Winter Park

Winter Park was the first centrally planned community in Florida; since its early beginnings as a 19th century resort destination, the city has always been a perfect place for both relaxation and recreation. With a number of wealthy and notable families residing in areas of Winter Park, this lovely city is generally considered to be one of the richest in Florida.


Located just northeast of Orlando, Winter Park is a place of parks, trails and lakes, of brick avenues, historic architecture and tree canopied streets. Nestled among the beautiful Winter Park Chain of Lakes (popular destinations for boating, fishing, and water-skiing enthusiasts), Winter Park is also known for its quaint shopping areas, its museums, and its popular festivals.

Winter Park's 30,000 residents are proud of their town's history, with several buildings over a century old. Few Central Florida communities can claim such a heritage. Community spirit is also evident in the variety of wonderful annual festivals, including the Bach Festival and the acclaimed Sidewalk Art Festival. Winter Park neighborhoods reflect this sense of community and history. The average price for a home here is $456,656 - this includes everything from sun-bleached haciendas in the $250K range, to exquisite Tudor style homes just under $1 million.


Winter Park Parks and Attractions


Parks, museums, bike trails, shopping - Winter Park has everything you could ever need, just minutes from home. Here we have just a small sampling of the attractions you'll find in the Winter Park area.

Winter Park Parks: Kraft Azalea Garden, Dinky Dock, Phelps Park, Howell Branch Preserve, Shady Park, Lake Island Park, Azalea Lane,Fleet Peeples Park, Cady Way

Winter Park Other Attractions: Park Avenue and many great restaurants.

Hot Winter Park Properties

32792 Zip Code
Welcome to a thriving business opportunity in the heart of Winter Park, Orlando – a prime location renowned for its upscale ambiance and vibrant community. Presenting an exceptional chance for savvy investors, this established barber shop promises not only a profitable venture but also a pathway to securing the coveted E2 visa. Situated in one of Orlando's greatest neighborhoods, this barber shop enjoys unparalleled visibility and foot traffic. Its strategic location within Winter Park ensures a steady stream of clientele comprising locals and tourists alike, drawn to the area's charm and sophistication. The business's solid financial performance, coupled with its strategic location in an affluent area, positions it as an ideal candidate for visa qualification. With the potential for job creation and contribution to the local economy, this venture aligns perfectly with the requirements for E2 visa approval. Key highlights of this barber shop business include: Prime Location Established Reputation: 5 years of operation. The owner just renew for another 5 years. Profitable Operation: Demonstrated financial performance, with steady revenue streams and growth potential. E2 Visa Eligibility: Meets the criteria for E2 visa approval, offering investors a clear pathway to residency and business ownership in the United States. Don't miss out on this exceptional opportunity to acquire a successful barber shop business in Winter Park, Orlando – an investment sure to yield both financial returns and the fulfillment of E2 visa aspirations. Act now to seize this lucrative venture and embark on a rewarding journey in the thriving Orlando market. Price: $215,000

Winter Park

4 Beds 4.5 Baths Kenilworth Shoes Sec 03 SubDv. 32792 Zip Code
Introducing a stunning, spacious four bedroom /four bathroom sanctuary boasting hardwood flooring in all main areas, complemented by designer porcelain tile in bathrooms and laundry. Custom by Native Homes. Expansive kitchen showcases beautiful exotic, neutral granite island, large breakfast room overlooking pool and tiled backsplash. There is a separate dining room on the first floor, as well as a second bedroom or private study with a bathroom and closet. Primary suite plus another bedroom suite conveniently located on first floor. Master suite is a dream! The dual sinks in the oversized bathroom offer convenience, while the 66 inch Jacuzzi brand stand alone soaking tub adds a touch of luxury. The sperate massive walk-in shower with dual showerheads perfect for spa-like experience and spacious walk-in closet completes the retreat. Bonus room, two bedrooms and two bathrooms up the wood stairs. All bedrooms showcase huge closets and custom organizers. Custom cabinetry and shoe storage, sitting bench in mudroom before entering garage. Home has been pressure washed and interiors all recently repainted. Tile and carpet professionally cleaned. Shows like a 2024 custom home! Enter your backyard sanctuary. Entertaining lanai including outdoor kitchen counters, fridge and big screen tv. Very private backyard. Green(real grass) space is perfect for birthday parties, trampolines, bounce houses and more. 2017-2018 added gorgeous saltwater pool with sun shelf surrounded by brick pavers. Fully fenced for pets and kids. Epitome of relaxation and comfort! Full house generator runs off gas. Tvs may convey some furniture available. This lot is 10-15% larger than most lots in the neighborhood. Long brick pavered driveway and two car garage with plenty of parking. You will love the very large walk-in storage off the bonus room for rugs, fixtures, décor, memorabilia. Most desirable Winter Park Schools! Walk to Brookshire Elementary. Close to shopping and restaurants along Park Avenue. Walk to the YMCA and Phelps Park. Golf and tennis neighborhood Racquet Club, Interlachen Country Club, and Winter Park 9 Golf Course.

