Homes in ZIP Code 32789

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  $1,025,000 Sold Jun 27, 2025

  2680 Oglesby Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,546 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Below List Price
  • $403/SF
  • 55 Days On Market

  Current Estimated Value $1,016,846

  Last Listing Agent Kris Kennedy COMPASS FLORIDA LLC

  2680 Oglesby Ave, Winter Park, FL 32789
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  /30

  Est $451,857 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 1,227 Sq Ft

  311 E Morse Blvd Unit 6-4, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-4, Winter Park, FL 32789
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  /41

  $123,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit C214, Winter Park, FL 32789

  Charming 2-bedroom, 1-bath condo located in the heart of Winter Park. This well-maintained unit offers comfortable living with an open layout, ample natural light, and convenient access to shopping, and dining. Enjoy the community pool and beautifully landscaped grounds, perfect for relaxing or entertaining. Ideal for first-time buyers, investors, or anyone looking to enjoy the Winter Park

  Diana Perez PROFESSIONAL REAL ESTATE TEAM

  1695 Lee Rd Unit C214, Winter Park, FL 32789
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  /2

  $5,250,000 Sold Mar 31, 2025

  210 Chelton Cir, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 5,264 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $997/SF
  • 125 Days On Market

  Current Estimated Value $1,309,179

  Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

  210 Chelton Cir, Winter Park, FL 32789
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  /35

  Est $192,773 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 233, Winter Park, FL 32789

  2500 Lee Rd Unit 233, Winter Park, FL 32789
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  /4

  $1,399,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,984 Sq Ft

  1540 Miller Ave, Winter Park, FL 32789

  Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community! This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shopping, dining, and entertainment Winter Park is famous for, this home combines convenience, style, and

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1540 Miller Ave, Winter Park, FL 32789
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  /2

  $2,400,000 Sold Mar 28, 2025

  1010 N Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,074 Sq Ft
  • Built 2017

  Last Sold Summary

  • 14% Below List Price
  • $589/SF
  • 94 Days On Market

  Current Estimated Value $2,409,666

  Last Listing Agent Dana Laing BHHS FLORIDA REALTY

  1010 N Pennsylvania Ave, Winter Park, FL 32789
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  /2

  Est $246,889 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 205, Winter Park, FL 32789

  1250 S Denning Dr Unit 205, Winter Park, FL 32789
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  /49

  $190,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 208, Winter Park, FL 32789

  This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water is included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to

  Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 208, Winter Park, FL 32789
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  /2

  $1,050,000 Sold Jul 14, 2025

  795 W Canton Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,374 Sq Ft
  • Built 2017

  Last Sold Summary

  • 9% Below List Price
  • $442/SF
  • 23 Days On Market

  Current Estimated Value $1,056,510

  Last Listing Agent Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

  795 W Canton Ave, Winter Park, FL 32789
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  /26

  Est $1,440,041 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,304 Sq Ft

  311 E Morse Blvd Unit 1-3, Winter Park, FL 32789

  311 E Morse Blvd Unit 1-3, Winter Park, FL 32789
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  /30

  $3,100,000

  • 5 Beds
  • 4.5 Baths
  • 3,896 Sq Ft

  457 E New England Ave, Winter Park, FL 32789

  Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, setting the tone for the timeless character found throughout. Step inside to a gracious foyer accented

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  457 E New England Ave, Winter Park, FL 32789
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  /2

  $1,480,000 Sold Sep 19, 2025

  1742 Barcelona Way, Winter Park, FL 32789

  • 5 Beds
  • 8 Baths
  • 3,626 Sq Ft
  • Built 1973

  Last Sold Summary

  • 18% Below List Price
  • $408/SF
  • 81 Days On Market

  Current Estimated Value $1,500,180

  Last Listing Agent Dee Morgan KELLY PRICE & COMPANY LLC

  1742 Barcelona Way, Winter Park, FL 32789
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  /2

  Est $223,122 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 107, Winter Park, FL 32789

  2500 Lee Rd Unit 107, Winter Park, FL 32789
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  /24

  $215,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 13, Winter Park, FL 32789

