Waterfront Homes in Winter Park, FL

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23 of 25 Listings

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Waterfront Homes in Winter Park, FL

23 of 25 Listings

34Active

25 listings

Waterfront Homes in Winter Park, FL

Show Map

23 of 25 Listings

Map

Waterfront Homes in Winter Park, FL

23 of 25 Listings

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

34Active

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

$1,250,000

3 bd · 2 ba · 1,747 sqft

120 Broadview Ave, Winter Park, FL

Catherine D'Amico · FANNIE HILLMAN & ASSOCIATES

45Active

$2,190,000

4 bd · 3 ba · 3,463 sqft

1803 Barker Dr, Winter Park, FL

Garrett Bell · DENOVO REALTY

63Active

$2,475,000

3 bd · 3 ba · 2,316 sqft

311 E Morse Blvd #1-5, Winter Park, FL

Skip Kirst · COLLADO REAL ESTATE

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

18Active

$130,000

1 bd · 1 ba · 645 sqft

2500 Lee Rd #143, Winter Park, FL

Carol Wittman · PALMANO GROUP RE BROKERAGE LLC

25Active

$269,000

2 bd · 1 ba · 710 sqft

151 N Orlando Ave #242, Winter Park, FL

Alexander Scures · COLONIALTOWN REALTY

Price Reduced72Active

$3,750,000

4 bd · 3 ba · 3,377 sqft

2622 Lake Howell Ln, Winter Park, FL

Brian Hyser · THE AGENCY FL

Price Reduced75Active

$1,949,500

3 bd · 4 ba · 2,422 sqft

1420 Aloma Ave, Winter Park, FL

Alejandra Silva · METROPOLITAN R.E SOLUTIONS INC

Price Reduced48Active

$915,000

3 bd · 4 ba · 2,093 sqft

1927 S Lakemont Ave, Winter Park, FL

Abby Green · IAD REAL ESTATE

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

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 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

64Active

$1,725,000

6 bd · 6 ba · 4,173 sqft

2914 Reef Knot Pl, Winter Park, FL

Lianna Dangelo · SOTERA LIVING

42Active

$725,000

4 bd · 3 ba · 2,196 sqft

1316 Blue Stem Ln, Winter Park, FL

Matthew Fong · AFFINITY REALTY LLC

25Active

$3,500,000

4 bd · 4 ba · 4,036 sqft

2240 Venetian Way, Winter Park, FL

Johnny Hurlburt · COLDWELL BANKER REALTY

Price Reduced33Active

$1,498,000

3 bd · 4 ba · 2,467 sqft

1841 Lake Spier Drive, Winter Park, FL

Nicole Seybold · FANNIE HILLMAN & ASSOCIATES

25Active

$1,350,000

3 bd · 2 ba · 1,750 sqft

1881 Lake Spier Dr, Winter Park, FL

Rafael Zenke Pinhao · NOVA REAL ESTATE SERVICES INC

28Active

$825,000

4 bd · 4 ba · 2,589 sqft

1131 Wildmeadow Run, Winter Park, FL

Joann Beck · BECK REALTY LLC

58Active

$6,900,000

6 bd · 7 ba · 6,396 sqft

1260 Alabama Dr, Winter Park, FL

Kelly Price · KELLY PRICE & COMPANY LLC

9Active

$1,595,000

3 bd · 2 ba · 2,012 sqft

1113 Via Del Mar, Winter Park, FL

David Barany · BAY HILL REALTY LLC

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 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

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

August 2026

Selling at 97.6% of asking price

Buyers here are paying below asking. MLS · 90 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $539,000$337,000–$1,175,000 typical range
Price per sq. ft.: $315
Sales: 111
Paid in cash: 40.5%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 11.6%

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

Your local brokerage

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas

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

August 2026

Selling at 97.6% of asking price

Buyers here are paying below asking. MLS · 90 sales · as of Aug 31, 2026

Homes that sold · County records, as of Aug 31, 2026

Median sale price: $539,000$337,000–$1,175,000 typical range
Price per sq. ft.: $315
Sales: 111
Paid in cash: 40.5%

Homes on the market · MLS, as of Aug 31, 2026

Median days on market: 18 days

Price trend · Assessor repeat sales, as of Aug 31, 2026

Year-over-year: 11.6%

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Registered offenders on the map

Your local brokerage

Your local brokerage

Your local brokerage

Listing data & MLS disclosures

Winter Park housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026

Winter Park, FL community profile

Your local brokerage

Listing data & MLS disclosures

Winter Park, FL community profile

Winter Park housing market

Homes that sold · County records, as of Aug 31, 2026

Homes on the market · MLS, as of Aug 31, 2026

Price trend · Assessor repeat sales, as of Aug 31, 2026