Homes in ZIP Code 32789

• 

  

  /2

  Est $195,962 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  851 Miles Ave Unit 3, Winter Park, FL 32789

  851 Miles Ave Unit 3, Winter Park, FL 32789
• 

  

  

  /47

  $925,000

  • 4 Beds
  • 3.5 Baths
  • 2,173 Sq Ft

  208 Brewer Ave, Winter Park, FL 32789

  Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thoughtfully designed living space. From the moment you arrive, the charm is undeniable—with classic architectural details and a welcoming front porch that set the tone for what’s inside. All major items have been taken care of as well allowing you to just move on in, HVAC 2021, ROOF

  Cassandra King COMPASS FLORIDA LLC

  208 Brewer Ave, Winter Park, FL 32789
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  /2

  $1,587,500 Sold Jul 31, 2025

  279 Rippling Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,472 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Below List Price
  • $457/SF
  • 318 Days On Market

  Current Estimated Value $1,593,040

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  279 Rippling Ln, Winter Park, FL 32789
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  /32

  Est $189,360 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 111, Winter Park, FL 32789

  2500 Lee Rd Unit 111, Winter Park, FL 32789
• 

  

  

  /15

  $750,000 Pending

  • Land
  • 0.45 Acre
  • $1,666,667 per Acre

  2002 Karolina Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. A unique opportunity in unincorporated Orange County, these three contiguous residential lots, each approximately 0.15 acres, totaling 0.45 acres or 20,244 square feet, are offered together as a prime redevelopment site. Zoned R-2, this assemblage is positioned adjacent to some of Winter Park’s most vibrant retail and restaurant corridors, including

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  2002 Karolina Ave, Winter Park, FL 32789
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  /2

  $2,155,000 Sold Aug 23, 2025

  2915 Parkland Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,356 Sq Ft
  • Built 2025

  Last Sold Summary

  • $642/SF

  Current Estimated Value $1,905,732

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

  2915 Parkland Dr, Winter Park, FL 32789
• 

  

  /16

  Est $259,341 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft

  1250 S Denning Dr Unit 203, Winter Park, FL 32789

  1250 S Denning Dr Unit 203, Winter Park, FL 32789
• 

  

  /49

  $1,215,000

  • 6 Beds
  • 4 Baths
  • 2,284 Sq Ft

  726 and 720 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 and 720 N Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $1,607,160 Sold Aug 01, 2025

  1541 Chestnut Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft
  • Built 2018

  Last Sold Summary

  • 4% Above List Price
  • $566/SF
  • 2 Days On Market

  Current Estimated Value $1,575,060

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

  1541 Chestnut Ave, Winter Park, FL 32789
• 

  

  /21

  Est $240,989 Not Listed For Sale

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

  1500 Gay Rd Unit 25A, Winter Park, FL 32789

  1500 Gay Rd Unit 25A, Winter Park, FL 32789
• 

  /2

  $2,450,000

  • 5 Beds
  • 5.5 Baths
  • 4,010 Sq Ft

  1771 Taylor Ave, Winter Park, FL 32789

  Custom Winter Park home completed in 2019 by FG Schaub Custom Home Builder. Contemporary Florida living awaits in this newly built home, boasting a spacious open floor plan spanning over 4,000 square feet with five bedrooms and five-and-a-half baths. Delight in the stunning gourmet kitchen, gas cooktop, oversized island and an extended walk-in pantry with cabinets. Distinctive features include

  Michelle Hochfelder PREMIER SOTHEBY'S INTL. REALTY

  1771 Taylor Ave, Winter Park, FL 32789
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  /2

  $750,000 Sold Sep 25, 2025

  311 Cortland Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft
  • Built 1952

  Last Sold Summary

  • 6% Below List Price
  • $543/SF
  • 48 Days On Market

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  311 Cortland Ave, Winter Park, FL 32789
• 

  

  /20

  Est $201,904 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 136, Winter Park, FL 32789

  2500 Lee Rd Unit 136, Winter Park, FL 32789
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  /47

  $733,000

  • 3 Beds
  • 2 Baths
  • 1,761 Sq Ft

  3018 Northwood Blvd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. "MOVE-IN READY", 3-BED, 2-FULL BATHS, SINGLE FAMILY HOME WITH A LARGE PRIVATE YARD, WINTER PARK, FL 32789. This AMAZING LOCATION just off Corrine Drive is walking distance to East End Market and zoned for TOP-RATED Audubon Park (K-8) & Winter Park High (Magnet Program) Schools. The Owners completed a DETAILED HOME ADDITION & UPDATE in 2020 with over