  Welcome to 851 Miles Ave #13, a beautifully renovated 2-bedroom, 1-bathroom second-floor condo in the heart of charming Winter Park, FL 32789! Meticulously updated since 2023, this home blends modern luxury with effortless comfort and is truly move-in ready.As you step inside, you’ll be greeted by elegant porcelain tile flooring throughout—offering both durability and a look that’s easy to

  Eric Campbell LPT REALTY, LLC

  851 Miles Ave Unit 13, Winter Park, FL 32789
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  /2

  $1,500,000 Sold May 14, 2025

  1741 Pine Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,297 Sq Ft
  • Built 2002

  Last Sold Summary

  • $455/SF
  • 7 Days On Market

  Current Estimated Value $1,529,759

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1741 Pine Ave, Winter Park, FL 32789
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  /2

  Est $224,430 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 903 Sq Ft

  1250 S Denning Dr Unit 124, Winter Park, FL 32789

  1250 S Denning Dr Unit 124, Winter Park, FL 32789
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  /24

  $449,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,490 Sq Ft

  1347 Orchid Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Exceptional opportunity This 4-bedroom, 2-bath property offers approximately 1,490 square feet of living space features a spacious backyard and is ideally located just minutes from Downtown Winter Park, within the highly desirable 32789 zip code. It is within close distance to Mead Botanical Garden and just over one mile from Rollins College. With ongoing

  Ken Sheldon SHELDON PROFESSIONALS INC

  1347 Orchid Ave, Winter Park, FL 32789
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  /2

  $560,000 Sold Aug 19, 2025

  1339 Orchid Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 789 Sq Ft
  • Built 1953

  Last Sold Summary

  • 12% Below List Price
  • $710/SF
  • 46 Days On Market

  Current Estimated Value $550,957

  Last Listing Agent Barbara Allen ABIDE REALTY

  1339 Orchid Ave, Winter Park, FL 32789
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  /30

  Est $223,352 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 104, Winter Park, FL 32789

  2500 Lee Rd Unit 104, Winter Park, FL 32789
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  /36

  $1,299,000 Pending

  • 4 Beds
  • 4 Baths
  • 3,116 Sq Ft

  1429 Chapman Cir, Winter Park, FL 32789

  Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophisticated 4-bedroom, 4-bathroom residence seamlessly blends modern luxury with practical living across two thoughtfully planned levels.The striking exterior features geometric lines, stacked stone accents, and dramatic double entry doors, setting the tone for the remarkable

  Greg Martinez CORCORAN PREMIER REALTY

  1429 Chapman Cir, Winter Park, FL 32789
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  /2

  $475,000 Sold Oct 14, 2025

  621 Symonds Ave, Winter Park, FL 32789

  • Land
  • 0.13 Acre
  • $3,653,846 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 147 Days On Market

  Current Estimated Value $474,333

  Last Listing Agent Emily Williams FANNIE HILLMAN & ASSOCIATES

  621 Symonds Ave, Winter Park, FL 32789
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  /2

  Est $328,587 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft

  700 Melrose Ave Unit H3, Winter Park, FL 32789

  700 Melrose Ave Unit H3, Winter Park, FL 32789
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  /64

  $3,190,000

  • 5 Beds
  • 4.5 Baths
  • 4,091 Sq Ft

  670 Williams Dr, Winter Park, FL 32789

  This stunning custom residence built by respected Winter Park Builder Charles Clayton blends classic elegance with refined modern comfort, offering seamless indoor–outdoor living and impeccable craftsmanship throughout. From the manicured lawn and stately traditional exterior to the welcoming front porch with old Detroit brick, the home’s curb appeal sets a tone of understated luxury, all wrapped

  Brian Mitnik RE/MAX 200 REALTY

  670 Williams Dr, Winter Park, FL 32789
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  /2

  $230,000 Sold May 30, 2025

  1500 Gay Rd Unit 10C, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Below List Price
  • $224/SF
  • 75 Days On Market

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 10C, Winter Park, FL 32789
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  /21

