Winter Park Homes for Sale

Click on the picture to take our photo tour of Winter Park.

About Winter Park, Florida

Winter Park is a city unlike any other in Central Florida. Between the upscale shopping and dining experiences, festivals, and old-world charm, it's easy to see why Winter Park calls itself the "city of arts and culture." Winter Park is home to Rollins College, the first recognized college in the State of Florida. Every Saturday, downtown Winter Park hosts a farmer's market where visitors can pick up fresh produce, coffee beans, or an early morning treat. If you need a break from shopping, take a stroll through the 47-acres of Mead Botanical Garden where visitors are invited to explore the grounds for free.

Our website features the best Winter Park real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Winter Park real estate market? Sign up for a Winter Park Real Estate Market Report to see what’s active, under contract, and sold!

Newest Winter Park Homes for Sale

1813 Pineview Circle, Winter Park $399,000

Great Winter Park Location !!! This lovely, updated, 3/1 block home, located just steps away from Lakemont Elementary and the Winter Park YMCA is tucked away in the quiet...

3 Beds
1 Baths
Lakemont Heights SubDv.
32792 Zip Code

1987 Karolina Avenue, Winter Park $330,000

Cute, clean, and convenient, located in Winter Park just off of Fairbanks near I-4. This lovely home features a remodeled kitchen and bath, refinished original wood floor...

3 Beds
1 Baths
Karolina On Killarney SubDv.
32789 Zip Code

1593 Lawndale Circle, Winter Park $474,900

JUST what you've been looking for!! LIGHT & BRIGHT, Updated 3 bed / 2.5 bath POOL home in desirable COUNTRY LANE in WINTER PARK! No CARPET! MODERN Wood-look VINYL floors...

3 Beds
2.5 Baths
Country Lane SubDv.
32792 Zip Code

678 W Webster Avenue, Winter Park $469,500 ▲

Discover the charm of easy downtown living in this thoughtfully remodeled two-bedroom home located in the vibrant heart of Winter Park. This delightful residence features...

2 Beds
1 Baths
Carver Town SubDv.
32789 Zip Code

500 N Pennsylvania Avenue Unit G, Winter Park image

500 N Pennsylvania Avenue Unit G, Winter Park — Village Condominium $315,000

Step into comfort and convenience with this delightful upstairs residence in the highly sought-after Village Condominiums. Positioned perfectly in a neighborly setting, t...

2 Beds
1 Baths
Village Condos SubDv.
32789 Zip Code

1223 Formosa Avenue, Winter Park $1,325,000

Welcome to this stunning 4 bedroom, 3 bathroom home located in the desirable Winter Park area. Recently updated, this home offers both modern amenities and classic charm....

4 Beds
3 Baths
Golfview SubDv.
32789 Zip Code

1503 Palmer Avenue, Winter Park $1,350,000

Welcome to this rare, single-story residence nestled in the heart of Winter Park! This remarkable 4-bedroom, 3-bathroom home sits on a spacious CORNER lot, boasting a hig...

4 Beds
3 Baths
Temple Estates SubDv.
32789 Zip Code

1621 Lasbury Avenue, Winter Park $1,089,000

Welcome to this stunning contemporary home located in Comstock Park, in the heart of Winter Park. This modern residence offers 3 bedrooms, 3 bathrooms, and an oversized, ...

3 Beds
3 Baths
Comstock Park SubDv.
32789 Zip Code

122 Scottsdale Square Unit 122, Winter Park image

122 Scottsdale Square Unit 122, Winter Park — 122 $139,786

Partially renovated large 3 bedroom and 2 full baths. Recently painted inside. One bath with new with new vanity, new electric fixtures, new plumbing and new toilet. Come...

3 Beds
2 Baths
Winter Park Woods Condo SubDv.
32792 Zip Code

1135 Lakeview Drive, Winter Park $5,200,000

Amazing opportunity to own a lakefront home on Lake Virginia footsteps from Rollins College, nestled in walking distance to downtown Park Avenue shops and restaurants, an...

5 Beds
4.5 Baths
Virginia Heights SubDv.
32789 Zip Code

204 Lewfield Circle Unit 204, Winter Park image

204 Lewfield Circle Unit 204, Winter Park — 204 $223,000

Welcome to the epitome of modern living! Step into this newly listed two bedroom two bath condominium in historic Winter Park and be greeted by freshly painted walls that...

2 Beds
2 Baths
Stratford A Winter Park Condo SubDv.
32792 Zip Code

7427 Grand Avenue, Winter Park $439,990

Charming Newly Remodeled Home with Modern Touches and Ample Outdoor Space Discover the perfect blend of comfort and style in this beautifully remodeled home, offering an...

4 Beds
2 Baths
Woodcrest Unit 5 SubDv.
32792 Zip Code

1181 Via Capri, Winter Park $1,895,000

Welcome to the sought after Winter Park “Vias”! Renovate or build your dream home on this incredible lot situated on a beautiful brick street within walking distance to t...

3 Beds
3 Baths
Cloister Grove Sub SubDv.
32789 Zip Code

2955 Lolissa Lane, Winter Park $1,000,000

Welcome to The Hills of Winter Park in the secluded enclave of Howell Forest. New updates include roof replacement (June 2023) remodeled kitchen featuring Kenmore 42" ra...

4 Beds
3 Baths
Howell Forest SubDv.
32789 Zip Code

1108 N New York Avenue, Winter Park image

1108 N New York Avenue, Winter Park $3,125,000

Quintessential Downtown Winter Park home with all of the character and amenities that make this lifestyle so sought -after. Well designed floor plan combines expansive op...

