Homes for Sale near Joel Barlow High School

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  /40

  $910,000

  • 4 Beds
  • 3.5 Baths
  • 3,454 Sq Ft

  28 Winding Brook Ln, Redding, CT 06896

  Nestled on a quiet residential loop in one of Redding's desirable neighborhoods, this beautifully maintained 4-bedroom, 3 full and 1 half bath center hall Colonial offers timeless design, generous living space, and a secluded setting surrounded by mature landscaping. The gracious floor plan begins with a large living room that flows seamlessly into the formal dining room, where dramatic

  

  Heather Lindgren

  Coldwell Banker Realty

  28 Winding Brook Ln, Redding, CT 06896
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  Explore Joel Barlow High School

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  /30

  $749,000

  $50K PRICE DROP

  • 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

  125 Buck Hill Rd, Easton, CT 06612
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  /38

  $1,800,000

  Open Sat 10AM - 12PM Coming Soon

  • 4 Beds
  • 4.5 Baths
  • 6,108 Sq Ft

  24 Mark Twain Ln, Redding, CT 06896

  A once-in-a-generation offering. Once part of the Redding's historic Samuel Clemens (Mark Twain) estate, this extraordinary 5.41 acre property was later home to renowned American Abstract Expressionist painter Robert Natkin, whose creativity inspired its remarkable evolution. Set beside the 161-acre Stormfield Preserve, this secluded private compound offers miles of hiking trails just beyond your

  

  Heather Lindgren

  Coldwell Banker Realty

  24 Mark Twain Ln, Redding, CT 06896
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  /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

  

  Roni Agress

  William Pitt Sotheby's Int'l

  63 Turney Rd, Redding, CT 06896
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  /40

  $1,199,000

  • 4 Beds
  • 3.5 Baths
  • 2,954 Sq Ft

  44 Redding Rd, Easton, CT 06612

  Revive a bygone era in this enchanting circa 1924 estate, idyllically sited on 2.30 extraordinary acres along the scenic Aspetuck River. A classic white picket fence welcomes you to the Main House, surrounded by mature specimen trees, lush gardens, and breathtaking river views. Rich in history and timeless character, the residence showcases original architectural details, gracious living spaces,

  

  Susan Lieberman

  The Riverside Realty Group

  44 Redding Rd, Easton, CT 06612
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  /38

  $1,200,000

  • 4 Beds
  • 3.5 Baths
  • 4,102 Sq Ft

  170 Judd Rd, Easton, CT 06612

  Exceptional craftsmanship, timeless design, and a breathtaking natural setting define this extraordinary retreat. Nestled on a spectacular private property reminiscent of your own bird sanctuary, this home offers peace, privacy, and exceptional indoor-outdoor living. Wander through fragrant gardens, harvest fresh vegetables from your own garden, relax by the saltwater in-ground pool, unwind on

  

  Beth Saunders

  Berkshire Hathaway NE Prop.

  170 Judd Rd, Easton, CT 06612
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  /40

  $1,495,000

  $255K 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
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  /5

  $895,000

  Open Sun 1PM - 3PM Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,608 Sq Ft

  50 Deerfield Dr, Easton, CT 06612

  Beautifully sited on 3 private acres in Easton's Aspetuck Valley, this Center Hall Colonial lovingly maintained by its original owner, the home is now ready to welcome its next owner. Located on a friendly culdesac. The main level features a formal living room, dining room, and a spacious family room with a fireplace, perfect for gatherings. A large eatin kitchen anchors the home with generous

  Jackie Seawright William Pitt Sotheby's Int'l

  50 Deerfield Dr, Easton, CT 06612
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  /26

  $1,745,000

  $50K PRICE DROP

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

  2 Longwood Dr, Redding, CT 06896

  ***Rare turn-key opportunity at an unbeatable price point*** For buyers seeking exceptional craftmanship, serenity, a strong sense of community, award winning schools and uncompromised value. 2 Longwood Drive is a rare opportunity to purchase a 6,200+ square foot luxury home in southern Redding below recent comparable sales. Experience the exceptional lifestyle that has made Redding one of

