Fairfield, CT Homes

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  /40

  $1,595,000 Open Sat 2PM - 4PM

  • 2 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  69 River St, Southport, CT 06890

  Situated near the head of Southport Harbor and within walking distance to the village, train station, and all the charm of Southport life, this 1904 jewel-box home blends historic character with elevated, designer-informed updates. With two bedrooms, two full and one half baths, charming public rooms, a finished third floor (ideal to use for additional bedroom or home office), and an attached

  Wendy Ryan Brown Harris Stevens

  69 River St, Southport, CT 06890
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  Explore Southport

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  /22

  $1,850 per month

  • 1 Bed
  • 1 Bath
  • 500 Sq Ft
  • Condo for Rent

  99 Spruce St Unit 99, Southport, CT 06890

  Bright and Well-Maintained Southport Apartment – Train, Village and HarborThis charming, sun-filled apartment is located above the garage of a well-kept Southport property. Enjoy the convenience of being very close to the train station, the picturesque village, and harbor. Pet free and smoking free property. References required.

  99 Spruce St Unit 99, Southport, CT 06890
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  $3,500,000 Sold Aug 01, 2025

  • 3,280 Sq Ft
  • $1067/SF
  • 15 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1919

  1226 Pequot Ave, Southport, CT 06890

  Tucked behind a long private drive in the heart of Southport Village, "The Cottage" is a rare and enchanting coastal retreat that captures the serenity of another time. Built c1919 by architect William S. Sloan as his personal home-Sloan was a decorated WWI veteran and grandson of DL&W Railroad president and Citibank founder Sam Sloan-this timeless haven blends heritage with ease. Set on 2.35

  Michelle Genovesi William Raveis Real Estate

  1226 Pequot Ave, Southport, CT 06890
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  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  670 Kings Hwy W Unit 670, Fairfield, CT 06890

  670 Kings Hwy W Unit 670, Fairfield, CT 06890
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  /40

  $12,000,000

  • 7 Beds
  • 6.5 Baths
  • 8,119 Sq Ft

  260 Willow St, Southport, CT 06890

  Welcome to 260 Willow Street-where timeless design meets modern luxury. Thoughtfully reimagined and meticulously executed, this exceptional Southport Village residence embodies architectural refinement and effortless elegance. Renowned architect Christopher Pagliaro's philosophy of "addition by subtraction" is evident throughout, resulting in a home that is both sophisticated and serene. Every

  Elizabeth Tritschler William Raveis Real Estate

  260 Willow St, Southport, CT 06890
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  /5

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • House for Rent

  62 Spruce St S Unit 1, Fairfield, CT 06890

  Available for $5,500/month, this lower-level unit at 62 Spruce Street offers the perfect blend of historic Southport charm and modern convenience. The kitchen and two full baths are being fully-remodeled and will be completed for your move-in date by mid-end of August! Located on a quiet, tree-lined street that leads directly to the Southport Metro North station, this commuter-friendly home

  Michael Cerreta William Raveis Real Estate

  62 Spruce St S Unit 1, Fairfield, CT 06890
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  $2,625,000 Sold Jun 30, 2025

  • 2,615 Sq Ft
  • $1004/SF
  • 12 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1834

  81 Main St, Southport, CT 06890

  CLASSIC PERFECTION IN SOUTHPORT VILLAGE - Circa 1834. With an excellent Southport Village location, this impeccably renovated 4 Bedroom. 3.5 Bath historic house is classic perfection inside and out. Light and airy; stunning interiors are bathed in sunlight, presenting designer lighting & finishes, gorgeous wide plank pine flooring, and thoughtful architectural elements throughout 2650+/- square

  Victoria Fingelly Higgins Group Real Estate

  81 Main St, Southport, CT 06890
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  Est $1,256,107 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,621 Sq Ft

  171 Woodrow Ave, Southport, CT 06890

  171 Woodrow Ave, Southport, CT 06890
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  /28

  $585,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft

  116 Southport Woods Dr, Southport, CT 06890

  Welcome to 116 Southport Woods Drive, a bright and versatile 2 bedroom, 2 full bath first-floor corner unit in the highly desired Southport Woods community, where comfort and convenience come together effortlessly. The entire unit features brand new floors, stylish new window treatments, and a freshly painted interior, creating an updated and inviting atmosphere throughout. The kitchen offers

  Tara Gleason William Raveis Real Estate

  116 Southport Woods Dr, Southport, CT 06890
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  /23

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  26 Hulls Hwy Unit 26, Southport, CT 06890

  Move-in ready spacious 2nd floor condo featuring 2 bedrooms and 2 full baths, located in a well-maintained condominium complex. This unit offers central air, a spacious deck, access to a refreshing pool, a one-car detached garage, an additional reserved parking space, and washer/dryer in unit. Updated kitchen and baths. Enjoy the convenience of being just a short walk to the Southport train

