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540 Properties

540 Properties Available In Winter Park

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1500 GAY RD #10C, Winter Park, FL 32789
1/20 20

$236,000

Pending

Condo

2 Beds 2 Baths 1,026 SqFt

1500 GAY RD #10C, Winter Park, FL 32789

Under contract-accepting backup offers. Waterfront Community on beautiful Lake Killarney. Enjoy breathtaking sunsets on ...

Listed by REALCOM REAL ESTATE SERVICES INC

1850 WHITEHALL DR, Winter Park, FL 32789
1/34 34

$3,400

Pending

Single Family Home

3 Beds 2 Baths 1,670 SqFt

1850 WHITEHALL DR, Winter Park, FL 32789

This is a wonderful, furnished, pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. ...

Listed by FANNIE HILLMAN & ASSOCIATES

622 PENN PL, Winter Park, FL 32789
1/26 26

$1,950,000

Active

Single Family Home

3 Beds 4 Baths 2,767 SqFt

622 PENN PL, Winter Park, FL 32789

Located just steps to the Golf Course and Park Avenue, in downtown Winter Park, 622 Penn Place is in the highly sought a...

Listed by COMMUNITY REALTY ASSOCIATES

1762 MONDRIAN CIR, Winter Park, FL 32789
1/42 42

$895,000

Active

Townhouse

3 Beds 4 Baths 2,265 SqFt

1762 MONDRIAN CIR, Winter Park, FL 32789

Introducing a stunning brand-new modern brownstone in the heart of Winter Park, offering access to Lake Killarney. Locat...

Listed by COLDWELL BANKER RESIDENTIAL RE

3458 BALSAM DR, Winter Park, FL 32792
1/12 12

$475,000

Price Dropped by $14K

Single Family Home

3 Beds 2 Baths 1,910 SqFt

3458 BALSAM DR, Winter Park, FL 32792

Seller motivated! Seller to offer, $2500 towards buyers closing cost, and prepaid items at closing. Come see this charm...

Listed by CENTURY 21 BE3

2033 CANNY CV, Winter Park, FL 32792
1/34 34

$457,000

Active

Townhouse

3 Beds 3 Baths 1,907 SqFt

2033 CANNY CV, Winter Park, FL 32792

Step into this stunning townhome and be greeted by an open-concept kitchen, dining, and living area—perfect for entertai...

Listed by LPT REALTY, LLC

817 ANTONETTE AVE, Winter Park, FL 32789
1/60 60

$1,825,000

Price Dropped by $70K

Single Family Home

4 Beds 3 Baths 3,971 SqFt

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

141 OAKWOOD WAY, Winter Park, FL 32789
1/58 58

$2,254,000

Price Dropped by $25K

Single Family Home

5 Beds 4 Baths 3,909 SqFt

141 OAKWOOD WAY, Winter Park, FL 32789

Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area....

Listed by MAINFRAME REAL ESTATE

785 N PHELPS AVE, Winter Park, FL 32789
1/10 10

$2,119,000

Active

Single Family Home

5 Beds 5 Baths 2,964 SqFt

785 N PHELPS AVE, Winter Park, FL 32789

Under Construction. Completion September 2025, Nestled in the heart of Winter Park, this luxurious custom-built home sea...

Listed by COMPASS FLORIDA LLC

1470 PLACE PICARDY, Winter Park, FL 32789
1/27 27

$1,770,000

Price Dropped by $25K

Single Family Home

5 Beds 6 Baths 4,227 SqFt

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

1400 S PENNSYLVANIA AVE, Winter Park, FL 32789
1/50 50

$1,300,000

Price Dropped by $50K

Single Family Home

4 Beds 3 Baths 2,060 SqFt

1400 S PENNSYLVANIA AVE, Winter Park, FL 32789

Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. <br>You will...

Listed by JACK KELLER INC

3131 ASH PARK LOOP, Winter Park, FL 32792
1/72 72

$374,900

Price Dropped by $25K

Single Family Home

2 Beds 2 Baths 1,408 SqFt

3131 ASH PARK LOOP, Winter Park, FL 32792

Welcome to your next home located at 3131 Ash Park Loop in the serene Hyde Park community. This inviting 2-bedroom, 2-ba...

Listed by STRICKLAND REALTY GROUP INC

2207 WINTER WOODS BLVD, Winter Park, FL 32792
1/40 40

$455,000

Pending

Single Family Home

4 Beds 2 Baths 1,710 SqFt

2207 WINTER WOODS BLVD, Winter Park, FL 32792

Under contract-accepting backup offers. Welcome to this inviting 4-bedroom, 2-bathroom home on an oversized corner lot i...

Listed by COLDWELL BANKER REALTY

700 MELROSE AVE #A 22, Winter Park, FL 32789
1/25 25

$285,000

Price Dropped by $14K

Condo

2 Beds 2 Baths 1,074 SqFt

700 MELROSE AVE #A 22, Winter Park, FL 32789

HUGE PRICE CHANGE! <br>Welcome to this beautifully updated second-floor unit, offering a fresh and modern living exper...

Listed by FANNIE HILLMAN & ASSOCIATES

2100 SUFFIELD DR, Winter Park, FL 32792
1/46 46

$599,900

Pending

Single Family Home

3 Beds 3 Baths 1,807 SqFt

2100 SUFFIELD DR, Winter Park, FL 32792

Under contract-accepting backup offers. GREAT BONES! A fantastic opportunity for you to own your slice on Winter Park. T...

Listed by RE/MAX 200 REALTY

702 VIA BELLA, Winter Park, FL 32789
1/8 8

$4,500,000

Active

Single Family Home

5 Beds 6 Baths 3,720 SqFt

702 VIA BELLA, Winter Park, FL 32789

Under Construction. New Custom Home in the Desirable Winter Park Via's – Completion Expected June 2025 <br>This exceptio...

Listed by FLORIDIAN REALTY GROUP LLC

2855 CADY WAY, Winter Park, FL 32792
1/35 35

$549,900

Pending

Single Family Home

3 Beds 2 Baths 1,736 SqFt

2855 CADY WAY, Winter Park, FL 32792

Under contract-accepting backup offers. Recently renovated 1964 3/2/2 Winter Park stunner. This 3 bedroom, 2 bathroom, 2...

Listed by GLOBAL PROPERTIES SALES & MGMT

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