Winter Springs, FL Homes

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  $499,000

  $50K PRICE DROP Under Contract

  • 4 Beds
  • 2.5 Baths
  • 1,922 Sq Ft

  440 Buckskin Ct, Winter Springs, FL 32708

  Under contract-accepting backup offers. PAID-OFF SOLAR + 2018 ROOF + WHOLE-HOME 10Gb ETHERNET all on a corner lot in the heart of Winter Springs!Welcome to 440 Buckskin Court, a 4-bedroom, 2.5-bath home in the established Deer Run community with the kind of character and charm you do not find in your average Florida home. Set on a spacious corner lot with fresh landscaping and a brand-new

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  440 Buckskin Ct, Winter Springs, FL 32708
• Explore Winter Springs

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  /8

  $1,975 Per Month

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • House for Rent

  213 Buttonwood Ave, Winter Springs, FL 32708

  This charming 3-bedroom, 2-bath home offers 1,232 square feet of comfortable living space in a quiet Winter Springs neighborhood. The kitchen features granite countertops, while the main living areas are finished with durable tile flooring and the bedrooms have carpeting. Conveniently located near shopping, dining, schools, and major roadways, this home is just minutes from Downtown Orlando,

  

  Joe Cremonese

  GLOBAL PROPERTIES SALES & MGMT

  213 Buttonwood Ave, Winter Springs, FL 32708
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  /2

  $285,000

  Sold Jul 16, 2026

  167 Constitution Way, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,275 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $224/SF
  • 17 Days On Market

  Current Estimated Value $292,949

  Last Listing Agent Fernando Orsini CT HOMES REALTY CORPORATION

  167 Constitution Way, Winter Springs, FL 32708
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  /2

  Est $410,177

  Not Listed For Sale

  1323 Tarflower Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2024

  1323 Tarflower Dr, Winter Springs, FL 32708

  Last Sold Summary

  • 69 Days On Market

  Last Listing Agent Elizabeth Manchester MATTAMY REAL ESTATE SERVICES
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  $301,000

  $17K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,878 Sq Ft

  702 Glasgow Ct, Winter Springs, FL 32708

  **Fannie Mae approved** Welcome to a beautifully updated patio home tucked away on a quiet, tree-lined cul-de-sac in the desirable Pebble Creek community of The Highlands in Winter Springs. Enjoy Villa-style living with a two-story layout. Offering 4 bedrooms, 2.5 bathrooms, and a thoughtfully designed layout with the primary suite conveniently located on the first floor, this home blends

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  702 Glasgow Ct, Winter Springs, FL 32708
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  Starting at $1,095 Per Month

  • 1 - 3 Beds

  1 Laurel Oaks Dr, Winter Springs, FL 32708

  Experience resort-style living at The Avenues at Winter Springs! Our pet-friendly community offers spacious 1, 2, and 3-bedroom apartment homes with modern finishes and everyday conveniences.Enjoy amenities like a resort-style pool with sundeck, 24-hour fitness and wellness center, tennis court, playground, and leash-free pet park. Stay connected with 400 Mbps internet, and take advantage

  The Avenues at Winter Springs

  

  1 Laurel Oaks Dr, Winter Springs, FL 32708
• 

  /2

  $482,500

  Sold Nov 05, 2025

  1322 Swift Creek Way, Winter Springs, FL 32708

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft
  • Built 2020

  Last Sold Summary

  • 1% Below List Price
  • $270/SF
  • 18 Days On Market

  Current Estimated Value $483,747

  Last Listing Agent Jason Eckmann JECK ENTERPRISES LLC

  1322 Swift Creek Way, Winter Springs, FL 32708
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  /2

  Est $362,050

  Not Listed For Sale

  109 Lido Rd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Built 1984

  109 Lido Rd, Winter Springs, FL 32708

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Michael Masters EXP REALTY LLC
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  /24

  $165,000

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 945 Sq Ft

  343 San Miguel St Unit 343, Winter Springs, FL 32708

  Welcome to this freshly painted 2-bedroom, 2-bathroom condominium located in the desirable Deer Song community in Winter Springs. Offering a low-maintenance lifestyle in a convenient Central Florida location, this residence is a great fit for a first-time buyer, downsizer, seasonal resident, or investor looking for a well-positioned property with everyday comfort and community appeal. Inside, the

  

  Michael Rogers

  INNOVATIVE REALTY, LLC

  343 San Miguel St Unit 343, Winter Springs, FL 32708
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  /27

  $1,900 Per Month

  • 2 Beds
  • 2 Baths
  • 1,168 Sq Ft
  • Townhouse for Rent

  754 Summerland Dr, Winter Springs, FL 32708

  754 Summerland Dr, Winter Springs, FL 32708 — 2BR/2BA Townhouse, Available NowMove in ready 2BR/2BA townhouse in Winter Springs (Seminole County)! This 1,200 sq ft home features an attached garage/parking and community pool access. Convenient to SR-434 and 417, shopping, dining, and top rated Seminole County schools. Available now — won't last long!