  Jeffrey Kaplan William Raveis Real Estate

  2 Longwood Dr, Redding, CT 06896
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  /37

  $634,000

  • 4 Beds
  • 2 Baths
  • 1,632 Sq Ft

  70 Dayton Rd, Redding, CT 06896

  Welcome to your dream home, ideally located just steps from Devil's Den Park Trail. Set on nearly an acre of beautifully private land, this fully updated property offers the perfect blend of comfort, space, and modern style surrounded by nature. From the moment you arrive, you'll notice the brand-new roof, new siding, freshly painted interior, and rich hardwood floors that flow throughout the

  Nikolina Kajtazovic Coldwell Banker Realty

  70 Dayton Rd, Redding, CT 06896
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  /31

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 5,401 Sq Ft

  345 Rock House Rd, Easton, CT 06612

  Your own private estate on 3+ acres of beautifully landscaped grounds. Over 5,400 sq ft of elegant living space with a banquet-size formal dining room, chef's kitchen with adjoining family dining area and raised hearth stone fireplace, living room with second fireplace, generous family room, home office, sunroom with full bath and laundry, and a den opening to the patio, pool and sports courts

  John Hackett William Raveis Real Estate

  345 Rock House Rd, Easton, CT 06612
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  /7

  $749,500

  $146K 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
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  /40

  $4,749,000

  $250K PRICE DROP

  • 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
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  /2

  $975,000

  • Land
  • 7.57 Acres
  • $128,798 per Acre

  26&30 Goodsell Hill Rd, Redding, CT 06896

  Listing is for 2 previously approved building lots, 4.09 acres and 3.479 acres. Lots have been rough graded, 2 septic's installed, build your dream house, build 2 homes, horse property? property tax is combined amounts of both lots. More photos to come

  Chris Robinson Independent Realty Group

  26&30 Goodsell Hill Rd, Redding, CT 06896
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  /40

  $1,075,000

  • 3 Beds
  • 3.5 Baths
  • 2,754 Sq Ft

  149 Old Redding Rd, Redding, CT 06896

  Imagine a home where the air is fresh & the pace of life slows. This is a true nature lover's retreat, just 60 miles from NYC. This gem underwent a total rebuild in 2003, resulting in a home that feels both timeless & entirely current. The professionally landscaped grounds burst with color and texture, creating a seamless connection between the indoors & the gorgeous natural landscape.At the

  Peggy Jorgensen Compass Connecticut, LLC

  149 Old Redding Rd, Redding, CT 06896
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  /36

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 3,124 Sq Ft

  207 Redding Rd, Redding, CT 06896

  Classic New England charm meets modern luxury in this beautifully updated 1921 Colonial. Perfectly situated just minutes from the quaint Georgetown boutique shops , restaurants, and Route 7. Set on nearly half an acre lot, this home offers effortless living and entertaining inside and out. The heart of the home features a renovated eat-in kitchen with timeless marble countertops, a 4 seated

  Kate White Houlihan Lawrence

  207 Redding Rd, Redding, CT 06896
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  /39

  $649,900

  • 3 Beds
  • 3 Baths
  • 1,795 Sq Ft

  101 Sport Hill Rd, Easton, CT 06612

  This is a move-in-ready, well-maintained Cape Cod-style home which offers a rare combination of updates, functionality, and classic charm in Lower Easton. Ideally located with convenient access to the Merritt Parkway, shopping, and local amenities, the home provides an easy lifestyle in one of the area's most desirable communities. A stone exterior and circular driveway create a welcoming first

  Katiria Chiluisa RE/MAX Right Choice

  101 Sport Hill Rd, Easton, CT 06612
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  /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
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  /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
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  /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
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  /39

  $1,395,000

  $100K PRICE DROP

  • 5 Beds
  • 6 Baths
  • 6,775 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
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  /9

