Homes in ZIP Code 32789

• 

  

  

  /43

  $1,225,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,292 Sq Ft

  67 Cypress Ln, Maitland, FL 32751

  Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside to discover hardwood floors flowing

  Kelly Price KELLY PRICE & COMPANY LLC

  67 Cypress Ln, Maitland, FL 32751
• 

  

  /2

  $4,800,000 Sold Jan 02, 2026

  641 Bonita Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 6,699 Sq Ft
  • Built 1948

  Last Sold Summary

  • 4% Below List Price
  • $717/SF
  • 0 Days On Market

  Current Estimated Value $4,728,758

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  641 Bonita Dr, Winter Park, FL 32789
• 

  

  

  /21

  Est $231,298 Not Listed For Sale

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

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

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

  Last Sold Summary

  • 2% Below List Price
  • $229/SF
  • 5 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK
• 

  

  

  /47

  $1,165,000

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

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

  Perfectly positioned just one street from iconic Park Avenue, this exceptional Winter Park residence is a masterclass in refined luxury and bespoke design. With unobstructed views often lush landscape and lake views from coveted fourth-floor vantage point, this one-of-a-kind pied-'a-terre has been completely transformed by W DESIGNS LTD. into a sophisticated sanctuary with an old-world Ritz

  Ruth Harris COLDWELL BANKER REALTY

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

  

  /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 $1,160,351

  Last Listing Agent Susannah Dance COLDWELL BANKER REALTY

  567 Osceola Ave, Winter Park, FL 32789
• 

  

  /20

  Est $192,657 Not Listed For Sale

  2500 Lee Rd Unit 136, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft
  • Built 1969

  2500 Lee Rd Unit 136, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $229/SF
  • 41 Days On Market

  Last Sold Price $195,000

  Last Listing Agent Kelly Hildebrand FANNIE HILLMAN & ASSOCIATES
• 

  

  /55

  $1,450,000

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

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

  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. Just two blocks from Park Avenue and adjacent to the Alfond Inn, this condominium lives like a private residence with unmatched access to boutique

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

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

  /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 $732,384

  Last Listing Agent Jordan Suglio BALDWIN PARK REALTY LLC

  2838 Wright Ave, Winter Park, FL 32789
• 

  

  /20

  Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft
  • Built 1972

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

  Last Sold Summary

  • $266/SF
  • 8 Days On Market

  Last Sold Price $195,000

  Last Listing Agent Jerry Oller FANNIE HILLMAN & ASSOCIATES
• 

  

  /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

  $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 $345,254

  Last Listing Agent Evelyn Tejada REGENCY REAL ESTATE LLC

  2827 Euston Rd, Winter Park, FL 32789
• 

  

  /73

  Est $2,432,391 Not Listed For Sale

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

  • 3 Beds
  • 5 Baths
  • 3,244 Sq Ft
  • Built 2020

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

  Last Sold Summary

  • 5% Above List Price
  • $717/SF
  • 120 Days On Market

  Last Sold Price $2,325,000

  Last Listing Agent Andrea Sider, PA KELLER WILLIAMS WINTER PARK
• 

  

  /51

  $5,000,000 Pending

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

  887 Georgia Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. 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

  Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  887 Georgia Ave, Winter Park, FL 32789
• 

  /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
• 

  

  /31

  Est $214,864 Not Listed For Sale

  2500 Lee Rd Unit 207, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft
  • Built 1969

  2500 Lee Rd Unit 207, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $241/SF
  • 36 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Carlos Santana REALTY SERVICES OF AMERICA LLC
• 

  

  /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
• 

  /2

  $699,000 Sold Jul 31, 2025

  1891 Bryan Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft
  • Built 1989

  Last Sold Summary

  • $431/SF
  • 14 Days On Market

  Current Estimated Value $706,151

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1891 Bryan Ave, Winter Park, FL 32789
• 

  /2

  Est $287,507 Not Listed For Sale

  700 Melrose Ave Unit B4, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  700 Melrose Ave Unit B4, Winter Park, FL 32789

