509

Homes for Sale in Connecticut - Historic

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  • /40

    $2,550,000

    Open Sun 2PM - 4PM $100K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 6,194 Sq Ft

    24 Indigo Trail, Madison, CT 06443

    Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the

    Mark McElrath William Pitt Sotheby's Int'l

    24 Indigo Trail, Madison, CT 06443
  • /25

    $199,900

    • 1 Bed
    • 1 Bath
    • 675 Sq Ft

    15 Capitol Ave Unit B, Hartford, CT 06106

    Charming Victorian brownstone condo in the heart of Downtown Hartford! This beautifully updated 1-bedroom, 1-bath residence combines modern comfort with timeless architectural character. The updated kitchen and bath, fresh paint, hardwood floors, and 2024 central air/heat pump system provide today's conveniences, while 12-foot ceilings, a marble fireplace surround, floor-to-ceiling bay windows,

    Tony Buccheri Berkshire Hathaway NE Prop.

    15 Capitol Ave Unit B, Hartford, CT 06106
  • /35

    $2,395,000

    • 4 Beds
    • 3.5 Baths
    • 4,346 Sq Ft

    171 South St, Litchfield, CT 06759

    Welcome to 171 South Street - the historic former carriage house originally designed by Guilded Age architect Ehrick Rossiter. Extensively renovated by current owner - who has created ultra-chic living spaces, modernized systems and re-landscaped to include a pool - all while preserving classic details. Rarely does an in-town property hit the market that has been elevated in such a way. The main

    Jessica Travelstead W. Raveis Lifestyles Realty

    171 South St, Litchfield, CT 06759
  • /28

    $985,000

    • 3 Beds
    • 3 Baths
    • 3,225 Sq Ft

    28 Headquarters Rd, Litchfield, CT 06759

    Stimulating and easily managed home is perfect for weekending in an idyllic, small, historic village very close to big-time cultural, sports, and wildlife attractions. Living, dining, and kitchen areas are perfectly set up for entertaining. State-of-the-art appliances. Each bedroom has its own full bath and more. Multi-person ThermoSpa hot tub in enclosed (and air-conditioned) porch looks out on

    Cleve Fuessenich Klemm Real Estate Inc

    28 Headquarters Rd, Litchfield, CT 06759
  • /38

    $1,585,000

    • 5 Beds
    • 5.5 Baths
    • 4,022 Sq Ft

    297 Rock Rimmon Rd, Stamford, CT 06903

    Double gates glide open to beckon you down a winding drive revealing this special historical residence. Set in coveted North Stamford, this 5-bedroom, 5.5 bath home combines artisanal craftsmanship with modern appeal. Originally built in 1792, its professional restorations maintain authenticity while newer construction offers numerous options for current lifestyles. From the moment you arrive,

    Jen Turano Compass Connecticut, LLC

    297 Rock Rimmon Rd, Stamford, CT 06903
  • /40

    $799,900

    • 5 Beds
    • 4 Baths
    • 3,661 Sq Ft

    538 Main St, Wethersfield, CT 06109

    Welcome To 538 Main St, An Extraordinary Waterfront Residence At The Very End Of Historic Old Wethersfield's Most Prestigious Neighborhood. This Iconic Home Offers Sweeping Views Of Wethersfield Cove With Access To The Connecticut River, Set On 1.27 Acres Of Beautifully Manicured Grounds. With Water Views From Nearly Every Room, This One-Of-A-Kind Property Blends Timeless Charm With Modern

    Michael Truong eXp Realty

    538 Main St, Wethersfield, CT 06109
  • /27

    $399,000

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

    Unlisted Address

    Welcome home to this beautifully maintained 4-bedroom, 2-bathroom colonial in the perfect location. Located on a corner lot, this property offers plenty of space for a large, or extended family. Merely steps from the beautiful Stanley Quarter Park, minutes from Stanley Golf Course, West Farms Mall, and highways, this home boasts proximity to EVERYTHING. Full of character found in homes built in

