Homes in ZIP Code 32789

• 

  

  

  /56

  Est $1,427,087 Not Listed For Sale

  106 S Interlachen Ave Unit 219, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1971

  106 S Interlachen Ave Unit 219, Winter Park, FL 32789

  Last Sold Summary

  • 17% Below List Price
  • $884/SF
  • 21 Days On Market

  Last Sold Price $1,725,000

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
• 

  

  

  /9

  $944,890 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,662 Sq Ft

  Lot #21 Karolina Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Step into a life where charm meets convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath residence offers 2,662 square feet of thoughtfully designed living space and sits on a 6,748 square foot lot. The home showcases modern architecture with clean lines and the comfort and functionality today’s homeowners desire. This is the final opportunity

  Vinny Lay COMPASS FLORIDA LLC

  Lot #21 Karolina Ave, Winter Park, FL 32789
• 

  

  /2

  $243,800 Sold May 30, 2025

  255 Sandlewood Trail, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Below List Price
  • $254/SF
  • 24 Days On Market

  Last Listing Agent Freddie Crespo INVESTOR'S REAL ESTATE LLC

  255 Sandlewood Trail, Winter Park, FL 32789
• 

  

  

  /28

  Est $548,932 Not Listed For Sale

  100 S Interlachen Ave Unit 108, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 901 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 108, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $577/SF
  • 2 Days On Market

  Last Sold Price $520,000

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES
• 

  

  

  /70

  $1,495,000

  • 4 Beds
  • 4 Baths
  • 3,226 Sq Ft

  340 Alberta Dr, Winter Park, FL 32789

  Welcome to 340 Alberta Drive, a beautifully maintained 4-bedroom, 4-bath residence with a new roof installed in 2020. Situated on a spacious .30-acre lot in the heart of Winter Park, this home features an open and functional layout with all the bedrooms on the main floor and a versatile upstairs bonus room. Highlights include a pool and spa, ideal for year-round enjoyment, and a 3-car garage

  Pilar Ulloa REAL ESTATE FIRM OF ORLANDO

  340 Alberta Dr, Winter Park, FL 32789
• 

  /2

  $810,000 Sold Nov 26, 2025

  1314 Canterbury Rd, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 1950

  Last Sold Summary

  • $466/SF

  Current Estimated Value $795,300

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

  1314 Canterbury Rd, Winter Park, FL 32789
• 

  /2

  Est $342,540 Not Listed For Sale

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789

  • 1 Bed
  • 1.5 Baths
  • 726 Sq Ft
  • Built 1972

  535 N Interlachen Ave Unit 304, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $482/SF
  • 82 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Jennifer Cornette HOLT REAL ESTATE LLC
• 

  

  /45

  $3,590,000 Open Sat 12PM - 2PM

  • 5 Beds
  • 7 Baths
  • 4,520 Sq Ft

  1751 Glencoe Rd, Winter Park, FL 32789

  Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed Davila Homes masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural details, a sweeping driveway, and detached garage that together set a tone of timeless sophistication.

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  1751 Glencoe Rd, Winter Park, FL 32789
• 

  /2

  $1,180,000 Sold May 01, 2025

  181 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,000 Sq Ft
  • Built 1948

  Last Sold Summary

  • 13% Below List Price
  • $393/SF
  • 43 Days On Market

  Current Estimated Value $1,267,241

  Last Listing Agent Iluska Kruse ORLANDO BROTHERS REAL ESTATE LLC

  181 N Phelps Ave, Winter Park, FL 32789
• 

  /2

  Est $669,159 Not Listed For Sale

  350 Carolina Ave Unit 304, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,523 Sq Ft
  • Built 2005

  350 Carolina Ave Unit 304, Winter Park, FL 32789

  Last Sold Summary

  • $440/SF
  • 61 Days On Market

  Last Sold Price $670,000

  Last Listing Agent Jennifer Tyre REALTY AND COMPANY INT., LLC
• 

  

  /34

  $1,599,000

  • 3 Beds
  • 3.5 Baths
  • 3,459 Sq Ft

  1340 Place Picardy, Winter Park, FL 32789

  Set on an oversized 1/3-acre lot in the heart of Winter Park, this one-owner home was custom built in 1997 and has been meticulously maintained ever since. Solid block construction, timeless stone accents, and mature landscaping give it great curb appeal from the moment you arrive. Step inside to a spacious foyer with hardwood floors that carry through most of the main living areas. To the right,

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  1340 Place Picardy, Winter Park, FL 32789
• 

