Homes in ZIP Code 32789

• 

  

  /2

  Est $1,200,069

  Not Listed For Sale

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,734 Sq Ft
  • Built 2008

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789

  Last Sold Summary

  • 184 Days On Market
• 

  

  

  /46

  $1,300,000

  • 4 Beds
  • 3 Baths
  • 2,075 Sq Ft

  3006 Northwood Blvd, Winter Park, FL 32789

  Reimagined from the ground up for modern living while honoring its original mid-century modern heritage, this 1953 Winter Park residence pairs authentic MCM character with the ease of all-new finishes and systems. Four bedrooms and three full bathrooms are arranged around an open living, dining, and kitchen core that opens to a light-filled sitting area. White oak floors run throughout, while

  Daren Ellington ORLANDO HOMES GROUP LLC

  3006 Northwood Blvd, 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 $699,216

  Last Listing Agent Teri Webster LPT REALTY, LLC

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

  

  /2

  Est $295,644

  Not Listed For Sale

  500 N Pennsylvania Ave Unit G, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft
  • Built 1981

  500 N Pennsylvania Ave Unit G, Winter Park, FL 32789

  Last Sold Summary

  • 76 Days On Market
• 

  

  

  /41

  $879,000

  Pending

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

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

  Under contract-accepting backup offers. 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

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 503, 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 $603,434

  Last Listing Agent Jean Chalifour COLDWELL BANKER REALTY

  843 W Swoope Ave, Winter Park, FL 32789
• 

  /2

  Est $323,537

  Not Listed For Sale

  1132 Park Green Place, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1991

  1132 Park Green Place, Winter Park, FL 32789

  Last Sold Summary

  • 1 Day On Market
• 

  

  /5

  $5,000

  • 3 Beds
  • 2 Baths
  • 1,840 Sq Ft

  2355 Devon Ct, Winter Park, FL 32789

  Foreclosure Auction Ends July 7, 2026 at 11:00 AM EST. Explore this charming 3-bedroom, 2-bath residence set in a peaceful and well-located Winter Park community. The list price is the opening bid for the online auction. Sold As-is.

  Jamie Boone Jamie L Boone LLC

  2355 Devon Ct, Winter Park, FL 32789
• 

  /2

  $2,280,000

  Sold Jun 08, 2026

  436 N Knowles Ave, Winter Park, FL 32789

  • Land
  • 11,325 Sq Ft
  • $8,769,231 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 0 Days On Market

  Current Estimated Value $764,000

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

  436 N Knowles Ave, Winter Park, FL 32789
• 

  /2

  Est $677,221

  Not Listed For Sale

  1580 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1971

  1580 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • 4 Days On Market
• 

  

  /27

  $3,500,000

  • 4 Beds
  • 3.5 Baths
  • 4,036 Sq Ft

  2240 Venetian Way, Winter Park, FL 32789

  Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Chain of Lakes. This home, built by Liberty Development, with 4-bedrooms plus two bonus rooms blends elegance with comfortable everyday living. The main level offers a dedicated office area, formal dining room, and an inviting gathering room with

  Johnny Hurlburt COLDWELL BANKER REALTY

  2240 Venetian Way, 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 $1,779,248

  Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC

  690 Williams Dr, Winter Park, FL 32789
• 

  /2

  Est $892,909

  Not Listed For Sale

  1762 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1957

  1762 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • 37 Days On Market
• 

  

  /12

  $4,500,000

  $499K PRICE DROP

  • Land
  • 20,908 Sq Ft
  • $9,375,000 per Acre

  503 N Interlachen Ave, Winter Park, FL 32789

  JUST LISTED - RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,999,000!!! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed

  Kelly Price KELLY PRICE & COMPANY LLC

  503 N Interlachen Ave, 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 $2,442,271

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1700 Palm Ave, Winter Park, FL 32789
• 

  /2

  Est $1,871,774

  Not Listed For Sale

  1530 Via Tuscany, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft
  • Built 1972

  1530 Via Tuscany, Winter Park, FL 32789

  Last Sold Summary

  • 377 Days On Market
• 

  

