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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.

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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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657 Minnesota Avenue Winter Park FL 32789
For Rent

MLS Number O6175195

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Winter Park
  • Square Feet 1,548

DUPLEX - FANTASTIC WINTER PARK LOCATION. 2 bedroom, 1 bath, with carport on driveway.. PRIVATE FENCED BACKYARD!! Terrazzo floors, Window AC units with ceiling heat. Close to everything Winter Park has to offer, ie, Rollins College, Winter Park village, etc!! Winter Park also is a nature lover's destination. In Winter Park you'll find more than 70 parks, all home to various events, festivals and celebrations throughout the year.

Listing Courtesy of A+ HOME RENTALS LLC

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Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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7749 Fernbrook Way Winter Park FL 32792
For Rent

MLS Number O6178597

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,332
  • Year Built 1984

Discover the joy of Winter Park in this stunning 3-bedroom, 2.5-bathroom townhome. With a thoughtful layout, this home offers both convenience and relaxation at every turn. As you step inside, you're welcomed by a spacious living room and dining area bathed in natural light, perfect for entertaining guests or simply enjoying cozy evenings with loved ones. The first-floor primary bedroom provides an oasis of tranquility, complete with an en-suite bathroom for added privacy and convenience. Venture upstairs to find two generously sized bedrooms, ideal for family members or guests, each offering ample closet space and easy access to a shared hall bathroom. Outside, the options for leisure are endless. Unwind on the shaded and screened front patio, ideal for enjoying your morning coffee or a good book. Alternatively, step into the expansive fenced backyard, where endless opportunities for outdoor recreation and relaxation await. Whether you're hosting a barbecue with friends or simply basking in the sunshine, this outdoor space is yours to personalize and enjoy. Conveniently located in Winter Park, this townhome offers easy access to a wealth of amenities, including shopping, dining, parks, and more. Embrace the vibrant local culture, explore nearby attractions, or simply revel in the tranquility of your own private retreat.

Listing Courtesy of ORLANDO REALTY PROFESSIONALS

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Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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1250 S Denning Drive Winter Park FL 32789
For Rent

MLS Number O6177038

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Mead Garden
  • Square Feet 908

*Newly Remodeled- Fully Upgraded** Second floor unit with beautiful Pool view! 2 bedroom / 2 full bath condo with spacious screened balcony overlooking pool in desirable Mead Gardens Condominiums. Just completed $60,000 interior decorator designed renovation including brand new kitchen, new appliances, new carpet and tile throughout, new light fixtures & ceiling fans, upgraded bathrooms. New paint and window blinds. Central Air.Complex is centrally located- Close to Park Ave, Rollins College, Restaurants, Sunrail, Orlando Art Museum, Science Center & Florida Hospital.

Listing Courtesy of UNITED REAL ESTATE PREFERRED

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Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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1500 Gay Road Winter Park FL 32789
For Rent

MLS Number O6179227

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Chateaux Du Lac
  • Square Feet 1,026

Walk to Winter Park Village for movies, shopping & restaurants! Close to Trader Joe's and Park Avenue! Boat ramp access and fishing pier on Lake Killarney for skiing and water sports. Community pool and clubhouse with expansive lake views. Tenant limited to two vehicles per condo. Move-in Ready 2 bedroom 2 bath second-floor unit with updated a/c unit and hot water heater. Updated kitchen with granite countertops and appliances. Upgraded fixtures and vanities in both bathrooms Tenant must be approved by the association prior to leasing. Laundry facilities provided on-site at clubhouse/pool area. Enjoy a maintenance-free lifestyle close to everything you could ever need!

Listing Courtesy of ACUITY LLC

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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1423 Oneco Avenue Winter Park FL 32789
For Rent

MLS Number O6179338

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Square Feet 864
  • Year Built 1959

This home is located in desirable Winter Park and is a two-bedroom, one-bath home on a 50-by-137 foot lot. Tile throughout main living area, carpet in the bedrooms, neutral color throughout. Large deck off the back of the home. A Carport for your convenience, Laundry room located in carport. Located on the brick portion of Oneco near Sunset Drive.

Listing Courtesy of OLDE TOWN BROKERS INC

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Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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762 Maryland Avenue Winter Park FL 32789
Pending

MLS Number O6172008

  • Rental
  • Mls Status Pending
  • Area Winter Park
  • Subdivision Trotter Rep
  • Square Feet 721

Charming 2 bed/ 1 bath property in sought after Winter Park. Walk to Park Avenue, Sunrail Station, Winter Park Tennis Center and so much more! Terrazzo & tile floors throughout. Freshly painted interior. Indoor laundry room. 2 designated parking spaces, one covered. There is a shared fenced-in backyard space with gazebo.

