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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
Buy before you sell

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When should I sell?
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Pricing your home
What's worth fixing first
Find a seller's agent

3 beds New construction With a pool

Homes Under $2.5M in Winter Park, FL

313 listings

Homes Under $2.5M in Winter Park, FL

Homes Under $2.5M in Winter Park, FL

24 of 313 Listings

Homes Under $2.5M in Winter Park, FL

24 of 313 Listings

New8

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Active

$2,125,000

5 bd · 5 ba · 3,713 sqft

918 Enclave Pl, Winter Park, FL

Laura Earl · CORCORAN PREMIER REALTY

$299,000

2 bd · 2 ba · 1,032 sqft

170 Balfour Dr #1, Winter Park, FL

Dana Gold · RE/MAX ASSURED

$140,000

1 bd · 1 ba · 678 sqft

302 Lewfield Cir #302, Winter Park, FL

Heather Spirazza · REGENCY REAL ESTATE LLC

$589,900

4 bd · 2 ba · 2,050 sqft

1409 Aster Ct, Winter Park, FL

Jason Price · RE/MAX SELECT GROUP

$170,000

1 bd · 1 ba · 793 sqft

200 Saint Andrews Blvd #3408, Winter Park, FL

Natalia Moege · PARK 26 REALTY LLC

$900,000

4 bd · 3 ba · 2,807 sqft

2052 Wood Thrush Ln, Winter Park, FL

Ron Verzaro, II · KELLER WILLIAMS ADVANTAGE REALTY

$365,000

3 bd · 3 ba · 1,866 sqft

7560 Aloma Pines Ct, Winter Park, FL

Jessica Macias · KELLER WILLIAMS ADVANTAGE III

$850,000

3 bd · 2 ba · 1,639 sqft

100 S Interlachen Ave #401, Winter Park, FL

Mary Colton · FANNIE HILLMAN & ASSOCIATES

$439,900

4 bd · 2 ba · 1,624 sqft

3150 Shady Pine Ave, Winter Park, FL

Sarita Cabrera · WATSON REALTY CORP

$169,900

1 bd · 1 ba · 645 sqft

2500 Lee Rd #123, Winter Park, FL

Scott Sheldon · HOME WISE REALTY GROUP, INC.

$290,000

2 bd · 3 ba · 1,133 sqft

188 Sandlewood #1, Winter Park, FL

Tom Noelke · NOELKE REALTY

$448,000

3 bd · 1 ba · 1,304 sqft

712 Baffie Ave, Winter Park, FL

George Bateman, III · RP INVESTMENT REALTY LLC

$399,900

3 bd · 2 ba · 1,247 sqft

5405 Justine Way, Winter Park, FL

Yanira Suarez · LPT REALTY, LLC

$159,000

1 bd · 1 ba · 793 sqft

200 Saint Andrews Blvd #704, Winter Park, FL

Alexis Jacobsen · EXP REALTY LLC

$1,995,000

4 bd · 4 ba · 3,314 sqft

2007 Edwin Blvd, Winter Park, FL

Angela Rodriguez · DREAM FINDERS REALTY GROUP CORP

$5,000

3 bd · 2 ba · 1,229 sqft

1187 Sawmill Court, Winter Park, FL

Jaime L Boone · Jaime L Boone LLC

$850,000

4 bd · 3 ba · 2,301 sqft

870 N Phelps Ave, Winter Park, FL

Christina Frucci · RE/MAX TOWN & COUNTRY REALTY

$1,950,000

5 bd · 5 ba · 3,560 sqft

513 Dunraven Dr, Winter Park, FL

Alison Mosley · PREMIER SOTHEBY'S INTL. REALTY

$364,900

3 bd · 3 ba · 1,872 sqft

7498 Aloma Pines Ct, Winter Park, FL

Marian Coaxum · KELLER WILLIAMS REALTY AT THE PARKS

$724,900

4 bd · 3 ba · 1,692 sqft

266 N Ranger Blvd, Winter Park, FL

Moises Rivera · ELITE PROPERTY REAL ESTATE LLC

$950,000

3 bd · 3 ba · 1,957 sqft

1256 S Pennsylvania Ave #9, Winter Park, FL

Drew Henner · PREMIER SOTHEBY'S INTL. REALTY

$140,000

2 bd · 1 ba · 881 sqft

1695 Lee Rd #C206, Winter Park, FL

Ingrid Garcia Rodriguez · INVESTMENT REALTY

$410,500

4 bd · 2 ba · 1,301 sqft

7786 Fox Knoll Pl, Winter Park, FL

Eric Senate · NIZZ REALTY INC

$100,000

1 bd · 1 ba · 785 sqft

173 Scottsdale Sq #173, Winter Park, FL

Paola Jimenez · AXEN REALTY, LLC

1 2…14

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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

Space Coast MLS (Space Coast Association of REALTORS): IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Listing information ©2026 Space Coast MLS, Inc®. All Rights Reserved. Last Updated: 2026-09-29 11:01:04 UTC
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