Winter Park, FL Real Estate & Homes For Sale

270 homes

  • 1511 Chestnut Ave, Winter Park, FL 32789
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    NEW - 27 MIN AGO
    FANNIE HILLMAN & ASSOCIATES
  • 860 W  New England Ave #5, Winter Park, FL 32789
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    NEW - 4 HRS AGO
    KELLER WILLIAMS WINTER PARK
  • 861 Bonita Dr, Winter Park, FL 32789
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    NEW - 4 HRS AGO0.59 ACRES
    $4,150,000
    6bd
    8ba
    6,939 sqft (on 0.59 acres)
    861 Bonita Dr,
    Winter Park, FL 32789
    PALMANO GROUP RE BROKERAGE LLC
  • 1929 Houndslake Dr, Winter Park, FL 32792
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    NEWOPEN SAT, 12-3PM
    CHARLES RUTENBERG REALTY ORLANDO
  • 1740 Anzle Ave, Winter Park, FL 32789
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    NEW - 5 HRS AGOFORECLOSURE
    ABC REAL ESTATE SERVICES
  • 2606 Lafayette Ave #5, Winter Park, FL 32789
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    NEW - 5 HRS AGO
    CORCORAN PREMIER REALTY
  • 181 Virginia Dr, Winter Park, FL 32789
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    NEW - 7 HRS AGO0.69 ACRES
    $11,795,000
    5bd
    8ba
    8,188 sqft (on 0.69 acres)
    181 Virginia Dr,
    Winter Park, FL 32789
    PREMIER SOTHEBY'S INTL. REALTY
  • 1000 S  Semoran Blvd #510, Winter Park, FL 32792
    NEW - 7 HRS AGO
    SPACES & STYLES GROUP
  • 1801 Legion Dr, Winter Park, FL 32789
    NEWOPEN SAT, 12-2PM0.34 ACRES
    $1,690,000
    5bd
    5ba
    3,518 sqft (on 0.34 acres)
    1801 Legion Dr,
    Winter Park, FL 32789
    FANNIE HILLMAN & ASSOCIATES
  • 2026 Japonica Rd, Winter Park, FL 32792
    NEW - 11 HRS AGO
    MILLER GRANT AND COMPANY
  • 1228 N  Park Ave, Winter Park, FL 32789
    NEW - 1 DAY AGO0.56 ACRES
    $4,500,000
    5bd
    6ba
    5,320 sqft (on 0.56 acres)
    1228 N Park Ave,
    Winter Park, FL 32789
    FANNIE HILLMAN & ASSOCIATES
  • 3065 George Mason Ave #B, Winter Park, FL 32792
    NEW - 1 DAY AGO
    SANDLER MANAGEMENT INC
  • 7543 Dockside St, Winter Park, FL 32792
    NEW - 2 DAYS AGO
    LA ROSA REALTY ORLANDO LLC
  • 215 Sandlewood Trl #7, Winter Park, FL 32789
    NEWOPEN SAT, 10-3PM
    THE WILKINS WAY LLC
  • 3057 Aaron Burr Ave #3, Winter Park, FL 32792
    NEW - 2 DAYS AGO
    GRAVES REALTY
  • 1540 Glencoe Rd, Winter Park, FL 32789
    0.31 ACRES
    $2,790,000
    5bd
    4ba
    4,905 sqft (on 0.31 acres)
    1540 Glencoe Rd,
    Winter Park, FL 32789
    WWW.HOMEZU.COM
  • 110 Lewfield Cir  #110, Winter Park, FL 32792
    OPEN SAT, 12-2PM
    KELLER WILLIAMS WINTER PARK
  • 200 Saint Andrews Blvd #2701, Winter Park, FL 32792
    WINTER PARK REAL ESTATE CO LLC
  • 1161 Lincoln Cir, Winter Park, FL 32789
    0.25 ACRES
    $2,495,000
    4bd
    4ba
    3,154 sqft (on 0.25 acres)
    1161 Lincoln Cir,
    Winter Park, FL 32789
    FANNIE HILLMAN & ASSOCIATES
  • 1364 Blue Stem Ln, Winter Park, FL 32792
    FLORIDA LUXURY REALTY INC
  • 7448 Woodburn Ct #30, Winter Park, FL 32792
    KELLER WILLIAMS INTERNATIONAL LIFESTYLES
  • 1000 S  Semoran Blvd #806, Winter Park, FL 32792
    FOLIO REALTY LLC
  • 985 Lincoln Cir, Winter Park, FL 32789
    NEW CONSTRUCTION
    $4,250,000
    5bd
    7ba
    3,660 sqft
    985 Lincoln Cir,
    Winter Park, FL 32789
    UNITED REAL ESTATE PREFERRED
  • 2837 Wright Ave #130, Winter Park, FL 32789
    OPEN SUN, 1-3:30PM
    FANNIE HILLMAN & ASSOCIATES
  • 1340 Chestnut Ave, Winter Park, FL 32789
    0.25 ACRES
    $2,450,000
    6bd
    6ba
    4,182 sqft (on 0.25 acres)
    1340 Chestnut Ave,
    Winter Park, FL 32789
    WRA BUSINESS & REAL ESTATE
  • 7350 Swallow Run, Winter Park, FL 32792
    GHALI REALTY, INC
  • 3676 Hedgewood Dr, Winter Park, FL 32792
    OPEN SUN, 2-4PM
    CHARLES RUTENBERG REALTY ORLANDO
  • 1563 Lakehurst Ave, Winter Park, FL 32789
    0.4 ACRES
    $3,095,000
    5bd
    6ba
    4,216 sqft (on 0.40 acres)
    1563 Lakehurst Ave,
    Winter Park, FL 32789
    PREMIER SOTHEBY'S INTL. REALTY
  • 101 S  New York Ave #304, Winter Park, FL 32789
    PREMIER SOTHEBY'S INTL. REALTY
  • 2710 Euston Rd, Winter Park, FL 32789
    OPEN SAT, 11-2PM0.28 ACRES
    $625,000
    4bd
    3ba
    1,946 sqft (on 0.28 acres)
    2710 Euston Rd,
    Winter Park, FL 32789
    EXP REALTY LLC
  • 1051 Aragon Ave #1051, Winter Park, FL 32789
    FANNIE HILLMAN & ASSOCIATES
  • 840 W  Canton Ave, Winter Park, FL 32789
    OPEN SUN, 10-1PM
    RE/MAX 200 REALTY
  • 2817 Eastern Pkwy, Winter Park, FL 32789
    THE KEY REALTY GROUP
  • 1140 Washington Ave, Winter Park, FL 32789
    0.54 ACRES
    $725,000
    3bd
    3ba
    2,069 sqft (on 0.54 acres)
    1140 Washington Ave,
    Winter Park, FL 32789
    FLORIDA REALTY INVESTMENTS
  • 3526 Arbutus Ln, Winter Park, FL 32792
    OPEN SAT, 1-2PM
    COLDWELL BANKER REALTY
  • 130 Scottsdale Sq #130, Winter Park, FL 32792
    TRUSTHOME PROPERTIES INC
  • 1250 Denning Dr #210, Winter Park, FL 32789
    REALTY GROUP SPECIALISTS, LLC