    Mario Florez William Raveis Real Estate

    Unlisted Address
  • /25

    $135,000

    $10K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 769 Sq Ft

    839 Main St Unit 111, Torrington, CT 06790

    Rare Loft Style & Sun-Drenched End Unit at Warrenton Mill! Welcome to Unit #111, a unique and spacious ~769 sq. ft. condo blending historic character, high ceilings, and flexible multi-level living. As a coveted end unit, this home features floor-to-ceiling windows and exposed brick walls that flood the entire space with natural light. The main level boasts an inviting open-concept layout with a

    Valerie Nash KW Legacy Partners

    839 Main St Unit 111, Torrington, CT 06790
  • /3

    $150,000

    $45K PRICE DROP
    • Land
    • 5.18 Acres
    • $28,958 per Acre

    1637 Connecticut 12, Gales Ferry, CT 06335

    Commercial Lot for sale zoned GFDD. (Gales Ferry Development District) This property is 5.18 acres, located on the corner of Kings Highway and Rte. 12 in Gales Ferry. Just north of the property are McDonald's, Ocean State Job Lot, Dollar General, Dunkin Donuts, various restaurants, Holmberg's Orchard, and a winery. This property is not far from the Mohegan Sun and Foxwoods casinos! Located just

    Jacqueline Beckwith Coldwell Banker Realty

    1637 Connecticut 12, Gales Ferry, CT 06335
  • /35

    $204,999

    $18K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,171 Sq Ft

    68 Thermos Ave Unit 223, Norwich, CT 06360

    Industrial Charm Meets Waterfront Tranquility: Stunning 2-Story Loft. Step into history with this unique, two-level condominium nestled inside a beautifully restored historic factory. Located on the second floor, this unit perfectly blends industrial character with modern comfort. Remodeled kitchen w granite, new appliances and tiled backsplash. The Main Level: Features an open-concept

    Joseph Wills KW Legacy Partners

    68 Thermos Ave Unit 223, Norwich, CT 06360
  • /35

    $1,675,000

    $64K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,090 Sq Ft

    705 Weed St Unit 2, New Canaan, CT 06840

    A rare opportunity to own a truly unique residence in a granite and limestone estate of historic significance, just moments from the heart of downtown New Canaan. Set on three beautifully landscaped acres, Stepping Stones is a distinguished community of only eight bespoke condominiums offering an impressive castle like setting with exceptional period craftsmanship throughout. This spacious

    Jolanta Rojek eXp Realty

    705 Weed St Unit 2, New Canaan, CT 06840
  • /40

    $650,000

    $125K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,275 Sq Ft

    126 Main St, East Hampton, CT 06424

    A rare opportunity to own TWO single-family adjacent homes in the heart of East Hampton! Rich in history and thoughtfully updated, the main residence at 124 Main Street beautifully blends timeless architectural character with the comfort and convenience of modern living. Historic details, classic craftsmanship, and tasteful updates create a home that is both elegant and inviting. A first-floor

    Justin Marino Marino Realty LLC

    126 Main St, East Hampton, CT 06424
  • /27

    $685,000

    • Land
    • 3.03 Acres
    • $226,073 per Acre

    174 Montauk Ave, Stonington, CT 06378

    A rare chance to Create Your Dream Retreat on sought-after MONTAUK AVENUE! Perched high above Historic Stonington Borough, this exceptional three-acre parcel offers a rare opportunity to create a private, beautifully appointed residence in one of Connecticut's most coveted coastal settings. Surrounded by mature stone walls and natural beauty, the property provides a peaceful sense of privacy

    Michelle Hallamore Berkshire Hathaway NE Prop.

