Homes in ZIP Code 32789

• 

  

  

  /71

  $2,150,000 Pending

  • 5 Beds
  • 4 Baths
  • 3,909 Sq Ft

  141 Oakwood Way, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area. This modern Mediterranean-inspired residence seamlessly blends timeless elegance with contemporary luxury, offering an exceptional living experience with high-end finishes, thoughtfully designed spaces, and unmatched attention to detail.

  

  Nicole Rader

  MAINFRAME REAL ESTATE

  (321) 463-7756

  141 Oakwood Way, Winter Park, FL 32789
• 

  

  

  /43

  $1,853 - $3,252 per month

  Bainbridge Winter Park

  1 - 3 Beds

  1400 Morgan Stanley Ave, Winter Park, FL 32789

  Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

  1400 Morgan Stanley Ave, Winter Park, FL 32789
• 

  

  /2

  $1,079,000 Sold Sep 05, 2025

  • 2,649 Sq Ft
  • $407/SF
  • 2 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2008

  100 S Virginia Ave Unit 319, Winter Park, FL 32789

  Experience the best of Winter Park living in this distinguished three-bedroom, three-bathroom condominium, located in the secure and sought-after Douglas Grand development—just one block from vibrant Park Avenue. Spanning an impressive 2,649 sq ft on a single level, this third-floor residence blends timeless architectural charm, quality construction, and everyday function. Step inside to an

  Padgett McCormick KELLY PRICE & COMPANY LLC

  100 S Virginia Ave Unit 319, Winter Park, FL 32789
• 

  

  

  /42

  Est $1,612,922 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft

  1805 Harland Park Dr, Winter Park, FL 32789

  1805 Harland Park Dr, Winter Park, FL 32789
• 

  

  /2

  $475,000 Pending

  • Land
  • 0.16 Acre
  • $2,968,750 per Acre

  1414 Bessmor Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. ?? Land for Sale – Build Your Dream Home in Winter Park! Just minutes from Park Avenue!Discover the perfect opportunity to build your custom home in one of Central Florida’s most desirable neighborhoods! This prime homesite is nestled among newly built luxury residences and offers the ideal canvas for your future home.The owner has already completed

  

  Miranda Azer

  PARKVIEW REAL ESTATE

  (321) 850-2392

  1414 Bessmor Rd, Winter Park, FL 32789
• 

  

  /22

  $1,475 per month

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft
  • Condo for Rent

  2500 Lee Rd Unit 115, Winter Park, FL 32789

  Experience comfort and leisure in this charming 2-bedroom, 1-bathroom condo nestled within a highly sought-after lakefront community on picturesque Lake Killarney. Offering 851 sq. ft. of thoughtfully designed living space, this residence features modern upgrades including newer appliances, wood laminate flooring, and can come furnished. Ideally located less than a mile from I-4, the property

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  2500 Lee Rd Unit 115, Winter Park, FL 32789
• 

  /2

  $580,000 Sold Sep 04, 2025

  • 1,701 Sq Ft
  • $341/SF
  • 16 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2004

  915 Aragon Ave, Winter Park, FL 32789

  Nestled in a peaceful enclave near Park Avenue in Winter Park, this inviting 3 bedroom, 3 bathroom, 1,701 SF townhome offers classic Florida living with modern comforts. A welcoming entry opens to bamboo wood flooring that flows through the main living areas. The living room and adjacent dining space connect seamlessly to the gorgeous kitchen, featuring 42" wood cabinets, stainless appliances,

  Shelby Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  915 Aragon Ave, Winter Park, FL 32789
• 

  /2

  Est $494,505 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  1761 Indiana Ave Unit F, Winter Park, FL 32789
• 

  

  /15

  $189,900

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit B216, Winter Park, FL 32789

  Lovely 3 bedroom 2 bathroom second floor unit at Waterfall Cove in the heart of Winter Park, close to shopping, restaurants, schools and major roadways. The end unit features a nice open floorplan with lots of natural light. The kitchen is spacious and has lots of cabinet storage and countertop space it overlooks the large living room with sliding glass doors that lead out to the balcony with a

  

  Martha Grasty

  RE/MAX ASSURED

  (321) 381-3262

  1695 Lee Rd Unit B216, Winter Park, FL 32789
• 

  