  /2

  $2,495,000 Sold Jul 21, 2025

  1690 Palm Ave, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 3,967 Sq Ft
  • Built 2020

  Last Sold Summary

  • 12% Below List Price
  • $629/SF
  • 56 Days On Market

  Current Estimated Value $2,534,909

  Last Listing Agent Daniel Robinson HOUWZER INC

  1690 Palm Ave, Winter Park, FL 32789
• 

  /2

  Est $598,030 Not Listed For Sale

  250 Carolina Ave Unit 406, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,306 Sq Ft
  • Built 1981

  250 Carolina Ave Unit 406, Winter Park, FL 32789

  Last Sold Summary

  • 18% Above List Price
  • $387/SF
  • 15 Days On Market

  Last Sold Price $505,000

  Last Listing Agent Gina Johnson RE/MAX
• 

  

  /36

  $3,135,000 Open Sat 2PM - 4PM

  • 5 Beds
  • 5.5 Baths
  • 3,863 Sq Ft

  1821 Englewood Rd, Winter Park, FL 32789

  This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean architectural lines with timeless finishes and thoughtful design details. An elegant foyer immediately

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1821 Englewood Rd, Winter Park, FL 32789
• 

  /2

  $1,075,000 Sold Jul 31, 2025

  1690 Oneco Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,703 Sq Ft
  • Built 1967

  Last Sold Summary

  • 10% Below List Price
  • $398/SF
  • 140 Days On Market

  Current Estimated Value $1,121,293

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

  1690 Oneco Ave, Winter Park, FL 32789
• 

  /2

  Est $138,987 Not Listed For Sale

  1695 Lee Rd Unit E213, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  1695 Lee Rd Unit E213, Winter Park, FL 32789

  Last Sold Summary

  • 9% Below List Price
  • $173/SF
  • 28 Days On Market

  Last Sold Price $152,000

  Last Listing Agent Justin Adams EXP REALTY LLC
• 

  

  /67

  $3,978,900 Open Sun 12PM - 2PM

  • 4 Beds
  • 4.5 Baths
  • 4,353 Sq Ft

  1117 Kenwood Ave, Winter Park, FL 32789

  Experience the art of luxury living just steps from the boutiques, cafés, and celebrated dining of Park Avenue, Rollins College, and the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle.A thoughtful quad split bedroom layout offers 4 bedrooms and 4.5 baths, including a serene primary

  Domenique Lombardo ROYALTY R E BOUTIQUE INC

  1117 Kenwood Ave, Winter Park, FL 32789
• 

  /2

  $411,250 Sold Mar 27, 2025

  767 Baffie Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,132 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Above List Price
  • $363/SF
  • 2 Days On Market

  Current Estimated Value $409,761

  Last Listing Agent Jeffrey Petch GECKO REALTY, INC

  767 Baffie Ave, Winter Park, FL 32789
• 

  

  /31

  Est $137,509 Not Listed For Sale

  1695 Lee Rd Unit D114, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  1695 Lee Rd Unit D114, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $159/SF
  • 60 Days On Market

  Last Sold Price $140,500

  Last Listing Agent Jodenny Ogando REAL BROKER, LLC
• 

  

  /51

  $1,450,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,223 Sq Ft

  1649 Harmon Ave, Winter Park, FL 32789

  Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1649 Harmon Ave, Winter Park, FL 32789
• 

  /2

  $430,000 Sold May 01, 2025

  328 Lake Fair Ln, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft
  • Built 1958

  Last Sold Summary

  • 1% Above List Price
  • $290/SF
  • 6 Days On Market

  Current Estimated Value $440,707

  Last Listing Agent Tom Langmann RE/MAX 200 REALTY

  328 Lake Fair Ln, Winter Park, FL 32789
• 

  /2

  Est $133,432 Not Listed For Sale

  1695 Lee Rd Unit D205, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  1695 Lee Rd Unit D205, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $159/SF
  • 11 Days On Market

  Last Sold Price $140,000

  Last Listing Agent Martha Grasty EXP REALTY LLC
• 

  

  /40

  $359,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

  Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural Integrity Reserve Study

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789
• 

  /2

  $1,129,000 Sold Dec 10, 2025

  100 S Virginia Ave Unit 314, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,615 Sq Ft
  • Built 2009

  Last Sold Summary

  • $432/SF
  • 4 Days On Market

  Current Estimated Value $1,126,567

  Last Listing Agent Julieta Knapp ACCUMARK PROPERTIES

  100 S Virginia Ave Unit 314, Winter Park, FL 32789
• 

  

  /18

  Est $196,889 Not Listed For Sale

  1695 Lee Rd Unit D202, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Built 1966

  1695 Lee Rd Unit D202, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 15 Days On Market

  Last Sold Price $203,000

  Last Listing Agent Michael Giordano COLDWELL BANKER REALTY
• 

  

  /18

  $2,829,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,018 Sq Ft

  609 S Phelps Ave, Winter Park, FL 32789

  Under Construction. Introducing the newest showpiece from LUIH Luxury Homes, perfectly positioned in the heart of Winter Park. Set on an oversized homesite along a quiet, tree-lined street, this residence immediately captivates with its expansive front lawn and timeless architectural presence. Inside, the home unfolds with a thoughtfully designed and highly functional floor plan that balances

