Winter Park, FL Homes

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  $624,000

  • 3 Beds
  • 3 Baths
  • 1,620 Sq Ft

  1822 Yorkshire Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect for modern living. Enjoy the

  MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

  1822 Yorkshire Dr, Winter Park, FL 32792
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  $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
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  $675,000 Sold Mar 16, 2026

  620 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,075 Sq Ft
  • Built 1967

  Last Sold Summary

  • 9% Below List Price
  • $325/SF
  • 14 Days On Market

  Current Estimated Value $685,965

  Last Listing Agent Jason Asa LPT REALTY, LLC

  620 Darcey Dr, Winter Park, FL 32792
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  Not Listed For Sale

  700 Melrose Ave Unit G, Winter Park, FL 32789

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

  700 Melrose Ave Unit G, Winter Park, FL 32789

  Last Sold Summary

  • $281/SF
  • 73 Days On Market

  • Last Sold Price $193,000
  • Jul 29, 2024

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY
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  /41

  $554,900

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft

  330 Elkhorn Ct, Winter Park, FL 32792

  330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  330 Elkhorn Ct, Winter Park, FL 32792
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  /11

  Starting at $1,340

  Total Monthly Price

  • 1 - 2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  Solis at Winter Park

  (321) 399-2988

  

  7502 Sun Key Blvd, Winter Park, FL 32792
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  $315,000 Sold Jan 01, 2026

  615 Warrenton Rd, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,221 Sq Ft
  • Built 1984

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 50 Days On Market

  Current Estimated Value $314,197

  Last Listing Agent Bryan Burns RE/MAX DOWNTOWN

  615 Warrenton Rd, Winter Park, FL 32792
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  /31

  Est $185,873 Not Listed For Sale

  3307 Amber Wood Way Unit 106, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1983

  3307 Amber Wood Way Unit 106, Winter Park, FL 32792

  Last Sold Summary

  • 17% Below List Price
  • $218/SF
  • 16 Days On Market

  • Last Sold Price $225,000
  • Nov 30, 2023

  Last Listing Agent Maureen Golmont WATSON REALTY CORP
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  /22

  $458,990 Pending

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft

  2020 Cocos Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Beautifully renovated pool home in the highly desirable Eastbrook community of Winter Park, featuring major recent upgrades including a new AC system, windows, doors, and flooring throughout the home. This move-in ready 3-bedroom, 2-bath residence sits on an oversized 0.30-acre corner lot in a quiet cul-de-sac

  Julimar Barreiro Pastrana SERHANT

  2020 Cocos Ct, Winter Park, FL 32792
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  /29

  Starting at $1,149

  Total Monthly Price

  • 1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  Atlas at Winter Park

  (689) 219-8922

  

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  $325,000 Sold Dec 30, 2025

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Below List Price
  • $280/SF
  • 6 Days On Market

  Current Estimated Value $329,134

  Last Listing Agent Lisa Gould KELLER WILLIAMS WINTER PARK

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  Est $1,629,069 Not Listed For Sale

  1318 Chapman Cir, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,105 Sq Ft
  • Built 2014

  1318 Chapman Cir, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $519/SF
  • 162 Days On Market

  • Last Sold Price $1,612,000
  • Feb 23, 2024

  Last Listing Agent Lance Kotowski Properties By Lanko, Inc
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  $1,275,000

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  1651 Westchester Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome

  Shawn Layton SERHANT

  1651 Westchester Ave, Winter Park, FL 32789
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  /31

  Starting at $1,695 Per Month

  • 1 Bed

  520 N Orlando Ave, Winter Park, FL 32789

  Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

  The Lofts of Winter Park Village

  (321) 340-6757

  520 N Orlando Ave, Winter Park, FL 32789
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  $790,000 Sold Jun 05, 2025

  600 Brechin Dr, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,360 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $335/SF
  • 12 Days On Market

  Current Estimated Value $771,408

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  600 Brechin Dr, Winter Park, FL 32792
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  Est $284,597 Not Listed For Sale

