Winter Park Homes for Sale

Latest Winter Park Homes and Condos for Sale

265 Scottsdale Square Unit 265, Winter Park image

265 Scottsdale Square Unit 265, Winter Park — K $120,000

A must see. Two bedroom two bath located on the first floor. Winter Park Location close to Full Sail University, UCF, Valencia and more. Close to the Orlando Internatio...

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

2615 Ambergate Road, Winter Park $369,000

Great opportunity to own a spacious home in the Winter Park Estates neighborhood. This property can be utilized as a 4-bedroom, 3-bathroom home, or a 3-bedroom, 2-bathroo...

4 Beds
3 Baths
Winter Park Estates SubDv.
32792 Zip Code

2931 Summerfield Road, Winter Park image

2931 Summerfield Road, Winter Park $399,000

Short Sale. Short Sale. Presenting a fabulous opportunity to own a home right across the street from Winter Pines Golf Club, and to live in coveted Winter Park, known for...

4 Beds
2 Baths
Golfside Sec 03 SubDv.
32792 Zip Code

110 Chelton Circle, Winter Park $1,850,000

This quintessential Winter Park home was built up on a 0.44-acre corner lot hill, surrounded by brick streets, overlooking Lake Chelton. Built in 1951, it has been expand...

4 Beds
4 Baths
Forest Hills SubDv.
32789 Zip Code

1860 Biscayne Drive, Winter Park $280,000

Sold for land value with many new construction and renovated homes in the area. Few blocks away are Million dollar plus water front homes. Lots of commercial developmen...

Karolina On Killarney SubDv.
32789 Zip Code

250 Carolina Avenue Unit 402, Winter Park image

250 Carolina Avenue Unit 402, Winter Park — 250 $535,000

Gorgeous Winter Park condo with a NYC loft feeling and million-dollar views, and just steps from Park Avenue! Rare opportunity to own a large TOP floor unit in the perfe...

2 Beds
2 Baths
Park West Condo SubDv.
32789 Zip Code

2322 Woodcrest Drive, Winter Park $600,000

New windows providing abundant light and added efficiency. Beautiful, fully renovated Winter Park home. Easy walk to Winter Park High School and close to both downtown Wi...

4 Beds
2 Baths
Kenilworth Estates 1st Add SubDv.
32792 Zip Code

2429 Passamonte Drive Unit 20, Winter Park image

2429 Passamonte Drive Unit 20, Winter Park — 20 $300,000

Here is your chance to own one of the most luxurious townhomes in the entire Via Lago community! This gorgeous home features a spacious, open floor plan with beautiful en...

3 Beds
2 Baths
Via Lago/Hanging Moss Ph 09 SubDv.
32792 Zip Code

1000 S Semoran Boulevard Unit 408, Winter Park image

1000 S Semoran Boulevard Unit 408, Winter Park — 2 $105,000

Great investment opportunity. Tenant occupied. Conveniently located to shopping and Full Sail and UCF. Spacious and updated villa with a NEW AC and Water Heater.

1 Beds
1 Baths
Golfside Villas Condo SubDv.
32792 Zip Code

1000 S Semoran Boulevard Unit 413, Winter Park image

1000 S Semoran Boulevard Unit 413, Winter Park — 2 $105,000

Great investment opportunity. Tenant occupied. Updated and spacious home with a NEW AC and Waterheater. Conveniently located to shopping and Full Sail and UCF.

1 Beds
1 Baths
Golfside Villas Condo SubDv.
32792 Zip Code

1000 S Semoran Boulevard Unit 306, Winter Park image

1000 S Semoran Boulevard Unit 306, Winter Park — 2 $105,000

Great investment opportunity. Tenant occupied. This spacious updated villa is overlooking the pool and possibly one of the most private units in the community. The villa ...

1 Beds
1 Baths
Golfside Villas Condo SubDv.
32792 Zip Code

1000 S Semoran Boulevard Unit 404, Winter Park image

1000 S Semoran Boulevard Unit 404, Winter Park — 2 $105,000

Great investment opportunity. Tenant occupied. Conveniently located to shopping and Full Sail and UCF. Updated and spacious Villa with a new AC and Water Heater.