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  609 S Phelps Ave, Winter Park, FL 32789
• 

  /2

  $702,050 Sold Jan 23, 2026

  300 Carolina Ave Unit 201, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1981

  Last Sold Summary

  • 5% Below List Price
  • $538/SF
  • 19 Days On Market

  Current Estimated Value $711,378

  Last Listing Agent Teri Webster LPT REALTY, LLC

  300 Carolina Ave Unit 201, Winter Park, FL 32789
• 

  

  /31

  Est $141,915 Not Listed For Sale

  1695 Lee Rd Unit C203, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  1695 Lee Rd Unit C203, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $179/SF
  • 4 Days On Market

  Last Sold Price $158,000

  Last Listing Agent Zac Hernandez EMPIRE NETWORK REALTY
• 

  

  /39

  $234,999

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  2/2 * IMMACULATE CONDO * LOW HOA * LIVE ON LAKE KILLARNEY * ENJOY PARK AVE IN WINTER PARK * 3 MILES TO ROLLINS COLLEGE * NEW AC * NEW WATER HEATER * NEW INTERIOR PAINT * NEW LIGHTING * Immaculate updated 2 bedroom 2 bathroom Condo in a prime location on beautiful Lake Killarney, a serene oasis in Winter Park. A walkable Lake community providing Residents with direct Lake Access, Private Dock with

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
• 

  /2

  $610,000 Sold Aug 11, 2025

  843 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1962

  Last Sold Summary

  • 10% Below List Price
  • $495/SF
  • 67 Days On Market

  Current Estimated Value $593,144

  Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

  843 W Swoope Ave, Winter Park, FL 32789
• 

  

  /4

  Est $135,043 Not Listed For Sale

  1695 Lee Rd Unit D109, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft
  • Built 1966

  1695 Lee Rd Unit D109, Winter Park, FL 32789

  Last Sold Summary

  • 4% Below List Price
  • $219/SF
  • 0 Days On Market

  Last Sold Price $140,000

  Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES
• 

  

  /32

  $1,125,000

  • 4 Beds
  • 3 Baths
  • 1,808 Sq Ft

  1802 Arbor Park Dr, Winter Park, FL 32789

  Welcome home, perfectly positioned in one of Winter Park’s most desirable communities, The Tree Streets—where mature canopies, pride of ownership, and limited inventory make opportunities like this exceptionally rare. Set on an impressive .27-acre lot (one of the largest in the neighborhood), this 4-bedroom, 3-bath residence offers 1,808 square feet of thoughtfully designed living space with room

  Jorge Perez Gonzalez TBRO REALTY LLC

  1802 Arbor Park Dr, Winter Park, FL 32789
• 

  /2

  $1,770,000 Sold Sep 22, 2025

  690 Williams Dr, Winter Park, FL 32789

  • 3 Beds
  • 4 Baths
  • 3,121 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Below List Price
  • $567/SF
  • 0 Days On Market

  Current Estimated Value $1,773,832

  Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC

  690 Williams Dr, Winter Park, FL 32789
• 

  

  /27

  Est $203,035 Not Listed For Sale

  1695 Lee Rd Unit A115, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Built 1966

  1695 Lee Rd Unit A115, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $196/SF
  • 167 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Justin Adams EXP REALTY LLC
• 

  

  /34

  $299,900

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-19, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you

  Mathew Kelly TURN-KEY MOVES REALTY

  311 E Morse Blvd Unit 7-19, Winter Park, FL 32789
• 

  /2

  $2,440,000 Sold Jul 01, 2025

  1700 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,770 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $647/SF
  • 41 Days On Market

  Current Estimated Value $2,456,290

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1700 Palm Ave, Winter Park, FL 32789
• 

  /2

  Est $141,692 Not Listed For Sale

  1695 Lee Rd Unit A113, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  1695 Lee Rd Unit A113, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $170/SF
  • 0 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Yigit Orer EMPIRE NETWORK REALTY
• 

  

  /28

  $825,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,893 Sq Ft

  1680 Palmer Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. This 1-story home on a corner lot offers easy living in one of Winter Park’s most convenient locations! Enter through a covered front porch and inviting foyer with slate tile floors to discover a desirable split-bedroom floorplan. Off to the right, the spacious primary wing (later addition) serves as a true retreat, with vaulted ceilings, hand-carved wood

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1680 Palmer Ave, Winter Park, FL 32789
• 

  /2

  $470,000 Sold Dec 23, 2025

  2381 Roxbury Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft
  • Built 1949

  Last Sold Summary

  • 8% Below List Price
  • $263/SF
  • 24 Days On Market

  Current Estimated Value $470,047

  Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

  2381 Roxbury Rd, Winter Park, FL 32789
• 

  /2

  Not Listed For Sale

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

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

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

  Last Sold Summary

  • $234/SF
  • 16 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Marci Blanchard KELLER WILLIAMS ADVANTAGE REALTY

Showing Results 561 - 600, Page 15 of 18