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2-Bedroom Condos for Rent in Winter Park, FL

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  • /20

    $2,622 per month

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

    1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

    Welcome to this cozy and inviting 2-bedroom, 1-bathroom home, perfect for couples, small families, or solo travelers eager to explore Central Florida. Situated just 3 miles from Downtown Orlando, 12 miles from Universal Studios, and 8 miles from Disney, this location is unbeatable.This charming property features two spacious queen bedrooms, a full bathroom with a walk-in shower, and a working

    1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
  • /22

    $1,475 per month

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

    2500 Lee Rd Unit 115, Winter Park, FL 32789

    Experience comfort and leisure in this charming 2-bedroom, 1-bathroom condo nestled within a highly sought-after lakefront community on picturesque Lake Killarney. Offering 851 sq. ft. of thoughtfully designed living space, this residence features modern upgrades including newer appliances, wood laminate flooring, and can come furnished. Ideally located less than a mile from I-4, the property

    Nicole Howell FANNIE HILLMAN & ASSOCIATES

    2500 Lee Rd Unit 115, Winter Park, FL 32789
  • /20

    $1,695 per month

    • 2 Beds
    • 2.5 Baths
    • 1,230 Sq Ft
    • Condo for Rent

    7296 Daniel Webster Dr Unit 1, Winter Park, FL 32792

    Welcome to 7296 Daniel Webster Dr Unit 1, a spacious and well-kept 2-bedroom, 2.5-bath townhome offering 1,230 sq ft of comfortable living in the heart of Winter Park. The main floor features a bright living and dining area with wood-style flooring, a half bath, a dedicated laundry room with washer/dryer hookups, and a beautifully updated kitchen with rich wood cabinetry, granite countertops, and

    7296 Daniel Webster Dr Unit 1, Winter Park, FL 32792
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    $1,750 per month

    • 2 Beds
    • 2 Baths
    • 1,066 Sq Ft
    • Condo for Rent

    3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792

    Great rent . First flour . Two bedrooms' and two bathroom in great quite safe community. 3 miles from SAM Wearhouse. Its clean and ready to move in.

    Amin Abraham FLORIDA REALTY INVESTMENTS

    3057 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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    $1,725 per month

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

    851 Miles Ave Unit 21, Winter Park, FL 32789

    Enjoy a quiet but beautiful space at Aragon Condominiums. This first-floor corner unit allows for privacy with only one adjoining neighbor. It is a perfect place to call home with upgrades all around, including granite countertops, washer and dryer in unit, and a community pool just right outside your door. It is conveniently located in Winter Park, where you can enjoy many shops, restaurants,

    Richard Traynor FLORIDA ONE REAL ESTATE LLC

    851 Miles Ave Unit 21, Winter Park, FL 32789
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    $1,650 per month

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

    1250 S Denning Dr Unit 233, Winter Park, FL 32789

    Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open

    Samuel Kingsford STOCKWORTH REALTY GROUP

    1250 S Denning Dr Unit 233, Winter Park, FL 32789
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    $2,599 per month

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Condo for Rent

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792

    FURNISHED CORPORATE/EXECUTIVE RENTAL "THE FLORENCE" ,TOWNHOUSE COMMUNITY BOAST 2 BED/2.5 BATH EXECUTIVE CONDO IN THE HIDDEN OAKS COMMUNITY, WINTER PARK FLORIDA. THIS ELEGANT HOME FEATURES 1031 SQ. FT. OF LIVING SPACE, AND COMMUNITY POOL. 32'' AND 90" CABINETS IN THE SCANDINAVIAN DESIGNED KITCHEN. PORCELAIN TILE FLOORS IN THE KITCHEN AND BATHROOMS. FULLY EQUIPPED LAUNDRY ROOM FOR YOUR CONVENIENTLY

    Darryl Henderson, Jr GLOBAL ENTERPRISE REALTY GROUP

    3254 Oak Lake Place Unit 137, Winter Park, FL 32792
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    $1,600 per month

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

    1250 S Denning Dr Unit 232, Winter Park, FL 32789

    Less than 1 mile from Rollins College and Park Ave in the highly desirable 32789 Winter Park zip code. This 2-Bedroom, 2-Bath hidden gem backs up to Mead Botanical Gardens. Also, less than 5 miles from from Downtown Orlando. This light-filled home features a brand-new kitchen with granite countertops & appliances, fresh paint, updated bathrooms, new carpet, and modern finishes throughout.

