57

Homes for Sale near Joel Barlow High School

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  • /22

    $439,000

    • 2 Beds
    • 1 Bath
    • 1,044 Sq Ft

    37 Highland Ave, Redding, CT 06896

    Charming two-bedroom cottage set on a beautifully level property, offering a private retreat surrounded by a peaceful, bucolic setting. This home is full of potential-bring your vision and transform it into your perfect escape or year-round residence. Enjoy the ease of convenience of a prime location, just minutes to shopping, dining and major commuting routes. A rare opportunity to create

    Agent Photo

    Kateryna Ulerio

    Houlihan Lawrence

    (475) 255-7478

    37 Highland Ave, Redding, CT 06896
  • /30

    $799,000

    • 3 Beds
    • 2 Baths
    • 2,025 Sq Ft

    125 Buck Hill Rd, Easton, CT 06612

    Now Fully Painted and Ready-to-Move-in! Set on over 3 wooded acres in Lower Easton, 125 Buck Hill Road is a spacious, character-rich ranch offering privacy, flexibility, and potential. Tucked among mature trees and natural rock outcroppings, the home feels like a private retreat-yet it's just minutes from Fairfield, Westport, and the Merritt Parkway for NYC commuters! Originally built in 1967 and

    Jessica Lane

    Serhant Connecticut, LLC

    (475) 264-5876

    125 Buck Hill Rd, Easton, CT 06612
  • /38

    $1,325,000

    • 4 Beds
    • 5 Baths
    • 4,414 Sq Ft

    10 Chapman Place, Redding, CT 06896

    Private Luxury Meets Modern Sophistication in Redding! Discover the perfect blend of classic New England charm and cutting-edge convenience. This pristine 4,414 SF Colonial is situated on 2.67 acres at the end of a peaceful cul-de-sac. Inside, you are welcomed through a stately foyer with marble flooring, a sweeping staircase, and soaring ceilings. Gleaming hardwood floors guide you through a

    Agent Photo

    Mary Phelps

    William Pitt Sotheby's Int'l

    (475) 264-9866

    10 Chapman Place, Redding, CT 06896
  • /40

    $7,400,000

    $1M PRICE DROP
    • 7 Beds
    • 6.5 Baths
    • 9,420 Sq Ft

    63 Turney Rd, Redding, CT 06896

    Another Day in Paradise! Timeless grandeur, architectural mastery, and opportunity define this exceptional plantation-style colonial set on 39.23 acres bordered by 100+ acres of protected forestland-a rare opportunity for stately country living in a singular setting.For the sportsman, pristine woodlands and abundant wildlife offer boundless opportunities for hunting, hiking, and connecting with

    Agent Photo

    Roni Agress

    William Pitt Sotheby's Int'l

    (203) 717-5061

    63 Turney Rd, Redding, CT 06896
  • /37

    $775,000

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

    119 Staples Rd, Easton, CT 06612

    Rare opportunity in the heart of Easton..... and we know paradise does exist, because it's right here at 119 Staples Road! Nestled on over 4 private acres with stone walls and privacy, this special property abuts more than 158 acres of protected Aquarion Water Company land stretching toward Black Rock Turnpike, creating an extraordinary backdrop of nature, and tranquility. Freshly painted

    Agent Photo

    Judy Szablak

    Coldwell Banker Realty

    (475) 262-9753

    119 Staples Rd, Easton, CT 06612
  • /40

    $1,649,900

    $100K PRICE DROP
    • 6 Beds
    • 5 Baths
    • 4,033 Sq Ft

    12 Werf Dr, Redding, CT 06896

    Welcome to this expansive and beautifully updated six-bedroom Colonial, offering three full and two half baths and thoughtfully positioned on a sprawling 2.42-acre lot that provides both privacy and presence. A grand wraparound driveway creates a striking approach to the home, offering ample parking in addition to a two-car attached garage ideal for guests, entertaining, and everyday convenience.

