Homes in ZIP Code 32789

• 

  

  

  /36

  $5,800,000

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft

  1221 Richmond Rd, Winter Park, FL 32789

  An Award-Winning Architectural Masterpiece built by Chris Salhab with Valdara Custom HomesCompleted 2024Parade of Homes Showcase Home – Grand Award WinnerAurora Awards – Custom Home Grand Award5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Deeded Lake AccessWelcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of

  Audra Wilks KELLER WILLIAMS WINTER PARK

  1221 Richmond Rd, Winter Park, FL 32789
• 

  

  

  /23

  $1,650 per month

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

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great location. Don’t miss the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
• 

  

  /2

  $718,500 Sold Jun 13, 2025

  • 2,069 Sq Ft
  • $347/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1981

  1130 Washington Ave Unit 11C, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. A rare (and low-maintenance!) gem, this 3 bed/2.5 bath home is located just around the corner from Park Avenue and Rollins College. Tucked away in the most perfect location, this 2-story Winter Park condo was stripped down to the studs and completely remodeled in 2007 with all new plumbing, electrical, ductwork, flooring, appliances, and natural gas

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1130 Washington Ave Unit 11C, Winter Park, FL 32789
• 

  

  

  /31

  Est $668,494 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft

  775 Mcintyre Ave Unit 9, Winter Park, FL 32789

  775 Mcintyre Ave Unit 9, Winter Park, FL 32789
• 

  

  

  /29

  $390,000

  • 2 Beds
  • 1 Bath
  • 1,028 Sq Ft

  1516 Pinewood Dr, Winter Park, FL 32789

  PINEWOOD SUB N/9 LOT 12 BLK AWell-maintained, modest 2-1 home in College Park with carport, deck, and porch. Home materials include laminate and tile flooring, granite kitchen countertops, energy efficient windows, vinyl siding, and metal roof. All appliances included (washer, dryer, refrigerator, dishwasher, oven/stove with range hood, microwave). Also includes backyard garden, working

  Matt Buttner LIST NOW REALTY, LLC

  1516 Pinewood Dr, Winter Park, FL 32789
• 

  

  /21

  $6,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • House for Rent

  2237 Howard Dr, Winter Park, FL 32789

  We are focused on short term rentals. Contact owner / agent for dates already booked. You will be amazed by the natural beauty of the waterfront and century oaks that welcome you every time you come through your front door. Come see this fully furnished, masterfully remodeled, 3 bedroom, 2 bath, with a hidden half bath in the office. A Mid-modern home that represents everything that is lakefront

  Ryan Feely COLEDEV REAL ESTATE LLC

  2237 Howard Dr, Winter Park, FL 32789
• 

  /2

  $645,000 Sold Jun 13, 2025

  • 1,910 Sq Ft
  • $338/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  796 Mcintyre Ave, Winter Park, FL 32789

  Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home, perfectly situated on a tree-lined brick street within walking distance to Rollins College and all that Park Avenue has to offer. A charming driveway leads to your two-car garage and private front entrance. Upon entering, you'll be greeted by a bright and airy townhome that

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  796 Mcintyre Ave, Winter Park, FL 32789
• 

  /2

  Est $720,474 Not Listed For Sale

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

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
• 

  

  /74

  $1,750,000

  • 3 Beds
  • 4 Baths
  • 2,964 Sq Ft

  1270 Arlington Place, Winter Park, FL 32789

  Modern Elegance in the Heart of Winter Park!Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste.A long paver driveway welcomes

  Brian Mitnik RE/MAX 200 REALTY

  1270 Arlington Place, Winter Park, FL 32789
• 

  

  /15

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Apartment for Rent

  1055 S Kentucky Ave Unit 4, Winter Park, FL 32789

  Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dining room with Kitchen complete with all appliances included and great counter space. The first bedroom has a nice space with a walking closet. The master bedroom is spacious and bright with a large walk-in closet that also leads into the private bathroom! Bathrooms are very

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1055 S Kentucky Ave Unit 4, Winter Park, FL 32789
• 

  /2

  $890,000 Sold Jun 12, 2025

  • 2,265 Sq Ft
  • $393/SF
  • 114 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1762 Mondrian Cir, Winter Park, FL 32789

