luxury contemporary house for sale Windermere, United States

One or more photo(s) has been virtually staged. Located in Orlandos coveted 32836 zip code just moments from the Windermere border, this fully reimagined Cypress Isle residence blends refined design, architectural character, and an exceptional Central Florida lifestyle in one unforgettable setting. Tucked within a quiet enclave surrounded by the Lake Butler Nature Preserve and the world-renowned Butler Chain of Lakes, this home offers the rare feeling of privacy and serenity while remaining just minutes from Disney, world-class dining, premier shopping, and top-rated schools. From the moment you step inside, the soaring ceilings and dramatic open foyer create an immediate sense of arrival. Natural light pours through oversized windows, illuminating the home's warm contemporary finishes and thoughtfully designed spaces. The homes most striking architectural features are the vaulted ceiling and the open upstairs landing and catwalk, overlooking the main living area below creating a stunning visual connection between both levels and adding a sense of openness rarely found at this price point. Designed for both elegant entertaining and everyday comfort, the open-concept layout seamlessly flows from formal living and dining spaces into a beautifully appointed chefs kitchen featuring quartz countertops, custom stainless steel appliances, and an oversized island made for gathering. Luxury vinyl and ceramic tile flooring, oversized doors, and updated double-pane windows elevate the interior with both style and functionality. The first-floor primary suite is a private retreat, complete with tranquil conservation views, dual vanities, a freestanding soaking tub, and an expansive double shower designed to feel like a luxury spa experience. Upstairs, three additional bedrooms are connected by the dramatic open-air landing that gives the home its signature character and architectural appeal. Sliding glass doors lead to a covered lanai and screened pool overlooking lush conservation, offering peaceful mornings, sunset evenings, and year-round indoor-outdoor living. Major 2024 upgrades include new AC, water heater, pool and spa heater, water softener, irrigation system, and gas connection providing peace of mind and modern efficiency for years to come. Set among custom estates and natural beauty in one of Central Floridas most sought-after locations, this is more than a home its a lifestyle defined by space, privacy, connection, and timeless design. From Winter Garden Vineland Road turn onto Sunset Blvd, turn right onto Trout Rd, turn right into driveway.

Nestled within Phillips Grove—a private, gated Pulte community in the absolute heart of Dr. Phillips—this fully furnished, contemporary two-story estate offers a sophisticated lifestyle just moments from the renowned Restaurant Row, Walt Disney World, and Orlando's premier destinations. Meticulously maintained and showcasing over $220,000 in bespoke upgrades, this striking 7-bedroom, 4.5-bathroom residence is a masterclass in refined design. A sun-drenched foyer flows effortlessly into the formal dining room and an expansive family room. The gourmet kitchen serves as the home's centerpiece, boasting sophisticated grey cabinetry, an oversized presentation island, a walk-in pantry, and a charming breakfast nook. Outfitted for the culinary enthusiast, it features premium appliances including a gas range and double ovens. The main-level primary suite is a serene, private sanctuary complete with a dedicated sitting area, direct lanai access, and a spa-like bath featuring dual vanities and a rain-head walk-in shower. A newly completed, custom-designed boutique closet elevates the space. A second main-floor bedroom, accessed via elegant French doors, offers the perfect footprint for a sophisticated home office, private sitting room, or guest suite. The back outdoor oasis is designed for seamless indoor-outdoor entertaining, expansive sliding glass doors open to a resort-style backyard paradise. A covered lanai, already plumbed for a future summer kitchen, overlooks a pristine heated (gas) saltwater pool and spa, complete with elegant deck jets and a sun shelf. The fully fenced grounds feature lush, manicured landscaping and premium, maintenance-free artificial turf, creating a private and pristine backdrop.Upstairs, a spacious loft and a dedicated media/flex room provide exceptional spaces for entertainment or leisure. Five additional bedrooms—each featuring walk-in closets—are complemented by three full baths and a beautifully appointed laundry room. Every detail of this home has been curated for comfort, security, and energy efficiency. This exceptional residence is further distinguished by the coveted advantage of natural gas — a refined luxury feature celebrated for its superior efficiency, precision performance, and enduring reliability — thoughtfully servicing the tankless water heaters, pool heater, and gourmet cooktop for elevated everyday living.Designer lighting installations, timeless plantation shutters, and automated electric blinds in the primary suite. An architectural wrought-iron staircase featuring custom stair doors. 2 tankless gas water heaters and shatter-resistant window tinting designed to optimize energy efficiency. An integrated Tesla Universal Wall Connector for effortless electric vehicle charging. Residents of Phillips Grove enjoy a lifestyle enriched by premier, resort-style amenities. The gated enclave features a sparkling community pool with a splash zone, outdoor grilling areas, a playground, a sports field, a basketball half-court, and dedicated tennis and pickleball courts. Offering unmatched proximity to world-class attractions, top-rated schools, and major thoroughfares, this exceptional estate truly epitomizes the pinnacle of luxury and convenience in Dr. Phillips.

