Homes for Sale in Winter Park

Located in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a luxurious Mediterranean-inspired design with so many modern upgrades, all just steps from Park Avenue’s shops, Winter Park Village, and Whole Foods Market. This stunning home, set on a prime lot adjacent to the Winter Park Golf Course, provides the perfect balance of privacy and convenience. Upon entering through custom double front doors, you’re greeted by an impressive foyer with soaring ceilings and a striking wall-mounted water fountain. The luxurious primary suite is privately situated on one side of the home and features an elegant bath, dual sinks, exquisite shower, and customized his-and-her walk-in closets. A second bedroom or office/study (with a private ensuite bath and walk-in closet) is also on the first floor across from the primary bedroom. This flexible space includes a custom walnut Murphy bed, allowing for dual use as a guest room or office.Continue into the open-concept home as it seamlessly flows from the living room to the dining room. A massive double-sided gas fireplace serves as a centerpiece between the dining room and family room areas. The gourmet kitchen is a chef's dream, outfitted with Sub-Zero Wolf appliances, a reverse osmosis water system, and a large island with bar-top seating that joins the family room. Oversized windows allow natural light to flood these spaces. Sliding doors open to an expansive 35-foot covered lanai, ideal for entertaining or al fresco dining. The lanai features a summer kitchen (with Egg grill) and retractable screens, leading out to a private saltwater pool and spa, which can be heated quickly through a mobile app. A fenced yard includes a small, turfed area, perfect for pets or play. A gate leads right out to the adjacent golf course. Upstairs, you’ll find a private third bedroom with an ensuite bath, along with a versatile multi-use space that can be used as a gym, theater room, or additional living area. For added privacy, a separate fourth bedroom suite is located at the rear of the home. This apartment-like suite includes a bedroom, private bath, living area with small refrigerator and sink along with a large second-story private terrace with sweeping views of the golf course. This living area features its own outside entry and security system, offering complete independence from the rest of the home and a door within that can be locked to separate, if desired. Additional features include a whole-home Briggs & Stratton generator, water softener system, tankless water heaters, two newer Trane 16 seer HVAC systems, a security system with multiple cameras, and exterior painting with a lifetime transferable warranty. With its unparalleled location and exceptional design, 1010 N Pennsylvania Ave is a rare opportunity to own a home that combines luxury living with modern convenience. Don’t miss your chance to make this exceptional property your next home! Feel free to request an upgrades and features sheet outlining all the wonderful aspects of this home! Seller has recent inspection report and home appraisal.

Under contract-accepting backup offers. EXQUISITE RESIDENCE IN THE VIAS! This custom-designed home features 4 bedrooms, 3-full baths and sophisticated touches of elegance throughout. The modern design philosophy blurs the lines between the interior and exterior spaces of the home and creates a cohesive feel that’s open and airy. Built with SMART home technology, the home is outfitted for thermal efficiency and uses a LUTRON lighting system, central vac system, as well as a home audio and security system. High-end interior finishes include white oak floors, La Cantina Panoramic doors, a chef’s kitchen with SUBZERO and WOLF appliances, and a luxurious primary bedroom with spa en suite, complete with an oversized jetted tub. Motorized, retractable screens on the lanai lift to reveal a magnificent resort-inspired backyard. Summer kitchen, heated saltwater pool, a 9-hole mini golf course, and perfectly manicured landscaping by Keller Outdoors all blend to create the perfect private oasis. Located within one of Winter Park’s most desirable neighborhoods, the Vias offer picturesque brick streets for walking and proximity to the Racquet Club and Chain of Lakes.

