Homes in ZIP Code 32789

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  /47

  $3,350,000

  • 5 Beds
  • 6 Baths
  • 4,143 Sq Ft

  516 Henkel Cir, Winter Park, FL 32789

  This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. The property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate

  Morgan Seefried KELLER WILLIAMS WINTER PARK

  516 Henkel Cir, Winter Park, FL 32789
• 

  

  

  /27

  $4,495 per month

  • 3 Beds
  • 2.5 Baths
  • 2,317 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  $4495.00 for a 15 MO LEASE$4695.00 12 MO LEASE Nestled within the exclusive 400 West enclave intimate community of just nine residences, just moments from Park Avenue this modern townhome seamlessly combines superior craftsmanship, elegant interiors, and outstanding walkability. Entering through either the private garage or the charming garden-style front path, you're welcomed into a

  Nancy Guadagnino SPECIALIZED PROPERTY MANAGEMENT

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

  $1,645,000 Sold May 20, 2025

  681 Balmoral Rd, Winter Park, FL 32789

  • Land
  • 1.14 Acres
  • $1,442,982 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 55 Days On Market

  Current Estimated Value $1,618,558

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
• 

  

  /2

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 687 Sq Ft

  700 Melrose Ave Unit G, Winter Park, FL 32789

  700 Melrose Ave Unit G, Winter Park, FL 32789
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  /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
• 

  

  /20

  $3,186 per month

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Condo for Rent

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789

  Experience a Central Florida retreat and feel at home in this Winter Park apartment, perfect for couples, families, or solo travelers. Sunlight filters through the leafy canopy onto a modest porch where you can unwind after a day of theme park thrills or downtown exploring.The full kitchen is equipped with stainless steel appliances, a stovetop, oven, microwave, and a refrigerator. A full

  1307 Formosa Ave Unit ID1250011P, Winter Park, FL 32789
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  /2

  $3,200,000 Sold Apr 30, 2025

  1833 Loch Berry Rd, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,770 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $671/SF
  • 5 Days On Market

  Current Estimated Value $2,957,584

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1833 Loch Berry Rd, Winter Park, FL 32789
• 

  

  /15

  Not Listed For Sale

  • 2 Beds
  • 3,098 Sq Ft

  1858 Cornell Ave, Winter Park, FL 32789

  1858 Cornell Ave, Winter Park, FL 32789
• 

  

  /5

  $2,350,000

  • Land
  • 0.55 Acre
  • $4,272,727 per Acre

  1205 Mayfield Ave, Winter Park, FL 32789

  A rare estate-sized double lot in one of Winter Park’s most coveted and established neighborhoods—Temple Heights. This expansive property offers an exceptional opportunity to build a custom luxury residence in one of Central Florida’s most sought-after locations. Nestled in a quiet, tree-lined residential pocket, this oversized parcel provides the space, privacy, and prestige rarely available in

  Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
• 

  

  /15

  $1,350 per month

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

  1695 Lee Rd Unit B210, Winter Park, FL 32789

  This great second floor one bedroom 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

  giuseppina moriconi GM SUNSHINE REALTY LLC

  1695 Lee Rd Unit B210, Winter Park, FL 32789
• 

  /2

  $228,000 Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $237,432

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  /60

  Est $1,628,824 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft

  1318 Chapman Cir, Winter Park, FL 32789

  1318 Chapman Cir, Winter Park, FL 32789
• 

  

  /37

  $824,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft

  737 N Capen Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this stunning Mid-century style 3 bedroom, 2 bath, 1930 sq ft home with a 2 car garage, where sleek modern design meets functionality. Step into the open-concept living space and be captivated by the abundance of natural light streaming through the large windows, creating a warm and inviting atmosphere. The centerpiece of this home is the gourmet

  Jenn Carlisle LPT REALTY, LLC

  737 N Capen Ave, Winter Park, FL 32789
• 

  

  /20

  $3,229 per month

  • 3 Beds
  • 2 Baths
  • 990 Sq Ft
  • Condo for Rent

  2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789

  Experience a cozy tiny-home retreat in Winter Park, a quiet neighborhood just 10 minutes from downtown Orlando and 20 minutes from Disney’s parks. Feel at home in this 4-bedroom, 2-bath home that sleeps 8.Every corner is designed for comfort, from the queen-size beds to the fully equipped kitchen with stainless steel appliances and a Keurig coffee machine. The home also features an outdoor

  2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789
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  /2

  $420,000 Sold Jan 15, 2026

  1847 Azalea Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 1,477 Sq Ft
  • Built 1961

  Last Sold Summary

  • $284/SF
  • 1 Day On Market

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  /14

  Est $557,113 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789
• 

  

  /37

  $650,000

  • 5 Beds
  • 3 Baths
  • 1,917 Sq Ft

  352 Cambridge Blvd, Winter Park, FL 32789

  This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from three separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a dedicated study. A large screened-in

  Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  352 Cambridge Blvd, Winter Park, FL 32789
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  /17

  $3,950 per month

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft
  • House for Rent

  1302 Michigan Ave, Winter Park, FL 32789

  Please visit our website at www.ORLrent.com you will find photos of our homes, tenant application, pet application, sample lease and more information. If applying for any of our homes all adult applicants over the age of 18 must submit a fully completed Application online. Application fee is $95.00 for each adult. An application reservation fee must be paid in the amount of one month's rent (in