    174 Montauk Ave, Stonington, CT 06378
  • /30

    $2,120,000

    • Land
    • 20.82 Acres
    • $101,825 per Acre

    0 Westbrook Rd, Essex, CT 06426

    Available for the first time in nearly 90 years, this exceptional 20.8 ACRES represent one of the very last large tracts of undeveloped land in historic Essex, widely celebrated as one of America's "Best Small Towns." The property features a striking combination of 8.5 level acres of virgin open field--ideal for farming, equestrian use or building--framed beautifully by an elevated wooded

    Todd Gould William Pitt Sotheby's Int'l

    0 Westbrook Rd, Essex, CT 06426
  • /37

    $749,900

    • 4 Beds
    • 3.5 Baths
    • 2,674 Sq Ft

    77 Crest Rd, Middlebury, CT 06762

    Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters,

    Michael Vartolone William Raveis Real Estate

    77 Crest Rd, Middlebury, CT 06762
  • /21

    $719,900

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,618 Sq Ft

    66 Taylor Rd, Bethel, CT 06801

    Timeless character meets contemporary comfort in this beautiful antique home with attached apartment. Major extensions and upgrades around 1990 and further upgrades in 2015. The main house offers three bedrooms and 3-and-a-half baths. The residence blends historic charm with thoughtful modern upgrades. The inviting family room opens directly onto the deck, creating an effortless connection

    Yvonne Corby Howard Hanna Rand Realty

    66 Taylor Rd, Bethel, CT 06801
  • /4

    $1,100,000

    • Land
    • 2.65 Acres
    • $415,094 per Acre

    22 Brett Rd, Fairfield, CT 06824

    An exceptional opportunity to build your dream home on one of the most desirable and scenic settings in Fairfield. This beautiful, flat 2.65-acre parcel-approved by the Wetlands Com. for a 5-bedroom, 5-bathroom residence with a pool and pool house-offers both privacy and prestige. The property is situated in the estate section of Greenfield Hill. With its driveway access on Brett Road, a

    Andrew Whiteley Brown Harris Stevens

    22 Brett Rd, Fairfield, CT 06824
  • /2

    $3,700,000

    • Land
    • 128.64 Acres
    • $28,762 per Acre

    147 Riggs St, Oxford, CT 06478

    For Sale: 147 Riggs Street, Oxford, CT - 128.64-Acre Farm with Historic Homestead A rare opportunity to own 128.64 acres of picturesque land in Oxford, Connecticut. This expansive property (Parcel 27-15-9, per Town of Oxford Assessment Parcel Map) offers mixed-use zoning (Code 016), making it ideal for residential and forestry applications. Property Highlights: Historic 3-Bedroom Cape (Built in

    Joseph Martino Joseph Martino Real Estate

    147 Riggs St, Oxford, CT 06478
  • /38

    $449,900

    • 3 Beds
    • 2 Baths
    • 1,312 Sq Ft

    9 Rose Hill Rd, Branford, CT 06405

    A rare blend of historic character and modern efficiency, this circa-1900 Branford Colonial is truly move-in ready. Originally built by Branford's Birbarie family and later purchased from the original owner's granddaughter, this quintessential New England farmhouse was extensively renovated in 2016/2017 for modern living while preserving its original charm. Set on approximately .50 acre with a

    Nora Ryan Houlihan Lawrence WD

    9 Rose Hill Rd, Branford, CT 06405
  • /24

    $6,995,000

    • 3 Beds
    • 3.5 Baths
    • 2,425 Sq Ft

    31 Meadow Wood Dr, Greenwich, CT 06830

    An extraordinary opportunity to acquire a waterfront residence within the exclusive & highly coveted Belle Haven Association - at an unusually low ''cost of entry'' point. One of just eight residences in historic Quarry Farms - which has its own gated entrance, this gut renovated 3-bedroom. 3.5 bathroom home is privately set on 1.2 acres with 220' of direct Long Island Sound frontage. Unique

    Kevin Sneddon Compass Connecticut, LLC

    31 Meadow Wood Dr, Greenwich, CT 06830
  • /33

    $2,495,000

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 4,449 Sq Ft

    7 Kingfisher Way, Stonington, CT 06378

    A classic Nantucket-style silhouette announces itself, sweeping gambrel rooflines, hand-laid shingle siding, and a trio of dormers rising above a deep, columned front porch. This site is graced with stunning views of tranquil nature preserves and open space in the heart of the island, walking distance to the ocean. This home strikes that rare balance between grandeur and warmth with an entrance

    Robyn Letourneau Berkshire Hathaway NE Prop.

