Homes in ZIP Code 32789

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  /28

  $145,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 243, Winter Park, FL 32789

  Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

  Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
• 

  

  

  /20

  $3,600 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  220 Overlook Rd, Winter Park, FL 32789

  Charming Cape Cod–style home available for lease in the heart of Winter Park. Ideally located just one block from Lake Mizell and moments from Park Avenue and Rollins College, this residence offers an exceptional lifestyle surrounded by premier shops, dining, and local amenities.The home features a spacious and inviting floor plan with a large living room, sunroom or dining area, and two

  Julie Bombardo PREMIER SOTHEBY'S INTL. REALTY

  220 Overlook Rd, Winter Park, FL 32789
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  /2

  $1,300,000 Sold Sep 22, 2025

  1371 Lyndale Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft
  • Built 1949

  Last Sold Summary

  • 4% Below List Price
  • $479/SF
  • 8 Days On Market

  Current Estimated Value $1,283,867

  Last Listing Agent Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
• 

  

  /2

  Est $857,498 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft

  1245 Wisconsin Ave, Winter Park, FL 32789

  1245 Wisconsin Ave, Winter Park, FL 32789
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  /47

  $1,199,000

  • 3 Beds
  • 2.5 Baths
  • 2,578 Sq Ft

  1541 Westchester Ave, Winter Park, FL 32789

  Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1541 Westchester Ave, Winter Park, FL 32789
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  /44

  $7,000 per month

  • 4 Beds
  • 5 Baths
  • 3,302 Sq Ft
  • House for Rent

  519 Park North Ct, Winter Park, FL 32789

  Discover refined single-story living at 519 Park North Court, an exceptional luxury rental in the heart of Winter Park. This beautifully appointed four-bedroom, three-and-a-half-bath residence offers an ideal blend of elegance and comfort, with a thoughtfully designed split floor plan that ensures both privacy and functionality for modern living.The home welcomes you with a formal living room

  Kelly Price KELLY PRICE & COMPANY LLC

  519 Park North Ct, Winter Park, FL 32789
• 

  /2

  $235,000 Sold Jan 29, 2026

  613 Orange Tree Ct Unit 507, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $187/SF
  • 10 Days On Market

  Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
• 

  /2

  Est $1,622,065 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,174 Sq Ft

  101 S New York Ave Unit 303, Winter Park, FL 32789

  101 S New York Ave Unit 303, Winter Park, FL 32789
• 

  

  /21

  $259,000

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

  1500 Gay Rd Unit 18A, Winter Park, FL 32789

  Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard And Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has matching Cabinets and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both Bedrooms. Windows and Sliding

  Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 18A, Winter Park, FL 32789
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  /16

  $1,270 per month

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Townhouse for Rent

  2183 Crandon Ave Unit 1/2, Winter Park, FL 32789

  This 2 bedroom, 1 bathroom, 2nd floor unit is located in the heart of Winter Park. Enjoy all of Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious living area, a lovely kitchen, a screened patio area, and a shared laundry room

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  2183 Crandon Ave Unit 1/2, Winter Park, FL 32789
• 

  /2

  $1,000,000 Sold Apr 04, 2025

  1001 Tuscany Place, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,458 Sq Ft
  • Built 1978

  Last Sold Summary

  • 22% Below List Price
  • $407/SF
  • 141 Days On Market

  Current Estimated Value $1,063,146

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1001 Tuscany Place, Winter Park, FL 32789
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  /38

  Est $3,176,312 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,367 Sq Ft

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  140 E Morse Blvd Unit G, Winter Park, FL 32789
• 

  

  /17

  $195,000

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft

  1500 Gay Rd Unit 5, Winter Park, FL 32789

  Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features

  Jacob Hara TRANSCEND REALTY

  1500 Gay Rd Unit 5, Winter Park, FL 32789
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  /12

  $7,000 per month

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft
  • House for Rent

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  A chic and trendy residence and winter park in an incredible location. A fully remodeled, one level four bedroom home with a fence corner lot. This home has an amazing curb appeal with its wide half circle, paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living and entertaining, with designer porcelain tile, trendy light

  Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
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  /2

  $1,002,000 Sold May 31, 2025

  1265 Park Pointe Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Above List Price
  • $437/SF
  • 4 Days On Market

  Current Estimated Value $991,951

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  /30

  Est $1,572,508 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft

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

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

  

  /30

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,167 Sq Ft

  726 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of modern elegance and prime location. The gourmet kitchen boasts 42” black cabinets, granite countertops, a decorative backsplash, and stainless steel appliances, making it a stunning focal point of the home. The open-concept dining and living room create a spacious feel, while ceramic tile and wood floors enhance

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 N Pennsylvania Ave, Winter Park, FL 32789
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  /75

  $3,700 per month

  • 5 Beds
  • 3 Baths
  • 2,132 Sq Ft
  • House for Rent

  730 W Swoope Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Charming Winter Park Corner Home for Rent - 730 W Swoope Ave Experience the best of Winter Park living in this beautifully renovated corner home! Located just three blocks from the iconic Park Avenue, this spacious 5-bedroom, 3 bathroom residence offers over 2,200 square feet of updated living space. The bright, open design and private rooms provide

  Andres Ospina Rivera LPT REALTY, LLC

  730 W Swoope Ave, Winter Park, FL 32789
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  /2

  $1,975,000 Sold Mar 27, 2025

  140 Dana Way, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 3,441 Sq Ft
  • Built 2011

  Last Sold Summary

  • 6% Below List Price
  • $574/SF
  • 16 Days On Market

  Current Estimated Value $1,987,396

  Last Listing Agent Maria Blanchard OLDE TOWN BROKERS INC

  140 Dana Way, Winter Park, FL 32789
• 

  /2

  Est $359,224 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
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  /35

  $259,000 Pending

  • 2 Beds
  • 1 Bath
  • 762 Sq Ft

  2009 Cornell Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Unlock potential in one of Central Florida’s most desirable pockets! This centrally located Winter Park home shines with major updates already completed including a 2018 roof, 2022 HVAC, and fresh interior paint. Just bring a little extra love to elevate the finishes and create instant equity. Perfect as a long-term rental, short-term investment, or a

  Juliet Saldarriaga ORLANDO HOME DEALER LLC

  2009 Cornell Ave, Winter Park, FL 32789
• 

  

  /11

  $3,800 per month

  • 4 Beds
  • 2 Baths
  • 1,474 Sq Ft
  • House for Rent

  1690 Dale Ave, Winter Park, FL 32789

  Located in one of the best areas of Winter Park, this home offers top- rated schools, welcoming neighborhood, and unbeatable convenience. just a mile from Park Avenue, you will enjoy easy access to shops, restaurants, and all the charm Winter Park is known for.With plenty to do nearby and a family - friendly environment, this is the perfect place to raise a family and enjoy the Winter Park

  Farzaneh Alijani ZAMIN INC

  1690 Dale Ave, Winter Park, FL 32789
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  /2

  $230,000 Sold Aug 29, 2025

  1500 Gay Rd Unit 7A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $224/SF
  • 205 Days On Market

  Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

  1500 Gay Rd Unit 7A, Winter Park, FL 32789
• 

  

  /30

  Est $624,007 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  1086 Azalea Ln Unit 1, Winter Park, FL 32789
• 

  

  /26

  $379,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft

  1007 Early Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to your next chapter at 1007 Early Ave in Winter Park, a charming 3-bedroom, 2-bathroom home. Thoughtfully maintained, this home combines character with modern comfort. Step inside to find inviting living spaces and enjoy peace of mind with a roof replaced in 2019. The spacious backyard is perfect for entertaining, gardening, or simply relaxing

  Eric Gross EXP REALTY LLC

  1007 Early Ave, Winter Park, FL 32789
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  /36

  $4,895 per month

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  1580 Oakhurst Ave, Winter Park, FL 32789

  Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1580 Oakhurst Ave, Winter Park, FL 32789
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  /2

