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Winter Park, FL Homes for Sale — Page 9 | Realty.com

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3 beds New construction With a pool

Homes for Sale in Winter Park, FL

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24 of 351 Listings

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24 of 351 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

13Active
$1,250,000
4 bd · 1 ba · 1,260 sqft
230 Killarney Dr, Winter Park, FL
Shandy Ortiz · PREMIER SOTHEBYS INT'L REALTY
13Active
$1,275,000
3 bd · 3 ba · 1,329 sqft
240 Killarney Dr, Winter Park, FL
Shandy Ortiz · PREMIER SOTHEBYS INT'L REALTY
49Active
$775,000
4 bd · 3 ba · 1,899 sqft
1562 Arbor Park Dr, Winter Park, FL
Abby Greenberg · COMPASS FLORIDA LLC

10Active
$335,000
3 bd · 3 ba · 1,790 sqft
2526 Passamonte Dr #10F, Winter Park, FL
Kathi Thomas · LEGACY CORNERSTONE INC
Price Reduced15Active
$164,500
1 bd · 1 ba · 732 sqft
1500 Gay Rd #4D, Winter Park, FL
Janice Erickson · REALCOM REAL ESTATE SERVICES INC
Price Reduced21Active
$1,999,900
3 bd · 2 ba · 1,765 sqft
1133 Bella Lago CV, Winter Park, FL
Hang Kendall · LPT REALTY, LLC
Price Reduced13Active
$270,000
3 bd · 3 ba · 1,803 sqft
2487 Harbour Way, Winter Park, FL
Joel Garay · LOKATION
Price Reduced45Active
$170,000
2 bd · 3 ba · 1,031 sqft
7450 Wynnewood Sq #189, Winter Park, FL
Kim King · REAL ESTATE PROFESSIONALS SE
Price Reduced30Active
$1,875,000
4 bd · 4 ba · 3,440 sqft
922 N Pennsylvania Ave, Winter Park, FL
Mick Night · PREMIER SOTHEBY'S INTL. REALTY
10Active
$1,600,000
4 bd · 4 ba · 2,568 sqft
250 Killarney, Winter Park, FL
Nancy Rossman · FLORIDA PROPERTY SPECIALIST
Price Reduced46Active
$699,500
4 bd · 3 ba · 2,197 sqft
1418 Lone Feather Trl, Winter Park, FL
Harif Hazera LLC · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced26Active
$399,999
4 bd · 2 ba · 1,653 sqft
1401 Aster Ct, Winter Park, FL
Brian Dodd · SPARROW REALTY & RENTALS
Price Reduced28Active
$1,495,000
3 bd · 3 ba · 1,944 sqft
462 W Lyman Ave, Winter Park, FL
Mick Night · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced38Active
$368,000
4 bd · 2 ba · 1,240 sqft
885 Carnation Dr, Winter Park, FL
Tashania Brown · RADIUS REALTY GROUP LLC
Price Reduced37Active
$250,000
3 bd · 2 ba · 1,311 sqft
2450 Grand Teton Cir #2450, Winter Park, FL
John Campese · CHARLES RUTENBERG REALTY ORLANDO
Price Reduced30Active
$439,900
3 bd · 1 ba · 1,508 sqft
2041 Jewell Ave, Winter Park, FL
Martha Coronel · IAD REAL ESTATE
Price Reduced30Active
$549,900
3 bd · 2 ba · 1,837 sqft
1003 Lake Bell Dr, Winter Park, FL
Bryan Douglas · KELLER WILLIAMS REALTY AT THE PARKS
15Active
$2,549,000
5 bd · 5 ba · 3,479 sqft
1823 Sunset Dr, Winter Park, FL
Christopher Christensen · ONE LUXURY INTERNATIONAL LLC
Price Reduced31Active
$275,000
2 bd · 2 ba · 1,008 sqft
5184 Lazy Oaks Dr, Winter Park, FL
Joyce Gary · PAINE-ANDERSON PROPERTIES, INC
Price Reduced34Active
$539,000
3 bd · 3 ba · 1,602 sqft
7641 Village Green Drive, Winter Park, FL
Jannett Jhasmin Marten · Compass Florida, LLC
42Active
$279,900
2 bd · 2 ba · 1,295 sqft
2305 Sun Valley Cir, Winter Park, FL
Ryan Barnett · MARKET CONNECT REALTY LLC
42Active
$285,000
2 bd · 2 ba · 1,495 sqft
2372 Sun Valley Cir #2372, Winter Park, FL
Sheila Mathews · COLDWELL BANKER REALTY
Price ReducedOpen house Sun, Oct 4 · 2:00 PM57Active
$1,525,000
4 bd · 4 ba · 3,723 sqft
341 E Reading Way, Winter Park, FL
Wendy Williams Crumit · FANNIE HILLMAN & ASSOCIATES
Price Reduced11Active
$138,000
1 bd · 1 ba · 776 sqft
1000 S Semoran Blvd #408, Winter Park, FL
Scott Butts · KIMBRIDGE REALTY, LLC

1…8 9 10…15

Listing data & MLS disclosures

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-09-26 15:38:47 UTC
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Winter Park housing market

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 17 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 40.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,731 sq. ft.

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Explore Winter Park homes

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L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

Listing data & MLS disclosures

BeachesMLS: All listings featuring the BMLS logo are provided by Beaches MLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Listing information ©2026 Beaches Multiple Listing Service®. All Rights Reserved. Data Last Updated: 2026-09-26 15:38:47 UTC
Stellar MLS: Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Homes Over $3M

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New Construction Homes
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Nearby areas

ZIP codes

34747 (2,170)
34787 (1,390)
34746 (1,138)
33897 (841)
34771 (693)
32757 (595)
32771 (551)
34714 (551)

Cities

Orlando (3,872)
ORLANDO (3,805)
Kissimmee (2,015)
KISSIMMEE (1,990)
Winter Garden (694)
WINTER GARDEN (648)
Davenport (614)
DAVENPORT (613)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Winter Park, FL community profile

Population: 31,855
Median income: $98,252
Housing units: 15,404
People per sq. mi.: 1,409.5
Area: 22.6 sq. mi.

Source: HJN community data

Winter Park housing market

September 2026 · This period is still settling

Selling at 97.9% of asking price

Buyers here are paying below asking. MLS · 73 sales · as of Sep 29, 2026

Homes that sold · County records, as of Sep 16, 2026

Median sale price: $632,500$389,375–$1,088,750 typical range
Price per sq. ft.: $379
Sales: 60
Paid in cash: 50.0%

Homes on the market · MLS, as of Sep 27, 2026–Sep 29, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 17 days

Price trend · Assessor repeat sales, as of Sep 30, 2026

Year-over-year: 40.9%

Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

Median home size: 1,731 sq. ft.

Nearby areas

ZIP codes

34747 (2,170)
34787 (1,390)
34746 (1,138)
33897 (841)
34771 (693)
32757 (595)
32771 (551)
34714 (551)

Cities

Orlando (3,872)
ORLANDO (3,805)
Kissimmee (2,015)
KISSIMMEE (1,990)
Winter Garden (694)
WINTER GARDEN (648)
Davenport (614)
DAVENPORT (613)