    7 Kingfisher Way, Stonington, CT 06378
  • /40

    $850,000

    $45K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,620 Sq Ft

    32-b Clark Rd, Lyme, CT 06371

    A rare combination of privacy, scale, and versatility awaits on 4.6 acres in coveted Lyme. Set back off a private drive, this spacious 4-bedroom, 2.5-bath residence offers an exceptional amount of living space both inside and out. The main level is designed for comfortable everyday living and entertaining, with a generous kitchen opening to a spectacular oversized deck, formal living and dining

    Kimberly Petersen Coldwell Banker Realty

    32-b Clark Rd, Lyme, CT 06371
  • /30

    $419,000

    $30K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 1,431 Sq Ft

    799 Prospect Ave Unit C-3, West Hartford, CT 06105

    Welcome to this rare, third floor, garden-view gem! Boasting all park facing windows, one floor living, saltwater pool, friendly community, maintained landscaping, and the Elizabeth Park Historic Rose Garden right at your back door. Enjoy the gardens, paths, Summer Concert Series, and Pond House Cafe at your convenience. With a private gated entrance to the park and cars prohibited, it doesn't

    Jonathan Minerick Homecoin.com

    799 Prospect Ave Unit C-3, West Hartford, CT 06105
  • /40

    $829,000

    • 4 Beds
    • 6 Baths
    • 7,309 Sq Ft

    33 Deep River Rd, Centerbrook, CT 06409

    Incredible investment opportunity. Mixed use/flex space including two existing apartments. Historic building that has had multiple uses including an antique book store and once a brush factory. Many updates in recent years with a variety of potential uses. Level .74 acre lot, gravel parking lot, great visibility and signage. There are two apartments and multiple office/flex spaces. The property

    Susan Malan William Pitt Sotheby's Int'l

    33 Deep River Rd, Centerbrook, CT 06409
  • /40

    $6,500,000

    • Land
    • 225.84 Acres
    • $28,781 per Acre

    57 NW Corner Rd, Preston, CT 06365

    Maple Lane Farms is a unique, one of a kind, property and potential business opportunity consisting of approximately 225 contiguous acres with approximately 114 acres located in the town of Preston and approximately 111 acres located in the town of North Stonington. The property's improvements include: a c. 1993 Cape Cod style single family home; a c. 1791 Antique Colonial style residence (the

    Thomas Switz Switz Real Estate Associates

    57 NW Corner Rd, Preston, CT 06365
  • /18

    $285,000

    $10K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,218 Sq Ft

    53 Vine St, Waterbury, CT 06704

    Experience exceptional lovenience-location and convenience in perfect harmony. This 3bedroom, 1.5bath colonial sits in the heart of Waterbury, offering effortless access to the Town Green, major shopping centers, dining, and a 70acre historic park. With the highway less than five minutes away, commuting is a breeze. Whether you're a first-time homebuyer or an investor seeking value, this home

    Marquitta Saunders Coldwell Banker Realty

    53 Vine St, Waterbury, CT 06704
  • /62

    $5,995,000

    • 6 Beds
    • 4.5 Baths
    • 4,629 Sq Ft

    508 Round Hill Rd, Greenwich, CT 06831

    This stunning Round Hill estate in Greenwich, Connecticut is set in a private, knoll-top setting that ensures tranquility and picturesque views. The exquisite property spans four glorious acres and features six spacious bedrooms and four and a half baths, providing ample room for family and guests. Enjoy beautiful east and west exposures that fill the home with natural light. The layout is