1 Beds
1 Baths
Golfside Villas Condo SubDv.
32792 Zip Code

628 Penn Place, Winter Park $1,250,000

European charmer is located in the highly desired community of Pennsylvania Place (a total of 28 homes) and is walking distance from Park Avenues restaurants, shops, and...

4 Beds
3 Baths
Pennsylvania Place Rep SubDv.
32789 Zip Code

208 Brewer Avenue, Winter Park $750,000

A must see beautiful 4 bedroom 3 bathroom home in the heart of Winter Park. Minutes away from the renowned strip, Park Ave. Once you enter you are greeted by a welcoming ...

4 Beds
3 Baths
Cortland Park SubDv.
32789 Zip Code

629 Balfour Drive, Winter Park $589,000

This is the one! Welcome home to Winter Park in the beautiful tucked away neighborhood of Winter Park Estates! This stunning custom-built pool home includes 4 bedrooms, 2...

4 Beds
2 Baths
Winter Park SubDv.
32792 Zip Code

1773 Indiana Avenue Unit C, Winter Park image

1773 Indiana Avenue Unit C, Winter Park — Las Casas $415,000

This Mediterranean two story townhome feels welcoming and cozy and is full of high end finishes. When you enter the stately double arched wood entry doors, you will disco...

3 Beds
2 Baths
Las Casas De Indiana Condo SubDv.
32789 Zip Code

1644 Berkshire Avenue, Winter Park image

1644 Berkshire Avenue, Winter Park $385,000

CHARM, LOCATION, & CONVENIENCE! This well-cared for 2Bd/1Ba bungalow is located in the heart of Orwin Manor. Features include: hardwood floors, nice kitchen, living roo...

2 Beds
1 Baths
Orwin Manor Westminster Sec SubDv.
32789 Zip Code

300 Fountain Lane, Winter Park $459,000

Mid-Century pool home is now available in Winter Park with lake access to Lake Killarney! This home is made for entertaining with 3 bedrooms, 3 baths, and a backyard oasi...

3 Beds
3 Baths
Shores Lake Killarney Sec 02 SubDv.
32789 Zip Code

433 Lakeview Avenue, Winter Park $549,000

Enjoy views of Lake Killarney from this charming late 1940's 3/2 bungalow in Winter Park on a bricked street. Enter into a large living room that is light and spacious op...

3 Beds
2 Baths
Killarney Estates SubDv.
32789 Zip Code

1450 Gene Street, Winter Park $520,000

Amazing Location. Don't miss this Winter Park property before it is gone. Brand new interior paint. Why rent, when you can own this perfectly, located property. FREESTA...

3 Beds
3 Baths
Acreage & Unrec SubDv.
32789 Zip Code

737 N Capen Avenue, Winter Park $732,000

Step inside this one of kind, mid-century inspired beauty located in desirable Winter Park. This incredible BRAND NEW home features vaulted ceilings galore. Entering th...

3 Beds
2 Baths
Capens Add SubDv.
32789 Zip Code

200 Saint Andrews Boulevard Unit 401, Winter Park image

200 Saint Andrews Boulevard Unit 401, Winter Park — 200 $135,500

Welcome home to your first floor condominium in the sought after community of Four Seasons in breathtaking Winter Park. Location, location, location! This community is w...

1 Beds
1 Baths
Four Seasons Condo SubDv.
32792 Zip Code

317 Park North Court, Winter Park $1,375,000

WONDERFUL OPPORTUNITY TO OWN THIS NEWLY UPDATED HOME IN A HIGHLY DESIRABLE WINTER PARK NEIGHBORHOOD Zoned for A-rated Schools. A few minutes’ walk/bike ride to Park Ave ...

4 Beds
3 Baths
Park North SubDv.
32789 Zip Code

788 W New England Avenue, Winter Park image

788 W New England Avenue, Winter Park $330,000

Taking highest and best offers until Oct 26th! Have already received multiple offers. Welcome to one of the MOST SOUGHT after places in all of Central Florida!!! WINTE...

Winter Park SubDv.
32789 Zip Code

690 Osceola Avenue Unit 607, Winter Park image

690 Osceola Avenue Unit 607, Winter Park — Na $849,000

Move in today to 690 Osceola Ave, Unit #607, and wake up tomorrow to the views of Lake Virginia from your luxury 2-story penthouse with a private balcony and an abundance...