Homes in ZIP Code 32789

• 

  

  /2

  Est $993,977 Not Listed For Sale

  627 N Interlachen Ave Unit B, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,610 Sq Ft
  • Built 1981

  627 N Interlachen Ave Unit B, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $624/SF
  • 164 Days On Market

  • Last Sold Price $1,005,000
  • Feb 05, 2025

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

  

  

  /49

  $3,290,000 New Construction

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

  1910 Glencoe Rd, Winter Park, FL 32789

  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 arrival and sets the tone for what lies

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  1910 Glencoe Rd, 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 $436,778

  Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

  105 Conrad Ct, Winter Park, FL 32789
• 

  

  

  /18

  Est $336,550 Not Listed For Sale

  420 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1986

  420 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  Last Sold Summary

  • $291/SF
  • 0 Days On Market

  • Last Sold Price $338,000
  • Mar 28, 2024

  Last Listing Agent Corey Mahon CENTRO REAL ESTATE GROUP, LLC
• 

  

  

  /32

  $2,100,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,900 Sq Ft

  311 E Morse Blvd Unit 2-5, Winter Park, FL 32789

  Under contract-accepting backup offers. Enjoy the Winter Park lifestyle in this spacious 2-bedroom, 2-bath lakefront condo offering 1,900 square feet in the heart of downtown Winter Park. Enjoy serene lake views from the 120 sq ft screened porch—perfect for morning coffee or evening wine. The light-filled living area features soaring 8 ft 10 in ceilings, creating an open, airy atmosphere. A cozy

  Megan Cross FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 2-5, Winter Park, FL 32789
• 

  /2

  $292,000 Sold May 16, 2025

  712 Baffie Ave, Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,304 Sq Ft
  • Built 1925

  Last Sold Summary

  • 10% Below List Price
  • $224/SF
  • 7 Days On Market

  Current Estimated Value $318,985

  Last Listing Agent Bobby Livera BALDWIN PARK REALTY LLC

  712 Baffie Ave, Winter Park, FL 32789
• 

  /2

  Est $343,716 Not Listed For Sale

  647 Huntington Ave Unit 8, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,204 Sq Ft
  • Built 1981

  647 Huntington Ave Unit 8, Winter Park, FL 32789

  Last Sold Summary

  • 4% Above List Price
  • $274/SF
  • 54 Days On Market

  • Last Sold Price $330,000
  • Dec 20, 2024

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

  

  /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

  $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 $1,255,035

  Last Listing Agent Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
• 

  /2

  Est $839,362 Not Listed For Sale

  1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Built 2007

  1248 S Pennsylvania Ave Unit 7, Winter Park, FL 32789

  Last Sold Summary

  • 8% Below List Price
  • $465/SF
  • 16 Days On Market

  • Last Sold Price $910,000
  • Aug 30, 2024

  Last Listing Agent Trevor Brown FANNIE HILLMAN & ASSOCIATES
• 

  

  /45

  $3,490,000 New Construction

  • 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

  $575,000 Sold May 27, 2025

  1230 N Denning Dr, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft
  • Built 1952

  Last Sold Summary

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

  Current Estimated Value $576,987

  Last Listing Agent Ed Klein FANNIE HILLMAN & ASSOCIATES

  1230 N Denning Dr, Winter Park, FL 32789
• 

  

  /90

  Est $850,326 Not Listed For Sale

  1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Built 2007

  1264 S Pennsylvania Ave Unit 10, Winter Park, FL 32789

  Last Sold Summary

  • 8% Below List Price
  • $474/SF
  • 98 Days On Market

  • Last Sold Price $927,000
  • Aug 21, 2024

  Last Listing Agent David Gallup RE/MAX
• 

  

  /34

  $1,599,000 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

  $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 $1,065,336

  Last Listing Agent Jason Gilkey GILKEY REAL ESTATE

  620 Virginia Dr, Winter Park, FL 32789
• 

  

  /37

  Est $299,704 Not Listed For Sale

  1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 830 Sq Ft
  • Built 1983

  1302 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • 9% Below List Price
  • $398/SF
  • 4 Days On Market

  • Last Sold Price $330,000
  • Apr 26, 2024

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK
• 

  

  /84

  $2,795,000

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

  1529 Holts Grove Cir, Winter Park, FL 32789

  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 effortless sense of scale, defined by

  Kristin Vogt PLLC KGV REALTY GROUP

  1529 Holts Grove Cir, 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 $4,650,376

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  887 Georgia Ave, Winter Park, FL 32789
• 

  /2

  Est $631,040 Not Listed For Sale

  1086 Azalea Ln, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft
  • Built 1983

  1086 Azalea Ln, Winter Park, FL 32789

  Last Sold Summary

  • 4% Below List Price
  • $369/SF
  • 17 Days On Market

  • Last Sold Price $658,125
  • Dec 11, 2024

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
• 

  

  /36

  $3,135,000 New Construction

  • 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

  $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 $457,727

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

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

  /2

  Not Listed For Sale

  213 E Canton Ave Unit 213, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1971

  213 E Canton Ave Unit 213, Winter Park, FL 32789

  Last Sold Summary

  • $457/SF
  • 97 Days On Market

  • Last Sold Price $475,000
  • Feb 10, 2025

  Last Listing Agent Becki Douglas MAINFRAME REAL ESTATE
• 

  