    Jonathan Gineo Silver and Oak Realty

    12 Werf Dr, Redding, CT 06896
  • /40

    $2,378,000

    $60K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 6,199 Sq Ft

    16 Robin Hood Ln, Easton, CT 06612

    This stately Colonial tucked away at the end of a cul de sac in Easton, blends classic architecture with resort style living. From the moment you arrive, the brick facade and grand scale set the tone. Stepping inside, the impressive two story foyer with gleaming marble floors and Palladian windows creates a true magazine worthy first impression. Crown molding flows throughout the home along with

    Bogdan Stefanide KW Legacy Partners

    16 Robin Hood Ln, Easton, CT 06612
  • /26

    $1,795,000

    • 4 Beds
    • 4.5 Baths
    • 6,259 Sq Ft

    2 Longwood Dr, Redding, CT 06896

    Newly Priced at $1,795,000 *** Exceptional Luxury Value in Redding's Limited Inventory Market. In today's market, where luxury inventory in Redding remains extremely limited, 2 Longwood Drive presents a rare opportunity to own a meticulously maintained custom estate offering exceptional square footage, privacy, flexibility, and long term value in one of Connecticut's most desirable communities.

    Jeffrey Kaplan William Raveis Real Estate

    2 Longwood Dr, Redding, CT 06896
  • /2

    $235,000

    • Land
    • 6.54 Acres
    • $35,933 per Acre

    54 Rock House Rd, Easton, CT 06612

    A 6.54-acre parcel of undeveloped, rugged land located off Rock House Road in Easton. purchaser is responsible for completing independent verification diligence and confirming feasibility. Access is provided via an approximately 600-foot-long, 50-foot-wide right-of-way to the property, identified by a fence line. If you plan to walk the land, hiking boots are required and an appointment must be

    Pilar Rios US Asset Realty

    54 Rock House Rd, Easton, CT 06612
  • /40

    $1,877,000

    • 5 Beds
    • 3.5 Baths
    • 4,352 Sq Ft

    1960 North St, Fairfield, CT 06824

    This timeless colonial sits beautifully behind a long sweep of native New England stone wall that Greenfield Hill is known for. Fully renovated and expanded in 2010, every decision was made with intention: preserve the home's classic character while creating the open, connected spaces today's lifestyle demands. Rooms that flow and breathe, quality millwork and molding details, and hardware and

    Linda Blackwell Houlihan Lawrence

    1960 North St, Fairfield, CT 06824
  • /35

    $2,395,000

    Coming Soon
    • 4 Beds
    • 4.5 Baths
    • 4,168 Sq Ft

    224 Wilson Rd, Easton, CT 06612

    Many buyers today are searching for something remarkably difficult to find: the ability to simplify life without sacrificing beauty, privacy, or prestige. Welshmoor delivers exactly that. Set behind stone pillars and a winding tree-lined drive on five extraordinary acres, this private estate offers something rarely found today: the ability to live beautifully and entirely on one level. Rolling

    Cindy Raney Coldwell Banker Realty

    224 Wilson Rd, Easton, CT 06612
  • /7

    $775,000

    $120K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 2,732 Sq Ft

    134 Delaware Rd, Easton, CT 06612

    Lovely private Easton wooded setting overlooking Morehouse Brook. Large level parking that allows truck turn around. Lower driveway access to Brook and lower level entrance.Close to Parkway, Rt. 15 former exit 46 1 mile away.

    Ray Baldyga Dogwood Realty

    134 Delaware Rd, Easton, CT 06612
  • /40

    $1,799,000

    $50K PRICE DROP
    • 7 Beds
    • 5 Baths
    • 8,933 Sq Ft

    101 Northwood Dr, Easton, CT 06612

    FILL UP THIS ENORMOUS HOUSE AND STOP PAYING 4- OR MORE PRIVATE BILLS FOR K-12. EXCEPTIONAL SIZE VALUE. Transition to Easton's top-tier, 10/10 rated public academies-ranked in the top 10 of the state-and reclaim your freedom. This massive footprint is designed for high-capacity living and maximum internal volume. AN ARCHITECTURAL TOUR DE FORCE: This Avant-garde Bauhaus-linear design of

