Winter Park, FL Homes

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  $399,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,755 Sq Ft

  2232 Shadowland Loop, Winter Park, FL 32792

  Welcome to this fabulous townhome in the much sought after Hawk's Crest neighborhood in winter park. The townhouse has perfect layout when you walk into the house, beautiful tile floor, one half bathroom downstairs. 3 Bedrooms upstairs with a big loft. It is a perfect floor plan to live here or as an investment. Resort style pool and playground. Near to everywhere, easy to find highway and

  He Gao U S GLORY REALTY

  2232 Shadowland Loop, Winter Park, FL 32792
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  $1,695 - $1,825 per month

  The Lofts of Winter Park Village

  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

  520 N Orlando Ave, Winter Park, FL 32789
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  $426,000 Sold Jul 03, 2025

  2028 Sussex Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 1973

  Last Sold Summary

  • 6% Below List Price
  • $254/SF
  • 39 Days On Market

  Current Estimated Value $427,581

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  2028 Sussex Rd, Winter Park, FL 32792
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  Est $557,876 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

  Last Listing Agent nicoletta buonaccordo ALTIS REALTY
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  $1,050,000 Open Sat 12AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,907 Sq Ft

  1836 Grinnell Terrace, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Beautifully renovated home in the heart of highly desirable Winter Park, surrounded by multi-million-dollar properties. Move-in ready and thoughtfully updated throughout. Set on an expansive lot approximately 79 x 152 (11,305 square feet) provides plenty of space to build your future dream home! This light-filled home features wide-plank flooring,

  Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

  1836 Grinnell Terrace, Winter Park, FL 32789
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  $6,750 per month

  • 4 Beds
  • 3.5 Baths
  • 3,276 Sq Ft
  • House for Rent

  527 Langholm Dr, Winter Park, FL 32789

  Beautiful custom home with an open floor plan featuring 4 bedrooms, 3.5 baths, downstairs office, 2 car garage, huge loft for gaming and an additional private Bonus Room that can be utilized as a gym or flex room. Master Bedroom and office are conveniently located on the first floor. Additional features of this home include a gourmet kitchen with island, stainless steel appliances, granite

  Nancy Woodruff WOODRUFF REALTY, INC.

  527 Langholm Dr, Winter Park, FL 32789
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  $4,772,500 Sold Sep 18, 2025

  765 Via Lugano, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,319 Sq Ft
  • Built 2019

  Last Sold Summary

  • $1,105/SF
  • 1 Day On Market

  Current Estimated Value $4,664,184

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  765 Via Lugano, Winter Park, FL 32789
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  Est $782,132 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

  Last Listing Agent Tyler Reik KELLER WILLIAMS WINTER PARK
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  $1,050,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,342 Sq Ft

  632 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards

  Kristin Duncan KELLER WILLIAMS ADVANTAGE REALTY

  632 Country Club Dr, Winter Park, FL 32789
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  $1,449 - $1,761 per month

  POSTE Winter Park

  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

  800 Semoran Park Dr, Winter Park, FL 32792
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  $3,100,000 Sold Jun 27, 2025

  731 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,260 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 45 Days On Market

  Current Estimated Value $2,941,576

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
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  Est $241,877 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

  • 18% Below List Price
  • $222/SF
  • 10 Days On Market

  Last Sold Price $294,000

  Last Listing Agent William Grim, III RE/MAX
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  /31

  $214,995

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  4790 Tangerine Ave Unit 4790, Winter Park, FL 32792

  Move right into this beautifully two-bedroom, two-bath condominium located in desirable East Winter Park. The thoughtfully designed floor plan offers two spacious bedrooms, and bathrooms—one featuring a tub and the other a shower—providing comfort and privacy.The light-filled great room showcases attractive laminate wood flooring and sliding glass doors that open to a private, screened-in

  Sonny Manku SUNSHINE BROKERAGE, LLC

  4790 Tangerine Ave Unit 4790, Winter Park, FL 32792
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  $2,490 per month

