Homes in ZIP Code 32789

• 

  

  

  /22

  $575,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  720 W Webster Ave, Winter Park, FL 32789

  Discover the charm of Winter Park living in this beautifully maintained 1950s home, where convenience and comfort meet modern updates. Just minutes from Park Avenue and Winter Park Village, this 3-bedroom, 2-bath residence offers a lifestyle surrounded by boutique shopping, dining, and cultural experiences.Inside, rich wood flooring, natural light, and thoughtful touches create a warm and

  Brian Hyser THE AGENCY ORLANDO

  720 W Webster Ave, Winter Park, FL 32789
• 

  

  /2

  $1,110,000 Sold Aug 26, 2025

  233 Hampden Place, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 2,813 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $395/SF
  • 7 Days On Market

  Current Estimated Value $1,161,867

  Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

  233 Hampden Place, Winter Park, FL 32789
• 

  

  

  /47

  Est $1,422,611 Not Listed For Sale

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

  518 W Swoope Ave, Winter Park, FL 32789

  518 W Swoope Ave, Winter Park, FL 32789
• 

  

  

  /25

  $329,900

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

  Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
• 

  

  /2

  $1,575,000 Sold Dec 27, 2024

  2435 Chantilly Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,055 Sq Ft
  • Built 2023

  Last Sold Summary

  • 5% Below List Price
  • $516/SF
  • 42 Days On Market

  Current Estimated Value $1,580,443

  Last Listing Agent Aleksey Volchek FLORIDA REALTY INVESTMENTS

  2435 Chantilly Ave, Winter Park, FL 32789
• 

  

  /7

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,585 Sq Ft

  512 W Swoope Ave, Winter Park, FL 32789

  512 W Swoope Ave, Winter Park, FL 32789
• 

  

  /19

  $739,000

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

  300 Carolina Ave Unit 201, Winter Park, FL 32789

  Experience the best of Winter Park living in this beautifully updated 2-bedroom, 2-bath condominium located in the highly sought-after Park West Condominiums. Perfectly situated just steps from Park Avenue’s restaurants, boutique shops, cafés, and the weekly farmers market, this second-floor residence offers both comfort and convenience in one of Central Florida’s most desirable neighborhoods.

  Teri Webster LPT REALTY, LLC

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

  /2

  $3,200,000 Sold Nov 04, 2025

  1900 W Fawsett Rd, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $696/SF
  • 6 Days On Market

  Last Listing Agent Bianca Rey KELLER WILLIAMS WINTER PARK

  1900 W Fawsett Rd, Winter Park, FL 32789
• 

  

  /13

  Est $1,365,719 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,666 Sq Ft

  500 W Swoope Ave, Winter Park, FL 32789

  500 W Swoope Ave, Winter Park, FL 32789
• 

  

  /45

  $1,630,000 New Construction

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting

  Kelly Price KELLY PRICE & COMPANY LLC

  607 Ellen Dr, Winter Park, FL 32789
• 

  /2

  $879,000 Sold Nov 14, 2025

  451 Fairfax Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,227 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $395/SF
  • 5 Days On Market

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

  451 Fairfax Ave, Winter Park, FL 32789
• 

  

  /32

  Est $2,422,915 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,288 Sq Ft

  170 S Phelps Ave, Winter Park, FL 32789

  170 S Phelps Ave, Winter Park, FL 32789
• 

  

  /22

  $298,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake

  Chris Creegan CREEGAN GROUP

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
• 

  /2

  $630,000 Sold Aug 11, 2025

  1792 Killarney Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,264 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Below List Price
  • $278/SF
  • 1 Day On Market

  Current Estimated Value $633,705

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1792 Killarney Dr, Winter Park, FL 32789
• 

  

  /14

  Est $1,290,367 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,585 Sq Ft

  506 W Swoope Ave, Winter Park, FL 32789

  506 W Swoope Ave, Winter Park, FL 32789
• 

  

  /3

  $3,650,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,719 Sq Ft

  207 E Kings Way, Winter Park, FL 32789

  Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediately commands attention with its double-entry driveway, framed by manicured landscaping and a sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  207 E Kings Way, Winter Park, FL 32789
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  /2

  $755,000 Sold Jul 18, 2025

  1000 Howell Branch Rd, Winter Park, FL 32789

  • Land
  • 0.55 Acre
  • $1,372,727 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 241 Days On Market

  Current Estimated Value $855,172

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1000 Howell Branch Rd, Winter Park, FL 32789
• 

  /2

  Est $1,478,058 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft

  1009 S Pennsylvania Ave, Winter Park, FL 32789

  1009 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /34

  $725,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  770 W Webster Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Stop the car! Check out this classic 4/2 Florida ranch PLUS vacant lot ready for renovation! Newer roof, water heater. HW and tile floors, screened porch, utility/storage room. 1 car carport. OR develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave, Winter Park, FL 32789
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  /2

  $325,000 Sold Oct 03, 2025

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 0 Days On Market

  Last Listing Agent Tyler Gibson LPT REALTY, LLC

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
• 

  /2

  Est $1,951,773 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,228 Sq Ft

  643 Pansy Ave, Winter Park, FL 32789

  643 Pansy Ave, Winter Park, FL 32789
• 

  

  /67

  $895,000 Pending

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

  1802 Arbor Park Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Situated in the highly sought-after Winter Park area and surrounded by tree-lined streets, this stunning move-in ready home is waiting for its new owner. Set on one of the largest lots in the neighborhood, the property greets you with style and charm. Professional landscaping leads you to an inviting open floor plan designed for both family life and

