Winter Park, FL Homes for Rent under $2,900

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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

  Joseph LaRosa LA ROSA REALTY LLC

  2523 Alexa Ct, Winter Park, FL 32792
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  /15

  $2,590 per month

  • 4 Beds
  • 3 Baths
  • 1,856 Sq Ft
  • House for Rent

  2029 Taylor Ave, Winter Park, FL 32792

  Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

  2029 Taylor Ave, Winter Park, FL 32792
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  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  1994 Canny Cove, Winter Park, FL 32792

  This beautiful three bedroom, two and a half bath townhome is located in the newly developed Grayson Square, a gated community in Winter Park. High-speed Internet and cable are included. There are no rear neighbors, so you will enjoy relaxing on your back porch with a beautiful water view. As you enter the home, the entrance leads to the large kitchen and living area. The kitchen features

  Vildan Nigro RIVA REALTY GROUP LLC

  1994 Canny Cove, Winter Park, FL 32792
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  /2

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  2206 Bonanza Ave, Winter Park, FL 32792

  Property Id: 2450072Welcome to your cozy room in Winter Park, FL! This single-family property offers 1 bedroom and 1 bathroom with all utilities included. Amenities include washer/dryer, dishwasher, and central A/C. Enjoy the convenience of a driveway and no pets allowed. Don't miss out on this gem for $1100/month!

  2206 Bonanza Ave, Winter Park, FL 32792
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  $1,650 per month

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

  1695 Lee Rd Unit C216, Winter Park, FL 32789

  Available for immediate move-in, this comfortable second-floor corner condo offers a peaceful setting with playground and pool views. The home features a fully carpeted interior, a spacious kitchen with a pantry closet, and a newer refrigerator. Washer and dryer are included for added convenience. Great balcony for relaxing on the cooler Florida days! Located in desirable Winter Park, you'll

  Yarmmys Vargas ZEN LIVING HOMES LLC

  1695 Lee Rd Unit C216, Winter Park, FL 32789
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  /15

  $2,600 per month

  • 3 Beds
  • 2.5 Baths
  • 1,525 Sq Ft
  • House for Rent

  3021 Dikewood Ct, Winter Park, FL 32792

  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 ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  3021 Dikewood Ct, Winter Park, FL 32792
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  /14

  $1,395 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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  /15

  $2,315 per month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  1407 Chilean Ln, Winter Park, FL 32792

  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 ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  1407 Chilean Ln, Winter Park, FL 32792
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  /19

  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • House for Rent

  1931 Carrigan Ave, Winter Park, FL 32792

  An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not

  Amanda Beckman RED DOOR INVESTMENT GRP LLC

  1931 Carrigan Ave, Winter Park, FL 32792
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  /15

  $2,249 per month

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  1453 Hyde Park Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2393.90. That covers your base rent, $2249.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1453 Hyde Park Dr, Winter Park, FL 32792
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  $1,250 per month

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

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

  Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

  SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

  2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
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  /15

  $2,440 per month

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • House for Rent

  3091 Crane Strand Dr, Winter Park, FL 32792

  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 ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  3091 Crane Strand Dr, Winter Park, FL 32792
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  $2,800 per month

  • 5 Beds
  • 3 Baths
  • 1,945 Sq Ft
  • House for Rent

  3642 Periwinkle Dr, Winter Park, FL 32792

  Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income. The main home features a freshly painted interior and exterior, new LVP flooring throughout,

  John Hwangbo HONEST REAL ESTATE COMPANY

  3642 Periwinkle Dr, Winter Park, FL 32792
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  /13

  $2,220 per month

  • 3 Beds
  • 2 Baths
  • 1,479 Sq Ft
  • House for Rent

  1185 Village Forest Place, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2364.90. That covers your base rent, $2220.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1185 Village Forest Place, Winter Park, FL 32792
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  $1,950 per month