  Joe Bornstein ROCK SPRINGS REALTY, LLC

  3018 Northwood Blvd, Winter Park, FL 32789
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  /2

  $259,000 Sold Aug 29, 2025

  1250 S Denning Dr Unit 111, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Built 1967

  Last Sold Summary

  • $285/SF
  • 76 Days On Market

  Current Estimated Value $255,628

  Last Listing Agent Alayna Phillips EXP REALTY LLC

  1250 S Denning Dr Unit 111, Winter Park, FL 32789
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  /20

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft

  1500 Gay Rd Unit 6C, Winter Park, FL 32789

  1500 Gay Rd Unit 6C, Winter Park, FL 32789
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  /44

  $1,595,000 Pending

  • 4 Beds
  • 4 Baths
  • 2,743 Sq Ft

  1780 Mizell Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 1780 Mizell Avenue, a masterpiece where timeless charm meets modern luxury. This 4-bedroom, 4-bathroom plus office single-family residence offers 2,743 square feet of finely curated living space designed for the discerning buyer who values sophistication, comfort, and convenience. Perfectly positioned just moments from downtown Winter Park’s

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  1780 Mizell Ave, Winter Park, FL 32789
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  /2

  $435,000 Sold Jun 06, 2025

  693 Minnesota Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft
  • Built 2000

  Last Sold Summary

  • $419/SF

  Current Estimated Value $432,524

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

  693 Minnesota Ave, Winter Park, FL 32789
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  /73

  Est $2,443,123 Not Listed For Sale

  • 3 Beds
  • 5 Baths
  • 3,244 Sq Ft

  125 S Interlachen Ave Unit 2, Winter Park, FL 32789

  125 S Interlachen Ave Unit 2, Winter Park, FL 32789
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  /7

  $800,000

  • Land
  • 0.19 Acre
  • $4,210,526 per Acre

  1770 Bryan Ave, Winter Park, FL 32789

  Discover a truly unique offering in the heart of Winter Park! 1770 Bryan Avenue is now on the market along with the adjoining lots at 1760 and 1780 Bryan Avenue, creating a rare opportunity to own three consecutive parcels in one of Central Florida’s most desirable communities.While each property is being sold and priced separately, buyers have the option to purchase one, two, or all three

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1770 Bryan Ave, Winter Park, FL 32789
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  /2

  $505,000 Sold Feb 07, 2025

  2341 Mulbry Dr, Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,165 Sq Ft
  • Built 1952

  Last Sold Summary

  • 4% Below List Price
  • $433/SF
  • 0 Days On Market

  Current Estimated Value $514,612

  Last Listing Agent Rachael Klinker DAHLIA REALTY GROUP

  2341 Mulbry Dr, Winter Park, FL 32789
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  /31

  Est $226,629 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 207, Winter Park, FL 32789

  2500 Lee Rd Unit 207, Winter Park, FL 32789
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  /37

  $179,000 Pending

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 219, Winter Park, FL 32789

  Welcome to life on Lake Killarney, one of Winter Park’s most sought-after lakefront communities! This charming 2-bedroom, 1-bathroom condo offers an unbeatable location and resort-style amenities—perfect for those seeking the true Florida lifestyle.Enjoy direct access to Lake Killarney, where residents can take advantage of boat slips available at a low cost on a first-come, first-serve basis, as

  Nicole Van Treese SUNDIAL REAL ESTATE LLC

  2500 Lee Rd Unit 219, Winter Park, FL 32789
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  /2

  $530,000 Sold Oct 02, 2025

  1409 Sunset Dr, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 1,107 Sq Ft
  • Built 1930

  Last Sold Summary

  • 2% Above List Price
  • $479/SF
  • 4 Days On Market

  Last Listing Agent Ahmad Karain R MICHAELS REALTY LLC

  1409 Sunset Dr, Winter Park, FL 32789
• 

  

  /23

  Est $223,238 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit K4, Winter Park, FL 32789

  700 Melrose Ave Unit K4, Winter Park, FL 32789
• 

  

  /38

  $975,000

  • 3 Beds
  • 2 Baths
  • 1,887 Sq Ft

  913 Moss Ln, Winter Park, FL 32789

  ***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL – A 2023 Masterpiece Awaits! Step into luxury living at 913 Moss Lane, a breathtakingly renovated 3-bedroom, 2-bath haven in the heart of Winter Park, boasting 1,887 square feet of modern elegance and timeless Florida charm.