  Last Sold Summary

  • 11% Above List Price
  • $242/SF
  • 0 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC
• 

  

  /58

  $3,295,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,897 Sq Ft

  700 Pinetree Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Located in the desirable heart of the Via's, this single story home with a transitional interior in Sicilian Shores is a meticulously renovated Winter Park charmer. Nestled quietly on an almost 1/2 acre corner lot, this beautiful home is walking distance to the Winter Park Racquet Club and easy proximity to Park Avenue and Interlachen Country Club. Complete

  Lauren Richardson FANNIE HILLMAN & ASSOCIATES

  700 Pinetree Rd, Winter Park, FL 32789
• 

  /2

  $2,250,000 Sold Jun 25, 2025

  301 Rippling Ln, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,694 Sq Ft
  • Built 1958

  Last Sold Summary

  • 10% Below List Price
  • $609/SF
  • 98 Days On Market

  Current Estimated Value $2,225,862

  Last Listing Agent Cynthia Fernandez XCLUSIVE HOMES LLC

  301 Rippling Ln, Winter Park, FL 32789
• 

  

  /23

  Est $214,039 Not Listed For Sale

  700 Melrose Ave Unit K4, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft
  • Built 1964

  700 Melrose Ave Unit K4, Winter Park, FL 32789

  Last Sold Summary

  • 11% Below List Price
  • $329/SF
  • 27 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Isabella Martinez METROPOLITAN R.E SOLUTIONS INC
• 

  

  /78

  $1,895,000

  • 4 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  1841 Harland Park Dr, Winter Park, FL 32789

  Price reduction. Motivated seller! Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete

  Shanon Luiz SELECTIVE REALTY GROUP LLC

  1841 Harland Park Dr, Winter Park, FL 32789
• 

  /2

  $260,000 Sold Jan 30, 2026

  1250 S Denning Dr Unit 213, Winter Park, FL 32789

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

  Last Sold Summary

  • 5% Below List Price
  • $286/SF
  • 114 Days On Market

  Current Estimated Value $265,821

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1250 S Denning Dr Unit 213, Winter Park, FL 32789
• 

  

  /22

  Est $209,938 Not Listed For Sale

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft
  • Built 1964

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  Last Sold Summary

  • 12% Below List Price
  • $327/SF
  • 4 Days On Market

  Last Sold Price $239,000

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES
• 

  

  /70

  $419,990 Pending

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

  2249 Minnesota Ave, Winter Park, FL 32789

  Back on Market — Buyer’s financing fell through. This well-maintained Dubsdread District home is ready for its next owner! Previously under contract within 10 days, the property is back on the market due to a change in the buyer’s ability to secure finances — NO fault of the home. Featuring over 1,500 sq ft on a generous .22-acre lot across from the 5th tee at Dubsdread Golf Course, this updated

  Emily Nickley MARKET CONNECT REALTY LLC

  2249 Minnesota Ave, Winter Park, FL 32789
• 

  

  /61

  $610,000 Sold Feb 10, 2026

  1451 Cavendish Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,437 Sq Ft
  • Built 1971

  Last Sold Summary

  • 2% Below List Price
  • $424/SF

  Current Estimated Value $606,488

  Last Listing Agent Spencer Flory LoKation

  1451 Cavendish Rd, Winter Park, FL 32789
• 

  

  /18

  Est $174,955 Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft
  • Built 1967

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

  Last Sold Summary

  • 8% Below List Price
  • $289/SF
  • 3 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Victoria Epley PALMANO GROUP RE BROKERAGE LLC
• 

  

  /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
• 

  /2

  $1,000,000 Sold Nov 03, 2025

  215 Salvador Square, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft
  • Built 1973

  Last Sold Summary

  • 16% Below List Price
  • $390/SF
  • 44 Days On Market

  Current Estimated Value $1,046,498

  Last Listing Agent Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  215 Salvador Square, Winter Park, FL 32789
• 

  

  /30

  Est $688,485 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft
  • Built 1971

