Homes in ZIP Code 32789

• 

  

  /2

  Est $826,492

  Not Listed For Sale

  1820 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,252 Sq Ft
  • Built 2018

  1820 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 81 Days On Market

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
• 

  

  

  /9

  $349,000

  • 2 Beds
  • 1 Bath
  • 749 Sq Ft

  811 Overspin Dr, Winter Park, FL 32789

  Charming Winter Park Opportunity in Desirable Dubsdread Heights! NEW ROOF NEW A/c new kitchen ,bath, floor Welcome to 811 Overspin Drive, a cozy and character-filled 2-bedroom, 1-bath single-family home nestled in the heart of Winter Park. This property offers approximately 700+ square feet of living space on a generously sized lot, providing endless potential for homeowners, investors, or those

  Rickey Singh RICK SINGH REAL ESTATE

  811 Overspin Dr, Winter Park, FL 32789
• 

  

  /2

  $2,200,000

  Sold Jun 16, 2026

  2550 Venetian Way, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 5,051 Sq Ft
  • Built 2008

  Last Sold Summary

  • 10% Below List Price
  • $436/SF
  • 63 Days On Market

  Current Estimated Value $2,255,601

  Last Listing Agent Felicia Donateli PALM PROPERTIES OF CF, INC.

  2550 Venetian Way, Winter Park, FL 32789
• 

  

  

  /77

  Est $1,174,595

  Not Listed For Sale

  690 Osceola Ave Unit 504, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,079 Sq Ft
  • Built 1969

  690 Osceola Ave Unit 504, Winter Park, FL 32789

  Last Sold Summary

  • 74 Days On Market

  Last Listing Agent Dela Armstrong C BRENNER INC
• 

  

  

  /10

  $5,500,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,775 Sq Ft

  313 Sylvan Dr, Winter Park, FL 32789

  Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportunity to own a thoughtfully curated custom home by renowned builder Floridian Custom Homes, brought to life in collaboration with Winter Park Design, Brianna Michelle Interior Design and Signature Landscape. Offering 4,775 heated

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  313 Sylvan Dr, Winter Park, FL 32789
• 

  /2

  $2,875,000

  Sold Jul 15, 2026

  1724 Pine Ave, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 4,425 Sq Ft
  • Built 2012

  Last Sold Summary

  • 7% Below List Price
  • $650/SF
  • 6 Days On Market

  Current Estimated Value $2,913,809

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

  1724 Pine Ave, Winter Park, FL 32789
• 

  

  /47

  Est $1,404,161

  Not Listed For Sale

  518 W Swoope Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,734 Sq Ft
  • Built 2021

  518 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • 119 Days On Market

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK
• 

  

  /49

  $775,000

  • 4 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  1562 Arbor Park Dr, Winter Park, FL 32789

  Welcome to 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. This move-in-ready home combines elevated finishes, abundant natural light, a flexible split-bedroom floor plan, and an exceptional location near the shopping, dining, and cultural attractions that make Winter Park one of Central

  Abby Greenberg COMPASS FLORIDA LLC

  1562 Arbor Park 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

  Current Estimated Value $2,599,390

  Last Listing Agent Julie Bettosini STOCKWORTH REALTY GROUP

  1341 Place Picardy, Winter Park, FL 32789
• 

  

  /32

  Est $2,581,419

  Not Listed For Sale

  170 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,288 Sq Ft
  • Built 2023

  170 S Phelps Ave, Winter Park, FL 32789

  Last Sold Summary

  • 236 Days On Market

  Last Listing Agent Monica Tipirneni FOLIO REALTY LLC
• 

  

  /36

  $849,000

  • 3 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  437 N Capen Ave, Winter Park, FL 32789

  Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’

  Brandon Geers COMPASS FLORIDA LLC

  437 N Capen Ave, Winter Park, FL 32789
• 

  /2

  $1,300,000

  Sold Jul 24, 2026

  321 Sylvan Blvd, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,821 Sq Ft
  • Built 1940

  Last Sold Summary

  • 7% Below List Price
  • $461/SF
  • 0 Days On Market

  Current Estimated Value $1,381,639

  Last Listing Agent Mel Bernstein PREMIER SOTHEBYS INT'L REALTY

  321 Sylvan Blvd, Winter Park, FL 32789
• 

  

  /41

  Est $830,046

  Not Listed For Sale

  440 Shoreview Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,205 Sq Ft
  • Built 2014

  440 Shoreview Ave, Winter Park, FL 32789

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Linda Jokbengboon COMPASS FLORIDA LLC
• 

  

