Homes in ZIP Code 32789

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  /8

  Not Listed For Sale

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

  1500 Gay Rd Unit 17C, Winter Park, FL 32789

  1500 Gay Rd Unit 17C, Winter Park, FL 32789
• 

  

  

  /10

  $2,590,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,138 Sq Ft

  185 Sylvan Blvd, Winter Park, FL 32789

  Under Construction. Brand-new, meticulously crafted residence built by renowned builder LUIH Homes offering 3,138 square feet of thoughtfully designed living space. As you arrive, the home's stunning architectural façade and detached two-car garage make a striking first impression. Inside, every detail has been carefully curated to offer both sophistication and functionality. Soaring ceilings and

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  185 Sylvan Blvd, Winter Park, FL 32789
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  /2

  $230,000 Sold Feb 21, 2025

  700 Melrose Ave Unit F2, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft
  • Built 1964

  Last Sold Summary

  • 8% Below List Price
  • $315/SF
  • 193 Days On Market

  Current Estimated Value $220,221

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

  700 Melrose Ave Unit F2, Winter Park, FL 32789
• 

  

  /2

  Not Listed For Sale

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

  1500 Gay Rd Unit 8B, Winter Park, FL 32789

  1500 Gay Rd Unit 8B, Winter Park, FL 32789
• 

  

  

  /50

  $1,849,000

  • 5 Beds
  • 7 Baths
  • 3,116 Sq Ft

  1861 Taylor Ave, Winter Park, FL 32789

  This exceptional custom residence, built by Meridian Homes and designed by Zero Latitude, offers a rare combination of thoughtful architecture, high-end finishes, and modern functionality. Interior design by Lauren Ayers Interiors sets a refined tone throughout, complemented by curated details such as Rifle Paper wallpaper, accent walls, and wide-plank hardwood flooring by Britannia

  Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1861 Taylor Ave, Winter Park, FL 32789
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  /2

  $4,430,000 Sold Oct 09, 2025

  2161 Sharon Rd, Winter Park, FL 32789

  • 5 Beds
  • 6.5 Baths
  • 6,338 Sq Ft
  • Built 2023

  Last Sold Summary

  • 11% Below List Price
  • $699/SF
  • 247 Days On Market

  Current Estimated Value $4,110,928

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  2161 Sharon Rd, Winter Park, FL 32789
• 

  

  /30

  Not Listed For Sale

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

  1500 Gay Rd Unit 7B, Winter Park, FL 32789

  1500 Gay Rd Unit 7B, Winter Park, FL 32789
• 

  

  /18

  $4,199,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,891 Sq Ft

  1417 Williams Dr, Winter Park, FL 32789

  Under Construction. Tucked away on a quiet cul-de-sac in the coveted Park Grove community, this home sits on an expansive 0.37-acre lot, just moments from the boutiques, dining, and charm of Park Avenue. The exterior makes a striking first impression with a refined architectural façade that feels both timeless and distinctive. Inside, a dramatic 20-foot foyer welcomes you with abundant natural

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1417 Williams Dr, Winter Park, FL 32789
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  /2

  $519,180 Sold Jul 08, 2025

  2518 Sweetwater Trail, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,205 Sq Ft
  • Built 1965

  Last Sold Summary

  • 21% Below List Price
  • $235/SF
  • 201 Days On Market

  Current Estimated Value $603,460

  Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  2518 Sweetwater Trail, Winter Park, FL 32789
• 

  

  /11

  Est $277,535 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft

  287 Sandlewood Trail Unit 4, Winter Park, FL 32789

  287 Sandlewood Trail Unit 4, Winter Park, FL 32789
• 

  

  /75

  $3,825,000 Pending

  • 5 Beds
  • 7 Baths
  • 4,055 Sq Ft

  1820 Glencoe Rd, Winter Park, FL 32789

  Discover premier Winter Park luxury real estate at 1820 Glencoe Road—a stunning Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located minutes from Park Avenue, Rollins College, and downtown Winter Park, this residence offers the perfect blend of coastal architecture and modern Florida luxury living. With 4,055 sqft. of thoughtfully designed space, this Winter

  Laura Earl CORCORAN PREMIER REALTY

  1820 Glencoe Rd, Winter Park, FL 32789
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  /2

  $1,565,000 Sold Sep 24, 2025

  1450 Glencoe Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,662 Sq Ft
  • Built 1952

  Last Sold Summary

  • 1% Below List Price
  • $588/SF
  • 42 Days On Market

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1450 Glencoe Rd, Winter Park, FL 32789
• 

