Homes, values and local insight for Winter Park, Orange County, Florida. Typical home value $465,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Winter Park is known for Park Avenue, a brick-lined downtown of shops and sidewalk cafes facing the 11-acre Central Park. It is home to Rollins College and the Morse Museum, which holds the world's most comprehensive Louis Comfort Tiffany collection. A chain of lakes linked by narrow canals runs through town, and boat tours have shown it off since 1938.
Loring Chase and Oliver E. Chapman bought the land that became Winter Park in 1881. The town incorporated on October 21, 1887, and became a city in 1925. Rollins College opened in 1885 as the first recognized college in Florida, and the 1920s Florida land boom shaped much of the town you see today. About 29,800 people live here, from Rollins students and young families to longtime lakefront owners. Days center on Park Avenue coffee and shopping, Saturday mornings at the farmers' market, and walks under old oaks on brick streets.
The older core near downtown, known for brick streets and big oak canopies. Homes range from older originals to newer builds near the lakes. ( source )
A locally designated historic district (2003) beside Rollins College. Older homes here fall under the city's historic design review. ( source )
Virginia Heights East became a local historic district in 2010. Its older single-family homes fall under historic design review. ( source )
A National Register historic district along Interlachen Avenue close to downtown. Older homes here carry historic character. ( source )
Winter Park's historic African-American community. Today longtime homes sit near the shops and restaurants of the Hannibal Square district. ( source )
A lakeside neighborhood known for the peacocks that roam its streets. Homes here are single-family, set around the lakes. ( source )
Michelin Bib Gourmand since 2022. House charcuterie, wagyu steaks and beer brewed on site. ( source )
Italian · N Park AveItalian classics with modern technique and seasonal ingredients, right on Park Avenue. ( source )
Italian · S Park AveA local favorite since 1993. Known for jumbo meatballs, homemade cheesecake and patio views of Central Park. ( source )
Bakery and brunch · N Park Ave and S Orlando AveDonuts, cakes and all-day breakfast and brunch. Two Winter Park locations. ( source )
American · E New England AveThe restaurant inside The Alfond Inn, where contemporary art from the Rollins collection hangs throughout the hotel. ( source )
American · Lake KillarneyLakeside dining on Lake Killarney with Adirondack chairs for sunset. Known for prime New York strip and key lime pie. ( source )
Southern · Winter ParkSouthern comfort food from John Rivers of 4 Rivers Smokehouse. Fried chicken, shrimp and grits, biscuits and gravy. ( source )
Subs and burgers · N Orlando Ave, MaitlandA no-frills counter diner serving subs, cheesesteaks and hot dogs since 1967. ( source )
The 11-acre green at the heart of Park Avenue, host to the art festivals and the SunRail station. ( source )
Sample from 156 wines by the 1, 2.5 or 5 oz pour from self-serve dispensers. ( source )
An outdoor bar under 400-year-old oaks next to Enzian, the nonprofit single-screen cinema that is home of the Florida Film Festival. ( source )
A 1.5-acre lakeside park with a fishing pier and boat ramp, open 8 a.m. to dusk. ( source )
A 23-acre park on Lake Baldwin and the only city park where dogs can run off leash during posted hours. ( source )
Downtown's main street of boutiques, galleries and cafes. The Chamber welcome center sits just off it on W Lyman Ave. ( source )
The stationery and home goods brand's flagship store in the Hannibal Square district. ( source )
An independent bookstore on Park Avenue with author events and book clubs. ( source )
Every Saturday, 8 a.m. to 1 p.m., in Central Park's West Meadow at New York Ave and Morse Blvd. ( source )
About 47 acres of free trails, a creek, boardwalk, butterfly garden and amphitheater. Open daily 8 a.m. to dusk. ( source )
in townA 5-acre public garden on the shore of Lake Maitland, called Winter Park's secret garden. ( source )
in townAbout 10 acres of wetlands and natural habitat off Howell Branch Road. ( source )
