28,231

Winter Park, FL Homes

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  • /22

    $1,795,000

    New Construction Pending
    • 4 Beds
    • 4 Baths
    • 2,819 Sq Ft

    2501 Lafayette Ave, Winter Park, FL 32789

    Virtually Staged. A rare new construction offering in the heart of Winter Park — 2501 Lafayette Ave is a 2,810 sq ft architectural residence crafted by curated design firm - Catalyst Design, with 25-year experience and Parade of Homes judge across Naples, Daytona & Southwest Florida. 4 bed | 4 bath | office | 2-car garage | saltwater pool. Every detail built to a single standard: the highest one.

    Michael Elias CHARLES RUTENBERG REALTY ORLANDO

    2501 Lafayette Ave, Winter Park, FL 32789
  • /23

    $1,300 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,079 Sq Ft
    • Condo for Rent

    3004 George Mason Ave Unit K5d, Winter Park, FL 32792

    This beautiful 2-bedroom, 2.5-bathroom, 2-Story condo located in the highly desirable Colonies community of Winter Park, Florida, offers 1,079 square feet of thoughtfully designed living space while featuring modern updates throughout, including durable tile flooring in the main living areas, crisp white cabinetry, and sleek stainless-steel appliances. The layout transitions seamlessly into a

    3004 George Mason Ave Unit K5d, Winter Park, FL 32792
  • /2

    $286,000

    Sold May 22, 2026

    3204 Netherwood Dr, Winter Park, FL 32792

    • 2 Beds
    • 1.5 Baths
    • 1,056 Sq Ft
    • Built 1983

    Last Sold Summary

    • 12% Below List Price
    • $271/SF
    • 66 Days On Market

    Current Estimated Value $287,520

    Last Listing Agent Renee Anthony WATSON REALTY CORP.

    3204 Netherwood Dr, Winter Park, FL 32792
    • /2

      Not Listed For Sale

      3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

      • 2 Beds
      • 2.5 Baths
      • 1,079 Sq Ft
      • Built 1974
      3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

      Last Sold Summary

      • 66 Days On Market

      Last Listing Agent Ali Khaku, MBA DALTON WADE INC

  • /41

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft

    5331 Oak Ct, Winter Park, FL 32792

    Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

    Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

    5331 Oak Ct, Winter Park, FL 32792
  • /17

    $2,499 Per Month

    • 4 Beds
    • 2 Baths
    • 1,625 Sq Ft
    • House for Rent

    1016 Manchester Cir, Winter Park, FL 32792

    SPECIAL!! $300 OFF THE 1ST MO RENT=- TERMS APPLY*LAWNCARE INCLUDED IN RENT!!Discover this versatile home featuring an open-concept layout that includes a spacious living room, a cozy family room, and a dedicated dining areaperfect for relaxing, entertaining, or working remotely. The main living spaces are adorned with stylish tile flooring, while all bedrooms showcase upgraded luxury

    Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

    1016 Manchester Cir, Winter Park, FL 32792
  • /2

    $385,000

    Sold Nov 12, 2025

    4421 Steed Terrace, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 1,788 Sq Ft
    • Built 1989

    Last Sold Summary

    • 14% Below List Price
    • $215/SF
    • 209 Days On Market

    Current Estimated Value $412,441

    Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

    4421 Steed Terrace, Winter Park, FL 32792
    • /2

      Est $447,796

      Not Listed For Sale

      Unlisted Address

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      Unlisted Address

      Last Sold Summary

      Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  • /33

    $1,350,000

    • 4 Beds
    • 4 Baths
    • 2,998 Sq Ft

    1320 Orchid Ave, Winter Park, FL 32789

    Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Orlando. Offering nearly 3,000 square feet of thoughtfully designed living space, this 4-bedroom, 4-bath home combines contemporary architecture, abundant natural light, and elevated finishes in one of Central Florida’s most

    Isis Sarcos EXP REALTY LLC

    1320 Orchid Ave, Winter Park, FL 32789
  • /22

    $3,095 Per Month

    • 3 Beds
    • 2 Baths
    • House for Rent

    2545 Madeline Ave, Winter Park, FL 32789

    Welcome to this beautifully updated 3-bedroom, 2-bathroom home, thoughtfully designed with modern finishes, abundant natural light, and comfortable spaces for everyday living and entertaining.The entire home features luxury vinyl flooring, creating a stylish and cohesive look throughout. The recently updated kitchen is truly the heart of the home, showcasing crisp white cabinetry, elegant

