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Winter Park FL Condos for Rent under $2,000

57 Rentals Available

2500 Lee Rd Unit 244

2500 Lee Rd Unit 244, Winter Park, FL 32789
1 / 5
1 Bed, 1 Bath, 645 sq ft

$1,350

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Pool
1250 S Denning Dr

1250 S Denning Dr, Winter Park, FL 32789
1 / 16
2 Beds

$2,000

Pool

More Units at Mead Garden Condominiums
200 St Andrews Blvd Unit 316

200 St Andrews Blvd, Winter Park, FL 32792
1 / 13
1 Bed

$1,675

Pets Allowed Pool Fitness Center
659 Montego Bay Ct

659 Montego Bay Ct, Winter Park, FL 32792
1 / 20
2 Beds

$1,730

Dogs Allowed
118 Eaton St Unit 4

118 Eaton St Unit 4, Eatonville, FL 32751
1 / 5
1 Bed, 1 Bath, 600 sq ft

$950

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.
551 Flemming Way Unit 201

551 Flemming Way Unit 201, Maitland, FL 32751
1 / 5
1 Bed, 1 Bath, 550 sq ft

$1,150

Total Monthly Price

Total Monthly Price New

Prices include all required monthly fees.

Pool Walk-In Closets Fitness Center
2422 Branch Way Unit 104

2422 Branch Way, Maitland, FL 32751
1 / 5
1 Bed

$1,050

Pool
821 Mulberry St Unit D

821 Mulberry St, Maitland, FL 32751
1 / 12
2 Beds

$2,000
1250 S Denning Dr Unit 127

1250 S Denning Dr Unit 127, Winter Park, FL 32789

For Rent

By Owner
1 / 37
2 Beds, 2 Baths, 911 sq ft

$2,000

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

More Units at Mead Garden Condominiums

2

Available Units

2

Stories

1967

Year Built
2924 Antique Oaks Cir Unit 48

2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792

For Rent

By Owner
1 / 6
2 Beds, 2.5 Baths, 1,100 sq ft

$1,850

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pets Allowed Pool Smoke Free
1920 Woodcrest Dr Unit 13

1920 Woodcrest Dr Unit 13, Winter Park, FL 32792

For Rent

By Owner
1 / 24
2 Beds, 2 Baths, 1,236 sq ft

$1,950

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool
2407 Branch Way Unit 105

2407 Branch Way Unit 105, Maitland, FL 32751

For Rent

By Owner
2 Beds, 1 Bath, 1,150 sq ft

$1,500

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pets Allowed
468 Banyon Tree Cir Unit 202

468 Banyon Tree Cir Unit 202, Maitland, FL 32751

For Rent

By Owner
1 / 11
1 Bed, 1 Bath, 700 sq ft

$1,300

Total Monthly Price
12 Month Lease

Total Monthly Price New

Prices include all required monthly fees.

Pool Smoke Free Fitness Center
1695 Lee Rd Unit A101

1695 Lee Rd Unit A101, Winter Park, FL 32789
1 / 5
3 Beds, 2 Baths, 1,149 sq ft

$1,695

Pets Allowed
1000 S Semoran Blvd Unit 715

1000 S Semoran Blvd Unit 715, Winter Park, FL 32792
1 / 5
1 Bed, 1 Bath, 735 sq ft

$1,200

Pets Allowed
3045 Aaron Burr Ave Unit 12D

3045 Aaron Burr Ave Unit 12D, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 1,062 sq ft

$1,650

Pets Allowed
205 Lewfield Cir Unit 205

205 Lewfield Cir Unit 205, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 927 sq ft

$1,800

Pets Allowed Pool
3651 N Goldenrod Rd Unit 110

3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 840 sq ft

$1,450

Pets Allowed
1695 Lee Rd Unit C110

1695 Lee Rd Unit C110, Winter Park, FL 32789
1 / 5
1 Bed, 1 Bath, 638 sq ft

$1,400

Pets Allowed
7340 Swallow Run Unit 7340

7340 Swallow Run Unit 7340, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 802 sq ft

$1,500

Pets Allowed
7302 Swallow Run Unit 7302

7302 Swallow Run Unit 7302, Winter Park, FL 32792
1 / 5
2 Beds, 2 Baths, 756 sq ft

$1,445

Pets Allowed
1695 Lee Rd Unit B204

1695 Lee Rd Unit B204, Winter Park, FL 32789
1 / 5
2 Beds, 1 Bath, 881 sq ft

$1,500

Pets Allowed
2882 Plaza Terrace Dr Unit 2882

2882 Plaza Terrace Dr Unit 2882, Orlando, FL 32803
1 / 5
2 Beds, 1.5 Baths, 890 sq ft

$1,900

Pets Allowed
524 Georgetown Dr Unit B

524 Georgetown Dr Unit B, Casselberry, FL 32707
1 / 5
1 Bed, 1 Bath, 707 sq ft

$1,299

Pets Allowed
2075 Howell Branch Rd Unit 101

2075 Howell Branch Rd Unit 101, Maitland, FL 32751
1 / 5
2 Beds, 1 Bath, 875 sq ft

$1,325
$1,425

3651 N Goldenrod Rd Unit B203, Winter Park, FL 32792

2 Beds | 2 Baths | 840 sq ft
$1,700

4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

2 Beds | 2 Baths | 1,059 sq ft
$1,450

151 N Orlando Ave, Winter Park, FL 32789

1 Bed | 1 Bath | 600 sq ft

More Units at Lake Killarney Condominiums
$1,375

1000 S Semoran Blvd Unit 806, Winter Park, FL 32792

2 Beds | 2 Baths | 1,045 sq ft
$1,595

1695 Lee Rd, Winter Park, FL 32789

2 Beds | 1 Bath | 881 sq ft
$1,500

1695 Lee Rd Unit Apartment A103, Winter Park, FL 32789

2 Beds | 1 Bath | 881 sq ft
$1,645

7526 University Garden Dr, Winter Park, FL 32792

3 Beds | 2 Baths | 1,300 sq ft
$1,450

2942 Antique Oaks Cir Unit 088, Winter Park, FL 32792

1 Bed | 1 Bath | 749 sq ft
$1,299

200 St Andrews Blvd Unit 206, Winter Park, FL 32792

1 Bed | 1 Bath | 727 sq ft
$1,745

1695 Lee Rd Unit Apartment D215, Winter Park, FL 32789

3 Beds | 2 Baths | 1,149 sq ft
$1,175

3035 George Mason Ave Unit C, Winter Park, FL 32792

1 Bed | 1 Bath | 656 sq ft
$1,500

3651 N Goldenrod Rd Unit E107, Winter Park, FL 32792

2 Beds | 2 Baths | 840 sq ft
$1,595

3004 George Mason Ave Unit K5d, Winter Park, FL 32792

2 Beds | 2.5 Baths | 1,079 sq ft
$1,250

3651 N Goldenrod Rd Unit B202, Winter Park, FL 32792

2 Beds | 2 Baths | 840 sq ft
$2,000

2404 Gallery View Dr, Winter Park, FL 32792

2 Beds | 2 Baths | 902 sq ft
Showing 40 of 57 Results - Page 1 of 2
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Condos Florida Orange County Winter Park

Winter Park, FL Condos for Rent Under $2,000

Search for condos for rent in Winter Park, FL on Apartments.com. With 57 available, you can find the right condo with the floor plan and amenities that fit your needs. When you rent a condo, you’ll likely rent from an individual owner rather than a property management company. This means units in the same building may have different features and layouts. Be sure to check out the photos and take a tour of the unit as you search for your Winter Park home.

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