Winter Park, FL Homes for Sale under $500,000

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  /47

  $480,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,808 Sq Ft

  1593 Lawndale Cir, Winter Park, FL 32792

  Beautifully renovated 3 bedroom 2.5 bath pool home located in the lake-centric community of Country Lane in Winter Park. Residents enjoy exclusive access to Lake Florence, offering kayaking, fishing, and scenic outdoor recreation just moments from home. Perfectly positioned on a premium lot with ample space, this property combines privacy, modern upgrades, and exceptional indoor-outdoor

  Daniel Hsieh EXP REALTY LLC

  1593 Lawndale Cir, Winter Park, FL 32792
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  /12

  $499,000

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft

  230 Strathy Ln, Winter Park, FL 32792

  Completely Remodeled Winter Park Home – Prime LocationBeautifully updated single-family home located in the heart of Winter Park. This residence was fully remodeled in 2019, offering peace of mind with new kitchen and appliances, updated bathrooms, new flooring, HVAC system, electrical, and plumbing.Ideally situated directly across from Advent Health Winter Park Hospital, this property

  David Auerbach PARK TOWN REAL ESTATE LLC

  230 Strathy Ln, Winter Park, FL 32792
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  /2

  $500,000

  • 4 Beds
  • 3 Baths
  • 2,031 Sq Ft

  2054 Eastbrook Blvd, Winter Park, FL 32792

  Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced backyard. Zoned for Lake Howell High School.

  Melissa Stalzer LPT REALTY, LLC

  2054 Eastbrook Blvd, Winter Park, FL 32792
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  /18

  $269,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  2317 Sun Valley Cir, Winter Park, FL 32792

  Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence nestled in the heart of Winter Park! Step inside to an inviting living room with a vaulted ceiling. The fully equipped open-floor kitchen, featuring ample roomy cabinets, is perfect for everyday living and entertaining. The thoughtfully designed split floor plan enhances functionality and privacy. Elegant,

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  2317 Sun Valley Cir, Winter Park, FL 32792
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  /57

  $405,000

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft

  5503 Albert Dr, Winter Park, FL 32792

  No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof

  Fernando Perez de Armas AXEN REALTY, LLC

  5503 Albert Dr, Winter Park, FL 32792
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  /36

  $269,900

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  2384 Sun Valley Cir, Winter Park, FL 32792

  Great opportunity to own this 3 bedrooms, 2 bathrooms single-story, ground level, end unit condo located within the quaint community of Cedarwood Village with a desirable Winter Park address! This light and bright home features vaulted ceilings in the living room, creating an open and airy feel. The kitchen offers an eat-in space, stainless steel appliances, a convenient pass through to the

  Anna Lohr URBANISTA BROKERS

  2384 Sun Valley Cir, Winter Park, FL 32792
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  /50

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 1,656 Sq Ft

  1850 Aster Dr, Winter Park, FL 32792

  Welcome to the heart of Winter Park.This beautifully maintained 4-bedroom, 2.5-bath pool home offers the perfect blend of warmth, functionality, and charm. From the moment you arrive, the curb appeal is unforgettable. Lush landscaping, mature greenery, and peaceful natural surroundings create a private and inviting setting that immediately feels like home. Inside you'll find an open and welcoming

  Kimberly English EXP Realty, LLC

  1850 Aster Dr, Winter Park, FL 32792
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  /43

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  512 N Lakemont Ave, Winter Park, FL 32792

  Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity.The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space

  David Plasencia COLDWELL BANKER REALTY

  512 N Lakemont Ave, Winter Park, FL 32792
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  /25

  $220,000

  $30K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 927 Sq Ft

  205 Lewfield Cir Unit 205, Winter Park, FL 32792

  MOTIVATED SELLER! Wonderful! 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 BBQ with family and friends at the community clubhouse or enjoy

  Eimi Moreno Carrera LPT REALTY, LLC

  205 Lewfield Cir Unit 205, Winter Park, FL 32792
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  /32

  $259,000

  Open Fri 11AM - 2PM $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  2383 Sun Valley Cir, Winter Park, FL 32792

  Nestled in a peaceful setting within the serene Cedarwood Village community, this charming one-story Winter Park condo offers a quiet retreat away from traffic noise, with a rear wooden fence for no visible neighbors for added privacy. The spacious 27-foot tiled and enclosed lanai creates the perfect place to relax and enjoy the tranquil surroundings. Cedarwood Village also offers low-maintenance

  Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

  2383 Sun Valley Cir, Winter Park, FL 32792
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  /37

  $395,000

  $15K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft

  340 Killarney Bay Ct Unit 4-4, Winter Park, FL 32789

  Welcome to 340 Killarney Bay, a beautifully maintained residence located within one of Winter Park’s most charming and sought-after communities. With access to Lake Killarney, residents enjoy a waterfront community pool, dock, and a peaceful setting that perfectly complements the relaxed Winter Park lifestyle. This home offers a spacious and inviting layout with both bedrooms located upstairs for

  Blaike Gill KELLER WILLIAMS WINTER PARK

  340 Killarney Bay Ct Unit 4-4, Winter Park, FL 32789
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  /31

  $475,000

  $65K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  346 S Ranger Blvd, Winter Park, FL 32792

  PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone

  Tetyana Vyushkina IMPERIAL REALTY OF FLORIDA INC

  346 S Ranger Blvd, Winter Park, FL 32792
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  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  /25

  $427,400

  $23K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  220 Alpine Dr, Maitland, FL 32751

  Opportunity in the Maitland / Winter Park area! This one-owner home, held by the same family since the 1960s, is ideally located near shopping, dining, parks, and major roadways, providing convenient access throughout Central Florida.The property offers potential for renovation, expansion, or redevelopment, with a lot that provides space for future improvements. Ideal for homeowners,

  Beth Hathaway PREMIUM PROPERTIES R.E SERVICE

  220 Alpine Dr, Maitland, FL 32751
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  /20

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,146 Sq Ft

  1033 Hamlet Dr, Maitland, FL 32751

  This charming 3-bedroom, 2-bathroom single-family home with the best of Florida living. Located in the north of Orlando (Maitland - Winter Park area). 1.3 miles to the Center of Winter Park Shopping Plaza (Office Depot, UPS, Ross, Marshalls, Home Goods, Five Below, LA Fitness, Petco and Michaels, Whole Foods Markets, and Banking). Access to major highways, minutes to downtown, and Orlando's

  Bennie Olivo BOX REAL ESTATE LLC

  1033 Hamlet Dr, Maitland, FL 32751

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