-
- My Homes
- My Tours
- My Favorites
- My Searches
- Sign In
- Register
- 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
222 Properties Available
- Default
- Price-High To Low
- Price-Low To High
- Newest Listings
- Beds (Most)
- Baths (Most)
- Year Built (Newest)
- Square Feet (Biggest)
$1,800
Condo
1512 INDIANA AVE #C, Winter Park, FL 32789
Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$11,900,000
Single Family Home
1120 PRESERVE POINT DR, Winter Park, FL 32789
Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean Estate i...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,295,000
Single Family Home
433 CAROLINA AVE, Winter Park, FL 32789
From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gour...
Listed by COLDWELL BANKER RESIDENTIAL RE
$1,275,000
Single Family Home
1611 WALNUT AVE, Winter Park, FL 32789
One of the most peaceful, sought-after areas of Old Winter Park is located off Palmer Ave in Lk Knowles Terrace, just st...
Listed by COLDWELL BANKER RESIDENTIAL RE
$365,000
Single Family Home
770 CARVER ST, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome to 770 Carver Street in the highly sought after Winter Park, Florida! <b...
Listed by LEGENDS REALTY
$140,000
Condo
1695 LEE RD #B211, Winter Park, FL 32789
Fantastic 2 bedroom, 1 bathroom unit in the centrally located Waterfall Cove community in Winter Park, close to all of t...
Listed by RE/MAX ASSURED
$1,450
Single Family Home
1512 INDIANA AVE #B, Winter Park, FL 32789
Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV
$2,200
Condo
151 N ORLANDO AVE #207, Winter Park, FL 32789
Welcome to this beautifully renovated 2-bedroom, 1-bathroom second-floor condo on picturesque Lake Killarney. This move-...
Listed by PALMANO GROUP RE BROKERAGE LLC
$1,450
Single Family Home
1512 INDIANA AVE #A, Winter Park, FL 32789
Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and din...
Listed by LAWHUN ENTERPRISES IV, LLC DBA:FLORIDA REALTY INVESTMENTS IV
$5,800,000
Single Family Home
541 VIRGINIA DR, Winter Park, FL 32789
*Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is pric...
Listed by HOMEVEST REALTY
$395,000
Single Family Home
2827 EUSTON RD, Winter Park, FL 32789
Welcome to 2827 Euston Rd, a beautifully updated home in the highly desirable Winter Park area with the added bonus of n...
Listed by REGENCY REAL ESTATE LLC
$235,000
Condo
1500 GAY RD #7A, Winter Park, FL 32789
Seller to replace windows or give a credit to buyer at closing!!! Discover unparalleled comfort in this stunning 2-bed, ...
Listed by PRISTINE FLORIDA PROPERTIES LLC
$599,000
Townhouse
1392 INDIANA AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Nestled in the heart of Winter Park, this stunning two-story townhome seamlessly...
Listed by COLDWELL BANKER RESIDENTIAL RE
$1,980
Condo
250 CAROLINA AVE #307, Winter Park, FL 32789
Spacious 1 Bedroom 2 bathroom condo in Beautiful ParkWest in Winter Park, walking distance to Park Ave. 3rd floor unit, ...
Listed by VERANDA PARK REALTY LLC
$449,990
Single Family Home
1550 INDIANA AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Discover the charm of this beautiful 3-bedroom home in the heart of Winter Park,...
Listed by TALENT REALTY SOLUTIONS
$350,000
Condo
184 SANDLEWOOD TRL #2, Winter Park, FL 32789
Presenting a gorgeous, completely renovated condo with a townhome feel, available in highly desirable Winter Park. This ...
Listed by SAVVY AVENUE, LLC
$5,490
Condo
782 S PENNSYLVANIA AVE #1, Winter Park, FL 32789
Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light,...
Listed by BEYCOME OF FLORIDA LLC
$1,100,000
Single Family Home
708 BALMORAL RD, Winter Park, FL 32789
Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 708 Balmoral Road, lo...
Listed by FANNIE HILLMAN & ASSOCIATES
$695,000
Single Family Home
786 ANTONETTE AVE, Winter Park, FL 32789
FIRST TIME OFFERING! Charming Bungalow in the heart of Winter Park. 50' x 150' lot offers limitless possibilities! Conv...
Listed by RE/MAX 200 REALTY
$8,799,000
Single Family Home
2661 VIA TUSCANY, Winter Park, FL 32789
CALLING HIGHEST AND BEST BY 4/30/2025!! <br> <br>Introducing a Unique, Stunning Modern Home <br> <br>A groundbreaking a...
Listed by PV LUXURY GROUP PA
$205,000
Condo
1695 LEE RD #B216, Winter Park, FL 32789
Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaura...
Listed by RE/MAX ASSURED
$189,900
Condo
1250 S DENNING DR #122, Winter Park, FL 32789
One or more photo(s) has been virtually staged. **MAJOR PRICE DROP** FANTASTIC OPPORTUNITY** <br>Discover the perfect b...
Listed by ORLANDO HOME DEALER LLC
$2,700
Condo
151 N ORLANDO AVE #131, Winter Park, FL 32789
Enjoy lakefront living in this 2-bedroom, 1-bath end-unit condo in Lake Killarney Condos. Located on private, navigable ...
Listed by FLORIDA DREAMS REALTY GRP INC
$1,599,999
Single Family Home
1429 CHAPMAN CIR, Winter Park, FL 32789
Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophistica...
Listed by CORCORAN PREMIER REALTY