28,400

Winter Park, FL Homes

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  • /24

    $425,000

    Pending
    • 4 Beds
    • 2 Baths
    • 1,610 Sq Ft

    814 Densmore Dr, Winter Park, FL 32792

    Under contract-accepting backup offers. Welcome to this charming home situated on a spacious lot in a quiet, established neighborhood in Winter Park. From the moment you arrive, you’ll appreciate the inviting curb appeal, expansive front yard, and peaceful setting that make this property feel like home.Inside, the home offers a light and open layout with a seamless flow between the living,

    Liz Jones ORANGE SLICE PROPERTIES

    814 Densmore Dr, Winter Park, FL 32792
  • /13

    $2,295 Per Month

    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft
    • Townhouse for Rent

    3486 Bougainvillea Dr Unit A, Winter Park, FL 32792

    Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

    Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

    3486 Bougainvillea Dr Unit A, Winter Park, FL 32792
  • /2

    $879,000

    Sold Nov 14, 2025

    451 Fairfax Ave, Winter Park, FL 32789

    • 3 Beds
    • 3 Baths
    • 2,227 Sq Ft
    • Built 2003

    Last Sold Summary

    • 2% Below List Price
    • $395/SF
    • 5 Days On Market

    Current Estimated Value $886,383

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

    451 Fairfax Ave, Winter Park, FL 32789
    • /16

      Est $1,013,361

      Not Listed For Sale

      2400 Roxbury Rd, Winter Park, FL 32789

      • 4 Beds
      • 3.5 Baths
      • 3,110 Sq Ft
      • Built 2023
      2400 Roxbury Rd, Winter Park, FL 32789

      Last Sold Summary

      • 55 Days On Market

  • /29

    $515,000

    $65K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,818 Sq Ft

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789

    Virtually Staged. **Price Improvement** Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events. Situated in the heart of Winter Park, this residence offers the perfect blend of lifestyle,

    Courtney Dietch ALL REAL ESTATE & INVESTMENTS

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789
  • /25

    $2,600 Per Month

    • 3 Beds
    • 2 Baths
    • 1,669 Sq Ft
    • House for Rent

    4959 Tangerine Ave, Winter Park, FL 32792

    Enter this home into the large spacious living room with plenty of natural light. The modern kitchen offers brand new stainless steel appliances. Plenty of open space with great lighting, beautiful cabinets and wood counters and island. The light comes through the sliding glass windows which leads onto the back patio with a huge, fenced backyard, great for entertaining a large family or friends.

    4959 Tangerine Ave, Winter Park, FL 32792
  • /2

    $965,000

    Sold Mar 12, 2026

    1444 Pelican Bay Trail, Winter Park, FL 32792

    • 4 Beds
    • 2.5 Baths
    • 3,121 Sq Ft
    • Built 1984

    Last Sold Summary

    • 12% Below List Price
    • $309/SF
    • 314 Days On Market

    Current Estimated Value $944,125

    Last Listing Agent Jacob Hara TRANSCEND REALTY

    1444 Pelican Bay Trail, Winter Park, FL 32792
    • /19

      Est $2,500,402

      Not Listed For Sale

      350 Beloit Ave, Winter Park, FL 32789

      • 3 Beds
      • 3.5 Baths
      • 3,205 Sq Ft
      • Built 2018
      350 Beloit Ave, Winter Park, FL 32789

      Last Sold Summary

      • 0 Days On Market

  • /26

    $499,000

    $51K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,433 Sq Ft

    2974 Chantilly Ave, Winter Park, FL 32789

    Virtually Staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the

    Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

    2974 Chantilly Ave, Winter Park, FL 32789
  • /25

    $5,490 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,354 Sq Ft
    • Condo for Rent

