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Condos for Rent in Winter Park, FL with 2-Bedrooms

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    $1,850

    Total Monthly Price

    • 2 Beds
    • 2 Baths
    • 1,026 Sq Ft
    • Condo for Rent

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

    Two-bedroom, two-bath second-floor condo in a quiet, private lakefront community in Winter Park, Florida. Spacious rooms, custom upgrades, and well-maintained. Located in the Chateaux du Lac community, it is blocks from the Winter Park Village, Trader Joe's, Publix, and multiple restaurants and retail shops. Minutes by car to Advent Health Orlando Hospital, Park Avenue, Rollins College, and

    1500 Gay Rd Unit 9D, Winter Park, FL 32789
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    $2,550 Per Month

    • 2 Beds
    • 2 Baths
    • 1,140 Sq Ft
    • Condo for Rent

    110 Killarney Bay Ct Unit 1, Winter Park, FL 32789

    **MOVE IN SPECIAL $500 off first months rent** Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
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    $2,825

    Total Monthly Price

    • 2 Beds
    • 1 Bath
    • Condo for Rent

    662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789

    The advertised rate of $2,826/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 2, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789
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    $1,300 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit D213, Winter Park, FL 32789

    Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

    Rachel DeCamp RLL Real Estate Group

    1695 Lee Rd Unit D213, Winter Park, FL 32789
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    $1,749 Per Month

    • 2 Beds
    • 2 Baths
    • 964 Sq Ft
    • Condo for Rent

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

    3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792
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    $1,500 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit B114, Winter Park, FL 32789

    The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit B114, Winter Park, FL 32789
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    $1,595 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • SPACIOUS 2BR CONDO | MOVE-IN READY | LIMITED AVAILABILITY

    1695 Lee Rd, Winter Park, FL 32789

    Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community.This unit offers the perfect combination of comfort, space, and convenience — ideal for families or professionals looking for a clean and functional home ready for immediate move-in.PROPERTY HIGHLIGHTS:2 Bedrooms / 1 Full Bathroom - Second-floor unit

    1695 Lee Rd, Winter Park, FL 32789
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    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,037 Sq Ft
    • Condo for Rent

    625 Trinidad Ct Unit 625, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Move right into this CLEAN & WELL-MAINTAINED 2 BEDROOM / 2 BATH ONE-STORY CONDO offering 1,037 SF OF COMFORTABLE LIVING SPACE in the heart of WINTER PARK! This MOVE-IN READY home features a SPACIOUS LAYOUT, NATURAL LIGHT, and a functional floor plan perfect for comfortable everyday living. Enjoy a SMALL & COZY BACKYARD PATIO AREA, perfect for

    Nydia Marrero ZEN LIVING HOMES LLC

    625 Trinidad Ct Unit 625, Winter Park, FL 32792
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    $1,495 Per Month

    • 2 Beds
    • 2 Baths
    • 1,045 Sq Ft
    • Condo for Rent

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

    LB/O - Nice 2 bedroom 2 bathrooms, 2nd Floor Unit, Open Floor Concept, Living Area, Breakfast Area, Community Pool, Water Included! Apply Today!TO SCHEDULE A SHOWING YOU MUST EMAIL US WITH YOUR CONTACT INFORMATION AND THE PROPERTY YOU WISH TO SEE AT AND AN AGENT WILL RESPOND BACK WITH THE AVAILABLE SHOW TIMES.HOW TO APPLY/ABOUT OUR APPLICATION PROCESS: Our application process

    1000 S Semoran Blvd Unit 806, Winter Park, FL 32792
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    $1,650 Per Month

    • 2 Beds
    • 2 Baths
    • 1,003 Sq Ft
    • Condo for Rent

    1000 S Semoran Blvd Unit 815, Winter Park, FL 32792

    This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home

    Scott Butts KIMBRIDGE REALTY, LLC

    1000 S Semoran Blvd Unit 815, Winter Park, FL 32792
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    $1,595 Per Month

    • 2 Beds
    • 2 Baths
    • 1,104 Sq Ft
    • Condo for Rent

    3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792

    Great location! Spacious SECOND FLOOR 2 bedroom + 2 full bath condo featuring an open living room/dining room combo and large kitchen. Conveniently located across from the pool. Stackable washer/dryer in unit. NEW CARPET in bedrooms! Parking permit required. Two pet max permitted. Available now! NOTE: Petscreening required on all applications, whether tenant has a pet or not. . $30 per pet to