Winter Park, FL Real Estate Trends

Learn about the Winter Park, FL housing market through trends and averages.

Affordability of Living in Winter Park, FL

The median home value is $461,898
MonthMedian home value
April 2023$437k
May 2023$439k
June 2023$441k
July 2023$444k
August 2023$446k
September 2023$448k
October 2023$450k
November 2023$452k
December 2023$455k
January 2024$457k
February 2024$460k
March 2024$462k
View as a graph
Trends and affordability stats are provided by third party data sources.

Average Home Value in Winter Park, FL, by Home Size

Currently, there are 23 new listings and 270 homes for sale in Winter Park.
Home SizeHome Value*
1 bedroom (26 homes)$168,816
2 bedrooms (64 homes)$283,332
3 bedrooms (71 homes)$436,633
4 bedrooms (65 homes)$679,022
*Home value over the past month

Explore Neighborhoods in Winter Park, FL

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Neighborhood stats provided by third party data sources.

What Locals Say about Winter Park

  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
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  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
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  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
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  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
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  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
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  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
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  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
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  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
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  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
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  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
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  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
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  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
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  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
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  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
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  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
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  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
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  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
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  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
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  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
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  • Supak77
    "I just moved here and so far I feel very safe walking my dog early in the morning and late in the evening. Neighbors are very friendly and greet you. "
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  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
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  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
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  • Wolverine09
    "It is safe and quite, people are very friendly and respectfully, I never have any problem with my neighbors. Also this is a very clean neighborhood, people walks there dogs and they pick their poops. I got not regret for buy here."
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  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
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  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
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  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
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  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
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  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
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  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
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  • Andreaaarndel
    "Have been here for a year and the kids in this neighborhood are good kids I trust my kids outside. It’s quiet and everybody is to them self. "
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  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
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  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
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  • Alejandratapia01
    "Yes, I see people in the morning walk there dog every day , evening and also night. They are a lot of park near By."
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  • Ryanbarwise
    "There isn’t a lot of variety, so walks get a little mundane. The neighborhoods in my area are also separated from one another which makes taking different routes a little difficult. The neighborhoods are quite small which also limits variety. "
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  • Skiponthestrip
    "Downtown Winter Park is a very family friendly community. The park is a great place to bring the family for a relaxing afternoon or to be entertained by one of the many events that take place throughout the year. "
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  • Oviedohome
    "Need to drive to work. Can walk to local parks. Walking or biking other places does not feel so friendly even though there are restaurants and grocery stores nearby. There are two commuter train stations close by. "
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  • Kathy S.
    "my neighborhood has great access to public transportation and shops and restaurants. it can get very congested because it's popular., which can be good and bad. Can get a little noisy. "
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  • Michael F.
    "I’ve lived here for 4 years, almost. It’s a quiet neighborhood despite the annoying fireworks. But people are nice. "
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  • Jill
    "I love the sense of community in Orwin Mano! Great neighbors, great events and you can walk to restaurants and pubs and gift shops."
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  • Richardc.harmon01
    "when people are in need others will help them out even though they don't know them. also certain neighbors will watch the kids while they play outside and allow you to borrow cool spices from their house when you ask for them."
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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511