  Mo Jabr RE/MAX 200 REALTY

  1302 Michigan Ave, Winter Park, FL 32789
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  /2

  $199,900 Sold Nov 03, 2025

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 130 Days On Market

  Current Estimated Value $192,996

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  /24

  Est $830,557 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789
• 

  

  /26

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,115 Sq Ft

  720 N Pennsylvania Ave, Winter Park, FL 32789

  Nestled in one of Winter Park’s most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern elegance with everyday comfort. From the moment you step inside, you'll be captivated by the sleek, contemporary finishes, recessed lighting, and stylish fixtures that enhance every space. The open living and dining room combo creates a bright and welcoming atmosphere, perfect for

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  720 N Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /20

  $1,650 per month

  • 1 Bed
  • 1 Bath
  • 502 Sq Ft
  • House for Rent

  1550 Michigan Ave, Winter Park, FL 32789

  Welcome to your future home in the charming district of Winter Park, FL! This inviting property offers a warm atmosphere perfect for relaxation and convenience, surrounded by a vibrant community.This residence boasts spacious living equipped with essential comforts. With ample bedrooms and bathrooms, it accommodates various lifestyles. You'll appreciate the central heating and cooling

  1550 Michigan Ave, Winter Park, FL 32789
• 

  

  /19

  $172,000 Sold May 23, 2025

  700 Melrose Ave Unit E24, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 787 Sq Ft
  • Built 1964

  Last Sold Summary

  • 14% Below List Price
  • $219/SF
  • 164 Days On Market

  Current Estimated Value $181,870

  Last Listing Agent Susan Dering HOMEVEST REALTY

  700 Melrose Ave Unit E24, Winter Park, FL 32789
• 

  

  /22

  Est $5,537,993 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,430 Sq Ft

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789
• 

  

  /29

  $439,900

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft

  1518 Pinewood Dr, Winter Park, FL 32789

  Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility.

  Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

  1518 Pinewood Dr, Winter Park, FL 32789
• 

  

  /20

  $2,800 per month

  • 2 Beds
  • 2 Baths
  • 980 Sq Ft
  • Property for Rent

  1315 Westchester Ave, Winter Park, FL 32789

  Improved Price! Wow, expect to be impressed. This home has been lovingly updated and features handscraped wood floors and tile throughout...no carpeting! In addition, there is an expansive ceiling in the living room, updated kitchen with tumbled marble backsplash, sleek appliances, granite counters and lots of wood cabinetry for storage. This home has double pane windows, updated bathrooms with

  Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  1315 Westchester Ave, Winter Park, FL 32789
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  /2

  $266,000 Sold Nov 19, 2025

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

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

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 5 Days On Market

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
• 

  /2

  Est $2,721,509 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,066 Sq Ft

  1737 Lookout Landing Cir, Winter Park, FL 32789

  1737 Lookout Landing Cir, Winter Park, FL 32789
• 

  

  /76

  $6,895,000 Pending

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
• 

  

  /27

  $1,400 per month

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

  2500 Lee Rd Unit 212, Winter Park, FL 32789

  Welcome to Lakeside Manor on beautiful Lake Killarney! This charming 2 bedroom, 1 bathroom second-floor condo offers tranquil living in one of Central Florida’s most desirable areas. Enjoy a serene, park-like setting right outside your door and access to breathtaking sunset views from the private community dock.Just minutes from Park Ave, Rollins College, Mills District, top dining,

  2500 Lee Rd Unit 212, Winter Park, FL 32789
• 

  /2

  $245,900 Sold Aug 11, 2025

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 1,132 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Below List Price
  • $217/SF
  • 2 Days On Market

  Current Estimated Value $251,206

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC

  195 Sandlewood Trail Unit 2, Winter Park, FL 32789
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  /42

  Est $703,995 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789
• 

  

  /88

  $8,500,000

  • 5 Beds
  • 6 Baths
  • 6,502 Sq Ft

  1112 Preserve Point Dr, Winter Park, FL 32789

  Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve

  Kelly Price KELLY PRICE & COMPANY LLC

  1112 Preserve Point Dr, Winter Park, FL 32789
• 

  

  /7

  $1,350 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
• 

  /2

  $725,000 Sold May 13, 2025

  1570 Grove Terrace, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft
  • Built 1991

  Last Sold Summary

  • $436/SF

  Current Estimated Value $753,158

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  1570 Grove Terrace, Winter Park, FL 32789
• 

  

  /30

  Est $738,648 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789
• 

  

  /8

  $800,000

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  1780 Bryan Ave, Winter Park, FL 32789

  Discover a truly unique offering in the heart of Winter Park! This property, located at 1780 Bryan Avenue, is being offered along with theadjoining lots at 1760 and 1770 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to purchase one, two, or all three.

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1780 Bryan Ave, Winter Park, FL 32789
• 

  

  /24

  $1,695 per month

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

  1695 Lee Rd Unit C216, Winter Park, FL 32789

  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

  1695 Lee Rd Unit C216, Winter Park, FL 32789
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  /49

  $1,650,000 Sold Mar 12, 2025

  1781 Goodrich Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,701 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $611/SF
  • 88 Days On Market

  Current Estimated Value $1,673,434

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC

  1781 Goodrich Ave, Winter Park, FL 32789
• 

  

  /30

  Est $1,335,830 Not Listed For Sale

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

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

Showing Results 121 - 160, Page 4 of 18