  Act now - only two new units remain! Introducing a stunning brand-new modern brownstone in the heart of Winter Park, offering access to Lake Killarney. Located in an exclusive community of 30 contemporary townhomes, each meticulously designed residence boasts exquisite finishes, expansive storefront-style windows, and 11' ceilings to flood the interiors with natural light. This 3-bedroom, 3 bath

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1762 Mondrian Cir, Winter Park, FL 32789
• 

  

  /50

  Est $2,019,752 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,151 Sq Ft

  270 E Lake Sue Ave, Winter Park, FL 32789

  270 E Lake Sue Ave, Winter Park, FL 32789
• 

  

  /53

  $3,400,000

  • 5 Beds
  • 5.5 Baths
  • 4,296 Sq Ft

  473 Fletcher Place, Winter Park, FL 32789

  Experience the perfect blend of luxury, lifestyle, and location in this completely custom 2017 Lundev build, just one mile from the boutiques and dining of Park Avenue and less than 100 feet from access to Lake Osceola, perfect for paddleboarding or launching a canoe.Tucked away on a quiet, tree-lined street, this residence makes a striking first impression with it's stunning elevation

  Brandon Geers COMPASS FLORIDA LLC

  473 Fletcher Place, Winter Park, FL 32789
• 

  

  /13

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Apartment for Rent

  1055 S Kentucky Ave Unit 2, Winter Park, FL 32789

  Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dining room with Kitchen complete with all appliances included and great counter space. The first bedroom has a nice space with a walking closet. The master bedroom is spacious and bright with a large walk-in closet that also leads into the private bathroom! Bathrooms are very

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1055 S Kentucky Ave Unit 2, Winter Park, FL 32789
• 

  /2

  $1,625,000 Sold Jun 12, 2025

  • 4,227 Sq Ft
  • $384/SF
  • 95 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 2003

  1470 Place Picardy, Winter Park, FL 32789

  Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1470 Place Picardy, Winter Park, FL 32789
• 

  

  /49

  Est $2,164,728 Not Listed For Sale

  180 Whipple Ave, Winter Park, FL 32789

  180 Whipple Ave, Winter Park, FL 32789
• 

  

  /41

  $170,000

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

  1695 Lee Rd Unit D116, Winter Park, FL 32789

  Location, location, location!! And priced to sell!! This 3 bedroom 2 bathroom corner unit condo is conveniently located within a short drive distance to Rollins College, UCF, Valencia College, hospitals, shopping, dining, and entertainment! The unit is located on the first floor and has an open floor plan, spacious kitchen with plenty of cabinet space (all appliances are included) 3 well

  Madalay Fleming LA ROSA REALTY KISSIMMEE

  1695 Lee Rd Unit D116, Winter Park, FL 32789
• 

  

  /16

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,258 Sq Ft
  • Apartment for Rent

  1055 S Kentucky Ave Unit 1, Winter Park, FL 32789

  Spacious two-bedroom, two bath condo available now! This is a FIRST FLOOR apartment with a spacious living room and dining room with Kitchen complete with all appliances included and great counter space. The first bedroom has a nice space with a walking closet. The master bedroom is spacious and bright with a large walk-in closet that also leads into the private bathroom! Bathrooms are very

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1055 S Kentucky Ave Unit 1, Winter Park, FL 32789
• 

  /2

  $385,000 Sold Jun 11, 2025

  • 1,262 Sq Ft
  • $305/SF
  • 101 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1955

  1930 Albert Lee Pkwy, Winter Park, FL 32789

  Tucked away on a quiet street yet just minutes from downtown Winter Park, College Park, and downtown Orlando, this beautifully updated 1955 ranch offers the perfect blend of peaceful living and urban convenience. With 2 bedrooms, 2 baths, and 1,262 square feet of thoughtfully renovated space, this home is move-in ready and full of character. As you enter, you’re greeted by a large, open living

  Carol van den Berg FLORIDA ONE REAL ESTATE LLC

  1930 Albert Lee Pkwy, Winter Park, FL 32789
• 

  

  /40

  Est $516,691 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft

  2145 Lake Dr Unit A-26, Winter Park, FL 32789

  2145 Lake Dr Unit A-26, Winter Park, FL 32789
• 

  

  /51

  $840,000

  • 2 Beds
  • 2 Baths
  • 1,143 Sq Ft

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789

  Welcome to The Cloisters—a prestigious lakefront community nestled in the heart of Winter Park, perfectly positioned between the timeless charm of Park Avenue and the serene beauty of Lake Osceola. This fully furnished second-floor residence has been meticulously redesigned and renovated to maximize both space and style, offering the comfort of a thoughtfully designed home, enhanced by luxurious,

