28,302

Winter Park, FL Homes

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  • /57

    $2,900,000 Pending

    • 3 Beds
    • 7 Baths
    • 5,483 Sq Ft

    1401 Green Cove Rd, Winter Park, FL 32789

    Under contract-accepting backup offers. Set across Lake Maitland on a street where every home is an architectural gem, this Award-winning Villa Toscana blends Old-World craftsmanship with timeless architectural elegance in one of Winter Park’s most coveted enclaves. Built in 2009 and named “Best of Show” in the Parade of Homes, this 5,483 sq ft estate offers 3 bedrooms, 7 bathrooms, and 7

    Adriana Oyarce ANCHOR REAL ESTATE

    1401 Green Cove Rd, Winter Park, FL 32789
  • /2

    $630,000 Sold Aug 11, 2025

    1792 Killarney Dr, Winter Park, FL 32789

    • 4 Beds
    • 3 Baths
    • 2,264 Sq Ft
    • Built 1958

    Last Sold Summary

    • 3% Below List Price
    • $278/SF
    • 1 Day On Market

    Current Estimated Value $652,518

    Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

    1792 Killarney Dr, Winter Park, FL 32789
    • /43

      Est $769,039 Not Listed For Sale

      7984 Pleasant Pine Cir, Winter Park, FL 32792

      • 5 Beds
      • 4 Baths
      • 3,496 Sq Ft
      • Built 2016
      7984 Pleasant Pine Cir, Winter Park, FL 32792

      Last Sold Summary

      • 3% Above List Price
      • $215/SF
      • 0 Days On Market

      Last Sold Price $750,000

      Last Listing Agent Kimberley Gernert BALDWIN PARK REALTY LLC

  • /60

    $2,295,000

    • 4 Beds
    • 3.5 Baths
    • 3,986 Sq Ft

    2299 Via Tuscany, Winter Park, FL 32789

    Welcome to 2299 Via Tuscany, a remarkable 4-bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40-acre private lot, offers a blend of luxury and comfort. The property has seen recent updates in the kitchen and bathrooms and features a new architectural shingle roof (2023), Pebble-tech style pool finish and a manicured landscape. Inside,

    Vincent Scarlatos CORCORAN PREMIER REALTY

    2299 Via Tuscany, Winter Park, FL 32789
  • /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 $949,558

    Last Listing Agent Jacob Hara TRANSCEND REALTY

    1444 Pelican Bay Trail, Winter Park, FL 32792
    • /40

      Est $814,506 Not Listed For Sale

      2035 Soaring Oak Way, Winter Park, FL 32792

      • 4 Beds
      • 3 Baths
      • 2,706 Sq Ft
      • Built 2021
      2035 Soaring Oak Way, Winter Park, FL 32792

      Last Sold Summary

      • 4% Above List Price
      • $290/SF
      • 130 Days On Market

      Last Sold Price $785,000

      Last Listing Agent Kimberly Slinger KELLY PRICE & COMPANY LLC

  • /30

    $139,000

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft

    151 Lewfield Cir Unit 4, Winter Park, FL 32792

    Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new

    Susan Tamlin KELLER WILLIAMS REALTY AT THE PARKS

    151 Lewfield Cir Unit 4, 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
    • /25

      Est $283,500 Not Listed For Sale

      5408 Peaco Place, Winter Park, FL 32792

      • 3 Beds
      • 1.5 Baths
      • 1,439 Sq Ft
      • Built 1984
      5408 Peaco Place, Winter Park, FL 32792

      Last Sold Summary

      • 23% Above List Price
      • $160/SF
      • 24 Days On Market

      Last Sold Price $230,000

      Last Listing Agent John Harbuck SERHANT

  • /5

    $4,595,000

    • Land
    • 0.35 Acre
    • $13,128,571 per Acre

    1336 College Point, Winter Park, FL 32789

    A rare offering on the shores of Lake Virginia, this prime lakefront parcel presents a distinguished opportunity within Winter Park’s most coveted waterfront corridor. Encompassing a significant Lake Virginia homesite on the Winter Park Chain of Lakes, the site currently includes a 1926 structure that may be preserved, redesigned or removed to accommodate a custom waterfront residence. Positioned

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1336 College Point, Winter Park, FL 32789
  • /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 $507,925

