Winter Park's #1 MLS Search

Winter Park Real Estate – including MLS Listings, Homes, Condos, Townhomes, Land, Investment Property, and Foreclosures for Sale Search

Updated every 5 minutes with the latest real estate for sale in Winter Park - including MLS listings, homes, condos, townhomes, investment property, and land - as posted by Winter Park real estate agents and brokers - over 30% more listings than Zillow, Realtor, Trulia, and Redfin.

Get Signed Up Now to receive new listings, price changes, and recent sales prices - with the ability to get daily, weekly, bi weekly, or monthly email updates.    

By creating your FREE account you can:

  • Get New Property Email Alerts
  • Price Change Alerts
  • Detailed Property Info 
  • Virtual Pictures
  • Track Recent Active, Pending, and Solds

Get Signed Up Now and get the latest Winter Park tax and HUD foreclosures, REO properties, bank owned homes, and short sales being offered at HUGE price reductions and significantly lower than retail value.   

Winter Park Information and Highlights

Winter Park is a suburban city in Orange County, Florida, and is part of the Orlando-Kissimmee-Sanford Florida Metropolitan Statistical Area. Some notable locations in the city are Rollins College, Full Sail University, and the Charles Hosmer Morse Museum of American Art, which is home to the world’s most comprehensive collection of Tiffany glass. Winter Park features open park space, affluent neighborhoods, golf courses and a popular shopping district along Park Avenue. It was originally founded as a resort community by northern business magnates in the late 19th century. As it stands today, Winter Park is a beautiful city with convenient locations to some of Florida’s biggest attractions, as well as a slew of their own. For college students and those looking to raise families in a beautiful Floridian suburban city, Winter Park has grown in popularity since its development and is highly praised by both visitors and residents alike to this very day. It continues to grow in popularity and in visitation each year.

Weather

Winter Park experiences the typical Florida experience with high heats and high humidity stretching throughout the year. Very rarely does the temperature drop beneath fifty degrees Fahrenheit. The most humid months tend to be June through August, and the precipitation is noticeable. Winter Park can also experience heavy rainfall and occasional thunderstorms, which rarely leads to flooding from the nearby bodies of water.

Recreation / Things To Do

Winter Park is a phenomenal place to get out and experience some of the most famous activities in all of Florida – namely, those of Disney World, its surrounding resorts, and numerous other clubs, lounges, theme parks and outdoor activities. Winter Park is one of the quieter places to enjoy your vacation, and the natural beauty of Florida, in style. Naturally, Winter Park itself doesn’t lack for things to do either, with numerous parks, tours and outdoor activities that will keep you and the whole family entertained.

Shopping

Winter Park is surrounded by shopping opportunities, no matter what kind of shopper you are. Winter Park has plenty in the way of gift shops, fashion boutiques, and a slew of other retail outlets for you to indulge in some proper retail therapy or go treasure hunting. No matter what you are looking for, you are sure to enjoy the hunt in Winter Park. It’s most popular shopping area is on Park Avenue, as a pro tip to all the shopping warriors out there.

Restaurants

Winter Park has no shortage of delicious eateries for hungry denizens out there. With an exotic mix of foods from around the world as well as modern and classic American cuisine, you can’t find yourself hungry in a better place than Winter Park, no matter what kind of craving has you salivating.

Nightlife

Winter Park is a great place to get out at night, and one of the best areas to get out in style. This suburban city is surrounded by glitz and glamour on all sides, and any night owl can get out and spend the night with a cold one in hand or dancing away. No matter your preference, you’ll have one memorable evening out in Winter Park.

  • Park Social – 358 North Park Avenue – (407) 636-7020

  • The Parkview – 136 S Park Ave – (407) 647-9103

  • Scratch – 223 W Fairbanks Ave – (407) 325-5165

  • Wine Room – 270 S Park Ave – (407) 696-9463

Schools

Winter Park isn’t just a great place to retire or vacation, it’s also a great place to raise a family. With a fantastic school system in place for any age, Winter Park can keep your kids in a nice educational program while you head off to fish, enjoy the local theme parks, or just enjoy the area for all its worth.

Demographics

  • Population: 28,283

  • Population Density: 3,256

  • Median Age: 41.8

  • Male / Female Ratio: 1.0:1

Local / Notable Employers

For those who are looking to make the move to Winter Park, the local job market is not in short supply. There are a feature of many big names and hubs, as well as smaller boutiques, shops and restaurants that can make use of all kinds of varying talent residents might have to offer. There are plenty of big names, including the mouse himself, looking for talent.

Landmarks

If you want to step out of the water for a bit and enjoy some local history or culture, Winter Park is in the perfect place to do so. Not only do you have the rich history of Winter Park itself, but also the neighboring Walt Disney World and many other attractions and historical marvels to enjoy.