  Lois Rawson COLDWELL BANKER RESIDENTIAL RE

  100 S Interlachen Ave Unit 204, Winter Park, FL 32789
• 

  

  /7

  $1,450 per month

  • 1 Bed
  • 1 Bath
  • 960 Sq Ft
  • Townhouse for Rent

  1512 Indiana Ave Unit B, Winter Park, FL 32789

  Spacious ONE BEDROOM , one bath CONDO available now! This is a first floor apartment with a spacious living room and dining room and Kitchen complete with all appliances included and great counter space. The master bedroom is spacious and bright with a large walk-in closet that also leads into the bathroom! Bathroom with shower. Washer and dryer combo included! Just a mile away from the amazing

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  1512 Indiana Ave Unit B, Winter Park, FL 32789
• 

  /2

  $849,900 Sold Jun 10, 2025

  • 1,776 Sq Ft
  • $479/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  1791 Spruce Ave, Winter Park, FL 32789

  Welcome to this stunning, fully renovated 3-bedroom, 2-bath residence nestled in the highly sought-after Winter Park community. Thismeticulously upgraded home blends style, comfort, and functionality in an open-concept layout that includes spacious living, dining and kitchen areas adorned with elegant wood flooring and crown molding throughout. The custom-designed kitchen is a chef’s dream,

  Betsy Breton-Garcia KELLER WILLIAMS WINTER PARK

  1791 Spruce Ave, Winter Park, FL 32789
• 

  

  /17

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft

  700 Melrose Ave Unit K, Winter Park, FL 32789

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

  

  /41

  $800,000

  • Land
  • 0.17 Acre
  • $4,705,882 per Acre

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789

  Here it is! Almost impossible to find 2 adjacent 75x100 R-3 lots for a total of 75x200 or 15,000 sq/ft in top Winter Park location! Located at northwest corner of proposed Winter Park Commons project. The vacant lot to be simultaneously purchased with adjacent parcel (TAX ID 06-22-30-1168-02-022) fronting Webster with BONUS 4/2 Bungalow. Walk to WP Village, Park Ave, WP9 Golf, Hannibal Square

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave Unit REAR LOT, Winter Park, FL 32789
• 

  

  /32

  $2,500 per month

  • 2 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • House for Rent

  626 Baffie Ave, Winter Park, FL 32789

  Great location, very near I-4 access just off Fairbanks in College Park/Winter Park. Oversized paver driveway and parking area. 2 bedrooms with one bathroom, and an extra room that could be used as an office. Bathroom has shower/tub combination, Home was built in 1938 and is charming and well maintained. Large screen porch with ceiling fans covers the entire front of the house. Home has

  Kathleen Penkacik GRACE REALTY, INC.

  626 Baffie Ave, Winter Park, FL 32789
• 

  /2

  $987,500 Sold Jun 10, 2025

  • 2,220 Sq Ft
  • $445/SF
  • 101 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1959

  1585 Chestnut Ave, Winter Park, FL 32789

  Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish-style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4-bedroom, 2.5-bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best

  Ashley Landers KELLER WILLIAMS WINTER PARK

  1585 Chestnut Ave, Winter Park, FL 32789
• 

  

  /28

  Est $1,899,163 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,715 Sq Ft

  664 Osceola Ave Unit 302, Winter Park, FL 32789

  664 Osceola Ave Unit 302, Winter Park, FL 32789
• 

  

  /34

  $800,000

  • 4 Beds
  • 2 Baths
  • 1,008 Sq Ft

  770 W Webster Ave, Winter Park, FL 32789

  Stop the car! Check out this classic 4/2 Florida ranch plus vacant lot ready for renovation! Newer roof, water heater. HW and tile floors, screened porch, utility/storage room. 1 car carport. OR develop your dream project on this hard to find R-3 lot! Adjacent 75x100 R-3 vacant lot (TAX ID 06-22-30-1168-02-023) on the south side to be purchased simultaneously, for a total of 75x200 or

  Lisa Gould KELLER WILLIAMS WINTER PARK

  770 W Webster Ave, Winter Park, FL 32789
• 

  

  /17

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
• 

  /2

  $260,000 Sold Jun 06, 2025

  • 710 Sq Ft
  • $366/SF
  • 28 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

