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219 Properties Available
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- Newest Listings
- Beds (Most)
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$1,500,000
Single Family Home
1741 PINE AVE, Winter Park, FL 32789
Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool home offers the perfect balance of eleganc...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,295,000
Single Family Home
1932 TEMPLE DR, Winter Park, FL 32789
Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street is full of natural light, clean line...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,895,000
Single Family Home
817 ANTONETTE AVE, Winter Park, FL 32789
Iconic Winter Park treasure! Welcome home to 817 Antonette, an architecturally inviting residence that exudes quality an...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,850,000
Single Family Home
1470 PLACE PICARDY, Winter Park, FL 32789
Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$2,000
Single Family Home
1433 INDIANA AVE, Winter Park, FL 32789
1/2 Duplex in amazing location in Winter Park! Walk to great bars and restaurants or bike to Park Avenue! Full gut renov...
Listed by SAND DOLLAR REALTY GROUP INC
$649,000
Townhouse
735 MARYLAND AVE, Winter Park, FL 32789
Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming fo...
Listed by FANNIE HILLMAN & ASSOCIATES
$1,695
Single Family Home
657 MINNESOTA AVE, Winter Park, FL 32789
DUPLEX - FANTASTIC WINTER PARK LOCATION. 2 bedroom, 1 bath, with carport on driveway.. PRIVATE FENCED BACKYARD!! Terrazz...
Listed by A+ HOME RENTALS LLC
$1,750
Condo
1250 S DENNING DR #130, Winter Park, FL 32789
Great Location & Available 05/15/25! Beautiful Condo for Rent at the Mead Garden in Winter Park. Spacious 2 Bedroom and ...
Listed by FLORIDA TOP REALTY
$3,500,000
Single Family Home
443 LAKEWOOD DR, Winter Park, FL 32789
This single-story home offers serene lakefront living with approximately 95 feet of prime water frontage on beautiful La...
Listed by FANNIE HILLMAN & ASSOCIATES
$949,000
Condo
100 S INTERLACHEN AVE #502D, Winter Park, FL 32789
Under contract-accepting backup offers. Top floor direct lakefront view of this Renovated condominium. Professional pict...
Listed by COLDWELL BANKER RESIDENTIAL RE
$145,000
Condo
1695 LEE RD #E205, Winter Park, FL 32789
Looking for an affordable home in a prime location? This budget-friendly 2-bedroom, 1-bath condo is move-in ready! Fresh...
Listed by KELLER WILLIAMS HERITAGE REALTY
$2,700
Condo
350 CAROLINA AVE #407, Winter Park, FL 32789
This top floor 2/2 condo has vaulted ceilings, stainless steel appliances, quartz counters and hardwood floors. There ar...
Listed by KELLER WILLIAMS REALTY AT THE PARKS
$889,990
Townhouse
1429 INDIANA AVE, Winter Park, FL 32789
Welcome to this stunning 3-bedroom, 2.5-bathroom townhome located in the highly sought-after Winter Park, just minutes a...
Listed by KELLER WILLIAMS WINTER PARK
$1,575,000
Condo
690 OSCEOLA AVE #604, Winter Park, FL 32789
Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder's unit with panoramic views of Lake Virginia from almos...
Listed by COLDWELL BANKER RESIDENTIAL RE
$4,875,000
Single Family Home
229 ALEXANDER PL, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Discover a stunning blend of modern luxury and award-winning design in t...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$2,595
Single Family Home
2351 WESTMINSTER CT, Winter Park, FL 32789
This 3 bedroom, 2 bathroom home is located on a quiet street in Winter Park. Enjoy all Downtown Winter Park has, Park Av...
Listed by REAL PROPERTY MANAGEMENT AND REALTY
$4,799,900
Single Family Home
1691 CHESTNUT AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini C...
Listed by COMPASS FLORIDA LLC
$4,600,000
Single Family Home
2118 LAKE DR, Winter Park, FL 32789
"The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a p...
Listed by COMPASS FLORIDA LLC
$429,900
Single Family Home
1975 STAUNTON AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Welcome to this charming 3-bedroom, 2-bathroom Winter Park home. The co...
Listed by ABSOLUTE REALTY GROUP, LLC
$2,800,000
Condo
315 E NEW ENGLAND AVE #30, Winter Park, FL 32789
Under contract-accepting backup offers. Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthou...
Listed by COLDWELL BANKER REALTY
$1,799,000
Single Family Home
1731 WINDSOR DR, Winter Park, FL 32789
Welcome to 1731 Windsor - this unique freshly renovated luxury home is on an oversized lot in charming & beautiful Winte...
Listed by CHARLES RUTENBERG REALTY ORLANDO
$669,000
Single Family Home
2739 RIDDLE DR, Winter Park, FL 32789
Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, a...
Listed by BRAINARD REALTY
$12,000
Single Family Home
851 VIRGINIA DR, Winter Park, FL 32789
Welcome to this stunning furnished pool home in the desirable Audubon Park School District. Thoughtfully designed with a...
Listed by PREMIER SOTHEBY'S INTL. REALTY
$1,580,000
Single Family Home
1750 WINCHESTER DR, Winter Park, FL 32789
Nestled within Winter Park's coveted Timberlane Shores is this light, airy, expertly renovated abode that exudes comfort...
Listed by FANNIE HILLMAN & ASSOCIATES