    Last Listing Agent David Perez COLDWELL BANKER REALTY

    422 S Ranger Blvd, Winter Park, FL 32792
    • /16

      Est $996,024 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

      • $321/SF
      • 55 Days On Market

      Last Sold Price $997,500

      Last Listing Agent Sherri Dyer PREMIER SOTHEBY'S INTL. REALTY

  • /46

    $2,995,000 Pending

    • 5 Beds
    • 4.5 Baths
    • 4,686 Sq Ft

    611 Williams Dr, Winter Park, FL 32789

    Under contract-accepting backup offers. Artistry and exquisite style are brilliantly showcased in this renovated Winter Park masterpiece. Located in the coveted neighborhood of Park Grove, this magical home is sure to take your breath away, with stunning surprises around every corner. Since 2022, the home has undergone an extraordinary transformation in thoughtful renovations, upgrades, and

    MaryStuart Day FANNIE HILLMAN & ASSOCIATES

    611 Williams Dr, Winter Park, FL 32789
  • /2

    $755,000 Sold Jul 18, 2025

    1000 Howell Branch Rd, Winter Park, FL 32789

    • Land
    • 0.55 Acre
    • $1,372,727 per Acre

    Last Sold Summary

    • 30% Below List Price
    • 241 Days On Market

    Current Estimated Value $817,704

    Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

    1000 Howell Branch Rd, Winter Park, FL 32789
    • /19

      Est $2,603,578 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

      • 5% Below List Price
      • $858/SF
      • 0 Days On Market

      Last Sold Price $2,750,000

      Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  • /28

    $292,500

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft

    2519 Windward Way, Winter Park, FL 32792

    Welcome to 2519 Windward Way, a beautifully maintained single-story townhome located in the highly sought-after Windward Square community in Winter Park. This move-in ready residence offers 2 bedrooms, 2 bathrooms, plus a versatile office. Step inside to an open-concept floor plan designed for both everyday living and effortless entertaining. The spacious layout flows seamlessly into a

    Itzel Sotorosa NONA LEGACY POWERED BY LA ROSA

    2519 Windward Way, Winter Park, FL 32792
  • /2

    $3,845,000 Sold May 16, 2025

    2020 Venetian Way, Winter Park, FL 32789

    • 4 Beds
    • 3.5 Baths
    • 4,188 Sq Ft
    • Built 1979

    Last Sold Summary

    • 4% Below List Price
    • $918/SF
    • 4 Days On Market

    Current Estimated Value $3,932,407

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

    2020 Venetian Way, Winter Park, FL 32789
    • /35

      Est $270,856 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

      • 8% Below List Price
      • $229/SF
      • 213 Days On Market

      Last Sold Price $294,999

      Last Listing Agent William Grim, III RE/MAX

  • /25

    $580,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,818 Sq Ft

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789

    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, convenience, and charm in one of Orlando’s

    Courtney Dietch ALL REAL ESTATE & INVESTMENTS

    1807 Hammerlin Ave Unit G, Winter Park, FL 32789
  • /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 $134,450

    Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

    200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
    • /80

      Est $1,157,264 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

      • 4% Below List Price
      • $279/SF
      • 5 Days On Market

      Last Sold Price $1,200,000

      Last Listing Agent Mulcy Tenorio FLORIDA CONNEXION PROPERTIES

  • /46

    $1,974,900

    • 5 Beds
    • 5 Baths
    • 3,953 Sq Ft

    640 Arjay Way, Winter Park, FL 32789

    Price Improvement on this amazing oversized lot! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native

    Farah Bloom KELLER WILLIAMS WINTER PARK

    640 Arjay Way, Winter Park, FL 32789
  • /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 $1,142,505

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

    1150 Kenwood Ave, Winter Park, FL 32789
    • /11

      Est $442,621 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

      • 4% Below List Price
      • $258/SF
      • 99 Days On Market

      Last Sold Price $459,990

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /46

    $399,000 Pending

    • 1 Bed
    • 1 Bath
    • 900 Sq Ft

    311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box, now offered at an improved price of $399,000. This fully renovated one-bedroom, one-bathroom condo spans 900 square feet and offers single-story, ground-floor, corner-unit living just steps from Park Avenue. The 2018 full renovation

    Padgett McCormick KELLY PRICE & COMPANY LLC

    311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
  • /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 $418,193

