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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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1000 S Semoran Boulevard Winter Park FL 32792
For Rent

MLS Number O6248063

  • 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. The community amenities include: pool, club house. The HOA fee includes:, water, sewage, maintenance, and more. 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

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Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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 O6267959

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,003
  • Year Built 1969

This ground-floor 2-bedroom, 2-bathroom condo offers a spacious open floor plan, generously sized bedrooms, and numerous upgrades. The kitchen features tile flooring, stainless steel appliances, wood cabinets, and custom lighting, seamlessly blending into the living area. Sliding glass doors open to a private, fully fenced patio. Both bedrooms boast luxury vinyl flooring, ample closet space, and additional storage. Community amenities include a pool and an on-site laundry facility. Conveniently located near Full Sail University, UCF, Cady Way Trail, Park Avenue's shops and restaurants, and Baldwin Park. Come schedule a tour of your future home today! Prospective residents must obtain approval from the Condo Association Board of Directors.

Listing Courtesy of ALLIANCE RENTAL HOMES

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$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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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1512 Indiana Avenue Winter Park FL 32789
For Rent

MLS Number R4908685

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Lawndale
  • Square Feet 960

Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and dining room and Kitchen complete with all appliances included and great counter space. The master bedroom is spacious and bright with a large walk-in closet that also leads into the bathroom! Bathroom with shower. Washer and dryer combo included! Just a mile away from the amazing night with gorgeous restaurants, bar and shopping, and fun in the the heart of Winter Park! APARTMENT HAS THE OPTION TO RENTAL WITH FURNITURE AND WITHOUT FURNITURE.

Listing Courtesy of LAWHUN ENTERPRISES IV,LLC DBA: FLORIDA REALTY INVESTMENTS IV

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$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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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3651 N Goldenrod Road Winter Park FL 32792
For Rent

MLS Number O6261920

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Lancelot/winter Park
  • Square Feet 840

HALF OFF 1st FULL MONTHS RENT! 2 Bed/2 Bath in Winter Park - $1500 mo/$1500 dep - AVAILABLE NOW! This 2nd floor, 2bedroom/2 bath is an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar. The unit has been freshly painted and all new kitchen appliances, as well as a Washer and Dryer. All Tile Flooring. Granite Counter is kitchen and baths. Great Seminole County Schools and the location can't be beat! Community features a pool/clubhouse. Excellent school zone which includes desirable Winter Park School High School, Glenridge Middle School. An ideal location that makes a Great Rental Investment property or owner occupied. 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. EQUAL HOUSING OPPORTUNITY

Listing Courtesy of CFRP REALTY LLC

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$
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$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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 O6221851

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Metzingers Add
  • Square Feet 610

Available NOW!! Cozy and quaint 1/2 duplex unit! 1 Bed/1 Bath located in Winter Park!!! This unit has been lovingly renovated 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 3 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 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: 6.96% last updated on Jan 23, 2025
* 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 St Andrews Boulevard Winter Park FL 32792
For Rent

MLS Number O6263126

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Four Seasons Condo
  • Square Feet 727

Located in the heart of Winter Park, this 1-bedroom, 1-bathroom rental offers the perfect combination of convenience and charm. Just minutes from Downtown Winter Park, Rollins College, and Downtown Orlando, you'll enjoy easy access to a vibrant array of restaurants, shops, and entertainment options. This home features a spacious family/living room area, a dedicated dinette, and a relaxing screened-in porch. The property includes a community laundry facilities for added convenience. The community offers amenities such as a pool, perfect for relaxing or socializing with neighbors. Outdoor enthusiasts will appreciate the proximity to local parks, the Winter Park Chain of Lakes, and the stunning Botanical Gardens. Whether you're dining at nearby restaurants or exploring the best of Winter Park and Orlando, this rental's prime location puts it all within reach. Schedule a showing today to see this incredible opportunity!

