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Winter Park, FL Homes for Sale — Page 15 | Realty.com

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3 beds New construction With a pool

Homes for Sale in Winter Park, FL

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15 of 351 Listings

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15 of 351 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

Price Reduced23Active
$285,000
2 bd · 1 ba · 710 sqft
151 N Orlando Ave ##115, Winter Park, FL
Chris Creegan · CREEGAN GROUP
Price Reduced34Active
$485,000
4 bd · 2 ba · 2,092 sqft
2217 Sussex Rd, Winter Park, FL
Justin Hilton · PREFERRED REAL ESTATE BROKERS
Price Reduced30Active
$605,000
5 bd · 3 ba · 2,472 sqft
2612 Roxbury Rd, Winter Park, FL
Laura Mcadams · EXP REALTY LLC

Price Reduced8Active
$109,400
1 bd · 1 ba · 785 sqft
311 Scottsdale Sq #311, Winter Park, FL
Omar Rodriguez · EMPIRE NETWORK REALTY
Price Reduced12Active
$285,000
2 bd · 2 ba · 1,669 sqft
2336 Sun Valley Cir #Bldg 20, Winter Park, FL
Lizzie Beaudoin · PR REAL ESTATE SERVICES
Price Reduced12Active
$3,600,000
5 bd · 5 ba · 3,719 sqft
207 E Kings Way, Winter Park, FL
Julie Christensen · ONE LUXURY INTERNATIONAL LLC
Price ReducedOpen house Sat, Oct 3 · 12:00 PM39Active
$3,075,000
5 bd · 6 ba · 3,863 sqft
1821 Englewood Rd, Winter Park, FL
Mick Night · PREMIER SOTHEBY'S INTL. REALTY
33Active
$150,000
1 bd · 1 ba · 749 sqft
2948 Antique Oaks Cir #94, Winter Park, FL
Santiago Silva · THE PAMPAS REAL ESTATE GROUP, LLC.
Price Reduced25Active
$279,000
1 bd · 1 ba · 570 sqft
311 E Morse Blvd #7-11, Winter Park, FL
Mary Colton · FANNIE HILLMAN & ASSOCIATES
Price Reduced27Active
$389,900
4 bd · 2 ba · 1,627 sqft
1849 Viburnum Ln, Winter Park, FL
Lesly Hijar · REAL BROKER, LLC
Price Reduced38Active
$619,500
3 bd · 3 ba · 1,539 sqft
2758 Banchory Rd, Winter Park, FL
Erwin Vargas · MR VARGAS PROPERTY MANAGEMENT LLC
41Active
$460,000
3 bd · 2 ba · 1,263 sqft
5331 Oak Ct, Winter Park, FL
Nataliya Voroshylo Hylton · CHARLES RUTENBERG REALTY ORLANDO
Price Reduced26Active
$179,990
2 bd · 3 ba · 1,031 sqft
3370 Cedar Springs Pl #156, Winter Park, FL
Wendy Lin · SPRINGHILL PROPERTIES LLC
Price Reduced19Active
$89,900
0 bd · 1 ba · 549 sqft
3071 George Mason Ave #5, Winter Park, FL
Katherine Bordelon · CASTLE & COTTAGE REALTY LLC
Price Reduced1Active
$205,000
3 bd · 2 ba · 1,149 sqft
1695 Lee Rd #C202, Winter Park, FL
Hoover Yap · PRIMESTATE REALTY, INC.

1…14 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

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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.

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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New Construction Homes
Homes with a Pool
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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)