This stunning custom home, completed in 2021, is located among the highly desirable “tree streets” in the heart of Winter Park, and was custom-built by M. Lahr Homes, showcasing exquisite craftsmanship and thoughtful design. With high-end finishes and custom details hand-selected by the owners, this home is sure to check every box. Designed with both luxury and functionality in mind, the home is equipped with natural gas for the cooktop, water heater, pool heater, grill, and fireplaces, while smart technology enhances modern living with app-controlled kitchen appliances, thermostats, irrigation, pool equipment, and garage doors. Neutral wood flooring, Restoration Hardware lighting, and custom electronic window treatments by The Shade Store add to the home’s understated sophistication. Additional highlights include copper gutters, level 5 finished walls, designer wall coverings, and custom storage throughout. Offering nearly 4,000 sq. ft. of organic, modern design, the open floorplan blends functionality with timeless elegance. The expansive living and dining areas flow seamlessly into the kitchen, which features Thermador smart appliances, quartz countertops, and a massive island with a stylish open-shelving detail. A hidden walk-in pantry behind the kitchen adds a bar fridge, microwave, and abundant prep space. The downstairs Primary Suite is a serene retreat with pool views through a picture window, a spa-like bathroom with a soaking tub and glass-enclosed shower, and an oversized, custom walk-in closet. A second main-level suite with a full bath and walk-in closet is currently used as an office overlooking the front lawn. Upstairs, a spacious bonus room/living area is surrounded by (3) additional bedrooms, each with walk-in closets, and (2) full bathrooms. The outdoor living space is an entertainer’s dream. The 8 ft sliding glass doors, with 2 ft. transom windows above, open to a covered lanai with motorized screens, a gas grill, and a fireplace for year-round enjoyment. Beyond the lanai is a meticulously landscaped backyard, fully fenced for privacy, with a heated saltwater pool wrapped in artfully laid out artificial turf and travertine pavers. Storage is abundant, with a custom-outfitted mudroom and laundry room, an oversized 2-car garage featuring storage shelves, and custom designed closets throughout. Ideally located, this home offers easy access to downtown Winter Park, Park Avenue, the YMCA, Aloma shopping center, and Whole Foods.

Under contract-accepting backup offers. Prestigious Windsong community-Discover luxury living at its finest in this exquisite 5-bedroom, 5 full and 2 half-bathroom estate built by renowned Hal George (Parkland Homes). Boasting a traditional, red brick exterior and surrounded by a private 12 ft hedge, this meticulously maintained, light-filled home offers unparalleled privacy and modern elegance. Upon entry, you're greeted by a grand foyer, setting the tone for the home's impeccable craftsmanship and attention to detail. The main level features a well-appointed office and a spacious primary bedroom retreat that opens gracefully to the pool lanai, offering a seamless indoor-outdoor lifestyle. Beautiful primary bath features travertine marble, a spacious soaking tub, and a large shower, epitomizing luxury and relaxation. The heart of the home revolves around an open yet distinct layout, perfect for daily living and entertaining. The family, dining, and living rooms flow effortlessly, enhanced by new LED lighting and a gas fireplace for added ambiance. The gourmet kitchen is a chef's dream, showcasing granite countertops, pale oak cabinetry, and top-of-the-line appliances including a Wolf gas range, Subzero refrigerator, Bosch dishwasher, and Perrin and Rowe faucets; a window wall behind the dining banquette floods the kitchen with natural light and looks out onto the pool area and private backyard. Dual pantries provide ample storage space. Upstairs, a separate staircase on one side of the house leads to the fifth bedroom/bonus room with walk-in closet and bathroom, ideal for guests or a private retreat. Upstairs from the main living area are three bedrooms with en-suite bathrooms and a fourth “loft” room, perfect for a library, studio or playroom. Outdoors, indulge in resort-style amenities including a recently resurfaced, heated saltwater pool with a gas-heated spa, fiberoptic light tower, and Jandy Digital Assistant controller. The pool deck is at the center of a private, beautifully landscaped, backyard “room” surrounded by walls of green hedges, perfect for early morning coffee and birdsong or a glass of wine in the evening as the sun sets, washing the pool with color. The 2022 designer summer kitchen boasts marble countertops and a stainless steel Wolf gas grill. A pool bathroom adds convenience for guests. A mudroom and laundry area offer practicality and organization. Additional features include completely refinished wood floors throughout, a new security system with video cameras, a central vacuum, three AC units installed between 2015-2018, a whole house dehumidifier installed in 2023, and two hot water heaters. Outside, enjoy immaculate landscaping, a long driveway leading to a three-car garage with Tesla charging station, and serene touches like a Buddha garden. Located in the highly desirable Windsong, residents benefit from exclusive access to the Winter Park Chain of Lakes, pools and water park area for entertaining, and playgrounds. Minutes away from Park Avenue shopping and restaurants, Baldwin Park, parks, playgrounds, and excellent public schools including Brookshire Elementary, Glenridge Middle, and Winter Park High School. Don’t miss this rare opportunity to own a masterpiece in one of Winter Park’s most coveted neighborhoods. Contact us today to schedule your private tour and experience luxury living at its finest.