  /44

  $989,500

  • 1 Bed
  • 1.5 Baths
  • 1,109 Sq Ft

  269 E Canton Ave Unit 269, Winter Park, FL 32789

  Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine

  Catherine Williams COLDWELL BANKER REALTY

  269 E Canton Ave Unit 269, Winter Park, FL 32789
• 

  /2

  $1,425,000

  Sold May 19, 2026

  850 Juanita Rael, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,306 Sq Ft
  • Built 1966

  Last Sold Summary

  • $618/SF
  • 4 Days On Market

  Current Estimated Value $1,415,112

  Last Listing Agent Brad Grosberg PHIL KEAN REAL ESTATE LLC

  850 Juanita Rael, Winter Park, FL 32789
• 

  /2

  Est $726,133

  Not Listed For Sale

  678 Depugh St, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 1,940 Sq Ft
  • Built 1952

  678 Depugh St, Winter Park, FL 32789

  Last Sold Summary

  • 89 Days On Market
• 

  

  /70

  $3,875,000

  New Construction $322K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 4,782 Sq Ft

  1782 Pine Ave, Winter Park, FL 32789

  (HUGE PRICE REDUCTION & NEWLY ENHANCED REAR LANDSCAPING ADDED FOR EXCEPTIONAL PRIVACY AND MORE SECLUDED OUTDOOR LIVING EXPERIENCE) Step into this stunning West-Indies inspired luxury home crafted by Nautilus Homes, where tropical charm meets timeless elegance. An architectural masterpiece in the City of Winter Park. This five-bedroom seven-bath home that includes a private in-law suite offers

  Prentice Williams KELLER WILLIAMS ADVANTAGE REALTY

  1782 Pine Ave, Winter Park, FL 32789
• 

  /2

  $1,688,750

  Sold Apr 01, 2026

  1705 Elizabeths Walk, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 3,820 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Above List Price
  • $442/SF
  • 3 Days On Market

  Current Estimated Value $1,701,350

  Last Listing Agent Keith Moore HOMEVEST REALTY

  1705 Elizabeths Walk, Winter Park, FL 32789
• 

  /2

  Est $984,967

  Not Listed For Sale

  1875 Lake Spier Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft
  • Built 1958

  1875 Lake Spier Dr, Winter Park, FL 32789

  Last Sold Summary

  • 33 Days On Market
• 

  

  /81

  $429,900

  Open Sat 12AM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft

  2249 Minnesota Ave, Winter Park, FL 32789

  Welcome to one of Orlando's most beloved neighborhoods, where tree-lined streets, golf course views, and a true sense of community create the lifestyle buyers are searching for. Perfectly positioned across from the 5th tee of historic Dubsdread Golf Course, this beautifully renovated home places you in the heart of the Dubsdread bubble—just minutes from the dining, shopping, and charm of both

  Emily Nickley MARKET CONNECT REALTY LLC

  2249 Minnesota Ave, Winter Park, FL 32789
• 

  /2

  $895,000

  Sold Dec 29, 2025

  1802 Arbor Park Dr, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,808 Sq Ft
  • Built 1968

  Last Sold Summary

  • $495/SF
  • 1 Day On Market

  Current Estimated Value $979,206

  Last Listing Agent Jennifer Roberts FLORIDA EXECUTIVE REALTY

  1802 Arbor Park Dr, Winter Park, FL 32789
• 

  /2

  Est $989,364

  Not Listed For Sale

  1265 Park Pointe Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1989

  1265 Park Pointe Ln, Winter Park, FL 32789

  Last Sold Summary

  • 4 Days On Market
• 

  

  /75

  $6,000,000

  • 5 Beds
  • 8 Baths
  • 7,397 Sq Ft

  1571 Woodland Ave, Winter Park, FL 32789

  Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of-a-kind exceptional estate offers more than 7,300 square feet across three beautifully designed levels, blendingrefined luxury with modern comfort.Rich architectural details include solid red oak flooring with a walnut finish, nearly 10-foot ceilings, stackedcrown

  Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  1571 Woodland 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 $471,862

  Last Listing Agent Alex Vastardis COLDWELL BANKER REALTY

  2381 Roxbury Rd, Winter Park, FL 32789
• 

  /2

  Est $444,004

  Not Listed For Sale

  1501 Michigan Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 853 Sq Ft
  • Built 1936

  1501 Michigan Ave, Winter Park, FL 32789

  Last Sold Summary

  • 5 Days On Market
• 

  