    Steven Koleno Beycome of Connecticut

    101 Northwood Dr, Easton, CT 06612
  • /40

    $4,999,000

    • 5 Beds
    • 9 Baths
    • 7,070 Sq Ft

    294 Maple Rd, Easton, CT 06612

    A rare offering, this Gambrel shingle-style estate is a sanctuary on over 6 acres on a cul-de-sac, offering a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered

    Linda Toscano Coldwell Banker Realty

    294 Maple Rd, Easton, CT 06612
  • /38

    $729,900

    Open Sun 12PM - 2PM
    • 3 Beds
    • 3 Baths
    • 1,795 Sq Ft

    101 Sport Hill Rd, Easton, CT 06612

    Nestled in desirable Lower Easton, this charming Cape Cod-style home offers space, comfort, and timeless appeal just minutes from the Merritt Parkway, shopping, and town amenities. A beautiful stone exterior and circular driveway welcome you into a bright and spacious interior featuring a large living room with fireplace, an inviting eat-in kitchen, laundry room, and half bath. Upstairs offers

    Katiria Chiluisa RE/MAX Right Choice

    101 Sport Hill Rd, Easton, CT 06612
  • /32

    $885,000

    • 4 Beds
    • 2.5 Baths
    • 3,260 Sq Ft

    76 Pocahontas Rd, Redding, CT 06896

    This distinct 4-bedroom Colonial offers a rare blend of charm and modern luxury. Originally built as a ranch in 1962, the home was completely transformed in 2000 with a full second-floor addition, resulting in a unique, airy open floor plan. A stunning 2-sided brick fireplace serves as the heart of the home, artfully dividing the living spaces while maintaining a seamless flow. The chef's kitchen

    Lisa Pompeo William Pitt Sotheby's Int'l

    76 Pocahontas Rd, Redding, CT 06896
  • /27

    $499,000

    • 3 Beds
    • 1.5 Baths
    • 1,234 Sq Ft

    219 Redding Rd, Redding, CT 06896

    This antique home is a blend of rustic charm and modern finishes. You'll love the spacious & extremely accommodating living and dining rooms that allow for memorable gatherings. A large room on the main floor with adjoining half bath could be an ideal guest room, office or primary bedroom, allowing this home the possibility to live like a 4 bedroom. Original beams throughout the home not only

    Cher Iravani Redevelopment Realty Group

    219 Redding Rd, Redding, CT 06896
  • /2

    $499,000

    • Land
    • 8.89 Acres
    • $56,130 per Acre

    65 Umpawaug Rd, Redding, CT 06896

    Glorious interior lot in pine setting on scenic Umpawaug Rd. Owner architect/builder can design and build to suit. See listing #170511696 Owner/agent

    Jodi Langford Coldwell Banker Realty

    65 Umpawaug Rd, Redding, CT 06896
  • /35

    $1,450,000

    $45K PRICE DROP
    • 5 Beds
    • 6 Baths
    • 4,716 Sq Ft

    74 Black Rock Turnpike, Redding, CT 06896

    Old Redding charm meets elevated modern living at this exceptional gated Contemporary Colonial offering over 4,700 SF plus approximately 1,800 SF of finished walk-out lower level. Set behind stately iron gates and stone pillars, a private drive leads to a dramatic marble foyer and grand staircase. The custom Clark Construction kitchen, enhanced in 2023, features dual full-size Thermador ovens,

    Brianna Carvalho Compass Connecticut, LLC

    74 Black Rock Turnpike, Redding, CT 06896
  • /30

    $1,395,000

    • 4 Beds
    • 5 Baths
    • 5,282 Sq Ft

    4 Long Ridge Rd, Redding, CT 06896

    This unique property offers the perfect blend of living, working and investing in a picturesque and convenient setting. For 15 years, the current owner has enjoyed a seamless "work from home" lifestyle, with a spacious upstairs apartment above the main building and store. The property also includes a separate retail cottage, ideal for generating rental income or expanding your business

    Christine Poppy Compass Connecticut, LLC

    4 Long Ridge Rd, Redding, CT 06896
  • /36

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 1,774 Sq Ft

    471 Newtown Turnpike, Redding, CT 06896

    Beautifully professionally landscaped, level 2-acre lot on the peaceful end of Newtown Turnpike, this charming 3-bedroom, 2.5-bath. Cape combines classic character with modern living. The home has been meticulously maintained and upgraded, offering a perfect retreat in the heart of Redding. Step into the heart of the home: a brand-new custom kitchen featured in the recently added expansion.