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Townhouse for Rent

  7494 Aloma Pines Ct, Winter Park, FL 32792

  *1st Month HALF OFF* if you apply before March 31st ! Desirable 3-bed, 2.5-bath townhome in a gated community just minutes from Downtown Winter Park, UCF and Orlando. Prime location near top-rated schools, parks, dining, shopping, and major employers with easy access to I-4 and SunRail for effortless commuting. Winter Park blends relaxed neighborhood living with urban convenience and highly

  Krys Guillaume CENTURY 21 CARIOTI

  7494 Aloma Pines Ct, Winter Park, FL 32792
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  $288,000 Sold Apr 08, 2025

  1811 Winter Green Blvd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Built 1994

  Last Sold Summary

  • 9% Below List Price
  • $243/SF
  • 204 Days On Market

  Current Estimated Value $295,067

  Last Listing Agent GREGORY BLACKALL VERANDA REALTY GROUP

  1811 Winter Green Blvd, Winter Park, FL 32792
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  Est $325,262 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

  Last Listing Agent Tamara Mazo Ferro COLDWELL BANKER REALTY
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  $1,149,000

  • 4 Beds
  • 3.5 Baths
  • 3,153 Sq Ft

  2922 Reef Knot Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Incredible Value!!! Major price reduction! Private Lakefront Living! Move-in Ready! Wake up to water views, quiet mornings and the kind of lifestyle that rarely becomes available in the Winter Park/Howell Branch area. Set along the shores of a private ski lake- Lake Florence, this single-level lakefront residence offers a serene retreat within an

  Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

  2922 Reef Knot Place, Winter Park, FL 32792
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  $1,750 - $2,750 per month

  Hannibal Square

  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,

  433 W New England Ave, Winter Park, FL 32789
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  $2,700,000 Sold Oct 02, 2025

  1445 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,489 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $601/SF
  • 2 Days On Market

  Current Estimated Value $2,652,725

  Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

  1445 Holts Grove Cir, Winter Park, FL 32789
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  Est $5,368,342 Not Listed For Sale

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

  • 4 Beds
  • 4.5 Baths
  • 5,430 Sq Ft
  • Built 2005

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

  Last Sold Summary

  • 10% Below List Price
  • $1,104/SF
  • 0 Days On Market

  Last Sold Price $5,995,000

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
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  $225,000

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft

  3371 River View Way Unit 46, Winter Park, FL 32792

  Great location, perfect for first time buyers in the Hidden Oaks community. The unit offers three bedrooms (all upstairs), two full bathrooms (upstairs) and one half bathroom (downstairs), two reserved parking spots. Close proximity to Full Sail University, the University of Central Florida and Valencia College as well as many major Central Florida employers. More pictures coming soon.....

  Romesh Panchal ROBERT SLACK LLC

  3371 River View Way Unit 46, Winter Park, FL 32792
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  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Townhouse for Rent

  307 Sandlewood Trail, Winter Park, FL 32789

  This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  307 Sandlewood Trail, Winter Park, FL 32789
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  $375,000 Sold Dec 30, 2025

  3083 Crane Strand Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1972

  Last Sold Summary

  • $312/SF
  • 12 Days On Market

  Current Estimated Value $369,801

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  3083 Crane Strand Dr, Winter Park, FL 32792
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  Est $2,754,843 Not Listed For Sale

  1737 Lookout Landing Cir, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 5,066 Sq Ft
  • Built 2013

  1737 Lookout Landing Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $533/SF
  • 232 Days On Market

  Last Sold Price $2,699,999

  Last Listing Agent Amy Wilson KELLER WILLIAMS REALTY AT THE PARKS
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  $199,130

  • 1 Bed
  • 1 Bath
  • 753 Sq Ft

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792

  Stunning renovated 1-bedroom in Winter Park! Enjoy all-new flooring, fresh paint, knockdown ceilings, and a sleek bath and kitchen with new cabinets and stainless appliances. Fully furnished—just bring your toothbrush. Community was freshly painted and roads repaved in 2025. Prime location near top dining, shopping, and parks. Move-in ready perfection!

