Homes in ZIP Code 32789

• 

  

  

  /43

  $525,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  720 W Webster Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends

  

  Vincent Cordaro

  SERHANT

  (321) 341-3712

  720 W Webster Ave, Winter Park, FL 32789
• 

  

  

  /65

  $6,995 Per Month

  • 5 Beds
  • 4 Baths
  • 2,918 Sq Ft
  • House for Rent

  2075 Jewell Ave, Winter Park, FL 32789

  FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a

  

  Paul Jimenez

  URBANISTA BROKERS

  (321) 483-3119

  2075 Jewell Ave, Winter Park, FL 32789
• 

  

  /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 $2,106,050

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /2

  Est $1,073,262 Not Listed For Sale

  1975 Biscayne Dr, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,270 Sq Ft
  • Built 2020

  1975 Biscayne Dr, Winter Park, FL 32789

  Last Sold Summary

  • 8% Above List Price
  • $304/SF
  • 68 Days On Market

  • Last Sold Price $995,000
  • May 09, 2025

  Last Listing Agent nana Ahn SOGO REAL ESTATE SERVICES LLC
• 

  

  

  /31

  $380,000

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  440 Cambridge Blvd, Winter Park, FL 32789

  **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 to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 461-2860

  440 Cambridge Blvd, Winter Park, FL 32789
• 

  

  /75

  Starting at $1,416 Per Month

  • 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.

  Bainbridge Winter Park

  (689) 219-8568

  

  1400 Morgan Stanley Ave, Winter Park, FL 32789
• 

  /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 $664,935

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
• 

  /2

  Not Listed For Sale

  1630 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 2024

  1630 Haven Dr, Orlando, FL 32803

  Last Sold Summary

  • $392/SF
  • 53 Days On Market

  • Last Sold Price $654,000
  • May 09, 2025

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY
• 

  

  /41

  $245,000 Pending

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 229, Winter Park, FL 32789

  Under contract-accepting backup offers. DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 252-5096

  2500 Lee Rd Unit 229, Winter Park, FL 32789
• 

  

  /26

  $1,465 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) 336-5615

  2500 Lee Rd Unit 244, Winter Park, FL 32789
• 

  /2

  $955,000 Sold Feb 24, 2026

  512 Clarendon Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $338/SF
  • 21 Days On Market

  Current Estimated Value $966,525

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
• 

  /2

  Est $724,461 Not Listed For Sale

  1806 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft
  • Built 2018

  1806 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $342/SF
  • 61 Days On Market

  • Last Sold Price $690,000
  • May 08, 2025

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
• 

  

  /65

  $1,100,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  1800 Magnolia Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. NEW PRICE! Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  (321) 306-4359

  1800 Magnolia Ave, Winter Park, FL 32789
• 

  

  /28

  Starting at $1,637 Per Month

  • 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

  Elon Winter Park

  (689) 219-5245

  

  712 Nicolet 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 $278,950

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
• 

  /2

  Est $131,073 Not Listed For Sale

  1695 Lee Rd Unit E205, Winter Park, FL 32789

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

  1695 Lee Rd Unit E205, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $148/SF
  • 25 Days On Market

  • Last Sold Price $130,000
  • May 09, 2025

  Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY
• 

  

  /23

  $139,990

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E103, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the

  

  Jason Price

  RE/MAX SELECT GROUP

  (321) 324-0916

  1695 Lee Rd Unit E103, Winter Park, FL 32789
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  /53

  Starting at $1,887 Per Month

  • 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,

  Juno Winter Park

  (689) 219-5062

  

  1305 Morgan Stanley Ave, Winter Park, FL 32789
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  /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 $1,275,430

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
• 

  /2

  Est $596,969 Not Listed For Sale

  777 S Denning Dr Unit B, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,762 Sq Ft
  • Built 2004

  777 S Denning Dr Unit B, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $342/SF
  • 37 Days On Market

  • Last Sold Price $602,500
  • May 09, 2025

  Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK
• 

  

  /22

  $262,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 20D, Winter Park, FL 32789

  LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (689) 399-5336

  1500 Gay Rd Unit 20D, Winter Park, FL 32789
• 

  

  /50

  Starting at $1,585 Per Month

  • Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  Seven41 Winter Park

  (689) 219-8058

  

  741 Clay St, 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

  Current Estimated Value $2,256,477

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
• 

  /2

  Est $1,789,509 Not Listed For Sale

  2813 Northwood Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,444 Sq Ft
  • Built 2021

  2813 Northwood Blvd, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $523/SF
  • 1 Day On Market

  • Last Sold Price $1,800,000
  • May 06, 2025

  Last Listing Agent Candace Cassidy PREMIER SOTHEBY'S INTL. REALTY
• 

  