    Waldde Valdez Modern Day Real Estate

    471 Newtown Turnpike, Redding, CT 06896
  • /7

    $900,000

    • Land
    • 15.27 Acres
    • $58,939 per Acre

    67 Umpawaug Rd, Redding, CT 06896

    Exceptional land on scenic Umpawaug Rd. House site overlooks spectacular quartz quarry to the rear with panoramic views to the front. Perfect for breathtaking hideaway in the country. Owner/architect can design and build to suit. Additional land available. Owner/agent

    Jodi Langford Coldwell Banker Realty

    67 Umpawaug Rd, Redding, CT 06896
  • /37

    $1,037,875

    $112K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 5,302 Sq Ft

    80 Maple Rd, Easton, CT 06612

    Set on 3+ acres,well-appointed Colonial Style Home custom built in 1999,offering 3,802 sq ft and +/-1,500 sq ft of fully finished walk-out Lower Level. Original owners. Custom built stone walkway leads you to the front door, opening up to an elegant two-story Foyer, set with granite tile. Hardwood flooring throughout. Main level features a study/office with two sets of French Doors for optimal

    Erika Portanova Songer William Pitt Sotheby's Int'l

    80 Maple Rd, Easton, CT 06612
  • /38

    $639,000

    Open Sun 12PM - 4PM $51K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,920 Sq Ft

    70 Dayton Rd, Redding, CT 06896

    Welcome to your dream home located just steps from Devil's Den Park Trail. This beautifully updated property offers comfort, space, and privacy on nearly one acre of land. The home features a new roof and new siding, along with freshly painted interiors and hardwood floors throughout. There are new light fixtures that add a clean and modern feel to every room. The kitchen has been fully updated

    Nikolina Kajtazovic Coldwell Banker Realty

    70 Dayton Rd, Redding, CT 06896
  • /40

    $1,399,000

    Open Sat 1PM - 3PM $200K PRICE DROP
    • 6 Beds
    • 4.5 Baths
    • 4,204 Sq Ft

    46 Sherwood Rd, Easton, CT 06612

    Set on a park-like 4.39-acre parcel, this timeless 2006 center hall colonial offers a rare blend of privacy, natural beauty, and exceptional quality. A sweeping front lawn welcomes you, while the property unfolds to reveal a serene pond, bluestone patio with sitting wall, fenced-in raised-bed garden, charming potting shed & greenhouse - perfect for those who appreciate both elegance and nature.

    Gayle Worthington William Raveis Real Estate

    46 Sherwood Rd, Easton, CT 06612
  • /40

    $1,500,000

    Open Sat 1PM - 3PM
    • 5 Beds
    • 4 Baths
    • 4,728 Sq Ft

    28 Goodridge Rd, Redding, CT 06896

    You will take a deep breath as soon as you drive through the beautiful and tranquil landscape of this part of Redding. As you approach the driveway you are greeted by a large antique barn for storing Animals/Cars/Toys. driving down the driveway you see the large colonial farmhouse with expansive front porch 5 bedroom and 4 full baths. The flexible open floor allows for easy daily life as well as

    Margaret Upton-Mirowski Coldwell Banker Realty

    28 Goodridge Rd, Redding, CT 06896
  • /40

    $1,295,000

    • 4 Beds
    • 3.5 Baths
    • 5,048 Sq Ft

    35 Hunting Ridge Rd, Easton, CT 06612

    Welcome to this Elegant Custom Colonial gracefully set on a picturesque cul-de-sac in one of Easton's most beautiful neighborhoods, surrounded by distinguished homes and professionally landscaped grounds. Nestled on 3 private acres, this exceptional residence offers over 4,300 square feet of tranquil living designed for both luxury and entertaining. An impressive two-story foyer welcomes you into