  /67

  $3,978,900 Pending

  • 4 Beds
  • 4.5 Baths
  • 4,353 Sq Ft

  1117 Kenwood Ave, Winter Park, FL 32789

  Experience the art of luxury living just steps from the boutiques, cafés & celebrated dining of Park Avenue, Winter Park Village, Rollins College & the iconic Winter Park Art Festival. This beautifully crafted custom one-story pool home built in 2024 blends elegant design with an effortless, modern lifestyle. THIS HOME RECEIVED THE 2025 ARDA GRAND AWARD FOR CUSTOM HOME (built).A thoughtful

  Domenique Lombardo ROYALTY R E BOUTIQUE INC

  1117 Kenwood 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 $1,551,223

  Last Listing Agent Mary Colton FANNIE HILLMAN & ASSOCIATES

  817 Antonette Ave, Winter Park, FL 32789
• 

  

  /30

  Est $1,685,095 Not Listed For Sale

  102 S Virginia Ave Unit 110, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,778 Sq Ft
  • Built 2008

  102 S Virginia Ave Unit 110, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $421/SF
  • 70 Days On Market

  • Last Sold Price $1,590,000
  • Aug 14, 2023

  Last Listing Agent Anthony Consalvo FLORIDA ONE REAL ESTATE LLC
• 

  

  /27

  $109,000

  • 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

  $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 $363,196

  Last Listing Agent Marion McGrath ABSOLUTE REALTY GROUP, LLC

  1975 Staunton Ave, Winter Park, FL 32789
• 

  /2

  Est $434,411 Not Listed For Sale

  1216 Park Green Place, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,020 Sq Ft
  • Built 1982

  1216 Park Green Place, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $220/SF
  • 207 Days On Market

  • Last Sold Price $445,000
  • Dec 27, 2024

  Last Listing Agent Dustin Hope BUY THE SEA REALTY LLC
• 

  

  /51

  $1,399,000

  • 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

  $1,250,000 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 $1,247,597

  Last Listing Agent Julie Glass KEYSEEKERS REAL ESTATE

  1621 Hillcrest Ave, Winter Park, FL 32789
• 

  

  /68

  Est $1,024,350 Not Listed For Sale

  645 N Interlachen Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,766 Sq Ft
  • Built 1981

  645 N Interlachen Ave, Winter Park, FL 32789

  Last Sold Summary

  • 12% Below List Price
  • $661/SF
  • 107 Days On Market

  • Last Sold Price $1,168,000
  • Jun 18, 2024

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
• 

  

  /40

  $359,000

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-5, Winter Park, FL 32789

  Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park! This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and Structural Integrity Reserve Study

  Jeff Dodds CHARLES RUTENBERG REALTY ORLANDO

  311 E Morse Blvd Unit 7-5, 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 $6,276,934

  Last Listing Agent Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  1308 Green Cove Rd, Winter Park, FL 32789
• 

  

  /47

  Est $2,197,110 Not Listed For Sale

  200 S Interlachen Ave Unit 450, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,110 Sq Ft
  • Built 2001

  200 S Interlachen Ave Unit 450, Winter Park, FL 32789

  Last Sold Summary

  • $707/SF
  • 85 Days On Market

  • Last Sold Price $2,200,000
  • Feb 27, 2024

  Last Listing Agent Lisa Shear FANNIE HILLMAN & ASSOCIATES
• 

  

  /19

  $2,829,000 New Construction

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

  609 S Phelps Ave, Winter Park, FL 32789

  Under Construction. Introducing the newest showpiece from LUIH Luxury Homes, perfectly positioned in the heart of Winter Park. Set on an oversized homesite along a quiet, tree-lined street, this residence immediately captivates with its expansive front lawn and timeless architectural presence. Inside, the home unfolds with a thoughtfully designed and highly functional floor plan that balances

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  609 S Phelps Ave, Winter Park, FL 32789
• 

  /2

  $1,340,000 Sold May 28, 2025

  571 Lakefront Blvd, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 5,500 Sq Ft
  • Built 1967

  Last Sold Summary

  • 68% Below List Price
  • $244/SF
  • 293 Days On Market

  Current Estimated Value $1,342,571

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

  571 Lakefront Blvd, Winter Park, FL 32789
• 

  

  /38

  Est $826,175 Not Listed For Sale

  1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Built 2007

  1272 S Pennsylvania Ave Unit 11, Winter Park, FL 32789

  Last Sold Summary

  • 12% Below List Price
  • $478/SF
  • 60 Days On Market

  • Last Sold Price $935,000
  • Mar 11, 2024

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

  

  /52

  $224,999

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool &

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
• 

  /2

  $315,000 Sold Mar 27, 2026

  2249 Minnesota Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1955

  Last Sold Summary

  • 28% Below List Price
  • $205/SF
  • 42 Days On Market

  Current Estimated Value $415,430

  Last Listing Agent Emily Nickley MARKET CONNECT REALTY LLC

  2249 Minnesota Ave, Winter Park, FL 32789
• 

  

  /66

  Est $1,579,360 Not Listed For Sale

  101 S New York Ave Unit 301, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,176 Sq Ft
  • Built 2008

  101 S New York Ave Unit 301, Winter Park, FL 32789

  Last Sold Summary

  • 17% Above List Price
  • $425/SF
  • 2 Days On Market

  • Last Sold Price $1,350,000
  • Nov 16, 2023

  Last Listing Agent Edward Johnston COLDWELL BANKER REALTY

Showing Results 601 - 640, Page 16 of 18