  $1,539,000

  • 2 Beds
  • 2.5 Baths
  • 2,660 Sq Ft

  250 Maple Rd, Easton, CT 06612

  Beautiful Property - LIKE YELLOWSTONE? This "mini-Yellowstone" borders almost 150 acres of groomed horseback/hiking trails -located in Easton - the "Black Pearl" of Fairfield County. Gated access to 3 open acres with thousand feet plus of stone walls and 4 grassed fenced pastures. Featuring a custom ranch/cape with 2 master suites on the main floor. Setup to easily expand to 4 bedrooms and 5

  Steven Koleno Beycome of Connecticut

  250 Maple Rd, Easton, CT 06612
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  /40

  $1,300,000

  • 4 Beds
  • 3.5 Baths
  • 3,005 Sq Ft

  974 Black Rock Turnpike, Easton, CT 06612

  Sited on just under 5 private, wooded acres across from the CT Golf Club - this architecturally unique home is truly above par! Light & bright 4BR colonial with so many special features, including a 1200+SF studio above the detached garage. The kitchen, family & breakfast room create a superior open space for gathering & entertaining - all open to an expansive private rear deck and firepit with

  Patricia Prenderville Higgins Group Real Estate

  974 Black Rock Turnpike, Easton, CT 06612
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  /40

  $1,275,000

  • 4 Beds
  • 3.5 Baths
  • 4,548 Sq Ft

  28 Drewbarrie Ln, Easton, CT 06612

  More than just a home, 28 Drewbarrie Lane was thoughtfully designed to be the place its owners would never want to leave. Privately set among mature trees in one of Easton's most peaceful settings, it offers a lifestyle centered around comfort, connection, and enjoying every season to its fullest. Mornings begin with sunlight filling the living spaces, afternoons are spent by the solar-heated

  Michael Caporizzo William Pitt Sotheby's Int'l

  28 Drewbarrie Ln, Easton, CT 06612
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  /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
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  /40

  $1,395,000

  $33K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 4,069 Sq Ft

  30 Carriage Dr, Easton, CT 06612

  A destination unto itself, this exceptional custom-built Scholz Design Colonial offers a rare blend of luxury, privacy, and natural beauty. Tucked away at the end of a picturesque cul-de-sac and bordering 153 acres of protected open space and hiking trails, this nearly four-acre estate provides an unparalleled retreat just minutes from town amenities. A dramatic two-story foyer opens to a

  Nicole Costantino Keller Williams Realty

  30 Carriage Dr, Easton, CT 06612
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  /38

  $1,245,000

  • 4 Beds
  • 5.5 Baths
  • 5,935 Sq Ft

  11 Long Meadow Ln, Redding, CT 06896

  Private Cul-de-Sac Colonial on 2.95 Acres in Redding! Desirable custom-built Center Hall Colonial privately set at the end of a cul-de-sac abutting protected Green Acres land for exceptional privacy and natural beauty. Professionally landscaped with classic stone walls and mature trees, picturesque views of neighboring horse property and ample space for a pool and tennis court. A dramatic

  Ira Stone Coldwell Banker Realty

  11 Long Meadow Ln, Redding, CT 06896
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  /40

  $1,500,000

  • 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
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  /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
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  /35

  $1,350,000

  $149K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,768 Sq Ft

  1080 Black Rock Turnpike, Easton, CT 06612

  Set behind a stately gated entrance on nearly six acres of exquisitely landscaped grounds, 1080 Black Rock Turnpike is a private Easton estate where timeless elegance meets modern refinement. Completely renovated with exceptional craftsmanship and meticulous attention to detail, the residence offers a seamless blend of luxury, comfort, and sophistication. A winding driveway leads to a home

