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Winter Park Homes for Sale

Winter Park, Florida, is a suburban city found in Orange County and part of the Orlando-Kissimmee-Sanford metro area. With a rich historic history, Winter Park was founded as a resort community in the early 20th century. Winter Park has grown and is now known for its vibrant main street, luxury communities, museums, galleries, parks and an incredible chain of lakes popular for skiing, boating, fishing and general recreation.

One of the most popular and renowned areas of the City is Park Avenue, a traditional bricked street which provides an amazing variety of fine and casual dining, boutique shopping, entertainment, a central park and museums. The City is home to a public golf club, historic cemetery, train station, art galleries and a famous boating tour. Additional popular activities include visiting the Winter Park Village mall, Annie Russell Theatre, Rollins College, Charles Hosmer Morse Museum of American Art, Cornell Fine Arts Museum, Hannibal Square, Mead Botanical Gardens, Kraft Azalea Park and the Winter Park Historical Museum. The scenic boat tours also provide a great way to see the beautiful luxury homes and natural beauty found throughout the City. Winter Park is also host to the world-famous Winter Park Sidewalk Art Festival, which is the largest and oldest of the art festivals found in the country today.

Winter Park is part of the Orange County Public School system and also boasts great schools from public elementary schools to well-known colleges. Some of the top-ranked schools in Winter Park include: Aloma Elementary School, The Geneva School, The Parke House Academy, Full Sail University, Lakemont Elementary, St. Margaret Mary Catholic School, Trinity Preparatory, Winter Park High, Rollins College, Valencia Community College and the Crealde School of Art.

Winter Park offers many forms of housing including luxury, waterfront, golf front, single-family homes, townhomes, condos, and villas. However, most are single-family homes and tend to be larger with four or more bedrooms. A significant number of the single-family homes have been custom built and target buyers looking for luxurious amenities. A significant number of large estate homes are waterfront and located on the Winter Park Chain of Lakes. The average home listed on the market in Winter Park is about $856K; however, prices can easily range into the multi-millions for some of the larger estate homes.

Some of the most desirable communities in Central Florida are located in Winter Park including Bear Gully Bay, Bear Gully Pointe, Bengerts Bend, Brookshire Heights, Camwood, Charmont, Comstock Park, Conwill Estates, Dixie Terrace, Dubsdread Heights, Ellno Willo, Forest Hills, Fountainhead, Glencoe, Golfview Terrace, Green Oaks, Green Terrace, J Kronenberger, Kenilworth Shores, Killarney Circle, Lake Howell, Lake Howell Lane, Lake Knowles Terrace, Lake Virginia, Maitland Shores, Osceola Place, Park Grove, Sevilla, Shores Lake Killarney, Sicilian Shores, Sylvan Lake Shores, Sylvan Park, Timberlane Shores, Tuscany Place, Tuscany Terrace, Twelve Oaks, Virginia Heights, Windsong and many more.

Looking to sell your home in Winter Park? Follow this link to get an "Instant" Home Value Report

Newest Winter Park Homes for Sale

845 W Canton Avenue, Winter Park $895,900

Under Construction. UNDER CONSTRUCTION - NEW CONSTRUCTION POOL home in "A" rated Winter Park Schools. This residence is walking distance to Winter Park Village and all th...

4 Beds
3 Baths
Canton Residences SubDv.
32789 Zip Code

5116 N Woodcrest Drive, Winter Park image

5116 N Woodcrest Drive, Winter Park $309,000

New Roof, AC (2016), New Water Heater, New Appliances, WINTER PARK sought after city, POOL, spacious backyard, New carpet, New Flooring, oversized 1 car garage.

4 Beds
2 Baths
Woodcrest Unit 01 SubDv.
32792 Zip Code

2852 Scarlet Road, Winter Park $345,000

DON'T MISS THIS OPPORTUNITY IN THE GREAT WINTER PARK PINES with a well-established community. This well maintained house features 3 bedrooms, 2 baths, Spacious living roo...

