Winter Park, FL rental listings

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ABOUT THIS HOME
Winter Park, FL Rental Listings
COMING SOON! Newly remodeled 3/ 1 with carport, Bonus room/den/office and storage room. New kitchen cabinets and countertops with All new stainless steel appliances and remodeled bath. Located in the

$1,995/mo

3 beds1 bath977 sq ft

931 Cypress Ave, Winter Park, FL 32789

Pets welcome • Very walkable • Some transit

ABOUT THIS HOME
Winter Park, FL Rental Listings
We make Pre-Leasing easy! Apply now and, once you're approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made r

$2,835/mo

4 beds2 baths1,534 sq ft

2045 Houndslake Dr, Winter Park, FL 32792

Available 01/14 • Pets welcome • A/C

ABOUT THIS HOME
Winter Park, 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
Winter Park, FL Rental Listings
Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location

$8,500/mo

4 beds3 baths2,476 sq ft

300 Killarney Dr, Winter Park, FL 32789

Available 01/01 • Pets welcome • Parking

ABOUT THIS HOME
Winter Park, 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

$2,100/mo

2 beds1.5 baths1,091 sq ft

2011 Cornell Ave, Winter Park, FL 32789

Dogs welcome • Parking • A/C

ABOUT THIS HOME
Winter Park, FL Rental Listings
Available: January 1st, 2026 Rent: $1,200/month ! Security Deposit: $1,200 Looking for the perfect spot in a vibrant, food-filled neighborhood? This 1-bedroom room in Maitland borders Winter Park, the

$1,200/mo

1 bed1 bath1,289 sq ft

981 Hamlet Ct, Maitland, FL 32751

Laundry in unit • Parking • A/C

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 1112 Chichester St, Orlando, FL, 32803, 4 beds, 3 baths, [object Object]

$4,499/mo

4 beds3 baths2,252 sq ft

1112 Chichester St, Orlando, FL 32803

Property at 3260 Lake Shore Dr, Orlando, FL, 32803, 5 beds, 7.5 baths, [object Object]

$22,500/mo

5 beds7.5 baths6,709 sq ft

3260 Lake Shore Dr, Orlando, FL 32803

Property at 1931 Carrigan Ave, Winter Park, FL, 32792, 3 beds, 2 baths, [object Object]

$2,200/mo

3 beds2 baths1,113 sq ft

1931 Carrigan Ave, Winter Park, FL 32792

Property at 2128 Sycamore Dr, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$3,300/mo

3 beds2 baths1,760 sq ft

2128 Sycamore Dr, 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 1530 Via Tuscany, Winter Park, FL, 32789, 4 beds, 3.5 baths, [object Object]

$9,000/mo

4 beds3.5 baths3,341 sq ft

1530 Via Tuscany, Winter Park, FL 32789

Property at 5169 Lazy Oaks Dr, Winter Park, FL, 32792, 2 beds, 2.5 baths, [object Object]

$1,975/mo

2 beds2.5 baths1,236 sq ft

5169 Lazy Oaks Dr, Winter Park, FL 32792

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 1622 Arbor Park Dr, Winter Park, FL, 32789, 3 beds, 1.5 baths, [object Object]

$2,500/mo

3 beds1.5 baths1,351 sq ft

1622 Arbor Park Dr, Winter Park, FL 32789

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

$3,295/mo

3 beds3 baths1,750 sq ft

1641 Chestnut Ave, Winter Park, FL 32789

Property at 151 N Orlando Ave Unit 151-203, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$2,400/mo

2 beds1 bath800 sq ft

151 N Orlando Ave Unit 151-203, Winter Park, FL 32789

Property at 1442 Palm Ave, Winter Park, FL, 32789, 4 beds, 5 baths, [object Object]

$8,900/mo

4 beds5 baths3,611 sq ft

1442 Palm Ave, Winter Park, FL 32789

Property at 1730 Oneco Ave, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$3,150/mo

3 beds2 baths1,408 sq ft

1730 Oneco Ave, Winter Park, FL 32789

Property at 1350 Lyndale Blvd, Winter Park, FL, 32789, 4 beds, 3.5 baths, [object Object]

$9,000/mo

4 beds3.5 baths3,478 sq ft

1350 Lyndale Blvd, Winter Park, FL 32789

Property at 2717 Scarlet Rd Unit 2717, Winter Park, FL, 32792, 3 beds, 2 baths, [object Object]

$2,795/mo

3 beds2 baths1,240 sq ft

2717 Scarlet Rd Unit 2717, Winter Park, FL 32792

Property at 7973 Pleasant Pine Cir, Winter Park, FL, 32792, 4 beds, 3 baths, [object Object]