  Jennifer Roberts FLORIDA EXECUTIVE REALTY

  1802 Arbor Park Dr, Winter Park, FL 32789
• 

  /2

  $2,835,000 Sold Nov 24, 2025

  255 Stirling Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,635 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $780/SF
  • 25 Days On Market

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

  255 Stirling Ave, Winter Park, FL 32789
• 

  

  /31

  Est $982,283 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,903 Sq Ft

  842 English Ct, Winter Park, FL 32789

  842 English Ct, Winter Park, FL 32789
• 

  

  /43

  $525,000 Pending

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

  1817 Jessica Ct, Winter Park, FL 32789

  Under contract-accepting backup offers. Beautifully situated on an elevated 50-by-106-foot lot in the Waterbridge community, this spacious single-story home enjoys a quiet cul-de-sac setting overlooking a small neighborhood park and is adjacent to a green space that enhances privacy. The property has wonderful curb appeal with mature trees, a wide driveway, an oversized two-car garage, and an

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1817 Jessica Ct, Winter Park, FL 32789
• 

  /2

  $1,430,000 Sold Nov 10, 2025

  1011 Mckean Cir, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,230 Sq Ft
  • Built 1955

  Last Sold Summary

  • $641/SF
  • 0 Days On Market

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  1011 Mckean Cir, Winter Park, FL 32789
• 

  

  /30

  Est $893,783 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,828 Sq Ft

  826 W Lyman Ave, Winter Park, FL 32789

  826 W Lyman Ave, Winter Park, FL 32789
• 

  

  /12

  $1,690,000

  • Land
  • 0.51 Acre
  • $3,313,725 per Acre

  141 W Lake Sue Ave, Winter Park, FL 32789

  AMAZING Winter Park Opportunity! Nestled in one of the most desirable locations, 141 W Lake Sue Avenue offers a VERY HARD to find 1⁄2 acre lot—the epitome of prime real estate. Making this a rare chance for builders or buyers to create their dream Winter Park residence on this corner lot at Glencoe & Lake Sue Avenue. Surrounded by beautiful homes and tree-lined streets, this pristine lot provides

  Brian Mitnik RE/MAX 200 REALTY

  141 W Lake Sue Ave, Winter Park, FL 32789
• 

  /2

  $439,900 Sold Jul 22, 2025

  1945 Bering Ave, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft
  • Built 1958

  Last Sold Summary

  • $279/SF
  • 6 Days On Market

  Current Estimated Value $434,268

  Last Listing Agent Carmen Gonzalez, Pa HORIZON WEST REALTY

  1945 Bering Ave, Winter Park, FL 32789
• 

  /2

  Est $1,492,850 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,700 Sq Ft

  1571 Sunset Dr, Winter Park, FL 32789

  1571 Sunset Dr, Winter Park, FL 32789
• 

  

  /50

  $1,250,000

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. You will be amazed at this fully remodeled one level four bedroom home on a fenced corner lot. This home has amazing curb appeal, with its wide half circle paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living

  Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  $799,000 Sold Apr 08, 2025

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 2,331 Sq Ft
  • Built 1952

  Last Sold Summary

  • $343/SF
  • 3 Days On Market

  Current Estimated Value $833,747

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

  Unlisted Address
• 

  /2

  Est $2,212,052 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,640 Sq Ft

  1770 Oakhurst Ave, Winter Park, FL 32789

  1770 Oakhurst Ave, Winter Park, FL 32789
• 

  

  /36

  $1,050,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  632 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards

  Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

  632 Country Club Dr, Winter Park, FL 32789
• 

  /2

  $2,575,000 Sold Oct 20, 2025

  1341 Place Picardy, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,469 Sq Ft
  • Built 2016

  Last Sold Summary

  • 8% Below List Price
  • $576/SF
  • 95 Days On Market

  Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

  1341 Place Picardy, Winter Park, FL 32789
• 

  

  /29

  Est $618,420 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,054 Sq Ft

  1400 Indiana Ave, Winter Park, FL 32789

  1400 Indiana Ave, Winter Park, FL 32789
• 

  

  /63

  $2,165,000

  • 5 Beds
  • 4 Baths
  • 4,798 Sq Ft

  2001 Lake Dr, Winter Park, FL 32789

  Nestled on a quiet cul-de-sac in the heart of Winter Park, this canal-front residence offers the perfect balance of elegance and lifestyle. With direct access to Lake Killarney, the home invites days filled with boating, fishing, and entertaining poolside. Offering a total of 4,798 heated square feet, the property includes the main residence with 3,798 square feet plus a 1,000-square-foot

  Brian Hyser THE AGENCY ORLANDO

  2001 Lake Dr, Winter Park, FL 32789
• 

  /2

  $1,000,000 Sold Feb 18, 2025

  193 Overlook Rd, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 2,201 Sq Ft
  • Built 1925

  Last Sold Summary

  • 17% Below List Price
  • $454/SF
  • 44 Days On Market

  Current Estimated Value $1,000,691

  Last Listing Agent Kimberley Gernert BALDWIN PARK REALTY LLC

  193 Overlook Rd, Winter Park, FL 32789
• 

  

  /18

  Est $1,341,463 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,399 Sq Ft

  621 Huntington Ave, Winter Park, FL 32789

  621 Huntington Ave, Winter Park, FL 32789
• 

  

  /51

  $5,900,000

  • 6 Beds
  • 5.5 Baths
  • 5,759 Sq Ft

  887 Georgia Ave, Winter Park, FL 32789

  Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue.This stately 6-bedroom, 5.5-bathroom home

  Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  887 Georgia Ave, Winter Park, FL 32789

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