    Last Listing Agent Michael Cameron CAMERON REALTY GROUP LLC

    1816 Ivy Ln, Winter Park, FL 32792
    • /46

      Est $880,537 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

      • 18% Below List Price
      • $516/SF
      • 119 Days On Market

      Last Sold Price $1,075,000

      Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK

  • /34

    $490,000 Pending

    • 4 Beds
    • 3 Baths
    • 1,378 Sq Ft

    958 Hanover Ave, Winter Park, FL 32789

    Under contract-accepting backup offers. Mother-in-Law suit attached with private entrance on a dead-end street with water view. Welcome to this beautifully remodeled home in the heart of Winter Park, offering the perfect blend of charm, privacy, and convenience. Situated at the end of a quiet street, this unique property provides exceptional privacy while showcasing peaceful views of nearby Lake

    Christopher Lyons AGILE GROUP REALTY

    958 Hanover Ave, Winter Park, FL 32789
  • /2

    $170,000 Sold Sep 24, 2025

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

    • 2 Beds
    • 2 Baths
    • 1,119 Sq Ft
    • Built 1970

    Last Sold Summary

    • 10% Below List Price
    • $152/SF
    • 74 Days On Market

    Current Estimated Value $175,757

    Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

    200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
    • /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

      Last Sold Price $417,500

      Last Listing Agent John Muccigrosso RE/MAX

  • /50

    $1,475,000

    • 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
  • /2

    $475,000 Sold Feb 02, 2026

    1740 Anzle Ave, Winter Park, FL 32789

    • 4 Beds
    • 2 Baths
    • 1,808 Sq Ft
    • Built 1956

    Last Sold Summary

    • 40% Below List Price
    • $263/SF
    • 109 Days On Market

    Current Estimated Value $570,660

    Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

    1740 Anzle Ave, Winter Park, FL 32789
    • /11

      Est $450,044 Not Listed For Sale

      2737 Bright Bird Ln, Winter Park, FL 32792

      • 3 Beds
      • 2.5 Baths
      • 1,782 Sq Ft
      • Built 2023
      2737 Bright Bird Ln, Winter Park, FL 32792

      Last Sold Summary

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

      Last Sold Price $477,790

      Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES

  • /19

    $510,000

    • 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
  • /2

    $350,000 Sold Feb 06, 2026

    1438 Tierra Cir, Winter Park, FL 32792

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • Built 1968

    Last Sold Summary

    • 8% Below List Price
    • $215/SF
    • 3 Days On Market

    Current Estimated Value $398,892

    Last Listing Agent Meir Tenenbaum CARDINAL REALTY GROUP, LLC.

    1438 Tierra Cir, Winter Park, FL 32792
    • /2

      Est $6,270,695 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

      • 4% Above List Price
      • $691/SF
      • 120 Days On Market

      Last Sold Price $6,050,000

      Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  • /51

    $1,395,000

    • 3 Beds
    • 3.5 Baths
    • 2,310 Sq Ft

    1780 Mondrian Cir, Winter Park, FL 32789

    Luxury Lakeview Townhome in Winter Park! Experience elevated living in this newly built 3-bedroom, 3.5-bath residence with over 2,300 sq ft and breathtaking direct views of Lake Killarney. A dramatic 17-ft foyer welcomes you into a bright, open-concept great room featuring 11-ft ceilings and floor-to-ceiling windows that capture stunning water and nature views. The designer kitchen is built for

    Lisa Gould KELLER WILLIAMS WINTER PARK

    1780 Mondrian Cir, Winter Park, FL 32789
  • /2

    $325,000 Sold Oct 03, 2025

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

    • 2 Beds
    • 1 Bath
    • 1,140 Sq Ft
    • Built 1986

    Last Sold Summary

    • 6% Below List Price
    • $285/SF
    • 0 Days On Market

    Current Estimated Value $324,067

    Last Listing Agent Tyler Gibson LPT REALTY, LLC

    260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
    • /21

      Est $436,729 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

      • 3% Above List Price
      • $221/SF
      • 1 Day On Market

      Last Sold Price $421,990

      Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC

  • /41

    $599,997

    • 4 Beds
    • 2 Baths
    • 2,096 Sq Ft

    1985 Japonica Rd, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. New Price Adjusted, Welcome to 1985 Japonica Rd-your newly reimagined Winter Park retreat! This beautifully updated 4-bedroom, 2-bath home offers a perfect blend of contemporary design, comfort, and smart living. Featuring a NEW 2023 roof, 2023 A/C, fresh interiors, and a bright open layout, this home is truly move-in ready. The gourmet kitchen

    Maria Monaco La Rosa Realty Llc

    1985 Japonica Rd, Winter Park, FL 32792

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