- 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
- Any
- $ 100,000
- $ 150,000
- $ 200,000
- $ 400,000
- $ 800,000
- Any
- $ 200,000
- $ 300,000
- $ 400,000
- $ 600,000
- $ 1,000,000
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
- Any
- 1
- 2
- 3
- 4
- 5
491 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)
$1,749,000
Condo
101 S NEW YORK AVE #311, Winter Park, FL 32789
Discover luxury living in this exquisite two-story condominium, located on the third floor of the highly sought-after Do...
Listed by KELLY PRICE & COMPANY LLC
$585,000
Single Family Home
2441 BANCHORY RD, Winter Park, FL 32792
Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the highly desirable Brookshire Heights neighborhood...
Listed by FANNIE HILLMAN & ASSOCIATES
$459,999
Single Family Home
5326 LANYARD CT, Winter Park, FL 32792
Discover your dream home in Winter Park! This stunning 3-bedroom, 2-bathroom gem sits on a spacious 1/3-acre lot, offeri...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$1,275,000
Single Family Home
309 PARK NORTH CT, Winter Park, FL 32789
Endless Potential in the Heart of Park North! <br>Just steps from the charm and energy of Winter Park's Park Avenue—wher...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,165,000
Single Family Home
2832 BEAR ISLAND POINTE, Winter Park, FL 32792
Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cypress Reserve! This meticulously maintain...
Listed by COMPASS FLORIDA LLC
$1,025,000
Single Family Home
2923 COVE TRL, Winter Park, FL 32789
A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILITY & RESORT-STYLE Living comes to market ...
Listed by KELLER WILLIAMS ADVANTAGE III
$975,000
Single Family Home
1265 PARK POINTE LN, Winter Park, FL 32789
Welcome home to this beautifully upgraded gem nestled in the heart of Winter Park. This move-in-ready home sits on a qui...
Listed by KELLER WILLIAMS ADVANTAGE III
$800,000
Single Family Home
600 BRECHIN DR, Winter Park, FL 32792
Welcome to one of the most sought after neighborhoods of Kenilworth Shores in Winter Park! Nestled among tree-lined stre...
Listed by KELLER WILLIAMS WINTER PARK
$498,000
Single Family Home
808 DENTON RD, Winter Park, FL 32792
Step into a slice of mid-century magic, your private oasis awaits. On an oversized corner lot with no rear neighbors, th...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,150,000
Single Family Home
795 W CANTON AVE, Winter Park, FL 32789
Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and...
Listed by WEICHERT REALTORS HALLMARK PROPERTIES
$2,575,000
Single Family Home
1795 GREENWICH AVE, Winter Park, FL 32789
Welcome to a one-of-a-kind, custom-designed residence offering the perfect blend of modern sophistication, thoughtful fu...
Listed by KELLY PRICE & COMPANY LLC
$1,299,000
Single Family Home
1341 LYNDALE BLVD, Winter Park, FL 32789
Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park V...
Listed by COMPASS FLORIDA LLC
$2,295,000
Single Family Home
2614 PARKLAND DR, Winter Park, FL 32789
Welcome to 2614 Parkland Drive—an exquisite, fully renovated luxury residence nestled in the heart of Winter Park, Flori...
Listed by JW GASTON LLC
$1,550,000
Single Family Home
1661 WOODLAND AVE, Winter Park, FL 32789
Fabulous Top-to-Bottom Renovation on Coveted Brick Street in Prime Winter Park Location! This exceptional 3-bedroom, 3.5...
Listed by FANNIE HILLMAN & ASSOCIATES
$525,000
Single Family Home
3306 FISHERMANS CV, Winter Park, FL 32792
Beautiful home is the sought-after community of Pelican Bay in Winter Park. Pelican Bay only has 48 homes in the communi...
Listed by WEICHERT REALTORS HALLMARK PROPERTIES
$569,999
Single Family Home
7730 BROKEN ARROW TRL, Winter Park, FL 32792
Welcome to this inviting 3-bedroom, 2-bathroom home, perfectly situated on a spacious lot that offers peace, privacy, an...
Listed by LA ROSA REALTY PREMIER LLC
$1,200,000
Condo
100 S INTERLACHEN AVE #304, Winter Park, FL 32789
Sit back and relax on two private balconies with pool and lake views. This combined unit has the largest square footage ...
Listed by FANNIE HILLMAN & ASSOCIATES
$349,990
Single Family Home
320 GRANADA DR, Winter Park, FL 32789
Welcome to this delightful 3-bedroom, 2-bathroom home nestled in the heart of sought-after Winter Park! Bursting with ch...
Listed by KELLER WILLIAMS WINTER PARK
$639,000
Condo
100 S INTERLACHEN AVE #107F, Winter Park, FL 32789
Welcome to the heart of Winter Park living! This beautifully updated 2 bedroom, 1 bath, first floor condo offers the per...
Listed by MAINFRAME REAL ESTATE
$675,000
Single Family Home
796 MCINTYRE AVE, Winter Park, FL 32789
Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home,...
Listed by FANNIE HILLMAN & ASSOCIATES
$479,900
Single Family Home
1532 LAWNDALE CIR, Winter Park, FL 32792
Welcome to Your Florida Oasis in Winter Park! <br> <br>This beautifully maintained 4-bedroom, 3-bathroom home offers 2,0...
Listed by KELLER WILLIAMS WINTER PARK
$575,000
Single Family Home
2007 STRATHAVEN ROAD, Winter Park, FL 32792
Updated, immaculate and move-in ready! You'll love everything about this 4BR classic ranch style home in Kenilworth Shor...
Listed by EXP REALTY LLC
$385,000
Single Family Home
5144 ORANGE AVE, Winter Park, FL 32792
One or more photo(s) has been virtually staged. PRICED TO SELL! NEW ROOF, UPDATED PANEL BOX, UPDATED KITCHEN. Welcome Ho...
Listed by WEMERT GROUP REALTY LLC
$349,000
Single Family Home
3204 NETHERWOOD, Winter Park, FL 32792
Discover this beautifully renovated 2-bedroom, .5 -bathroom villa in the heart of Winter Park! Nestled on a private cul-...
Listed by WATSON REALTY CORP.