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Winter Park Homes for Sale

Winter Park, FL is a family friendly, upscale suburban community. The city is located just seven miles northeast of Orlando. Park Avenue has a variety of upscale shops, restaurants, and art galleries. Winter Park Village offers outdoor shopping and restaurants. Popular nightlife attractions include Luma, Prato, Cocina 214, and Boca. Central Park has beautiful fountains, a rose garden, and seasonal events. Homes in Winter Park include condos, townhomes, and single family homes. The city is home to Rollins College, a private coed liberal arts school founded in 1885.

View Winter Park Properties

Explore all properties for sale in Winter Park, FL in the greater Orlando area listed below. As you search through listings please be sure to contact us with any questions or to schedule a viewing.

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1566 Minnesota Avenue Winter Park FL 32789
For Rent

MLS Number O6143729

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Lawndale
  • Square Feet 762

To schedule a showing or submit an application, please visit our company website and click on “Available Homes”. This lovely 2 bedroom, 2 bathroom condo is located in the heart of Winter Park. Enjoy all Downtown Winter Park has to offer, 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 tile throughout the main living area, dining room, spacious kitchen, utility room with washer/dryer hookups, and a carport. We are here to make your time in the home as enjoyable and convenient as possible. We offer a safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, 24/7 emergency maintenance response team, and well-maintained homes. Please note the listed amenities may not be accurate.

Listing Courtesy of REAL PROPERTY MANAGEMENT AND REALTY

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Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1400 Formosa Formosa Avenue Winter Park FL 32789
For Rent

MLS Number O6135675

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Stansbury Estates
  • Square Feet 700

1/1 Apartment. Completely remodeled and updated apartment in very desirable 32789, convenient to downtown Orlando, I4 and Advent Health Orlando. New paint, new flooring, new doors and trim, window treatments, paver driveway, stainless appliances , quartz countertops, Central Air, etc. Private yard and double parking. Landlord pays garbage and water. This is one half of a duplex but as you can see in the pictures, you have your own side of the house with a private entrance. Pets on a case by case basis.

Listing Courtesy of LEERDAM PROPERTIES INC.

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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851 Miles Avenue Winter Park FL 32789
For Rent

MLS Number S5091696

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Aragon Condo
  • Square Feet 808

Great location in Winter Park. Walk to restaurants, movies or shopping. Close to Park Avenue, Rollins College, Winter Park Village and the list goes on!! This 2 bedroom 1 bath has good storage in each of the bedrooms. There is a community pool and one assigned parking space for each unit. Guest parking and street parking available if more than one car.

Listing Courtesy of SHELDON PROFESSIONALS INC

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3002 Antique Oaks Circle Winter Park FL 32792
For Rent

MLS Number O6143450

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Parkview Village
  • Square Feet 749

This beautiful one-bedroom, one bath second floor condo is located in the Parkview Village community near Semoran Boulevard and Aloma Avenue. Recently renovated throughout, the condominium offers an expansive feeling with the kitchen open to the living room and dining area. Enjoy new flooring throughout the unit. Off to the side of the living area is a sliding glass door that leads to the private patio, a perfect spot to enjoy your morning cup of coffee. The kitchen hosts a full suite of stainless steel appliances including the refrigerator, range, microwave, dishwasher, disposal and brand new cabinetry and granite counter tops. The master bedroom is spacious and includes a large walk-in closet with plenty of shelving. Across the hall is the bathroom that features a shower-tub combo. Rounding out this wonderful condo is the interior laundry closet that includes a full sized washer and dryer, and water, sewer and trash are included in the rental amount! This property will be fully managed by the property owner during the lease term.

Listing Courtesy of INNOVATIVE REALTY,LLC

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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7338 Swallow Run Winter Park FL 32792
Pending

MLS Number O6140452

  • Rental
  • Mls Status Pending
  • Area Winter Park/Aloma
  • Subdivision Whisperwood Condo 02
  • Square Feet 774

This charming 2-bedroom, 2-bathroom condominium is available for rent in the peaceful community of Swallow Run, Winter Park, Florida. The unit boasts two spacious bedrooms, providing ample space for comfortable living. The master bedroom features plush carpet flooring, while the second bedroom enjoys the same tile flooring as the rest of the house. Both bathrooms have been tastefully remodeled, ensuring a clean and modern aesthetic. The kitchen is equipped with stainless steel appliances, giving it a sleek and contemporary feel. Recessed lights provide excellent illumination for cooking and entertaining. Enjoy the convenience of an in-unit washer and dryer, making laundry chores a breeze. Tenants are responsible for energy, water, internet, and cable services, giving you the flexibility to choose your preferred providers. There is ample parking space available within the community, ensuring that you and your guests always have a convenient place to park. The Swallow Run community offers a refreshing pool for residents to enjoy on those warm Florida days. The air conditioning system was replaced in 2021, providing efficient and reliable cooling throughout the year. This condominium offers a comfortable and contemporary living space in a desirable Winter Park location. Don't miss the opportunity to make this beautiful unit your new home. Contact us today to schedule a viewing.ituated on the first floor, this unit offers both convenience and modern amenities to enhance your living experience.