    Stephen Archino Sotheby's International Realty

    508 Round Hill Rd, Greenwich, CT 06831
  • /40

    $5,195,000

    • 8 Beds
    • 8.5 Baths
    • 10,086 Sq Ft

    56 W Morris Rd, Washington Depot, CT 06794

    West Winds is one of Washington's most extraordinary country estates, offering an unparalleled combination of privacy, natural beauty, recreation, and equestrian amenities. A long, winding drive meanders through expansive meadows and orchards, culminating at a remarkable 10,000+ square-foot barn-style residence. Meticulously crafted using reclaimed beams and siding from a 19th-century Dutch barn,

    Stacey Matthews W. Raveis Lifestyles Realty

    56 W Morris Rd, Washington Depot, CT 06794
  • /31

    $479,900

    $110K PRICE INCREASE
    • 5 Beds
    • 2.5 Baths
    • 3,247 Sq Ft

    61 Flyers Dr, Norwich, CT 06360

    Space, flexibility, and location come together in this spacious cape-style home. 61 Flyers Drive offers 5 bedrooms plus an additional room ideal for a den, study, or a game/rec room. With 2.5 baths, the layout provides comfort and functionality for a variety of living needs. The home features a generously sized yard ideal for outdoor entertaining, a generously size partially finished basement

    Angela Franco mygoodagent

    61 Flyers Dr, Norwich, CT 06360
  • /14

    $1,075,000

    $290K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,392 Sq Ft

    51 Pearl St, Guilford, CT 06437

    One-of-a-Kind Opportunity in Guilford! Rarely available, this 4-unit multi-family property is ideally located on a large in-town lot in the beautiful shoreline community of Guilford. Built in 1900 and offering 2,392 sq. ft. of living space, the property features one 2-bedroom unit and three 1-bedroom units. Each unit has been thoughtfully updated and includes its own washer/dryer. Three of the

    Philip Warner William Pitt Sotheby's Int'l

    51 Pearl St, Guilford, CT 06437
  • /40

    $519,000

    • 3 Beds
    • 1.5 Baths
    • 1,550 Sq Ft

    50 Washington Rd, Woodbury, CT 06798

    CHARM, CHARACTER & CLASSIC NEW ENGLAND APPEAL IN HISTORIC WOODBURY! Welcome to this distinctive 1895 Colonial farmhouse, where timeless architectural character blends beautifully with thoughtful modern updates. Offering 3 bedrooms and 1.5 baths, this inviting home is filled with warmth, natural light, and the craftsmanship that makes an older New England home so special. Step inside to discover

    Elliott Morales eXp Realty

    50 Washington Rd, Woodbury, CT 06798
  • /39

    $7,950,000

    $1M PRICE DROP
    • 9 Beds
    • 10 Baths
    • 8,188 Sq Ft

    16 East Trail, Darien, CT 06820

    Set within the coveted Tokeneke Association, 16 East Trail is a rare legacy property where architectural pedigree meets modern luxury. Originally built in 1908 as one of the enclave's earliest residences, the home reflects the timeless elegance of McKim, Mead & White and Delano & Aldrich-thoughtfully reimagined for today's living. A masterful renovation by architect Peter Pennoyer preserves the

    Ashley Dineen Compass Connecticut, LLC

    16 East Trail, Darien, CT 06820
  • /39

    $825,000

    • 5 Beds
    • 2.5 Baths
    • 4,074 Sq Ft

    26 Beecher Rd, Brooklyn, CT 06234

    This beautiful old Colonial home was built on one of the first four parcels of land when Brooklyn was first settled. The historic character is seen throughout the home but with many modern amenities. Five Bedrooms, 2.5 Baths, 2 Fireplaces, 2 Woodstoves, Hot air heat, Newer Windows and beautiful old wood flooring. The attached heated workshop is state of the art and offers many uses. There is a

