- Home
- General
- Buyer
- All Listings
- Featured Listings
- Sold Listings
- 50 Homes For 50 Fallen
- 10 Best Buy Hotlist
- 13 Extra Cost
- 6 Buyer Mistakes
- 9 Common Buyer Traps
- Ask a Real Estate Expert
- Best Financing Rate
- Buy With Zero Down
- First Time Buyer Hotlist
- Exclusive Fixer Upper Hotlist
- Fixer Uppers: Myths and Facts
- Foreclosures Hotlist
- Get New Listings
- Home Warranty
- Homes with Land Hotlist
- Homes with Pools Hotlist
- Hotlist of Upscale Homes
- Mortgage Pre-Approval
- Moving Company
- Moving Up
- Multiple Listing
- New Homes vs Resale
- No Money Down Hotlist
- Open House
- Our Homes for Sale
- Real Estate Lawyer
- Save $5000 Guaranteed
- Save Thousands
- Stop Paying Rent
- Sunday Tour of Homes
- VIP INSIDER ACCESS
- Seller
- Sell My Home
- Home Estimate
- 10 Questions Agents Hate
- 27 Seller Tips
- Avoid Legal Mistakes
- Avoid these mistakes
- Become a VIP Seller
- Buy This Home Ill Buy Yours
- Cash For your Home
- Divorce
- Empty Nesting
- Find Out What This Home Is Sold For
- For Sale By Owner
- Getting Best Price
- Get the Price You Want
- Guaranteed Offer
- How to Sell a Home that Didnt Sell
- How to Sell Your Home for More
- Kids and Moving
- Pets and Moving
- Pass Your Inspection
- Why Didnt My Home Sell
- Neighborhoods
- About
- Market Snapshot
- MORE
- Register
- Sign In
488 Properties Available In Winter Park
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$3,299,000
Single Family Home
255 STIRLING AVE, Winter Park, FL 32789
An incredible Winter Park Chain of Lakes opportunity on Lake Virginia with clear views of Rollins College. This transiti...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$699,000
Single Family Home
2825 MULFORD AVE, Winter Park, FL 32789
Welcome to 2825 Mulford Avenue, 'Memorable Mulford,' a charming 2-bedroom, 2-bath bungalow ideally located in Winter Par...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$430,000
Single Family Home
5122 N WOODCREST DR, Winter Park, FL 32792
This is your chance to own a rare updated 3-bedroom, 2-bath pool home in the heart of Winter Park. This move-in-ready p...
Listed by KELLER WILLIAMS ELITE PARTNERS III REALTY
$2,100,000
Single Family Home
1540 PALM AVE, Winter Park, FL 32789
Welcome to this stunning SINGLE STORY five-bedroom home in one of Winter Park's most desirable neighborhoods, where char...
Listed by FANNIE HILLMAN & ASSOCIATES
$3,495,000
Single Family Home
1821 ENGLEWOOD RD, Winter Park, FL 32789
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Developmen...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,650,000
Single Family Home
340 ALBERTA DR, Winter Park, FL 32789
Welcome to 340 Alberta Drive, a beautifully maintained 4-bedroom, 4-bath residence with a new roof installed in 2020. Si...
Listed by REAL ESTATE FIRM OF ORLANDO
$1,075,000
Single Family Home
2143 BLOSSOM LN, Winter Park, FL 32789
Winter Park canal front with direct access to Lake Killarney. <br> <br>This 3-bed, 2-bath, split-plan home blends everyd...
Listed by EXP REALTY LLC
$425,000
Single Family Home
5422 ALBERT DR, Winter Park, FL 32792
Welcome home to 5422 Albert Drive this beautifully remodeled 3-bedroom, 2-bathroom home is located in the heart of Winte...
Listed by WATSON REALTY CORP
$575,000
Single Family Home
1875 STAUNTON AVE, Winter Park, FL 32789
Welcome to this newer single-family home tucked away in the Karolina On Killarney section of Winter Park. Situated on a ...