    782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

    Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the

    Steven Koleno BEYCOME OF FLORIDA LLC

    782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
  • /2

    $382,000

    Sold Jul 02, 2025

    1909 Edwin Blvd, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,355 Sq Ft
    • Built 1955

    Last Sold Summary

    • 7% Below List Price
    • $282/SF
    • 34 Days On Market

    Current Estimated Value $431,586

    Last Listing Agent Brian Craib OLDE TOWN BROKERS INC

    1909 Edwin Blvd, Winter Park, FL 32792
    • /35

      Est $293,674

      Not Listed For Sale

      228 Balfour Dr Unit 17, Winter Park, FL 32792

      • 2 Beds
      • 2 Baths
      • 1,287 Sq Ft
      • Built 1985
      228 Balfour Dr Unit 17, Winter Park, FL 32792

      Last Sold Summary

      • 213 Days On Market

  • /50

    $1,425,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,170 Sq Ft

    1751 Goodrich Ave, Winter Park, FL 32789

    Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

    Stephanie Baldner EXP REALTY LLC

    1751 Goodrich Ave, Winter Park, FL 32789
  • /37

    $6,500 Per Month

    • 6 Beds
    • 5 Baths
    • 3,676 Sq Ft
    • Condo for Rent

    4571 Kawilla Crest Place, Winter Park, FL 32792

    Characterized by its expansive layout and modern charm, 4571 Kawilla Crest Place in Winter Park, FL, offers an extraordinary living experience with six spacious bedrooms and five full bathrooms. Boasting a generous 3,676 square feet, this property is perfect for those who appreciate space and comfort. The open-concept design fosters a seamless flow between living areas, creating an inviting

    4571 Kawilla Crest Place, Winter Park, FL 32792
  • /2

    $89,750

    Sold Dec 05, 2025

    3002 George Mason Ave Unit 3, Winter Park, FL 32792

    • 2 Beds
    • 2.5 Baths
    • 1,085 Sq Ft
    • Built 1974

    Last Sold Summary

    • 25% Below List Price
    • $83/SF
    • 92 Days On Market

    Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

    3002 George Mason Ave Unit 3, Winter Park, FL 32792
    • /80

      Est $1,157,853

      Not Listed For Sale

      1999 Soaring Oak Way, Winter Park, FL 32792

      • 5 Beds
      • 4.5 Baths
      • 4,307 Sq Ft
      • Built 2019
      1999 Soaring Oak Way, Winter Park, FL 32792

      Last Sold Summary

      • 5 Days On Market

  • /19

    $510,000

    $89K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,805 Sq Ft

    2627 Ambergate Rd, Winter Park, FL 32792

    Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in!Investors -- You will love the cash flow upside with this property.Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more.You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for

    Ryan Minadie COLDWELL BANKER REALTY

    2627 Ambergate Rd, Winter Park, FL 32792
  • /20

    $1,600 Per Month

    • 2 Beds
    • 1.5 Baths
    • 825 Sq Ft
    • Townhouse for Rent

    2523 Alexa Ct, Winter Park, FL 32792

    Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

    Joseph La Rosa LA ROSA REALTY LLC

    2523 Alexa Ct, Winter Park, FL 32792
  • /2

    $2,185,000

    Sold May 21, 2026

    2722 Eastern Pkwy, Winter Park, FL 32789

    • 5 Beds
    • 4.5 Baths
    • 3,334 Sq Ft
    • Built 2026

    Last Sold Summary

    • 5% Below List Price
    • $655/SF
    • 105 Days On Market

    Current Estimated Value $1,678,189

    Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

    2722 Eastern Pkwy, Winter Park, FL 32789
    • /11

      Est $442,519

      Not Listed For Sale

      2770 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2024
      2770 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

      • 99 Days On Market

  • /2

    $3,100,000

    New Construction Pending
    • 5 Beds
    • 4.5 Baths
    • 3,460 Sq Ft

    1351 Magnolia Ave, Winter Park, FL 32789

    Under Construction. Just completed and ready to impress, this stunning custom-built residence delivers elevated design and effortless luxury in one of Winter Park’s most sought-after locations. Featuring 5 bedrooms and 4.5 bathrooms, this home blends timeless architecture with a fresh, curated aesthetic.From the moment you step inside, you’re greeted by warm wood flooring, custom millwork,