    Mae Lyons Stonehouse Real Estate Co., LLC

    26 Beecher Rd, Brooklyn, CT 06234
  • /28

    $1,650,000

    • Land
    • 3.65 Acres
    • $452,055 per Acre

    Lot 5 Milton Rd, Goshen, CT 06756

    Set along the serene shores of Woodridge Lake, Lot 5 on Milton Road presents a rare opportunity to own a substantial piece of true waterfront in one of Litchfield County's most coveted communities. Encompassing 3.65 acres with approximately 170 feet of direct lake frontage, this exceptional property combines privacy, scale, and sweeping natural beauty-an increasingly scarce offering. Gently

    Samantha Behm William Pitt Sotheby's Int'l

    Lot 5 Milton Rd, Goshen, CT 06756
  • /40

    $1,659,000

    • 4 Beds
    • 3.5 Baths
    • 2,750 Sq Ft

    25 Johnny Cake Hill Rd, Old Lyme, CT 06371

    An elegant and lovingly maintained antique colonial situated on 1.2 secluded acres near the Old Lyme Country Club. Recent updates include new landscaping front and back, new hardscaping around the pool deck, a new cedar roof, well tank, and a HVAC system including ductwork. The interior preserves the historic aspects of the home while graciously blending all the amenities of modern life. A formal

    Susan Malan William Pitt Sotheby's Int'l

    25 Johnny Cake Hill Rd, Old Lyme, CT 06371
  • /40

    $1,329,000

    • 5 Beds
    • 4.5 Baths
    • 4,158 Sq Ft

    286 Black Rock Turnpike, Redding, CT 06896

    The Rebecca Denison Homestead, established in 1708 with the present Greek Revival residence built in 1824, is a rare historic offering that beautifully combines architectural significance with modern-day living. Listed with the Connecticut State Historical Commission, this exceptional property is privately situated on 2.37 park-like acres and showcases timeless craftsmanship, meticulous

    Nora Ryan Houlihan Lawrence WD

    286 Black Rock Turnpike, Redding, CT 06896
  • /40

    $749,900

    • 7 Beds
    • 3.5 Baths
    • 4,231 Sq Ft

    362 Thompson Rd, Thompson, CT 06277

    Step back in time while enjoying the comforts of today in this exceptional Antique Colonial, built in 1830 and proudly situated on historic Thompson Hill. From the moment you arrive, the home makes a lasting impression with its welcoming wrap-around front porch, tastefully landscaped grounds, and classic circular driveway. The property also features a sizeable barn, offering abundant storage and

    Rachael Johnston Johnston & Associates Real Estate, LLC

    362 Thompson Rd, Thompson, CT 06277
  • /40

    $1,590,000

    $310K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,732 Sq Ft

    40 Ruffin Rd, Woodbury, CT 06798

    It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade

    Mary Ann Bennett Drakeley Real Estate, Inc.

    40 Ruffin Rd, Woodbury, CT 06798
  • /40

    $3,500,000

    • 3 Beds
    • 3 Baths
    • 2,700 Sq Ft

    7 Shawandassee Rd, Waterford, CT 06385

    Where the river meets the ocean, an extraordinary waterfront legacy awaits. Discover The River Estate at Shawandassee, one of the region's most captivating riverfront estates, where 1.06 acres of meticulously manicured, park-like grounds and more than 200 feet of pristine waterfront create an unparalleled coastal sanctuary. Launch your boat from the private deep-water dock and cruise effortlessly

    Sue Bowes RE/MAX on the Bay

    7 Shawandassee Rd, Waterford, CT 06385
  • /35

    $785,000

    • 3 Beds
    • 2 Baths
    • 1,396 Sq Ft

    16 River Rd, Sharon, CT 06069

    Picture starting your morning watching the sun rise over the water and ending your day with peaceful river views from almost every room in your home. Set on 2 acres along the majestic Housatonic river near Cornwall Bridge, 16 River Road has been completely transformed by a major renovation in 2024 into a modern waterfront sanctuary, while keeping its timeless antique character intact. Inside,

    Alan O'Doherty William Pitt Sotheby's Int'l

    16 River Rd, Sharon, CT 06069

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