Under contract-accepting backup offers. Welcome to this renovated traditional home, ideally situated on a corner lot in one of the most desirable neighborhoods in all of Central Florida. This charming, white-washed brick exterior Winter Park home offers everything a family could need. This two-story, 3 car garage, residence showcases the finest upgrades and provides an unparalleled living experience. As you enter the front door, the first floor welcomes you with a formal dining room that provides the perfect setting for entertaining guests with a custom-built wine display at arm's reach. Conversely, you also have an office that doubles as a sitting room with an exterior door leading to a charming cigar porch. As you continue down the hall, you enter an elegant living room featuring a gas fireplace, custom built-ins, and accordion stacking doors that open to a picturesque outdoor living area. The large chef's kitchen is equipped with a gas cooktop, farm sink, stainless appliances, quartz countertops, a butler's pantry, lots of cabinet storage, and a breakfast nook overlooking the pool. Opposite the kitchen, you have the first-floor primary bedroom with custom built-in closets and a large bathroom. Venture upstairs through one of the two staircases to an additional four bedrooms, three full bathrooms, and a bonus/theatre room, including two oversized storage closets that can be multifunctional. This is an excellent house for entertaining and enjoying the Florida sunshine with the expansive backyard, where you'll find a large pool, a covered sitting area, and a fully equipped summer kitchen with a grill, Green Egg, sink, and fridge. Located in the premier neighborhood of Winter Park, this home is minutes from Park Avenue, with numerous top restaurants, shops, and yearly events to enjoy. You can also easily access major roadways, top golf clubs, and tennis facilities such as the Winter Park Racquet Club and Interlachen Golf and Country Club. This home is zoned for highly rated Winter Park schools, including Dommerich Elementary, Maitland Middle, and Winter Park High School. This exquisite residence epitomizes elegant living in a prime location. Don't miss the opportunity to make this stunning home your own.