  /21

  $261,500

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 24B, Winter Park, FL 32789

  ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 450-8960

  1500 Gay Rd Unit 24B, Winter Park, FL 32789
• 

  

  /50

  Starting at $1,550 Per Month

  • 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

  Berkshire Winter Park

  (689) 220-6346

  

  1874 Harmon Ave, Winter Park, FL 32789
• 

  /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

  Current Estimated Value $2,675,463

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
• 

  /2

  Est $613,574 Not Listed For Sale

  2906 Rapidan Trail, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1965

  2906 Rapidan Trail, Winter Park, FL 32789

  Last Sold Summary

  • 12% Above List Price
  • $236/SF
  • 4 Days On Market

  • Last Sold Price $550,000
  • May 08, 2025

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  /52

  $1,150,000

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

  1981 Blue Ridge Rd, Winter Park, FL 32789

  Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 232-3531

  1981 Blue Ridge Rd, Winter Park, FL 32789
• 

  

  /50

  Starting at $1,832 Per Month

  • 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

  Paseo at Winter Park Village

  (689) 219-4397

  

  940 W Canton Ave, Winter Park, FL 32789
• 

  /2

  $775,000 Sold May 21, 2025

  1818 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 189 Days On Market

  Current Estimated Value $813,430

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1818 Mondrian Cir, Winter Park, FL 32789
• 

  /2

  Est $2,537,253 Not Listed For Sale

  254 Sylvan Blvd, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 3,653 Sq Ft
  • Built 2000

  254 Sylvan Blvd, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $710/SF
  • 8 Days On Market

  • Last Sold Price $2,594,550
  • May 09, 2025

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK
• 

  

  /41

  $510,000

  • 2 Beds
  • 1 Bath
  • 1,073 Sq Ft

  1036 Aragon Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just

  

  Tim Veigle

  WATSON REALTY CORP

  (321) 516-0689

  1036 Aragon Ave, Winter Park, FL 32789
• 

  

  /18

  Starting at $1,330 Per Month

  • Studio - 2 Beds

  311 N Knowles Ave, Winter Park, FL 32789

  Park East Apartments, a charming community of studio, one, and two bedroom homes in the heart of Winter Park, FL. Spacious, modern interiors welcome you inside, as a collection of convenient resident amenities allows you to relax and enjoy residential life in style.Choose from a wide array of floor plans and layouts to find the home that meets your needs. Your fully equipped kitchen opens

  Park East - Park Knowles Apartments

  (689) 207-6470

  

  311 N Knowles Ave, Winter Park, FL 32789
• 

  /2

  $1,590,000 Sold Mar 06, 2026

  1166 Oaks Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 2018

  Last Sold Summary

  • 12% Below List Price
  • $556/SF
  • 153 Days On Market

  Current Estimated Value $1,592,749

  Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
• 

  

  /42

  Est $1,551,593 Not Listed For Sale

  1805 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft
  • Built 2014

  1805 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $483/SF
  • 12 Days On Market

  • Last Sold Price $1,475,000
  • Dec 29, 2023

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
• 

  

  /36

  $399,999

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  721 Dunbar St, Winter Park, FL 32789

  Welcome to 721 Dunbar St in Winter Park, a 2-bedroom, 2-bath home with a simple layout and plenty of potential. This property offers a comfortable starting point for everyday living and a great opportunity for buyers who want a home they can make their own over time. Inside, the home offers practical living spaces and a layout that works well for daily routines. The two-bedroom, two-bath setup

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 344-8781

  721 Dunbar St, Winter Park, FL 32789
• 

  

  /8

  $1,650

  Total Monthly Price

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

  700 Melrose Ave, Winter Park, FL 32789

  Charming 1BR/BA condo in desirable Winter Park Gardens (+55 community). Recently renovated and located in the highly sought-after Winter Park Gardens community in Winter Park, FL. This bright and inviting second floor unit overlooks the pool and has an elevator nearby. Within walking distance of Park Avenue's Shops, restaurants and other activities. (no pets allowed )Adjacent to Winter

  (978) 984-3360

  700 Melrose Ave, Winter Park, FL 32789
• 

  /2

  $2,050,000 Sold Apr 30, 2026

  1205 Mayfield Ave, Winter Park, FL 32789

  • Land
  • 23,958 Sq Ft
  • $3,727,273 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 89 Days On Market

  Current Estimated Value $2,230,763

  Last Listing Agent Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
• 

  /2

  Est $459,831 Not Listed For Sale

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft
  • Built 2008

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  Last Sold Summary

  • 11% Above List Price
  • $258/SF

  • Last Sold Price $413,000
  • Jun 01, 2023

  Last Listing Agent Brock Stocksett HOMEVEST REALTY

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