  Peter Rodriguez VECTOR REALTY

  913 Moss Ln, Winter Park, FL 32789
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  /2

  $1,100,000 Sold Mar 28, 2025

  567 Osceola Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,651 Sq Ft
  • Built 1912

  Last Sold Summary

  • 12% Below List Price
  • $415/SF
  • 42 Days On Market

  Current Estimated Value $1,107,347

  Last Listing Agent Susannah Dance COLDWELL BANKER RESIDENTIAL RE

  567 Osceola Ave, Winter Park, FL 32789
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  /26

  Est $542,518 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 970 Sq Ft

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789
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  /7

  $1,390,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,253 Sq Ft

  501 Lakeview Ave, Winter Park, FL 32789

  Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  501 Lakeview Ave, Winter Park, FL 32789
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  /2

  $760,000 Sold Jun 09, 2025

  2838 Wright Ave, Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,128 Sq Ft
  • Built 1952

  Last Sold Summary

  • 5% Below List Price
  • $674/SF
  • 2 Days On Market

  Current Estimated Value $732,965

  Last Listing Agent Jordan Suglio BALDWIN PARK REALTY LLC

  2838 Wright Ave, Winter Park, FL 32789
• 

  

  /22

  Est $215,865 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  700 Melrose Ave Unit E26, Winter Park, FL 32789
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  /48

  $2,350,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 4,506 Sq Ft

  2412 Chantilly Ave, Winter Park, FL 32789

  Step into a world of modern elegance in this newly completed estate in the heart of Winter Park. Masterfully constructed, this five-bedroom residence with six full and one half baths spans over 4,500 square feet of luxurious design and comfort. From the moment you enter the soaring foyer, light pours through expansive windows that frame every angle of the open floor plan, creating a seamless

  Josh Hill THE AGENCY ORLANDO

  2412 Chantilly Ave, Winter Park, FL 32789
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  /2

  $341,000 Sold Aug 08, 2025

  2827 Euston Rd, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Built 1956

  Last Sold Summary

  • 20% Below List Price
  • $217/SF
  • 205 Days On Market

  Current Estimated Value $345,113

  Last Listing Agent Evelyn Tejada REGENCY REAL ESTATE LLC

  2827 Euston Rd, Winter Park, FL 32789
• 

  

  /18

  Est $178,476 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

  1250 S Denning Dr Unit 107, Winter Park, FL 32789

  1250 S Denning Dr Unit 107, Winter Park, FL 32789
• 

  

  /30

  $515,000

  • 4 Beds
  • 2 Baths
  • 1,718 Sq Ft

  240 Orange Terrace Dr, Winter Park, FL 32789

  MOVE IN READY - NO HOA, PRIME WINTER PARK LOCATION, CLOSE TO I-4! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to offer.Fully renovated in 2021—including new

  Susan Pinnock A+ REALTY PROFESSIONALS, INC

  240 Orange Terrace Dr, Winter Park, FL 32789
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  /2

  $2,288,215 Sold Dec 19, 2025

  1602 Alabama Dr Unit 404, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,709 Sq Ft
  • Built 1981

  Last Sold Summary

  • 8% Below List Price
  • $845/SF
  • 179 Days On Market

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1602 Alabama Dr Unit 404, Winter Park, FL 32789
• 

  

  /30

  Est $723,223 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789
• 

  /2

  $505,000 Pending

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

  1651 N Park Ave, Winter Park, FL 32789

  Winter Park home for sale

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  1651 N Park Ave, Winter Park, FL 32789
• 

  /2

  $4,100,000 Sold Feb 03, 2025

  1231 Via Salerno, Winter Park, FL 32789

  • 5 Beds
  • 7 Baths
  • 5,633 Sq Ft
  • Built 2005

  Last Sold Summary

  • 11% Below List Price
  • $728/SF
  • 116 Days On Market

  Current Estimated Value $4,226,415

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

  1231 Via Salerno, Winter Park, FL 32789
• 

  

  /29

  Est $999,722 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  100 S Interlachen Ave Unit 201, Winter Park, FL 32789

  100 S Interlachen Ave Unit 201, Winter Park, FL 32789

Showing Results 361 - 400, Page 10 of 18