3 Beds
2 Baths
Winter Park Pines SubDv.
32792 Zip Code

2843 Riddle Drive, Winter Park $315,000

Welcome to the Mid Century Modern Charm of Sunshine Gardens! A prime location, minutes from enjoying Winter Park Avenues Shoppes and Restaurants! Also minutes from the ec...

4 Beds
2.5 Baths
Fairbanks Shores First Add SubDv.
32789 Zip Code

665 Ololu Drive, Winter Park $309,000

Fantastic opportunity in Winter Park! This completely remodeled home has 3 bedrooms, 2 bathrooms, and a study, as well as a 2 car open garage that has an automatic door o...

3 Beds
2 Baths
Killarney Circle SubDv.
32789 Zip Code

2615 Via Tuscany, Winter Park $1,095,000

Elegant modern Mediterranean one-owner home is situated on an oversized Via Tuscany corner lot. The home is within a short distance to Winter Park Racquet Club and the ci...

4 Beds
3.5 Baths
Maitland Shores First Add SubDv.
32789 Zip Code

1913 Sycamore Drive, Winter Park — Modern Farmhouse $915,000

Pre-Construction. To be built. AUDOBON K-8 & WINTER PARK HIGH! Take this opportunity to build as sketched or build-to-suit your ideal home with 2020 Parade of Homes winne...

5 Beds
3.5 Baths
Northwood Terrace SubDv.
32789 Zip Code

1201 Wading Waters Circle, Winter Park image

1201 Wading Waters Circle, Winter Park $731,045

Under Construction. "Under Construction" Brand NEW energy-efficient home ready December 2020! This Kerrville II home features a Game Room/Wet bar, Media Room, Formal Livi...

5 Beds
4.5 Baths
Hawks Crest SubDv.
32792 Zip Code

5365 Mellow Palm Way, Winter Park $529,900

FOR SALE Beautiful Well Maintained 2 Story Home on a Premium Corner Lot. Located in Enclave at Aloma, an Exclusive and Intimate Gated Community with a Winter Park Addres...

4 Beds
4 Baths
Enclave At Aloma SubDv.
32792 Zip Code

2832 Bear Island Pointe, Winter Park image

2832 Bear Island Pointe, Winter Park $815,000

Custom built home located Inside the beautiful, gated, Cypress Reserve neighborhood. Spacious 6 bedroom, 5 bathrooms and 3983 Square feet. This house has LOTS of room f...

6 Beds
5 Baths
Cypress Reserve SubDv.
32792 Zip Code

2011 N Park Avenue, Winter Park $399,000

LOWEST PRICE HOME ON N PARK AVE IN WINTER PARK. HOME CAN BE LIVED IN VALUE IS IN THE LAND 75 FT ON PARK AVE 150 FT DEEP BEAUTIFUL LOT FOR NEW CONSTRUCTION

2 Beds
1.5 Baths
Twin Acres SubDv.
32789 Zip Code

345 W Welbourne Avenue Unit 104, Winter Park image

345 W Welbourne Avenue Unit 104, Winter Park — Douglas Grand $799,000

Opportunity at The Douglas Grand! Enjoy a carefree, urban lifestyle in beautiful downtown Winter Park - just one block from chic Park Avenue with its lovely boutique sho...

3 Beds
3.5 Baths
Douglas Grand/Winter Park Residential Condominium SubDv.
32789 Zip Code

1327 Heavenly Cove, Winter Park $810,000

Be prepared to be impressed with this beautiful 4 bedroom, 3 1/2 bath home with over 4000 sq ft of living space and the most gorgeous, resort style, smart phone controlle...

4 Beds
3.5 Baths
Eden Point SubDv.
32792 Zip Code

1970 Laurel Road, Winter Park $1,300,000

Welcome to this one-of-a-kind contemporary masterpiece, custom-built by LunDev in the heart of highly desired Winter Park! This gorgeous home is enviably located on a qui...