  Madeline O'Shea Coldwell Banker Realty

  26 Hulls Hwy Unit 26, Southport, CT 06890
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  $630,000 Sold Jun 12, 2025

  • 1,048 Sq Ft
  • $601/SF
  • 49 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1884

  132 Pequot Ave, Southport, CT 06890

  Location, charm, and lifestyle-all in one! Step into storybook charm in the heart of Southport Village! Perched gracefully atop a hill, this enchanting c.1884 Farmhouse offers rare privacy just steps from the harbor, beach, village shops, restaurants, and Metro-North train-a true commuter's dream. Thoughtfully updated with a new roof and siding, the home effortlessly blends vintage character with

  Nicole Costantino Keller Williams Realty

  132 Pequot Ave, Southport, CT 06890
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  Est $722,000 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft

  936 Kings Hwy W, Southport, CT 06890

  936 Kings Hwy W, Southport, CT 06890
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  /40

  $4,975,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,753 Sq Ft

  1060 Harbor Rd, Southport, CT 06890

  ELEGANCE ON SOUTHPORT HARBOR - With an idyllic Village location, this elegant 3753 square foot, architect designed residence enjoys expansive water views over Southport Harbor and Long Island Sound. Exquisite rock gardens enhance the gently, sweeping .51 acre property extending to the Harbor's edge; a perfect launch for kayaking. The wonderful floor plan offers a stunning Living Room with

  Victoria Fingelly Higgins Group Real Estate

  1060 Harbor Rd, Southport, CT 06890
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  /39

  $4,800 per month

  • 3 Beds
  • 1.5 Baths
  • 1,618 Sq Ft
  • House for Rent

  10 Taylor Place, Southport, CT 06890

  HEAT, ELECTRIC, AIR CONDITIONING, WATER, SEWER, TRASH, LAWN & GARDEN, SNOW REMOVAL INCLUDED IN MONTHLY RENT. Charming 3-bedroom colonial on a quiet side street in the heart of Southport, one of Fairfield's most desirable waterfront communities. Make your way up the brick garden path past hydrangeas, lilacs, hostas, and countless summer blooms to this timeless home. Step into the welcoming foyer

  Gayle Worthington William Raveis Real Estate

  10 Taylor Place, Southport, CT 06890
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  $635,000 Sold Jun 06, 2025

  • 1,200 Sq Ft
  • $529/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  57 Southport Woods Dr Unit 57, Southport, CT 06890

  Wonderful recently updated 2 Bedroom, 2 Bathroom, Upper level Unit tucked away in a quiet corner of complex overlooking beautiful green space. Conveniently located end-unit 1 car garage with private storage. Large and mostly covered deck. Recent updates include beautiful kitchen with quartz countertops, stacked subway tile, newer high-end stainless appliances, cabinetry with deep large pantry and

  Ellen Fusco Compass Connecticut, LLC

  57 Southport Woods Dr Unit 57, Southport, CT 06890
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  Est $812,982 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 1,920 Sq Ft

  164 Oxford Rd, Southport, CT 06890

  164 Oxford Rd, Southport, CT 06890
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  /24

  $3,995,000 Pending

  • 6 Beds
  • 5.5 Baths
  • 5,200 Sq Ft

  987 Pequot Ave, Southport, CT 06890

  SOUTHPORT CHIC - This home is rented until June 2025. Just steps to the beach, Harbor and quaint Southport Village, this French inspired beauty will make you feel like you've been whisked away to the European countryside although you're just 50 minutes from Manhattan. In the neighborhood of multi-million dollar seaside estates, restored antique homes, and newer builds with that Je ne sais quoi

  Jaclyn Picarillo Higgins Group Bedford Square

  987 Pequot Ave, Southport, CT 06890
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  /19

  $4,200 per month

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • House for Rent

  95 Taylor Place, Southport, CT 06890

  Discover a fantastic rental opportunity in Southport, CT! This Cape Cod home features a comfortable layout with hardwood flooring, a sunroom/den, living room, and dining room, along with three bedrooms and two full baths-everything you need to embrace the Southport lifestyle. Enjoy the convenience of walking or biking to the Southport train station, beach, harbor, and the charming village with

  Stephanie Barnes William Raveis Real Estate

  95 Taylor Place, Southport, CT 06890
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  $1,165,000 Sold May 28, 2025

  • 2,619 Sq Ft
  • $445/SF
  • 9 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1985

  450 Center St Unit 1, Southport, CT 06890

  Ideal location in the heart of Southport! Walk to Southport Village, the Harbor, Pequot Yacht Club, Pequot Library and the Train. This is the lifestyle you've been waiting for! Beautiful End-Unit with abundant natural light and a cheerful disposition. Gorgeous, updated Kitchen with Quartz Countertops and a generous Center Island, stainless steel appliances, crisp white cabinetry and elegant