Welcome to this exceptional property in the sought-after Magic Village Yards community in Kissimmee. This turnkey fully furnished home offers a truly unique living experience with four bedrooms and four baths, all thoughtfully designed with plenty of closet space on the second floor for added convenience and privacy. As you step inside, you'll be greeted by a warm and inviting atmosphere, thanks to the open layout that allows natural light to flood the space. The stylish fixtures, neutral decor, and remarkable ceilings create an elegant and contemporary ambiance, perfect for any discerning homeowner. The kitchen is a chef's dream, boasting granite counters and top-of-the-line major appliances. With its spacious design, it can easily accommodate guests who love to watch the culinary action unfold. The classic island configuration maximizes the workspace and provides flexibility for meal preparation and entertaining. Location is everything, and this home is ideally situated in proximity to some of the most popular attractions in Central Florida. Disney Springs, Walt Disney World, Universal Studios, Animal Kingdom, Magic Kingdom, and LEGOLAND, along with a wide array of restaurants and shopping malls, are just a stone's throw away.

Amazing location and contemporary architecture! For the first time on the market by its original owners, this residence is exceptionally well maintained, as it has been used exclusively as a family vacation home and has never been rented short term. Beautiful and spacious with an open floor plan, this home offers four bedrooms and four baths, and it's strategically in the gated community of Magic Village Yards. This turnkey home features an open floor plan with high ceilings, a gourmet kitchen with an oversized island and breakfast nook, and a first floor and another on the second floor, primary bedroom suite. Three additional en-suite bedrooms are upstairs, offering comfort and privacy for all guests. Ideally just minutes away from Disney, top attractions, exceptional dining and shopping, this residence is ideal for a vacation home or a high-performing future short-term rental investment. Short-term rental is allowed. Schedule your showing today.

This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately introduces the home's refined aesthetic, offering a direct line of sight to the gorgeous herringbone white oak floors in the great room and the sparkling pool just beyond the full glass doors. Anchored by a sleek linear gas fireplace with custom built-ins and floating shelves, the great room provides an inviting yet sophisticated gathering space. The open-concept chef's kitchen is a showpiece in both form and function. Outfitted with Wolf and Sub-Zero appliances, it boasts an eight-burner range with one-and-a-half ovens, an oversized Sub-Zero French door refrigerator with a freezer drawer, a built-in microwave drawer, and a walk-in pantry featuring a wine and beverage tower. Marble counters in all baths continue the home's commitment to refined finishes. The main level primary suite is a serene retreat with a spa-inspired bath featuring a large glass-enclosed shower, separate soaking tub framed by dramatic four-by-ten-foot porcelain slabs, a custom walk-in closet, and a private water closet. A flexible fifth bedroom with an ensuite bath offers the perfect option for an office or den. A striking glass-railed staircase leads to the second level, where a spacious lounge area opens to a private covered patio. Three additional ensuite bedrooms, each with custom closet systems, complete the upstairs living quarters. Designed for indoor-outdoor living, the expansive covered lanai includes a summer kitchen with a grill, hood vent, refrigerator, sink, and a dedicated half bath. Overlooking lush landscaping with tropical Clusia hedges and Foxtail palms, the brand-new pool is finished with designer tile that lends a stylish, resort-quality flair. Additional highlights include a spacious storage closet under the staircase, oversized two-car garage, 500-gallon propane tank for easy generator connection, stone paver driveway and durable metal roof. Wonderfully located in a picturesque neighborhood, the property is just minutes from the boutiques and dining of Park Avenue, top-rated public and private schools and offers convenient access to downtown Orlando, the attractions, as well as area airports. A rare opportunity to own a newly constructed home of such quality and craftsmanship in one of Winter Park's most sought-after neighborhoods.