    Robert Isaac Rodriguez RE/MAX DOWNTOWN

    1250 S Denning Dr Unit 232, Winter Park, FL 32789
  • /58

    $4,850 per month

    • 2 Beds
    • 2 Baths
    • 1,143 Sq Ft
    • Condo for Rent

    104 S Interlachen Ave Unit 114, Winter Park, FL 32789

    Welcome to the Cloisters, an exclusive lakefront condominium community in Winter Park, now available for lease. This first-floor two-bedroom, two-bath residence offers a thoughtfully updated open-concept layout and direct garden access. Entering from the main hallway, you step into a welcoming interior where the kitchen sits to the right, featuring a breakfast bar that connects seamlessly to the

    Drew Henner PREMIER SOTHEBY'S INTL. REALTY

    104 S Interlachen Ave Unit 114, Winter Park, FL 32789
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    $2,400 per month

    • 2 Beds
    • 2.5 Baths
    • 1,495 Sq Ft
    • Condo for Rent

    2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792

    Welcome to 2340 Sun Valley Circle, Winter Park, FL 32792, a stylish 2-bedroom, 2-bath condo featuring a bonus loft that’s perfect for a office or guest space. Step into an updated layout boasting vaulted ceilings, modern luxury flooring, a remodeled kitchen, and a sleek, refreshed bathroom that feels both contemporary and timeless. In-unit laundry, two dedicated parking spaces, and smart,

    Melissa Johnson EXP REALTY LLC

    2340 Sun Valley Cir Unit 2340, Winter Park, FL 32792
  • /15

    $1,850 per month

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

    1250 S Denning Dr Unit 105, Winter Park, FL 32789

    Welcome to your dream home in the heart of Winter Park! This beautifully updated 2-bedroom, 2-bath condo offers the perfect blend of style, comfort, and convenience. Just steps away from Mead Gardens, fantastic restaurants, cozy coffee shops, vibrant cocktail bars, and so much more, you’ll love the walkable and bikeable lifestyle. Park Avenue is only minutes away, making it easy to enjoy

    Joe Devlin DEVLIN INVESTORS & ASSOCIATES

    1250 S Denning Dr Unit 105, Winter Park, FL 32789
  • /20

    $1,500 per month

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

    2500 Lee Rd Unit 235, Winter Park, FL 32789

    Comfort and recreation in this charming 2-bedroom, 1-bathroom condo. Located in a sought-after lakefront community on Lake Killarney, you'll enjoy 851 sq. ft. of modern living with stainless steel appliances, wood laminate flooring, and a new, efficient AC. Enjoy the convenience of being less than a mile from I-4 while maintaining the tranquility of a quiet, safe neighborhood. Step outside and

    Laura Heredia NEW HEIGHTS REALTY GROUP

    2500 Lee Rd Unit 235, Winter Park, FL 32789
  • /20

    $1,705 per month

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

    851 Miles Ave Unit 8, Winter Park, FL 32789

    UNBELIEVABLE PRICE DROP! This gorgeous 2 bedroom 1 bathroom condo is ready to go, and priced for you! This unit is a second floor corner condo, located in the serene and peaceful Aragon Condo community. Centrally located in Winter Park, only 5 minutes to downtown, Rollins College, Orlando Health and so much more. Featuring an open floor plan, stainless steel appliances, wood flooring throughout,

    Michael Mones LPT REALTY, LLC

    851 Miles Ave Unit 8, Winter Park, FL 32789
  • /15

    $1,840 per month

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

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

    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 within reach of central Florida's vibrant offerings. Strategically positioned minutes from the

    David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

    7429 Daniel Webster Dr Unit 14 (C), Winter Park, FL 32792
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    $1,550 per month

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

    1695 Lee Rd Unit D212, Winter Park, FL 32789

    This great second floor two-bedrooms 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

    giuseppina moriconi GM SUNSHINE REALTY LLC

    1695 Lee Rd Unit D212, Winter Park, FL 32789
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    $1,895 per month

    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft
    • Condo for Rent

    7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792

    Come view this 2 bed, 2.5 bathroom home located in the beautiful Winter Park area. This home is located in a great area with close proximity to shopping, restaurants, multiple freeways, Full Sail, UCF, etc. Each bedroom are large in space and have their own private en-suite bathroom. On the first floor, you’ll find an open concept with views of the newer kitchen with granite counterops, living

    Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

    7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792
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    $1,599 per month

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

    225 Lewfield Cir, Winter Park, FL 32792

    Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent dining area includes a stackable washer/dryer and flows into a modern kitchen with floor-to-ceiling

    Steve Simpson 407 PROPERTIES

    225 Lewfield Cir, Winter Park, FL 32792
  • /19

    $1,600 per month

    • 2 Beds
    • 2 Baths
    • 1,031 Sq Ft
    • Condo for Rent

    3267 Forest Oaks Ct Unit 111, Winter Park, FL 32792

    LOCATION, LOCATION, LOCATION! This well-maintained 2-bedroom, 2-bath condo available for rent is perfectly situated near Full Sail University, UCF, Valencia College, Rollins College. The home features an eat-in kitchen, a spacious great room, a convenient storage room, and a tranquil rear patio—ideal for relaxing outdoors. Enjoy easy access to bike trails, shopping, dining, churches, retail