    Nickolas McKee KELLER WILLIAMS WINTER PARK

    1351 Magnolia Ave, Winter Park, FL 32789
  • /18

    $1,800 Per Month

    • 3 Beds
    • 2 Baths
    • 1,266 Sq Ft
    • Condo for Rent

    3050 Autumn Ct, Winter Park, FL 32792

    Don’t miss this charming 3/2 home in Winter Park now available! Step inside to find tile and laminate flooring throughout, creating easy maintenance and a modern feel. Enjoy the added convenience of an in-unit washer and dryer and relax outdoors on your covered back patio, complete with an additional storage closet.Situated on a spacious corner lot, this home provides extra privacy

    3050 Autumn Ct, Winter Park, FL 32792
  • /2

    $495,000

    Sold Feb 17, 2026

    422 S Ranger Blvd, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • Built 1965

    Last Sold Summary

    • 7% Below List Price
    • $295/SF
    • 77 Days On Market

    Current Estimated Value $505,614

    Last Listing Agent David Perez COLDWELL BANKER REALTY

    422 S Ranger Blvd, Winter Park, FL 32792
    • /46

      Est $952,014

      Not Listed For Sale

      1913 S Lakemont Ave, Winter Park, FL 32792

      • 3 Beds
      • 3.5 Baths
      • 2,085 Sq Ft
      • Built 2023
      1913 S Lakemont Ave, Winter Park, FL 32792

      Last Sold Summary

      • 119 Days On Market

  • /25

    $1,249,900

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 2,936 Sq Ft

    Winter Park, FL 32789

    Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to

    Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

    Winter Park, FL 32789
  • /46

    $2,875 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft
    • Townhouse for Rent

    1351 Merrydale Way, Winter Park, FL 32792

    Fantastic, Modern townhome WITH 3 beds & 2.5 baths. Hawk's Crest is a gated community in Winter Park. This home is has a very spacious open floor plan with a water view! The kitchen has granite countertops and is fully equipped with stainless steel Whirlpool appliances; oven, stove, microwave, refrigerator, dishwasher, and garbage disposal. The kitchen area also has a large pantry! This energy

    Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

    1351 Merrydale Way, Winter Park, FL 32792
  • /2

    $755,000

    Sold Jul 18, 2025

    1000 Howell Branch Rd, Winter Park, FL 32789

    • Land
    • 23,958 Sq Ft
    • $1,372,727 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 241 Days On Market

    Current Estimated Value $835,809

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1000 Howell Branch Rd, Winter Park, FL 32789
    • /11

      Not Listed For Sale

      0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

      0 Dodd Rd Unit MFRO6144077, Winter Park, FL 32792

      Last Sold Summary

      • 8 Days On Market

  • /47

    $5,995,000

    $455K PRICE DROP
    • 5 Beds
    • 5.5 Baths
    • 5,476 Sq Ft

    1200 Via Salerno, Winter Park, FL 32789

    Along one of the cobblestone brick streets in the prestigious Via’s of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke finishes throughout. A circular driveway and manicured grounds designed by Signature Landscapes create a graceful approach. Inside, a dramatic curved staircase crowned by a breathtaking 1960s vintage

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1200 Via Salerno, Winter Park, FL 32789
  • /9

    $1,450 Per Month

    • 2 Beds
    • 2 Baths
    • 840 Sq Ft
    • Newly remodeled 2/2 condo Winter Park $300. incentive for move in by 6/15/2026

    3651 N Goldenrod Rd Unit A104, Winter Park, FL 32792

    This 2 bedroom two bath condo has been remodeled with new tile flooring, new bathrooms and all new appliances including Washer and dryer as well as kitchen appliances, stove, fridge, dishwasher, and microwave. Community has a large community pool right outside your door. Great location with access to major roads, great dining venues and shopping possibilities. Ready for move in now. Come

    3651 N Goldenrod Rd Unit A104, Winter Park, FL 32792
  • /2

    $130,000

    Sold Nov 25, 2025

    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft
    • Built 1970

    Last Sold Summary

    • 13% Below List Price
    • $179/SF
    • 35 Days On Market

    Current Estimated Value $133,898

    Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
    • /2

      Est $5,549,607

      Not Listed For Sale

      654 W Morse Blvd, Winter Park, FL 32789

      • 5 Beds
      • 7.5 Baths
      • 8,752 Sq Ft
      • Built 2022
      654 W Morse Blvd, Winter Park, FL 32789