  /16

  $799,000

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

  1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789

  In the heart of Winter Park’s coveted Virginia Heights neighborhood, just moments from the boutiques, dining, and charm of Park Avenue and the green spaces of Seven Oaks Park, this exceptional Mediterranean-inspired end-unit condominium offers an unparalleled blend of elegance, comfort and accessible convenience. Encompassing nearly 2,000 square feet, the residence features three bedrooms,

  Nancy Merriam PREMIER SOTHEBY'S INTL. REALTY

  1278 S Pennsylvania Ave Unit 13, Winter Park, FL 32789
• 

  /2

  $415,000

  Sold Mar 02, 2026

  875 W Lyman Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 760 Sq Ft
  • Built 1925

  Last Sold Summary

  • 13% Below List Price
  • $546/SF
  • 60 Days On Market

  Current Estimated Value $430,677

  Last Listing Agent Joey Bruno CHARLES RUTENBERG REALTY ORLANDO

  875 W Lyman Ave, Winter Park, FL 32789
• 

  /2

  Est $1,397,030

  Not Listed For Sale

  1009 S Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft
  • Built 2016

  1009 S Pennsylvania Ave, Winter Park, FL 32789

  Last Sold Summary

  • 5 Days On Market

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

  

  /29

  $499,000

  $81K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1807 Hammerlin Ave Unit G, Winter Park, FL 32789

  Virtually Staged. **Price Improvement**Welcome home to this beautifully updated two-story end-unit, ideally located just steps from Michelin-star dining, local boutiques, and the vibrant East End Market. On weekends, enjoy leisurely strolls to the area’s popular farmers markets and neighborhood events.Situated in the heart of Winter Park, this residence offers the perfect blend of

  Courtney Dietch ALL REAL ESTATE & INVESTMENTS

  1807 Hammerlin Ave Unit G, Winter Park, FL 32789
• 

  /2

  $1,850,000

  Sold Dec 15, 2025

  419 W Morse Blvd, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,027 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $611/SF
  • 0 Days On Market

  Current Estimated Value $1,866,195

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

  419 W Morse Blvd, Winter Park, FL 32789
• 

  /2

  Est $1,943,028

  Not Listed For Sale

  643 Pansy Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,228 Sq Ft
  • Built 2015

  643 Pansy Ave, Winter Park, FL 32789

  Last Sold Summary

  • 10 Days On Market

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

  

  /50

  $1,380,000

  $95K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,170 Sq Ft

  1751 Goodrich Ave, Winter Park, FL 32789

  Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

  Stephanie Baldner EXP REALTY LLC

  1751 Goodrich Ave, Winter Park, FL 32789
• 

  /2

  $3,800,000

  Sold Feb 24, 2026

  637 N Park Ave, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 4,237 Sq Ft
  • Built 2019

  Last Sold Summary

  • 2% Below List Price
  • $897/SF
  • 24 Days On Market

  Current Estimated Value $3,842,825

  Last Listing Agent Whitney Johnson COLDWELL BANKER REALTY

  637 N Park Ave, Winter Park, FL 32789
• 

  /2

  Est $1,567,093

  Not Listed For Sale

  1571 Sunset Dr, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 2,700 Sq Ft
  • Built 2015

  1571 Sunset Dr, Winter Park, FL 32789

  Last Sold Summary

  • 79 Days On Market

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

  

  /49

  $1,800,000

  • 5 Beds
  • 4.5 Baths
  • 4,029 Sq Ft

  281 Brewer Ave, Winter Park, FL 32789

  Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers market and so much more. A beautiful contemporary style home with modern interior finishes. Featuring an open floor plan, 5 bedrooms, 4.5 baths, a loft/flex space, media room, 2 study areas, front porch, back patio, lanai and so

  John Henthorn HENTHORN REAL ESTATE

  281 Brewer Ave, Winter Park, FL 32789
• 

  /2

  $1,655,000

  Sold May 14, 2026

  629 Country Club Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft
  • Built 2026

  Last Sold Summary

  • 2% Below List Price
  • $546/SF
  • 58 Days On Market

  Current Estimated Value $1,683,667

  Last Listing Agent Randy Lazarus CLASSIC HOMES

  629 Country Club Dr, Winter Park, FL 32789
• 

  /2

  Est $2,277,317

  Not Listed For Sale

  1770 Oakhurst Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,640 Sq Ft
  • Built 2019

  1770 Oakhurst Ave, Winter Park, FL 32789

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC
• 

  

  /43

  $1,750,000

  Open Sat 1PM - 3PM $115K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2343 Versailles Ave, Winter Park, FL 32789

