Homes in ZIP Code 32789

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  /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

  $375,000 Sold Apr 28, 2025

  2259 Minnesota Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,015 Sq Ft
  • Built 1948

  Last Sold Summary

  • 10% Below List Price
  • $369/SF
  • 11 Days On Market

  Current Estimated Value $378,516

  Last Listing Agent Kayla Barnes LPT REALTY, LLC

  2259 Minnesota Ave, Winter Park, FL 32789
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  /13

  Est $1,362,508 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
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  /24

  $1,249,000

  • 3 Beds
  • 2 Baths
  • 1,907 Sq Ft

  1836 Grinnell Terrace, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. This light-filled home features wide-plank flooring, recessed lighting, and all new modern fixtures. The entryway features comfortable seating, built in cabinets with an electric

  Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

  1836 Grinnell Terrace, Winter Park, FL 32789
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  /2

  $280,000 Sold Jun 27, 2025

  2446 Lotafun Ave, Winter Park, FL 32789

  • Land
  • 0.17 Acre
  • $1,647,059 per Acre

  Last Sold Summary

  • 7% Below List Price
  • 123 Days On Market

  Current Estimated Value $286,333

  Last Listing Agent David Francetic COLDWELL BANKER RESIDENTIAL RE

  2446 Lotafun Ave, Winter Park, FL 32789
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  /32

  Est $2,400,273 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
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  /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

  $1,877,500 Sold Apr 01, 2025

  1446 Berkshire Ave, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,612 Sq Ft
  • Built 1925

  Last Sold Summary

  • 15% Below List Price
  • $407/SF
  • 5 Days On Market

  Current Estimated Value $1,871,116

  Last Listing Agent Jimmy Hendrickson SERHANT

  1446 Berkshire Ave, Winter Park, FL 32789
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  /2

  Est $1,460,424 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
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  /12

  $1,500,000

  • Land
  • 0.51 Acre
  • $2,941,176 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 half an 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

  Brian Mitnik RE/MAX 200 REALTY

  141 W Lake Sue Ave, Winter Park, FL 32789
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  /2

  $5,400,000 Sold Jul 14, 2025

  541 Virginia Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,725 Sq Ft
  • Built 2008

  Last Sold Summary

  • 14% Below List Price
  • $1,143/SF
  • 152 Days On Market

  Current Estimated Value $5,143,011

  Last Listing Agent Keith Moore HOMEVEST REALTY

  541 Virginia Dr, Winter Park, FL 32789
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  /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
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  /36

  $1,165,000 Open Sun 2PM - 4PM

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

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

  Located right in the heart of the exclusive Winter Park, one street over from Park Avenue, boasting lake views, you will find this newly completed posh, high end jewel box which has been extensively remodeled with elevated bespoke finishes by W DESIGNS LTD. Every surface has been reimagined and thoroughly thought out featuring, large format Calcutta Gold marble floors, harlequin marble floors,

  Ruth Harris COLDWELL BANKER RESIDENTIAL RE

  100 S Interlachen Ave Unit 404, Winter Park, FL 32789
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  /2

  $1,305,000 Sold Nov 05, 2025

  1600 Barcelona Way, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,014 Sq Ft
  • Built 1972

  Last Sold Summary

  • 12% Below List Price
  • $433/SF
  • 175 Days On Market

  Current Estimated Value $1,351,087

  Last Listing Agent Laura Ascenso LPT REALTY, LLC

  1600 Barcelona Way, Winter Park, FL 32789
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  /31

  Est $984,221 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
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  /55

  $1,495,000

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  106 S Interlachen Ave Unit 118, Winter Park, FL 32789

  OPEN HOUSE - SATURDAY, 02/07, FROM 11 AM TO 1 PM. Experience lakefront living in the heart of Winter Park. One of only two residences in The Cloisters with soaring 9-foot ceilings, this first-floor, three-bedroom, two-bath home offers a rare blend of privacy, scale and panoramic Lake Osceola views. Nestled just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  106 S Interlachen Ave Unit 118, Winter Park, FL 32789
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  /2

  $130,000 Sold Nov 05, 2025

  1695 Lee Rd Unit C206, Winter Park, FL 32789

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

  Last Sold Summary

  • 4% Below List Price
  • $148/SF
  • 43 Days On Market

  Current Estimated Value $131,986

  Last Listing Agent Justin Adams EXP REALTY LLC

  1695 Lee Rd Unit C206, Winter Park, FL 32789
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  /30

  Est $944,152 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
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  /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
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  /2

  $995,000 Sold Jul 22, 2025

  1821 Windsor Dr, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,188 Sq Ft
  • Built 2017

  Last Sold Summary

  • 10% Below List Price
  • $455/SF
  • 25 Days On Market

  Current Estimated Value $1,048,300

  Last Listing Agent Chris Creegan CREEGAN GROUP

  1821 Windsor Dr, Winter Park, FL 32789
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  /2

  Est $1,489,783 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
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  /63