Seller Financing available. Located in the heart of Winter Park, this exquisitely redesigned custom home blends transitional elegance with Mediterranean architectural nuances. Designed by esteemed architect Gary Hancock and renewed by a longtime Winter Park designer. Every inch of this residence showcases unparalleled attention to detail. Set on a cobblestone street, this home offers a blend of community and privacy, making it a rare gem in one of the most desirable neighborhoods. This residence sits within a triangle of walkable lakefronts, Lake Sue, Lake Chelton, and Lake Virginia in the beautiful setting of Rollins College. A fusion of contemporary finishes is juxtaposed with Georgian wood windows and wrought iron railings lining the grand staircase. A circular foyer welcomes you with French doors leading to a private office/library. Chic living and formal dining rooms feature travertine marble floors, and smooth museum-quality walls all complemented by designer finishes. Arched hallways beckon you to the heart of the home and its open-concept kitchen and breathtaking family room, featuring wood beam ceiling, inlaid wood and marble floors, a stone fireplace, and a unique chandelier with Agate disks that sparkle above. A chef’s kitchen is equipped with high-end Wolf & Sub-Zero appliances, 42-inch custom wood cabinetry, and exquisite granite counters further enhanced by the subtle glow of alabaster pendant lighting & alabaster backlit backsplash. The center island, casual bar seating, and large informal dining area allow for any size gathering. The great room seamlessly extends into the outdoor spaces, offering privacy and serenity. Unobstructed views through multiple French doors that open to a courtyard filled with light. The veranda features wood ceilings, a stone gas fireplace & breezy ramada porches with lantern lights that reflect in the pool. The home’s design invites the outside in. The first-floor primary suite offers a secluded oasis, featuring doors that open onto the lanai, a gracious seating area designed for tranquility at day's end. The luxurious primary bath displays exquisite mother-of-pearl inlays within the flooring and walk-in shower, complemented by bespoke dual vanity and stunning light fixtures. A spacious closet offers endless room for an extensive wardrobe and room for an additional office, a Peloton, a fitness sanctuary, or a cozy nook for a newborn to nap. This expansive 4,692 square-foot home boasts versatile living with various entertainment opportunities. The upper level continues to impress with new wood flooring, three gracious en-suite bedrooms with walk-in closets, separated by a Juliet balcony with breathtaking views, an alternative primary suite, and an oversized family area. Additional highlights are an open-concept layout achieved by removing walls, smooth wall finishes, fresh interior and exterior paint, and a striking barrel tile roof. Plantation shutters, a walk-in pantry, updated baths, lighting, fixtures, and hardware, alongside solid doors, enhance the home’s appeal. Professional landscaping, artificial turf in the backyard for ease of maintenance, and two staircases, one stair from the laundry area for convenient housekeeping, and another front staircase. A short distance from Park Ave, Mills 50, Corrine Dr, downtown, Advent Health & more, perfectly situated for enjoying the best of Winter Park while offering an unmatched level of luxury and comfort. Zoned for Audubon K-8 & WP High School.

One or more photo(s) has been virtually staged. Luxury lock & leave living from 147 S Interlachen Ave. This penthouse is a four-bedroom, 4.5 bath two-story condominium home in the heart of downtown Winter Park overlooking one of the most prestigious tree-lined streets in the city. The floor plan is great for entertaining with a two-story great room with a spectacular Chihuly chandelier as the centerpiece, along with an all-glass circular staircase. A wall of glass has access to the open balcony overlooking Interlachen Avenue. The spacious primary suite offers large en-suite bath and a double walk-in closet. The remaining three bedrooms, all with ensuite baths plus a dedicated office/den is on the second floor which can also be accessed by the private in-unit elevator. 147 Interlachen is boutique condominium complex with a gorgeous center courtyard with fountain, under-building secured parking and a lovely community pool. Steps to Park Avenue fine dining and restaurants, the Winter Park Farmer's Market and Central Park.

