workspace, and a seamless connection to the family room and dining areas. The first-floor primary suite provides a private retreat with a spa-inspired bathroom featuring dual vanities, a walk-in shower, and spacious closet areas. Additional bedrooms, a second-floor media room, loft, office, and flexible living spaces provide exceptional versatility. The outdoor living area features a private in-ground pool, covered lanai, and beautifully landscaped surroundings. Additional highlights include a three-car garage, tile roof, refined finishes, abundant storage, and carefully selected furnishings throughout. Offered fully furnished, this residence provides a seamless opportunity to enjoy Windermere living in one of Central Florida’s desirable gated communities. Conveniently located near premier shopping, dining, golf, entertainment, major roadways, and area attractions, this Casabella estate combines elegance, comfort, and convenience.

4201 Isabella Circle, Windermere
6055 Louise Cove Drive, Windermere
$6,850,000
5 Beds ⋅ 6 Baths ⋅ Isleworth West SubDv. ⋅ 34786 Zip Code
Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms- of which, four are on the ground floor – plus office, gym, library, storage room, upstairs media room and downstairs bonus room, perched along Lake Louise, the only lake on the Butler Chain surrounded by Isleworth. Expansive formal and living spaces are highlighted by picturesque lake views. The seamless flow from room to room takes full advantage of a layout built for living. The chef’s kitchen with island, gas cooktop, stainless appliances, hidden walk-in pantry, and built-in hutch offer an abundance of space for entertaining or family gatherings. The primary retreat offers an escape from the ordinary with peaceful lake views, a master bath with jetted tub, garden and water view shower, and a showstopping two-story custom closet that will be the envy of all. The executive office with wood walls and built-in shelving offers a luxurious setting for attending to business from home. Three secondary bedrooms on the main floor are all spacious and feature ensuite bathrooms. Upstairs is a fourth bedroom, gym, library, and open media room with balcony. Outdoor amenities include a screened patio with summer kitchen, oversized resort-style pool with travertine decking, large green space, and private dock with covered boat lift plus dock-mounted jet-ski lifts, and 3-car garage. Home also includes a full-house generator. This coveted location within Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional membership opportunities.

6055 Louise Cove Drive, Windermere
9679 Westover Roberts Rd, Windermere
$3,400,000
6 Beds ⋅ 7 Baths ⋅ 34786 Zip Code
Spectacular Private Lakefront Estate on Lake Olivia, Windermere Near The Grove Shops & Restaurants. Enter through custom Iron gates to this extraordinary Mediterranean estate set on 1.75 private acres along the shores of Lake Olivia. Featuring six bedrooms, all with ensuite baths, this exceptional home offers nearly 6,000 square feet of living space, mature landscaping, and no HOA. Ideal for multigenerational living, the attached one-bedroom in-law apartment features a private entrance, full kitchen, living area, and ensuite bedroom—perfect for extended family or guests. The chef’s kitchen is a showstopper, featuring double islands, granite countertops, a professional Wolf gas range with double ovens, a 48-inch Sub-Zero refrigerator/freezer, a wine fridge, and a butler’s pantry. Elegant finishes, formal living and dining rooms, and a private upstairs media/game room complete the interior. Enjoy Florida living in the expansive 1,200+ sq. ft. screened lanai with remote hurricane shutters, summer kitchen, stone fireplace, and a stunning lagoon-style saltwater pool with heart-shaped spa. The luxurious primary suite offers French doors overlooking the pool and lake, custom closets, and a spa-inspired bath. Boating enthusiasts will love the oversized boathouse, screened dock room, motorized boat lift, and direct access to Lake Olivia, a private spring-fed lake with no public access, ideal for boating, waterskiing, and fishing. Over $200,000 in recent enhancements include a whole-house generator, new A/C system, updated lighting and ceiling fans, remote hurricane shutters, Leaf Guard gutters, roof tile servicing and sealing, new side pavers, and fresh interior paint. A rare opportunity to enjoy privacy, luxury, and true multigenerational living on one of Central Florida’s most desirable private lakes. Convenient to shopping, major highways, and area attractions. Move-in ready! 360° virtual tour and floor plan available. Seller may consider a Lease Purchase Option.

9679 Westover Roberts Rd, Windermere
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