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258 Properties

258 Properties Available In 32789

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2430 CHANTILLY AVE, Winter Park, FL 32789
1/64 64

$1,598,000

Open Sun 2PM-4PM

Single Family Home

4 Beds 4 Baths 2,916 SqFt

2430 CHANTILLY AVE, Winter Park, FL 32789

Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed...

Listed by Kelly Price KELLY PRICE & COMPANY LLC

1761 LEGION DR, Winter Park, FL 32789
1/66 66

$3,265,000

Open Sun 1PM-4PM

Single Family Home

5 Beds 6 Baths 4,924 SqFt

1761 LEGION DR, Winter Park, FL 32789

One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combi...

Listed by Harry Pool, III COLDWELL BANKER REALTY

1661 LAUREL RD, Winter Park, FL 32789
1/81 81

$1,875,000

Open Sun 1PM-3PM

Single Family Home

3 Beds 3 Baths 3,127 SqFt

1661 LAUREL RD, Winter Park, FL 32789

Set along the brick-lined streets of Charmont, one of Winter Park's most coveted and established neighborhoods, 1661 Lau...

Listed by Caroline Van Den Berg VAN DEN BERG REAL ESTATE GROUP

900 CARVER ST, Winter Park, FL 32789
3D

$689,000

Open Sun 12PM-4PM

Single Family Home

3 Beds 3 Baths 1,794 SqFt

900 CARVER ST, Winter Park, FL 32789

Completely Remodeled 2026 | Single-Story | Prime Location | Dual Suites | The redesigned kitchen features 42" shaker cab...

Listed by Farhad Haniff EXP REALTY LLC

151 N ORLANDO AVE #261, Winter Park, FL 32789
1/26 26

$239,999

Open Sun 1:30PM-3PM

Condo

1 Bed 1 Bath 582 SqFt

151 N ORLANDO AVE #261, Winter Park, FL 32789

Location, location, location! Bring your boat, enjoy lake views and the best of Winter Park from this beautifully update...

Listed by Nikita Ager, LLC FLORIDA REALTY INVESTMENTS

720 PANSY AVE, Winter Park, FL 32789
1/58 58

$1,350,000

Coming Soon

Single Family Home

3 Beds 4 Baths 2,191 SqFt

720 PANSY AVE, Winter Park, FL 32789

Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and ...

Listed by Nick McKee KELLER WILLIAMS WINTER PARK

565 HUNTINGTON AVE #565, Winter Park, FL 32789
1/27 27

$635,000

Open Sun 2PM-4PM

Condo

3 Beds 3 Baths 2,015 SqFt

565 HUNTINGTON AVE #565, Winter Park, FL 32789

Private, no-through-traffic street in one of Winter Park's most desirable locations. Just a short walk from downtown Win...

Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

1431 PALM AVE, Winter Park, FL 32789
1/38 38

$850,000

Open 8/30 10:30AM-1:30PM

Single Family Home

2 Beds 2 Baths 1,540 SqFt

1431 PALM AVE, Winter Park, FL 32789

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park's desirable neighborhoods, where classic...

Listed by Kelsey Payton ALL REAL ESTATE & INVESTMENTS

1525 GRANVILLE DR, Winter Park, FL 32789
1/56 56

$4,595,000

Open 8/30 12PM-2PM

Single Family Home

5 Beds 6 Baths 5,211 SqFt

1525 GRANVILLE DR, Winter Park, FL 32789

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vim...

Listed by Julie Christensen ONE LUXURY INTERNATIONAL LLC

1836 WHITEHALL DR, Winter Park, FL 32789
1/70 70

$3,245,000

Open 8/30 12PM-2PM

Single Family Home

5 Beds 7 Baths 4,168 SqFt

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

1421 CHAPMAN CIR, Winter Park, FL 32789
1/49 49

$1,450,000

Open Sun 2PM-4PM

Single Family Home

4 Beds 4 Baths 3,578 SqFt

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

1265 ARLINGTON PL, Winter Park, FL 32789
1/38 38

$810,000

Open Sun 1PM-4PM

Townhouse

3 Beds 4 Baths 2,030 SqFt

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

1473 BERKSHIRE AVE, Winter Park, FL 32789
1/38 38

$1,399,000

Open Sun 11AM-4PM

Single Family Home

5 Beds 4 Baths 2,351 SqFt

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

641 NORTHWOOD CIRCLE, Winter Park, FL 32789
1/37 37

$1,599,000

Open Sun 1PM-3PM

Single Family Home

3 Beds 5 Baths 2,756 SqFt

641 NORTHWOOD CIRCLE, Winter Park, FL 32789

Virtually Staged. 641 Northwood Circle is a rare opportunity to own newer construction in the heart of Winter Park at a ...