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

  Fantastic 2 bed/ 1 bath - first floor condo in cool, mid-century building on Lake Killarney. This home is next to Trader Joes, Hillstone's and across the street from Winter Park Village! Lakefront Winter Park Condo Community Ground Floor Remodeled 2 Bedroom 1 Bath Condo, Remodeled Kitchen and Bath, Includes Washer Dryer Inside Unit. Wood Look Laminate and Tile Floors. Lake Front Amenities, Boat

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

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

  

  /71

  Est $1,035,304 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,389 Sq Ft

  792 W Swoope Ave Unit 4, Winter Park, FL 32789

  792 W Swoope Ave Unit 4, Winter Park, FL 32789
• 

  

  /7

  $825,000

  • Land
  • 0.19 Acre
  • $4,342,105 per Acre

  1780 Bryan Ave, Winter Park, FL 32789

  Positioned in the heart of Winter Park, this exceptional lot presents a rare opportunity to build your dream home in one of the prestigious communities in Central Florida. Just minutes from the charm and elegance of Park Avenue, you’ll enjoy effortless access to the Winter Park chain of lakes, boutique shopping, acclaimed dining, art galleries and the vibrant cultural scene that defines the

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  1780 Bryan Ave, Winter Park, FL 32789
• 

  /2

  $1,200 per month

  • 1 Bed
  • 1 Bath
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave Unit 2, Winter Park, FL 32789

  Cozy Efficiency for Rent in Winter ParkThis charming efficiency unit at 2011 Cornell Ave is perfect for those seeking a comfortable and affordable living space. Recently renovated, the unit features modern appliances, a spacious living area, and plenty of natural light. Located in a peaceful neighborhood with easy access to downtown Winter Park, shopping, dining, and parks, this

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave Unit 2, Winter Park, FL 32789
• 

  /2

  $825,000 Sold Jun 06, 2025

  • 2,563 Sq Ft
  • $322/SF
  • 40 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2020

  705 Baffie Ave, Winter Park, FL 32789

  Discover modern living at its finest in this stunning contemporary home in the heart of Winter Park! Built in 2020, this spacious four-bedroom, 2.5-bath residence offers over 2,500 square feet of beautifully designed living space ideal for families of all sizes. The first floor features a bright, open-concept kitchen with sleek finishes, a large island and ample storage, seamlessly flowing into a

  Jon Messeroff PREMIER SOTHEBY'S INTL. REALTY

  705 Baffie Ave, Winter Park, FL 32789
• 

  

  /67

  Est $4,624,401 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,617 Sq Ft

  840 N Park Ave, Winter Park, FL 32789

  840 N Park Ave, Winter Park, FL 32789
• 

  

  /21

  $949,900

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  2823 Wright Ave, Winter Park, FL 32789

  Here’s your chance to own something truly special in Winter Park! This gorgeous lakefront home sits on over HALF AN ACRE, a rare find in this area - allowing opportunity to BUILD YOUR DREAM HOME! Step inside to find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes, ideal for both entertaining and everyday living. The home boasts new windows

  Tal Busidan TAL BUSIDAN PA

  2823 Wright Ave, Winter Park, FL 32789
• 

  

  /41

  $4,500,000 Sold Jun 05, 2025

  • 6,000 Sq Ft
  • $750/SF
  • 3 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2012

  2118 Lake Dr, Winter Park, FL 32789

  "The Point House" on lake Killarney. Rarely available oasis, this spectacular lake front residence is positioned on a peninsula with .90 acres and over 440+ feet of lake frontage with unobstructed lake views to the south, west and east. Constructed in 2012, this home features 6,000 living square footage (3,977 on the 1st level / 1,950 on the 2nd level), 4,000 sq. ft. of outdoor space,

  Quentin Green COMPASS FLORIDA LLC

  2118 Lake Dr, Winter Park, FL 32789
• 

  

  /52

  Est $2,163,773 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,617 Sq Ft

  2015 N Park Ave, Winter Park, FL 32789

  2015 N Park Ave, Winter Park, FL 32789
• 

  

  /11

  $3,950,000

  • Land
  • 8 Acres
  • $473,621 per Acre

  2403 Euston Rd, Winter Park, FL 32789

  Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately 432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable acres

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  2403 Euston Rd, Winter Park, FL 32789

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