Conclusion

Winter Park is a fantastic city for everyone. It has all the amenities that both potential residents and visitors can enjoy: great shopping, delicious food, educational opportunities and so much more. No matter your reason for coming to Winter Park, you are sure to find plenty of reasons to enjoy your stay.

Winter Park Property Alert

Be the first to know when new Winter Park short sales, foreclosures, deeply discounted homes, and brand new hot properties come onto the market before anyone else - over 30% more listings than Trulia, Zillow and Realtor.  

Get Signed Up Now!

Contact Us 

Whether you need to get pre-approved for a mortgage, deal with a savvy buyers agent to find the perfect home, or an experienced listing agent to get your home sold...  

Contact Us Today!

Latest Real Estate for Sale in Winter Park

$3,600,000
4 Beds 5 Baths Detmar Terrace Winter Park SubDv. 32789 Zip Code
Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light. The main level offers two bedrooms and three full bathrooms, including a primary suite with a versatile bonus room behind French doors—perfect for a private office, gym, or additional bedroom. The ensuite features two walk-in closets, a double sink vanity, a large rainfall shower, and a soaking tub. The open-concept floorplan features a beautifully appointed kitchen with high-end appliances and custom cabinetry, flowing seamlessly with the dining area and the spacious living room, where a gas fireplace creates a welcoming gathering space. Architectural light wood ceiling beams, plantation shutters, and expansive glass sliders frame beautiful views of the outdoor living area. Upstairs, two additional bedrooms each feature private ensuite baths and balconies, complemented by a kitchenette and additional living space. This flexible layout is ideal for multigenerational living, guests, live-in staff, or simply creating a private retreat within the home. Designed for effortless indoor-outdoor living, the entire downstairs opens to a private backyard oasis featuring a sparkling saltwater pool, lush bamboo backdrop, summer kitchen, gas fireplace, and outdoor shower. The covered lanai is equipped with automatic screens, creating an inviting and comfortable space to enjoy the outdoors year-round. Beyond its sophisticated design, the home offers exceptional functionality, including an oversized two-car garage pre-wired for EV charging, whole-home surround sound, hurricane-impact windows, a whole-house Generac generator, indoor built-in sprinkler system, dual laundry rooms, and enhanced insulation for exceptional peace and quiet. The entire first floor is completely wheelchair accessible. Tastefully furnished and offered with all furnishings, this exceptional residence presents a rare combination of refined design, thoughtful functionality, and classic Winter Park charm. Ideally located just one mile from Park Avenue and minutes from Winter Park’s renowned restaurants, shops, hospitals, schools, and scenic Lake Osceola, this is a home designed for both elevated living and everyday comfort.

276 Detmar Drive, Winter Park

$1,949,500
3 Beds 4 Baths Sylvan Lake Shores SubDv. 32789 Zip Code
Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water views, the home combines refined craftsmanship and extraordinary lakefront serenity with warm European Contemporary architecture influenced by Belgian design and Organic Modern principles. Expansive, minimalist-profile windows frame the water from nearly every principal living space, while a dramatic 12-foot sliding glass wall connects the open living area to approximately 1,500 square feet of additional outdoor living. Multiple terraces, an integrated outdoor kitchen and beautifully landscaped surroundings create an exceptional setting for waterfront entertaining or quiet mornings beneath the oak canopy. Inside, natural wood, matte black accents, architectural lighting and tactile materials establish a cohesive, warm and inviting aesthetic. Custom white oak wall panels made in Spain, hand-cut white oak beams and architectural transitions, a textured brick feature wall, built-in Sonos audio and a dedicated entertaining bar reflect the attention given to every detail. The European-inspired kitchen features full-height cabinetry incorporating materials imported from Portugal, extensive integrated pantry storage, a Thermador appliance suite with a 36-inch range and griddle, and a Miele steam oven. Positioned at the heart of the living area, the kitchen creates an effortless setting for everyday life and entertaining, always with the lake close at hand. Each of the home’s three bedrooms includes a private en-suite full bath, with an additional powder room serving the common areas. A flexible lake-view office—currently used as a fitness and sauna studio—offers an inspiring setting for work, wellness or creative pursuits. The primary suite opens through nearly eight feet of accordion-style glass doors to a private rooftop terrace, inviting morning coffee, yoga, sunbathing or evening movies beneath the sky. Beyond its architectural design, the comprehensive transformation includes a new roof and roof components, electrical wiring, plumbing and piping, four-zone HVAC system, windows, stucco, drywall, flooring, kitchen and bathrooms. The result combines the character, proportions and established setting of an Old Winter Park home with the quality, efficiency and peace of mind expected from a modern custom residence. Turnkey, distinctive and intimately connected to the water, this exceptional home brings together architectural vision, modern livability and the coveted Winter Park lifestyle on the shores of Lake Sylvan.

1420 Aloma Avenue, Winter Park

Start Your Search