    2545 Madeline Ave, Winter Park, FL 32789
  • /2

    $2,835,000

    Sold Nov 24, 2025

    255 Stirling Ave, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 3,635 Sq Ft
    • Built 1982

    Last Sold Summary

    • 14% Below List Price
    • $780/SF
    • 25 Days On Market

    Current Estimated Value $2,904,020

    Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    255 Stirling Ave, Winter Park, FL 32789
    • /2

      Est $436,899

      Not Listed For Sale

      2838 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2838 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 8 Days On Market

      Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

  • /9

    $349,000

    • 2 Beds
    • 1 Bath
    • 749 Sq Ft

    811 Overspin Dr, Winter Park, FL 32789

    Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those

    Rickey Singh RICK SINGH REAL ESTATE

    811 Overspin Dr, Winter Park, FL 32789
  • /16

    $1,550 Per Month

    • 2 Beds
    • 2 Baths
    • 964 Sq Ft
    • Townhouse for Rent

    3254 Howell Branch Rd, Winter Park, FL 32792

    SEPTEMBER MOVE-IN SPECIAL — GET A $500 MOVE-IN CREDIT!This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living.Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring

    Carissa Lawhun FLORIDA REALTY INVESTMENTS

    3254 Howell Branch Rd, Winter Park, FL 32792
  • /2

    $627,000

    Sold Mar 23, 2026

    428 Selkirk Dr, Winter Park, FL 32792

    • 4 Beds
    • 3 Baths
    • 1,782 Sq Ft
    • Built 1957

    Last Sold Summary

    • 5% Below List Price
    • $352/SF
    • 103 Days On Market

    Current Estimated Value $633,842

    Last Listing Agent Sheri Malin REDFIN CORPORATION

    428 Selkirk Dr, Winter Park, FL 32792
    • /35

      Est $207,656

      Not Listed For Sale

      656 Saint Johns Ct Unit S, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,037 Sq Ft
      • Built 1981
      656 Saint Johns Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Marina Gamundi KELLER WILLIAMS ADVANTAGE III

  • /10

    $5,500,000

    New Construction
    • 4 Beds
    • 4.5 Baths
    • 4,775 Sq Ft

    313 Sylvan Dr, Winter Park, FL 32789

    Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    313 Sylvan Dr, Winter Park, FL 32789
  • /10

    $1,595 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft
    • Condo for Rent

    3225 Oak Lawn Place, Winter Park, FL 32792

    Discover your new home in this cozy 2-bedroom, 2.5-bathroom townhome! No one above or below you! Featuring an open-concept living area, updated kitchen, and private outdoor space, this inviting retreat is perfect for relaxation and entertaining. Conveniently located near shopping, dining, and parks, it offers the ideal blend of comfort and convenience. Don't miss out on this gem! Each bedroom has

    3225 Oak Lawn Place, Winter Park, FL 32792
  • /2

    $90,000

    Sold Sep 02, 2026

    145 Scottsdale Square Unit 145, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,020 Sq Ft
    • Built 1974

    Last Sold Summary

    • 10% Below List Price
    • $88/SF
    • 13 Days On Market

    Current Estimated Value $99,739

    Last Listing Agent Shaunda Hall GENSTONE REALTY

    145 Scottsdale Square Unit 145, Winter Park, FL 32792
    • /2

      Est $360,253

      Not Listed For Sale

      230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

      • 2 Beds
      • 2.5 Baths
      • 1,536 Sq Ft
      • Built 1986
      230 Killarney Bay Ct Unit 3, Winter Park, FL 32789

      Last Sold Summary

      • 53 Days On Market

      Last Listing Agent Carol van den Berg VAN DEN BERG REAL ESTATE GROUP

  • /55

    $745,000

    $30K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,020 Sq Ft

    1287 Verdant Glade Place, Winter Park, FL 32792

    Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living |Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacious open floor plan with a private backyard setting and a layout that offers exceptional versatility. The main level includes the primary suite, dedicated study, laundry room, kitchen, and principal living areas, making