Listed by KELLER WILLIAMS WINTER PARK
$373,500
Single Family Home
5110 N WOODCREST DR, Winter Park, FL 32792
Discover the perfect blend of comfort and convenience in this beautifully remodeled 3-bedroom, 2-bath home in Winter Par...
Listed by LA ROSA REALTY ORLANDO LLC
$1,165,000
Single Family Home
1450 CHESTNUT AVE, Winter Park, FL 32789
Located in the coveted Tree Streets just a block and a half from Lake Knowles, this timeless Mediterranean home offers t...
Listed by KELLY PRICE & COMPANY LLC
$375,000
Single Family Home
2320 HIGH ST, Winter Park, FL 32792
One or more photo(s) has been virtually staged. Enjoy a 1% lower interest rate for your first year with our preferred le...
Listed by THE AGENCY ORLANDO
$1,050,000
Single Family Home
7706 WAUNATTA CT, Winter Park, FL 32792
Stunning Lakefront Retreat in Winter Park! Welcome to your dream home on beautiful Lake Waunatta! This spacious and upgr...
Listed by SAND DOLLAR REALTY GROUP INC
$535,000
Single Family Home
240 ORANGE TERRACE DR, Winter Park, FL 32789
DON'T MISS OUT! <br>Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath ...
Listed by A+ REALTY PROFESSIONALS, INC
$980,000
Single Family Home
208 BREWER AVE, Winter Park, FL 32789
SELLERS ARE OFFERING A $5,000 CREDIT TO A BUYER FOR AN ACCEPTED CONTRACT BY 09/30/25! Welcome to this beautifully update...
Listed by COMPASS FLORIDA LLC
$599,500
Townhouse
1250 FORMOSA AVE, Winter Park, FL 32789
Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after...
Listed by RE/MAX TOWN & COUNTRY REALTY
$995,000
Townhouse
512 CLARENDON AVE, Winter Park, FL 32789
Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins Colle...
Listed by COMPASS FLORIDA LLC
$349,000
Single Family Home
1516 PINEWOOD DR, Winter Park, FL 32789
PINEWOOD SUB N/9 LOT 12 BLK A <br> <br> <br>Well-maintained, modest 2-1 home in College Park with carport, deck, and por...
Listed by LIST NOW REALTY, LLC
$1,695,000
Single Family Home
1270 ARLINGTON PL, Winter Park, FL 32789
Modern Elegance in the Heart of Winter Park! <br> <br>Located just a half-mile from the renowned shops and dining of Par...
Listed by RE/MAX 200 REALTY
$499,000
Single Family Home
2844 SCARLET RD, Winter Park, FL 32792
Welcome to this stunning mid-century modern beauty where timeless design meets thoughtful, contemporary updates. Nestled...
Listed by KELLER WILLIAMS WINTER PARK
$1,899,000
Single Family Home
617 WORTHINGTON DR, Winter Park, FL 32789
WINTER PARK FIVE BEDROOM POOL HOME - Discover luxurious living in the heart of Winter Park! Crafted with exquisite atten...
Listed by KELLY PRICE & COMPANY LLC
$5,495,000
Single Family Home
2211 AZALEA PL, Winter Park, FL 32789
Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront...
Listed by FORTUNE INTERNATIONAL REALTY
$2,300,000
Single Family Home
1781 PINE AVE, Winter Park, FL 32789
Price Reduced to sell. An exceptional custom home by award-winning Davila Homes, perfectly blending modern design and fu...
Listed by FLORIDA CONNEXION PROPERTIES
$455,000
Single Family Home
2648 AMSDEN RD, Winter Park, FL 32792
Beautiful Pool Home in Desirable Winter Park Estates. Seller is Motivated. <br>Welcome to this charming and thoughtfull...
Listed by CHOICEPOINTE REALTY, INC.