Winter Park Real Estate

Winter Park Real Estate

Nestled in the sunshine state of Florida, Winter Park is a charming city known for its picturesque parks, upscale shopping, and cultural experiences. Located in Orange County, Winter Park offers a mix of historic architecture, tree-lined brick streets, and a thriving arts scene.

One of the city's highlights is Park Avenue, a popular shopping district featuring boutique stores, sidewalk cafes, and art galleries. Residents and visitors alike can enjoy leisurely strolls, gourmet dining, and unique finds in this vibrant area.

Nature lovers will appreciate the city's numerous parks and lakes, providing opportunities for outdoor activities such as boating, picnicking, and scenic walks. The annual Winter Park Sidewalk Art Festival attracts artists and art enthusiasts from around the country, showcasing a wide range of creative talents.

With top-rated schools, a strong sense of community, and proximity to Orlando's attractions, Winter Park offers a high quality of life for its residents. Whether you're exploring the Morse Museum's collection of Tiffany glass or enjoying a boat tour on the Winter Park Chain of Lakes, this city has something for everyone to enjoy.

Newest Listings in Winter Park

$760,000
3 Beds 2 Baths Shores Lake Killarney Sec 02 SubDv. 32789 Zip Code
Experience the epitome of luxury living in this stunning 3-bedroom, 2-bathroom home nestled in the prestigious Shores of Lake Killarney neighborhood in Winter Park. Boasting a prime corner lot with manicured hedges and landscaping, this upgraded ranch-style home is move-in ready and offers a plethora of desirable features. Step inside to discover a spacious 2270 square feet of living space flooded with natural light. The kitchen is a chef's dream, complete with hickory wood cabinetry, quartz countertops, and stainless steel appliances. The primary suite is a true retreat, featuring a cozy wood-burning fireplace, a sitting area, and a massive walk-in closet. The primary bath is equally impressive, with a walk-in shower and a luxurious garden tub with jets. Entertain guests effortlessly in the screened-in pool area or on the patio overlooking the pool. For added privacy, the property is surrounded by a tall block wall. Additionally, enjoy deeded lake access to Lake Killarney, perfect for boating, skiing, paddleboarding, or docking at Winter Park's finest restaurants. Conveniently located just minutes from I-4, Park Ave, Rollins College, and Winter Park Village, this home offers easy access to first-class shopping, restaurants, and world-class museums. With no HOA restrictions, this is a rare opportunity to own a piece of paradise in one of Winter Park's most sought-after neighborhoods. Don't miss out on this exceptional property!

260 Rippling Lane, Winter Park

$7,250,000
4 Beds 4.5 Baths Winter Park SubDv. 32789 Zip Code
**500 N. INTERLACHEN AVENUE, WINTER PARK, FL 32789** INCREDIBLE OPPORTUNITY – HISTORIC LAKEFRONT ESTATE ON THE SHORES OF LAKE OSCEOLA – ONE BLOCK FROM PARK AVENUE! Absolutely stunning and timeless, this historically designated home sits on an oversized 0.74 acre lot and features a private boathouse with approximately 50’ of waterfrontage. Originally built in 1934 the 4 bedroom, 4.5 bath home embraces Spanish-revival style through its elegant use of sun-kissed terracotta floors, arched entries, ironwork details, dark wood accents, and imported chandeliers. Formal living spaces are complimented by hand-painted ceilings, custom moldings, marble fireplaces, and handcrafted built-ins. The gourmet kitchen features professional grade appliances, custom cabinetry, emerald green granite countertops, and a large island. Laid out extremely well, the interior floorplan offers a first-floor primary bedroom with walkouts to the terrace and an en suite bath with dressing room. Upstairs are three guest rooms, each with a private bath, and generously sized closets. Unlike many homes in the area, this residence offers a lower level, or finished basement, that showcases a several hundred bottle wine room and additional storage area. Inspired by its Spanish-Mediterranean roots the home relies on several outdoor courtyards, patios, terraces, and balconies to extend living space outdoors, creating the ideal setting for large gatherings with friends and family. With it’s resort-like setting, this home provides year-round opportunity to enjoy the Florida weather along with a private salt-water pool and expansive rolling green space down to the shores of Lake Osceola. Located in charming Winter Park, FL, this magnificent estate is just a short walk to award-winning dining and boutique shops as well as the Alfond Inn, Rollins College, and many other nearby historic sites and attractions.