425 Selkirk Drive, Winter Park

4 Beds 3 Baths Brookshire Heights 4th Add SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to Brookshire, the quintessential Winter Park neighborhood. This lovely home built in 1967 features 4 bedrooms and 3 full baths. The home has traditional spaces, formal living and dining rooms as well as a modern kitchen/family room combination. The exterior has distinctive curb appeal highlighted by its brick front, paver circular drive and beautiful established trees. The living area features a massive bay window and plenty of space for large furniture. The dining room features a Tiffany Style chandelier and has french doors to the sunroom. The kitchen has plenty of cabinet space, breakfast bar and window pass through to the sunroom. Enjoy casual living in the family room and stay connected to the cook. Add to this the amazing sunroom, open all the french doors for a wide open entertaining space. The owner’s bedroom suite occupies one side of the home and has room for a king size bed and a sitting area. The owner’s bath offers a single sink and walk in shower. On the other side of the living spaces are two bedrooms that share a jack and jill bath along with another bedroom that is served by a hall bath. The backyard is a private sanctuary, enjoy the brick patio and the luxurious landscaping. The yard is fenced and perfect for pets. Walk to Brookshire Elementary and Winter Park High School! The home is close to everything Winter Park has to offer. Don’t wait to see this great home! ROOF 2013 HAVC 2018 HOT WATER HEATER 2020, NEW ELECTRIC 2017, EXTERIOR PAINT 2018 The property has been PRE-INSPECTED for your buying confidence.

2358 Whitehall Drive, Winter Park

3 Beds 2 Baths Waterbridge SubDv. 32789 Zip Code
Welcome to your dream home in the coveted Waterbridge neighborhood! This stunning one-story pool home boasts everything you've been searching for and more including a 3-car garage. Situated on a spacious corner lot, this residence offers both elegance and comfort. Step inside to discover a welcoming ambiance, highlighted by a gathering living room featuring a double-sided gas fireplace, perfect for cozy evenings or entertaining guests. The dining room is conveniently located off the kitchen, complete with double built-in ovens and overlooking the inviting family room. A sunny Florida room extends off the family room, offering picturesque views of the lush backyard oasis and sparkling pool—a true haven for relaxation and enjoyment. Retreat to the primary suite, featuring a spacious walk-in closet for all your wardrobe needs. Two additional bedrooms, each boasting generous walk-in closets, ensure ample space for family or guests. Plantation shutters throughout add a touch of sophistication, while the large laundry room with cabinetry provides convenience and storage. Step outside to your own private paradise, where a gorgeous pool awaits, complete with a heated spa, sun shelf, and seating bench—all within the confines of a large privacy fenced backyard. Waterbridge residents enjoy access to community amenities including a park and tennis courts, fostering a sense of community and recreation. Conveniently located near shopping, restaurants, and minutes from Park Avenue, this home offers easy access to all the best Winter Park has to offer. Plus, with sought-after Winter Park schools just a stone's throw away, you'll enjoy peace of mind knowing your family is in a top-notch educational environment.

1203 Germaine Drive, Winter Park

3 Beds 2 Baths Lawndale SubDv. 32789 Zip Code
A Testament to Timeless Elegance: Your Dream Home Awaits in Winter Park. Step into a piece of history with this beautifully restored 1927 Florida Bungalow, situated in the cherished and serene neighborhood of Orwin Manor. This exquisite home seamlessly blends the charm of its original architecture with modern luxury and conveniences, offering a unique sanctuary for those who value both tradition and contemporary living. As you enter through the inviting foyer, you are welcomed by new tile flooring and vertical shiplap walls, creating an atmosphere of fresh sophistication. Custom transitions draw you into a living room where the warmth of original hardwood floors meets the convenience of smart lighting and a cozy fireplace, perfect for both lively gatherings and quiet evenings at home. The dining room, capable of hosting eight, dazzles under a stylish Serena and Lilly chandelier, setting the scene for memorable dinners. Adjacent lies the heart of the home: a chef’s paradise kitchen. Renovated in 2020, this culinary haven boasts striking Calacatta countertops, a grand island, top-of-the-line Samsung appliances, and chic West Elm lighting. The adjoining eat-in area offers a relaxed dining experience and opens to a beautifully paved backyard, ideal for alfresco dining and entertainment. Accommodation is generous and refined, featuring a lovely master suite with dual closets and a sleek bathroom equipped with matte finishes. Additional rooms include a versatile rec room and a guest bedroom, each meticulously designed for comfort and style. The home also includes a secluded attic for extra storage. Special attention has been given to both aesthetics and functionality, from smart exterior lighting and a durable new vinyl fence to minimal maintenance landscaping designed to flourish in Florida's climate. The updated HVAC system features a Carrier unit and smart thermostat, ensuring year-round comfort. This home is not just a place to live but a piece of history to cherish. Original woodwork, including baseboards and casings, pay homage to the home’s heritage, while the curated paint choices and Trex exterior staircases ensure its beauty endures. Located just minutes from Park Ave, College Park, and major thoroughfares, this home offers an unparalleled blend of tranquility, community, and convenience. Do not miss the chance to own a legacy of luxury in Orwin Man. Every corner of this home tells a story, and every detail invites you to make it your own. Welcome to your dream home, where history and modernity live in perfect harmony.

1707 Harmon Avenue, Winter Park

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