  /23

  $1,688 - $5,756 per month

  Juno Winter Park

  Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  1305 Morgan Stanley Ave, Winter Park, FL 32789
• 

  /2

  $177,000 Sold Sep 04, 2025

  • 658 Sq Ft
  • $269/SF
  • 75 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1967

  1250 S Denning Dr Unit 108, Winter Park, FL 32789

  This move-in-ready, first-floor condo has been completely updated and is ready for its new owner. Enjoy newer flooring, fresh paint, an in unit washer/dryer, and modern fixtures throughout! Located in a well-maintained community with great amenities, including a pool. Conveniently situated in desirable Winter Park, close to shopping, dining, and major roadways. A great opportunity for homeowners

  Cleve Loveland LOVELAND PROPERTIES

  1250 S Denning Dr Unit 108, Winter Park, FL 32789
• 

  

  /39

  Est $684,828 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,488 Sq Ft

  311 E Morse Blvd Unit 6-1, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-1, Winter Park, FL 32789
• 

  

  /59

  $1,475,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  690 Osceola Ave Unit 604, Winter Park, FL 32789

  Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder’s unit with panoramic views of Lake Virginia from almost every room and its expansive full-width balcony. Welcome to Lakefront Luxury Living in the heart of Winter Park. This extraordinary Penthouse residence on the Chain of Lakes perfectly captures the essence of opulent Florida living. The 2-story lakefront home offers an

  Larry Slung COLDWELL BANKER RESIDENTIAL RE

  690 Osceola Ave Unit 604, Winter Park, FL 32789
• 

  

  /24

  $1,725 per month

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Condo for Rent

  851 Miles Ave Unit 21, Winter Park, FL 32789

  Enjoy a quiet but beautiful space at Aragon Condominiums. This first-floor corner unit allows for privacy with only one adjoining neighbor. It is a perfect place to call home with upgrades all around, including granite countertops, washer and dryer in unit, and a community pool just right outside your door. It is conveniently located in Winter Park, where you can enjoy many shops, restaurants,

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  851 Miles Ave Unit 21, Winter Park, FL 32789
• 

  /2

  $1,245,000 Sold Sep 03, 2025

  • 1,683 Sq Ft
  • $740/SF
  • 4 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1940

  171 Cortland Ave, Winter Park, FL 32789

  Come see this outstanding 15,000 sqft lot surrounded by multi-million dollar homes on one of Winter Parks picturesque tree lined brick streets just a short drive from Park Avenue. This property offers the option of updating and remodeling the existing charming 1,683 sqft 2 bedroom, 2 bath Cottage located on the property or building your dream home in one of the most beautiful residential areas

  Jerry Oller FANNIE HILLMAN & ASSOCIATES

  171 Cortland Ave, Winter Park, FL 32789
• 

  

  /43

  Est $1,796,401 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  1809 Harland Park Dr, Winter Park, FL 32789

  1809 Harland Park Dr, Winter Park, FL 32789
• 

  

  /28

  $649,900

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789

  Rare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away from the prestegious Park Avenue! Discover the perfect blend of luxury, comfort, and convenience with this immaculate, move-in-ready condo, in the heart of Winter Park. Recently transformed with meticulous attention to detail, this lock-and-leave gem boasts an elegant, high-end renovation that exudes

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789
• 

  

  /28

  $1,599 - $1,629 per month

  Elon Winter Park

  1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  712 Nicolet Ave, Winter Park, FL 32789
• 

  /2

  $355,000 Sold Sep 02, 2025

  • 1,235 Sq Ft
  • $287/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  1117 Park Green Place, Winter Park, FL 32789

  Charming One-Story Townhome in Prime Winter Park Location!Welcome to this adorable detached 3-bedroom, 2-bath townhome with a spacious 2-car garage, tucked away in the heart of Winter Park (32789). Just minutes from Winter Park Village, Fleming’s, and the boutiques and dining of Park Avenue, this home blends low-maintenance living with unbeatable convenience.Step inside to find a

  Kelly Sue Stonebreaker RE/MAX TOWN & COUNTRY REALTY

  1117 Park Green Place, Winter Park, FL 32789
• 

  

  /13

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit M, Winter Park, FL 32789

  700 Melrose Ave Unit M, Winter Park, FL 32789
• 

  