  This modern and sleek Winter Park residence, with over $130K of improvements, is tucked along a quiet dead-end street, offering a functional, open floorplan in an exceptional location. Recent upgrades make this home feel wonderfully fresh and new, including a Mosquito Nix misting system, Culligan whole-home water filtration system, fresh paint throughout the entire home, a beautifully remodeled

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  2343 Versailles Ave, Winter Park, FL 32789
• 

  /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 $1,380,085

  Last Listing Agent Laura Ascenso CREEGAN GROUP

  1600 Barcelona Way, Winter Park, FL 32789
• 

  /2

  Est $1,206,753

  Not Listed For Sale

  1571 Oneco Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,510 Sq Ft
  • Built 2009

  1571 Oneco Ave, Winter Park, FL 32789

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC
• 

  

  /9

  $3,195,000

  New Construction Coming Soon

  • 5 Beds
  • 5.5 Baths
  • 4,139 Sq Ft

  2119 Howard Dr, Winter Park, FL 32789

  Pre-Construction. To be built. A striking new custom residence by FG Schaub Custom Homes, located at 2119 Howard Drive in Winter Park. This exceptional 5-bedroom, 5.5-bath home offers 4,139 square feet of beautifully appointed living space, thoughtfully designed for elevated everyday living and effortless entertaining.The dramatic two-story stone entry creates a memorable first impression,

  Laura Earl CORCORAN PREMIER REALTY

  2119 Howard Dr, Winter Park, FL 32789
• 

  /2

  $1,300,000

  Sold Sep 02, 2026

  1778 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft
  • Built 2023

  Last Sold Summary

  • 3% Below List Price
  • $547/SF
  • 4 Days On Market

  Current Estimated Value $1,290,556

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  1778 Mondrian Cir, Winter Park, FL 32789
• 

  /2

  Est $536,389

  Not Listed For Sale

  1392 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2008

  1392 Indiana Ave, Winter Park, FL 32789

  Last Sold Summary

  • 123 Days On Market

  Last Listing Agent Cody Hancock COLDWELL BANKER REALTY
• 

  

  /27

  $1,249,900

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,936 Sq Ft

  Winter Park, FL 32789

  Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  Winter Park, FL 32789
• 

  /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 $125,984

  Last Listing Agent Justin Adams EXP REALTY LLC

  1695 Lee Rd Unit C206, Winter Park, FL 32789
• 

  

  /59

  Est $2,430,651

  Not Listed For Sale

  1411 Elizabeth Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,870 Sq Ft
  • Built 2008

  1411 Elizabeth Dr, Winter Park, FL 32789

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
• 

  

  /29

  $2,625,000

  $70K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,048 Sq Ft

  413 W Morse Blvd, Winter Park, FL 32789

  LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound

  A.V. Blalock COLDWELL BANKER REALTY

  413 W Morse Blvd, Winter Park, FL 32789
• 

  /2

  $1,500,000

  Sold Mar 16, 2026

  1871 Taylor Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,401 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $441/SF
  • 2 Days On Market

  Current Estimated Value $1,577,821

  Last Listing Agent Laura Earl CORCORAN PREMIER REALTY

  1871 Taylor Ave, Winter Park, FL 32789
• 

  /2

  Est $461,538

  Not Listed For Sale

  2112 Staunton Ave, Winter Park, FL 32789

  • 3 Beds
  • 1 Bath
  • 1,438 Sq Ft
  • Built 1954

  2112 Staunton Ave, Winter Park, FL 32789

  Last Sold Summary

  • 12 Days On Market

  Last Listing Agent Stacey Payne PREFERRED REAL ESTATE BROKERS
• 

  

  /34

  $745,000

  • 2 Beds
  • 3 Baths
  • 1,440 Sq Ft

  408 Holt Ave, Winter Park, FL 32789

  Rare investment opportunity in the heart of Winter Park/Rollins College area. This turnkey, fully renovated triplex is located within one of Winter Park’s highest-demand rental corridors, just steps from Rollins College, Park Avenue, and Lake Virginia.The property features three separate 1-bedroom, 1-bath units, each with its own private outdoor patio area, positioned on a charming brick

  Brian Opre THE REAL ESTATE PRINCIPLE, INC

  408 Holt Ave, Winter Park, FL 32789
• 

  /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
• 

  /2

  Est $1,937,691

  Not Listed For Sale

  331 E Reading Way, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,361 Sq Ft
  • Built 2007

  331 E Reading Way, Winter Park, FL 32789

  Last Sold Summary

  • 110 Days On Market

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

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