Welcome to the sophistication and contemporary masterpiece developed by DaVinci Development. This exceptional residence features five spacious bedrooms, six and a half bathrooms, and 4,500 square feet of meticulously designed living space. Nestled within the exclusive enclave of Winter Park, this new construction opportunity redefines opulent living. The architectural marvel boasts a unique contemporary design, seamlessly integrating form and function. From the moment you arrive, the striking facade captivates with sleek lines and 10 foot ceilings on both levels of the home. Inside, natural light floods the open-concept living spaces, creating an inviting atmosphere that is both luxurious and welcoming. Entertain with ease in the gourmet kitchen, equipped with top-of-the-line appliances, Sub Zero, Wolf and Miele, custom cabinetry, a spacious island, and a wine cooler. The adjacent living and dining areas provide the perfect backdrop for gatherings, both large and small. The lavish primary suite, located on the first level, offers a private sanctuary of comfort and style. Indulge in the spa-like en-suite bath, featuring a soaking tub, oversized shower with dual shower rain shower heads , and dual vanities, creating the ultimate haven for relaxation. Escape to your outdoor oasis directly from the primary suite. An additional bedroom on the first level adds convenience, featuring a walk in closet and ensuite bathroom and currently staged as the home office. Retreat to the upper level to find a spacious loft that features a wrap around balcony, this space is ideal for relaxation and entertainment. Adjacent to the loft are three generously sized bedrooms, each offering a unique blend of comfort and style. Whether for family members, guests, or a home office, these bedrooms provide versatile spaces that adapt to your lifestyle needs. Outside, discover your personal paradise that sits on the largest lot on the street, featuring a sparkling pool, expansive patio, and outdoor kitchen, perfect for alfresco dining and year-round entertaining thanks to the retractable screens enclosing the lanai when needed. Additional features include a three-car garage with an EV car connection, leading to a mudroom and laundry area with ample storage, ensuring every aspect of this residence exceeds the expectations of the most discerning homeowner. Nestled in a highly sought-after location, this residence enjoys an enviable address surrounded by top-rated schools and is moments from renowned attractions such as Park Avenue, that promises unique shopping and upscale dining. Experience the pinnacle of luxury living with this exceptional new construction home.
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This exquisite, custom-designed residence blends impeccable architectural details with unparalleled craftsmanship. With Pella windows and natural stone accents throughout, this home showcases a Poggenpohl gourmet kitchen featuring Wolf and Sub-Zero appliances, cascading countertops, and natural hardwood floors. A unique double primary suite layout offers two luxurious primary bedrooms, each with its own expansive executive powder room. The upper suite opens onto a private outdoor terrace, perfect for enjoying views of the lush outdoor oasis, which includes a heated luxury pool and spa, completed by an outdoor summer kitchen featuring Miele appliances. This home boasts two-story concrete-filled walls, steel joists, and composite steel decking, with a waterproof concrete roof. A stunning floating staircase leads to the second level, which includes the second primary suite with a spacious executive powder room, plus two additional bedrooms and an expansive custom walk-in closet. The interiors are bathed in natural light, compliments of the soaring 20' ceilings and an open, airy layout. Handcrafted luxury elements, including a bespoke entry door and Clopay modern garage doors, make a bold first impression. Additional highlights include elegant lighting, stunning automated window coverings, innovative hidden appliances, pristine landscaping and so much more. This masterpiece offers beauty and style with full functionality and the very best of everything. Just steps from the Vias, K-12 educational zoning all Winter Park. Truly photos and words do not begin to describe this Architectural Brilliance. Come out and explore this gem where you will be greeted by Astro the Robot.

A unique opportunity to own a direct waterfront condominium in downtown Winter Park on Lake Virginia with the finest views, in exclusive Perle Du Lac. This one owner unit is wrapped on a spacious corner, flanked with windows and drenched in light, and exudes understated luxury. This three-bedroom three-bath split bedroom plan condominium boasts nearly 2,700 square feet of open spaces for modern function. A marble floor foyer and warm wood floors and volume ceilings invite you into a neutral palette and timeless finishes. A European SieMatic luxury kitchen with beautifully crafted solid wood cabinetry, stainless appliances and center island with solid Corian counters, which open to dining space with wine storage and dry bar, for ease of entertainment. Living spaces overlook the lake and seamlessly blend into balcony with second-floor unobstructed views of Lake Virginia overlooking the Windsong preserve and a long view to soak in the Chain of Lakes sunsets. Primary bedroom is lakefront with doors to patio and large custom European closet cabinetry, and primary suite is appointed in Italian Carrera marble add to the elegance of the finishes. Unit includes a deeded boat slip to enjoy lake life through the Venetian-style canals connecting five lakes. Other highlights of the community include secure entrance with double gates for convenience, secure buildings, community pool, underground parking with elevator to units, storage, greenspace and ample parking. Walk to Park Avenue where restaurants and shopping are abundant, art festivals, community events and more. Indoor laundry, enhanced lighting package, custom window treatments add to the list of features. Perle Du Lac neighbors Rollins College and president of Rollins home, there is not a more breathtaking setting than Perle Du Lac. Fully gated with underground parking and community pool making everyday life simple with everything within arm’s reach. A rare opportunity for the most discerning buyer.