  /29

  $405,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft

  259 Blossom Ln, Winter Park, FL 32789

  Under contract-accepting backup offers. Charming Winter Park Block Home with Deeded Access to Lake Killarney – Solid, Updated Systems & Priced for Your Personal Touch!Welcome to this well-built 3-bedroom, 2-bath cement block home in one of Winter Park’s most desirable and established neighborhoods. . . . . . Built in 1954 and lovingly cared by the same owner for almost 40 years, this home

  Sherrie Wysong LEGACY REALTY & BROKERS LLC

  259 Blossom Ln, Winter Park, FL 32789
• 

  

  /24

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 913 Sq Ft
  • Condo for Rent

  1250 S Denning Dr Unit 233, Winter Park, FL 32789

  Located just minutes from Winter Park's famed Park Avenue, this charming 2 bed, 2 bathroom corner condominium features a light and bright open floor plan, updated finishes, views of Mead Gardens, and one of Central Florida's most sought after locations! As you enter the front door, you are immediately welcomed by views of Mead Botanical Gardens, Khaki oak wood-look luxury vinyl floors, an open

  Samuel Kingsford STOCKWORTH REALTY GROUP

  1250 S Denning Dr Unit 233, Winter Park, FL 32789
• 

  /2

  $1,595,000 Sold Sep 02, 2025

  • 3,267 Sq Ft
  • $488/SF
  • 27 Days On Market

  • 5 Beds
  • 4.5 Baths
  • Built 2025

  1733 Harmon Ave, Winter Park, FL 32789

  Experience the charm and elegance of Winter Park living in this beautifully designed 5-bedroom, 4.5-bath home offering 3,267 square feet of thoughtfully crafted space.This residence combines timeless architectural character with modern functionality,From the moment you enter, you’re welcomed by warm natural light, the first floor features an office with an open and inviting layout, and

  Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
• 

  

  /44

  Est $884,200 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  436 W Swoope Ave, Winter Park, FL 32789

  436 W Swoope Ave, Winter Park, FL 32789
• 

  

  /66

  $1,199,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,993 Sq Ft

  2525 Venetian Way, Winter Park, FL 32789

  Under contract-accepting backup offers. Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access This meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas

  Kimberly Slinger KELLY PRICE & COMPANY LLC

  2525 Venetian Way, Winter Park, FL 32789
• 

  

  /85

  $1,560 - $3,677 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
• 

  /2

  $920,000 Sold Sep 02, 2025

  • 2,265 Sq Ft
  • $406/SF
  • 9 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1764 Mondrian Cir, Winter Park, FL 32789

  Act quickly—only three units remain! We are excited to introduce a beautiful, brand-new modern brownstone located in the heart of Winter Park, with access to Lake Killarney. Nestled in an exclusive community of 30 contemporary townhomes, each residence is thoughtfully designed with exquisite finishes, expansive storefront-style windows, and 11-foot ceilings that welcome an abundance of natural

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1764 Mondrian Cir, Winter Park, FL 32789
• 

  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 687 Sq Ft

  700 Melrose Ave Unit G, Winter Park, FL 32789

  700 Melrose Ave Unit G, Winter Park, FL 32789
• 

  

  /31

  $1,490,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,838 Sq Ft

  2408 Lafayette Ave, Winter Park, FL 32789

  This brand new custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set

  Matthew Burks CORCORAN PREMIER REALTY

  2408 Lafayette Ave, Winter Park, FL 32789
• 

  

  /26

  $1,325 per month

  • 1 Bed
  • 1 Bath
  • 502 Sq Ft
  • Apartment for Rent

  1950 Killarney Dr Unit 2, Winter Park, FL 32789

  Neat and clean, 2nd floor apartment in the highly desirable Winter Park zip code of 32789. Recent updates include vinyl flooring throughout, refinished bathroom tub, new vanity, newer AC units, newer ceiling fans and redone screened porch. 1-car garage with automatic door opener. Rent includes water and lawn car. Beautiful setting across the street and views of Lake Killarney. Great Winter Park