  Est $306,236 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,035 Sq Ft

  700 Melrose Ave Unit E1, Winter Park, FL 32789

  700 Melrose Ave Unit E1, Winter Park, FL 32789
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  /21

  $625,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,433 Sq Ft

  2811 Eastern Pkwy, Winter Park, FL 32789

  Under contract-accepting backup offers. Mid-Century Modern architecture meets modern comfort in this beautifully updated Winter Park home. Clean lines, open sightlines, and warm architectural details create a timeless aesthetic that feels both stylish and inviting from the moment you arrive. Inside, the home features an open-concept layout with multiple living areas—ideal for entertaining or

  Laura Leigh Wood RE/MAX TOWN & COUNTRY REALTY

  2811 Eastern Pkwy, Winter Park, FL 32789
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  /2

  $1,740,000 Sold Aug 29, 2025

  443 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,964 Sq Ft
  • Built 1983

  Last Sold Summary

  • 3% Below List Price
  • $587/SF
  • 0 Days On Market

  Current Estimated Value $1,758,882

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  443 Beloit Ave, Winter Park, FL 32789
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  /22

  Est $1,075,593 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,599 Sq Ft

  100 S Virginia Ave Unit 402, Winter Park, FL 32789

  100 S Virginia Ave Unit 402, Winter Park, FL 32789
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  /14

  $2,679,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,520 Sq Ft

  426 Worthington Dr, Winter Park, FL 32789

  Under Construction. Designed with intention and built with precision, this brand-new LUIH Luxury home exemplifies the elegance and livability Winter Park is known for. Every inch of this residence has been curated for those who demand extraordinary design, flawless craftsmanship, and a lifestyle that feels both elevated and effortless. Step through the front door and into a grand two-story foyer

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  426 Worthington Dr, Winter Park, FL 32789
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  /2

  $940,000 Sold Aug 29, 2025

  1840 Biscayne Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,646 Sq Ft
  • Built 2024

  Last Sold Summary

  • 1% Below List Price
  • $355/SF
  • 17 Days On Market

  Current Estimated Value $947,178

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1840 Biscayne Dr, Winter Park, FL 32789
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  /2

  Est $674,732 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,529 Sq Ft

  350 Carolina Ave Unit 207, Winter Park, FL 32789

  350 Carolina Ave Unit 207, Winter Park, FL 32789
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  /84

  $5,895,000 Pending

  • 5 Beds
  • 9 Baths
  • 7,916 Sq Ft

  1400 Alabama Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the

  Rachel Peters THE AGENCY FL

  1400 Alabama Dr, Winter Park, FL 32789
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  /2

  $1,525,000 Sold Jun 18, 2025

  747 Mcintyre Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,457 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $1,047/SF
  • 2 Days On Market

  Current Estimated Value $1,502,651

  Last Listing Agent Chuck Massab FANNIE HILLMAN & ASSOCIATES

  747 Mcintyre Ave, Winter Park, FL 32789
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  /23

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 9C, Winter Park, FL 32789

  1500 Gay Rd Unit 9C, Winter Park, FL 32789
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  /41

  $879,000

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789

  Welcome to The Cloisters, one of Winter Park’s established lakefront communities, ideally between Park Avenue and Lake Osceola. This top-floor residence, rarely available in the building, offers a turnkey lifestyle with exceptional updates and peaceful water views. The home’s oversized screened balcony, complete with a custom awning, creates an uncommon open-air retreat that overlooks the

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 503, Winter Park, FL 32789
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  /2

  $360,000 Sold Nov 20, 2025

  611 Ololu Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Above List Price
  • $314/SF
  • 7 Days On Market

  Last Listing Agent Amanda Johnson HOMERUN REALTY, LLC

  611 Ololu Dr, Winter Park, FL 32789
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  /2

  Est $240,571 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 810 Sq Ft

  700 Melrose Ave Unit H1, Winter Park, FL 32789

  700 Melrose Ave Unit H1, Winter Park, FL 32789
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  /26

  $345,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment. Located on the first floor, this beautifully renovated 2-bed, 2-bath home features an open

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /2

  $1,000,500 Sold Dec 11, 2025

  210 E Rockwood Way, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,431 Sq Ft
  • Built 1950

  Last Sold Summary

  • $699/SF
  • 0 Days On Market

  Last Listing Agent Penny Puente DALTON WADE INC

  210 E Rockwood Way, Winter Park, FL 32789

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