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Winter Park, FL Homes for Sale — Page 11 | 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 350 Listings

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24 of 350 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced59Active
$455,000
4 bd · 3 ba · 1,903 sqft
8433 Commander CV, Winter Park, FL
Brandi Cepeda · CEPEDA REAL ESTATE LLC
Price Reduced38Active
$810,000
3 bd · 4 ba · 2,030 sqft
1265 Arlington Pl, Winter Park, FL
Erika Beerbower · FANNIE HILLMAN & ASSOCIATES
Price Reduced15Active
$420,000
3 bd · 2 ba · 1,676 sqft
1535 Lawndale Cir, Winter Park, FL
Raul Pino · SOVEREIGN REAL ESTATE GROUP

Price ReducedOpen house Sun, Oct 4 · 2:00 PM44Active
$2,050,000
5 bd · 5 ba · 2,889 sqft
240 N Phelps Ave, Winter Park, FL
Nick McKee · KELLER WILLIAMS WINTER PARK
Price Reduced67Active
$4,700,000
4 bd · 7 ba · 5,550 sqft
231 Chelton Cir, Winter Park, FL
Joseph Doher · BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY
28Active
$199,900
2 bd · 1 ba · 851 sqft
2500 Lee Rd #220, Winter Park, FL
Thomas Nickley, Jr · KELLER WILLIAMS REALTY AT THE PARKS
Price ReducedOpen house Sun, Oct 4 · 12:00 AM38Active
$1,369,000
5 bd · 4 ba · 2,446 sqft
1473 Berkshire Ave, Winter Park, FL
Gilson Rodrigues · KARDOSH REALTY
Price Reduced23Active
$242,400
2 bd · 2 ba · 956 sqft
2500 Lee Rd #104, Winter Park, FL
Stephen Hachey · FLAT FEE MLS REALTY
Price Reduced29Active
$494,900
3 bd · 2 ba · 1,565 sqft
2715 Prince John Rd, Winter Park, FL
Donna Peebles · VIA PROPERTIES LLC
50Active
$3,150,000
3 bd · 5 ba · 3,244 sqft
125 S Interlachen Ave #2, Winter Park, FL
Erin Legler · CHARLES RUTENBERG REALTY ORLANDO
Price ReducedOpen house Sun, Oct 4 · 12:00 PM37Active
$1,499,000
3 bd · 5 ba · 2,756 sqft
641 Northwood Circle, Winter Park, FL
Sandra Cuba · PREMIER SOTHEBY'S INTL. REALTY
Price Reduced28Active
$655,000
4 bd · 3 ba · 1,647 sqft
2831 Mulford Ave, Winter Park, FL
Patrick Arenson · UNITED REAL ESTATE PREFERRED
Price Reduced29Active
$2,625,000
3 bd · 4 ba · 3,048 sqft
413 W Morse Blvd, Winter Park, FL
AV Blalock · COLDWELL BANKER REALTY
25Active
$3,500,000
4 bd · 4 ba · 4,036 sqft
2240 Venetian Way, Winter Park, FL
Johnny Hurlburt · COLDWELL BANKER REALTY
Price Reduced57Active
$399,900
3 bd · 2 ba · 1,366 sqft
5503 Albert Dr, Winter Park, FL
Fernando Perez de Armas · AXEN REALTY, LLC
Price Reduced63Active
$649,900
3 bd · 2 ba · 1,370 sqft
840 W Canton Ave, Winter Park, FL
Ken Pozek · REAL BROKER, LLC
Price Reduced37Active
$535,000
3 bd · 4 ba · 1,937 sqft
1250 Formosa Ave, Winter Park, FL
Jeanine Louis, LLC · EXP REALTY LLC
5Active
$500,000
4 bd · 3 ba · 2,031 sqft
2054 Eastbrook Blvd, Winter Park, FL
Melissa Stalzer · LPT REALTY, LLC
48Active
$695,000
4 bd · 3 ba · 2,312 sqft
715 S Ranger Blvd, Winter Park, FL
Chuck Tolfa · DAHLIA REALTY GROUP
Price Reduced52Active
$649,900
3 bd · 3 ba · 1,411 sqft
860 N Denning Dr, Winter Park, FL
LaDarrius Sanders · OUTLET REALTY
Price Reduced42Active
$836,000
3 bd · 3 ba · 2,017 sqft
338 Blue Heron Dr, Winter Park, FL
Samuel Kingsford · STOCKWORTH REALTY GROUP
75Active
$6,000,000
5 bd · 8 ba · 7,397 sqft
1571 Woodland Ave, Winter Park, FL
Vonda Fields · CHARLES RUTENBERG REALTY ORLANDO
Price Reduced38Active
$1,075,000
4 bd · 4 ba · 2,469 sqft
1404 Border Dr, Winter Park, FL
Brian Hyser · THE AGENCY FL
Price Reduced55Active
$469,900
4 bd · 2 ba · 1,624 sqft
1320 Gladiolas Dr, Winter Park, FL
Deborah Morgan · OPTIMA REAL ESTATE

1…10 11 12…15

Listing data & MLS disclosures

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

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, 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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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ZIP codes

34747 (2,305)
34787 (1,391)
34746 (1,328)
33896 (1,092)
33897 (894)
34771 (872)
34744 (687)
32757 (595)

Cities

Orlando (3,895)
ORLANDO (3,805)
Kissimmee (2,292)
KISSIMMEE (2,249)
DAVENPORT (996)

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Nearby areas

ZIP codes

34747 (2,305)
34787 (1,391)
34746 (1,328)
33896 (1,092)
33897 (894)
34771 (872)
34744 (687)
32757 (595)

Cities

Orlando (3,895)
ORLANDO (3,805)
Kissimmee (2,292)
KISSIMMEE (2,249)
DAVENPORT (996)

Davenport (978)

Winter Garden (696)

WINTER GARDEN (648)