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238 Properties Available
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$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
$209,999
Condo
851 MILES AVE #13, Winter Park, FL 32789
Under contract-accepting backup offers. Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom seco...
Listed by Eric Campbell LPT REALTY, LLC
$1,399,000
Townhouse
512 W SWOOPE AVE, Winter Park, FL 32789
Vilasa Homes — Winter Park's Expression of Modern Luxury. Perfectly positioned just steps from Park Avenue, this archit...
Listed by Carmen Quintana COLDWELL BANKER REALTY
$1,849,900
Condo
101 S NEW YORK AVE #311, Winter Park, FL 32789
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the h...
Listed by Tiffany Grindstaff KELLY PRICE & COMPANY LLC
$849,000
Single Family Home
437 N CAPEN AVE, Winter Park, FL 32789
Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this except...
Listed by Brandon Geers COMPASS FLORIDA LLC
$2,250,000
Single Family Home
240 N PHELPS AVE, Winter Park, FL 32789
A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designe...
Listed by Nick McKee KELLER WILLIAMS WINTER PARK
$560,000
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 Jeanine Louis, LLC EXP REALTY LLC
$1,095,000
Single Family Home
1741 MIZELL AVE, Winter Park, FL 32789
Culture, Convenience, Community! Discover refined living in the heart of Winter Park, where timeless luxury meets an unm...
Listed by Farah Novin PREMIER SOTHEBY'S INTL. REALTY
$1,599,000
Single Family Home
1864 GRINNELL TER, Winter Park, FL 32789
Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience...
Listed by Robyn Brehne-Glass COLDWELL BANKER REALTY
$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
$1,495,000
Single Family Home
1565 FOREST AVE, Winter Park, FL 32789
Virtually Staged. Set apart from the ordinary, this historic Winter Park residence offers a rare opportunity to own a ho...
Listed by Elizabeth Nordquist NORDQUIST & COMPANY INC
$3,393,000
Single Family Home
1581 FOREST AVE, Winter Park, FL 32789
This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoug...
Listed by Julie Christensen ONE LUXURY INTERNATIONAL LLC
$1,950,000
Single Family Home
2625 PARK PLACE DR, Winter Park, FL 32789
Nestled on one of Winter Park's most exclusive streets, this exceptional residence is located within Park Place—the only...
Listed by John McDade FANNIE HILLMAN & ASSOCIATES
$6,500
Townhouse
501 W CANTON AVE, Winter Park, FL 32789
Look no further, this luxury Modern Townhome offers premium location just minutes from Park Avenue, restaurants, shoppin...
Listed by Nicole Howell FANNIE HILLMAN & ASSOCIATES
$2,500
Single Family Home
1540 ONECO AVE, Winter Park, FL 32789
Nestled on a picturesque, tree-lined brick street, this charming 3-bedroom, 2-bath home offers an unbeatable location ju...
Listed by Tara Mason WATSON REALTY CORP
$250,000
Condo
1500 GAY RD #3C, Winter Park, FL 32789
WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renova...
Listed by Heather Frazee FANNIE HILLMAN & ASSOCIATES
$199,900
Condo
151 NORTH ORLANDO AVENUE #142, Winter Park, FL 32789
**Lakeside Living Meets Urban Convenience in the Heart of Winter Park!** <br> <br>Welcome home to this beautifully updat...
Listed by Chris Creegan CREEGAN GROUP
$2,450
Single Family Home
1440 MICHIGAN AVE, Winter Park, FL 32789
Live in the heart of Winter Park, just steps from the city's most loved restaurants, cafés, yoga studios, and boutique s...
Listed by Farzana Zalil CHARLES RUTENBERG REALTY ORLANDO
$1,600
Condo
1695 LEE RD #B204, Winter Park, FL 32789
2 bedroom, 2 bathroom condo located in the desirable and well maintained Waterfall Cove community in Winter Park. New ti...
Listed by Mauricio Toro MTRE GROUPE LLC
$1,795,000
Single Family Home
2501 LAFAYETTE AVE, Winter Park, FL 32789
Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft arc...
Listed by Michael Elias CHARLES RUTENBERG REALTY ORLANDO
$5,500,000
Single Family Home
313 SYLVAN DR, Winter Park, FL 32789
Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan presents a rare opportuni...
Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY
$3,995,000
Single Family Home
1600 LEGION DR, Winter Park, FL 32789
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Kei...
Listed by Brian Teach COLDWELL BANKER REALTY
$3,500,000
Single Family Home
1836 WHITEHALL DR, Winter Park, FL 32789
Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil i...
Listed by Bianca Khoury PREMIER SOTHEBY'S INTL. REALTY
$3,490,000
Single Family Home
121 E FAWSETT RD, Winter Park, FL 32789
Under Construction. New construction by LUIH Homes, ideally on a charming brick street in one of Winter Park's desirable...
Listed by Mick Night PREMIER SOTHEBY'S INTL. REALTY
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