  Ryan Ciambriello Houlihan Lawrence

  1080 Black Rock Turnpike, Easton, CT 06612
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  /40

  $975,000

  • 3 Beds
  • 2 Baths
  • 3,772 Sq Ft

  93 Tersana Dr, Easton, CT 06612

  Recently reimagined with exceptional updates and curated for today's lifestyle, this stunning Lower Easton residence seamlessly blends timeless elegance with modern comfort. Privately set on a picturesque lot in one of Easton's most desirable neighborhoods, this beautifully renovated 3-bedroom, 2-bath home is the definition of move-in ready. A light-filled open-concept design showcases gleaming

  Nicole Costantino Keller Williams Realty

  93 Tersana Dr, Easton, CT 06612
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  /34

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,688 Sq Ft

  78 Black Rock Turnpike, Redding, CT 06896

  Discover the quintessential Redding lifestyle in this charming circa 1898 home, perfectly positioned to enjoy the town's excellent schools, open space, and recreational opportunities like hiking, fishing, and kayaking. This 2/3 bedroom (3rd bedroom being used as a study) residence features a 3-bedroom septic system, central air and 2 full bathrooms, offering versatile living options. Step inside

  Lisa Pompeo William Pitt Sotheby's Int'l

  78 Black Rock Turnpike, Redding, CT 06896
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  /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
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  /39

  $1,295,000

  $190K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 6,170 Sq Ft

  281 Newtown Turnpike, Redding, CT 06896

  Exceptional opportunity for today's buyer! Tucked away in a private, yet neighborhood-like setting, the craftsmanship and beauty of this custom colonial reveals itself the moment you walk through the door. Seamless flow, a sprawling primary suite with fireplace, private office with built-ins and French doors that lead to a porch, as well as a finished basement are just a few of the features that

  Alexis Bennett Coldwell Banker Realty

  281 Newtown Turnpike, Redding, CT 06896
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  /27

  $499,000

  $40K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 930 Sq Ft

  71 Picketts Ridge Rd, Redding, CT 06896

  Tucked away like a storybook retreat, 71 Picketts Ridge is a charming and cozy ranch-style home that lives like a private condo alternative, set on two secluded acres and reached by a long, winding driveway that opens to the peaceful serenity of the woods. Surrounded by nature and complete privacy, this special property offers the perfect blend of tranquility and convenience. Recently remastered

  Kyle Neumann Houlihan Lawrence

  71 Picketts Ridge Rd, Redding, CT 06896
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  /40

  $3,995,000

  $505K PRICE DROP

  • 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
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  /39

  $1,275,000

  • 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
• 

  

  /40

  $1,150,000

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft

  33 Old Stagecoach Rd, Redding, CT 06896

  Turn Key completely Renovated down to the studs! This 4-bed, 3.5-bath Cape Cod farm style home has 3400 SqFT.. New Roof, electrical, plumbing, HVAC & more! Entering notice a beautiful open floor plan w/ expansive natural light, w/ new hardwd floors through out. Main attraction.. the beautiful Kitchen! The white quartz countertops, waterfall island w/ plenty of seating, 2 tone color cabinets,

  Jay Irvine Serhant Connecticut, LLC

  33 Old Stagecoach Rd, Redding, CT 06896
• 

  

  /40

  $999,500

  Open Sat 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 4,924 Sq Ft

  380 Black Rock Turnpike, Redding, CT 06896

  Privately set back from the road on 2.94 wooded acres, this spacious Redding Colonial offers versatile living space, treetop views, and a layout designed for both everyday comfort and entertaining. The light-filled main level features an inviting family room with a gas fireplace, built-ins, and French doors opening to a private deck and backyard. At the heart of the home, the eat-in kitchen

  Jeff Neumann Houlihan Lawrence

  380 Black Rock Turnpike, Redding, CT 06896
• 

  

  /40

  $5,249,000

  $250K PRICE DROP

  • 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 15 acres with a lake and separate building lot-ideal for equestrian pursuits or 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

  Linda Toscano Coldwell Banker Realty

  294 Maple Rd, Easton, CT 06612

Showing Results 1 - 40, Page 1 of 2