  5774 Shale Ct, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft
  • Built 1985

  5774 Shale Ct, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $283/SF
  • 1 Day On Market

  • Last Sold Price $295,000
  • Oct 20, 2023

  Last Listing Agent GREGORY NOONE CHARLES RUTENBERG REALTY ORLANDO
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  /17

  $489,990

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  501 Heritage Blvd, Winter Park, FL 32792

  Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

  Bernardo Carrasquel B EXP REALTY LLC

  501 Heritage Blvd, Winter Park, FL 32792
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  /31

  Starting at $1,515 Per Month

  • 1 - 2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  POSTE Winter Park

  (321) 415-7565

  

  800 Semoran Park Dr, Winter Park, FL 32792
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  $517,000 Sold Nov 07, 2025

  1628 Lawndale Cir, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft
  • Built 1984

  Last Sold Summary

  • 6% Below List Price
  • $301/SF
  • 6 Days On Market

  Current Estimated Value $523,611

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  1628 Lawndale Cir, Winter Park, FL 32792
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  Est $177,791 Not Listed For Sale

  229 Lewfield Cir Unit 229, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft
  • Built 1973

  229 Lewfield Cir Unit 229, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $193/SF
  • 61 Days On Market

  • Last Sold Price $184,000
  • Jul 01, 2024

  Last Listing Agent Hojin Chang RE/MAX
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  /75

  $2,095,000 Pending

  • 3 Beds
  • 4.5 Baths
  • 5,138 Sq Ft

  2820 Bear Island Pointe, Winter Park, FL 32792

  Under contract-accepting backup offers. Tucked behind the gates of Cypress Reserve, this stunning custom-built lakefront home sits on 110 feet of private waterfront along the serene shores of Bear Gully Lake. Inspired by a featured Southern Living plan and thoughtfully expanded, the home blends timeless architecture with generous, well-appointed living spaces — all framed by panoramic water

  Kelly Price KELLY PRICE & COMPANY LLC

  2820 Bear Island Pointe, Winter Park, FL 32792
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  Starting at $1,750 Per Month

  • 2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  Hannibal Square

  (689) 207-6504

  

  433 W New England Ave, Winter Park, FL 32789
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  $351,000 Sold Sep 09, 2025

  1041 Manchester Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • Built 1977

  Last Sold Summary

  • 16% Below List Price
  • $209/SF
  • 147 Days On Market

  Current Estimated Value $371,122

  Last Listing Agent Bob Paulson COLDWELL BANKER REALTY

  1041 Manchester Cir, Winter Park, FL 32792
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  Est $1,818,883 Not Listed For Sale

  1433 Sarazens Place, Winter Park, FL 32792

  • 5 Beds
  • 5.5 Baths
  • 3,954 Sq Ft
  • Built 2020

  1433 Sarazens Place, Winter Park, FL 32792

  Last Sold Summary

  • 23% Below List Price
  • $594/SF
  • 0 Days On Market

  • Last Sold Price $2,350,000
  • Apr 17, 2024

  Last Listing Agent Chocky Burks CORCORAN PREMIER REALTY
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  $670,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,304 Sq Ft

  2713 Eastern Pkwy, Winter Park, FL 32789

  Welcome to this charming, meticulously maintained 3-bedroom, 2-bath residence in the heart of Winter Park—lovingly cared for by the same owner for over 30 years. This home reflects true pride of ownership with thoughtful updates and improvements that provide both comfort and peace of mind. Enjoy entertaining in the spacious eat in kitchen with full Stainless appliance package. Outdoor living

  Helen Thompson RE/MAX SELECT GROUP

  2713 Eastern Pkwy, Winter Park, FL 32789
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  Starting at $1,300 Per Month

  • 1 - 3 Beds

  3040 Aloma Ave, Winter Park, FL 32792

  La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

  La Aloma

  (689) 207-3431

  3040 Aloma Ave, Winter Park, FL 32792
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  $720,000 Sold Jan 20, 2026

  2955 Lolissa Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,538 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $204/SF
  • 47 Days On Market

