Comprehensive real estate search in the Winter Park area. We have over 1,619 listings to browse so you can find your perfect home. Whether you are looking through our 843 MLS properties, 17 for sale by owner, 748 foreclosures — you're sure to find your next property with Roost.com.





See all homes by builder and community. View both planned and spec real estate properties including their floor plans. Here is a sample of our listings...





We've gathered For Sale By Owner listings for you. Filter them by price, bed bath, neighborhood, school district and more. Here are just a few of our FSBO listings...
We have one of the best collections of foreclosure listings available! Filter them by status: Default, Auction or Bank Owned.
Congratulations! You are about to set out on the exciting journey the road to home ownership. Our Winter Park homes for sale and MLS listings are the most comprehensive available. You can search Roost.com for all your real estate needs; including Multiple Listing Service ( MLS ) properties for sale; homes for sale by owner (FSBO); new construction listings and foreclosures / foreclosed properties.
There are approximately 727 residential MLS listings available having an average price of $574,642. Popular neighborhoods include: Winter Park, Goldenrod and Fairview Shores. If you have children, you may be interested in homes for sale in these school districts: Orange County and Seminole County. Streets with the most MLS listings include: E Morse Blvd, Aloma Ave and Lewfield Cir.
Are you looking for tangible features or are you looking for a home in the Winter Park MLS that just feels right? Start with the basics like number of beds and baths then use our intuitive filters to zero in on homes for sale by neighborhood or school district. You can even search for amenities such as pool, remodeled kitchen, hardwood and more! Roost is the perfect search for your perfect home.
| Avg Price | Price/Sq Ft | 0-250k | 251-500k | 501-750k | 751-1M | 1M+ | |
|---|---|---|---|---|---|---|---|
| MLS Listings | $544,477 | $195 | 363 | 167 | 75 | 49 | 102 |
| For Sale By Owner | $524,014 | $186 | 4 | 0 | 1 | 1 | 1 |
| New Homes | $162,313 | $93 | 11 | 0 | 0 | 0 | 0 |
| Foreclosure | $913,368 | $167 | 128 | 4 | 0 | 1 | 1 |
Search all of our recent sold information and compare them to homes on the MLS
| Address | City | Price | Beds | Baths | Sq.Ft | Date Sold |
|---|---|---|---|---|---|---|
| 401 WORTHINGTON DR | WINTER PARK | $400,000 | 3 | 2 | 1,900 | 08/03/2009 |
| 1409 CHAPMAN CIR | WINTER PARK | $650,000 | 3 | 3 | 1,400 | 07/31/2009 |
| 716 FRIAR RD | WINTER PARK | $275,000 | 3 | 2 | 1,700 | 07/31/2009 |
| 910 N PHELPS AVE | WINTER PARK | $425,000 | 4 | 3 | 2,000 | 07/31/2009 |
| 2022 EASTBROOK BLVD | WINTER PARK | $168,000 | - | 3 | 1,200 | 07/30/2009 |
| 259 RIPPLING LN | WINTER PARK | $1,000,000 | 4 | 3 | 2,700 | 07/30/2009 |
| 712 MONMOUTH WAY | WINTER PARK | $245,000 | 4 | 3 | 2,400 | 07/29/2009 |
| 2000 TEMPLE DR | WINTER PARK | $685,000 | 5 | 1 | 700 | 07/28/2009 |
| MLS Listings | 843 |
| New Construction | 11 |
| For Sale by Owner | 17 |
| Foreclosures | 748 |
| Total Listings | 1,619 |
Search all of our recent sold information and compare them to homes on the MLS





Most real estate sites rely on individuals to upload their own listings. This usually results in a fragmented and partial view of what homes are truly available for sale. Even worse, it often means stale info. We partner with the local "Multiple Listing Services" ( MLS ) and local real estate brokers in Winter Park to ensure you have access to not only the most complete, but also the most up-to-date homes for sale available.