Under contract-accepting backup offers. Welcome to 455 N Interlachen in Winter Park, Florida 32789, where timeless elegance meets modern comfort. This stunning home underwent a complete remodel in 2009, ensuring every detail is curated to perfection. As you step inside, you're greeted by a grand foyer that sets the tone for the luxurious living spaces beyond. The main level boasts a harmonious flow between the living room, dining area, and kitchen, creating an inviting atmosphere for gatherings and relaxation. The chef-inspired kitchen is a true masterpiece, featuring top-of-the-line appliances, custom cabinetry, and an expansive island perfect for culinary adventures or casual dining. With high-end finishes and thoughtful design elements, this kitchen is as beautiful as it is functional. A highlight of the home is the primary suite conveniently located on the first floor. Offering a peaceful retreat from the hustle and bustle of everyday life, the primary suite features a spa-like ensuite bathroom and ample closet space, providing the ultimate in relaxation and privacy. Upstairs, you'll find additional bedrooms, each offering comfort and style, making them perfect for family members, guests, or a home office. Every room is bathed in natural light, creating an inviting atmosphere throughout. Outside, the meticulously landscaped yard offers a private oasis for outdoor enjoyment. Whether you're hosting a barbecue with friends or simply unwinding after a long day, the outdoor space provides endless opportunities for relaxation and entertainment. Located in the desirable downtown Winter Park area, this home offers easy access to shopping, dining, parks, and more, allowing you to experience the best of urban living. Don't miss your chance to make this exquisite property your own and enjoy the epitome of Florida luxury living.

One or more photo(s) has been virtually staged. Newly Renovated Partially Furnished Home in the Beautiful Via’s of Winter Park! Designed and built by Groninger Custom Homes. Privately located on a large wrap around corner lot. It is meticulously maintained with eye-catching curb appeal with mature magnolia trees and beautiful landscaping with newly installed lighting to illuminate at night. This stunning 6 bedroom and 3.5 bath home boasts over 3,554 SF of comfortable living space and offers high ceilings, arched entries, and luxury vinyl flooring throughout the main floor. Upon entering the expansive foyer, to the right is a den/office with pocket doors for privacy. On the left is the open dining room that overlooks the two-story living room. Triple set of French doors lead off the living and family rooms and open to a covered lanai and screened-in pool with a waterfall. Living room showcases a marble encased wood burning fireplace with built-in bookshelves. The Kitchen has an open floor plan which overlooks the family room. It has an eat-in area surrounded by a bay window. It boasts with new high end quartzite countertops and backsplash along with a waterfall design on the center island. The prime bedroom is privately located on the main level tucked in the back corner of the home. This luxurious large bedroom overlooks the pool and covered lanai which are accessible through the French doors in the bedroom. The prime bathroom has a separate walk-in shower and a huge, jetted tub. It includes a huge walk-in closet and two vanities. Across the Prime bedroom is an additional bedroom and full bathroom on the main floor which also connects to the pool area. The pool has a safety fence installed. There are 4 other bedrooms on the second floor. The 2nd story hallway has built-in shelves on one side and a balcony overlooking the 2-story living room. Beyond the screened pool area is a gated private backyard with lush landscaping lined with 10-foot foliage. The backyard gate leads to the newly added side yard with a marble tiled patio for your larger gatherings. It’s lined with Podocarpus’s which can be fenced in for more privacy. This home was recently renovated to a more modern look with new paint, flooring, all new updated fixtures and much, much more…It is a must see! This home is being sold with all the furniture but can be removed if Buyer does not want it. Some pictures are Virtually Staged.