Listing Courtesy of DOUGLAS EDMUND REAL ESTATE LLC

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$
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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1300 Indiana Avenue Winter Park FL 32789
For Rent

MLS Number O6123202

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Metzingers Add
  • Square Feet 550

Available now! Cozy and quaint (1/2 duplex) unit! 1 Bed/1.5 Bath located in Winter Park!!! This unit has been lovingly renovated last year with new kitchen cabinets, appliances, granite counters, new fans, lights, sink, and so much more!! Stackable washer/dryer included for your convenience. Hard wood floors in the living room and dining room, with tile in kitchen. TWO closets. Bathroom was also renovated. AC system is 2 years old. New Roof too. Small pets ok. Water is included. This lovely property is a charmer! Property is located in a Great Area, Close to Shopping, Restaurants, Winter Park Village, Rollins College, Park Avenue, Local Winter Park Hospitals, and I-4. This property will not last long! Submit your application today!! Renters Insurance Required. Must Obtain and Show Proof Prior to Move In Date. By applying for this eligible property, Resident understands and agrees to auto-enrollment in the Utility & Maintenance Reduction Program, which includes AC filters being shipped to the property. Additional Fees Apply: Administration Fee $250 Pet Privilege Application Fee: $20 Pet Privilege Fee: $250/ On Time Fee, per pre-approved pet Pet Privilege Rent: $25/Monthly, per pre-approved pet Utilities & Maint Program: $15/mo (All Fees are subject to change without prior notice) Please Note: Applicant(s) maybe subject to HOA application fees, deposits, rules, policies, procedures, and processes. All County does not accept responsibility for HOA rental fees and/or board approval process.

Listing Courtesy of ALL COUNTY CFL PROPERTY MGMT

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$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3048 George Mason Avenue Winter Park FL 32792
For Rent

MLS Number O6139041

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Colonies
  • Square Feet 803

Location location location! Perfect for a student or single who wants to be close to Full Sail University or UCF. The condo is located in a prime area and has a super market in the same plaza. The community has a pool,

Listing Courtesy of HONEST REAL ESTATE COMPANY

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$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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851 Miles Avenue Winter Park FL 32789
For Rent

MLS Number O6142095

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Aragon Condo
  • Square Feet 808

Available Oct 1, 2023.......This 2 bedroom 1 bath apartment is located on the 1st floor. Newly renovated interior. Walking distance to grocery shopping and restaurant. The community offers pool and onsite laundry room for a fee. One assigned parking per unit. Water is included in the monthly rent. HOA approval is required before move in. A separate HOA application fee is $100.

Listing Courtesy of MAY HO REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1000 S Semoran Boulevard Winter Park FL 32792
For Rent

MLS Number O6136130

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,049
  • Year Built 1969

Spacious Condo in Winter Park!! Affordable and Centrally Located. This property features 2 Bedroom 2 Baths assigned parking, community pool, community laundry room. Right of Semoran Blvd. Second floor unit, with lots of natural light. Steps away from Full Sail University, Aloma Ave, Restaurants, Convenient stores, Hospitals, Golf Corse, Highway 408, Orlando International Airport and many more. Roommates are welcome!!! Call for a private showing!! Rental Insurance Required. DISCLAIMER - Information deemed reliable but not guaranteed.

Listing Courtesy of PREMIUM PROPERTIES R.E SERVICE

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1000 S Semoran Boulevard Winter Park FL 32792
For Rent

MLS Number O6139981

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,049
  • Year Built 1969

LOCATION, LOCATION, LOCATION! Centrally located near from Full Sail University, UCF, Winter Park, Downtown Orlando, Mills/50 Area, shopping, restaurants, MCO, highways. Come check out this cute and quaint 2 bed/2 bath unit, located on the second floor. You will be immediately greeted by a kitchen and living room combination. The master bedroom comes with an on suite bathroom. Community amenities include a pool, clubhouse, and mailroom.

Listing Courtesy of ALLIANCE RENTAL HOMES

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1000 S Semoran Boulevard Winter Park FL 32792
For Rent

MLS Number O6111391

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,049
  • Year Built 1969

Wonderful second floor unit you are greeted with a combination kitchen/living room. The master bedroom features an on suite bathroom that has been remodeled. Next, the second bedroom is generous in size as well and the secondary bathroom is located in the hallway with easy access. NO WASHER AND DRYER COMMUNITY OFFER LAUNDRY FACILITY. The community offer fantastic pool for residents. Golf Side Villa Condos is conveniently located within few minutes to Full Sail University and UCF, and short distance to Winter Park/ Downtown Orlando world class shopping, dining, and entertainment.

Listing Courtesy of DOUGLAS EDMUND REAL ESTATE LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2183 Crandon Avenue Winter Park FL 32789
Pending

MLS Number O6127996

  • Rental
  • Mls Status Pending
  • Area Winter Park
  • Square Feet 600
  • Year Built 1953

To schedule a showing or submit an application, please visit our company website and click on “Available Homes”. This is a nicely updated ground floor unit with 2 bedrooms and 1 bathroom near downtown Winter Park. Features include large bedrooms, laminate flooring throughout, an updated kitchen, a screened in patio area, and a shared utility room with washer/dryer. We are here to make your time in the home as enjoyable and convenient as possible. We offer a safe and secure online portal where you can submit maintenance requests and pay online with multiple payment options, 24/7 emergency maintenance response team, and well-maintained homes. Please note the listed amenities may not be accurate.

Listing Courtesy of REAL PROPERTY MANAGEMENT AND REALTY

$
$
%
$/month over payments
Federal 30-year interest rate: 7.19% last updated on Sep 21, 2023
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Based on information submitted to StellarMLS as of September 27, 2023 . All data is obtained from various sources and has not been, and will not be, verified by broker or StellarMLS. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing.