Homes in ZIP Code 32789

• 

  

  

  /31

  $229,900

  $9K PRICE DROP Pending

  • 1 Bed
  • 1 Bath
  • 582 Sq Ft

  151 N Orlando Ave Unit 259, Winter Park, FL 32789

  Under contract-accepting backup offers. Virtually Staged. Welcome to Lake Killarney Living — where Winter Park charm meets everyday convenience.Discover this beautifully appointed condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, premier dining, boutique shopping, and the peaceful waters of Lake Killarney. This is

  Ryan Solberg MAXLIFE REALTY LLC

  151 N Orlando Ave Unit 259, Winter Park, FL 32789
• 

  

  /2

  $1,300,000

  Sold Jan 02, 2026

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft
  • Built 1962

  Last Sold Summary

  • 6% Below List Price
  • $563/SF
  • 333 Days On Market

  Current Estimated Value $1,245,007

  Last Listing Agent Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  

  /21

  Est $405,865

  Not Listed For Sale

  3508 Midiron Dr, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,036 Sq Ft
  • Built 1951

  3508 Midiron Dr, Winter Park, FL 32789

  Last Sold Summary

  • 12 Days On Market
• 

  

  

  /7

  $474,900

  $24K PRICE DROP

  • Land
  • 9,147 Sq Ft
  • $2,261,429 per Acre

  3601 Midiron Dr, Winter Park, FL 32789

  Ready to build your dream home or invest in one of Winter Park’s most desirable locations? This oversized, one-of-a-kind lot is ideally situated just across from Dubsdread Golf Course and only minutes from Park Avenue, Winter Park Village, dining, shopping, and entertainment. Enjoy convenient access to major roads while still being nestled in a highly sought-after neighborhood. Located within a

  Juliana Usquiano EMPIRE NETWORK REALTY

  3601 Midiron Dr, Winter Park, FL 32789
• 

  

  /2

  $1,050,000

  Sold Dec 05, 2025

  620 Virginia Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,577 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Above List Price
  • $666/SF
  • 0 Days On Market

  Current Estimated Value $1,064,806

  Last Listing Agent Jason Gilkey GILKEY REAL ESTATE

  620 Virginia Dr, Winter Park, FL 32789
• 

  /2

  Est $826,957

  Not Listed For Sale

  439 N Capen Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,861 Sq Ft
  • Built 2017

  439 N Capen Ave, Winter Park, FL 32789

  Last Sold Summary

  • 105 Days On Market
• 

  

  /49

  $3,290,000

  New Construction Pending

  • 4 Beds
  • 5.5 Baths
  • 3,788 Sq Ft

  1910 Glencoe Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. 2026 PARADE OF HOMES ENTRY! - Positioned on an expansive corner lot in the heart of Winter Park, this extraordinary new masterpiece is a true architectural statement, delivering a level of craftsmanship and detail that is simply unforgettable. Framed by a massive front yard and a canopy of mature trees, the bold modern façade creates an immediate sense of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  1910 Glencoe Rd, Winter Park, FL 32789
• 

  /2

  $4,500,000

  Sold Apr 30, 2026

  887 Georgia Ave, Winter Park, FL 32789

  • 6 Beds
  • 5.5 Baths
  • 5,759 Sq Ft
  • Built 1924

  Last Sold Summary

  • 31% Below List Price
  • $781/SF
  • 222 Days On Market

  Current Estimated Value $4,590,054

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  887 Georgia Ave, Winter Park, FL 32789
• 

  

  /36

  Est $1,282,047

  Not Listed For Sale

  1572 Sunset Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,626 Sq Ft
  • Built 2022

  1572 Sunset Dr, Winter Park, FL 32789

  Last Sold Summary

  • 143 Days On Market
• 

  

  /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. This is your final opportunity to build a custom home in one of Winter Park’s most sought-after pockets. Set on a 6,748 sq ft lot, this brand-new 4-bedroom, 3.5-bath residence offers 2,662 sq ft of thoughtfully designed living space, blending clean modern architecture with the comfort and functionality today’s buyers expect. Crisp lines, open-concept living, and

  Vinny Lay COMPASS FLORIDA LLC

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

  /2

  $465,000

  Sold Oct 21, 2025

  130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Below List Price
  • $303/SF
  • 75 Days On Market

  Current Estimated Value $458,962

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  130 Killarney Bay Ct Unit 5-3, Winter Park, FL 32789
• 

  

  /60

  Est $1,587,754

  Not Listed For Sale

  1318 Morton Rd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,579 Sq Ft
  • Built 2022

  1318 Morton Rd, Winter Park, FL 32789

  Last Sold Summary

  • 18 Days On Market
• 

  /2

  $1,450,000

  • Land
  • 8,276 Sq Ft
  • $7,631,579 per Acre

  120 Broadview Ave, Winter Park, FL 32789

  STUNNING SUNSET VIEWS OF LAKE KILLARNEY FROM THIS CORNER LOT SITUATED ON A SERENE PRIVATE BRICK DEAD END STREET WITH 65 FEET OF LAKE FRONTAGE. BUILD YOUR LAKEFRONT DREAM HOME AND ADD A BOAT DOCK FOR THIS PRIVATE LAKE EXPERIENCE. THIS IS A RARE FIND IN WINTER PARK. SELLER IS ALSO OFFERING TO EXTEND CURRENT LOT TO INCLUDE AN ADDITIONAL 30 X 65 FROM BACK LOT LINE. THIS ADDED LAND BRINGS THE LOT SIZE

  David Murray PROMAX PROPERTY SOLUTIONS

  120 Broadview Ave, Winter Park, FL 32789
• 

  /2

  $1,555,000

  Sold Sep 12, 2025

  817 Antonette Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,971 Sq Ft
  • Built 1990

  Last Sold Summary

  • 22% Below List Price
  • $392/SF
  • 146 Days On Market

  Current Estimated Value $1,622,234

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

  817 Antonette Ave, Winter Park, FL 32789
• 

  

  /61

  Est $2,187,459

  Not Listed For Sale

  1461 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,436 Sq Ft
  • Built 2023

  1461 Palm Ave, Winter Park, FL 32789

  Last Sold Summary

  • 128 Days On Market
• 

  

  /45

  $3,390,000

  New Construction Open Sat 12PM - 2PM $505K PRICE DROP

  • 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 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. Inside,

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  1751 Glencoe Rd, Winter Park, FL 32789
• 

  /2

  $367,500

  Sold Nov 17, 2025

  1975 Staunton Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1949

  Last Sold Summary

  • 15% Below List Price
  • $306/SF
  • 225 Days On Market

  Current Estimated Value $364,658

  Last Listing Agent Marion McGrath ABSOLUTE REALTY GROUP, LLC

  1975 Staunton Ave, Winter Park, FL 32789
• 

  

  /22

  Est $1,320,459

  Not Listed For Sale

  1531 Sunset Dr, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,619 Sq Ft
  • Built 1992

  1531 Sunset Dr, Winter Park, FL 32789

  Last Sold Summary

  • 1 Day On Market
• 

  

  /34

  $1,599,000

  $51K PRICE DROP Pending

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

  1340 Place Picardy, Winter Park, FL 32789

  Under contract-accepting backup offers. 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

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  1340 Place Picardy, Winter Park, FL 32789
• 

  /2

  $3,278,530

  Sold May 20, 2026

  700 Pinetree Rd, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,897 Sq Ft
  • Built 1955

  Last Sold Summary

  • $841/SF
  • 1 Day On Market

  Current Estimated Value $3,021,130

  Last Listing Agent Lauren Richardson FANNIE HILLMAN & ASSOCIATES

  700 Pinetree Rd, Winter Park, FL 32789
• 

  

  /52

  Est $1,519,715

  Not Listed For Sale

  2301 Chantilly Ave, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 3,350 Sq Ft
  • Built 1998

  2301 Chantilly Ave, Winter Park, FL 32789

  Last Sold Summary

  • 45 Days On Market
• 

  

  /3

  $649,900

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,837 Sq Ft

  1003 Lake Bell Dr, Winter Park, FL 32789

  (Professional photos and floor plan coming week of July 6) Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell for under $650,000. Tucked away in a peaceful, private setting, yet just minutes from Winter Park’s famed Park Ave, Winter Park Village, College Park and Downtown Orlando

  Bryan Douglas KELLER WILLIAMS REALTY AT THE PARKS

  1003 Lake Bell Dr, Winter Park, FL 32789
• 

  /2

  $1,250,000

  Sold Aug 29, 2025

  1621 Hillcrest Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,755 Sq Ft
  • Built 1947

  Last Sold Summary

  • $454/SF
  • 0 Days On Market

  Current Estimated Value $1,276,414

  Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

  1621 Hillcrest Ave, Winter Park, FL 32789
• 

  /2

  Est $938,248

  Not Listed For Sale

  2421 Mandan Trail, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,310 Sq Ft
  • Built 1968

  2421 Mandan Trail, Winter Park, FL 32789

  Last Sold Summary

  • 71 Days On Market
• 

  

  /77

  $2,699,000

  $151K PRICE DROP Pending

  • 4 Beds
  • 6 Baths
  • 4,356 Sq Ft

  1529 Holts Grove Cir, Winter Park, FL 32789

  Under contract-accepting backup offers. Tucked within the prestigious enclave of Windsong Lakeside in Winter Park, this extraordinary estate is a masterclass in refined living—where thoughtful design, cutting-edge technology, and timeless elegance converge. From the moment you arrive, the circular drive and stately presence set a tone of quiet grandeur. Step inside, and the home unfolds with an

