Realty.com
Buy

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
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Registered offenders on the map

Save search

Registered offenders on the map

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Realty.com
Buy

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
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

Registered offenders on the map

Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search
3 bedsNew constructionWith a pool
351 listings

Homes for Sale in Winter Park, FL

Homes for Sale in Winter Park, FL

Hide Map
22 of 351 Listings
Map

Homes for Sale in Winter Park, FL

22 of 351 Listings

  1. 1000 S Semoran Blvd #306 — photoPrice Reduced13
Active

$138,000

1 bd · 1 ba · 796 sqft

1000 S Semoran Blvd #306, Winter Park, FL

Scott Butts · KIMBRIDGE REALTY, LLC

  • 1000 S Semoran Blvd #404 — photoPrice Reduced5Active

    $138,000

    1 bd · 1 ba · 776 sqft

    1000 S Semoran Blvd #404, Winter Park, FL

    Scott Butts · KIMBRIDGE REALTY, LLC

  • 2228 Azalea Pl — photo72Active

    $5,600,000

    5 bd · 6 ba · 5,152 sqft

    2228 Azalea Pl, Winter Park, FL

    Quentin Green, II · COMPASS FLORIDA LLC

  • 1138 S Pennsylvania Ave — photoPrice Reduced41Active

    $925,000

    3 bd · 3 ba · 2,434 sqft

    1138 S Pennsylvania Ave, Winter Park, FL

    George Stringer · COLDWELL BANKER REALTY

  • 981 Aragon Ave — photoPrice Reduced31Active

    $494,999

    2 bd · 1 ba · 857 sqft

    981 Aragon Ave, Winter Park, FL

    Thomas Bonner · COLDWELL BANKER REALTY

  • 259 Orange Terrace Drive — photoPrice Reduced26Active

    $449,900

    3 bd · 2 ba · 1,248 sqft

    259 Orange Terrace Drive, Winter Park, FL

    Jo Ann Lamar · PREMIER SOTHEBY'S INTL. REALTY

  • 3006 Northwood Blvd — photoPrice ReducedOpen house Sat, Oct 3 · 1:00 PM46Active

    $925,000

    4 bd · 3 ba · 2,075 sqft

    3006 Northwood Blvd, Winter Park, FL

    Daren Ellington · ORLANDO HOMES GROUP LLC

  • 660 W Morse Blvd — photoPrice Reduced70Active

    $2,695,000

    3 bd · 4 ba · 3,286 sqft

    660 W Morse Blvd, Winter Park, FL

    Jennifer Sloan · COMPASS FLORIDA LLC

  • 1564 Lawndale Cir — photo45Active

    $450,000

    4 bd · 3 ba · 1,980 sqft

    1564 Lawndale Cir, Winter Park, FL

    Yahya Chhotani LLC · SET HOMES REALTY LLC

  • 7488 Whisperwood Dr #28 — photoPrice Reduced36Active

    $199,000

    2 bd · 3 ba · 1,578 sqft

    7488 Whisperwood Dr #28, Winter Park, FL

    Miranda Azer · PARKVIEW REAL ESTATE

  • 2712 Tortoise CV — photoPrice Reduced22Active

    $230,000

    2 bd · 1 ba · 924 sqft

    2712 Tortoise CV, Winter Park, FL

    Lisa Wright · CHARLES RUTENBERG REALTY ORLANDO

  • 1591 Cardinal Court — photo44Active

    $2,995,000

    5 bd · 3 ba · 3,523 sqft

    1591 Cardinal Court, Winter Park, FL

    DJ Diamond · Sunset Lakes Realty

  • 512 W Swoope Ave — photo46Active

    $1,399,000

    3 bd · 3 ba · 2,585 sqft

    512 W Swoope Ave, Winter Park, FL

    Carmen Quintana · COLDWELL BANKER REALTY

  • 1500 Gay Rd #3C — photoPrice Reduced26Active

    $235,000

    2 bd · 2 ba · 1,026 sqft

    1500 Gay Rd #3C, Winter Park, FL

    Heather Frazee · FANNIE HILLMAN & ASSOCIATES

  • 151 North Orlando Avenue #142 — photo30Active

    $199,900

    1 bd · 1 ba · 582 sqft

    151 North Orlando Avenue #142, Winter Park, FL

    Chris Creegan · CREEGAN GROUP

  • 2015 Summerfield Rd — photoPrice ReducedOpen house Sat, Oct 3 · 12:00 PM31Active

    $1,262,500

    4 bd · 4 ba · 3,024 sqft

    2015 Summerfield Rd, Winter Park, FL

    Courtney Lindsay · UNITED REAL ESTATE PREFERRED

  • 101 S New York Ave #311 — photoPrice Reduced39Active

    $1,775,000

    3 bd · 4 ba · 3,112 sqft

    101 S New York Ave #311, Winter Park, FL

    Tiffany Grindstaff · KELLY PRICE & COMPANY LLC

  • 1605 Puritan Ave — photoPrice Reduced19Active

    $379,000

    3 bd · 2 ba · 1,285 sqft

    1605 Puritan Ave, Winter Park, FL

    Angelica Tomlinson LLC · CENTURY 21 CARIOTI

  • 437 N Capen Ave — photo36Active

    $849,000

    3 bd · 3 ba · 1,904 sqft

    437 N Capen Ave, Winter Park, FL

    Brandon Geers · COMPASS FLORIDA LLC

  • 2008 Houndslake Drive — photo28Active

    $475,000

    4 bd · 2 ba · 2,250 sqft

    2008 Houndslake Drive, Winter Park, FL

    Kevin McCulty · Mark Spain Real Estate

  • 1840 Aster Dr — photoPrice Reduced20Active

    $384,900

    3 bd · 2 ba · 1,667 sqft

    1840 Aster Dr, Winter Park, FL

    Brendon Spalding · KONA REALTY SERVICES LLC

  • 1316 Blue Stem Ln — photo42Active

    $725,000

    4 bd · 3 ba · 2,196 sqft

    1316 Blue Stem Ln, Winter Park, FL

    Matthew Fong · AFFINITY REALTY LLC

  • 1…91011…15

    Explore Winter Park homes

    By price

    • Homes Under $200K
    • Homes Under $300K
    • Homes Under $400K
    • Homes Under $500K
    • Homes Under $600K
    • Homes Under $700K
    • Homes Under $800K
    • Homes Under $900K
    • Homes Under $1M
    • Homes Under $1.25M
    • Homes Under $1.5M
    • Homes Under $1.75M
    • Homes Under $2M
    • Homes Under $2.25M
    • Homes Under $2.5M
    Realty.com

    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

    Equal Housing OpportunityEqual Housing Lender

    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.

    © 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

  • Homes Over $3M
  • Luxury Homes
  • By bedrooms

    • 2 Bedroom Homes
    • 3 Bedroom Homes
    • 4 Bedroom Homes
    • 5 Bedroom Homes

    By type

    • Single-Family Homes
    • Townhomes
    • Condos

    By feature

    • New Construction Homes
    • Homes with a Pool
    • Waterfront Homes

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    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)
  • 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: 2026-06-20 07:15:48 UTC
    Daytona Beach Area 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 Daytona Beach Area Association of Realtors, Inc®. All Rights Reserved. Last Updated: 2026-10-02 19:57:02 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, 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

    Winter Park 12-month median sale price trend

    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 Homes for Sale — Page 10 | Realty.com