    Praveen Setty RIGHTHOUSE REALTY LLC

    3267 Forest Oaks Ct Unit 111, Winter Park, FL 32792
  • /23

    $1,795 per month

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

    851 Miles Ave Unit 9, Winter Park, FL 32789

    Imagine living in this completely renovated two-bedroom, one-bathroom second-floor condominium unit near downtown Winter Park at Aragon Condos. This intimate, two-building, two-story condominium community comprises just twenty-eight units focused around a central courtyard.Features include: • Recently remodeled kitchen including all cabinetry, countertops, marble tile backsplash,

    Richard Traynor FLORIDA ONE REAL ESTATE LLC

    851 Miles Ave Unit 9, Winter Park, FL 32789
  • /25

    $1,600 per month

    • 2 Beds
    • 1.5 Baths
    • 1,085 Sq Ft
    • Condo for Rent

    316 Scottsdale Square Unit 316, Winter Park, FL 32792

    Welcome to 316 Scottsdale Square, a delightful 2-bedroom, 1 and half bathroom condo located in desirable Winter Park. This home features a spacious open floor plan with natural light, ideal for comfortable living. The kitchen includes modern appliances and overlooks the cozy living area, perfect for entertaining. The utility room is equipped with a washer and dryer, plus extra storage space for

    Tyann Huynh JADE KEY REALTY LLC

    316 Scottsdale Square Unit 316, Winter Park, FL 32792
  • /22

    $1,399 per month

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

    3651 N Goldenrod Rd Unit B109, Winter Park, FL 32792

    Welcome home! This fantastic 2 bedroom, 2 bath Condo is available for move in on July 8th, 2025! You will love this fabulous condo in the charming and great central location of Winter Park /East Orlando. The 2 bedroom, 2 bath condo offers a spacious living and dining combo, with an open floor paln, large kitchen with lots of cabinet and storage space!! There are Sizable closet space in both

    Steve Simpson 407 PROPERTIES

    3651 N Goldenrod Rd Unit B109, Winter Park, FL 32792
  • /25

    $1,595 per month

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Condo for Rent

    7449 Wynnewood Square Unit 182, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Come home to this charming townhome in Winter Park! This beautifully maintained 2 bedroom, 2.5 bath home offers the perfect blend of comfort, convenience, and privacy. Step inside to an inviting open floor plan ideal for entertaining or simply relaxing at home. The spacious kitchen features a cozy eating area, perfect for casual meals or morning

    Annette Ortega KELLER WILLIAMS ADVANTAGE 2 REALTY

    7449 Wynnewood Square Unit 182, Winter Park, FL 32792
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    $1,550 per month

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

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

    Welcome to Golfside Villas. This community is nestled near Downtown Orlando, Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando International Airport. This condominium features an open floor plan that consist of 2 bedrooms, 2 bathrooms, and a screened in patio. Over 1000 sqft of living space awaits you with a few upgrades. This neighborhood features a laundry

    Damon Mayers MAYERS REAL ESTATE LLC

    1000 S Semoran Blvd Unit 115, Winter Park, FL 32792
  • /21

    $1,400 per month

    • 2 Beds
    • 2 Baths
    • 1,066 Sq Ft
    • Condo for Rent

    3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792

    Great Investment Opportunity!Updated 2-bed, 2-bath condo in the Colonies community featuring brand-new stainless-steel appliances, granite countertops, walk-in closets, and a new balcony. Enjoy amenities like a pool and playground.Close to UCF, Valencia, and Full Sail, with easy access to dining, shopping, and major highways.Schedule a showing today!

    Paola Ramirez ROBERT SLACK LLC

    3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792
  • /19

    $1,550 per month

    • 2 Beds
    • 2.5 Baths
    • 1,090 Sq Ft
    • Condo for Rent

    3007 George Mason Ave Unit H-3D, Winter Park, FL 32792

    Move-in ready and beautifully updated, this two-story condo in the desirable Colonies Community offers 2 bedrooms and 2.5 bathrooms, with each bedroom featuring its own private en-suite bath. All bedrooms are located upstairs. While a convenient half bath is located on the first floor. The home features fresh interior paint, new flooring in many rooms, and numerous upgrades throughout. The

    Alex Zweydoff ALLEGIANT MANAGEMENT GROUP INC

    3007 George Mason Ave Unit H-3D, Winter Park, FL 32792
  • /45

    $3,300 per month

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Condo for Rent

    690 Osceola Ave Unit 502, Winter Park, FL 32789

    Immaculate renovated lakefront condo with partial views of Lake Virginia and the Downtown skyline. Location, location, location!! Walking distance to Winter Park’s iconic Park Avenue and Rollins College. Open concept living space includes new chef’s kitchen with quartz counter tops, stainless steel Samsung appliances, recessed lighting and expansive bar seating. The large living space allows for

    Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

    690 Osceola Ave Unit 502, Winter Park, FL 32789
  • /23

    $1,650 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 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 location. Don’t miss the

    Yigit Orer EMPIRE NETWORK REALTY

    1695 Lee Rd Unit B114, Winter Park, FL 32789
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