Homes in ZIP Code 32789

• 

  

  

  /38

  $564,900

  • 2 Beds
  • 1 Bath
  • 901 Sq Ft

  100 S Interlachen Ave Unit 410, Winter Park, FL 32789

  The Cloisters, one of Winter Park's established and sought-after communities features an ornate architectural design complemented by lush landscaping and an inviting entryway. This fourth-floor two-bedroom, one-bathroom condominium offers approximately 901 square feet with a spacious and modern living experience. Upon entering this residence, you are greeted with a bright and open living area

  Dee Lund COLDWELL BANKER REALTY

  100 S Interlachen Ave Unit 410, Winter Park, FL 32789
• 

  

  /2

  $1,800,000 Sold May 06, 2025

  • 3,444 Sq Ft
  • $523/SF
  • 1 Day On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2021

  2813 Northwood Blvd, Winter Park, FL 32789

  Modern living in Central Florida’s desirable Winter Park, this residence offers an elegant balance of refined design, elevated finishes and seamless indoor-outdoor living. Completed in 2021 and impeccably maintained, this two-story home features four generously sized bedrooms, a sun-filled private office, three-and-a-half baths, and an oversized two-car garage, equipped with EV charging, on a

  Candace Cassidy PREMIER SOTHEBY'S INTL. REALTY

  2813 Northwood Blvd, Winter Park, FL 32789
• 

  

  

  /22

  Est $222,972 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit E26, Winter Park, FL 32789

  700 Melrose Ave Unit E26, Winter Park, FL 32789
• 

  

  

  /47

  $1,999,500

  • 4 Beds
  • 3.5 Baths
  • 3,727 Sq Ft

  1840 Bryan Ave, Winter Park, FL 32789

  This custom 2014 built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all that Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1840 Bryan Ave, Winter Park, FL 32789
• 

  

  /2

  $780,000 Sold May 05, 2025

  • 1,351 Sq Ft
  • $577/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1971

  106 S Interlachen Ave Unit 317, Winter Park, FL 32789

  Experience unparalleled sophistication and tranquility with this extraordinary two-bedroom, two-bath condominium, boasting one of the rare and coveted water views in The Cloisters. Nestled on the serene shores of Lake Osceola, this residence offers a unique opportunity to enjoy stunning lake vistas that are available in only a small number of units within the complex. Spanning 1,351 square feet,

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  106 S Interlachen Ave Unit 317, Winter Park, FL 32789
• 

  

  /18

  Est $193,652 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

  1250 S Denning Dr Unit 107, Winter Park, FL 32789

  1250 S Denning Dr Unit 107, Winter Park, FL 32789
• 

  

  /37

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 1,766 Sq Ft

  2886 Carew Ave, Winter Park, FL 32789

  This charming 4 bedroom home is available now! With lots of open space, a cozy fireplace, and a walk-in closet in the primary bedroom, you will have plenty of room for the whole family. Conveniently located next to I-4, Winter Park, College Park, and just a stone's throw from downtown Orlando. A quiet neighborhood in the coveted Edgewater High School district, this home is just waiting to be

  Raina Lawton OLDE TOWN BROKERS INC

  2886 Carew Ave, Winter Park, FL 32789
• 

  /2

  $8,900,000 Sold May 02, 2025

  • 8,583 Sq Ft
  • $1037/SF
  • 1 Day On Market

  • 8 Beds
  • 8.5 Baths
  • Built 1995

  2001 Bett Mar Ln, Winter Park, FL 32789

  Discover an extraordinary lifestyle at this one-of-a-kind estate, elegantly situated on the shores of Lake Maitland in the distinguished Winter Park area. This remarkable property is unlike any other in the market, seamlessly blending sophisticated Mediterranean and Spanish architectural elements to create a serene and inviting retreat. Upon entering through the stately steel gates, you are

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  2001 Bett Mar Ln, Winter Park, FL 32789
• 

  

  /30

  Est $696,285 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,109 Sq Ft

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789

  100 S Interlachen Ave Unit 506, Winter Park, FL 32789
• 

  

  /38

  $675,000

  • 3 Beds
  • 2 Baths
  • 1,804 Sq Ft

  1399 Aloma Ave, Winter Park, FL 32789

  Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on a private lot in the heart of Winter Park, moments from Rollins College, Park Avenue, and Winter Park Hospital. Just a short walk provides coveted access to the Winter Park Chain of Lakes, bring your paddle board or canoe. Step inside the spacious formal living room with a

