Homes in ZIP Code 32789

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  /35

  $260,000

  • 2 Beds
  • 1 Bath
  • 804 Sq Ft

  151 N Orlando Ave Unit 101, Winter Park, FL 32789

  Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops,

  

  Elizabeth Fowler

  THE FLORIDA PROPERTY SHOP SALE

  (321) 463-4625

  151 N Orlando Ave Unit 101, Winter Park, FL 32789
• 

  

  

  /15

  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • House for Rent

  1891 Oglesby Ave, Winter Park, FL 32789

  Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus

  

  Paul Jimenez

  URBANISTA BROKERS

  (321) 977-5674

  1891 Oglesby Ave, Winter Park, FL 32789
• 

  

  /2

  $130,000 Sold May 09, 2025

  1695 Lee Rd Unit E205, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  Last Sold Summary

  • 10% Below List Price
  • $148/SF
  • 25 Days On Market

  Current Estimated Value $138,534

  Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY

  1695 Lee Rd Unit E205, Winter Park, FL 32789
• 

  

  /2

  Est $396,485 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft

  535 N Interlachen Ave Unit 101, Winter Park, FL 32789

  535 N Interlachen Ave Unit 101, Winter Park, FL 32789
• 

  

  

  /15

  $134,900

  • 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) 516-0992

  1695 Lee Rd Unit B216, Winter Park, FL 32789
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  /26

  $1,475 per month

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Condo for Rent

  2500 Lee Rd Unit 244, Winter Park, FL 32789

  Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

  

  Rustina Gibson

  RE/MAX VANTAGE

  (321) 252-2868

  2500 Lee Rd Unit 244, Winter Park, FL 32789
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  /2

  $2,144,000 Sold Aug 21, 2025

  1077 N Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,462 Sq Ft
  • Built 2004

  Last Sold Summary

  • $619/SF
  • 0 Days On Market

  Current Estimated Value $2,125,651

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
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  /2

  Est $282,797 Not Listed For Sale

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

  700 Melrose Ave Unit M33, Winter Park, FL 32789

  700 Melrose Ave Unit M33, Winter Park, FL 32789
• 

  

  /51

  $1,199,900

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome home to this beautifully renovated 4-bedroom, 2-bathroom home nestled on a desirable corner lot in the heart of Winter Park’s Timberlane Shores community. Boasting

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 599-3889

  1981 Blue Ridge Rd, Winter Park, FL 32789
• 

  

  /75

  $1,553 - $3,581 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

  $1,450,000 Sold Feb 27, 2025

  1101 Kenwood Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,955 Sq Ft
  • Built 2024

  Last Sold Summary

  • 23% Below List Price
  • $491/SF
  • 363 Days On Market

  Current Estimated Value $1,471,545

  Last Listing Agent Jennifer King CORCORAN PREMIER REALTY

  1101 Kenwood Ave, Winter Park, FL 32789
• 

  /2

  Est $334,871 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft

  500 N Pennsylvania Ave Unit E, Winter Park, FL 32789

  500 N Pennsylvania Ave Unit E, Winter Park, FL 32789
• 

  

  /23

  $449,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,685 Sq Ft

  2148 Blossom Ln, Winter Park, FL 32789

  Under contract-accepting backup offers. Located in the desirable Winter Park area, this newly listed 3-bedroom, 2-bathroom home at 2148 Blossom Lane offers excellent value and investment potential. This well-maintained house features 1,685 square feet of comfortable living space, perfect for families or investors looking for a solid opportunity. The home's prime location puts you just minutes

  

  Scot Hartwell

  PLATINUM REAL ESTATE

  (321) 478-2108

  2148 Blossom Ln, Winter Park, FL 32789
• 

  

  /7

  $1,475 per month

  • 1 Bed
  • 1 Bath
  • 653 Sq Ft
  • Condo for Rent

  1250 S Denning Dr Unit 208, Winter Park, FL 32789

  A+++ Location in Winter Park. Remodeled 1 bedroom and bath apartment. Close to everything Advent Health, Park Avenue, Rollins College, Orange Avenue, Fairbanks, 17-92 and 1-4. No pets please.

  Ruth Harris COLDWELL BANKER RESIDENTIAL RE

  1250 S Denning Dr Unit 208, Winter Park, FL 32789
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  /2

  $675,000 Sold Jul 10, 2025

  1511 Chestnut Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft
  • Built 1960

  Last Sold Summary

  • $529/SF
  • 1 Day On Market

  Current Estimated Value $659,068

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
• 

  /2

  Est $349,575 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,204 Sq Ft

  647 Huntington Ave Unit 8, Winter Park, FL 32789

  647 Huntington Ave Unit 8, Winter Park, FL 32789
• 

  

  /40

  $243,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft

  613 Orange Tree Ct Unit 507, Maitland, FL 32751

  Come to your new home centrally located between Downtown Maitland and Winter Park. Close to the conveniences of retail shopping, restaurants, the Sunrail Station and I-4 to get you around Central Florida quickly. Enter into your one story condo to an open living, dining and kitchen floorplan for lots of space and flexibility. Ceramic tile throughout, 5" base molding, 6 panel doors and updated

  Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
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  /85

  $1,470 - $4,940 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
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  /2

  $280,000 Sold Jul 30, 2025

  700 Melrose Ave Unit A22, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  Last Sold Summary

  • 11% Below List Price
  • $261/SF
  • 130 Days On Market

  Current Estimated Value $288,492

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
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  /2

