Winter Park, FL Homes for Rent under $2,000

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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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  $1,250 - $1,800 per month

  Park Apartments

  1 - 3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two

  7528 Park Promenade Dr, Winter Park, FL 32792
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  $1,575 per month

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

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  2 Bedroom/2 Bathroom 2nd Floor Unit at Lancelot. Location, Location, Location... with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping. This 2nd floor end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar.

  Kelly Carr CFRP REALTY LLC

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792
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  $1,219 - $1,717 total monthly price

  Solis at Winter Park

  1 - 2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  7502 Sun Key Blvd, Winter Park, FL 32792
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  $1,499 per month

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792

  2-bedroom, 1.5-bathroom, two-story condo in Four Seasons Condos of Winter Park. This well maintained condo includes a French country kitchen, which has been renovated with a faux tiled backsplash, custom maple cabinets, and complimentary appliances. This unit includes a half bath downstairs and full bathroom upstairs. Windows are double-pane, double-hung with a Pella sliding glass door with

  Amy Spano WILSON MANAGEMENT GROUP

  200 Saint Andrews Blvd Unit 1803, Winter Park, FL 32792
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  $1,297 - $1,918 total monthly price

  Atlas at Winter Park

  1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  $1,300 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  3212 Netherwood Dr, Winter Park, FL 32792

  This 400sqft QUICK MOVE in-law suite, with kitchen, bedroom and bathroom, along with living room space. Water and electricity are included with your rent. Laundry on-site. Suitable for 2-person occupancy.

  Sara Cruz FLORIDA HOMES REALTY & MORTGAGE

  3212 Netherwood Dr, Winter Park, FL 32792
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  $1,695 - $1,825 per month

  The Lofts of Winter Park Village

  1 Bed

  520 N Orlando Ave, Winter Park, FL 32789

  Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

  520 N Orlando Ave, Winter Park, FL 32789
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  $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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  $1,474 - $1,761 per month

  POSTE Winter Park

  1 - 2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, 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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  $1,750 - $2,750 per month

  Hannibal Square

  2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  433 W New England Ave, Winter Park, FL 32789
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  $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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  $1,300 - $1,855 per month

  La Aloma

  1 - 3 Beds

  3040 Aloma Ave, Winter Park, FL 32792

  La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

  3040 Aloma Ave, 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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  $1,052 - $1,721 per month

  Carlton Arms of Winter Park

  Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  Carlton Arms of Winter Park is a well established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff. We offer an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, 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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  $1,892 - $2,806 total monthly price

  Rosalia Winter Park 55+ Active Adult Community

  1 - 2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar-all with an attentive team at your

  3045 Aloma Ave, Winter Park, FL 32792
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  $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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  $1,378 - $2,138 per month

  Westmount at Winter Park

  Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  1701 Lee Rd, 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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  $1,320 - $2,745 per month

  Signal Pointe

  1 - 3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, 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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  $1,236 - $2,425 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, Winter Park, FL 32789
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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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  $956 - $1,356 per month

  Golden Oaks

  2 - 3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
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  $1,314 - $2,763 per month

  Alvista Winter Park

  1 - 2 Beds

  3935 Sutton Place Blvd, Winter Park, FL 32792

  Live life better at Alvista Winter Park! Located in the sought-after neighborhood of Winter Park, Orlando, and just minutes from Full Sail University, Harbor Park and Winter Pines Golf Club, our community effortlessly blends the concepts of convenience and ease. Our collection of lifestyle amenities and interior details make our residents quickly feel right at home!Choose from spacious one and

  3935 Sutton Place Blvd, Winter Park, FL 32792
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  $1,471 - $2,620 per month

  Stonecastle Apartment Homes

  1 - 3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  $1,375 total monthly price

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

  2500 Lee Rd Unit 212, Winter Park, FL 32789

  Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

  2500 Lee Rd Unit 212, Winter Park, FL 32789
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  $1,469 - $2,654 per month

  ARIUM Winter Park

  1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  3250 Bishop Park Dr, Winter Park, FL 32792
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  $800 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  2206 Bonanza Ave, Winter Park, FL 32792

  Property Id: 2450077Welcome to your cozy single-family room in Winter Park, FL! This 1 bedroom, 1 bathroom property at 2206 Bonanza Ave offers modern amenities such as dishwasher, washer/dryer, and central air. Rent includes electricity, internet, and water. No smoking or pets allowed. Don't miss out on this gem for $800/month!

  2206 Bonanza Ave, Winter Park, FL 32792
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  $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

  • 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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  $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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  $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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  $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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  $1,950 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,090 Sq Ft
  • House for Rent

  1613 Winter Green Blvd, Winter Park, FL 32792

  Charming Single-Family Home in the Heart of Winter ParkWelcome home to this well-maintained 3-bedroom, 2-bath single-family residence located in a quiet, established Winter Park neighborhood. Enjoy the privacy of a detached home, abundant natural light, and a functional layout perfect for comfortable everyday living.The home features fresh, neutral interiors, updated bathrooms,

  1613 Winter Green Blvd, 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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