4 Beds
4.5 Baths
Valencia Terrace SubDv.
32789 Zip Code

4950 Tangerine Avenue Unit 4950, Winter Park image

4950 Tangerine Avenue Unit 4950, Winter Park — 4950 $279,000

Immerse yourself in the charm of Winter Park living in this lovely 3-bedroom, 2-bathroom condo that offers the perfect blend of comfort and location. At the dead end of t...

3 Beds
2 Baths
Wrenwood Condo SubDv.
32792 Zip Code

200 Saint Andrews Boulevard Unit 3610, Winter Park image

200 Saint Andrews Boulevard Unit 3610, Winter Park — 3600 $250,000

CLOSE TO EVERYTHING, yet tucked away in a private, sought after community conveniently located in breathtaking Winter Park. Enjoy the benefits of a peaceful and friendly ...

2 Beds
1.5 Baths
Four Seasons Condo SubDv.
32792 Zip Code

2083 Leanne Court, Winter Park $444,999

Welcome home! This cozy single-family house just got a makeover and is located in a quiet cul-de-sac with plenty of room for trailers, RVs and boat parking. It's got a ne...

3 Beds
2 Baths
Eastbrook Sub Unit 15 SubDv.
32792 Zip Code

1741 Laurel Road, Winter Park $1,499,900

Luxurious custom pool home in highly desired Winter Park on a beautiful brick street with mature trees! From the moment you walk into the grand entry, you will see that ...

4 Beds
3 Baths
Charmont SubDv.
32789 Zip Code

147 S Interlachen Avenue Unit 400, Winter Park image

147 S Interlachen Avenue Unit 400, Winter Park — 1 $3,850,000

Luxury lock & leave living from 147 S Interlachen Ave. This penthouse is a four-bedroom, 4.5 bath two-story condominium home in the heart of downtown Winter Park overlook...

4 Beds
4.5 Baths
147 Interlachen Place SubDv.
32789 Zip Code

3328 Raiders Run, Winter Park $457,500

WINTER PARK POOL HOME! GO ALL THE WAY TO THE END OF RAIDERS RUN AND THIS BEAUTIFUL HOME SITS ON THE END OF THE HALF CUL DE SAC WITH NO NEIGHBORS BEHIND YOU! WALK INTO THE...

3 Beds
2 Baths
Georgetown Estates SubDv.
32792 Zip Code

5421 Albert Drive, Winter Park $439,000

Welcome to your dream home in Winter Park! This stunning property boasts a complete renovation, offering you a fresh start with brand new features throughout. New roof, n...

3 Beds
2 Baths
Howell Branch Woods SubDv.
32792 Zip Code

200 Saint Andrews Boulevard Unit 3106, Winter Park image

200 Saint Andrews Boulevard Unit 3106, Winter Park — 3106 $275,000

Welcome Home! This beautiful 2 bedroom condo is move-in ready and can be sold furnished. It's the perfect living space along with an incredible fenced outdoor patio for y...

2 Beds
1.5 Baths
Four Seasons Condo SubDv.
32792 Zip Code

200 Saint Andrews Boulevard Unit 2703, Winter Park image

200 Saint Andrews Boulevard Unit 2703, Winter Park — 2700 $229,000

Welcome to the Four Seasons Condos in the City of Winter Park. This spacious 2 bed 2 bath 2nd floor 1127 sq. ft. end unit awaits your signature style. Upon entering the c...

2 Beds
2 Baths
Four Seasons Condominiums Of Winter Park SubDv.
32792 Zip Code

1436 Tangerine Court, Winter Park $330,000

***Investor Special***CASH ONLY***Come check out this 3-bedroom, 2-bath home conveniently located in Winter Park. Property needs some TLC and updating. Buyer is responsi...

3 Beds
2 Baths
Eastbrook Sub Unit 06 SubDv.
32792 Zip Code

7320 Beacon Place, Winter Park $460,000

Winter Park POOL HOME at the end of a quiet CUL-DE-SAC on a large .30 ACRE LOT with a NEW ROOF (2022), UPDATED PLUMBING (2023), NEW IRRIGATION SYSTEM (2023), ADDED 1-CAR ...

3 Beds
2 Baths
Oakcrest-516 SubDv.
32792 Zip Code

4457 Steed Terrace, Winter Park $619,000

Welcome to your dream home in the desirable Kings Cove subdivision of Winter Park! As you approach the front entryway, you're greeted by a grand walkway framed by large b...

4 Beds
3 Baths
Kings Cove SubDv.
32792 Zip Code

3651 N Goldenrod Road Unit 205, Winter Park image

3651 N Goldenrod Road Unit 205, Winter Park — E $205,000 ▲

Newly remodeled 2 bedroom/2 bathroom condo located in Lancelot of Winter Park. This spacious second floor unit with large windows brings in plenty of natural light. The ...

2 Beds
2 Baths
Lancelot/Winter Park SubDv.
32792 Zip Code

1250 Via Capri, Winter Park $1,895,000

In the heart of The Vias, this Mediterranean masterpiece encompasses 3,217 square feet of beauty and elegance for your enjoyment of living. Dating back to 1953, this icon...

3 Beds
3 Baths
Cloister Grove Sub SubDv.
32789 Zip Code

1350 Lyndale Boulevard, Winter Park image

1350 Lyndale Boulevard, Winter Park $1,850,000

Step into a world of unmatched luxury and meticulous detail in this stunning custom-built home located in the heart of Winter Park. This home spans two levels of exquisit...