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Winter Park, FL Homes for Sale — Page 14 | 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

3Active
$2,070,000
5 bd · 5 ba · 3,617 sqft
914 Enclave Pl, Winter Park, FL
Matthew Burks · CORCORAN PREMIER REALTY
4Active
$1,550,000
4 bd · 4 ba · 2,738 sqft
901 Enclave Pl, Winter Park, FL
Laura Earl · CORCORAN PREMIER REALTY
Price Reduced34Active
$159,000
2 bd · 3 ba · 1,108 sqft
7300 Daniel Webster Dr #M7, Winter Park, FL
Rosa Rodriguez · STIRLING INTERNATIONAL REAL ES

Price Reduced35Active
$159,000
2 bd · 3 ba · 1,090 sqft
3027 Aaron Burr Ave #L1, Winter Park, FL
Rosa Rodriguez · STIRLING INTERNATIONAL REAL ES
Price Reduced42Active
$1,649,000
4 bd · 4 ba · 2,807 sqft
1903 N Park Ave, Winter Park, FL
Chris Creegan · CREEGAN GROUP
Price Reduced20Active
$419,000
4 bd · 2 ba · 1,376 sqft
501 Heritage Blvd, Winter Park, FL
Bernardo Carrasquel · EXP REALTY LLC
Price Reduced9Active
$918,000
4 bd · 3 ba · 2,662 sqft
Lot #21 Karolina Ave, Winter Park, FL
Vinny Lay · COMPASS FLORIDA LLC
Price Reduced52Active
$3,275,000
4 bd · 6 ba · 4,683 sqft
1581 Forest Ave, Winter Park, FL
Julie Christensen · ONE LUXURY INTERNATIONAL LLC
Price Reduced47Active
$612,500
3 bd · 2 ba · 1,785 sqft
2708 Lion Heart Rd, Winter Park, FL
Navid Rokh · EQUITYPRO LLC
58Active
$6,900,000
6 bd · 7 ba · 6,396 sqft
1260 Alabama Dr, Winter Park, FL
Kelly Price · KELLY PRICE & COMPANY LLC
Price ReducedOpen house Sat, Oct 3 · 11:00 AM68Active
$799,000
5 bd · 3 ba · 2,242 sqft
1927 Eland Ave, Winter Park, FL
Ryan Leitter · CHARLES RUTENBERG REALTY ORLANDO
9Active
$1,595,000
3 bd · 2 ba · 2,012 sqft
1113 Via Del Mar, Winter Park, FL
David Barany · BAY HILL REALTY LLC
Price Reduced74Active
$829,500
4 bd · 2 ba · 3,950 sqft
1521 Heron Wood Pl, Winter Park, FL
Ronald Trotter · RE/MAX INNOVATION
Price Reduced50Active
$1,380,000
4 bd · 4 ba · 2,170 sqft
1751 Goodrich Ave, Winter Park, FL
Stephanie Baldner · EXP REALTY LLC
Price Reduced30Active
$539,900
3 bd · 2 ba · 1,570 sqft
330 Elkhorn Ct, Winter Park, FL
Neil Chetram · LA ROSA REALTY CW PROPERTIES L
Price Reduced20Active
$680,000
4 bd · 4 ba · 2,664 sqft
432 W Swoope Ave, Winter Park, FL
Thomas Bonner · COLDWELL BANKER RESIDENTIAL RE
12Active
$1,750,000
4 bd · 3 ba · 2,350 sqft
1840 Anzle Ave, Winter Park, FL
Oscar Rodriguez · B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE
Price Reduced18Active
$268,950
2 bd · 2 ba · 1,036 sqft
3220 Netherwood Dr, Winter Park, FL
Nimrah Ashraf · THE FIRM RE
20Active
$299,999
2 bd · 1 ba · 710 sqft
151 N Orlando Ave #118, Winter Park, FL
Adriana Montes · FLORIDA DREAMS REALTY GRP INC
Price Reduced37Active
$182,900
2 bd · 2 ba · 927 sqft
205 Lewfield Cir #205, Winter Park, FL
Eimi Moreno Carrera · LPT REALTY, LLC
19Active
$499,000
3 bd · 2 ba · 1,088 sqft
2231 Nairn Dr, Winter Park, FL
David Auerbach · PARK TOWN REAL ESTATE LLC
12Active
$499,000
2 bd · 1 ba · 920 sqft
230 Strathy Ln, Winter Park, FL
David Auerbach · PARK TOWN REAL ESTATE LLC
Price Reduced26Active
$184,400
1 bd · 1 ba · 645 sqft
2500 Lee Rd. #222, Winter Park, FL
Christine Bouchard · HOMESMART
Price Reduced29Active
$899,000
2 bd · 2 ba · 1,086 sqft
560 Ololu Dr, Winter Park, FL
Tiffany Yates · COMPASS FLORIDA LLC

1…13 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

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.

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)