    Renee Funk EXP REALTY LLC

    1287 Verdant Glade Place, Winter Park, FL 32792
  • /2

    $4,250 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,000 Sq Ft
    • Townhouse for Rent

    544 N Knowles Ave Unit 540, Winter Park, FL 32789

    Luxury Living in Historic Winter Park. Amazing location in the heart of Winter Park and nestled within the historic Barbour House—a symbol of timeless elegance. This chic apartment offers a luxurious retreat just one block from the famed Park Avenue, where Winter Park's finest dining, shopping, and cultural experiences await. Step inside this meticulously designed space to discover a blend of

    Richard Traynor FLORIDA ONE REAL ESTATE LLC

    544 N Knowles Ave Unit 540, Winter Park, FL 32789
  • /2

    $625,000

    Sold Mar 27, 2026

    1500 Berkshire Ave, Winter Park, FL 32789

    • 3 Beds
    • 1.5 Baths
    • 1,485 Sq Ft
    • Built 1925

    Last Sold Summary

    • $421/SF
    • 51 Days On Market

    Current Estimated Value $619,071

    Last Listing Agent Lianna D'Angelo SOTERA LIVING

    1500 Berkshire Ave, Winter Park, FL 32789
    • /24

      Est $328,370

      Not Listed For Sale

      172 Balfour Dr Unit 2, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,426 Sq Ft
      • Built 1980
      172 Balfour Dr Unit 2, Winter Park, FL 32792

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  • /49

    $775,000

    • 4 Beds
    • 2.5 Baths
    • 1,899 Sq Ft

    1562 Arbor Park Dr, Winter Park, FL 32789

    Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central

    Abby Greenberg COMPASS FLORIDA LLC

    1562 Arbor Park Dr, Winter Park, FL 32789
  • /37

    $1,900 Per Month

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • House for Rent

    151 N Orlando Ave, Winter Park, FL 32789

    Discover this affordable and well-located 3-bedroom, 2-bathroom home in the desirable Winter Park area, perfect for those seeking comfort, convenience, and long-term stability.This property offers a functional layout with comfortable living spaces, ideal for families or individuals looking for a practical and welcoming place to call home.

    151 N Orlando Ave, Winter Park, FL 32789
  • /2

    $1,430,000

    Sold Nov 10, 2025

    1011 Mckean Cir, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,230 Sq Ft
    • Built 1955

    Last Sold Summary

    • $641/SF
    • 0 Days On Market

    Current Estimated Value $1,502,953

    Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

    1011 Mckean Cir, Winter Park, FL 32789
    • /18

      Est $438,250

      Not Listed For Sale

      2786 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2024
      2786 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /42

    $830,000

    $145K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,003 Sq Ft

    1507 Golfside Dr, Winter Park, FL 32792

    Virtually Staged. OUTSTANDING RENOVATION in a FANTASTIC LOCATION! Peace, Quiet & GOLF COURSE LIVING! This rare opportunity places you along the 13TH tee & offers tranquil backyard views of the 16TH fairway of the Winter Park Pines Golf Course (WP18)! Tree-lined street welcomes you to this completely renovated Floor to Ceiling ONE STORY beauty offers Serendipity LW Wood & porcelain tile flooring

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    1507 Golfside Dr, Winter Park, FL 32792
  • /10

    $2,000 Per Month

    • 3 Beds
    • 2 Baths
    • 1,072 Sq Ft
    • Townhouse for Rent

    2534 Leeward Way, Winter Park, FL 32792

    This beautiful 3-bedroom, 2-bathroom townhome offers a comfortable and inviting layout featuring laminate flooring, ceiling fans, abundant natural light, and all appliances included for your convenience.Ideally located in the desirable Winter Park area, this home provides easy access to top-rated schools, shopping centers, supermarkets, restaurants, and major roadways, making your daily