  • 2 Beds
  • 2.5 Baths
  • 1,236 Sq Ft
  • Townhouse for Rent

  5169 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to Lazy Oaks condominium. This townhome features two levels with an open floor plan that consist of 2 bedrooms, 2.5 bathrooms, and a Florida Room. Over 1200 sqft of living space awaits you with an upgraded laminate flooring, baseboards, lighting, and ceiling fans. A prime location that is nestled near Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando

  Damon Mayers MAYERS REAL ESTATE LLC

  5169 Lazy Oaks Dr, Winter Park, FL 32792
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  /15

  $2,610 per month

  • 4 Beds
  • 2 Baths
  • 1,641 Sq Ft
  • House for Rent

  1790 Viburnum Ln, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2874.90. That covers your base rent, $2610.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1790 Viburnum Ln, Winter Park, FL 32792
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  /12

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  1565 Michigan Ave, Winter Park, FL 32789

  Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

  Troy Hensley BHHS FLORIDA REALTY

  1565 Michigan Ave, Winter Park, FL 32789
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  /19

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  3221 Thistle Hill Dr, Aloma, FL 32792

  This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee (subject to approval).

  3221 Thistle Hill Dr, Aloma, FL 32792
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  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • House for Rent

  1148 Park Green Place, Winter Park, FL 32789

  Single family home in Winter Park! Close to shopping, theater, malls! Single family three bedroom two bath home Fully tiled interior, all appliances including washer and dryer. Fenced courtyard and patio. Two car garage with remote! Home is currently occupied. Call ahead for showing appointments

  Linda Baez DON ASHER & ASSOCIATES, INC.

  1148 Park Green Place, Winter Park, FL 32789
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  /11

  $1,380 per month

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

  2942 Antique Oaks Cir Unit 82, Winter Park, FL 32792

  Property Id: 1010517Second Floor one bedroom unit in the highly desirable Parkview Condominium Complex across from Full Sail University. The rent includes water and sewer. All floors are laminate.

  2942 Antique Oaks Cir Unit 82, Winter Park, FL 32792
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  $2,435 per month

  • 3 Beds
  • 1.5 Baths
  • 1,351 Sq Ft
  • House for Rent

  1622 Arbor Park Dr, Winter Park, FL 32789

  Free 1/2 month's rent move in incentive! Come view this 3 bed/1.5 bath home in Winter Park! With easy access to Lake Howell Rd and Lakemont Ave, it's close to several restaurants, surrounded by schools, parks, and lakes, Interlachen Country Club, AdventHealth, and Kraft Azalea Garden. Aloma and Old Winter Park are also nearby. Inside, you'll find a large living room with plenty of natural light

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  1622 Arbor Park Dr, Winter Park, FL 32789
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  /17

  $2,625 per month

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • House for Rent

  6877 Jackman Blvd, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  6877 Jackman Blvd, Winter Park, FL 32792
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  /13

  $2,495 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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  /20

  $1,650 per month

  • 1 Bed
  • 1 Bath
  • 502 Sq Ft
  • House for Rent

  1550 Michigan Ave, Winter Park, FL 32789

  Welcome to your future home in the charming district of Winter Park, FL! This inviting property offers a warm atmosphere perfect for relaxation and convenience, surrounded by a vibrant community.This residence boasts spacious living equipped with essential comforts. With ample bedrooms and bathrooms, it accommodates various lifestyles. You'll appreciate the central heating and cooling

  1550 Michigan Ave, Winter Park, FL 32789
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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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  /19

  $2,230 per month

  • 3 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • House for Rent

  5484 Park Vale Blvd, 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 features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

  5484 Park Vale Blvd, Winter Park, FL 32792
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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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  $850 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  2206 Bonanza Ave, Winter Park, FL 32792

  Property Id: 2445485Room for rent in a beautiful home located at 2206 Bonanza Ave, Winter Park, FL 32792, situated in a quiet and safe neighborhood—ideal for students or professionals. Features:•Private room with a digital lock •Clean home with a peaceful atmosphere•Shared kitchen, living room, and laundry facilities•WiFi and utilities included (water, electricity,

