Winter Park, FL Homes for Sale under $600,000

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  /29

  $499,000

  $51K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,498 Sq Ft

  1652 Berkshire Ave, Winter Park, FL 32789

  Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offering added breathing room, curb appeal, and convenience. A paver walkway leads to the covered front porch, setting the tone for the home’s classic character and welcoming appeal. Inside, original hardwood floors complement a

  Brian Teach COLDWELL BANKER REALTY

  1652 Berkshire Ave, Winter Park, FL 32789
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  /43

  $469,900

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1320 Gladiolas Dr, Winter Park, FL 32792

  Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upgrades include a 10 KW solar panel system, double pane gas insulated windows throughout the house and the enclosed lanai. The kitchen has LG appliances and granite countertops. Both bathrooms have updates as well. The house has

  Deborah Morgan OPTIMA REAL ESTATE

  1320 Gladiolas Dr, Winter Park, FL 32792
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  /28

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,380 Sq Ft

  5316 Halyard Ct, Winter Park, FL 32792

  Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finishes, comfortable living spaces, and an incredible backyard designed for enjoying the Florida lifestyle. From the moment you arrive, you'll appreciate the inviting curb appeal, updated front entry, and thoughtfully maintained

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  5316 Halyard Ct, Winter Park, FL 32792
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  /42

  $390,000

  • 4 Beds
  • 2 Baths
  • 1,607 Sq Ft

  2512 Eastbrook Blvd, Winter Park, FL 32792

  Welcome to this beautifully maintained 4-bedroom, 2.5-bath home located in highly desirable Seminole County! From the moment you arrive, you'll appreciate the inviting front porch, the perfect place to relax, enjoy conversations with friends, and greet neighbors passing by.Inside, the home features recently painted interiors and new laminate flooring in the bedrooms, creating a fresh and

  Joseph Firmin LPT REALTY, LLC

  2512 Eastbrook Blvd, Winter Park, FL 32792
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  /36

  $514,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft

  1438 Tierra Cir, Winter Park, FL 32792

  Charming, Fully Renovated Pool Home in Sought-After Winter Park. Welcome to this beautifully updated pool home, ideally located in desirable Winter Park—just minutes from premier shopping, dining, and entertainment, with easy access to major roadways for a seamless commute.From the moment you step inside, you’re greeted by a warm, modern aesthetic that blends comfort with style. To the right,

  Tony Nicolas COLDWELL BANKER REALTY

  1438 Tierra Cir, Winter Park, FL 32792
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  /7

  $510,000

  • 3 Beds
  • 2.5 Baths
  • 1,669 Sq Ft

  1061 Aragon Ave, Winter Park, FL 32789

  Excellent Winter Park location! This 3 bedroom 2.5 bath quad-condo LIVES LIKE A PRIVATE 2-STORY HOME, with attached oversized 2 car garage, private patio and back fenced area. (The unit is attached to another only by a common garage wall.) Priced below market value to be sold AS-IS for the seller's convenience and TLC needed. ** One Year AHS Home Warranty included.** Nestled between Denning Dr

  Lois Cox WATSON REALTY CORP

  1061 Aragon Ave, Winter Park, FL 32789
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  /29

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,238 Sq Ft

  1886 Clematis Ln, Winter Park, FL 32792

  Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property features 3 bedrooms and 2 bathrooms, offering a perfect blend of modern style and cozy charm. Step inside to experience the allure of an open floor plan that seamlessly connects the living spaces. The kitchen, fully renovated and

  Steven Greening EXP REALTY LLC

  1886 Clematis Ln, 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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  /5

  $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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  /26

  $449,900

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  259 Orange Terrace Dr, Winter Park, FL 32789

  WOW! NEW PRICE! $10,000 SAVINGS!! RENOVATED AND MOVE IN READY! Make this beautiful three-bedroom, two-bath home in desirable Winter Park 32789 your next place to call home! Extensively updated throughout, this home offers the perfect blend of modern style, comfort and convenience. Filled with natural light, this home features a beautifully renovated kitchen with an open pass-through breakfast bar

  Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  259 Orange Terrace Dr, Winter Park, FL 32789
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  /57

  $399,990

  $5K PRICE DROP

  • 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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  /2

