Winter Park Homes For Sale By Owner (391 Homes)

  • Home For Sale $285,000
    • 3Bed
    • 2Baths
    • 1,476Sq ft
    3456 ASTORIA COURT , Winter Park, Florida

    Lovingly maintained 3/2 with pool, deck, front and back yard pergolas. this is outdoor living at... Read More

  • Home For Sale $359,900
    • 3Bed
    • 2Baths
    • 1,762Sq ft
    2257 HOWARD DRIVE , Winter Park, Florida

    Located in the north corrine neighborhoods of winter park, this 3 bed, 2 bath, 1764 sqft ranch... Read More

  • Home For Sale $97,500
    • 3Bed
    • 2Baths
    • 1,300Sq ft
    150 SCOTTSDALE SQUARE , Winter Park, Florida

    Opportunity knocks, largest 3 bedroom unit in this association. needs to be finished the way you... Read More

  • Home For Sale $75,000
    • 1Bed
    • 1Baths
    • 756Sq ft
    161 SCOTTSDALE SQUARE , Winter Park, Florida

    Cozy condo in great location. very good for rental income.

  • Home For Sale $475,000
    • 2Bed
    • 1Baths
    • 1,232Sq ft
    251 E KINGS WAY , Winter Park, Florida

    Quant two bedroom bungalow located in a quintessential area of beautiful winter park. beautiful... Read More

  • Home For Sale $225,000
    • 2Bed
    • 2.5Baths
    • 1,550Sq ft
    2692 GALLIANO CIRCLE , Winter Park, Florida

    Welcome home to the beautiful vistas at lake howell. this spacious townhome has everything to... Read More

  • Home For Sale $650,000
    • 4Bed
    • 2.5Baths
    • 2,813Sq ft
    2920 COVE TRAIL , Winter Park, Florida

    You won’t want to miss this classic, renovated 1-story wp home! sitting on a quiet cul-de-sac,... Read More

  • Home For Sale $132,000
    • 1Bed
    • 1Baths
    • 645Sq ft
    2500 LEE ROAD #232, Winter Park, Florida

    Enjoy carefree living in this lovely community located on beautiful lake killarney. a community... Read More

  • Home For Sale $450,000
    • 3Bed
    • 2.5Baths
    • 1,866Sq ft
    1273 MICHIGAN AVENUE , Winter Park, Florida

    Stunning new townhome community in the heart of winter park! multiple units available. built by... Read More

  • Home For Sale $95,000
    • 2Bed
    • 2Baths
    • 784Sq ft
    7308 SWALLOW RUN #7308, Winter Park, Florida

    Multiple offers! please submit your highest and best by today at 3pm! attention investors or home... Read More

  • Vacant Land For Sale $230,000
    • 0Baths
    641 NORTHWOOD CIRCLE , Winter Park, Florida

    Great location!!! minutes to park ave and winter park village. clear buildable lot in an... Read More

  • Home For Sale $275,000
    • 2Bed
    • 1.5Baths
    • 1,115Sq ft
    825 DRIVER AVENUE , Winter Park, Florida

    This is a rare opportunity to own a home in winter park for under $300,000. located in desirable... Read More

  • Home For Sale $3,199,000
    • 6Bed
    • 6.5Baths
    • 7,048Sq ft
    671 VIA LUGANO , Winter Park, Florida

    Former parade of home winner underwent a meticulous renovation in 2019 creating the newest... Read More

  • Home For Sale $189,900
    • 3Bed
    • 2.5Baths
    • 1,652Sq ft
    1528 WINTER GREEN BOULEVARD , Winter Park,...

    Very nice townhouse conveniently located between winter park and casselberry. super floor plan... Read More

  • Home For Sale $298,000
    • 3Bed
    • 2Baths
    • 1,602Sq ft
    4403 GLENVIEW LANE , Winter Park, Florida

    Don't miss the opportunity to own this charming 3 bedroom pool home that sits on an oversized... Read More

  • Home For Sale $419,900
    • 4Bed
    • 2Baths
    • 1,940Sq ft
    734 SAINT DUNSTAN WAY #NO, Winter Park,...

    Picture perfect winter park 4 bedroom home on a large quarter acre lot with resort style pool,... Read More

  • Home For Sale $237,900
    • 3Bed
    • 2.5Baths
    • 1,442Sq ft
    3136 CROWN JEWEL COURT , Winter Park, Florida

    Under construction. under constuction....this brand new town home is loaded with luxury features!... Read More

  • Home For Sale $119,900
    • 1Baths
    • 512Sq ft
    700 MELROSE AVENUE #L-1, Winter Park,...