  Terry Diederich KELLER WILLIAMS REALTY AT THE PARKS

  1950 Killarney Dr Unit 2, Winter Park, FL 32789
• 

  /2

  $1,740,000 Sold Aug 29, 2025

  • 2,964 Sq Ft
  • $587/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1983

  443 Beloit Ave, Winter Park, FL 32789

  Welcome to the timeless charm of Beloit Avenue, one of Winter Park’s most desired streets. This classic and elegant 3-bedroom, 2.5-bath residence offers nearly 3,000 square feet of thoughtfully designed living all on one level. Just two blocks from Park Avenue and a short stroll to the Winter Park Golf Course, the location is truly unmatched.Inside, high ceilings, detailed crown molding,

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  443 Beloit Ave, Winter Park, FL 32789
• 

  

  /15

  Not Listed For Sale

  • 2 Beds
  • 3,098 Sq Ft

  1858 Cornell Ave, Winter Park, FL 32789

  1858 Cornell Ave, Winter Park, FL 32789
• 

  

  /25

  $349,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,349 Sq Ft

  657 Overspin Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyers!** Welcome to your cozy Winter Park retreat! This charming 4-bedroom, 2-bath home blends comfort and convenience in one perfect package. Nestled on a spacious lot with a large backyard—ideal for entertaining, gardening, or playing

  Abby Nelson RE/MAX 200 REALTY

  657 Overspin Dr, Winter Park, FL 32789
• 

  

  /103

  $2,156 - $6,454 per month

  Paseo at Winter Park Village

  1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  940 W Canton Ave, Winter Park, FL 32789
• 

  /2

  $425,000 Sold Aug 29, 2025

  • Land
  • 0.32 Acre
  • $1,328,125 per Acre

  • 3 Days On Market

  1871 Staunton Ave, Winter Park, FL 32789

  A Double Lot Near Lake Killarney! This bungalow nestled on a generous 0.32-acre lot—one of the largest in the neighborhood—just one block from scenic Lake Killarney is perfect for something NEW. With a spacious backyard, mature landscaping, and even a shuffleboard court, this property offers a rare opportunity to create your very own backyard retreat. There's room to add a pool, a pickleball

  Greg Staker WATSON REALTY CORP.

  1871 Staunton Ave, Winter Park, FL 32789
• 

  

  /60

  Est $1,669,815 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft

  1318 Chapman Cir, Winter Park, FL 32789

  1318 Chapman Cir, Winter Park, FL 32789
• 

  

  /72

  $945,000

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  915 Garden Dr, Winter Park, FL 32789

  Step into this beautifully maintained Mid-Century Modern home, nestled in the prestigious Winter Park community and just a short three-minute stroll to the serene beauty of Mead Botanical Garden. A true raised ranch design, this home radiates warmth and character from the moment you arrive, featuring an expansive covered front patio that welcomes you inside.Inside, you’ll be greeted by

  Cassie Lamoureux KELLER WILLIAMS CLASSIC

  915 Garden Dr, Winter Park, FL 32789
• 

  

  /38

  $2,100 per month

  • 2 Beds
  • 1 Bath
  • 1,027 Sq Ft
  • House for Rent

  1450 Cavendish Rd, Winter Park, FL 32789

  WINTER PARK - Located in the highly desirable ORWIN MANOR neighborhood, this charming one-story 2BR/1BA single-family home offers 1,027 sq.ft. of living space, thoughtfully blending its original character with modern updates. The living room provides a comfortable and cozy gathering space, while the adjoining dinette is filled with natural light, creating an inviting setting for casual meals or

  Margaret Steiner KELLER WILLIAMS REALTY AT THE PARKS

  1450 Cavendish Rd, Winter Park, FL 32789
• 

  /2

  $940,000 Sold Aug 29, 2025

  • 2,646 Sq Ft
  • $355/SF
  • 17 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2024

  1840 Biscayne Dr, Winter Park, FL 32789

  Biscayne Bay, a recent Parade of Homes winner, is one of the latest custom builds by the trusted team at Konkol Custom Homes—and it’s ready for its very first owner. Set in a prime Winter Park location, this two-story home offers clean lines, high-end finishes, and a layout that fits real life.With just over 2,600 square feet under air, the home features 4 bedrooms and 3 full bathrooms.

  Jennifer King CORCORAN PREMIER REALTY

  1840 Biscayne Dr, Winter Park, FL 32789
• 

  

  /14

  Est $576,759 Not Listed For Sale

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

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

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