Homes in ZIP Code 32789

• 

  

  

  /41

  $1,550,000

  • 4 Beds
  • 3.5 Baths
  • 2,985 Sq Ft

  507 Country Club Dr, Winter Park, FL 32789

  Designed for elevated living in the heart of Winter Park, this custom-built pool home on the largest interior lot in the community combines timeless craftsmanship, modern comfort, and an unbeatable location just steps from premier shopping and dining. Featuring 4 bedrooms, 3.5 bathrooms, a private pool, and a spacious backyard, this stunning home is thoughtfully designed for both comfortable

  Lianna D'Angelo SOTERA LIVING

  507 Country Club Dr, Winter Park, FL 32789
• 

  

  

  /19

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 850 Sq Ft
  • House for Rent

  1925 S Lakemont Ave, Winter Park, FL 32792

  Enjoy lakefront living in this charming waterfront Studio B apartment with beautiful views of Baldwin Lake, offering a desirable Winter Park address and the highly sought-after Baldwin Park lifestyle. Located directly across from the Lake Baldwin Trail, you’ll love being near scenic surroundings and stunning sunsets over the water. This studio includes a private bathroom and a brand new

  Elena Sanchez BALDWIN PARK REALTY LLC

  1925 S Lakemont Ave, Winter Park, FL 32792
• 

  

  /2

  $2,285,000 Sold Nov 19, 2025

  521 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,883 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $588/SF
  • 118 Days On Market

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  521 S Phelps Ave, Winter Park, FL 32789
• 

  

  /2

  Est $747,282 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,218 Sq Ft

  800 Greens Ave, Winter Park, FL 32789

  800 Greens Ave, Winter Park, FL 32789
• 

  

  

  /25

  $329,900

  • 1 Bed
  • 1 Bath
  • 570 Sq Ft

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789

  Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue!Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 7-11, Winter Park, FL 32789
• 

  

  /27

  $1,360 - $2,151 per month

  Westmount at Winter Park

  Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  1701 Lee Rd, Winter Park, FL 32789
• 

  /2

  $580,000 Sold May 16, 2025

  1392 Indiana Ave, Winter Park, FL 32789

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

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 123 Days On Market

  Current Estimated Value $552,286

  Last Listing Agent Cody Hancock COLDWELL BANKER RESIDENTIAL RE

  1392 Indiana Ave, Winter Park, FL 32789
• 

  /2

  Est $510,589 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,048 Sq Ft

  2842 Eastern Pkwy, Winter Park, FL 32789

  2842 Eastern Pkwy, Winter Park, FL 32789
• 

  

  /27

  $329,000

  • 2 Beds
  • 2.5 Baths
  • 1,133 Sq Ft

  184 Sandlewood Trail Unit 2, Winter Park, FL 32789

  Located in the heart of Winter Park, this beautifully fully renovated 2-bedroom, 2.5-bath condominium offers the perfect blend of modern design and walkable lifestyle. The open-concept floor plan creates a bright and airy living space ideal for both everyday living and entertaining. The completely updated kitchen features all-new appliances, contemporary finishes, and seamless flow into the

  TOM NOELKE NOELKE REALTY

  184 Sandlewood Trail Unit 2, Winter Park, FL 32789
• 

  

  /23

  $2,150 per month

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

  1250 S Denning Dr Unit 112, Winter Park, FL 32789

  Nestled in one of Winter Park’s most desirable pockets, the Mead Garden Condominium offers the perfect blend of tranquility and convenience. Set beside the lush, 47-acre Mead Botanical Garden, the community provides a peaceful, nature-rich backdrop while keeping you just minutes from everything that makes Winter Park exceptional. This ground floor unit boasts its own washer/dryer combo for

  Catherine Williams COLDWELL BANKER RESIDENTIAL RE

  1250 S Denning Dr Unit 112, Winter Park, FL 32789
• 

  /2

  $4,772,500 Sold Sep 18, 2025

  765 Via Lugano, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,319 Sq Ft
  • Built 2019

  Last Sold Summary

  • $1,105/SF
  • 1 Day On Market

  Current Estimated Value $4,745,878

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

  765 Via Lugano, Winter Park, FL 32789
• 

  /2

  Est $3,490,684 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 5,097 Sq Ft

  1821 Summerland Ave, Winter Park, FL 32789

  1821 Summerland Ave, Winter Park, FL 32789
• 

  