  Est $446,905 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,012 Sq Ft

  1401 Devon Rd, Winter Park, FL 32789

  1401 Devon Rd, Winter Park, FL 32789
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  /44

  $3,399,999

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Brian Scanlon SCANLON REALTY GROUP LLC

  1761 Legion Dr, Winter Park, FL 32789
• 

  

  /21

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft
  • House for Rent

  216 Rippling Ln, Winter Park, FL 32789

  Welcome to this inviting home located in a private neighborhood just minutes from top restaurants, shops, and playgrounds. The open floor plan is filled with natural light, creating a warm and spacious living environment that’s perfect for everyday living and entertaining. Step outside to the gated, oversized backyard, ideal for relaxing, hosting gatherings, or enjoying outdoor activities in a

  Lorena Hernandez SAFETYNET REALTY

  216 Rippling Ln, Winter Park, FL 32789
• 

  /2

  $1,300,000 Sold Aug 28, 2025

  1500 Mizell Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,303 Sq Ft
  • Built 1957

  Last Sold Summary

  • $564/SF
  • 2 Days On Market

  Current Estimated Value $1,270,234

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
• 

  /2

  Est $933,674 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,100 Sq Ft

  251 Dana Way, Winter Park, FL 32789

  251 Dana Way, Winter Park, FL 32789
• 

  

  /41

  $2,350,000

  • 5 Beds
  • 4 Baths
  • 3,948 Sq Ft

  1205 Mayfield Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This beautiful two-story residence is located in the highly desired Temple Heights neighborhood in the heart of Winter Park. Situated on an expansive double lot, this well-maintained home offers over 3,900 sq ft of heated living space and features 5 bedrooms and 4 bathrooms in the main home, plus a large separate pool home/In-Law Suite complete with

  Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
• 

  

  /28

  $1,615 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

  $2,295,000 Sold Dec 16, 2025

  1661 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,570 Sq Ft
  • Built 2025

  Last Sold Summary

  • 12% Below List Price
  • $643/SF
  • 26 Days On Market

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
• 

  /2

  Est $625,371 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,716 Sq Ft

  1419 Miller Ave, Winter Park, FL 32789

  1419 Miller Ave, Winter Park, FL 32789
• 

  

  /49

  $1,215,000

  • 6 Beds
  • 4 Baths
  • 2,284 Sq Ft

  726 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living areas, kitchens, and

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 N Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /24

  $1,800 per month

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

  Unlisted Address

  Available for immediate move-in, this comfortable second-floor corner condo offers a peaceful setting with playground and pool views. The home features a fully carpeted interior, a spacious kitchen with a pantry closet, and a newer refrigerator. Washer and dryer are included for added convenience. Great balcony for relaxing on the cooler Florida days! Located in desirable Winter Park, you'll

  Yarmmys Vargas ZEN LIVING HOMES LLC

  Unlisted Address
• 

  /2

  $2,700,000 Sold Oct 30, 2025

  1020 Mayfield Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $1,014/SF
  • 149 Days On Market

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
• 

  /2

  Est $471,963 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1402 Bessmor Rd, Winter Park, FL 32789

  1402 Bessmor Rd, Winter Park, FL 32789
• 

  

  /29

  $1,225,000

  • 3 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  501 W Canton Ave, Winter Park, FL 32789

  Introducing a rare opportunity to own a brand-new, luxury modern townhome just steps from Park Avenue in the heart of Winter Park. This stunning two-story, all-block construction residence offers the perfect blend of design, quality, and location—within walking distance to Hannibal Square, Rollins College, upscale dining, boutique shopping, and more. Inside, soaring 13-foot ceilings, custom wood

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  501 W Canton Ave, Winter Park, FL 32789
• 

  

  /53

  $1,850 - $8,285 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
• 

  

  /89

  $830,000 Sold Mar 11, 2025

  1223 Formosa Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,834 Sq Ft
  • Built 1940

  Last Sold Summary

  • 31% Below List Price
  • $216/SF
  • 240 Days On Market

  Current Estimated Value $849,806

  Last Listing Agent Farah Bloom KELLER WILLIAMS WINTER PARK

  1223 Formosa Ave, Winter Park, FL 32789
• 

  

  /42

  Est $1,566,537 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
• 

  

  /53

  $4,595,000

  • 4 Beds
  • 5 Baths
  • 3,181 Sq Ft

  1336 College Point, Winter Park, FL 32789

  Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1336 College Point, Winter Park, FL 32789
• 

  

  /15

  $1,975 per month

  • 4 Beds
  • 2 Baths
  • 1,180 Sq Ft
  • House for Rent

  275 N Capen Ave, Winter Park, FL 32789

  This unique, old Florida style 4 ba / 2 ba 1180 sqft home features a single car garage, two baths, three smaller bedrooms and a master bedroom with walk in closet. Less than a mile away from desirable Park Avenue, and Rollins Collage. Washer/dryer included. Application Fee: $50 each adult (18+)**Full Credit/Skip/Eviction/Background check is done on all applicants.**Please have the

  Kenneth Warren PREMIER MANAGEMENT GROUP INC

  275 N Capen Ave, Winter Park, FL 32789
• 

  /2

  $4,100,000 Sold Apr 18, 2025

  1691 Chestnut Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 4,582 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $895/SF
  • 1 Day On Market

  Current Estimated Value $3,840,500

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

  1691 Chestnut Ave, Winter Park, FL 32789
• 

  /2

  Est $488,466 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

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