about 4 milesA 50-acre botanical garden with a large camellia collection and the 1888 Leu House Museum. ( source )
about 20 milesThe nearest state park. Swim in a 72 degree spring, paddle the Wekiva River and hike miles of trails. Day-use reservations required. ( source )
about 50 milesUndeveloped barrier island beaches, dunes, Mosquito Lagoon and ancient Timucua shell mounds. ( source )
about 55 milesA 140,000-acre refuge beside Kennedy Space Center. Black Point Wildlife Drive is a top birding route. ( source )
The world's most comprehensive collection of Louis Comfort Tiffany work, including his chapel from the 1893 Chicago World's Fair. ( source )
One-hour cruises through the Winter Park Chain of Lakes and its canals, running since 1938. Tours leave hourly, 10 a.m. to 4 p.m. ( source )
The lakeside home, galleries and gardens of Czech-American sculptor Albin Polasek on Lake Osceola. ( source )
Free museum of the Hannibal Square African-American community, with 200+ archival photos and oral histories. ( source )
Founded in 1885 by New England Congregationalists as the first recognized college in Florida. ( source )
One of the nation's oldest outdoor art festivals, running since 1960 in Central Park and along Park Avenue. ( source )
FallA fall art festival held in Central Park's meadow. ( source )
Every SaturdayLocal produce, baked goods and plants in Central Park's West Meadow. ( source )
Year-round seasonConcerts by the oratorio choir founded in 1935. ( source )
Aloma Elementary, Brookshire Elementary, Lakemont Elementary
MiddleGlenridge Middle
HighWinter Park High School
PrivateTrinity Preparatory School
Listed for reference, not ranked. Confirm school zoning for any address with the district. ( source )
I-4, US 17-92 (Orlando Ave), SR 426 (Aloma Ave/Fairbanks Ave), SR 436 (Semoran Blvd). SunRail and Amtrak stop at the Winter Park station in Central Park.
AirportsOrlando International (MCO): about 25 to 30 min. Orlando Sanford International (SFB): about 30 min.
Downtown Orlando: about 15 min Maitland: about 5 min Walt Disney World: about 40 min Cocoa Beach: about 1 hrRyan and Megan Winslow, broker owners of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Call 386-690-5858 Email Ryan and Megan Get pre-approvedResearched and verified 2026-09-28. Businesses change; call ahead.
The typical home in Winter Park is worth $465,000, 16% above the Orange County typical value of $401,000 and 24% above the Florida typical value of $375,000.
Zillow Home Value Index for Winter Park, August 2026. The middle of the market for single family homes and condos.
Home values in Winter Park moved +24.7% over five years and +91.5% over ten.
Median gross rent in Winter Park. Useful for investors running rental numbers.
Share of occupied homes in Winter Park lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Winter Park.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Winter Park home of $465,000:
Ryan and Megan price Winter Park homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $478,000 · 19,776 residents
Area guide →Typical value $253,000 · 2,356 residents
Area guide →Typical value $345,000 · 31,650 residents
Area guide →Typical value $291,000 · 47,261 residents
Area guide →Typical value $457,000 · 17,089 residents
Area guide →Typical value $424,000 · 39,822 residents
Area guide →See the full Orange County real estate guide or the Florida real estate guide.
The Zillow Home Value Index for Winter Park was $465,000 in August 2026, +1.5% over the past year.
Winter Park is in Orange County, Florida.
About 30,835 people as of the 2024 Census Bureau estimate, up from 29,805 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
66% of occupied homes in Winter Park are owner occupied, based on the 2019 to 2023 American Community Survey.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
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Get coming-soon homes, pocket listings and price drops in Winter Park, FL before they hit the big home search sites.
The typical home in Winter Park is worth $811,947 as of August 2026, across 2 ZIP codes ranging from $394,154 in 32792 to $811,947 in 32789. Values moved +5.6% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 32789 | $811,947 | +5.6% | +32.7% | ||
| 32792 | $394,154 | -0.2% | +22.9% | $425,500 | 25 |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