  Cheryl Bennett FLORIDA HOMES REALTY & MTG

  1399 Aloma Ave, Winter Park, FL 32789
• 

  /2

  $2,300,000 Sold May 02, 2025

  • 3,089 Sq Ft
  • $745/SF
  • 7 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  2814 Parkland Dr, Winter Park, FL 32789

  PRESENTING THE NEWEST WINTER PARK RESIDENCE BUILT BY M. LAHR HOMES! Just completed, this stunning custom level home has come together perfectly with design and finish features that have to be seen in person to be truly appreciated. The combination of a fantastic floor plan that integrates perfectly with the expansive covered outdoor patio/pool/spa/outdoor space makes this house feel nothing less

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2814 Parkland Dr, Winter Park, FL 32789
• 

  

  /29

  Est $1,058,393 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  100 S Interlachen Ave Unit 201, Winter Park, FL 32789

  100 S Interlachen Ave Unit 201, Winter Park, FL 32789
• 

  

  /43

  $1,749,000

  • 3 Beds
  • 3.5 Baths
  • 3,112 Sq Ft

  101 S New York Ave Unit 311, Winter Park, FL 32789

  Discover luxury living in this exquisite two-story condominium, located on the third floor of the highly sought-after Douglas Grand. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends entertaining with everyday comfort. Step into a blank canvas offering a clean landscape—free of flooring—allowing you to effortlessly bring your own design vision to life. Whether you

  Tiffany Grindstaff KELLY PRICE & COMPANY LLC

  101 S New York Ave Unit 311, Winter Park, FL 32789
• 

  /2

  $640,000 Sold May 02, 2025

  • 1,881 Sq Ft
  • $340/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2023

  2739 Riddle Dr, Winter Park, FL 32789

  Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances.$64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on

  JASON OLD BRAINARD REALTY

  2739 Riddle Dr, Winter Park, FL 32789
• 

  

  /28

  Est $513,749 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft

  535 N Interlachen Ave Unit 307, Winter Park, FL 32789

  535 N Interlachen Ave Unit 307, Winter Park, FL 32789
• 

  

  /18

  $2,499,000

  • 4,056 Sq Ft

  1903 S Lakemont Ave, Winter Park, FL 32792

  Location, location, location! This is an amazing opportunity to build/renovate on a premier lakefront lot in the charming and upscale Winter Park neighborhood of Orlando, Florida. Located on Lake Spier and across the street from the beautiful Baldwin Park, this exceptional-almost one acre property-includes six 1/1 units. This prime property is minutes from award winning restaurants, sidewalk

  Maria Tenner Platinum Properties Int'l Inc.

  1903 S Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $380,000 Sold May 02, 2025

  • 1,428 Sq Ft
  • $266/SF
  • 42 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning

  Dora Siler FOLIO REALTY LLC

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
• 

  /2

  Est $137,504 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft

  1695 Lee Rd Unit D210, Winter Park, FL 32789

  1695 Lee Rd Unit D210, Winter Park, FL 32789
• 

  

  /24

  $499,000

  • 2 Beds
  • 1 Bath
  • 954 Sq Ft

  3601 Midiron Dr, Winter Park, FL 32789

  BUILD YOUR DREAM HOME IN WINTER PARK!Nestled directly across from the historic Dubsdread Golf Course, this property offers a unique chance to invest in one of Orlando’s most sought-after neighborhoods. Situated on a generous 150' x 60' lot along Midiron Drive—a street experiencing a transformation with homes reaching over a million-dollar mark—making this property perfect for redevelopment.Living

  Juliana Usquiano EMPIRE NETWORK REALTY

  3601 Midiron Dr, Winter Park, FL 32789
• 

  /2

  $385,000 Sold May 02, 2025

  • 1,536 Sq Ft
  • $251/SF
  • 171 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

  Largest unit at Killarney Bay, set up as a town home -bedrooms upstairs town house with large screened in area back porch, new washer and dryer - wood floors throughout, close to Winter Park Village - complex is a small great location with great access to I-4 - Killarney Bay sits on Lake Killarney with private pool overlooking. Only 5 rental units are allowed at KB at any given time. Super clean

  Michael O'Shaughnessy MICHAEL O'SHAUGHNESSY, INC.