  $2,150,000

  • 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 FL

  2001 Lake Dr, Winter Park, FL 32789
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  /2

  $750,000 Sold Oct 02, 2025

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1971

  Last Sold Summary

  • 3% Below List Price
  • $592/SF
  • 0 Days On Market

  Last Listing Agent Michael Ford FANNIE HILLMAN & ASSOCIATES

  100 S Interlachen Ave Unit 203D, Winter Park, FL 32789
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  /2

  Est $2,301,942 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
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  /51

  $5,700,000

  • 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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  /2

  $1,300,000 Sold Oct 02, 2025

  857 Brock St, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,288 Sq Ft
  • Built 1964

  Last Sold Summary

  • $568/SF
  • 0 Days On Market

  Current Estimated Value $1,278,927

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

  857 Brock St, Winter Park, FL 32789
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  /29

  Est $618,235 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
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  /27

  $700,000

  • 3 Beds
  • 2 Baths
  • 1,407 Sq Ft

  865 S Pennsylvania Ave, Winter Park, FL 32789

  LOCATION, LOCATION, LOCATION...Desirable Winter Park "College Quarter" Historic District...Come take a tour of this wonderfully updated Bungalow with lots of windows for natural light, original hardwood floors, beautiful crown molding, and high ceilings. Did I mention the location, Walk to Park Ave, Rollins College, Hannibal Square, Mead Gardens, and Lake Virginia. Looking to "House Hack" then

  Jose Vega LPT REALTY, LLC

  865 S Pennsylvania 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 $1,599,171

  Last Listing Agent John McDade FANNIE HILLMAN & ASSOCIATES

  279 Rippling Ln, Winter Park, FL 32789
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  /18

  Est $1,262,323 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
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  /25

  $169,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 232, Winter Park, FL 32789

  Just steps from the shore of 239-acre, spring-fed Lake Killarney, welcome to Lakeside Manor and true lakefront living. This charming 1-bedroom, 1-bath second-floor end-unit condo offers partial lake views, private lake access, and an inviting blend of comfort and convenience. Residents enjoy exceptional community amenities including a lakefront pool and clubhouse with stunning water views, a

  Wendy Rodriguez COLDWELL BANKER RESIDENTIAL RE

  2500 Lee Rd Unit 232, 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 $2,033,626

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

  2915 Parkland Dr, Winter Park, FL 32789
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  /59

  Est $2,388,963 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,870 Sq Ft

  1411 Elizabeth Dr, Winter Park, FL 32789

  1411 Elizabeth Dr, Winter Park, FL 32789
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  /70

  $435,000

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

  2249 Minnesota Ave, Winter Park, FL 32789

  FFANTASTIC WINTER PARK BUNGALOW — JUST LISTED! Nestled on a charming, tree-lined street in the highly sought-after Dubsdread District of Winter Park/College Park, this exceptional home offers rare golf course views and an unbeatable location. Perfectly positioned adjacent to the 6th tee box, 2249 Minnesota Avenue blends timeless mid-century character with privacy, space, and modern updates.

  Emily Nickley MARKET CONNECT REALTY LLC

  2249 Minnesota 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 $1,579,657

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

  1541 Chestnut Ave, Winter Park, FL 32789
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  /57

  Est $822,157 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 2,327 Sq Ft

  25 Stymie Place, Winter Park, FL 32789

  25 Stymie Place, Winter Park, FL 32789
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  /25

  $2,999,500 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,737 Sq Ft

  1229 Via Del Mar, Winter Park, FL 32789

  New construction by M. Lahr Homes, Orlando and Winter Park's premier custom home builder. This 5-bedroom, 5.5-bathroom home is situated on a 90' x 142' wide lot in the prestigious "Vias" neighborhood of Winter Park! The location is walking distance to the Winter Park Racquet Club and a short drive to Interlachen Country Club and Park Avenue. Don't miss an amazing opportunity to build a custom

  Erin Lahr CHARLES RUTENBERG REALTY ORLANDO

  1229 Via Del Mar, 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

  Current Estimated Value $751,161

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  311 Cortland Ave, Winter Park, FL 32789
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  /15

  Est $380,765 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,075 Sq Ft

  24 Stymie Place, Winter Park, FL 32789

  24 Stymie Place, Winter Park, FL 32789
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  /16

  $2,990,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,711 Sq Ft

  1494 Westchester Ave, Winter Park, FL 32789

  Under Construction. Welcome to Westchester Avenue—an exceptional new construction residence just moments from the iconic Park Avenue in Winter Park, celebrated for its upscale dining, refined cafés, and luxury boutique shopping. This custom-built home exemplifies true craftsmanship, showcasing elegant architecture and exquisite finishes throughout. No expense was spared in its creation. From the

  Caitlin Dos Santos EXP REALTY LLC

  1494 Westchester Ave, Winter Park, FL 32789

Showing Results 321 - 360, Page 9 of 18