  /34

  $1,599,900 New Construction

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting

  Kelly Price KELLY PRICE & COMPANY LLC

  607 Ellen Dr, Winter Park, FL 32789
• 

  

  /27

  $1,236 - $2,425 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, Winter Park, FL 32789
• 

  /2

  $3,100,000 Sold Jun 27, 2025

  731 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,260 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 45 Days On Market

  Current Estimated Value $2,996,206

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
• 

  /2

  Est $2,587,452 Not Listed For Sale

  • 5 Beds
  • 7 Baths
  • 4,487 Sq Ft

  1450 Mizell Ave, Winter Park, FL 32789

  1450 Mizell Ave, Winter Park, FL 32789
• 

  

  /22

  $298,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake

  Chris Creegan CREEGAN GROUP

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
• 

  

  /52

  $11,500 per month

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Condo for Rent

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

  Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
• 

  /2

  $2,700,000 Sold Oct 02, 2025

  1445 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,489 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $601/SF
  • 2 Days On Market

  Current Estimated Value $2,661,937

  Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

  1445 Holts Grove Cir, Winter Park, FL 32789
• 

  /2

  Est $1,401,923 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,503 Sq Ft

  907 Moss Ln, Winter Park, FL 32789

  907 Moss Ln, Winter Park, FL 32789
• 

  

  /50

  $1,425,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,306 Sq Ft

  850 Juanita Rael, Winter Park, FL 32789

  Under contract-accepting backup offers. Location, location, location. Sought after location on the North end of Park Avenue. Avoid the traffic in and out of Downtown Winter Park while being minutes away from everything on the Avenue. One of the very few single level homes of this quality in Winter Park 32789.Single story ranch on a lovely, private, large corner lot. 2306 heated and cooled

  Brad Grosberg PHIL KEAN REAL ESTATE LLC

  850 Juanita Rael, Winter Park, FL 32789
• 

  

  /15

  $3,275 per month

  • 3 Beds
  • 1.5 Baths
  • 1,058 Sq Ft
  • House for Rent

  304 Granada Dr, Winter Park, FL 32789

  Property Id: 2306077Welcome to our renovated Winter Park home! This modern one-story property features 3 bedrooms plus a Loft. Enjoy the large backyard with an extra-large pool , furnished Gazebo and outdoor shower. Great Neighborhood with amazing schools. This home has an EV charger energy efficient appliances, security alarm and security cameras.To many feature’s and amenities to

  304 Granada Dr, Winter Park, FL 32789
• 

  /2

  $916,000 Sold Jul 17, 2025

  609 Langholm Dr, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $462/SF
  • 8 Days On Market

  Current Estimated Value $910,445

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
• 

  

  /42

  Est $1,604,570 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
• 

  

  /43

  $1,339,000

  • 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
• 

  

  /39

  $2,880 per month

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • House for Rent

  2992 Chantilly Ave, Winter Park, FL 32789

  Welcome to this inviting 3-bedroom, 2-bath single-family pool home. In addition to the main living areas, the home features a large bonus room that can easily be used as an extra bedroom, game room, home office, or entertainment space to fit your lifestyle. Enjoy year-round relaxation in the bright sunroom, which opens directly to the private pool, creating the perfect indoor-outdoor living

  Randy Pierre LEMUEL PROPERTY MANAGEMENT LLC

  2992 Chantilly Ave, Winter Park, FL 32789
• 

  /2

  $2,599,000 Sold Feb 14, 2025

  1000 Via Tuscany Oaks Way, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,002 Sq Ft
  • Built 2003

  Last Sold Summary

  • $649/SF
  • 2 Days On Market

  Current Estimated Value $2,564,670

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1000 Via Tuscany Oaks Way, Winter Park, FL 32789
• 

  /2

  Est $489,518 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
• 

  

  /4

  $299,999

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
• 

  

