Winter Park, FL Homes under $500,000

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  $440,000

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft

  1621 Puritan Ave, Winter Park, FL 32792

  Down Payment Assistance Available! Welcome to 1621 Puritan Ave, a beautifully renovated pool home located in the highly desirable Winter Park area on the Seminole County side. This property qualifies for multiple down payment assistance programs, making it an excellent opportunity for first-time buyers. Recent upgrades include a new roof (2023), resurfaced pool (2023), and an updated A/C system

  Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
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  $449,000

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

  Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box located just steps from Park Avenue. This fully renovated, one-bedroom, one-bathroom condo offers 900 ft2 of single-story, ground-floor, corner-unit living. The 2018 full renovation was extensive and included new electrical re-wiring and plumbing. The scope of the renovation extended to creating new conditioned space,

  Padgett McCormick KELLY PRICE & COMPANY LLC

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
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  $429,900

  • 4 Beds
  • 4 Baths
  • 1,934 Sq Ft

  3128 Patel Dr, Winter Park, FL 32792

  Don't miss this income producing duplex just minutes from University Ave and the UCF area! The separate units are 2 bedroom, 2 bath on each side and include ceramic tile/laminate flooring, spacious living room, kitchen with appliances, spacious closets, ceiling fans, washer/dryer hookups, and spacious fenced back yard.The property is currently rented on a month to month basis at

  Keith Race FUSILIER MANAGEMENT GROUP

  3128 Patel Dr, Winter Park, FL 32792
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  $425,000

  • Land
  • 0.11 Acre
  • $3,863,636 per Acre

  786 W Canton Ave, Winter Park, FL 32789

  Incredible opportunity for the right family. This is a 49x96 Perfectly high and dry lot with a tree to shade your backyard. Nestled in the highly sought after City of Winter Park amongst million dollar homes. LOCATION LOCATION LOCATION! A perfect home site for your future custom dwelling. Bring your imagination creativity and builder to take a look. What a Winter Park sweet spot. Lots in this

  Laurie Cash Cain CHARLES RUTENBERG REALTY ORLANDO

  786 W Canton Ave, Winter Park, FL 32789
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  $495,000

  • Land
  • 0.16 Acre
  • $3,093,750 per Acre

  1414 Bessmor Rd, Winter Park, FL 32789

  ?? Land for Sale – Build Your Dream Home in Winter Park! Just minutes from Park Avenue!Discover the perfect opportunity to build your custom home in one of Central Florida’s most desirable neighborhoods! This prime homesite is nestled among newly built luxury residences and offers the ideal canvas for your future home.The owner has already completed the heavy lifting — the previous

  Miranda Azer PARKVIEW REAL ESTATE

  1414 Bessmor Rd, Winter Park, FL 32789
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  $475,000

  • Land
  • 0.14 Acre
  • $3,392,857 per Acre

  Unlisted Address

  Fabulous location in one of Winter Park's most sought-after neighborhoods. Orwin Manor features tree-lined streets and historical homes just minutes from Park Ave, Hannibal Square, Rollins College, premier restaurants and shoppes, and quick access to I-4.

  Julie Wright CHARLES RUTENBERG REALTY ORLANDO

  Unlisted Address
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  /2

  $499,000

  • Land
  • 0.13 Acre
  • $3,838,462 per Acre

  621 Symonds Ave, Winter Park, FL 32789

  Great opportunity for a R-2 lot in heart of downtown Winter Park - opportunity to purchase adjacent lot at 631 Symonds and combine

  Emily Williams FANNIE HILLMAN & ASSOCIATES

  621 Symonds Ave, Winter Park, FL 32789
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  /2

  $499,000

  • Land
  • 0.13 Acre
  • $3,838,462 per Acre

  631 Symonds Ave, Winter Park, FL 32789

  Great R-2 lot in the heart of downtown Winter Park - lot next door 621 Symonds also available for purchase and opportunity to combine.

  Emily Williams FANNIE HILLMAN & ASSOCIATES

  631 Symonds Ave, Winter Park, FL 32789
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  $469,990 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2949 Clever Ln, Winter Park, FL 32792

  Welcome to this stunning former model townhome built in 2023, ideally located in the highly sought-after gated community of Grayson Square in Winter Park, Florida. This beautifully designed residence offers a blend of modern finishes and functional layout, with the first floor featuring a completely open floor plan bathed in natural light. The spacious kitchen boasts quartz countertops, upgraded

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  2949 Clever Ln, Winter Park, FL 32792
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  $469,900 Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 1,801 Sq Ft

  2037 Canny Cove, Winter Park, FL 32792

  Nestled in the coveted Grayson Square community of highly desired Winter Park, FL, 2037 Canny Cove Lane is a contemporary 3-bedroom, 2.5-bath townhome built in 2023. The open-concept layout features a stylish kitchen with stainless steel appliances, quartz countertops, and ample storage, seamlessly flowing into the spacious gathering room. The owner's suite offers a private retreat with an

  Claire Sims LLC LPT REALTY, LLC

  2037 Canny Cove, Winter Park, FL 32792
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  /5

  $419,000

  • Land
  • 0.15 Acre
  • $2,793,333 per Acre

  1830 Lake Sue Dr, Orlando, FL 32803

  Incredible Opportunity to Build Your Dream Home in Audubon Park! This rare 55’ x 115’ cleared lot offers a prime location to create your perfect home in the heart of the vibrant Audubon Park neighborhood. Just a short stroll to the beautiful Leu Gardens and the lively shops, restaurants, and bars along Corrine Drive. Zoned for the highly sought-after Audubon K-8 and Winter Park High School, this

  Stacy Wright MEGAN DOWDY REALTY, LLC

  1830 Lake Sue Dr, Orlando, FL 32803
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  $409,900

  • 3 Beds
  • 2 Baths
  • 1,885 Sq Ft

  2625 Queen Mary Place, Maitland, FL 32751

  Auction Property. Located in desirable Brittany Gardens, this home offers spacious living areas and a smart, open floorplan — perfect for customization and renovation. Step inside to find a large great room, ideal for entertaining. The generously sized master suite features a luxurious bathroom with a soaking tub, separate shower enclosure, and dual vanities. Additional bedrooms are

  Wade Stafford ALL FLORIDA PROPERTY GROUP,INC

  2625 Queen Mary Place, Maitland, FL 32751

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