4 Beds
3.5 Baths
Charmont SubDv.
32789 Zip Code

2356 Coldstream Drive, Winter Park image

2356 Coldstream Drive, Winter Park $498,900

Renovated & Fabulous ** You pick your flooring material & bath tile with $15,000 credit at closing ** 1 block from Cady Way Trail ** Open floor plan ** Bonus room for off...

3 Beds
2 Baths
Brookshire Heights SubDv.
32792 Zip Code

311 E Morse Boulevard Unit 2-2, Winter Park image

311 E Morse Boulevard Unit 2-2, Winter Park — 2 $1,300,000

Sweeping views of Winter Park's Lake Osceola. Like-new contemporary home designed by Lamar Design and rebuilt by Brannon Construction in 2015. Unique kitchen, baths and a...

2 Beds
2 Baths
Phillips Circle Rep SubDv.
32789 Zip Code

1251 Indiana Avenue, Winter Park — 1251 $455,000

RARE FIND IN 32789! Welcome to 1251 Indiana Avenue! This stunning Townhome offers: *END UNIT *DOWNSTAIRS MASTER SUITE *2425 sq ft *2 CAR ATTACHED GARAGE *INSIDE LAUNDR...

3 Beds
3.5 Baths
Townhomes At Harper Place SubDv.
32789 Zip Code

1645 Spruce Ave, Winter Park $849,000

Welcome home to this beautiful newer construction contemporary home located in the heart of Winter Park. Amongst million dollar homes and on one of Winter Park’s charming...

4 Beds
3 Baths
Lake Knowles Terrace SubDv.
32789 Zip Code

2433 Via Tuscany, Winter Park $1,275,000

*Check out the 2 Virtual Tours and ask for a Floorplan!* Welcome to a fabulous pool home, in the Winter Park Via’s neighborhood, with all the desirable amenities includin...

5 Beds
3.5 Baths
Maitland Shores First Add SubDv.
32789 Zip Code

570 Country Club Drive, Winter Park image

570 Country Club Drive, Winter Park $1,695,000 ▲

Under Construction. Lakefront Luxury in Winter Park! Have you ever dreamed of grabbing your paddle board for an early morning of tranquility? Or cranking up the boat to t...

5 Beds
5.5 Baths
Lake Killarney Shores SubDv.
32789 Zip Code

141 N Virginia Avenue, Winter Park image

141 N Virginia Avenue, Winter Park — 141 $2,150,000

A fantastic opportunity for a discerning buyer to own Oak Tree House, the "Jewel in the Crown" of the Phil Kean designed Brownstones located in downtown Winter Park. Just...

5 Beds
5.5 Baths
Virginia & Morse Brownstones SubDv.
32789 Zip Code

1251 Richmond Road, Winter Park $1,450,000

The work of a local award-winning designer, this transitional Winter Park classic features a modern exterior elevation, with ornate compliments of very familiar and local...

3 Beds
2.5 Baths
Virginia Heights Rep SubDv.
32789 Zip Code

8021 Pleasant Pine Circle, Winter Park image

8021 Pleasant Pine Circle, Winter Park $679,000

Must see, stunning move-in condition home! Immaculately maintained in like-new condition and loaded with custom upgrades in established gated Winter Park community! Pict...

5 Beds
4 Baths
Enclave At Aloma SubDv.
32792 Zip Code

1641 Woodland Avenue, Winter Park $1,549,000

Elegant Santa Barbara Mediterranean in Olde Winter Park on a quiet, tree-lined brick street with a circular drive, majestic palms and magnolia trees. The current owner ha...

5 Beds
5.5 Baths
Comstock Park SubDv.
32789 Zip Code

756 Mcintyre Avenue, Winter Park — Na $689,000

Just Listed! Walk to Park Avenue from this beautifully maintained 3 bedroom, 2.5 bath townhome in the historic College Quarter neighborhood of Winter Park. Located just b...

3 Beds
2.5 Baths
Trotters Rep SubDv.
32789 Zip Code

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