  Current Estimated Value $742,021

  Last Listing Agent Catherine Williams COLDWELL BANKER REALTY

  2955 Lolissa Ln, Winter Park, FL 32789
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  Est $556,063 Not Listed For Sale

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft
  • Built 2006

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $303/SF
  • 0 Days On Market

  • Last Sold Price $550,000
  • May 03, 2024

  Last Listing Agent nicoletta buonaccordo ALTIS REALTY
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  /20

  $400,000

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  2482 Roxbury Rd, Winter Park, FL 32789

  Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready.But what truly sets this property apart is the location and land. With

  Gary Cohl COLDWELL BANKER REALTY

  2482 Roxbury Rd, Winter Park, FL 32789
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  Starting at $1,015 Per Month

  • Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  Carlton Arms of Winter Park is a well established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff. We offer an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  Carlton Arms of Winter Park

  (689) 220-7887

  

  300 Jamestown Dr, Winter Park, FL 32792
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  $2,285,000 Sold Nov 19, 2025

  521 S Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 3,883 Sq Ft
  • Built 2015

  Last Sold Summary

  • 7% Below List Price
  • $588/SF
  • 118 Days On Market

  Current Estimated Value $2,223,005

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  521 S Phelps Ave, Winter Park, FL 32789
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  Est $787,373 Not Listed For Sale

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

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Built 2004

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

  Last Sold Summary

  • $401/SF
  • 280 Days On Market

  • Last Sold Price $785,000
  • Jun 16, 2023

  Last Listing Agent Tyler Reik KELLER WILLIAMS WINTER PARK
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  $2,295,000

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft

  1760 Legion Dr, Winter Park, FL 32789

  Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
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  /20

  Starting at $1,383 Per Month

  • 1 - 2 Beds

  3250 Bishop Park Dr, Winter Park, FL 32792

  Your home oasis awaits at ARIUM Winter Park with our upscale amenities and open-concept 1 and 2-bedroom apartments for rent. Minutes from downtown Winter Park and Orlando's hot spots, our community provides the perfect place to call home.Soak up the sun at our resort-style pool and outdoor kitchen, de-stress in our fitness center, or bring your canine companion to explore our dog

  ARIUM Winter Park

  (321) 346-5593

  

  3250 Bishop Park Dr, Winter Park, FL 32792
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  $430,000 Sold Jul 25, 2025

  2003 Bentwood Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,675 Sq Ft
  • Built 1981

  Last Sold Summary

  • 1% Above List Price
  • $257/SF
  • 16 Days On Market

  Current Estimated Value $440,434

  Last Listing Agent Heather Kolin PALMANO GROUP RE BROKERAGE LLC

  2003 Bentwood Dr, Winter Park, FL 32792
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  Est $255,760 Not Listed For Sale

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

  Last Sold Summary

  • 13% Below List Price
  • $222/SF
  • 10 Days On Market

  • Last Sold Price $294,000
  • May 21, 2024

  Last Listing Agent William Grim, III RE/MAX
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  $265,000

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft

  2401 Sun Valley Cir, Winter Park, FL 32792

  Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and

  Jamie Vanosdol EXP REALTY LLC

  2401 Sun Valley Cir, Winter Park, FL 32792
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  /12

  Starting at $3,350 Per Month

  • 2 Beds

  1894 Demetree Dr, Winter Park, FL 32789

  Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter ParkWelcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals.This thoughtfully

  Waterbridge Subdivision

  (844) 871-1098

  1894 Demetree Dr, Winter Park, FL 32789
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  $450,000 Sold Aug 28, 2025

  2151 Conifer Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $249/SF
  • 32 Days On Market

  Current Estimated Value $454,765

  Last Listing Agent Denise Korrey KORR REALTY CORP

  2151 Conifer Ave, Winter Park, FL 32792
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  Est $325,072 Not Listed For Sale

  4870 Seminole Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1957

  4870 Seminole Ave, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $317/SF
  • 32 Days On Market

  • Last Sold Price $335,000
  • May 30, 2024

  Last Listing Agent Tamara Mazo Ferro COLDWELL BANKER REALTY

Showing Results 121 - 160, Page 4 of 18