  Christopher Franqui PROPERTY OUTLET INTERNATIONAL

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792
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  $1,300 - $1,855 per month

  La Aloma

  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

  3040 Aloma Ave, Winter Park, FL 32792
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  $560,000 Sold Aug 20, 2025

  1901 Loch Berry Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Below List Price
  • $394/SF
  • 7 Days On Market

  Current Estimated Value $541,517

  Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

  1901 Loch Berry Rd, Winter Park, FL 32792
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  Est $193,754 Not Listed For Sale

  200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792

  Last Sold Summary

  • 16% Below List Price
  • $206/SF
  • 35 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Robin Delaney KELLER WILLIAMS ADVANTAGE III
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  $360,000

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  1552 Florentino Ln, Winter Park, FL 32792

  BACK ON THE MARKET, BUYERS FINANCING FELL THROUGH! Welcome to this beautifully upgraded corner townhome located in the desirable gated community of VISTAS AT LAKE HOWELL in Winter Park, Seminole County. This spacious residence offers 1,682 sq ft under air (2,861 sq ft total), built in 2004, with 3 bedrooms and 2.5 baths, and is perfectly positioned on a corner lot for added privacy and natural

  Nohora Gomez COLDWELL BANKER REALTY

  1552 Florentino Ln, Winter Park, FL 32792
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  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, Winter Park, FL 32789
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  $916,000 Sold Jul 17, 2025

  609 Langholm Dr, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $462/SF
  • 8 Days On Market

  Current Estimated Value $915,881

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  Est $686,657 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1960

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

  Last Sold Summary

  • 2% Below List Price
  • $445/SF
  • 75 Days On Market

  Last Sold Price $700,000

  Last Listing Agent Scott Garstka CHARLES RUTENBERG REALTY ORLANDO
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  $1,200,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,837 Sq Ft

  244 Osceola Ct, Winter Park, FL 32789

  Under contract-accepting backup offers. Set in one of Winter Park’s most sought-after locations, this 1940 home delivers something that’s hard to recreate: walkability, character, and flexibility. Just steps from Downtown Winter Park, iconic Park Avenue, and Rollins College, with private access to Lake Osceola, the location alone sets this property apart. The home offers the charm of a historic

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  244 Osceola Ct, Winter Park, FL 32789
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  $1,049 - $1,757 per month

  Carlton Arms of Winter Park

  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.

  300 Jamestown Dr, Winter Park, FL 32792
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  $660,000 Sold Nov 17, 2025

  2421 Summerfield Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1968

  Last Sold Summary

  • 2% Above List Price
  • $293/SF
  • 6 Days On Market

  Current Estimated Value $647,960

  Last Listing Agent Simi Lakhani KELLER WILLIAMS CLASSIC

  2421 Summerfield Rd, Winter Park, FL 32792
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  Est $236,478 Not Listed For Sale

  5498 Peaco Place, Winter Park, FL 32792

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft
  • Built 1985

  5498 Peaco Place, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $243/SF
  • 39 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Christina Rordam FLORIDA REALTY INVESTMENTS
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  $195,000

  • 3 Beds
  • 2 Baths
  • 1,117 Sq Ft

  3217 Oak Lawn Place Unit 211, Winter Park, FL 32792

  3-bedroom, 2-bath second-floor corner unit in the Hidden Oaks community in Winter Park. The functional floor plan offers a spacious living area with windows on three sides, filling the home with natural light. The kitchen includes a brand-new range, while the refrigerator, dishwasher, and washer/dryer were replaced approximately 3 years ago. Conveniently located near Full Sail University, UCF,

  Abby Yelken SHORES REAL ESTATE

  3217 Oak Lawn Place Unit 211, Winter Park, FL 32792
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  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • House for Rent

  1815 Barker Dr, Winter Park, FL 32789

  Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals,

  Benjamin Cole, IV SOTERA LIVING

  1815 Barker Dr, Winter Park, FL 32789
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  $498,000 Sold May 28, 2025

  808 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1961

  Last Sold Summary

  • $286/SF
  • 4 Days On Market

  Current Estimated Value $488,169

  Last Listing Agent Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

  808 Denton Rd, Winter Park, FL 32792
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  Est $755,652 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 1960

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

  Last Sold Summary

  • 18% Above List Price
  • $380/SF
  • 0 Days On Market

  Last Sold Price $640,000

  Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES

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