32 Properties Available
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$1,550,000
Single Family Home
1421 CHAPMAN CIR, Winter Park, FL 32789
Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong communi...
Listed by Kelly Price KELLY PRICE & COMPANY 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
$879,000
Townhouse
1265 ARLINGTON PL, Winter Park, FL 32789
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park'...
Listed by Erika Beerbower FANNIE HILLMAN & ASSOCIATES
$1,429,000
Single Family Home
1473 BERKSHIRE AVE, Winter Park, FL 32789
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this s...
Listed by Gilson Rodrigues KARDOSH REALTY
$509,000
Single Family Home
641 W LYMAN AVE, Winter Park, FL 32789
LOCATION. LOCATION. LOCATION. Heres the thing; in Winter Park, that's not a cliché. It's everything. <br> <br>There are ...
Listed by Ted Moseley REAL BROKER, LLC
$245,000
Condo
700 MELROSE AVE #K25, Winter Park, FL 32789
Bright, beautifully updated 1-bed/1-bath condo with floor-to-ceiling views and a prime walkable location in the heart of...
Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
$1,795,000
Single Family Home
641 NORTHWOOD CIRCLE, Winter Park, FL 32789
Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of ...
Listed by Sandra Cuba PREMIER SOTHEBY'S INTL. REALTY
$550,000
Single Family Home
2974 CHANTILLY AVE, Winter Park, FL 32789
Virtually Staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park Hi...
Listed by Catherine D'Amico FANNIE HILLMAN & ASSOCIATES
$235,900
Condo
700 MELROSE AVE #F 21, Winter Park, FL 32789
Floor-to-ceiling dazzling views, of sparkling pond, sweepiing oaks, towering cypress trees, and lush gardens — in the ce...
Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
$3,500,000
Townhouse
649 N PARK AVE, Winter Park, FL 32789
Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at t...
Listed by Drew Henner PREMIER SOTHEBY'S INTL. REALTY
$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
$989,500
Condo
269 E CANTON AVE #269, Winter Park, FL 32789
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy ...
Listed by Cathy Sawruk Williams COLDWELL BANKER REALTY
$395,000
Condo
340 KILLARNEY BAY CT #4-4, Winter Park, FL 32789
Welcome to 340 Killarney Bay, a beautifully maintained residence located within one of Winter Park's most charming and s...
Listed by Blaike Gill KELLER WILLIAMS WINTER PARK
$1,665,000
Single Family Home
2430 CHANTILLY AVE, Winter Park, FL 32789
Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned...
Listed by Julie Christensen ONE LUXURY INTERNATIONAL LLC
$1,925,000
Condo
311 E MORSE BLVD #1-3, Winter Park, FL 32789
Enjoy the Winter Park lifestyle in this beautifully renovated 2-bedroom, 2-bath lakefront condo offering 2,304 square fe...
Listed by Megan Cross FANNIE HILLMAN & ASSOCIATES
$1,875,000
Single Family Home
1813 HARLAND PARK DR, Winter Park, FL 32789
Nestled within the highly sought-after Windsong community in Winter Park, this thoughtfully designed residence presents ...
Listed by MaryStuart Day FANNIE HILLMAN & ASSOCIATES
$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
$639,900
Single Family Home
1830 EDWIN BLVD, Winter Park, FL 32789
Beautifully RENOVATED and MOVE-IN READY/TURN-KEY home in the heart of Winter Park. From the moment you enter, you're wel...
Listed by Nydia Marrero ZEN LIVING HOMES LLC
$4,285,000
Single Family Home
1441 CARDINAL CT, Winter Park, FL 32789
Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Wi...
Listed by Damian Bergler CHARLES RUTENBERG REALTY ORLANDO
$1,900,000
Single Family Home
785 N PHELPS AVE, Winter Park, FL 32789
Exquisite new construction in the heart of Winter Park, this LUIH Luxury Homes residence distinguishes itself through re...
Listed by Christopher Christensen ONE LUXURY INTERNATIONAL LLC
$525,000
Condo
1807 HAMMERLIN AVE #G, Winter Park, FL 32789
**Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Miche...
Listed by Courtney Dietch ALL REAL ESTATE & INVESTMENTS
$995,000
Single Family Home
1800 MAGNOLIA AVE, Winter Park, FL 32789
Virtually Staged. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a corne...
Listed by Kathy Summers FLORIDA REALTY INVESTMENTS
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