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789
• 

  

  /9

  Est $156,614 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit B103, Winter Park, FL 32789

  1695 Lee Rd Unit B103, Winter Park, FL 32789
• 

  

  /26

  $649,000

  • 2 Beds
  • 2 Baths
  • 1,057 Sq Ft

  225 E Canton Ave Unit 225, Winter Park, FL 32789

  This beautifully updated 2-bedroom, 2-bathroom corner unit is located in the highly desirable Winterset Condominiums on East Canton Avenue, just one block from Park Avenue in the heart of Winter Park. The unit features hardwood floors, crown molding, plantation shutters, and an open floorplan filled with natural light. The kitchen is fully upgraded with GE stainless steel appliances, a wine

  Richard Palmano PALMANO GROUP RE BROKERAGE LLC

  225 E Canton Ave Unit 225, Winter Park, FL 32789
• 

  /2

  $145,000 Sold May 02, 2025

  • 881 Sq Ft
  • $165/SF
  • 271 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1966

  1695 Lee Rd Unit D206, Winter Park, FL 32789

  Discover this charming 2-bedroom, 1-bathroom condo in the tranquil community of Waterfall Cove. With a covered balcony and a walk-in closet in the primary bedroom, this home is ready for its new owner. The community offers a playground, a pool, and includes cable and internet in the HOA fees. Conveniently located near Rollins College and Winter Park's Park Ave, you'll have access to a variety of

  Justin Adams EXP REALTY LLC

  1695 Lee Rd Unit D206, Winter Park, FL 32789
• 

  

  /33

  Est $194,029 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft

  1250 S Denning Dr Unit 109, Winter Park, FL 32789

  1250 S Denning Dr Unit 109, Winter Park, FL 32789
• 

  

  /15

  $200,000

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

  1695 Lee Rd Unit E215, Winter Park, FL 32789

  Move-in Ready Renovated Condo – Prime Location!This beautifully renovated condo offers both style and convenience, situated right next to the community pool and playground. Enjoy modern upgrades throughout, along with the added assurance of a Home Warranty America coverage plan, valued up to $500, for extra peace of mind. Plus, you'll be just minutes from restaurants, shopping, major roads,

  Kerem Munoz- Franquiz LA ROSA REALTY CENTRAL FLORIDA

  1695 Lee Rd Unit E215, Winter Park, FL 32789
• 

  /2

  $1,180,000 Sold May 01, 2025

  • 3,000 Sq Ft
  • $393/SF
  • 43 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1948

  181 N Phelps Ave, Winter Park, FL 32789

  Charming One-Story Home in the Heart of Winter Park with an incredible pool area. Nestled in the heart of Winter Park, this elegant one-story home features a classic brick circular driveway and a welcoming covered front porch. Inside, the original hardwood floors add warmth and character to this four-bedroom, four-bathroom residence plus an exquisite detached home-office room , located in the

  Iluska Kruse ORLANDO BROTHERS REAL ESTATE LLC

  181 N Phelps Ave, Winter Park, FL 32789
• 

  

  /29

  Est $200,187 Not Listed For Sale

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

  1695 Lee Rd Unit B102, Winter Park, FL 32789

  1695 Lee Rd Unit B102, Winter Park, FL 32789
• 

  

  /45

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 2,388 Sq Ft

  1341 Lyndale Blvd, Winter Park, FL 32789

  Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park Village, this beautifully renovated 4-bedroom, 3-bath home offers the ultimate in walkable luxury living. Nestled on a charming brick street lined with sidewalks, this residence combines timeless elegance with unbeatable convenience.Inside, enjoy 10’ ceilings, rich wood,

  Brandon Geers COMPASS FLORIDA LLC

  1341 Lyndale Blvd, Winter Park, FL 32789
• 

  /2

  $430,000 Sold May 01, 2025

  • 1,485 Sq Ft
  • $290/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  328 Lake Fair Ln, Winter Park, FL 32789

  Discover a true slice of paradise just minutes from downtown Orlando, nestled along the serene shores of Lake Fair. This meticulously maintained 3-bedroom, 2-bathroom home, built in 1958, reflects an era when craftsmanship and attention to detail were paramount. The moment you step through the front door, you’ll be captivated by the original pine floors, gleaming with character and charm.Straight

  Tom Langmann RE/MAX 200 REALTY

  328 Lake Fair Ln, Winter Park, FL 32789
• 

  

  /15

  Est $218,691 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 772 Sq Ft

  700 Melrose Ave Unit K22, Winter Park, FL 32789

  700 Melrose Ave Unit K22, Winter Park, FL 32789
• 

  