500 N Interlachen Avenue, Winter Park

$299,900
2 Beds 2 Baths Winter Park Pines Patio Homes SubDv. 32792 Zip Code
MOVE RIGHT IN! This well maintained 1233sf, 2 BEDROOM/2 BATH VILLA on a CORNER LOT in the beautiful WINTER PARK PINES neighborhood is ready for a new owner! Centrally located, this GOLF COURSE COMMUNITY boasts gorgeous OAK LINED STREETS and is just minutes to UCF, downtown Orlando, the Airport, Cady Way Park, Baldwin Park and the VA Hospital, Full Sail University and so much more…definitely a COMMUTER’S DELIGHT! The KITCHEN has a CLOSET PANTRY, SOLID MAPLE CABINETRY, a PASS THRU TO THE GREAT ROOM, sliders to an OUTDOOR COURTYARD and includes ALL APPLIANCES, even the WASHER & DRYER. A CATHEDRAL CEILING with WOOD BEAMS and a rustic BRICK and WOOD FIREPLACE with a hearth enhance the spacious GREAT ROOM. Oversized sliders in the Great Room lead to a 30x12 PATIO enclosed with a WOOD FENCE which is the perfect spot for private relaxation with your favorite beverage at the end of the day. DOUBLE DOORS lead to the16x12 MASTER SUITE which has a CATHEDRAL CEILING and a WALK-IN CLOSET. The EN SUITE MASTER BATH has SOLID WOOD CABINETRY and a SOLID SURFACE VANITY area which is separate from the shower and toilet area. Additional INTERIOR FEATURES of this home include a NEW HVAC SYSTEM (currently in the permitting stage and will be installed during MAY 2024), TILE and LAMINATE FLOORING throughout, WOOD FAUX BLINDS in the bedrooms, CEILING FANS in all above grade rooms and an abundance of NATURAL LIGHT. EXTERIOR FEATURES include a TILE ROOF, GUTTERS and DOWNSPOUTS, a SINGLE CAR GARAGE with PULL DOWN ATTIC ACCESS, BUILT IN SHELVING and a WORKSHOP AREA. The HOA FEE is LOW and INCLUDES FRONT & REAR LAWN MAINTENANCE (mowing and edging) and IRRIGATION. Don’t miss your opportunity to own this lovely home…Call us today for a private showing!!

603 Warrenton Road, Winter Park

$2,795,000
5 Beds 6.5 Baths Winter Park Village SubDv. 32789 Zip Code
Welcome to the sophistication and contemporary masterpiece by Parkland Homes. 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.

2412 Chantilly Avenue, Winter Park

$850,000
4 Beds 3 Baths Kenilworth Shores Sec 03 SubDv. 32792 Zip Code
Welcome to this beautifully cared for family home, 4 bedrooms, 3 full baths, plus an office. Located in the highly desirable Kenilworth Shores neighborhood in the heart of Winter Park. The inviting entry with a cozy front porch and a brick paver walkway and driveway are bordered by colorful garden beds containing a lovely variety of shapes, colors, and textures of foliage and flowers. A seamlessly open floor plan connects the living room, dining room and kitchen area, surrounded by large windows and French doors offering natural light and scenery. The fabulous expansive kitchen has an abundance of cabinets, drawers, and counter space, a floor to ceiling cabinet pantry with pull out shelves, 2 separate sinks, pretty granite countertop, stainless steel appliances and a breakfast bar that seats 8. Huge master bedroom has plenty of room for a sitting area, vaulted ceiling and 2 walk-in closets. The master bath offers a dual sink vanity and a spacious walk-in shower with dual shower heads. The master suite has its own 2024 HVAC. Additional features – re-pipe 2024, roof 2012, updated windows, beautiful engineered wood floors, newer carpet, recessed lighting, and no shortage of closets - plenty of storage, jack and jill bath between bedrooms 2 & 3, a new water heater, added hurricane straps, and a freshly painted exterior. Mature towering trees shade the backyard and the 17 x 13 open brick paver patio from summer heat. Pathways wind through an array of native plants and flowers in this wildly naturalistic style garden. Walking distance to the Phillips Crosby Wellness Center and Ward Park – one of the most diverse parks in the city, from the athletic facilities to the playground to the walking and biking trails. A short drive or bike ride to Rollins College and to shops and restaurants on Park Ave. Don’t miss out on this gem, book your showing appointment today.

2013 Kimbrace Place, Winter Park

$2,150,000
3 Beds 3.5 Baths Virginia & Morse Brownstones SubDv. 32789 Zip Code
Welcome to Luxury Townhome Living in Winter Park. Indulge in sophisticated urban living with this meticulously designed 3-bedroom, 3.5-bathroom townhome by renowned architect Phil Kean. Spanning over 3,000 square feet, this residence seamlessly blends privacy, convenience, and luxury. Every detail has been thoughtfully curated, from the custom wood cabinetry to the exquisite Carrara marble primary bath. Upon entering, you'll find a spacious office and a bedroom with an en-suite bath on the ground floor. The private elevator provides effortless access to all three stories, as well as the rooftop terrace. The second floor unveils an open-concept living area, perfect for entertaining, featuring a gourmet kitchen equipped with top-of-the-line Wolf and Sub-Zero appliances, a 36" gas range, quartz countertops, and a dry bar with wine refrigerator. The third-floor primary suite is a sanctuary with two walk-in closets, a private balcony, and a spa-like bathroom featuring a soaking tub within a large glass and marble shower. An additional bedroom on this level also includes a private balcony and an en-suite bath, along with a walk-in closet. Outdoor living reaches new heights on the rooftop terrace, complete with an outdoor television, ideal for gatherings and enjoying breathtaking Florida sunsets. The home is adorned with custom built-ins, designer fixtures, California closets, and a Control 4 security system for peace of mind. Enjoy the ease of the lock-and-leave lifestyle and explore all Winter Park has to offer, just steps from fine dining, boutique shops on Park Avenue, Hannibal Square, and the Winter Park Farmers' Market. This residence is the epitome of sophisticated living, where every detail embodies elegance and comfort.

419 W Morse Boulevard, Winter Park

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