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

  Last Sold Summary

  • 3% Above List Price
  • $604/SF
  • 85 Days On Market

  Last Sold Price $670,000

  Last Listing Agent Victoria Epley PALMANO GROUP RE BROKERAGE LLC
• 

  

  /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
• 

  /2

  $675,000 Sold Nov 28, 2025

  2190 Temple Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,442 Sq Ft
  • Built 1956

  Last Sold Summary

  • 4% Below List Price
  • $468/SF
  • 108 Days On Market

  Current Estimated Value $689,885

  Last Listing Agent Sharon Mikol MAINFRAME REAL ESTATE

  2190 Temple Dr, Winter Park, FL 32789
• 

  

  /29

  Est $1,043,558 Not Listed For Sale

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

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft
  • Built 1971

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

  Last Sold Summary

  • 8% Above List Price
  • $557/SF
  • 79 Days On Market

  Last Sold Price $965,000

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
• 

  

  /26

  $189,500

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 222, Winter Park, FL 32789

  Lakefront access in Winter Park under $200K! One of the few condos at this price point offering direct access to Lake Killarney. This move-in ready 1-bedroom, 1-bath residence combines peaceful lakeside living with unbeatable proximity to Winter Park Village shopping, dining, and entertainment. The open-concept living and kitchen area features engineered wood flooring and abundant natural light,

  Christine Bouchard HOMESMART

  2500 Lee Rd Unit 222, Winter Park, FL 32789
• 

  /2

  $380,000 Sold Sep 26, 2025

  690 Osceola Ave Unit 209, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1969

  Last Sold Summary

  • 11% Below List Price
  • $331/SF
  • 34 Days On Market

  Current Estimated Value $375,232

  Last Listing Agent Mike Wang LOKATION

  690 Osceola Ave Unit 209, Winter Park, FL 32789
• 

  

  /9

  Est $143,691 Not Listed For Sale

  1695 Lee Rd Unit B103, Winter Park, FL 32789

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

  1695 Lee Rd Unit B103, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $176/SF
  • 16 Days On Market

  Last Sold Price $155,000

  Last Listing Agent Martha Grasty EXP REALTY LLC
• 

  

  /41

  $725,000 Pending

  • Land
  • 0.34 Acre
  • $2,132,353 per Acre

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789

  Under contract-accepting backup offers. Here it is! Almost impossible to find 2 adjacent 75x100 R-3 lots for a total of 75x200 or 15,000 sq/ft in top Winter Park location! Located at northwest corner of proposed Winter Park Commons project. The vacant lot to be simultaneously purchased with adjacent parcel (TAX ID 06-22-30-1168-02-022) fronting Webster with BONUS 4/2 Bungalow. Walk to WP Village,

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789
• 

  /2

  $315,000 Sold Apr 14, 2025

  690 Osceola Ave Unit 308, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1969

  Last Sold Summary

  • 15% Below List Price
  • $274/SF
  • 35 Days On Market

  Current Estimated Value $335,368

  Last Listing Agent Deborah Teixeira STRAWBERRY FIELDS FOREVER REALY LLC

  690 Osceola Ave Unit 308, Winter Park, FL 32789
• 

  /2

  Est $240,256 Not Listed For Sale

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

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

  1250 S Denning Dr Unit 105, Winter Park, FL 32789

  Last Sold Summary

  • 8% Below List Price
  • $286/SF
  • 15 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Joe Devlin DEVLIN INVESTORS & ASSOCIATES
• 

  

  /38

  $600,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  1399 Aloma Ave, Winter Park, FL 32789

  ***Price Adjustment *** Motivated Seller! Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on a private lot in the heart of Winter Park, moments from Rollins College, Park Avenue, and Winter Park Hospital. Just a short walk provides coveted access to the Winter Park Chain of Lakes, bring your paddle board or canoe. Step inside

  Cheryl Bennett FLORIDA HOMES REALTY & MORTGAGE

  1399 Aloma Ave, Winter Park, FL 32789

Showing Results 361 - 400, Page 10 of 18