32789, FL rental listings

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ABOUT THIS HOME
32789, FL Rental Listings
Welcome to this beautifully updated Mediterranean-style home in the desirable Orwin Manor neighborhood of Winter Park. This charming 3-bedroom, 2-bath residence offers 1,819 sq ft of thoughtfully desi

$4,200/mo

3 beds2 baths1,819 sq ft

1381 Canterbury Rd, Winter Park, FL 32789

Pets welcome • Parking • A/C

ABOUT THIS HOME
32789, FL Rental Listings
5 bedrooms, 3 bathrooms super close to Winter Park Village and conveniently located close to all Winter Park activities. Lots of remodeling!! No garage, large treed backyard!

$3,500/mo

6 beds3 baths2,722 sq ft

1288 Michigan Ave, Winter Park, FL 32789

Dogs welcome • Parking • A/C

ABOUT THIS HOME
32789, FL Rental Listings
Luxury Living in Historic Winter ParkAmazing location in the heart of Winter Park and nestled within the historic Barbour House--a symbol of timeless elegance. This chic apartment offers a luxurious r

$2,400/mo

1 bed1 bath525 sq ft

544 N Knowles Ave Unit 302, Winter Park, FL 32789

Available 11/01 • Pets welcome • Parking

ABOUT THIS HOME
32789, FL Rental Listings
Come see this 3 bedroom/2 bathroom bungalow in the heart of downtown Orlando. Equipped with brand new roof, new windows, screened porch, nice big lot and a fenced yard this home is ready for a long te

$2,100/mo

3 beds2 baths1,340 sq ft

2004 Indiana Ave, Winter Park, FL 32789

Available 11/01 • Dogs welcome • Parking

ABOUT THIS HOME
32789, FL Rental Listings
This fantastic 2/2 plus office Orwin Manor home just completed new kitchen updates and features hardwood flooring throughout with tile in kitchen and Florida Room/Sunroom areas. Florida Room/sunroom i

$2,500/mo

2 beds2 baths1,375 sq ft

1513 Harmon Ave, Winter Park, FL 32789

Pets welcome • Laundry in unit • Parking

ABOUT THIS HOME
32789, FL Rental Listings
Charming 3-Bedroom Home for Rent in Winter ParkThis beautiful 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. Featuring spacious living

$2,300/mo

2 beds1.5 baths1,091 sq ft

2011 Cornell Ave, Winter Park, FL 32789

Dogs welcome • Parking • A/C

Property at 263 Blossom Ln, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$2,300/mo

2 beds1 bath1,076 sq ft

263 Blossom Ln, Winter Park, FL 32789

Property at 939 Aragon Ave, Winter Park, FL, 32789, 2 beds, 2 baths, [object Object]

$2,725/mo

2 beds2 baths1,127 sq ft

939 Aragon Ave, Winter Park, FL 32789

Property at 2227 Howard Dr, Winter Park, FL, 32789, 3 beds, 2.5 baths, [object Object]

$4,700/mo

3 beds2.5 baths2,196 sq ft

2227 Howard Dr, Winter Park, FL 32789

Property at 2817 Eastern Pkwy, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$2,995/mo

3 beds2 baths1,376 sq ft

2817 Eastern Pkwy, Winter Park, FL 32789

Property at 1530 Via Tuscany, Winter Park, FL, 32789, 4 beds, 3.5 baths, [object Object]

$10,500/mo

4 beds3.5 baths3,341 sq ft

1530 Via Tuscany, Winter Park, FL 32789

Property at 200 Sandlewood Trl #4, Winter Park, FL, 32789, 2 beds, 2.5 baths, [object Object]

$1,895/mo

2 beds2.5 baths1,133 sq ft

200 Sandlewood Trl #4, Winter Park, FL 32789

Property at 632 Gaines Way, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$2,100/mo

1 bed1 bath550 sq ft

632 Gaines Way, Winter Park, FL 32789

Property at 2020 Venetian Way, Winter Park, FL, 32789, 4 beds, 3.5 baths, [object Object]

$8,990/mo

4 beds3.5 baths4,188 sq ft

2020 Venetian Way, Winter Park, FL 32789

Property at 460 Cambridge Blvd Unit B, Winter Park, FL, 32789, 2 beds, 2 baths, [object Object]

$1,850/mo

2 beds2 baths945 sq ft

460 Cambridge Blvd Unit B, Winter Park, FL 32789

Property at 1641 Chestnut Ave, Winter Park, FL, 32789, 3 beds, 3 baths, [object Object]

$3,595/mo

3 beds3 baths1,750 sq ft

1641 Chestnut Ave, Winter Park, FL 32789

Property at 1681 Walnut Ave, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$3,799/mo

