Winter Park, FL Homes

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  $1,925,000

  • 4 Beds
  • 4 Baths
  • 2,653 Sq Ft

  721 Pansy Ave, Winter Park, FL 32789

  Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  721 Pansy Ave, Winter Park, FL 32789
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  /18

  $1,330 - $1,750 per month

  Park East - Park Knowles Apartments

  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

  311 N Knowles Ave, Winter Park, FL 32789
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  $360,000 Sold Apr 30, 2025

  1493 Hyde Park Dr, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • Built 1989

  Last Sold Summary

  • 1% Above List Price
  • $256/SF
  • 4 Days On Market

  Current Estimated Value $355,232

  Last Listing Agent Erica Diaz HOMEVEST REALTY

  1493 Hyde Park Dr, Winter Park, FL 32792
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  /43

  Est $1,778,783 Not Listed For Sale

  1809 Harland Park Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft
  • Built 2014

  1809 Harland Park Dr, Winter Park, FL 32789

  Last Sold Summary

  • 15% Above List Price
  • $423/SF
  • 8 Days On Market

  Last Sold Price $1,550,000

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC
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  /47

  $1,100,000

  • 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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  /16

  $1,850 per month

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Townhouse for Rent

  609 Montego Bay Ct Unit 609, Winter Park, FL 32792

  2-bedroom, 2-bathroom townhome. Near to shopping malls and Sail University

  Jose Rodriguez JOSE ORLANDO RODRIGUEZ

  609 Montego Bay Ct Unit 609, Winter Park, FL 32792
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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 $367,544

  Last Listing Agent Bob Paulson COLDWELL BANKER REALTY

  1041 Manchester Cir, Winter Park, FL 32792
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  /2

  Est $1,875,506 Not Listed For Sale

  1411 Border Dr, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 4,638 Sq Ft
  • Built 2019

  1411 Border Dr, Winter Park, FL 32789

  Last Sold Summary

  • 11% Above List Price
  • $364/SF
  • 195 Days On Market

  Last Sold Price $1,690,000

  Last Listing Agent Ana Scarlato CORCORAN PREMIER REALTY
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  /20

  $205,000

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

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

  This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

  Manny Celi YOUNG REAL ESTATE

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
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  /16

  $1,699 - $1,824 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  *Restricted units only*App and Admin special for only $175!Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will

  4704 Lucier Ct, Winter Park, FL 32792
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  $550,000 Sold May 08, 2025

  2906 Rapidan Trail, Winter Park, FL 32789

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

  Last Sold Summary

  • $236/SF
  • 4 Days On Market

  Current Estimated Value $620,188

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2906 Rapidan Trail, Winter Park, FL 32789
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  Est $854,896 Not Listed For Sale

  436 W Swoope Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft
  • Built 2014

  436 W Swoope Ave, Winter Park, FL 32789

  Last Sold Summary

  • 10% Above List Price
  • $298/SF
  • 170 Days On Market

  Last Sold Price $775,000

  Last Listing Agent Delora Credle COLDWELL BANKER REALTY
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  /25

  $209,900 Open Sat 11AM - 2PM

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

  4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

  Charming Updated Home in Prime Winter Park Location Welcome to this beautifully updated home located in the highly desirable area of Winter Park. Combining comfort, style, and convenience, this property offers a thoughtfully designed open floor plan that creates a seamless flow between the main living spaces, making it ideal for both everyday living and entertaining. The home features two

  Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

  4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
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  /16

  $1,350 per month

  • 1 Bath
  • 549 Sq Ft
  • Apartment for Rent

  3035 George Mason Ave Unit 19, Winter Park, FL 32792

  Fully renovated studio in Winter Park FL! Accept immigrant applications. This is an individual studio, and there are only 4 units per block in the condominium. Great location close to Costco, Sams, and 408 exit. There is a supermarket in the plaza next door and walking distance for quick shopping. This unit is a studio and its equipped with semi-new appliances like washer/dryer, refrigerator,

  Morgana Sasso FRIENDS REALTY LLC

  3035 George Mason Ave Unit 19, 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 $737,384

  Last Listing Agent Catherine Williams COLDWELL BANKER REALTY

  2955 Lolissa Ln, Winter Park, FL 32789
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  /33

  Est $608,970 Not Listed For Sale

  5319 Pine Lily Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,265 Sq Ft
  • Built 2015

  5319 Pine Lily Cir, Winter Park, FL 32792

  Last Sold Summary

  • $269/SF
  • 14 Days On Market

  Last Sold Price $610,000

  Last Listing Agent Donnie Garland, Jr ERA GRIZZARD REAL ESTATE
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  /36

  $960,000

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft

  1521 Heron Wood Place, Winter Park, FL 32792

  Rare opportunity to own an established daycare operating from two structures on the same parcel, offered together with the real estate. The business currently provides immediate income for a hands-on owner or family-run operation.One structure is currently utilized for daycare operations, while the second structure is a single-family home that offers excellent potential for future daycare

  Ronald Trotter RE/MAX INNOVATION

  1521 Heron Wood Place, Winter Park, FL 32792
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  /14

  $1,250 - $1,800 per month

  Park Apartments

  1 - 3 Beds

  7528 Park Promenade Dr, Winter Park, FL 32792

  WELCOME TO THE PARK APARTMENTS (NEWLY RENOVATED!) Come join us in prestigious Winter Park. You will know as soon as you stroll down the beautiful lined drive, through the gates that you are in a distinctive community. We have five unique apartment floor plans to choose from, each with designer touches. the community has lush landscaping filled with many amenities. relax by either of the two

  7528 Park Promenade 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 $2,243,307

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  521 S Phelps Ave, Winter Park, FL 32789
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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

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY
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  /39

  $925,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,017 Sq Ft

  667 Dunblane Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. An entertainer’s dream in the heart of Winter Park, just minutes from Park Avenue, this impeccably renovated residence in the highly desirable Kenilworth Shores community offers true turn-key luxury. Enjoy utilities and water provided by the City of Winter Park, known for some of the lowest utility rates in Florida, along with underground power lines for

  Paola Padovan PADOVAN REALTY CORP.