    Vera Maximin Higgins Group Real Estate

    35 Hunting Ridge Rd, Easton, CT 06612
  • /30

    $885,000

    Open Sat 2PM - 4PM $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,068 Sq Ft

    8 Ferndale Dr, Easton, CT 06612

    Beautifully renovated 4-bedroom, 3-bath Cape set on a private acre in desirable Easton. This home offers hardwood floors throughout, a bright updated kitchen, and a partially finished basement for added flexible living space. Major improvements completed in 2015 include the roof, exterior siding, central air, and full interior updates, providing a move-in ready feel. Enjoy outdoor living on the

    Brigita Geiger BHHS Darien/New Canaan

    8 Ferndale Dr, Easton, CT 06612
  • /39

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    37 Lamppost Dr, Redding, CT 06896

    Highest and best due 6/1/@ 4PM Nestled on a quiet cul-de-sac in desirable West Redding, this inviting 4 bedroom, 2.5 bath home offers the perfect blend of comfort, space, sustainability, and commuter convenience. Located in a town affectionately known as the "Vermont of Connecticut," Redding is cherished for its scenic wooded landscapes, top ranked schools, and peaceful atmosphere. Inside, a

    Terri Tournas Coldwell Banker Realty

    37 Lamppost Dr, Redding, CT 06896
  • /40

    $1,399,000

    Open Sat 1PM - 3PM
    • 5 Beds
    • 5.5 Baths
    • 5,362 Sq Ft

    70 Crossbow Ln, Easton, CT 06612

    Set on 3 private acres in the heart of central Easton, this impressive Colonial offers over 5,000 square feet of living space with 5 bedrooms and 6 bathrooms. Surrounded by mature landscaping and set behind a long private driveway, the property offers exceptional privacy and a peaceful setting. A dramatic two-story foyer creates a grand first impression. Formal living and dining rooms add

    Monika Zieja Compass Connecticut, LLC

    70 Crossbow Ln, Easton, CT 06612
  • /40

    $7,725,000

    • 7 Beds
    • 13 Baths
    • 13,094 Sq Ft

    206 Umpawaug Rd, Redding, CT 06896

    Exquisite Nantucket-style country estate magnificently sited on seven sprawling acres in Redding, CT's coveted Umpawaug neighborhood. Comprised of three extraordinary residences, this masterfully crafted 2008 HOBI award-winning compound offers 13,904 sf of carefully constructed living space with meticulous architectural details, effortlessly balancing timeless elegance with modern function. The

    Lauren Parr Houlihan Lawrence

    206 Umpawaug Rd, Redding, CT 06896
  • /39

    $1,349,000

    $136K PRICE DROP
    • 5 Beds
    • 5 Baths
    • 6,170 Sq Ft

    281 Newtown Turnpike, Redding, CT 06896

    Set back off a private driveway, this exceptional custom-built 5-bedroom, 5-bathroom colonial is a "must-see" home. The seamless flow of the first floor, sprawling primary suite, private office with porch, and finished basement are just a few of the features that make this home truly exceptional. Showcasing generously proportioned rooms throughout over 6,000 sq ft of finished living space you

    Alexis Bennett Coldwell Banker Realty

    281 Newtown Turnpike, Redding, CT 06896
  • /40

    $4,500,000

    • 5 Beds
    • 8 Baths
    • 8,111 Sq Ft

    27 Old Oak Rd, Easton, CT 06612

    Custom built in 2022 by a top builder for his own family, this exceptional Easton residence offers a level of quality and execution rarely available. Set on 6.37 private acres on a quiet lane near Easton Center, the property combines refined design with a setting that feels more like Vermont countryside than suburban Connecticut. A rear gate provides direct access to Silverman's Farm, known for

    Andrew Whiteley Brown Harris Stevens

    27 Old Oak Rd, Easton, CT 06612
  • /39

    $1,275,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 2,935 Sq Ft

    18 Church St, Redding, CT 06896

    Known as the Aaron Davis House, ca. 1848, this exceptional historic Georgetown residence blends authenticity, artistic craftsmanship, and modern versatility in one of Redding's most cherished neighborhoods. Set on a beautifully landscaped property, it offers a rare opportunity to own a significant piece of local history while enjoying spaces thoughtfully adapted for contemporary living. Original