  

  /35

  Est $268,328 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft

  215 Sandlewood Trail Unit 7, Winter Park, FL 32789

  215 Sandlewood Trail Unit 7, Winter Park, FL 32789
• 

  

  /45

  $895,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft

  1774 Mondrian Cir, Winter Park, FL 32789

  Experience the epitome of luxury lakeside living in Winter Park at our exclusive townhome community. Located in a prime spot, our collection of 30 modern townhomes offer a unique blend of elegance and leisure, with Lake Killarney as your picturesque backdrop. This cutting-edge three-bedroom masterpiece redefines contemporary living, featuring a grand foyer, open-concept kitchen, elegant dining

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1774 Mondrian Cir, Winter Park, FL 32789
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  /2

  $600,000 Sold Apr 04, 2025

  631 Callahan St, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,751 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Below List Price
  • $343/SF
  • 41 Days On Market

  Current Estimated Value $603,574

  Last Listing Agent Yousef Zeidan RE/MAX PRIME PROPERTIES

  631 Callahan St, Winter Park, FL 32789
• 

  

  /17

  Est $329,733 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,098 Sq Ft

  232 Sandlewood Trail Unit 4, Winter Park, FL 32789

  232 Sandlewood Trail Unit 4, Winter Park, FL 32789
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  /27

  $1,295,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,053 Sq Ft

  1602 Alabama Dr Unit 203, Winter Park, FL 32789

  Under contract-accepting backup offers. A spectacular two-bedroom, two-bath home available in the historic Alabama Condominiums. Located on the second floor with breathtaking views of Lake Maitland on the Winter Park Chain of Lakes and the beautiful grounds of The Alabama. Recently renovated with updated bathrooms, and a new kitchen which includes gorgeous cabinets, stone counters and stainless

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1602 Alabama Dr Unit 203, Winter Park, FL 32789
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  /2

  $2,250,000 Sold Nov 17, 2025

  600 Ololu Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,749 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $600/SF
  • 2 Days On Market

  Last Listing Agent David Francetic COLDWELL BANKER RESIDENTIAL RE

  600 Ololu Dr, Winter Park, FL 32789
• 

  

  /40

  Est $456,897 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,214 Sq Ft

  1620 Orange Ave, Winter Park, FL 32789

  1620 Orange Ave, Winter Park, FL 32789
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  /9

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft

  1113 Via Del Mar, Winter Park, FL 32789

  Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceablehomesite offering rare scale, privacy, and extraordinary future build potential. The primaryvalue is in the land, presenting an unparalleled canvas for a custom luxury residence, withvirtually no comparable vacant land available in the immediate vicinity. Set on a tranquil smalllake that

  David Barany BAY HILL REALTY LLC

  1113 Via Del Mar, Winter Park, FL 32789
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  /2

  $645,000 Sold Jun 13, 2025

  796 Mcintyre Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1988

  Last Sold Summary

  • 4% Below List Price
  • $338/SF
  • 18 Days On Market

  Current Estimated Value $652,417

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  796 Mcintyre Ave, Winter Park, FL 32789
• 

  

  /23

  Est $491,110 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,616 Sq Ft

  1769 Indiana Ave Unit D, Winter Park, FL 32789

  1769 Indiana Ave Unit D, Winter Park, FL 32789
• 

  

  /20

  $215,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  151 N Orlando Ave Unit 226, Winter Park, FL 32789

  Take advantage of this newly updated 2 Bedrooms and 1 Bathroom LAKE FRONT condo conveniently located in Winter Park/Orlando next to all of shops and restaurants. With private lake access to launch and dock your watercraft within the community for boating and fishing. Walk to Trader Joes next door and Winter Park Village to enjoy great number of restaurants, movie theater, retail shops and grocery

  Mike Wang LOKATION

  151 N Orlando Ave Unit 226, Winter Park, FL 32789
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  /2

  $260,000 Sold Feb 28, 2025

  700 Melrose Ave Unit B4, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  Last Sold Summary

  • $242/SF
  • 0 Days On Market

  Current Estimated Value $295,199

  Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  700 Melrose Ave Unit B4, Winter Park, FL 32789
• 

  

  /16

  Est $339,894 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 809 Sq Ft

  2038 Jewell Ave, Winter Park, FL 32789

  2038 Jewell Ave, Winter Park, FL 32789
• 

  