  Kristin Vogt PLLC KGV REALTY GROUP

  1529 Holts Grove Cir, Winter Park, FL 32789
• 

  /2

  $6,300,000

  Sold Nov 04, 2025

  1308 Green Cove Rd, Winter Park, FL 32789

  • 4 Beds
  • 5.5 Baths
  • 6,981 Sq Ft
  • Built 1990

  Last Sold Summary

  • $902/SF
  • 0 Days On Market

  Current Estimated Value $6,289,586

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  1308 Green Cove Rd, Winter Park, FL 32789
• 

  

  /59

  Est $1,213,449

  Not Listed For Sale

  1879 Lake Spier Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,350 Sq Ft
  • Built 1957

  1879 Lake Spier Dr, Winter Park, FL 32789

  Last Sold Summary

  • 20 Days On Market
• 

  

  /38

  $3,235,000

  New Construction $260K PRICE DROP

  • 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

  $1,635,000

  Sold May 11, 2026

  1841 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,470 Sq Ft
  • Built 2014

  Last Sold Summary

  • 18% Below List Price
  • $471/SF
  • 103 Days On Market

  Current Estimated Value $1,857,772

  Last Listing Agent Shanon Luiz SELECTIVE REALTY GROUP LLC

  1841 Harland Park Dr, Winter Park, FL 32789
• 

  

  /46

  Est $543,082

  Not Listed For Sale

  1321 Harmon Ave, Winter Park, FL 32789

  • 4 Beds
  • 1,548 Sq Ft
  • Built 1966

  1321 Harmon Ave, Winter Park, FL 32789

  Last Sold Summary

  • 10 Days On Market
• 

  

  /67

  $1,750,000

  • 4 Beds
  • 3.5 Baths
  • 3,174 Sq Ft

  1420 Magnolia Ave, Winter Park, FL 32789

  On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch

  Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

  1420 Magnolia Ave, Winter Park, FL 32789
• 

  /2

  $4,430,000

  Sold Oct 09, 2025

  2161 Sharon Rd, Winter Park, FL 32789

  • 5 Beds
  • 6.5 Baths
  • 6,338 Sq Ft
  • Built 2023

  Last Sold Summary

  • 11% Below List Price
  • $699/SF
  • 247 Days On Market

  Current Estimated Value $4,250,043

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  2161 Sharon Rd, Winter Park, FL 32789
• 

  /2

  Est $700,694

  Not Listed For Sale

  1331 Suffolk Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,508 Sq Ft
  • Built 1955

  1331 Suffolk Rd, Winter Park, FL 32789

  Last Sold Summary

  • 3 Days On Market
• 

  

  /27

  $98,000

  $17K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft

  1695 Lee Rd Unit B210, Winter Park, FL 32789

  This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

  giuseppina moriconi GM SUNSHINE REALTY LLC

  1695 Lee Rd Unit B210, Winter Park, FL 32789
• 

  /2

  $519,180

  Sold Jul 08, 2025

  2518 Sweetwater Trail, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,205 Sq Ft
  • Built 1965

  Last Sold Summary

  • 21% Below List Price
  • $235/SF
  • 201 Days On Market

  Current Estimated Value $593,285

  Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  2518 Sweetwater Trail, Winter Park, FL 32789
• 

  

  /20

  Est $652,822

  Not Listed For Sale

  1523 Berkshire Ave, Winter Park, FL 32789

  • 3 Beds
  • 1.5 Baths
  • 1,218 Sq Ft
  • Built 1953

  1523 Berkshire Ave, Winter Park, FL 32789

  Last Sold Summary

  • 5 Days On Market
• 

  

  /57

  $1,299,900

  Open Sun 2PM - 4PM $150K PRICE DROP

  • 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

  $1,565,000

  Sold Sep 24, 2025

  1450 Glencoe Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,662 Sq Ft
  • Built 1952

  Last Sold Summary

  • 1% Below List Price
  • $588/SF
  • 42 Days On Market

  Current Estimated Value $1,598,405

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1450 Glencoe Rd, Winter Park, FL 32789
• 

  

  /4

  Est $457,956

  Not Listed For Sale

  2040 Jewell Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,200 Sq Ft
  • Built 1940

  2040 Jewell Ave, Winter Park, FL 32789

  Last Sold Summary

  • 46 Days On Market
• 

  

  /23

  $2,829,000

  New Construction

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

  609 S Phelps Ave, Winter Park, FL 32789

  Under Construction. Under Construction. A timeless expression of modern luxury, this exceptional new residence by LUIH Luxury Homes brings together thoughtful architecture, designer finishes, and refined craftsmanship in one of Winter Park’s most desirable neighborhoods. Situated on an oversized homesite along a quiet, tree-lined street, the home offers approximately 4,018 square feet of

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  609 S Phelps Ave, Winter Park, FL 32789

Showing Results 641 - 680, Page 17 of 18