  Lorelei Atwood Higgins Group Real Estate

  450 Center St Unit 1, Southport, CT 06890
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  Not Listed For Sale

  • 6 Beds
  • 5.5 Baths
  • 4,307 Sq Ft

  944 Pequot Ave, Southport, CT 06890

  944 Pequot Ave, Southport, CT 06890
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  /40

  $2,000,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,534 Sq Ft

  346 Taintor Dr, Southport, CT 06890

  Welcome to 346 Taintor Drive....a FABULOUS SOUTHPORT VILLAGE location on this quiet & sought after street, offering the BEST of BOTH Worlds! Prospect Lane Corner location allows walkability to The Village w Restaurants, Coffee, Deli, NYC train, Fitness Club, Library & the popular Southport Harbor. A taste of yesteryear w/ALL of the modern conveniences! Colonial style features OPEN FLOOR PLAN, En

  Christine Magliocco Higgins Group Real Estate

  346 Taintor Dr, Southport, CT 06890
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  /29

  $6,500 per month

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • House for Rent

  176 Main St Unit 1B, Southport, CT 06890

  VERY SPECIAL SOUTHPORT VILLAGE RENTAL OPPORTUNITY - This 2055 square foot flat, occupying the full second floor of a magnificent Gothic style Victorian residence, is presently finalizing a stunning and complete renovation. Providing great scale and proportion, the spacious floor plan features a Living Room with decorative Fireplace, Formal Dining Room with decorative Fireplace, Bay Window and

  Victoria Fingelly Higgins Group Real Estate

  176 Main St Unit 1B, Southport, CT 06890
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  $790,000 Sold May 21, 2025

  • 1,267 Sq Ft
  • $624/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1935

  185 Woodrow Ave, Southport, CT 06890

  Storybook Cape in Southport Move right into this delightful Cape nestled in the heart of Southport! Featuring two beautifully renovated full baths, gleaming hardwood floors, classic stone walls, a new driveway, and a new roof, this home exudes warmth and character. The light-filled sun porch leads to an inviting layout, including a cozy den, a family room with a fireplace, and a spacious kitchen

  Barbara Sweeney Coldwell Banker Realty

  185 Woodrow Ave, Southport, CT 06890
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  Est $3,786,476 Not Listed For Sale

  • 6 Beds
  • 4.5 Baths
  • 5,795 Sq Ft

  916 Pequot Ave, Southport, CT 06890

  916 Pequot Ave, Southport, CT 06890
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  /39

  $669,999 Under Contract

  • 3 Beds
  • 3.5 Baths
  • 2,240 Sq Ft

  668 Kings Hwy W, Southport, CT 06890

  Move right into this exceptional 3-bedroom, 3.5-bathroom half duplex, perfectly located in the coveted Southport neighborhood. Thoughtfully designed with timeless elegance and modern convenience, this spacious residence features gleaming hardwood floors throughout, detailed crown moldings, and an open layout that effortlessly balances comfort and functionality. The main level showcases a living

  Kenneth Zerella II William Raveis Real Estate

  668 Kings Hwy W, Southport, CT 06890
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  $3,000,000 Sold May 02, 2025

  • 3,580 Sq Ft
  • $838/SF
  • 189 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1918

  319 Harbor Rd, Southport, CT 06890

  Direct waterfront property with incomparable views across Southport Harbor, the Country Club of Fairfield golf course, and Long Island Sound. Generational opportunity to renovate or create your own vision in this most coveted of locations in historic Southport Village. Set high on a hill, the property faces due South for maximum light and views towards Long Island. Plentiful birdlife and boating

  Andrew Whiteley Brown Harris Stevens

  319 Harbor Rd, Southport, CT 06890
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  Est $3,078,355 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,843 Sq Ft

  1070 Pequot Ave, Southport, CT 06890

  1070 Pequot Ave, Southport, CT 06890
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  $800,000 Sold Apr 29, 2025

  • 2,481 Sq Ft
  • $322/SF
  • 94 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1924

  35 John St, Southport, CT 06890

  Amazing opportunity to live or work in downtown Southport. Users and builders bring your ideas and designs. Interior includes beautiful original trim detail. Potential for expansion. Enclosed porch could easily be converted to living area. Located in the Designed Industrial Zone, which allows for alternative uses (See under commercial listing).

  Ellen Balazs-Byington Berkshire Hathaway NE Prop.

