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

• 

  

  

  /42

  $279,900

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

  2305 Sun Valley Cir, Winter Park, FL 32792

  Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas.

  Ryan Barnett MARKET CONNECT REALTY LLC

  2305 Sun Valley Cir, Winter Park, FL 32792
• 

  

  

  /8

  $354,999

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  310 Granada Dr, Winter Park, FL 32789

  Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living space on a 6,460-square-foot lot, this single-story residence features a functional floor plan with tile flooring throughout the main living and dining areas. A covered rear entry leads to a brick paver patio and a fully fenced

  William Ward A-WARD WINNING REALTY LLC

  310 Granada Dr, Winter Park, FL 32789
• 

  

  

  /13

  $270,000

  $30K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,803 Sq Ft

  2487 Harbour Way, Winter Park, FL 32792

  Welcome to 2487 Harbour Way, a spacious single-story townhome offering 3 bedrooms, 3 full bathrooms, and 1,803 square feet of comfortable living space. The practical layout features inviting living and dining areas, a well-equipped kitchen, central air, and a walk-in closet. Outside, garden space, lighting, and sidewalks add to the home's appeal. Enjoy a low-maintenance lifestyle in Windward

  Joel Garay LOKATION

  2487 Harbour Way, Winter Park, FL 32792
• 

  

  

  /38

  $368,000

  $7K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,240 Sq Ft

  885 Carnation Dr, Winter Park, FL 32792

  Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully renovated kitchen with a stunning waterfall quartz island, and two beautifully remodeled bathrooms. The garage has been updated with new flooring and a new garage door.Major improvements include a new roof (2024), new A/C

  Tashania Brown RADIUS REALTY GROUP LLC

  885 Carnation Dr, Winter Park, FL 32792
• 

  

  

  /30

  $439,900

  $30K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,508 Sq Ft

  2041 Jewell Ave, Winter Park, FL 32789

  Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful home! First time on the market in over 60 years! Filled with decades of cherished family memories, this beloved home is ready for its next chapter. Located in the highly desirable Winter Park 32789 ZIP code, 2041 Jewell Avenue offers an unbeatable location just minutes from

  Martha Coronel IAD REAL ESTATE

  2041 Jewell Ave, Winter Park, FL 32789
• 

  

  /7

  $459,900

  $39K PRICE DROP

  • Land
  • 9,147 Sq Ft
  • $2,190,000 per Acre

  3601 Midiron Dr, Winter Park, FL 32789

  Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a

  Juliana Usquiano EMPIRE NETWORK REALTY

  3601 Midiron Dr, Winter Park, FL 32789
• 

  

  /27

  $399,900

  $55K PRICE DROP

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

  1849 Viburnum Ln, Winter Park, FL 32792

  This beautifully renovated Winter Park home feels warm, inviting, and easy to love. Bright natural light highlights a brand-new kitchen with modern appliances, a waterfall countertop, and soft wood finishes. Both bathrooms have been transformed with elegant marble look tile and spa style showers. You’ll fall in love with the large private backyard, perfect for summer barbecues, outdoor

  Lesly Hijar REAL BROKER, LLC

  1849 Viburnum Ln, Winter Park, FL 32792
• 

  

  /41

  $285,000

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft

  283 Sandlewood Trail Unit 3, Winter Park, FL 32789

  Virtually Staged. MOVE IN READY in Winter Park with nearly $30,000 in recent upgrades and improvements! This beautifully updated 2 bedroom, 2.5 bathroom condo in Sandlewood Creek offers a bright, open layout, conservation views and a quiet community setting in an incredibly convenient location.The main level features a spacious open living and dining area with plenty of room to create

  Crystal Adams RE/MAX INNOVATION

  283 Sandlewood Trail Unit 3, Winter Park, FL 32789
• 

  

  /36

  $429,900

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  1486 Hyde Park Dr, Winter Park, FL 32792

  Welcome to this inviting 3-bedroom, 2-bath pool home in Winter Park’s desirable Hyde Park community! Featuring a 2021 roof, tile flooring throughout, and a spacious kitchen with abundant storage and white granite countertops, this home offers bright, open living spaces enhanced by skylights that bring in beautiful natural light. Step outside to enjoy the screened pool and spa and fenced backyard,

  1486 Hyde Park Dr, Winter Park, FL 32792
• 

  

  /23

  $399,000

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,122 Sq Ft

  1092 Eastbrook Blvd, Winter Park, FL 32792

  Remodeled pool home located in the highly sought after desirable Winter Park school district. This property has a.27 acre corner lot with room to expand and a pool/spa perfect for relaxing or entertaining guest.Inside the living room features vaulted ceilings that create a bright open feeling and a huge screened in patio for outdoor entertaining. The bathrooms have been beautifully remodeled,