  

  Rodrigo Marsal

  LIFESTYLE INTERNATIONAL REALTY

  754 Summerland Dr, Winter Springs, FL 32708
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  /2

  $630,000

  Sold Oct 24, 2025

  1118 Winter Springs Blvd, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 2,340 Sq Ft
  • Built 1979

  Last Sold Summary

  • $269/SF
  • 3 Days On Market

  Current Estimated Value $606,482

  Last Listing Agent Rick Cole KELLER WILLIAMS WINTER PARK

  1118 Winter Springs Blvd, Winter Springs, FL 32708
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  /2

  Est $332,002

  Not Listed For Sale

  322 Cello Cir, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,308 Sq Ft
  • Built 1991

  322 Cello Cir, Winter Springs, FL 32708

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Dominick Florio RE/MAX TOWN & COUNTRY REALTY
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  /30

  $644,900

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft

  248 Huntridge Way, Winter Springs, FL 32708

  There’s something about a home that makes everyday life feel a little more like vacation and this Winter Springs pool home delivers just that. Set on a spacious lot in the established Huntridge community, this 4-bedroom, 3-bath home offers nearly 2,850 square feet with room to gather, work, entertain and unwind. Soaring ceilings and abundant natural light create an open, airy feel, while the

  

  Heather Unger, PA

  ACME REAL ESTATE FLORIDA LLC

  248 Huntridge Way, Winter Springs, FL 32708
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  /26

  Starting at $1,561

  Total Monthly Price

  • 1 - 3 Beds

  151 Michael Blake Blvd, Winter Springs, FL 32708

  The Blake features modern apartment homes with granite countertops, large kitchen islands, stainless steel appliances, nine foot ceilings, private patios or balconies, and in home washers and dryers. Residents enjoy a resort style pool with cabanas, 24 hour fitness center with HIIT and Peloton equipment, coworking spaces, summer kitchens, pet grooming spa, and clubhouse amenities, all in a

  The Blake

  

  151 Michael Blake Blvd, Winter Springs, FL 32708
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  /2

  $279,000

  Sold Aug 12, 2026

  180 Constitution Way, Winter Springs, FL 32708

  • 2 Beds
  • 2.5 Baths
  • 1,275 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $219/SF
  • 56 Days On Market

  Current Estimated Value $294,479

  Last Listing Agent Jeavanna Lanza PA EXP REALTY LLC

  180 Constitution Way, Winter Springs, FL 32708
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  /2

  Est $458,007

  Not Listed For Sale

  138 Peregrine Ct, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,766 Sq Ft
  • Built 1998

  138 Peregrine Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Kim Coburn RE/MAX TOWN & COUNTRY REALTY
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  /23

  $435,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,887 Sq Ft

  806 Big Buck Cir, Winter Springs, FL 32708

  Welcome to 806 Big Buck Circle, a charming 3-bedroom, 2-bath home offering 1,887 square feet of living space in the established Oak Forest community of Winter Springs. This single-story home offers a comfortable, functional layout with plenty of opportunity to make it your own. Step outside to the screened-in back porch, a wonderful spot for morning coffee, outdoor dining, or relaxing while

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  806 Big Buck Cir, Winter Springs, FL 32708
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  /31

  Starting at $1,536

  Total Monthly Price

  • 1 - 3 Beds

  440 Courtney Springs Cir, Winter Springs, FL 32708

  Legends Winter Springs effortlessly combines exceptional service with outstanding features to provide the ultimate living experience. Located near upscale shopping and entertainment, your home is minutes to Lake Jessup and the excitement of downtown Orlando. Enjoy the peaceful, relaxing atmosphere of Legends Winter Springs. Please call for an appointment today.

  Legends Winter Springs

  

  440 Courtney Springs Cir, Winter Springs, FL 32708
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  /12

  $436,494

  Sold Jan 21, 2026

  1308 Crab Apple Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2026

  Move in Ready Sold Summary

  • $260/SF
  • 282 Days On Market

  Current Estimated Value $401,480

  Mattamy Homes Hickory Grove

  1308 Crab Apple Ln, Winter Springs, FL 32708
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  /2

  Est $618,074

  Not Listed For Sale

  702 Timberwilde Ave, Winter Springs, FL 32708

  • 5 Beds
  • 3 Baths
  • 2,574 Sq Ft
  • Built 1997

  702 Timberwilde Ave, Winter Springs, FL 32708

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Christina Frucci RE/MAX TOWN & COUNTRY REALTY
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  /30

