Winter Park, FL Homes

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  $220,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 237-3113

  225 Lewfield Cir, Winter Park, FL 32792
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  $1,550 - $3,136 per month

  Seven41 Winter Park

  Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  741 Clay St, Winter Park, FL 32789
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  $730,000 Sold Mar 23, 2026

  1213 Lindenwood Ln, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $291/SF
  • 81 Days On Market

  Current Estimated Value $726,130

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  1213 Lindenwood Ln, Winter Park, FL 32792
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  Est $316,542 Not Listed For Sale

  7319 Blue Jacket Place W, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,118 Sq Ft
  • Built 1970

  7319 Blue Jacket Place W, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $288/SF
  • 5 Days On Market

  Last Sold Price $322,000

  Last Listing Agent Jennah LeBruno, LLC RE/MAX
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  /43

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  720 W Webster Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character

  

  Vincent Cordaro

  SERHANT

  (321) 341-3712

  720 W Webster Ave, Winter Park, FL 32789
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  /18

  $2,167 per month

  • 4 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • House for Rent

  717 Denton Rd, Winter Park, FL 32792

  Winter Park 4 Bedrm Home for Rent!Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  717 Denton Rd, Winter Park, FL 32792
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  $1,590,000 Sold Mar 06, 2026

  1166 Oaks Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 2018

  Last Sold Summary

  • 12% Below List Price
  • $556/SF
  • 153 Days On Market

  Current Estimated Value $1,580,246

  Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  /6

  Est $522,059 Not Listed For Sale

  2613 Lafayette Ave, Winter Park, FL 32789

  • 2 Beds
  • Built 1956

  2613 Lafayette Ave, Winter Park, FL 32789

  Last Sold Summary

  • $586/SF
  • 148 Days On Market

  Last Sold Price $520,000

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC
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  $260,000 Pending

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER REALTY

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
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  $1,201 - $2,029 per month

  The Taylor at Winter Park

  Studio - 3 Beds

  2000 Village Ln, Winter Park, FL 32792

  5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

  2000 Village Ln, Winter Park, FL 32792
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  $245,000 Sold Jun 26, 2025

  2471 Tahoe Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $189/SF
  • 84 Days On Market

  Current Estimated Value $228,902

  Last Listing Agent Kevin Wilhelm MLSB THE BUREAU POWERED BY CAROM REALTY

  2471 Tahoe Cir, Winter Park, FL 32792
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  /19

  Not Listed For Sale

  2076 Leanne Ct, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,729 Sq Ft
  • Built 1969

  2076 Leanne Ct, Winter Park, FL 32792

  Last Sold Summary

  • $252/SF
  • 6 Days On Market

  Last Sold Price $436,000

  Last Listing Agent Julian Jackson LOKATION
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  /78

  $1,399,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,459 Sq Ft

  102 Bell Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  (321) 490-4832

  102 Bell Place, Winter Park, FL 32792
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  /16

  $1,895 per month

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

  295 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

  295 Sandlewood Trail, Winter Park, FL 32789
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  $400,000 Sold Jul 16, 2025

  3443 Arnel Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 15 Days On Market

  Current Estimated Value $388,810

  Last Listing Agent Lana More KELLER WILLIAMS WINTER PARK

  3443 Arnel Dr, Winter Park, FL 32792
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  Est $475,995 Not Listed For Sale

  1937 Eland Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1957

  1937 Eland Ave, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • $295/SF
  • 22 Days On Market

  Last Sold Price $460,000

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY
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  /54

  $424,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  1367 Tierra Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with

  Brian Bauer SOUTHERN LAND & HOMES

  1367 Tierra Cir, Winter Park, FL 32792
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  /50

  $1,499 - $2,018 per month

  Calibre Bend Apartments

  1 - 2 Beds

  3924 Calibre Bend Ln, Winter Park, FL 32792

  Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

  3924 Calibre Bend Ln, Winter Park, FL 32792
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  $1,335,000 Sold Jul 15, 2025

  1077 Minnesota Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,046 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $438/SF
  • 75 Days On Market

  Current Estimated Value $1,312,562

  Last Listing Agent Jake Johnson SHORES REAL ESTATE

  1077 Minnesota Ave, Winter Park, FL 32789
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  /2

  Est $346,624 Not Listed For Sale

  829 W New England Ave, Winter Park, FL 32789

  • 3 Beds
  • Built 1930

  829 W New England Ave, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $324/SF
  • 16 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC
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  $424,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  633 Lander Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. LOCATION, LOCATION, LOCATION! Welcome to this charming 3-bedroom, 2-bathroom home nestled in the heart of Winter Park!As you enter the home, you'll notice the living room and dining area flow seamlessly together, leading you into the kitchen featuring solid surface countertops and solid wood cabinetry. The

  Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY

  633 Lander Rd, Winter Park, FL 32792
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  $4,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,196 Sq Ft
  • House for Rent

  1091 Wildmeadow Run, Winter Park, FL 32792

  1

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  1091 Wildmeadow Run, Winter Park, FL 32792
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  $580,000 Sold Apr 21, 2025