Listed by Sandra Cuba PREMIER SOTHEBY'S INTL. REALTY

1120 WISCONSIN AVE, Winter Park, FL 32789
1/37 37

$1,079,000

Open Sun 1PM-3PM

Single Family Home

3 Beds 4 Baths 2,213 SqFt

1120 WISCONSIN AVE, Winter Park, FL 32789

Curated with intention and finished without compromise, 1120 Wisconsin Avenue is a rare opportunity to own a bespoke Win...

Listed by Kelly Price KELLY PRICE & COMPANY LLC

1611 CHESTNUT AVE, Winter Park, FL 32789
1/51 51

$995,000

Open Sun 2PM-4PM

Single Family Home

4 Beds 4 Baths 2,916 SqFt

1611 CHESTNUT AVE, Winter Park, FL 32789

HUGE PRICE IMPROVEMENT!! BRING ALL OFFERS!! Situated on arguably the finest brick street in Winter Park, beneath a canop...

Listed by Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

106 S INTERLACHEN AVE #518, Winter Park, FL 32789
1/58 58

$1,795,000

Open 8/30 12PM-2PM

Condo

3 Beds 2 Baths 1,807 SqFt

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

1261 INDIANA AVE, Winter Park, FL 32789
1/31 31

$540,000

Open Sun 1PM-3PM

Townhouse

3 Beds 3 Baths 1,660 SqFt

1261 INDIANA AVE, Winter Park, FL 32789

Welcome to easy living in the heart of Winter Park. This beautifully bright end unit townhome offers 1,660 square feet o...

Listed by Megan Cross FANNIE HILLMAN & ASSOCIATES

1441 CARDINAL CT, Winter Park, FL 32789
3D

$3,995,000

Open 8/30 12PM-2PM

Single Family Home

4 Beds 6 Baths 4,066 SqFt

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

541 W CANTON AVE, Winter Park, FL 32789
1/51 51

$2,650,000

Open 8/30 12PM-2PM

Single Family Home

4 Beds 4 Baths 3,553 SqFt

541 W CANTON AVE, Winter Park, FL 32789

Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch...

Listed by Bianca Khoury PREMIER SOTHEBY'S INTL. REALTY

2501 WINTER PARK RD, Winter Park, FL 32789
1/50 50

$1,649,000

Open Sun 3PM-5PM

Single Family Home

5 Beds 4 Baths 3,304 SqFt

2501 WINTER PARK RD, Winter Park, FL 32789

PRICED BELOW APPRAISAL, CUSTOM BAREFOOT BROTHERS HOME IN WINTER PARK. Finding a truly CUSTOM-BUILT home in Winter Park i...

Listed by Jill Healey KELLER WILLIAMS WINTER PARK

151 N ORLANDO AVE ##115, Winter Park, FL 32789
1/22 22

$285,000

Open Sun 1:30PM-3PM

Condo

2 Beds 1 Bath 710 SqFt

151 N ORLANDO AVE ##115, Winter Park, FL 32789

Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering ...

Listed by Chris Creegan CREEGAN GROUP

1150 VIA SALERNO, Winter Park, FL 32789
1/64 64

$3,750,000

Open Sun 2PM-4PM

Single Family Home

4 Beds 6 Baths 3,826 SqFt

1150 VIA SALERNO, Winter Park, FL 32789

In the heart of Winter Park, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends archit...

Listed by Padgett McCormick KELLY PRICE & COMPANY LLC

1220 HOWELL BRANCH RD, Winter Park, FL 32789
1/49 49

$1,200,000

New

Single Family Home

3 Beds 2 Baths 1,487 SqFt

1220 HOWELL BRANCH RD, Winter Park, FL 32789

A RARE WINTER PARK RENOVATION OPPORTUNITY DIRECTLY ACROSS FROM HOWELL BRANCH PRESERVE! Situated on an approximately 0.23...

Listed by Fook Snipper PARK PLACE REAL ESTATE

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