  $409,900

  $26K PRICE DROP Pending

  • 3 Beds
  • 2.5 Baths
  • 2,063 Sq Ft

  1375 Augusta National Blvd, Winter Springs, FL 32708

  Set within Country Club Village in the heart of Tuscawilla, this spacious 3-bedroom, 2.5-bath home offers more than 2,000 square feet designed for comfortable living, easy entertaining, and room to make the space your own.Thoughtfully arranged living and dining areas provide flexibility for everyday life, while the generous floor plan creates an easy flow throughout the home. Start and

  

  Heather Unger, PA

  ACME REAL ESTATE FLORIDA LLC

  1375 Augusta National Blvd, Winter Springs, FL 32708
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  Starting at $1,660 Per Month

  • 1 - 3 Beds

  150 Bear Springs Dr, Winter Springs, FL 32708

  RiZE at Winter Springs is located in Winter Springs, Florida. We offer sixteen floor plans with one, two, and three bedroom apartment homes for rent. Apartment features include 9-foot ceilings, ceiling fans, central air and heating, a coat closet, vinyl plank flooring, walk-in closets, washer and dryer in home, an all-electric kitchen with a breakfast bar, a refrigerator, and a pantry.All

  RIZE at Winter Springs

  

  150 Bear Springs Dr, Winter Springs, FL 32708
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  /2

  $789,000

  Sold Jun 05, 2026

  10 N Fairfax Ave, Winter Springs, FL 32708

  • 8 Beds
  • 8 Baths
  • 3,636 Sq Ft
  • Built 1981

  Last Sold Summary

  • $217/SF
  • 15 Days On Market

  Last Listing Agent John Sadri JOHN SADRI & COMPANY

  10 N Fairfax Ave, Winter Springs, FL 32708
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  /2

  Est $570,972

  Not Listed For Sale

  696 Venture Ct, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,066 Sq Ft
  • Built 1988

  696 Venture Ct, Winter Springs, FL 32708

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Fran Zvaigzne COLDWELL BANKER REALTY
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  /59

  $797,500

  Pending

  • 3 Beds
  • 2 Baths
  • 2,890 Sq Ft

  1450 Bird Rd, Winter Springs, FL 32708

  ONE OF A KIND! Stunning Renovated Lakefront Home on a Private 2 Acre Peninsula – Welcome to your fully reimagined lakefront retreat at 1450 Bird Road in the heart of Winter Springs. Nestled along the serene shores of Lake Tony, this highly detailed, professionally rehabbed home blends modern luxury with timeless Florida charm. From the moment you arrive, you’ll notice the thoughtful craftsmanship

  

  Bobby Keen

  KEEN REALTY GROUP, INC.

  1450 Bird Rd, Winter Springs, FL 32708
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  Starting at $1,178 Per Month

  • Studio - 2 Beds

  101 Mosswood Cir, Winter Springs, FL 32708

  Welcome to Mosswood Apartments! At Mosswood, you'll find comfortable apartments with washer/dryer connections & extra storage. We're located just north of Orlando in Winter Springs, FL. Come home to our quiet residential setting & lake views that have easy access to I-417 and public transportation. Our single-story, villa-style East Winter Springs apartments feature private entrances and patios

  Mosswood

  

  101 Mosswood Cir, Winter Springs, FL 32708
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  $435,000

  Sold Jun 26, 2026

  417 Cruz Bay Cir, Winter Springs, FL 32708

  • 3 Beds
  • 3 Baths
  • 2,176 Sq Ft
  • Built 2006

  Last Sold Summary

  • $200/SF
  • 8 Days On Market

  Current Estimated Value $431,641

  Last Listing Agent Ron Verzaro KELLER WILLIAMS ADVANTAGE REALTY

  417 Cruz Bay Cir, Winter Springs, FL 32708
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  /2

  Est $182,555

  Not Listed For Sale

  60 Moree Loop Unit 45, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,187 Sq Ft
  • Built 1977

  60 Moree Loop Unit 45, Winter Springs, FL 32708

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Matt Merdian MERDIAN REALTY LLC
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  /16

  $524,800

  $93K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  1421 Happy Bird Ln, Winter Springs, FL 32708

  Welcome home! Fall in love this welcoming two-story home that features 4 bedrooms and 3.5 bathrooms, perfectly positioned across from the Cross Seminole Trail. Start your day with a cup of coffee on the charming covered front porch, where you can take in the refreshing breeze and picturesque views of the 13-mile trail that winds through Seminole County and connects to other scenic trails. Step

  