  /20

  $1,750 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 3B, Winter Park, FL 32789

  Lakefront Living at Its Best: Renovated 1st Floor End Unit on Lake KillarneyExperience the charm and convenience of lakefront living in this recently renovated first-floor end unit, nestled in a picturesque community on Lake Killarney.Key Features:Stunning Sunset Views: Enjoy breathtaking sunsets from the lakefront deck, perfect for relaxing evenings.Water Activities: Benefit from

  1500 Gay Rd Unit 3B, Winter Park, FL 32789
• 

  /2

  $3,485,000 Sold Oct 17, 2025

  2171 Forrest Rd, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,565 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $763/SF
  • 134 Days On Market

  Current Estimated Value $3,402,806

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

  2171 Forrest Rd, Winter Park, FL 32789
• 

  

  /43

  Est $1,762,315 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
• 

  

  /8

  $1,825,000

  • 4 Beds
  • 2.5 Baths
  • 2,674 Sq Ft

  633 Balmoral Rd, Winter Park, FL 32789

  An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area’s private and pristine ski lakes with no public boat ramp, this property offers a rare combination of privacy, location and potential. Set on over a half-acre of lakefront land, the property features a four-bedroom, two-and-a-half-bath, single-story

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  633 Balmoral Rd, Winter Park, FL 32789
• 

  

  /50

  $3,150 per month

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • House for Rent

  1835 Edwin Blvd, Winter Park, FL 32789

  Charming bungalow on a brick street in beautiful Winter Park, available January 12, 2026. This 3-bedroom, 2-bathhome offers a great split floorplan and newer finishes. The kitchen and both primary en-suite and secondary bathroomshave been completely remodeled with premium finishes. The home boasts a newer roof, hardwood and stone floorsthroughout, with granite counters, white

  Vincent Scarlatos CORCORAN PREMIER REALTY

  1835 Edwin Blvd, Winter Park, FL 32789
• 

  /2

  $520,000 Sold Mar 31, 2025

  1810 Taylor Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Below List Price
  • $372/SF
  • 0 Days On Market

  Current Estimated Value $535,482

  Last Listing Agent Julia Dalessandro FANNIE HILLMAN & ASSOCIATES

  1810 Taylor Ave, Winter Park, FL 32789
• 

  /2

  Est $1,836,874 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 4,638 Sq Ft

  1411 Border Dr, Winter Park, FL 32789

  1411 Border Dr, Winter Park, FL 32789
• 

  

  /55

  $1,549,000 Open Sun 11AM - 2PM

  • 5 Beds
  • 4 Baths
  • 2,895 Sq Ft

  1473 Berkshire Ave, Winter Park, FL 32789

  Exquisite New 2025 Luxury Home in the Heart of Winter Park - Welcome to 1473 Berkshire Avenue - a stunning, brand-new 2025 luxury residence located in the highly sought-after town of Winter Park, Florida. This beautifully crafted two-story Mediterranean-style home blends timeless architecture with modern elegance, offering 5 bedrooms, 4 full bathrooms, and just under 2,900 square feet of

  Crystal Canina Golden Group Realty LLC

  1473 Berkshire Ave, Winter Park, FL 32789
• 

  

  /20

  $4,495 per month

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 2/28!!$4495.00 for a 15 MO LEASE$4695.00 12 MO LEASENestled within the exclusive 400 West enclavean intimate community of just nine residences just moments from Park Avenuethis modern townhome seamlessly combines superior craftsmanship, elegant interiors, and outstanding walkability. Entering through either the private

  438 W Swoope Ave, Winter Park, FL 32789
• 

  /2

  $3,950,000 Sold Jun 17, 2025

  33 Eastwind Ln, Maitland, FL 32751

  • 5 Beds
  • 4.5 Baths
  • 4,715 Sq Ft
  • Built 2024

  Last Sold Summary

  • $838/SF
  • 0 Days On Market

  Current Estimated Value $3,822,637

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

  33 Eastwind Ln, Maitland, FL 32751
• 

  

  /44

  Est $847,279 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

Showing Results 81 - 120, Page 3 of 18