$3,150/mo

4 beds3 baths2,479 sq ft

7973 Pleasant Pine Cir, Winter Park, FL 32792

Property at Lancelot of Winter Park - 3651 N Goldenrod Rd, Winter Park, FL, 32792, 2 beds, 2 baths, [object Object]

$1,350+/mo

2 beds2 baths840 sq ft

Lancelot of Winter Park

| 3651 N Goldenrod Rd, Winter Park, FL 32792

Property at 7429 Daniel Webster Dr Unit C, Winter Park, FL, 32792, 2 beds, 2 baths, [object Object]

$1,740/mo

2 beds2 baths1,036 sq ft

7429 Daniel Webster Dr Unit C, Winter Park, FL 32792

Property at 332 Harris Ave Unit 332, Winter Park, FL, 32789, 3 beds, 2 baths, [object Object]

$3,000/mo

3 beds2 baths1,392 sq ft

332 Harris Ave Unit 332, Winter Park, FL 32789

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

$1,475/mo

1 bed1 bath645 sq ft

2500 Lee Rd #244, Winter Park, FL 32789

Property at 1492 Broad Wing Ln, Winter Park, FL, 32792, 3 beds, 2.5 baths, [object Object]

$2,900/mo

3 beds2.5 baths1,755 sq ft

1492 Broad Wing Ln, Winter Park, FL 32792

Property at 3044 Antique Oaks Cir #178, Winter Park, FL, 32792, 1 bed, 1 bath, [object Object]

$1,299/mo

1 bed1 bath749 sq ft

3044 Antique Oaks Cir #178, Winter Park, FL 32792

Property at 2667 Rook Cv, Winter Park, FL, 32792, 2 beds, 1.5 baths, [object Object]

$1,795/mo

2 beds1.5 baths1,050 sq ft

2667 Rook Cv, Winter Park, FL 32792

Property at 3002 Antique Oaks Cir #99, Winter Park, FL, 32792, 1 bed, 1 bath, [object Object]

$1,300/mo

1 bed1 bath750 sq ft

3002 Antique Oaks Cir #99, Winter Park, FL 32792

Property at 1000 S Semoran Blvd #115, Winter Park, FL, 32792, 2 beds, 2 baths, [object Object]

$1,450/mo

2 beds2 baths1,003 sq ft

1000 S Semoran Blvd #115, Winter Park, FL 32792

Property at 3032 Antique Oaks Cir #149, Winter Park, FL, 32792, 1 bed, 1 bath, [object Object]

$1,450/mo

1 bed1 bath749 sq ft

3032 Antique Oaks Cir #149, Winter Park, FL 32792

Property at 1710 Aster Dr Unit 1710, Winter Park, FL, 32792, 3 beds, 2 baths, [object Object]

$3,200/mo

3 beds2 baths1,664 sq ft

1710 Aster Dr Unit 1710, Winter Park, FL 32792

Property at 2929 Antique Oaks Cir #53, Winter Park, FL, 32792, 1 bed, 1 bath, [object Object]

$1,500/mo

1 bed1 bath749 sq ft

2929 Antique Oaks Cir #53, Winter Park, FL 32792

Property at 1502 Michigan Ave Unit B, Winter Park, FL, 32789, 2 beds, 1 bath, [object Object]

$1,399/mo

2 beds1 bath660 sq ft

1502 Michigan Ave Unit B, Winter Park, FL 32789

Property at 1878 Erudite Way, Winter Park, FL, 32792, 3 beds, 2.5 baths, [object Object]

$2,575/mo

3 beds2.5 baths1,782 sq ft

1878 Erudite Way, Winter Park, FL 32792

Property at 5116 N Woodcrest Dr Unit 5116, Winter Park, FL, 32792, 4 beds, 2 baths, [object Object]

$2,475/mo

4 beds2 baths1,427 sq ft

5116 N Woodcrest Dr Unit 5116, Winter Park, FL 32792

Property at 2037 Canny Cv, Winter Park, FL, 32792, 3 beds, 2.5 baths, [object Object]

$2,395/mo

3 beds2.5 baths1,782 sq ft

2037 Canny Cv, Winter Park, FL 32792

Property at 2617 Eastbrook Blvd - 2617 Eastbrook Blvd, Winter Park, FL, 32792, 1-2 bed, 1 bath, [object Object]

$1,200+/mo

1-2 bed1 bath850-900 sq ft

2617 Eastbrook Blvd

| 2617 Eastbrook Blvd, Winter Park, FL 32792

Property at 2610 Eastbrook Blvd Unit 216, Winter Park, FL, 32792, 2 beds, 1 bath, [object Object]

$1,300/mo

2 beds1 bath850 sq ft

2610 Eastbrook Blvd Unit 216, Winter Park, FL 32792

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Based on information submitted to the MLS GRID as of Fri Dec 05 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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