  Brent DeHoop

  RE/MAX ASSURED

  1421 Happy Bird Ln, Winter Springs, FL 32708
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  /38

  Starting at $1,417 Per Month

  • 1 - 3 Beds

  300 Sheoah Blvd, Winter Springs, FL 32708

  Find the life of sophistication and style that awaits you at Seville on the Green. Our Winter Springs community is nestled in the Highland Residential Neighborhood, right off of 434 and 17-92. We are minutes from I-4 and SR-417 and are less than six miles from major shopping and dining. We proudly offer one, two, and three-bedroom apartments with multiple floor plans. Select homes feature

  Seville on the Green

  

  300 Sheoah Blvd, Winter Springs, FL 32708
• 

  /2

  $483,000

  Sold Jul 31, 2026

  934 Torrey Pine Dr, Winter Springs, FL 32708

  • 3 Beds
  • 2 Baths
  • 1,678 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Above List Price
  • $288/SF
  • 268 Days On Market

  Current Estimated Value $474,411

  Last Listing Agent James Clark CENTURY 21 ALTON CLARK

  934 Torrey Pine Dr, Winter Springs, FL 32708
• 

  /2

  Est $517,789

  Not Listed For Sale

  213 Tavestock Loop, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • Built 2001

  213 Tavestock Loop, Winter Springs, FL 32708

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY
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  /21

  $170,000

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft

  417 Sheoah Blvd Unit 17, Winter Springs, FL 32708

  Welcome to this beautifully updated 2-bedroom, 2-bath first-floor condo located at 417 Sheoah Blvd, Apt 17, Winter Springs, FL 32708. This inviting home offers a spacious and comfortable floor plan with plenty of natural light throughout.The renovated kitchen provides a fresh and functional space and comes complete with all appliances. A washer and dryer are also included for added

  

  Valerie Casals

  INVESTOR'S REAL ESTATE LLC

  417 Sheoah Blvd Unit 17, Winter Springs, FL 32708
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  Starting at $1,674 Per Month

  • 1 - 3 Beds

  990 English Town Ln, Winter Springs, FL 32708

  Indulge in the luxury of living where others vacation at The Eli Winter Springs! Our community offers resort-class amenities and exceptional service to pamper residents. With a rich array of amenities, picturesque landscapes featuring swaying palm trees and tranquil waters, you can enjoy a paradise lifestyle. Conveniently located with easy access to 417, the Oviedo Marketplace, and major

  The Eli Winter Springs

  

  990 English Town Ln, Winter Springs, FL 32708
• 

  /2

  $622,000

  Sold Oct 15, 2025

  659 Cayuga Dr, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 2,492 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $250/SF
  • 4 Days On Market

  Current Estimated Value $630,502

  Last Listing Agent Laura Leigh Wood RE/MAX TOWN & COUNTRY REALTY

  659 Cayuga Dr, Winter Springs, FL 32708
• 

  /2

  Est $334,062

  Not Listed For Sale

  210 Wade St, Winter Springs, FL 32708

  • 4 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1971

  210 Wade St, Winter Springs, FL 32708

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Kimberley Beaudry ORLANDO REGIONAL REALTY
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  /45

  $375,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,107 Sq Ft

  328 Panama Cir, Winter Springs, FL 32708

  Under contract-accepting backup offers. Nestled on a quiet cul-de-sac in the desirable Foxmoor community of Winter Springs, this charming pool home offers the perfect combination of comfort, privacy, and convenience. Situated on an oversized quarter-acre lot with no HOA, this 3-bedroom, 2-bath residence features a beautifully remodeled kitchen complete with granite countertops, updated

  

  Abraham Mendez

  NONA LEGACY POWERED BY LA ROSA

  328 Panama Cir, Winter Springs, FL 32708
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  Starting at $1,242 Per Month

  • 1 - 4 Beds

  170 N Gardenridge Ct, Winter Springs, FL 32708

  Experience the many benefits of this Winter Springs apartment community, where we bring affordability, comfort, and convenience to home. Moss Park Apartments is located off Moss Park Road and State Road 434, approximately two miles east of Highway 17-92.Moss Park Apartments is a mixed-income community that offers apartment homes for unrestricted and restricted-income residents. Located

  Moss Park

  

  170 N Gardenridge Ct, Winter Springs, FL 32708
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  $433,244

  Sold Dec 30, 2025

  1284 Crab Apple Ln, Winter Springs, FL 32708

  • 4 Beds
  • 2.5 Baths
  • 1,678 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $258/SF
  • 208 Days On Market

  Current Estimated Value $412,742

  Mattamy Homes Hickory Grove

  1284 Crab Apple Ln, Winter Springs, FL 32708
• 

  /2

  Est $370,873

  Not Listed For Sale

  171 Mcleods Way, Winter Springs, FL 32708

  • 3 Beds
  • 3.5 Baths
  • 1,854 Sq Ft
  • Built 2007

  171 Mcleods Way, Winter Springs, FL 32708

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Jackie Criswell RE/MAX TOWN & COUNTRY REALTY

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