  667 Dunblane Dr, Winter Park, FL 32792
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  /13

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft
  • House for Rent

  2743 Sanbina St, Winter Park, FL 32789

  Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights:-Primary suite featuring a walk-in closet and private ensuite bathroom-Classic terrazzo flooring-Recently remodeled

  Summer Hornburg BELMONT REALTY

  2743 Sanbina St, Winter Park, FL 32789
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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 $429,755

  Last Listing Agent Heather Kolin PALMANO GROUP RE BROKERAGE LLC

  2003 Bentwood Dr, Winter Park, FL 32792
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  /31

  Est $177,005 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

  • 21% Below List Price
  • $218/SF
  • 16 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Maureen Golmont WATSON REALTY CORP
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  /11

  $198,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez WF REALTY CORP.

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
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  /11

  $1,061 - $1,470 per month

  Solis at Winter Park

  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

  7502 Sun Key Blvd, Winter Park, FL 32792
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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 $444,416

  Last Listing Agent Denise Korrey KORR REALTY CORP

  2151 Conifer Ave, Winter Park, FL 32792
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  Est $1,652,755 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

  • 3% Above List Price
  • $519/SF
  • 162 Days On Market

  Last Sold Price $1,612,000

  Last Listing Agent Lance Kotowski Properties By Lanko, Inc
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  $189,999

  • 2 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  7468 Canford Ct Unit 24, Winter Park, FL 32792

  This charming 2-bedroom, 1.5-bath condo offers a desirable townhome-style layout with spacious living areas and thoughtful storage throughout. The community features deluxe vinyl fencing installed by the HOA, along with a clubhouse and a community pool, providing great amenities for residents to enjoy. Inside, you’ll find the convenience of an in-unit washer and dryer combo, ample storage under

  Javier Albelo Rivera EMPIRE NETWORK REALTY

  7468 Canford Ct Unit 24, Winter Park, FL 32792
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  /18

  $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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  $290,000 Sold Nov 24, 2025

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,004 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $289/SF
  • 54 Days On Market

  Current Estimated Value $284,375

  Last Listing Agent Maria Elena Perez MEP REALTY INVESTMENTS LLC

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792
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  Est $288,811 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

  • 2% Below List Price
  • $283/SF
  • 1 Day On Market

  Last Sold Price $295,000

  Last Listing Agent GREGORY NOONE CHARLES RUTENBERG REALTY ORLANDO
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  /46

  $1,010,000 Pending

  • 3 Beds
  • 3 Baths
  • 1,615 Sq Ft

  456 Carolina Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience the FLAGSHIP LIFESTYLE of Winter Park, where COASTAL INSPIRATION MEETS TIMELESS CHARM. This beautiful 3-bedroom, 3-bath residence offers a thoughtfully designed floor plan with inviting living spaces downstairs and all bedrooms upstairs for added privacy. Built in 2004 with solid concrete block

  Heather Frazee FANNIE HILLMAN & ASSOCIATES

  456 Carolina Ave, Winter Park, FL 32789
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  /29

  $1,230 - $1,792 per month

  Atlas at Winter Park

  1 - 3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  $330,000 Sold May 09, 2025

  992 Carnation Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $330/SF
  • 57 Days On Market

  Current Estimated Value $330,943

  Last Listing Agent Bianca Botelho RE/MAX ASSURED

  992 Carnation Dr, Winter Park, FL 32792
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  Est $190,218 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% Above List Price
  • $193/SF
  • 61 Days On Market

  Last Sold Price $184,000

  Last Listing Agent Hojin Chang RE/MAX
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  /15

  $219,900

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7771 Country Place Unit 7, Winter Park, FL 32792

  Motivated Seller....Fantastic 3-Bedroom, 2-Bathroom Condo Located in the Highly Desirable Winter Park Area! This Home Features an Open Galley Kitchen with a High Vaulted Ceiling and a Convenient Pantry. The Spacious Living/Dining Room Combination Also Boasts Vaulted Ceilings and Fills with Natural Light Through the Sliding Glass Doors, Creating an Inviting Yet Cozy Atmosphere. Beautiful Laminate

  Ivan Tobon OUTLET REALTY

  7771 Country Place Unit 7, Winter Park, FL 32792
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  /21

  $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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  $580,000 Sold May 16, 2025

  1392 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2008

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 123 Days On Market

  Current Estimated Value $546,613

  Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

  1392 Indiana Ave, Winter Park, FL 32789
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  Est $1,827,197 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

  • 22% Below List Price
  • $594/SF
  • 0 Days On Market

  Last Sold Price $2,350,000

  Last Listing Agent Chocky Burks CORCORAN PREMIER REALTY

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