  $425,000

  • Land
  • 8,276 Sq Ft
  • $2,236,842 per Acre

  1909 Taylor Ave, Winter Park, FL 32792

  A great opportunity to own land in one of Winter Park's most sought-after pockets. This property's true value lies in its prime homesite. You can build your dream home or renovate to suit, all while capturing the location that can't be replicated. Tucked in an established, tree-lined neighborhood minutes from Park Avenue's boutiques and dining, Winter Park's chain of lakes, and easy access to

  Liz Jones ORANGE SLICE PROPERTIES

  1909 Taylor Ave, Winter Park, FL 32792
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  /38

  $575,000

  • 4 Beds
  • 2 Baths
  • 2,126 Sq Ft

  2641 Carvell Ct, Winter Park, FL 32792

  Modern Ranch Gem on a Corner Lot | 4 Bed | 2 Bath | 2,126 Sq Ft | Screened Pool | No HOA | Winter Park, FLWelcome to this beautiful 4-bedroom, 2-bathroom ranch-style home in Winter Park Estates! Situated on a desirable corner lot with no HOA, this spacious 2,126-square-foot home offers flexibility, comfort, and plenty of room to enjoy Florida living.The inviting floor plan

  Christina Perez CHAMBERLAIN REALTY LLC

  2641 Carvell Ct, Winter Park, FL 32792
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  /35

  $479,900

  • 3 Beds
  • 2 Baths
  • 1,561 Sq Ft

  5334 Lanyard Ct, Winter Park, FL 32792

  Welcome to this incredible 3-bedroom, 2-bath home offering thoughtful updates, modern finishes, and an outdoor escape designed for relaxed Florida living. Situated on an oversized lot, this property features a stunning backyard retreat complete with a newly resurfaced PebbleTec pool, water features, gazebo, paver patio, and saltwater system.Inside, enjoy luxury vinyl flooring throughout, new

  Shirley Welch BHHS FLORIDA REALTY

  5334 Lanyard Ct, Winter Park, FL 32792
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  /20

  $365,000

  • 3 Beds
  • 2.5 Baths
  • 1,861 Sq Ft

  7506 Cranes Creek Ct Unit 30, Winter Park, FL 32792

  Beautiful, move in ready townhouse located in the highly desirable area of Winter Park. This well-maintained home provides confort, convenience and a versatile layout perfect for modern living. Featuring a spacious 2 car garage and a flexible 4th room on the first floor, ideal for a home an office, guest bedroom or additional living space. Enjoy being just minutes from shopping, dining and

  Sylvia Marchese TRANSCONTINENTAL REALTY GROUP,

  7506 Cranes Creek Ct Unit 30, Winter Park, FL 32792
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  /34

  $549,000

  $66K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft

  4392 Wardell Place Unit 201, Orlando, FL 32814

  SIGNIFICANT PRICE IMPORVEMENT!! This exquisite second-floor condo is a rare corner unit beautifully nestled in the heart of Baldwin Park. Boasting 1,434 square feet of living space, the home features a spacious open floor plan with impressive high ceilings and stunning natural light and a wrap-around porch. Brand new luxury vinyl floors run throughout the entire home, which includes three

  Brian Cirillo BALDWIN PARK REALTY LLC

  4392 Wardell Place Unit 201, Orlando, FL 32814
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  /25

  $395,000

  • 2 Beds
  • 1 Bath
  • 945 Sq Ft

  1812 Janice Ave, Orlando, FL 32803

  This adorable property is located on a quiet dead end street just a block off the Corrine retail and restaurant area. It offers solid concrete block construction, an expanded driveway, beautiful hardwood floors in very good condition, stainless steel appliances in the kitchen, a beautifully renovated bathroom, a fully functional garage and a wonderful living space in the fenced backyard. With its

  Kris Santullo FLORIDA HOME TEAM REALTY LLC

  1812 Janice Ave, Orlando, FL 32803
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  /20

  $340,000

  $10K PRICE DROP

  • 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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  /31

  $449,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft

  3365 Pelham Rd, Orlando, FL 32803

  Nestled in the highly sought-after Orwin Manor neighborhood, this charming 3-bedroom, 2-bath home offers the perfect blend of character, comfort, and opportunity. Whether you're searching for a move-in ready home, an investment property, or the ideal location to build your custom dream home, this property delivers exceptional flexibility in one of Orlando's most desirable

  Tiffany Yates COMPASS FLORIDA LLC

  3365 Pelham Rd, Orlando, FL 32803

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