  /50

  $3,250,000

  • 5 Beds
  • 5.5 Baths
  • 4,296 Sq Ft

  473 Fletcher Place, Winter Park, FL 32789

  Welcome to the best of Winter Park living, where luxury meets lifestyle and every day feels like a getaway. This stunning custom home, built by Lundev, sits on a quiet, tree-lined street just a mile from Park Avenue and only steps from beautiful Lake Osceola. Imagine walking to brunch on Park Ave, then coming home to launch your paddleboard from the end of your street. From the moment you pull

  Brandon Geers COMPASS FLORIDA LLC

  473 Fletcher Place, Winter Park, FL 32789
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  /2

  $560,000 Sold Jan 27, 2026

  1875 Staunton Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 89 Days On Market

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1875 Staunton Ave, Winter Park, FL 32789
• 

  

  /18

  Est $350,809 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft

  420 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  420 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /7

  $899,000

  • Land
  • 0.19 Acre
  • $4,731,579 per Acre

  731 Midget Dr, Winter Park, FL 32789

  Rare corner lot with stunning views of Lake Midget, located in the heart of Winter Park within an area of modern new-construction homes. This build-ready property offers an exceptional opportunity to create a custom residence in one of the city’s most desirable neighborhoods. Just minutes from Park Avenue and Winter Park Village, with easy access to premier dining, shopping, and

  Juliana Usquiano EMPIRE NETWORK REALTY

  731 Midget Dr, Winter Park, FL 32789
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  /2

  $569,000 Sold May 30, 2025

  1368 Devon Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,642 Sq Ft
  • Built 1952

  Last Sold Summary

  • $347/SF
  • 5 Days On Market

  Current Estimated Value $579,112

  Last Listing Agent Karen Ripperger LPT REALTY, LLC

  1368 Devon Rd, Winter Park, FL 32789
• 

  /2

  Est $349,575 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,204 Sq Ft

  647 Huntington Ave Unit 8, Winter Park, FL 32789

  647 Huntington Ave Unit 8, Winter Park, FL 32789
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  /32

  $1,195,000

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

  100 S Interlachen Ave Unit 415, Winter Park, FL 32789

  Residence 415 at The Cloisters offers a rare opportunity to own a comprehensively rebuilt home in one of Winter Park’s enduring lakefront communities. Set on the fourth floor, just one block from Park Avenue, this residence blends timeless architecture with newly reimagined design. Taken thoughtfully down to its original structure and meticulously reconstructed with longevity in mind, this

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 415, Winter Park, FL 32789
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  /2

  $2,935,000 Sold May 27, 2025

  266 Chase Ave, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,088 Sq Ft
  • Built 1930

  Last Sold Summary

  • 10% Below List Price
  • $718/SF
  • 30 Days On Market

  Current Estimated Value $2,919,753

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  266 Chase Ave, Winter Park, FL 32789
• 

  /2

  Est $819,065 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft

  1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789

  1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789
• 

  

  /49

  $1,250,000

  • 2 Beds
  • 2 Baths
  • 1,402 Sq Ft

  1602 Alabama Dr Unit 403, Winter Park, FL 32789

  Perched on the top floor in the heart of Winter Park, this luxury, open-concept residence offers a rare blend of elevated design and everyday ease. Enjoy the peace of no neighbors above, plus the privacy, security, and lock-and-leave convenience that only condo living can provide without sacrificing space, light, or lifestyle. The Alabama delivers a rare Winter Park combo of modern living and

  Matthew Burks CORCORAN PREMIER REALTY

  1602 Alabama Dr Unit 403, Winter Park, FL 32789
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  /2

  $2,100,000 Sold Jul 07, 2025

  104 Cortland Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 1926

  Last Sold Summary

  • 12% Below List Price
  • $660/SF
  • 36 Days On Market

  Current Estimated Value $2,108,527

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  104 Cortland Ave, Winter Park, FL 32789
• 

  

  /90

  Est $864,192 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft

  1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789

  1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789
• 

  

  /68

  $948,000

  • 3 Beds
  • 2 Baths
  • 2,114 Sq Ft

  250 Cortland Ave, Winter Park, FL 32789

  Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

  Alexandra Nordine EXP REALTY LLC

  250 Cortland Ave, Winter Park, FL 32789
• 

  /2

  $749,000 Sold Aug 01, 2025

  1429 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,939 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $386/SF
  • 63 Days On Market

  Current Estimated Value $756,540

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  1429 Indiana Ave, Winter Park, FL 32789
• 

  

  /37

  Est $316,174 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 830 Sq Ft

  1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

Showing Results 641 - 680, Page 17 of 18