    3011 George Mason Ave Unit 1-2E, Winter Park, FL 32792
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    $1,745 Per Month

    • 2 Beds
    • 1 Bath
    • 865 Sq Ft
    • Condo for Rent

    1941 Lanier Ct, Winter Park, FL 32792

    This first floor, 2 bedroom, 1 bathroom condo is located in the heart of Winter Park. Enjoy all of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include an open main living area, lovely kitchen with granite countertops and stainless steel

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    1941 Lanier Ct, Winter Park, FL 32792
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    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Newly remodeled 2/2 condo Winter Park $300. incentive for move in by 6/15/2026

    3651 N Goldenrod Rd Unit A104, Winter Park, FL 32792

    This 2 bedroom two bath condo has been remodeled with new tile flooring, new bathrooms and all new appliances including Washer and dryer as well as kitchen appliances, stove, fridge, dishwasher, and microwave. Community has a large community pool right outside your door. Great location with access to major roads, great dining venues and shopping possibilities. Ready for move in now. Come

    3651 N Goldenrod Rd Unit A104, Winter Park, FL 32792
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    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Condo for Rent

    3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792

    Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and

    Praveen Setty RIGHTHOUSE REALTY LLC

    3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
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    $1,700 Per Month

    • 2 Beds
    • 2 Baths
    • 1,059 Sq Ft
    • Excellent location

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

    This roomy condo is available for immediate occupancy. New Luxury Vinyl Plank floors just installed. The unit is ideally located in Winter Park, not far from Full Sail or UCF. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room. Call today for your private tour of this amazing

    4968 Tangerine Ave Unit 4968, Winter Park, FL 32792
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    $1,360 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Condo for Rent

    3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792

    This is a 2 bedroom, 2 bathroom, second floor condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include a spacious main living area, a lovely kitchen, vaulted ceilings, spacious bedrooms, and a laundry closet. Community amenities include a pool, gym, and clubhouse. Schedule a showing or submit an application online. All Real Property Management &

    Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792
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    $1,800 Per Month

    • 2 Beds
    • 2 Baths
    • 927 Sq Ft
    • Condo for Rent

    205 Lewfield Cir Unit 205, Winter Park, FL 32792

    Wonderful! Owners pays Water & Internet. Exceptional Winter Park location! Amenities include 2 pools, lighted tennis courts, fitness center, car care facilities & clubhouse, enjoy the simple life in this 2 bedroom, 2 bath, ground floor unit. Sip your morning coffee while admiring the garden landscaping from your screen enclosed patio. Host a barbeque with family and friends at the community

    Eimi Moreno Carrera LPT REALTY, LLC

    205 Lewfield Cir Unit 205, Winter Park, FL 32792
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    $1,740 Per Month

    • 2 Beds
    • 2 Baths
    • 1,036 Sq Ft
    • Condo for Rent

    7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792

    Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792
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    $1,595 Per Month

    • 2 Beds
    • 1 Bath
    • 881 Sq Ft
    • Condo for Rent

    1695 Lee Rd Unit C206, Winter Park, FL 32789

    Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community. This unit offers the perfect combination of comfort, space, and convenience — ideal for families or professionals looking for a clean and functional home ready for immediate move-in. PROPERTY HIGHLIGHTS:2 Bedrooms / 1 Full Bathroom - Second-floor unit (added privacy) -

    Yein Ross ROSS RENTALS LLC

    1695 Lee Rd Unit C206, Winter Park, FL 32789
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    $1,500 Per Month

    • 2 Beds
    • 2 Baths
    • 802 Sq Ft
    • Condo for Rent

    7340 Swallow Run Unit 7340, Winter Park, FL 32792

    Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

    Bobby Mills METRO CITY REALTY

    7340 Swallow Run Unit 7340, Winter Park, FL 32792

Rental Home Trends in Winter Park, FL

Rental Home Trends

Number of 2 Bedroom Condos for Rent
20
Median 2 Bedroom Condo Rent
$1,663
Median 2 Bedroom Townhouse Rent
$1,795
How to Rent a Home