  /70

  $2,125,000

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

  2614 Parkland Dr, Winter Park, FL 32789

  Welcome to 2614 Parkland Drive—an exquisite, fully renovated luxury residence nestled in the heart of Winter Park, Florida, one of the most coveted locations in all of Central Florida. Zoned for the highly desired Audubon Park K-8 and Winter Park High School, this home combines timeless design with unmatched functionality and elegance. Completely remodeled in 2022, every inch of this home

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
• 

  /2

  $464,000 Sold May 01, 2025

  • 1,057 Sq Ft
  • $439/SF
  • 78 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1971

  215 E Canton Ave Unit 215, Winter Park, FL 32789

  How wonderful would it be to live in a location where you felt you were on vaction everyday? This lovely condo near Park Avenue in Winter Park is just that. Thoughtful design is central to the interior of this condominium. Outside it boasts its own mini patio. It also has a very unususal, very desirable feture. It has its own first floor private entrance in close proximity to its personal parking

  Harris Ganey HARRISS M GANEY REALTY

  215 E Canton Ave Unit 215, Winter Park, FL 32789
• 

  

  /33

  Est $1,226,459 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,834 Sq Ft

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789
• 

  

  /38

  $659,000

  • 2 Beds
  • 2.5 Baths
  • 1,718 Sq Ft

  640 Killarney Bay Ct Unit 4, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Tucked away on the tranquil shores of Lake Killarney, this impeccably remodeled two-story residence offers a rare opportunity to enjoy waterfront living with unmatched convenience. Just steps from Hillstone, Trader Joe’s, and Winter Park Village, this 2-bedroom, 2.5-bathroom home is the perfect blend of modern sophistication and timeless

  Brandon Geers COMPASS FLORIDA LLC

  640 Killarney Bay Ct Unit 4, Winter Park, FL 32789
• 

  /2

  $595,000 Sold May 01, 2025

  • 1,162 Sq Ft
  • $512/SF
  • 211 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1953

  1848 Mizell Ave, Winter Park, FL 32789

  Prime Winter Park lot and/or home for sale -2 bedrooms / 2 bathrooms1,162 heated Sq. Ft. with single car garage1,754 gross square feetRemodeled kitchen and large backyardWinter Park High School A grade school - Elementary and Middle Schools grade B

  Jorge Zea BLUE LIGHTHOUSE REALTY INC

  1848 Mizell Ave, Winter Park, FL 32789
• 

  

  /28

  Est $184,498 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 211, Winter Park, FL 32789

  2500 Lee Rd Unit 211, Winter Park, FL 32789
• 

  

  /42

  $3,595,000

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

  2171 Forrest Rd, Winter Park, FL 32789

  On one of Winter Park’s most scenic brick-lined streets, this exceptional two-story residence commands attention on a spacious corner lot, blending timeless architectural elegance with modern luxury. Built in 2016 by the highly regarded Rex-Tibbs Development & Construction, the home showcases quality craftsmanship throughout, from its striking curb appeal to its impeccably appointed interiors. A

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2171 Forrest Rd, Winter Park, FL 32789
• 

  /2

  $799,000 Sold Apr 30, 2025

  • Land
  • 0.28 Acre
  • $2,853,571 per Acre

  • 2 Days On Market

  2320 Janice Ave, Winter Park, FL 32789

  Amazing opportunity to build your dream home in Winter Park. A tremendous location with just a short stroll to East End Market and all the shops and restaurants Corrine Drive has to offer! Zoned for the Audubon K-8 school that you can also walk to! This lot is over a 1/4 of an acre and is tucked away at the end of a dead end street for privacy. This is one you don't want to miss!

  Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2320 Janice Ave, Winter Park, FL 32789
• 

  

  /75

  Est $238,821 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 226, Winter Park, FL 32789

  2500 Lee Rd Unit 226, Winter Park, FL 32789
• 

  

  /49

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft

  1020 Mayfield Ave, Winter Park, FL 32789

  Exquisite, Luxury Listing in the Heart of Winter Park! Stunning, single-story residence, customized and remodeled by Phil Kean Design Group. Open and spacious, 2,600 + SF interior layout which boasts 4 bedrooms, 3 full baths, a home office, living/dining spaces, a chef’s kitchen, and more. Throughout the home are beautiful hardwood floors, beam and coffered ceilings, plantation shutters, French

  Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789

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