  3006 Northwood Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Below List Price
  • $339/SF
  • 1 Day On Market

  Current Estimated Value $656,461

  Last Listing Agent Chris Creegan CREEGAN GROUP

  3006 Northwood Blvd, Winter Park, FL 32789
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  Est $1,667,650 Not Listed For Sale

  1781 Goodrich Ave, Winter Park, FL 32789

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

  1781 Goodrich Ave, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $611/SF
  • 88 Days On Market

  Last Sold Price $1,650,000

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC
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  /45

  $499,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft

  2809 Casa Aloma Way, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to 2809 Casa Aloma — a beautifully updated 3-bedroom, 2-bath charming home located on a quiet cul-de-sac in desirable Winter Park. Originally one of the subdivision’s model homes "Monaco", this property blends French Provincial design with extensive modern upgrades. Major improvements include a 2021

  Curt Marksbury WATSON REALTY CORP., REALTORS

  2809 Casa Aloma Way, Winter Park, FL 32792
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  /50

  $1,510 - $5,399 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
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  $890,000 Sold Jun 12, 2025

  1762 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $393/SF
  • 114 Days On Market

  Current Estimated Value $922,502

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1762 Mondrian Cir, Winter Park, FL 32789
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  Est $3,396,363 Not Listed For Sale

  443 Lakewood Dr, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 2,803 Sq Ft
  • Built 1954

  443 Lakewood Dr, Winter Park, FL 32789

  Last Sold Summary

  • 4% Below List Price
  • $1,267/SF
  • 0 Days On Market

  Last Sold Price $3,550,000

  Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES
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  /71

  $699,900

  • 4 Beds
  • 3 Baths
  • 2,702 Sq Ft

  3114 Heartleaf Place, Winter Park, FL 32792

  Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

  Nadia Kurakin CHAMPION HOMES

  3114 Heartleaf Place, Winter Park, FL 32792
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  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Condo for Rent

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792

  Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for

  Jacqueline Ramos JML REALTY INVESTMENTS LLC

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
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  $440,000 Sold Jan 29, 2026

  1621 Puritan Ave, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Below List Price
  • $249/SF
  • 342 Days On Market

  Current Estimated Value $440,258

  Last Listing Agent Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
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  Est $791,970 Not Listed For Sale

  1375 Suffolk Rd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft
  • Built 1940

  1375 Suffolk Rd, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $292/SF
  • 30 Days On Market

  Last Sold Price $745,000

  Last Listing Agent Beth Hobart MAINFRAME REAL ESTATE
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  $195,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2924 Antique Oaks Cir Unit 46, Winter Park, FL 32792

  Discover a charming 2nd-story condo nestled in the desirable Parkview Village community of Winter Park. This spacious home features two bedrooms and two bathrooms across 1,105 square feet of thoughtfully designed living space. The interior boasts large rooms, providing ample space for comfort and versatility. Admire the vaulted ceilings that enhance the open and airy atmosphere, while the

  Donna Layton CENTURY 21 EDGE

  2924 Antique Oaks Cir Unit 46, Winter Park, FL 32792
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  $1,172 - $3,702 per month

  Liv at Winter Park Apartment Homes

  Studio - 3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  4755 N Goldenrod Rd, Winter Park, FL 32792
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  $1,088,000 Sold Jan 30, 2026

  1092 Wading Waters Cir, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,057 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $356/SF
  • 60 Days On Market

  Current Estimated Value $1,103,120

  Last Listing Agent Tara Haefner KELLER WILLIAMS HERITAGE REALTY

  1092 Wading Waters Cir, Winter Park, FL 32792
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  /23

  Est $217,404 Not Listed For Sale

  2494 Timberline Dr, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  2494 Timberline Dr, Winter Park, FL 32792

  Last Sold Summary

  • 9% Below List Price
  • $182/SF
  • 11 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Jeff Jones Mark Spain
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  /34

  $579,999

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

  330 Elkhorn Ct, Winter Park, FL 32792

  330 Elkhorn Ct is a beautifully renovated, move-in-ready home located in the highly desired Winter Park Pines community. Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  330 Elkhorn Ct, Winter Park, FL 32792
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  $3,300 per month

  • 2 Beds
  • 2 Baths
  • 1,209 Sq Ft
  • House for Rent

  870 Carver St Unit A, Winter Park, FL 32789

  Welcome to 870 Carver Street, a thoughtfully designed two-bedroom, two-bath residence in the core of Winter Park. Offering more than 1,200 square feet, the newly constructed home features vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork that define its architectural character. The primary suite includes a floating wall closet system, a laundry

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  870 Carver St Unit A, Winter Park, FL 32789
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  $420,000 Sold May 06, 2025

  627 Carvell Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Below List Price
  • $312/SF
  • 152 Days On Market

  Current Estimated Value $407,552

  Last Listing Agent Ray Al-Malt EXP REALTY LLC

  627 Carvell Dr, Winter Park, FL 32792
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  Est $344,225 Not Listed For Sale

  1880 Viburnum Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1961

  1880 Viburnum Ln, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $308/SF
  • 132 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

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