Newest Homes for Rent in Winter Park, FL

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  $3,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • House for Rent

  438 Lakeview Ave, Winter Park, FL 32789

  Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete

  Alex Scures COLONIALTOWN REALTY

  438 Lakeview Ave, Winter Park, FL 32789
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  /49

  $6,600 Per Month

  • 5 Beds
  • 4 Baths
  • 2,918 Sq Ft
  • House for Rent

  2075 Jewell Ave, Winter Park, FL 32789

  FULLY FURNISHED and move in ready elegant home.A rare find in Winter Park. 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the

  

  Paul Jimenez

  URBANISTA BROKERS

  2075 Jewell Ave, Winter Park, FL 32789
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  $2,200 Per Month

  • 3 Beds
  • 1 Bath
  • 1,500 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
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  $6,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Apartment for Rent

  301 W Comstock Ave, Winter Park, FL 32789

  Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

  Sydney Brownlee THE SYDGAN CORP

  301 W Comstock Ave, Winter Park, FL 32789
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  /16

  $1,400 Per Month

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C110, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C110, Winter Park, FL 32789
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  /25

  $5,490 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,354 Sq Ft
  • Condo for Rent

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the

  Steven Koleno BEYCOME OF FLORIDA LLC

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
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  /19

  $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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  /19

  Starting at $1,250 Per Month

  • 1 - 2 Beds

  2610-2617 Eastbrook Blvd, Winter Park, FL 32792

  Nestled within the serene and picturesque neighborhood of Lake Howell, Eastbrook Apartments offers a peaceful lakeside living experience with all the conveniences of a big city. This charming community in the Winter Park area is ideal for those seeking a blend of tranquility and accessibility. With 29 exclusive units, Eastbrook provides an intimate living environment with spacious and

  Eastbrook Apartments

  2610-2617 Eastbrook Blvd, 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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  /20

  $1,600 Per Month

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Townhouse for Rent

  2523 Alexa Ct, Winter Park, FL 32792

  Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

  Bernardo Reynoso LA ROSA REALTY LLC

  2523 Alexa Ct, Winter Park, FL 32792
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  $1,350 Per Month

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Condo for Rent

  2500 Lee Rd Unit 244, Winter Park, FL 32789

  Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

  

  Rustina Gibson

  RE/MAX VANTAGE

  2500 Lee Rd Unit 244, Winter Park, FL 32789
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  /12

  $1,300

  Total Monthly Price

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

  1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789

  Centrally located 2/1 apartment. Near Shopping, gas, churches, golf, convenience store, park and much more. Across the street is Orlando. Hardwood floors. Over 100 restaurants within 1 mile. Easy on and off I-4. Good neighbors. No pets.

  1360 Formosa Ave Unit 1360 Formosa, Winter Park, FL 32789
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  /13

  $2,295 Per Month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792

  Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792
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  $2,950

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 1,118 Sq Ft
  • House for Rent

  779 W Lyman Ave, Winter Park, FL 32789

  Charming 3BR/2BA Home in the Heart of Winter Park – Walk to Park Ave & Hannibal Square!Discover this cozy and well-maintained 3-bedroom, 2-bathroom home nestled in one of Winter Park’s most desirable neighborhoods. Just a short stroll to Park Avenue and Hannibal Square, you'll enjoy premier shopping, dining, and entertainment right at your doorstep.This home features a private, fully

  779 W Lyman Ave, Winter Park, FL 32789
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  Starting at $910 Per Month

  • 1 - 3 Beds

  2353 Winter Woods Blvd, Winter Park, FL 32792

  Come home to San Jose Apartments and enjoy the advantages of spacious apartments and ample parking. We have a wide variety of living spaces to choose from, all with large closets and modern amenities. You'll love our beautiful swimming pool and clubhouse. Call today to make San Jose Apartments your new home.TDD:711 for hearing impaired assistance.

  San Jose Apartments

  

  2353 Winter Woods Blvd, Winter Park, FL 32792
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  $2,530 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,397 Sq Ft
  • Townhouse for Rent

  1839 Blaine Terrace, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

  1839 Blaine Terrace, Winter Park, FL 32792
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  $3,300 Per Month

  • 3 Beds
  • 1 Bath
  • 820 Sq Ft
  • House for Rent

  853 W Lyman Ave, Winter Park, FL 32789

  Property Id: 1403118Our home is convenient for your extended friends and family, remote workers, traveling nurses, Rollins College parents and alum, snowbirds, conference attendees, or exploring travelers who prefer to stay in our home away from home.Three bedrooms (one queen and two double beds) accommodate three couples, Living room has large sectional and flat screen TV (bring

  853 W Lyman Ave, Winter Park, FL 32789
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  /19

  $2,780 Per Month

  • 4 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • House for Rent

  5219 Ardmore Dr, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home is priced to rent and won't be around for long. Apply now, while we make this home ready for you, or call to arrange a meeting with your local Progress Residential leasing specialist

  5219 Ardmore Dr, Winter Park, FL 32792
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  /20

  $3,873

  Total Monthly Price

  • 3 Beds
  • 2 Baths
  • 990 Sq Ft
  • Condo for Rent

  2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789

  The advertised rate of $3,874/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 18, 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

  2007 Cornell Ave Unit SI ID1032296P, Winter Park, FL 32789
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  /13

  $1,250

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 615 Sq Ft
  • Condo for Rent

  2037 Linden Rd Unit 2037 linden rd unit A, Winter Park, FL 32792

  Mother in law suite 1 bd /1 bath 613 Sqf Nice neighborhood, washer and dryer. Parking Garage Cable, internet, Electricity. Include in the rent Not Smoking. Small pet. Cat. Independent Entrance Door

  2037 Linden Rd Unit 2037 linden rd unit A, Winter Park, FL 32792
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  $1,850

  Total Monthly Price

  • 2 Beds
  • 2.5 Baths
  • 1,100 Sq Ft
  • Condo for Rent

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

  Close to Park Avenue Winter Park Restaurants and shopping near UCF and Full sail University also Rollins Colllege, Great Public schools. Close to the Orlando Airport and 30 minutes from Disney World and Universal Studios.

  2924 Antique Oaks Cir Unit 48, Winter Park, FL 32792
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  Starting at $1,000 Per Month

  • Studio - 3 Beds

  5590 Baldwin Park St, Orlando, FL 32807

  Join us at District on Baldwin Park in Orlando, where you'll revel in luxurious apartment living and resort-style amenities minutes from shopping, entertainment, restaurants and recreation. Lounge by one of our three sparkling pools, sip a cup of coffee and surf the net in our Internet cafe?? or chat with neighbors over cards in our clubhouse. At District on Baldwin Park, you get the resort

  District On Baldwin Park

  5590 Baldwin Park St, Orlando, FL 32807
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  $2,000 Per Month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789

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