  35 John St, Southport, CT 06890
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  /37

  Est $6,874,497 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,970 Sq Ft

  1095 Pequot Ave, Southport, CT 06890

  1095 Pequot Ave, Southport, CT 06890
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  $2,340,000 Sold Apr 28, 2025

  • 4,243 Sq Ft
  • $551/SF
  • 14 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1831

  1 Church St, Southport, CT 06890

  Welcome to a Rare Historic Gem in the Heart of Southport. Nestled on a private and serene one-acre lot, this truly unique historic carriage house, built in 1831, offers a rare opportunity to own a piece of Southport's rich architectural heritage. Located on a quiet and less-traveled street, this charming home combines classic elegance with the potential for a modern reimagining, making it ideal

  Amy Waugh Curry ABR CRS GRI Berkshire Hathaway NE Prop.

  1 Church St, Southport, CT 06890
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  Est $1,106,363 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,459 Sq Ft

  29 Osborne Place, Southport, CT 06890

  29 Osborne Place, Southport, CT 06890
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  $624,500 Sold Apr 24, 2025

  • 1,200 Sq Ft
  • $520/SF
  • 20 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  214 Southport Woods Dr Unit 214, Southport, CT 06890

  First floor, 2 bedroom, 2 bathroom 1,200 square foot unit with a corner garage in the complex. The apartment is directly across from the clubhouse, pool and paddle tennis court. The garage is the closest unit to the apartment's entrance. All windows and the patio look out to Mill Hill Terrace, offering added privacy. The kitchen was beautifully updated with quartz counters & high quality

  Matt Lahey Higgins Group Real Estate

  214 Southport Woods Dr Unit 214, Southport, CT 06890
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  /2

  Est $757,000 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,061 Sq Ft

  45 Osborne Place, Southport, CT 06890

  45 Osborne Place, Southport, CT 06890
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  $599,000 Sold Apr 15, 2025

  • 1,109 Sq Ft
  • $540/SF
  • 29 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 2020

  32 Bronson Rd, Southport, CT 06890

  Sunkissed colonial in Southport. This newly reconstructed, picture-perfect colonial is situated in lovely Southport. With 3 floors of living space, the first floor offers an open floor plan with living room, eat-in kitchen and an outdoor deck. Plus gleaming hardwood floors and (top of the line) stainless appliances including a professional Viking gas stove. 2nd floor has two bedrooms, full bath

  Gabrielle DiBianco Higgins Group Bedford Square

  32 Bronson Rd, Southport, CT 06890
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  Est $1,046,000 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,860 Sq Ft

  1503 Mill Hill Terrace, Southport, CT 06890

  1503 Mill Hill Terrace, Southport, CT 06890
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  $660,000 Sold Apr 08, 2025

  • 1,500 Sq Ft
  • $440/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1969

  207 Southport Woods Dr Unit 207, Southport, CT 06890

  Experience modern living in this impeccably upgraded 3-bedroom, 2-bath condo, perfectly positioned in a sought-after community. The gourmet kitchen has been fully reimagined with granite counters and classic white shaker cabinets, seamlessly connecting to the living area via a stylish pass-through. Newly refinished hardwood floors, recessed lighting, and detailed crown molding create an inviting,

  Shoshana Snyder William Raveis Real Estate

  207 Southport Woods Dr Unit 207, Southport, CT 06890
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  Est $630,714 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,150 Sq Ft

  92 Hulls Hwy, Southport, CT 06890

  92 Hulls Hwy, Southport, CT 06890
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  $1,389,000 Sold Apr 06, 2025

  • 3,125 Sq Ft
  • $444/SF
  • 38 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2024

  71 Osborne Place, Southport, CT 06890

  Luxurious turn-key home in desirable Southport location. Built in 2024 by respected local builder, Kardamis Construction, this Colonial style half-duplex offers 3,100 Sq. Ft. of living space across 3 floors. The unique, "staggered" design minimizes the shared wall of the duplex, and truly gives this property the appearance of a single-family home. The staggered layout also enables each side to

  Anthony Gigliotti Keller Williams Realty

  71 Osborne Place, Southport, CT 06890
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  Est $607,517 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,525 Sq Ft

  4 Hulls Hwy, Southport, CT 06890

  4 Hulls Hwy, Southport, CT 06890
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  $975,000 Sold Mar 28, 2025

  • 2,016 Sq Ft
  • $484/SF
  • 47 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1998

  278 Woodrow Ave, Southport, CT 06890

  Prime Southport location at a fantastic price point-welcome to 278 Woodrow Avenue! This move-in ready colonial features 4 bedrooms, 3 full bathrooms, hardwood floors throughout and an abundance of natural light, all spread across 2,016 sq. ft. The entire interior has been freshly painted offering a bright, light and current appearance. The dining room to the right of the front foyer, has recently

  David Hilliker William Raveis Real Estate

  278 Woodrow Ave, Southport, CT 06890

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