    Edgar Gurmeitte SERCONEP LLC

    2534 Leeward Way, Winter Park, FL 32792
  • /2

    $470,000

    Sold May 04, 2026

    1537 Bantam Way, Winter Park, FL 32792

    • 3 Beds
    • 2.5 Baths
    • 2,312 Sq Ft
    • Built 2022

    Last Sold Summary

    • 1% Below List Price
    • $203/SF
    • 3 Days On Market

    Current Estimated Value $515,696

    Last Listing Agent Jared Dunn LIVE MVRK LLC

    1537 Bantam Way, Winter Park, FL 32792
    • /29

      Not Listed For Sale

      7482 Canford Ct Unit 7482, Winter Park, FL 32792

      • 2 Beds
      • 1.5 Baths
      • 1,393 Sq Ft
      • Built 1974
      7482 Canford Ct Unit 7482, Winter Park, FL 32792

      Last Sold Summary

      • 9 Days On Market

      Last Listing Agent Dee Concepcion ALL REAL ESTATE & INVESTMENTS

  • /36

    $849,000

    • 3 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    437 N Capen Ave, Winter Park, FL 32789

    Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’

    Brandon Geers COMPASS FLORIDA LLC

    437 N Capen Ave, Winter Park, FL 32789
  • /14

    $1,640 Per Month

    • 2 Beds
    • 2 Baths
    • 1,038 Sq Ft
    • ADORABLE 2/2 CONDO WITH PRIVATE FENCED YARD — GREAT WINTER PARK LOCATION!

    3068 Autumn Ct, Winter Park, FL 32792

    Freshly painted and MOVE-IN READY! This charming 2-bedroom, 2-bath condo offers a private fenced yard, screened porch, and NO CARPET — perfect for pet owners or anyone who prefers easy-care flooring.? Highlights:•Contact us to schedule a showing.

    3068 Autumn Ct, Winter Park, FL 32792
  • /2

    $385,000

    Sold Feb 09, 2026

    5563 Garden Grove Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • Built 1988

    Last Sold Summary

    • 6% Below List Price
    • $268/SF
    • 36 Days On Market

    Current Estimated Value $394,749

    Last Listing Agent Anne Jones COLDWELL BANKER HUBBARD HANSEN

    5563 Garden Grove Cir, Winter Park, FL 32792
    • /11

      Est $437,055

      Not Listed For Sale

      2711 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2023
      2711 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  • /37

    $509,900

    $19K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 2,047 Sq Ft

    1660 Gladiolas Dr, Winter Park, FL 32792

    Updated Winter Park home with 2,047 sq ft of heated/cooled living space, a huge backyard, and NO HOA. This is an owner-updated home—not a flip—with quality improvements completed over the past several years and professionally completed permitted work.Major improvements include a 2021 roof, 2021 whole-house repipe, 2021 exterior stucco and paint, 2020 HVAC, 2023 kitchen remodel, 2023

    Stephen Hachey FLAT FEE MLS REALTY

    1660 Gladiolas Dr, Winter Park, FL 32792
  • /59

    $10,000 Per Month

    • 6 Beds
    • 4.5 Baths
    • 3,806 Sq Ft
    • House for Rent

    1620 Palm Ave, Winter Park, FL 32789

    Exceptional luxury rental opportunity in the heart of Winter Park! Located along a beautiful tree lined brick street, this custom built residence offers an impressive combination of sophisticated finishes, generous living spaces and resort style outdoor living. Featuring 6 bedrooms, 4.5 baths and a 3-car garage, the thoughtfully designed two-story floor plan provides exceptional flexibility for

    Rob Gaudreau MAINFRAME REAL ESTATE

    1620 Palm Ave, Winter Park, FL 32789
  • /2

    $786,000

    Sold Jun 09, 2026

    2940 de Brocy Way, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 2,679 Sq Ft
    • Built 1971

    Last Sold Summary

    • $293/SF
    • 5 Days On Market

    Current Estimated Value $775,525

    Last Listing Agent Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

    2940 de Brocy Way, Winter Park, FL 32792
    • /27

      Est $161,423

      Not Listed For Sale

      603 Saint Johns Ct Unit S, Winter Park, FL 32792

      • 1 Bed
      • 1 Bath
      • 759 Sq Ft
      • Built 1981
      603 Saint Johns Ct Unit S, Winter Park, FL 32792

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Melissa Johnson EXP REALTY LLC

Showing Results 601 - 640, Page 16 of 18

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