  /59

  $2,189,000

  Pending

  • 5 Beds
  • 4 Baths
  • 3,374 Sq Ft

  230 E Rockwood Way, Winter Park, FL 32789

  JUST LISTED! Located in the highly sought-after Winter Park Lake Sue area, this exceptional contemporary residence offers a rare opportunity to enjoy luxury living among some of the most architecturally significant and beautifully designed homes in Central Florida. Positioned within one of the region's most desirable neighborhoods, the property combines modern design, exceptional functionality,

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  230 E Rockwood Way, Winter Park, FL 32789
• 

  /2

  $1,942,000

  Sold Jul 14, 2025

  1394 Stewart St, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 3,907 Sq Ft
  • Built 1961

  Last Sold Summary

  • 12% Below List Price
  • $497/SF
  • 50 Days On Market

  Current Estimated Value $1,964,805

  Last Listing Agent Richard Vaughn REALTY ONE GROUP INSPIRATION

  1394 Stewart St, Winter Park, FL 32789
• 

  

  /56

  Est $1,752,292

  Not Listed For Sale

  914 Moss Ln, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,431 Sq Ft
  • Built 1955

  914 Moss Ln, Winter Park, FL 32789

  Last Sold Summary

  • 2 Days On Market
• 

  

  /36

  $1,249,000

  • 4 Beds
  • 3 Baths
  • 2,871 Sq Ft

  363 N Phelps Ave, Winter Park, FL 32789

  This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate

  Chris Creegan CREEGAN GROUP

  363 N Phelps Ave, Winter Park, FL 32789
• 

  /2

  $540,000

  Sold Dec 29, 2025

  1817 Jessica Ct, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,870 Sq Ft
  • Built 1981

  Last Sold Summary

  • 3% Above List Price
  • $289/SF
  • 3 Days On Market

  Current Estimated Value $544,913

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1817 Jessica Ct, Winter Park, FL 32789
• 

  

  /39

  Est $1,080,453

  Not Listed For Sale

  1771 Bryan Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,507 Sq Ft
  • Built 1993

  1771 Bryan Ave, Winter Park, FL 32789

  Last Sold Summary

  • 42 Days On Market
• 

  

  /85

  $4,285,000

  • 4 Beds
  • 5.5 Baths
  • 4,066 Sq Ft

  1441 Cardinal Ct, Winter Park, FL 32789

  Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style, it offers luxury finishes paired with a warm, comfortable feel. The home features 4,060 square feet, including four en-suite bedrooms, five full bathrooms, a powder bath, and a bonus room with a built-in office. The spacious

  Damian Bergler CHARLES RUTENBERG REALTY ORLANDO

  1441 Cardinal Ct, Winter Park, FL 32789
• 

  /2

  $1,100,000

  Sold Apr 15, 2026

  100 S Interlachen Ave Unit 404, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 1971

  Last Sold Summary

  • 8% Below List Price
  • $902/SF
  • 51 Days On Market

  Current Estimated Value $1,125,415

  Last Listing Agent Ruth Harris COLDWELL BANKER REALTY

  100 S Interlachen Ave Unit 404, Winter Park, FL 32789
• 

  

  /38

  Est $1,826,548

  Not Listed For Sale

  580 Palmer Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 3,055 Sq Ft
  • Built 1950

  580 Palmer Ave, Winter Park, FL 32789

  Last Sold Summary

  • 36 Days On Market
• 

  

  /12

  $1,750,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,350 Sq Ft

  1840 Anzle Ave, Winter Park, FL 32789

  Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everything. This beautifully crafted home features 4 bedrooms, 2.5 bathrooms, and 2,350 square feet of living space, plus an additional 1,247 square feet of terraces and lanai. The open-concept kitchen showcases quartz countertops,

  Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENT

  1840 Anzle Ave, Winter Park, FL 32789
• 

  /2

  $429,999

  Sold Oct 21, 2025

  105 Conrad Ct, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,573 Sq Ft
  • Built 1958

  Last Sold Summary

  • $273/SF
  • 24 Days On Market

  Current Estimated Value $444,863

  Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

  105 Conrad Ct, Winter Park, FL 32789
• 

  

  /64

  Est $706,343

  Not Listed For Sale

  260 Rippling Ln, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,179 Sq Ft
  • Built 1954

  260 Rippling Ln, Winter Park, FL 32789

  Last Sold Summary

  • 9 Days On Market

Showing Results 601 - 640, Page 16 of 18