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Start here

Homes for sale by state
Home buying tips
Before you start looking
The buying timeline

Afford it

Today's mortgage rates
Mortgage calculator
How much can I afford?
Get pre-approved

Make the deal

Writing a winning offer
Inspections & appraisals
Closing costs, itemized
Find a buyer's agent

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What's my home worth?
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Get an instant cash offer
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What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

Homes Under $700K in Winter Park, FL

71 listings

Homes Under $700K in Winter Park, FL

Homes Under $700K in Winter Park, FL

24 of 71 Listings

Homes Under $700K in Winter Park, FL

24 of 71 Listings

New28

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Active

$675,000

4 bd · 2 ba · 1,650 sqft

2322 Woodcrest Dr, Winter Park, FL

Jill Healey · KELLER WILLIAMS WINTER PARK

$589,900

4 bd · 2 ba · 2,050 sqft

1409 Aster Ct, Winter Park, FL

Jason Price · RE/MAX SELECT GROUP

$439,900

4 bd · 2 ba · 1,624 sqft

3150 Shady Pine Ave, Winter Park, FL

Sarita Cabrera · WATSON REALTY CORP

$399,900

3 bd · 2 ba · 1,247 sqft

5405 Justine Way, Winter Park, FL

Yanira Suarez · LPT REALTY, LLC

$449,900

4 bd · 2 ba · 1,627 sqft

3209 Heartwood Avenue, Winter Park, FL

James Fitzgibbon · LEDGE REAL ESTATE SOLUTIONS LLC

Price Reduced12Active

$439,900

4 bd · 2 ba · 1,627 sqft

3209 Heartwood Ave, Winter Park, FL

James Fitzgibbon · LEDGE REAL ESTATE SOLUTIONS LLC

$659,000

3 bd · 2 ba · 2,265 sqft

5303 Pine Lily Circle, Winter Park, FL

Jonathan Casique · PM ELITE REALTY LLC

$659,000

3 bd · 2 ba · 2,265 sqft

5303 Pine Lily Cir, Winter Park, FL

Jonathan Casique · PM ELITE REALTY LLC

$675,000

4 bd · 2 ba · 1,688 sqft

2215 Woodcrest Drive, Winter Park, FL

Shari Klafter · KELLER WILLIAMS WINTER PARK

$675,000

4 bd · 2 ba · 1,688 sqft

2215 Woodcrest Dr, Winter Park, FL

Shari Klafter · KELLER WILLIAMS WINTER PARK

$380,000

3 bd · 2 ba · 1,277 sqft

4870 Seminole Ave, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

$380,000

3 bd · 2 ba · 1,277 sqft

4870 Seminole Avenue, Winter Park, FL

Tamara Mazo Ferro · COLDWELL BANKER REALTY

Price Reduced28Active

$440,000

4 bd · 2 ba · 2,189 sqft

2301 Conifer Ave, Winter Park, FL

Gregory Buckley · LOKATION

$450,000

4 bd · 2 ba · 2,189 sqft

2301 Conifer Avenue, Winter Park, FL

Gregory Buckley · LOKATION

$495,000

4 bd · 2 ba · 1,756 sqft

3020 Nicholson Dr, Winter Park, FL

Kristin Duncan · CHARLES RUTENBERG REALTY ORLANDO

$495,000

4 bd · 2 ba · 1,756 sqft

3020 Nicholson Drive, Winter Park, FL

Kristin Duncan · CHARLES RUTENBERG REALTY ORLANDO

$669,900

3 bd · 2 ba · 1,420 sqft

274 N Ranger Boulevard, Winter Park, FL

Shannon Lee · EXPLORE FLORIDA REALTY SERVICES LLC

Price Reduced38Active

$659,900

3 bd · 2 ba · 1,420 sqft

274 N Ranger Blvd, Winter Park, FL

Shannon Lee · EXPLORE FLORIDA REALTY SERVICES LLC

Price Reduced40Active

$529,000

4 bd · 2 ba · 1,845 sqft

2211 King Richards Court, Winter Park, FL

Nicole Howell · FANNIE HILLMAN & ASSOCIATES

Price Reduced40Active

$529,000

4 bd · 2 ba · 1,845 sqft

2211 King Richards Ct, Winter Park, FL

Nicole Howell · FANNIE HILLMAN & ASSOCIATES

$245,000

2 bd · 2 ba · 913 sqft

1250 S Denning Dr #Unit 233, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

$245,000

2 bd · 2 ba · 913 sqft

1250 S Denning Dr Unit 233, Winter Park, FL

Samuel Kingsford · STOCKWORTH REALTY GROUP

$660,000

4 bd · 4 ba · 1,840 sqft

1016 Aragon Ave, Winter Park, FL

Pam Stewart · PALMANO GROUP RE BROKERAGE LLC

$660,000

4 bd · 4 ba · 1,840 sqft

1016 Aragon Avenue, Winter Park, FL

Pam Stewart · PALMANO GROUP RE BROKERAGE LLC

1 2 3

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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.

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Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

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 · 84 sales · as of Sep 30, 2026

Homes that sold · County records, as of Sep 23, 2026

Median sale price: $602,500$441,750–$1,016,350 typical range
Price per sq. ft.: $358
Sales: 78
Paid in cash: 46.2%

Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

Median list price: $630,000
Homes for sale: 383
Median days on market: 18 days

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

Year-over-year: 38.1%

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.