    Brianna Carvalho Compass Connecticut, LLC

    18 Church St, Redding, CT 06896
  • /31

    $849,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 1.5 Baths
    • 1,612 Sq Ft

    23 Church St, Wilton, CT 06897

    You'll love living in this bright and charming 3-bedroom, 1.5-bath updated antique Colonial located in Wilton's Historic District. Just a short walk to Georgetown's local eateries and Caraluzzi's, with easy access to both Wilton and Ridgefield town centers, this home offers the perfect blend of character, comfort, and convenience. Oversized windows fill the home with natural light, while the open

    Michele Ferguson Nichols Douglas Elliman of Connecticut

    23 Church St, Wilton, CT 06897
  • /36

    $929,000

    Open Sun 11:30AM - 1:30PM
    • 3 Beds
    • 3 Baths
    • 2,788 Sq Ft

    33 Topledge Rd, Redding, CT 06896

    Welcome to this well maintained 3-bedroom, 3-bath Colonial ideally situated on a quiet cul-de-sac with stunning front yard views and a peaceful setting. This spacious home offers an inviting layout designed for both comfortable living and entertaining. The sun-filled living room flows seamlessly into the formal dining room featuring a bay window overlooking the picturesque front yard. The custom

    Lynne Murphy Berkshire Hathaway NE Prop.

    33 Topledge Rd, Redding, CT 06896
  • /39

    $970,000

    • 5 Beds
    • 4 Baths
    • 4,344 Sq Ft

    270 Wilson Rd, Easton, CT 06612

    Set on a private, park-like 3 acre property this timeless 5-bedroom colonial offers the perfect blend of elegance, space, and outdoor living. Drive up the sweeping front circular driveway and be greeted by beautiful perennial flower beds and a tranquil koi pond with waterfall. Step into the welcoming foyer and be wowed by the openness. Head right to the charming front to back living room with

    Gayle Worthington William Raveis Real Estate

    270 Wilson Rd, Easton, CT 06612
  • /29

    $1,349,000

    Open Sat 1PM - 3PM
    • 3 Beds
    • 3.5 Baths
    • 2,598 Sq Ft

    301 Redding Rd, Easton, CT 06612

    Tucked away on 3 beautiful acres in Easton's sought-after Aspetuck neighborhood, is this charming cape style home with gorgeous curb appeal. With a portion of the property lying in Fairfield, you can also have town beach rights! This home offers the perfect blend of classic character and thoughtful updates. You'll find warm and inviting living spaces designed for everyday living and entertaining.

    Kelly Higgins Coldwell Banker Realty

    301 Redding Rd, Easton, CT 06612
  • /37

    $995,000

    Open Sat 11:30AM - 1:30PM
    • 5 Beds
    • 3.5 Baths
    • 2,204 Sq Ft

    127 Limekiln Rd, Redding, CT 06896

    Tucked behind a historic New England stone wall on 2.5 park-like acres, 127 Limekiln Road is a stunning 5-bedroom, 3.5-bath home commanding a magnificent presence. The exterior features a sweeping gravel driveway, detached 2-car garage, fieldstone chimney, copper gutters, a new cedar shingle roof, and a deep front porch. Inside, the bright and flexible floor plan is highlighted by a coveted

    Maureen Kitson William Pitt Sotheby's Int'l

    127 Limekiln Rd, Redding, CT 06896
  • /40

    $1,645,000

    Open Sun 1PM - 3PM $50K PRICE DROP
    • 4 Beds
    • 5 Baths
    • 4,786 Sq Ft

    74 George Hull Hill Rd, Redding, CT 06896

    Nestled on three picturesque acres and surrounded by open space, this beautiful country retreat offers privacy, comfort, and exceptional outdoor living. The expansive patio is perfect for entertaining, featuring a full outdoor kitchen, fireplace, TV, and integrated audio system. A large level yard provides plenty of space for recreation and the potential for a pool. Inside, the home showcases

    Tyler Toren Compass Connecticut, LLC

    74 George Hull Hill Rd, Redding, CT 06896

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