  2206 Bonanza Ave, Winter Park, FL 32792
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  $2,600 per month

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft
  • House for Rent

  1655 Sunnyside Dr, Maitland, FL 32751

  Welcome to this charming residence nestled on a picturesque corner lot in the heart of Maitland. Located along classic brick-lined streets, this 3-bedroom, 2-bathroom home offers 1,418 square feet of thoughtfully designed living space filled with warmth, character, and timeless appeal. From the moment you arrive, the inviting curb appeal, mature landscaping, and welcoming front porch set the tone

  Melquisedec Martins NOVA REAL ESTATE SERVICES INC

  1655 Sunnyside Dr, Maitland, FL 32751
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  /19

  $2,420 per month

  • 3 Beds
  • 2 Baths
  • 1,653 Sq Ft
  • House for Rent

  1891 Aster 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 features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at This home is priced to rent

  1891 Aster Dr, Winter Park, FL 32792
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  $1,900 per month

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft
  • Townhouse for Rent

  2510 Boyd Ave Unit b, Orlando, FL 32803

  Experience the allure of this meticulously renovated one-bedroom and bathroom apartment unit. This open-concept space features a granite countertop and stainless steel appliances, providing a modern and inviting atmosphere. Additionally, the unit includes an extra room, ideal for an office, with direct access to the private backyard. Conveniently located near Baldwin Park, downtown Orlando, and a

  Antonio Velazquez LPT REALTY, LLC

  2510 Boyd Ave Unit b, Orlando, FL 32803
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  $2,695 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Townhouse for Rent

  7518 Aloma Pines Ct, Winter Park, FL 32792

  Welcome to 7518 Aloma Pines Ct, a modern 3-bedroom, 2.5-bath townhome in the heart of Winter Park, FL. Set in a quiet, gated community, this 1,872 sq ft residence blends upscale living with smart home features — including a built-in 5.1 surround sound system for a theater-quality experience.Interior Highlights:•Chef’s kitchen with granite countertops, 42” wood cabinetry, stainless

  7518 Aloma Pines Ct, Winter Park, FL 32792
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  /19

  $1,000 total monthly price

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • House for Rent

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space

  5058 Seminole Ave Unit Seminole Unit 2, Winter Park, FL 32792
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  $1,550 total monthly price

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

  1695 Lee Rd Unit B106, Winter Park, FL 32789

  Ground Floor condo - Hardwood and Tile floors throughout! Available TODAYHardwood and Tile throughout! Ceiling fans ! lots of natural light! condo offers a peaceful setting with courtyard and pool views. no carpeted interiors. a galley-style kitchen with all appliances included. Stackable Washer and dryer are included . Great patio area for relaxing. Located in desirable Winter Park, you'll

  1695 Lee Rd Unit B106, Winter Park, FL 32789
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  $2,900 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  5417 Ferrol Dr, Winter Park, FL 32792

  Beautifully Remodeled 3 Bed, 2 Bath Home Energy Efficient & Prime Location!Welcome to your dream rental! This stunning newly remodeled 3-bedroom, 2-bath home offers modern comfort with a touch of elegance. Featuring an open floor concept, the spacious living area is perfect for entertaining, complete with a cozy fireplace and abundant natural light from double-glazed windows.The

  5417 Ferrol Dr, Winter Park, FL 32792
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  $1,000 - $1,700 per month

  District On Baldwin Park

  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

  5590 Baldwin Park St, Orlando, FL 32807
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  $2,195 per month

  • 2 Beds
  • 1 Bath
  • 1,146 Sq Ft
  • House for Rent

  1730 Ridgewood Ave, Maitland, FL 32751

  Property Id: 1799893LOCATION, LOCATION, LOCATION! Fabulous cottage in the heart of Winter Park / Maitland. This charming 1,146sf, 2-bedroom, 1-bath home is just off N Park Ave, it's close to Orlando Ave, Whole Foods, Publix, and in walking distance to The Enzian. The home sits with an expansive back yard with beautiful mature trees and a barbeque patio. It includes a detached garage with

  1730 Ridgewood Ave, Maitland, FL 32751

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