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

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Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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1695 Lee Road Winter Park FL 32789
For Rent

MLS Number O6180270

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Square Feet 1,149
  • Year Built 1966

Property located in the heart of winter park. Cozy 3 bedroom 2 bath apartment. Apartment is walking distance to winter park village, which offers movies, shopping and many fine dining areas. Updated interior. Lease with option to buy available. Washer and dryer included in the apartment but with no warranties.

Listing Courtesy of SUAREZ REALTY INC.

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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4968 Tangerine Avenue Winter Park FL 32792
For Rent

MLS Number O6160093

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Wrenwood Condo
  • Square Feet 1,059

This roomy 2 bed/2 bath condo was just brightened up with a fresh coat of paint. It is ideally located in Winter Park, not far from Full Sail or UCF. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room.

Listing Courtesy of BENCHMARK REAL ESTATE GRP INC

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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7429 Daniel Webster Drive Winter Park FL 32792
For Rent

MLS Number S5098542

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Colonies
  • Square Feet 1,036

What an Opportunity !! A 2 bedrooms 2 bath condo for rent in Winter Park. The unit is freshly painted ready to move in. It is located within waking distance to a strip mall including a supermarket, beauty saloon, restaurants and much more. Don't miss this opportunity before is gone !!

Listing Courtesy of ROCKER'S REAL ESTATE,LLC

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$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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200 Saint Andrews Boulevard Winter Park FL 32792
Pending

MLS Number O6169320

  • Rental
  • Mls Status Pending
  • Area Winter Park/Aloma
  • Subdivision Four Seasons Condo
  • Square Feet 1,322

Spacious 3 bed, 2 bath condo in sought after Four Seasons. This unit is on the second floor, has an in-unit washer & dryer. Recently painted, screened in balcony, built-in bookcase in family room, large dining room, laminate& tile flooring in living area and kitchen. This community has 2 pools, clubhouse, tennis, shuffleboard & fitness center. Amazing location, 5 minutes to downtown Winter Park/Park Avenue as well as close to shopping, restaurants and Advent Hospital Winter Park. No Pets. Please call for your showing today!

Listing Courtesy of FANNIE HILLMAN & ASSOCIATES

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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280 Scottsdale Square Winter Park FL 32792
For Rent

MLS Number O6174146

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,085
  • Year Built 1974

Discover refined living in this elegantly renovated 2-level, 2-bedroom, 1.5-bath condo, exuding a townhouse charm. The high ceilings throughout the unit amplify the sense of space and enhance the influx of natural light, creating a warm and inviting atmosphere. Each level is adorned with accessible balconies that seamlessly extend your living space outdoors, providing tranquil views of the beautifully landscaped courtyard - ideal for relaxation or hosting guests. The heart of this home is the updated kitchen, where new granite countertops, modern cabinets, high-end stainless steel appliances, and chic porcelain tiling converge to create a culinary haven. Bathrooms have been refreshed with sleek, contemporary vanities. The recent replacement of the hot water heater in 2023 guarantees efficiency and comfort. Notably, the convenience of laundry is just steps away, with the laundry room thoughtfully situated on the balcony. Nestled in a prime location, this condo is within easy reach of Full Sail University and is surrounded by well-known educational institutions including Barry University Dwayne O. Andreas School of Law, Herzing University, Keiser University, University of Central Florida, Rollins College, and Valencia College. The neighborhood is a hub of activity with nearby Costco Wholesale, Walmart, Chili's Grill and Bar, and Firehouse Subs. Situated only 4 miles from Winter Park SunRail Train Station, 20 minutes from Orlando International Airport, and with swift access to major highways, this location is perfect for commuters and explorers alike. Your comfort and convenience are further enhanced by the HOA, which covers water, sewer, trash, and exterior pest control. Immerse yourself in the community's vibrant lifestyle with amenities like pools, tennis courts, a playground, and a clubhouse. For those seeking additional convenience, a carport is available for a fee.

Listing Courtesy of CENTURY 21 EDGE

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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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2517 Windward Way Winter Park FL 32792
For Rent

MLS Number O6182741

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,075
  • Year Built 1975

Cute two bedroom two bath townhouse with screened patio looking to the tennis courts. Close to the pool. New paint and fresh cleaning make it an easy move in. Tile floors throughout, clerestory windows in the living room. 2nd bedroom opens to the porch. There is also storage room on patio.

Listing Courtesy of COLDWELL BANKER REALTY

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$
%
$/month over payments
Federal 30-year interest rate: 6.94% last updated on Feb 29, 2024
* 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 March 6, 2024 . 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.