MLS Listings for Sale in Winter Park, FL

294 homes

Sort:

Recommended

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Winter Park “Love Shack No More” – 4 Bedrooms, 2 Baths, and Plenty of Potential! When they said “happily ever after, ” they didn’t mention drywall dust and half-finished projects! This 4-bedroom, 2-bath home in highly sought-after Winter Park comes straight from a divorce split, which means one lucky buyer gets the rare chance to finish what love couldn’t — a home with solid bones and serious potential. Some renovations are already underway — think new finishes, updated spaces, and the kind of promise that makes HGTV jealous — while a few projects are still waiting for someone handy (or just brave) enough to see them through. Set

$560,000

4 beds2 baths2,303 sq ft

2758 Sandwell Dr, Winter Park, FL 32792

Quiet street • New finishes • Updated spaces

3D WALKTHROUGH

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Nestled on a quiet cul-de-sac in the heart of Winter Park, this canal-front residence offers the perfect balance of elegance and lifestyle. With direct access to Lake Killarney, the home invites days filled with boating, fishing, and entertaining poolside. Offering a total of 4,798 heated square feet, the property includes the main residence with 3,798 square feet plus a 1,000-square-foot detached guest house with a private entrance, kitchen, living area, bedroom, and full bath—ideal as an in-law suite or private retreat for guests. Inside the main home, the living space unfolds across a single story with soaring ceilings, custom built-ins, and expansive gathering areas. The gourmet k

$2,165,000

5 beds4 baths4,798 sq ft

2001 Lake Dr, Winter Park, FL 32789

Gas cooktop • Gourmet kitchen • Private entrance

VIDEO TOUR

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented by a cozy fireplace, leading into the spacious formal living room with its own gas fireplace and the elegant formal dining room. Gorgeous heart-of-pine floors run throughout the first floor, adding warmth and authenticity. The kitchen has been thoughtfully updated with top-of-the-line Thermador and

$3,100,000

5 beds4.5 baths3,847 sq ft

457 E New England Ave, Winter Park, FL 32789

Updated appliances • Circular drive • 72-bottle wine tower

VIDEO TOUR

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized . 35-acre lot (85x173') with exclusive boathouse access to the prestigious Venetian Canal and Winter Park Chain of Lakes. Steps from the sophisticated boutiques and world-class dining of Park Avenue, this rare find offers the ultimate Winter Park lifestyle where luxury meets convenience. The thoughtfully designed open floorplan showcases expansive living spaces flooded wi

$1,799,000

3 beds3 baths3,297 sq ft

825 Palmer Ave, Winter Park, FL 32789

Screened pool area • Gourmet kitchen • Covered patio

ABOUT THIS HOME
MLS Listings for Sale in Winter Park, FL
just over . 25 acre in winter park with block construction 3 bedroom 2 bath. Opportunity to build new home, add to existing or renovate. Seller financing available for qualified buyers/investors. Occupied and do not disturb.

$425,000

3 beds2 baths1,158 sq ft

2580 Euston Rd, Winter Park, FL 32789

Opportunity to build • Add to existing • Renovate

Property at 1822 Greenwich Ave, Winter Park, FL 32789, 3 beds, 2 baths

$1,199,900

3 beds2 baths1,627 sq ft

1822 Greenwich Ave, Winter Park, FL 32789

Property at 7580 Aloma Pines Ct, Winter Park, FL 32792, 3 beds, 3.5 baths

$364,900

3 beds3.5 baths1,872 sq ft

7580 Aloma Pines Ct, Winter Park, FL 32792

Property at 1920 Carrigan Ave, Winter Park, FL 32792, 3 beds, 2 baths

$315,000

3 beds2 baths1,242 sq ft

1920 Carrigan Ave, Winter Park, FL 32792

Property at 1816 Ivy Ln, Winter Park, FL 32792, 4 beds, 2 baths

$448,800

4 beds2 baths1,725 sq ft

1816 Ivy Ln, Winter Park, FL 32792

Property at 7340 Daniel Webster Dr, Winter Park, FL 32792, 3 beds, 2 baths

$179,900

3 beds2 baths— sq ft

7340 Daniel Webster Dr, Winter Park, FL 32792

(305) 914-7653

Property at 1007 Early Ave, Winter Park, FL 32789, 3 beds, 2 baths

$425,000

3 beds2 baths1,721 sq ft

1007 Early Ave, Winter Park, FL 32789

Property at 100 S Interlachen Ave #415, Winter Park, FL 32789, 2 beds, 2 baths

$1,195,000

2 beds2 baths1,267 sq ft

100 S Interlachen Ave #415, Winter Park, FL 32789

Property at 259 Blossom Ln, Winter Park, FL 32789, 3 beds, 2 baths

$499,000

3 beds2 baths1,354 sq ft

259 Blossom Ln, Winter Park, FL 32789

Property at 1278 S Pennsylvania Ave #13, Winter Park, FL 32789, 3 beds, 2.5 baths

$769,000

3 beds2.5 baths1,957 sq ft

1278 S Pennsylvania Ave #13, Winter Park, FL 32789

Property at 5275 Pine Lily Cir, Winter Park, FL 32792, 5 beds, 3.5 baths

$719,000

5 beds3.5 baths3,152 sq ft

5275 Pine Lily Cir, Winter Park, FL 32792

Property at 740 Baffie Ave, Winter Park, FL 32789, 3 beds, 2 baths

$470,000

3 beds2 baths1,456 sq ft

740 Baffie Ave, Winter Park, FL 32789

Property at 668 Overspin Dr, Winter Park, FL 32789, 4 beds, 3 baths

$950,000

4 beds3 baths2,509 sq ft

668 Overspin Dr, Winter Park, FL 32789

Property at 3102 Heartleaf Pl, Winter Park, FL 32792, 4 beds, 3 baths

$625,827

4 beds3 baths2,672 sq ft

3102 Heartleaf Pl, Winter Park, FL 32792

Property at 1540 Palm Ave, Winter Park, FL 32789, 5 beds, 3.5 baths

$1,999,000

5 beds3.5 baths3,423 sq ft

1540 Palm Ave, Winter Park, FL 32789

Property at 265 E Canton Ave Unit GE, Winter Park, FL 32789, 2 beds, 2 baths

$631,400

2 beds2 baths1,057 sq ft

265 E Canton Ave Unit GE, Winter Park, FL 32789

Property at 1161 Valencia Ave, Winter Park, FL 32789, 4 beds, 4.5 baths

$4,545,000

4 beds4.5 baths4,181 sq ft

1161 Valencia Ave, Winter Park, FL 32789

Property at 3117 Shady Pine Ave, Winter Park, FL 32792, 3 beds, 2 baths

$364,000

3 beds2 baths1,214 sq ft

3117 Shady Pine Ave, Winter Park, FL 32792

Property at 4928 Tangerine Ave, Winter Park, FL 32792, 2 beds, 1.5 baths

$205,000

2 beds1.5 baths1,281 sq ft

4928 Tangerine Ave, Winter Park, FL 32792

Property at 1875 Staunton Ave, Winter Park, FL 32789, 4 beds, 2 baths

$560,000

4 beds2 baths2,036 sq ft

1875 Staunton Ave, Winter Park, FL 32789

Property at 1503 Grove St #559, Maitland, FL 32751, 3 beds, 2 baths

$249,000

3 beds2 baths1,256 sq ft

1503 Grove St #559, Maitland, FL 32751

Property at 1362 Tierra Cir, Winter Park, FL 32792, 4 beds, 3 baths

$425,000

4 beds3 baths2,179 sq ft

1362 Tierra Cir, Winter Park, FL 32792

Property at 7341 Daniel Webster Dr Unit c-2b, Winter Park, FL 32792, 1 bed, 1 bath

$85,000

1 bed1 bath525 sq ft

7341 Daniel Webster Dr Unit c-2b, Winter Park, FL 32792

Property at 1981 Blue Ridge Rd, Winter Park, FL 32789, 4 beds, 2 baths

$1,230,000

4 beds2 baths2,750 sq ft

1981 Blue Ridge Rd, Winter Park, FL 32789

Property at 1261 Indiana Ave, Winter Park, FL 32789, 3 beds, 2.5 baths

$549,900

3 beds2.5 baths1,660 sq ft

1261 Indiana Ave, Winter Park, FL 32789

Property at 1500 Gay Rd Unit 24B, Winter Park, FL 32789, 2 beds, 2 baths

$275,000

2 beds2 baths1,026 sq ft

1500 Gay Rd Unit 24B, Winter Park, FL 32789

Property at 2215 Marsh Sedge Ln, Winter Park, FL 32792, 5 beds, 2.5 baths

$799,000

5 beds2.5 baths2,646 sq ft

2215 Marsh Sedge Ln, Winter Park, FL 32792

Property at 915 Garden Dr, Winter Park, FL 32789, 3 beds, 3 baths

$900,000

3 beds3 baths2,456 sq ft

915 Garden Dr, Winter Park, FL 32789

Property at 151 N Orlando Ave #101, Winter Park, FL 32789, 2 beds, 1 bath

$260,000

2 beds1 bath804 sq ft

151 N Orlando Ave #101, Winter Park, FL 32789

Property at 1710 Oneco Ave, Winter Park, FL 32789, 5 beds, 4.5 baths

$1,945,000

5 beds4.5 baths3,174 sq ft

1710 Oneco Ave, Winter Park, FL 32789

Property at 2087 Laurelwood Way, Winter Park, FL 32792, 4 beds, 2 baths

$689,000

4 beds2 baths1,920 sq ft

2087 Laurelwood Way, Winter Park, FL 32792

Property at 2489 Tahoe Cir, Winter Park, FL 32792, 3 beds, 2 baths

$272,900

3 beds2 baths1,311 sq ft

2489 Tahoe Cir, Winter Park, FL 32792

Property at 887 Georgia Ave, Winter Park, FL 32789, 6 beds, 5.5 baths

$5,900,000

6 beds5.5 baths5,759 sq ft

887 Georgia Ave, Winter Park, FL 32789

Property at 3415 N Goldenrod Rd, Winter Park, FL 32792, 4 beds, 3 baths

$430,000

4 beds3 baths1,906 sq ft

3415 N Goldenrod Rd, Winter Park, FL 32792

Property at 501 W Canton Ave, Winter Park, FL 32789, 3 beds, 2.5 baths

$1,250,000

3 beds2.5 baths2,372 sq ft

501 W Canton Ave, Winter Park, FL 32789

Property at 720 W Webster Ave, Winter Park, FL 32789, 3 beds, 2 baths

$575,000

3 beds2 baths1,356 sq ft

720 W Webster Ave, Winter Park, FL 32789

Property at 700 Melrose Ave Unit D21, Winter Park, FL 32789, 1 bed, 1 bath

$198,800

1 bed1 bath871 sq ft

700 Melrose Ave Unit D21, Winter Park, FL 32789

Viewing page 3 of 8

Based on information submitted to the MLS GRID as of Mon Nov 17 2025. 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.

MLS Listings for Sale in Winter Park

There are currently 294 mls listings for sale in Winter Park at a median listing price of $864K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winter Park stay on the market for 94 days and receive 5 offers. Popular neighborhoods include Audubon Park, College Park, Winter Park Pines, Baldwin Park, and Downtown Maitland. This map is refreshed with the newest listings in Winter Park every 15 minutes.

In the past month, 50 homes have been sold in Winter Park. In addition to houses in Winter Park, there were also 66 condos, 15 townhouses, and 2 multi-family units for sale in Winter Park last month. Winter Park is a minimally walkable city in Orange County with a Walk Score of 44. Winter Park is home to approximately 27,958 people and 25,253 jobs. Find your dream home in Winter Park using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winter Park are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winter Park. Our Winter Park real estate stats and trends will give you more information about home buying and selling trends in Winter Park. If you're looking to sell your home in the Winter Park area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winter Park with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Winter Park, FL

Neighborhoods

Zip Codes

Nearby Cities

Nearby Cities with MLS Listings

Nearby Neighborhoods with MLS Listings

More to explore in Winter Park, FL

Featured
Bedroom

How to buy a house in Winter Park, FL

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Florida

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.