Winter Park Other For Sale By Owner (52 Homes)

  • 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 $949,900
    • 5Bed
    • 3Baths
    • 3,297Sq ft
    1741 PINE AVENUE , Winter Park, Florida

    This stunning winter park home is located on the tree streets and is a short walk to phelps park,... Read More

  • Home For Sale $899,000
    • 5Bed
    • 3.5Baths
    • 3,768Sq ft
    5541 HOWELL BRANCH ROAD , Winter Park,...

    Don't miss out on this one of a kind, 3 story home. this home is 5 bedroom, 3.5 bathroom homes... Read More

  • Home For Sale $565,900
    • 5Bed
    • 3.5Baths
    • 2,909Sq ft
    5349 CYPRESS RESERVE PLACE , Winter Park,...

    Located on a cul-de-sac in a desirable gated community in winter park, this 5 bedrooms/3 full... Read More

  • Home For Sale $558,613
    • 5Bed
    • 4Baths
    • 3,532Sq ft
    2214 MARSH SEDGE LANE , Winter Park, Florida

    Under construction. "under construction". brand new energy-efficient home ready february 2020!... Read More

  • Home For Sale $4,699,000
    • 7Bed
    • 8.5Baths
    • 10,493Sq ft
    1941 LEGION DRIVE , Winter Park, Florida

    Stately custom winter park estate on lake maitland spans over 10,000 sq ft, offers... Read More

  • Home For Sale $349,500
    • 5Bed
    • 3.5Baths
    • 2,325Sq ft
    5632 PATS POINT , Winter Park, Florida

    Stunning spacious 5 bedroom 3.5 bath pool home with 1st floor master now available with a winter... Read More

  • Home For Sale $824,000
    • 7Bed
    • 5Baths
    • 3,788Sq ft
    261 SPRING LANE , Winter Park, Florida

    This beautiful 7 bedroom pool home features a traditional layout with formal living and dining... Read More

  • Home For Sale $899,900
    • 5Bed
    • 3.5Baths
    • 2,822Sq ft
    2240 HOWARD DRIVE , Winter Park, Florida

    ***wonderful winter park*** new quality construction!!! this fabulous 5 bedroom, 3 and 1 half... Read More

  • Home For Sale $1,595,000
    • 5Bed
    • 5.5Baths
    • 4,636Sq ft
    1146 KEYES AVENUE , Winter Park, Florida

    One or more photo(s) has been virtually staged. picturesque winter park location! perfectly... Read More

  • Home For Sale $3,050,000
    • 5Bed
    • 5.5Baths
    • 6,272Sq ft
    1637 CHASE LANDING WAY , Winter Park, Florida

    A luxurious lakeside lifestyle awaits you in this exquisite 5 bedroom 5.5 bathroom 6,000+ sq ft... Read More

  • Home For Sale $1,449,999
    • 5Bed
    • 5.5Baths
    • 4,205Sq ft
    402 WORTHINGTON DRIVE , Winter Park, Florida

    Gorgeous newer construction home in winter park! this unique home has 5 oversized bedrooms and 5... Read More

  • Home For Sale $599,000
    • 5Bed
    • 4.5Baths
    • 3,652Sq ft
    1424 LAKE FLORENCE WAY , Winter Park, Florida

    Don't miss your opportunity for this newly constructed winter park 5 bedroom 4.5 bath home in... Read More

  • Home For Sale $995,000
    • 5Bed
    • 4Baths
    • 2,950Sq ft
    1344 INDIANA AVENUE , Winter Park, Florida

    Pre-construction. to be built. pre-construction - don't miss out on this gorgeous new... Read More

  • Home For Sale $2,650,000
    • 7Bed
    • 8Baths
    • 6,700Sq ft
    2615 OGLESBY AVENUE , Winter Park, Florida

    Gorgeous custom home on skiable lake now available. 1st place parade of homes winner. luxury... Read More

  • Home For Sale $1,300,000
    • 5Bed
    • 4.5Baths
    • 4,638Sq ft
    1411 BORDER DRIVE , Winter Park, Florida

    New construction-this beautiful new country-contemporary home was orchestrated by an award... Read More

  • Home For Sale $365,000
    • 5Bed
    • 3Baths
    • 2,350Sq ft
    746 S RANGER BOULEVARD #11, Winter Park,...

    This winter park one-story offers quartz kitchen countertops, a breakfast bar, and a two-car garage. Read More

  • Home For Sale $2,875,000
    • 5Bed
    • 5.5Baths
    • 5,000Sq ft
    1071 LAKEVIEW DRIVE , Winter Park, Florida

    Quintessential winter park lakefront living at its best, an incredible opportunity to own a... Read More

  • Home For Sale $407,000
    • 5Bed
    • 2Baths
    • 2,384Sq ft
    3251 ELLWOOD COURT , Winter Park, Florida

    Move right into this 5 bedroom 2 bath beautiful pool home. this home has been totally remodeled... Read More

  • Home For Sale $530,000
    • 5Bed
    • 4Baths
    • 2,486Sq ft
    2711 GOLDENROD DRIVE , Winter Park, Florida

    Start packing! this elegant 5 bedroom 4 bath pool home in winter park home has all the bells and... Read More

Winter Park - Statistics and Home Trends

Actives Activity Chart


$ 1,120,759




$ 319


$ 843,377




$ 329


$ 877,676




$ 246


$ 799,184




$ 265

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


$ 808,793




$ N/A

Learn More About Winter Park, Florida

Currently there are 258 homes for sale, 49 condos and apartments for sale, 32 vacant land for sale and 31 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 373 properties on the market for sale. The inventory was last updated 12/14/2019. Of these properties, 258 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 $1,120,759, the average condo price in Winter Park, is $843,377. The average price per square foot of the active inventory is $232. 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