  $3,450,000 Sold Jul 25, 2025

  182 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 4,812 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $717/SF
  • 61 Days On Market

  Current Estimated Value $3,422,449

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
• 

  /2

  Est $1,141,618 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft

  1782 Mondrian Cir, Winter Park, FL 32789

  1782 Mondrian Cir, Winter Park, FL 32789
• 

  

  /26

  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie Ave, Winter Park, FL 32789
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  /39

  $7,900 per month

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft
  • House for Rent

  300 Killarney Dr, Winter Park, FL 32789

  Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

  Kelly Price KELLY PRICE & COMPANY LLC

  300 Killarney Dr, Winter Park, FL 32789
• 

  /2

  $1,950,000 Sold Sep 16, 2025

  141 Oakwood Way, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,909 Sq Ft
  • Built 2015

  Last Sold Summary

  • 14% Below List Price
  • $499/SF
  • 170 Days On Market

  Current Estimated Value $1,955,862

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
• 

  /2

  Est $823,698 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1776 Mondrian Cir, Winter Park, FL 32789

  1776 Mondrian Cir, Winter Park, FL 32789
• 

  

  /14

  $2,289,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,334 Sq Ft

  2722 Eastern Pkwy, Winter Park, FL 32789

  Under Construction. Masterfully designed new construction by LUIH Luxury Homes, where architectural elegance and refined livability meet an unbeatable lifestyle. Located in the Audubon Park School District just a short stroll from the iconic East End Market. From its captivating façade to its meticulously curated interiors, every element of this residence has been crafted for those who expect the

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  2722 Eastern Pkwy, Winter Park, FL 32789
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  /49

  $6,995 per month

  • 4 Beds
  • 5 Baths
  • 3,478 Sq Ft
  • House for Rent

  1350 Lyndale Blvd, Winter Park, FL 32789

  Gorgeous, Custom & recently renovated! This home features 4 bedrooms, 3 full baths & 2 half baths. Spacious, light & bright with 10’ ceilings, Brazilian cherry floors, and a gourmet kitchen. The kitchen is a chef's dream and perfect for entertaining. It boasts natural wood cabinets, large center island, dual fuel six-burner range, wine fridge and a built-in refrigerator. It overlooks a casual

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1350 Lyndale Blvd, Winter Park, FL 32789
• 

  

  /45

  $1,100,000 Sold May 29, 2025

  708 Balmoral Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,786 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $395/SF
  • 130 Days On Market

  Current Estimated Value $1,110,139

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
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  /41

  Est $1,562,703 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,287 Sq Ft

  1005 S Pennsylvania Ave, Winter Park, FL 32789

  1005 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /41

  $1,140,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft

  1150 Kenwood Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Nestled in the heart of Winter Park, this exquisite 3-bedroom, 2.5-bath residence offers 2,557 square feet of beautifully designed living space along with a spacious 2-car garage. Situated on a charming, tree-lined brick street just minutes from Park Avenue, the home’s first level includes a welcoming living room, versatile bonus/flex space, dining room

  JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  1150 Kenwood Ave, Winter Park, FL 32789
• 

  

  /12

  $1,525 per month

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Townhouse for Rent

  1565 Michigan Ave, Winter Park, FL 32789

  Cute and comfortable 1/2 of a duplex in the heart of Winter Park. This 2 bedroom 1 bath unit features ceramic tile throughout, ceiling fans in the bedroom, private washer and dryer and a full sized kitchen. The unit shares a back yard and there is limited storage on site as well. The unit is located minutes from I 4, shopping, restaurants and Rollins College.

  Troy Hensley BHHS FLORIDA REALTY

  1565 Michigan Ave, Winter Park, FL 32789
• 

  /2

  $699,000 Sold Jun 30, 2025

  1632 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $394/SF
  • 110 Days On Market

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1632 Haven Dr, Orlando, FL 32803
• 

  /2

  Est $748,458 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft

  1421 Wooddale Ave, Winter Park, FL 32789

  1421 Wooddale Ave, Winter Park, FL 32789

Showing Results 161 - 200, Page 5 of 18