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59 Properties Available
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$1,070,000
Single Family Home
1611 CHESTNUT AVE, Winter Park, FL 32789
Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedro...
Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
$534,900
Townhouse
1261 INDIANA AVE, Winter Park, FL 32789
Tucked in the heart of Harper Place, this 3-bedroom, 2.5 bath end unit townhome 1,660 sq ft of light-filled, low mainten...
Listed by Megan Cross FANNIE HILLMAN & ASSOCIATES
$2,249,000
Single Family Home
2361 MULBRY DR, Winter Park, FL 32789
Newly completed and selected as a showcase residence in the 2026 Parade of Homes, Casa Noir is a custom-built statement ...
Listed by Ahmad Hassan, PA COMPASS FLORIDA LLC
$1,295,000
Condo
106 S INTERLACHEN AVE #118, Winter Park, FL 32789
Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot...
Listed by Drew Henner PREMIER SOTHEBY'S INTL. REALTY
$1,100,000
Single Family Home
241 W LAKE SUE AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Welcome to 241 W. Lake Sue Avenue, a rare offering in Virginia Heights, ...
Listed by Ken Dalton COLDWELL BANKER REALTY
$724,900
Single Family Home
860 N DENNING DR, Winter Park, FL 32789
**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** <br> <br>This is not a remodel — it's a comple...
Listed by LaDarrius Sanders OUTLET REALTY
$689,000
Single Family Home
2157 LAKE DR, Winter Park, FL 32789
Welcome to this beautifully maintained Winter Park home in coveted 32789, offering over 2,600 square feet, peekaboo Lake...
Listed by Jacob Johnson SHORES REAL ESTATE
$4,250
Townhouse
1119 S PENNSYLVANIA AVE, Winter Park, FL 32789
Welcome home to this beautifully updated Cherokee Park townhome, where modern elegance meets comfort in the heart of hig...
Listed by Raquel Elliott COLDWELL BANKER REALTY
$724,000
Single Family Home
2418 EUSTON RD, Winter Park, FL 32789
Welcome to this beautifully updated three-bedroom, two-and-a-half-bath home located in the highly sought-after Winter Pa...
Listed by Rick Bavec TOLARIS REALTY GROUP LLC
$687,000
Single Family Home
1707 HARMON AVE, Winter Park, FL 32789
A timeless blend of historic charm and modern luxury awaits in this beautifully restored 1927 Florida bungalow, nestled ...
Listed by Nicole Howell FANNIE HILLMAN & ASSOCIATES
$699,000
Single Family Home
2333 WESTMINSTER CT, Winter Park, FL 32789
Settled on a rare double lot in the heart of Winter Park, this 4-bedroom, 2-bath home delivers the Florida lifestyle you...
Listed by Ernest Middleton CHARLES RUTENBERG REALTY ORLANDO
$375,000
Single Family Home
2482 ROXBURY RD, Winter Park, FL 32789
Winter Park Charm Today — Endless Possibilities Tomorrow. <br>Welcome to a rare find in one of Winter Park's most sough...
Listed by Gary Cohl COLDWELL BANKER REALTY
$110,000
Condo
1695 LEE RD #E116, Winter Park, FL 32789
Under contract-accepting backup offers. Located in the heart of Winter Park, this 3-bedroom, 2-bathroom condo offers an ...
Listed by Cara Edwards ALL REAL ESTATE & INVESTMENTS
$99,000
Condo
1695 LEE RD #B210, Winter Park, FL 32789
This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 ...
Listed by Giuseppina Moriconi GM SUNSHINE REALTY LLC
$709,000
Single Family Home
1701 GOODRICH AVE, Winter Park, FL 32789
Welcome to this thoughtfully updated Winter Park home ideally on a spacious corner lot with a two-car garage offering ex...
Listed by Audra Wilks PREMIER SOTHEBY'S INTL. REALTY
$849,900
Single Family Home
1900 WINTER PARK RD, Winter Park, FL 32789
Positioned in one of Central Florida's most iconic and sought-after locations, this rare opportunity at 1900 Winter Park...
Listed by William Grim, III RE/MAX ASSURED
$1,245,000
Single Family Home
2111 MALLARD CIR, Winter Park, FL 32789
Tucked away on a quiet circle in one of Winter Park's most sought-after neighborhoods, this distinctive pool home offers...
Listed by Caroline Borling BREC PROPERTIES INC
$1,899,900
Condo
106 S INTERLACHEN AVE #518, Winter Park, FL 32789
Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to ...
Listed by Mary Colton FANNIE HILLMAN & ASSOCIATES
$589,000
Single Family Home
1319 BESSMOR RD, Winter Park, FL 32789
Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential ...
Listed by Sidney Galloway GALLOWAY REAL ESTATE
$373,800
Single Family Home
1307 FORMOSA AVE, Winter Park, FL 32789
Under contract-accepting backup offers. Charming 2-bed home in Winter Park located in the Golfview subdivision offering ...
Listed by Tyler Gibson LLC LPT REALTY, LLC
$1,324,000
Single Family Home
802 HAMILTON PLACE CT, Winter Park, FL 32789
Built in 2018, this beautifully designed 4-bedroom, 3.5-bath home offers 2,843 square feet of refined living in a prime ...
Listed by Jacob Theisen FLORIDA CAPITAL REALTY
$460,000
Single Family Home
950 HANOVER AVE, Winter Park, FL 32789
Preferred lender credit available. Welcome home to your peaceful retreat tucked away near the end of a quiet street with...
Listed by Michael Domi COMPASS FLORIDA LLC
$114,000
Condo
1695 LEE RD #D211, Winter Park, FL 32789
Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty ...
Listed by Brandy Ray LOKATION
$1,175,000
Single Family Home
1651 WESTCHESTER AVE, Winter Park, FL 32789
One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neig...
Listed by Shawn Layton SERHANT
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