    Beautiful spacious studio! lots of light! super clean with tile and crown moulding throughout!... Read More

  • Home For Sale $179,000
    • 3Bed
    • 2Baths
    • 1,235Sq ft
    1100 PARK GREEN PLACE , Winter Park, Florida

    Take me home! location - location! excellent opportunity to live in a 3 bedroom, 2 bath detached... Read More

  • Other For Sale $0
    • 0Baths
    7608 ALOMA AVENUE , Winter Park, Florida

    Great daycare center opportunity. freestanding street building with brand new daycare center... Read More

Winter Park - Statistics and Home Trends

Actives Activity Chart


$ 1,117,514




$ 317


$ 841,553




$ 329


$ 875,480




$ 244


$ 797,355




$ 265

Average Price
Land in WINTER PARK (32) $ 924,100


$ 807,104




$ N/A

Learn More About Winter Park, Florida

Currently there are 264 homes for sale, 49 condos and apartments for sale, 32 vacant land for sale and 32 townhomes for sale in Winter Park

Learn More About Winter Park, Florida:

Winter Park is a small to mid-sized city in Orange County, Florida in the central region of the state. Located just seven miles northeast of downtown Orlando, Winter Park covers approximately 10 square miles of area and has a population of just over 30,000. Winter Park takes immense pride in its reputation as being a city of arts and culture as well as municipal progress.


Winter Park features a warm and humid subtropical climate, which typically produces a hot and rainy season lasting from May until October and a dryer, more moderate season from November through March. The area's weather is significantly influenced by the movement of the Gulf Stream.


One of the signature community events in Winter Park is the annual Winter Park Sidewalk Art Festival which is one of the nation's oldest and largest juried outdoor art festivals. Since its debut in 1960, the festival has succeeded in its goal to bring local artists and art lovers together. The Festival draws more than 350,000 visitors each year and its most recent iteration saw work displayed from 225 different artists from the more than 1,100 who applied. The Festival has received many community and arts awards including Orlando Magazine’s Central Florida’s Best Festival.


For the best in live stage and music performances, Winter Park has multiple options for its residents and visitors. The Annie Russell Theatre is a historic theater first opened on the premises of Rollins College in 1931. In 1998, it was added to the U.S. National Register of Historic Places. Local musical theatre lovers frequently attend the Winter Park Playhouse, Central Florida’s only professional musical theatre. Since its inception in 2002, it has been delighting audiences with entertaining, uplifting and inspiring musicals, cabarets and educational outreach programs. The intimacy of the 123-seat theater engages patrons in a unique up-close-and-personal experience.


Winter Park is surrounded by natural beauty and there is no better way to enjoy this than by taking a hike, bike ride, or leisurely stroll through one of the city’s impressive public parks. The crown jewel of the public park system is easily Central Park. This 11-acre park is famous for its beautiful fountains, landscaped planters and oak tree canopy There is also a spectacular Rose Garden located on the southern border of the park. Alternatively, the Kraft Azalea Garden on the shore of Lake Maitland is a quiet 11-acre park has benches for reading, picnic, or just relaxing. There are trails for short walks a small dock that is open for fishing.


Schools in Winter Park are administered through the Orange County School District. Amongst the highest rated schools in the city are: Brookshire Elementary School, Winter Park High School, Lakemont Elementary School, and Lake Howell High School.


With its scenic beauty, amazing public parks, great schools, and strong sense of community spirit, Winter Park is a great destination for just about everyone. offers For Sale By Owner listing services throughout the country. By posting home with ByOwner your property will get the same exposure you’d receive from a traditional real estate company. Our Winter Park, Florida Flat Fee MLS listing Service saves you from paying the traditional 6% commission charged by most real estate offices, but gives you the same worldwide exposure.

Your home will be found on the local MLS, plus all the major search engines and popular real estate portal sites, including: Trulia, Zillow,, MSN, AOL, Bing, Yahoo, and of course Google. Additionally when your home gets added to the MLS, your FSBO listing will listed alongside of the homes listed by ReMax, C-21, Coldwell Banker, ERA, Redfin, Movoto, Keller Williams and all the other nationwide brokerage sites. These sites often display “all” of the MLS postings, not just their own, which means your home will be on these sites also.

The average seller who uses our Flat Rate MLS Listing, will save over $15,000. We give you the tools and exposure you need as a ForSaleByOwner to compete with every other listing in the MLS. But you are in control of the savings and the fees you pay.

Currently Winter Park has 380 properties on the market for sale. The inventory was last updated 12/14/2019. Of these properties, 264 single family homes are for sale by their owners in Winter Park, and 49 condos are for sale by their owners in Winter Park. The average price of the single family homes for sale in Winter Park, is $1,117,514, the average condo price in Winter Park, is $841,553. The average price per square foot of the active inventory is $231. This is based the living area square footage.

Over the last year, there have been 9,205 of properties sold in Winter Park. Of these properties, 6,552 single family homes have sold by their owners in Winter Park, and 1,627 condos have sold by their owners in Winter Park. The average sales price of the single family homes sold in Winter Park, is $729,796. Single family homes have been selling for 227 per square foot of living area. The average sales price of the condos for sale in Winter Park, is $782,075. Condos have been selling for 178 per square foot of living area.

The most active subdivisions with listings for sale in Winter Park, are: Hawk's Crest (19 For Sale), Winter Park Woods Condo (9 For Sale), Lake Killarney Shores (9 For Sale), Winter Park (8 For Sale), Dixie Terrace (8 For Sale), Conwill Estates (6 For Sale), Charmont (5 For Sale), Sylvan Heights (5 For Sale), Lake Forest Park (5 For Sale), Stratford A Winter Park Condo (5 For Sale)

If you are thinking of selling your Winter Park home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 12/14/2019