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today's lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home's long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park's sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private courtyard entrance sets the tone, creating a serene arrival and sense of retreat from the moment you step onto the property. Inside, polished concrete floors and an open, light-filled layout define the home's contemporary aesthetic, with clean lines and seamless flow designed for everyday living and effortless entertaining. Step outside to your own private oasis- complete with a pool and tranquil outdoor spaces- perfect for enjoying Florida living year-round. The home's prime location allows for an exceptional lifestyle- just a short stroll to Park Avenue's renowned shops and dining and an even shorter stroll to the golf course. Offering a unique combination of modern design and in-town convenience, this is Winter Park living at its most elevated.

Tucked along one of Winter Park's charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home's inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and effortlessly refined. Inside, light pours through expansive picture windows, illuminating marble floors that flow seamlessly through the living room, dining area and kitchen. Every space has been thoughtfully curated by New York City–based interior designer Paulette Pascarella, where classic architecture is elevated by contemporary finishes and a restrained, sophisticated palette. The new kitchen serves as a centerpiece and a gathering space, featuring custom cabinetry, quartz countertops with a full-height backsplash and a high-end appliance suite anchored by a Bertazzoni refrigerator, equally suited for everyday living or intimate entertaining. Just beyond, the family room or den introduces warmth and texture with beautiful wood floors and custom built-ins designed for function and form. Motorized shades by The Shade Store, lighting by Visual Comfort and Currey, and hardware details by Buster + Punch are layered throughout the home, complemented by exquisite textile selections from Brunschwig, Schumacher, Thibaut, and Cowtan & Tout, each detail quietly reinforcing the level of thought and design intention behind the renovation. The second floor is a serene retreat and allows for elevated view of Lake Sylvan. The primary suite with soaring ceilings offers a generous window framing treetop views. The spa-inspired bath features a large glass-enclosed shower and a custom built-in dressing area, creating a private sanctuary that feels removed from the everyday. Two additional bedrooms, one with an en-suite bath, complete the upper level, offering flexibility for guests, work-from-home needs or extended stays. Outdoors, the grounds have been thoughtfully reimagined to evoke a cottage garden feel, providing a peaceful backdrop for morning coffee or evening strolls along the brick-lined street. The location is equally compelling, in a neighborhood known for its winding roads and timeless charm, just minutes from shopping, dining and cultural offerings of Park Avenue. Offering a lock-and-leave lifestyle, this home lives beautifully as a primary residence or as a second or third home and presents a compelling alternative to condominium or townhome living, where privacy, design and a desired Winter Park setting come together in one exceptional offering. There is potential for a third bedroom suite by converting the den/family room on the first floor as it is adjacent to a full bath.

Beautifully maintained and move-in ready, this desirable property within the sought-after Bahama Bay Resort presents a rare opportunity to own a turnkey residence with short-term rental potential, approximately 20 minutes from Walt Disney World and Central Florida's world-famous attractions. Unlike many resort condominiums, this fully furnished residence has been extensively updated and meticulously maintained, presenting an exceptional level of cleanliness, quality and overall condition rarely found in this market segment. Enhancements include a new HVAC system installed in May 2026, a new water heater (2021), recently painted interiors, new luxury vinyl plank flooring throughout and light contemporary furnishings that were recently replaced. With no carpet anywhere in the residence, the bright interior showcases neutral tones and a fresh, updated aesthetic designed for immediate enjoyment or rental readiness. In addition, the building received a new roof in February 2026, contributing additional long-term value for ownership. The open-concept layout creates a comfortable and relaxing atmosphere, while the updated and fully stocked kitchen features resurfaced cabinetry and newer stainless steel appliances (2021). The bath cabinetry has also been resurfaced, complementing the residence's cohesive updated aesthetic. The residence also features two screened patios overlooking mature trees and lush landscaping, creating inviting outdoor spaces to relax. Convenient ground-floor placement provides easy access in a building without an elevator, and the residence is close to one of the community's nearby resort-style pools. Bahama Bay Resort is a gated waterfront community spanning more than 70 acres of tropical landscaping and natural surroundings. Residents and guests enjoy an impressive collection of resort-style amenities, including multiple pools, spa, fitness center, clubhouse, restaurant, walking paths, beach area and access to Lake Davenport, all surrounded by tropical flowers, mature palm trees and serene green spaces. Owners may personally enjoy the residence during the year (maximum of 175 days annually), participate in the on-site rental management program or independently manage their own short-term rentals. A rare opportunity to own a meticulously maintained condominium ideal as a seasonal retreat or investment property.