3 beds2 baths1,499 sq ft

1681 Walnut Ave, Winter Park, FL 32789

Property at 1860 Via Contessa, Winter Park, FL, 32789, 8 beds, 6 baths, [object Object]

$17,550/mo

8 beds6 baths7,000 sq ft

1860 Via Contessa, Winter Park, FL 32789

Property at 1500 Gay Rd Unit 9B, Winter Park, FL, 32789, 2 beds, 2 baths, [object Object]

$2,000/mo

2 beds2 baths1,026 sq ft

1500 Gay Rd Unit 9B, Winter Park, FL 32789

Property at 2031 Temple Dr, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$5,150/mo

3 beds2 baths1,636 sq ft

2031 Temple Dr, Winter Park, FL 32789

Property at 1181 Woodmere Dr, Winter Park, FL, 32789, 5 beds, 4 baths, [object Object]

$6,995/mo

5 beds4 baths4,254 sq ft

1181 Woodmere Dr, Winter Park, FL 32789

Property at 1500 Gay Rd Unit 18-C, Winter Park, FL, 32789, 2 beds, 2 baths, [object Object]

$1,795/mo

2 beds2 baths1,026 sq ft

1500 Gay Rd Unit 18-C, Winter Park, FL 32789

Property at 1148 Park Green Pl, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$2,395/mo

3 beds2 baths1,282 sq ft

1148 Park Green Pl, Winter Park, FL 32789

Property at 1500 Gay Rd Unit 3B, Winter Park, FL, 32789, 2 beds, 2 baths, [object Object]

$1,975/mo

2 beds2 baths1,100 sq ft

1500 Gay Rd Unit 3B, Winter Park, FL 32789

Property at 2500 Lee Rd #244, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath645 sq ft

2500 Lee Rd #244, Winter Park, FL 32789

Property at 700 Melrose Ave Unit K32, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,300/mo

1 bed1 bath772 sq ft

700 Melrose Ave Unit K32, Winter Park, FL 32789

Property at 1107 S Pennsylvania Ave, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$1,900/mo

2 beds1 bath737 sq ft

1107 S Pennsylvania Ave, Winter Park, FL 32789

Property at 235 Sandlewood Trl, Winter Park, FL, 32789, 3 beds, 3.5 baths, [object Object]

$1,800/mo

3 beds3.5 baths1,413 sq ft

235 Sandlewood Trl, Winter Park, FL 32789

Property at 232 Sandlewood Trl Unit 1, Winter Park, FL, 32789, 2 beds, 2.5 baths, [object Object]

$1,950/mo

2 beds2.5 baths1,098 sq ft

232 Sandlewood Trl Unit 1, Winter Park, FL 32789

Property at 1500 Michigan Ave Unit B, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$1,449/mo

2 beds1 bath650 sq ft

1500 Michigan Ave Unit B, Winter Park, FL 32789

Property at 2828 Salisbury Blvd, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$2,195/mo

3 beds2 baths1,408 sq ft

2828 Salisbury Blvd, Winter Park, FL 32789

Property at 775 Maryland Ave, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$3,200/mo

2 beds1 bath900 sq ft

775 Maryland Ave, Winter Park, FL 32789

Property at 130 N Center St Unit 2, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,665/mo

1 bed1 bath1,000 sq ft

130 N Center St Unit 2, Winter Park, FL 32789

Property at 1127 Minnesota Ave #3, Winter Park, FL, 32789, 3 beds, 2.5 baths, [object Object]

$2,998/mo

3 beds2.5 baths1,852 sq ft

1127 Minnesota Ave #3, Winter Park, FL 32789

Property at 1695 Lee Rd Unit D212, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$1,475/mo

2 beds1 bath881 sq ft

1695 Lee Rd Unit D212, Winter Park, FL 32789

Property at 1695 Lee Rd Unit B114, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$1,650/mo

2 beds1 bath881 sq ft

1695 Lee Rd Unit B114, Winter Park, FL 32789

Property at 1695 Lee Rd, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$1,500/mo

2 beds1 bath881 sq ft

1695 Lee Rd, Winter Park, FL 32789

Property at 957 DuPont Ave, Winter Park, FL, 32789, 3 beds, 2.5 baths, [object Object]

$2,750/mo

3 beds2.5 baths1,152 sq ft

957 DuPont Ave, Winter Park, FL 32789

Property at 2326 Wellington Blvd, Winter Park, FL, 32789, 1 bed, 1 bath, [object Object]

$1,050/mo

1 bed1 bath755 sq ft

2326 Wellington Blvd, Winter Park, FL 32789

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Based on information submitted to the MLS GRID as of Mon Oct 13 2025. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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