  Eva Firios JC FLORIDA REALTY LLC

  1092 Eastbrook Blvd, Winter Park, FL 32792
• 

  

  /25

  $285,000

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft

  2657 Exuma Way, Winter Park, FL 32792

  Freshly remodeled and move-in ready, this 3-bedroom, 2-bath townhome offers comfortable living in a highly desirable Winter Park location. The open-concept living and dining areas create a welcoming space for everyday living and entertaining, while the convenient pass-through window connects the kitchen and dining room for added functionality. The brand-new kitchen remodel features granite

  Jerry Agan HAVEN PROPERTY GROUP LLC

  2657 Exuma Way, Winter Park, FL 32792
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /30

  $269,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  5108 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to 5108 Lazy Oaks Drive, a 2-bedroom, 2-bathroom condo in a desirable Winter Park location. This light-filled home has approximately 1,008 square feet of comfortable living space with a functional floor plan, abundant windows, skylight and sliding glass doors that bring in plenty of natural light.The spacious living room features a beautiful brick fireplace and sliding glass door

  Steven Koleno BEYCOME OF FLORIDA LLC

  5108 Lazy Oaks Dr, Winter Park, FL 32792
• 

  /2

  $205,000

  $5K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit C202, Winter Park, FL 32789

  This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This

  Hoover Yap PRIMESTATE REALTY, INC.

  1695 Lee Rd Unit C202, Winter Park, FL 32789
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /20

  $267,000

  $12K PRICE DROP

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

  2317 Sun Valley Cir, Winter Park, FL 32792

  Seller financing at 4.9% APR is available for qualified buyers—an opportunity to start building equity from day one. Discover comfort and convenience in this charming, spacious 2-bedroom, 2-bath residence in the heart of Winter Park. The inviting living room features vaulted ceilings, while the fully equipped open-concept kitchen offers abundant cabinet space for everyday living and entertaining.

  Robert Arnold SAND DOLLAR REALTY GROUP INC

  2317 Sun Valley Cir, Winter Park, FL 32792
• 

  

  /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
• 

  

  /25

  $269,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 242, Winter Park, FL 32789

  Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll

  Alex Scures COLONIALTOWN REALTY

  151 N Orlando Ave Unit 242, Winter Park, FL 32789
• 

  

  /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
• 

  /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
• 

  

  /22

  $235,000

  • 2 Beds
  • 1 Bath
  • 924 Sq Ft

  2712 Tortoise Cove, Winter Park, FL 32792

  Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with NO HOA. Located conveniently to all major roads, shopping, schools and restaurants. New roof installed 2025. Don't hesitate to come view!

  Lisa Wright CHARLES RUTENBERG REALTY ORLANDO

  2712 Tortoise Cove, Winter Park, FL 32792
• 

  

  /19

  $299,000

  Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,208 Sq Ft

  2168 Ridge Dr, Winter Park, FL 32792

  Virtually Staged. Prime Winter Park Opportunity – Original Terrazzo Floors, Solid Block Construction & Endless PotentialDiscover an exceptional opportunity to own a classic Winter Park home priced at just $299,000. Situated on a generous 0.20-acre lot, this 3-bedroom, 1-bath concrete block home offers 1,208 square feet of living space and the perfect foundation to create your dream home or

  Dragana Todorovic ENGEL & VOLKERS NEW SMYRNA

  2168 Ridge Dr, Winter Park, FL 32792
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /63

  $249,000

  $10K PRICE DROP

  • 2 Beds
  • 3 Baths
  • 1,328 Sq Ft

  1713 Gulfview Dr Unit 435B, Maitland, FL 32751

  Welcome home to this beautifully updated two-story condo nestled in one of Maitland's most established communities, where lush mature landscaping, winding sidewalks, a community pool, lake access and a private dock create a peaceful setting just minutes from some of Central Florida's favorite restaurants, shopping and entertainment. Enjoy easy access to Enzian Theater, Winter Park Village, Trader

  Becki Douglas MAINFRAME REAL ESTATE

  1713 Gulfview Dr Unit 435B, Maitland, FL 32751
• 

  

  /14

  $239,000

  • 2 Beds
  • 2 Baths
  • 1,087 Sq Ft

  1711 Grove St Unit 519, Maitland, FL 32751

  Virtually Staged. Rare updated 2/2 | | Top-Rated SchoolsWelcome to peaceful Park Lake Villas! This fully updated single-story condo has spacious living, major energy-efficient upgrades, and an unbeatable location zoned for Dommerich Elementary, Maitland Middle, and Edgewater High.Key Features Brand New A/C (2025) & Updated R-38 Insulation Low-E Thermal Pane Windows & Slider Door replaced

  Steven Koleno BEYCOME OF FLORIDA LLC

  1711 Grove St Unit 519, Maitland, FL 32751
• 

  

  /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
• 

  

  /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

Showing Results 81 - 114, Page 3 of 3