      Last Sold Summary

      • 120 Days On Market

  • /9

    $165,000

    $30K PRICE DROP Pending
    • 2 Beds
    • 2.5 Baths
    • 1,031 Sq Ft

    7444 Woodburn Ct Unit 29, Winter Park, FL 32792

    Under contract-accepting backup offers. Sought after Winter Park Location! 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community. 1,031 sq. ft. newer roof installed in 2023. The exterior is thoughtfully landscaped, enhancing the home’s inviting curb appeal. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes to Orlando International Airport, 10 minutes to

    Abranette Lopez LPT REALTY, LLC

    7444 Woodburn Ct Unit 29, Winter Park, FL 32792
  • /24

    $2,450 Per Month

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • House for Rent

    3121 Heartwood Ave, Winter Park, FL 32792

    Discover this beautifully updated 3-bedroom, 2-bathroom home located in a highly sought-after neighborhood in Winter Park, served by A-rated schools. This property features stunning ceramic tile flooring throughout, a modern kitchen equipped with stainless steel appliances and elegant quartz countertops, and luxurious upgraded bathrooms that offer both style and comfort. Relax on the inviting

    Haimdatt Sadoo DELUXE REALTY OF CENTRAL FLORIDA

    3121 Heartwood Ave, Winter Park, FL 32792
  • /2

    $975,000

    Sold Feb 10, 2026

    1150 Kenwood Ave, Winter Park, FL 32789

    • 3 Beds
    • 2.5 Baths
    • 2,557 Sq Ft
    • Built 1988

    Last Sold Summary

    • 24% Below List Price
    • $381/SF
    • 97 Days On Market

    Current Estimated Value $1,023,083

    Last Listing Agent JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

    1150 Kenwood Ave, Winter Park, FL 32789
    • /21

      Est $429,189

      Not Listed For Sale

      2861 Clever Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,907 Sq Ft
      • Built 2023
      2861 Clever Ln, Winter Park, FL 32792

      Last Sold Summary

      • 1 Day On Market

  • /11

    $198,000

    $2K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,062 Sq Ft

    3060 George Mason Ave Unit 12, Winter Park, FL 32792

    Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

    Adriana Sanchez AROD PARTNERS REALTY

    3060 George Mason Ave Unit 12, Winter Park, FL 32792
  • /6

    $1,295 Per Month

    • 1 Bed
    • 1 Bath
    • 809 Sq Ft
    • Large One Bedroom One Bath First level Condo Flexible qualifications.

    7425 Daniel Webster Dr, Winter Park, FL 32792

    Discover this large first-level one-bedroom, one-bath condo in Winter Park. The unit features new cabinets and appliances, a remodeled bathroom, and new laminated flooring throughout. Enjoy a spacious bedroom with a bay window that brings in natural light, plus a covered tiled patio for outdoor seating. Washer and Dryer inside for convenience. The community offers a pool for residents.

    7425 Daniel Webster Dr, Winter Park, FL 32792
  • /2

    $415,000

    Sold Mar 04, 2026

    1816 Ivy Ln, Winter Park, FL 32792

    • 4 Beds
    • 2 Baths
    • 1,725 Sq Ft
    • Built 1959

    Last Sold Summary

    • 8% Below List Price
    • $241/SF
    • 139 Days On Market

    Current Estimated Value $406,197

    Last Listing Agent Michael Cameron CAMERON REALTY GROUP LLC

    1816 Ivy Ln, Winter Park, FL 32792
    • /23

      Est $313,641

      Not Listed For Sale

      3197 Crown Jewel Ct, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,408 Sq Ft
      • Built 2019
      3197 Crown Jewel Ct, Winter Park, FL 32792

      Last Sold Summary

      • 23 Days On Market

Showing Results 601 - 640, Page 16 of 18

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