Listing Courtesy of EXP REALTY LLC

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$
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$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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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Winter Park FL 32792

Winter Park, FL

Rental Price$1,400

For Rent

MLS Number S5117931

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Square Feet 1,020
  • Year Built 1974

Available 2 bedroom and 2 bathroom home in the desired area the Winter Park. Great location near the airport, Schools, and shopping center.

Listing Courtesy of TRANSCONTINENTAL REALTY GROUP

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$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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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4816 Tangerine Avenue Winter Park FL 32792
For Rent

MLS Number O6274027

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Wrenwood Condo
  • Square Feet 753

Winter Park Condo AVAILABLE NOW! This 1 bedroom 1 bath is in an established neighborhood. All Kitchen appliances, living room/dining area combo, inside utility room with washer and dryer included. 1 Dedicated Parking Space. Conveniently located at SR436 and Aloma, 408, 417 and I-4. The community offers a Clubhouse and Pool. EQUAL HOUSING OPPORTUNITY

Listing Courtesy of CFRP REALTY LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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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3069 Aaron Burr Avenue Winter Park FL 32792
For Rent

MLS Number S5118849

  • Rental
  • Mls Status Active
  • Area Winter Park/Aloma
  • Subdivision Colonies
  • Square Feet 537

Enjoy this 1 bedroom 1 bathroom condo located at The Colonies in Winter Park. Close to UCF, Full Sail University and centrally located to shopping malls, major highways, restaurants and theme parks. Just 11 minutes from Orlando international Airport. This cozy 1 bedroom is perfect for a quick access to all that Orlando has. New carpet and a clean fresh home to make a perfect lifestyle for anyone

Listing Courtesy of ACKLEY FLORIDA PROPERTY MANAGEMENT INC

$
$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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 O6270687

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Waterfall Cove
  • Square Feet 638

Charming 1-bedroom, 1-bathroom condo with an in-unit washer & dryer in the desirable Waterfall Cove community of Winter Park. Enjoy the serene, park-like surroundings and take advantage of the community's exceptional amenities, including a sparkling pool and scenic walking paths. Conveniently located near Winter Park Village, local dining, shopping, and beautiful lakes, this home offers the best of both comfort and location. Don't miss the opportunity to make this beautiful condo yours

Listing Courtesy of MTRE GROUPE LLC

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$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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 O6269410

  • Rental
  • Mls Status Active
  • Area Winter Park
  • Subdivision Waterfall Cove
  • Square Feet 881

Spacious two-bedroom, one bath condo available now! This is a second-floor apartment with a spacious living room and dining room and a great patio off of the living area! Kitchen complete with all appliances included and great counter space. The first bedroom has a nice space with a double-door closet. The master bedroom is spacious and bright with a large walk-in closet that also leads into the bathroom! Bathroom with tub and shower combo and extra storage space! Washer and dryer combo included! Just a mile away from great food, shopping, and fun in Winter Park!

Listing Courtesy of FLORIDA REALTY INVESTMENTS

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$
%
$/month over payments
Federal 30-year interest rate: 6.96% last updated on Jan 23, 2025
* 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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2929 Antique Oaks Circle Winter Park FL 32792
For Rent

MLS Number O6248601

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

MOVE IN SPECIAL! Please contact Innovative Realty for more information! This beautiful one-bedroom, one bath 749 sqft second floor condo is located in the Parkview Village community near Semoran and Aloma. The condominium offers an expansive feeling with the kitchen open to the living room and dining area. 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 overlooks the living and dining room and contains a suite of appliances including the refrigerator, range, disposal and plenty of cabinet space. The bedroom is spacious and includes a large walk-in closet. Across the hall is the bathroom that features the spacious tiled-shower and an oversize vanity. Rounding out this wonderful condo is the interior laundry closet that includes a washer and dryer. Water, sewer and trash are included in the rental amount! Renters insurance is required for this property. 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: 6.96% last updated on Jan 23, 2025
* 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 January 26, 2025 . 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.