Redding, CT Homes

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  /38

  $1,800,000

  • 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
• Explore Redding

• 

  

  

  /16

  $3,300 Per Month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • House for Rent

  3 Sidecut Rd Unit B, Redding, CT 06896

  Brand New! The building just rebuilt from the ground up! 2 spacious bedrooms with en-suite primary bath featuring a large tiled rain-shower and European appointments. Closets have organizers built-in. European influence continues in the modern kitchen set at the end of the great room featuring a light and bright windowed wall and french door stepping out to a private balcony/deck overlooking the

  Sharon Hoverman Coldwell Banker Realty

  3 Sidecut Rd Unit B, Redding, CT 06896
• 

  $549,000

  Sold May 01, 2026

  64 Portland Ave, Redding, CT 06896

  • 2 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1995

  Last Sold Summary

  • $281/SF
  • 71 Days On Market

  Current Estimated Value $557,575

  Last Listing Agent Alexis Bennett Coldwell Banker Realty

  64 Portland Ave, Redding, CT 06896
• 

  Est $936,768

  Not Listed For Sale

  12 Winding Brook Ln, Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 3,019 Sq Ft
  • Built 1971

  12 Winding Brook Ln, Redding, CT 06896

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Annmarie Del Franco Blackstone Properties of CT
• 

  

  

  /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
• 

  

  /27

  $13,000 Per Month

  • 3 Beds
  • 2 Baths
  • 3,004 Sq Ft
  • House for Rent

  26 Chalburn Rd, Redding, CT 06896

  The Otnes House is a true floating oasis and now available as a summer rental! This rolling property overlooks nearly 3.5 acres, complete with a one-of-a-kind pool carved into a natural stone quarry with beautiful surrounding gardens. John Johansen of the celebrated Harvard Five designed this mid-century modern for famous collage artist Fred Otnes, who lived here for over 50 years. Walls of glass

  Alexandra Friedman Compass Connecticut, LLC

  26 Chalburn Rd, Redding, CT 06896
• 

  $1,170,000

  Sold Jan 29, 2026

  15 Tunxis Trail, Redding, CT 06896

  • 4 Beds
  • 2.5 Baths
  • 4,081 Sq Ft
  • Built 1983

  Last Sold Summary

  • 10% Above List Price
  • $287/SF
  • 35 Days On Market

  Current Estimated Value $1,199,221

  Last Listing Agent Christine Poppy Compass Connecticut, LLC

  15 Tunxis Trail, Redding, CT 06896
• 

  Not Listed For Sale

  22 Woods Way Unit 22, Redding, CT 06896

  • 3 Beds
  • 2.5 Baths
  • 2,022 Sq Ft
  • Built 2000

  22 Woods Way Unit 22, Redding, CT 06896

  Last Sold Summary

  • 55 Days On Market

  Last Listing Agent Sandra Juliano Berkshire Hathaway NE Prop.
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  /38

  $1,585,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,294 Sq Ft

  15 Silversmith Ln, Redding, CT 06896

  Artisan Craftsmanship Meets Modern Autonomy - Your Private Oasis Awaits! Nestled on 4 idyllic, professionally landscaped acres at the end of a quiet cul-de-sac, this spectacular 2002 post-and-beam is a perfect blend of artisan craftsmanship and modern design. Built to exacting standards, this "one-of-a-kind" residence presents a dramatic, flexible open floor plan bathed in natural light through

  

  Roni Agress

  William Pitt Sotheby's Int'l

  15 Silversmith Ln, Redding, CT 06896
• 

  

  /11

  $2,750 Per Month

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • House for Rent

  150A Lonetown Rd, Redding, CT 06896

  Be pleasantly surprised as you step into this spacious studio apartment set above a three-car garage. The thoughtfully designed contemporary space features an open floor plan, soaring ceilings, and expansive windows that bathe the interior in natural light. Enjoy the perfect balance of convenience and tranquility-privately tucked away down a long driveway, offering a quiet retreat with beautiful,

  Helen Cusa Brown Harris Stevens

  150A Lonetown Rd, Redding, CT 06896
• 

  $775,000

  Sold Oct 31, 2025

  181 Picketts Ridge Rd, Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 2,420 Sq Ft
  • Built 1973

  Last Sold Summary

  • 3% Below List Price
  • $320/SF
  • 28 Days On Market

  Current Estimated Value $803,028

  Last Listing Agent Kristi Vaughan William Pitt Sotheby's Int'l

  181 Picketts Ridge Rd, Redding, CT 06896
• 

  Est $1,303,461

  Not Listed For Sale

  130 Picketts Ridge Rd, Redding, CT 06896

  • 3 Beds
  • Built 1929

  130 Picketts Ridge Rd, Redding, CT 06896

  Last Sold Summary

  • 514 Days On Market

  Last Listing Agent Tom Thomas Coldwell Banker Realty
• 

  

  /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
• 

  

  /15

  $3,150 Per Month

  • 3 Beds
  • 1 Bath
  • 802 Sq Ft
  • House for Rent

  73 Simpaug Turnpike, Redding, CT 06896

  Totally renovated inside and out -all new appliances, new flooring, paint, etc. The garage will be removed prior to tenancy. Please note that the town line divides the property address is Redding house is located in Ridgefield

  Peter Hastings Hastings Real Estate

  73 Simpaug Turnpike, Redding, CT 06896
• 

  $1,700,000

  Sold Sep 15, 2025

  9 Long Meadow Ln, Redding, CT 06896

  • 4 Beds
  • 5 Baths
  • 5,098 Sq Ft
  • Built 1997

  Last Sold Summary

  • 6% Above List Price
  • $333/SF
  • 31 Days On Market

  Current Estimated Value $1,767,168

  Last Listing Agent Jessica Brookbanks Coldwell Banker Realty

  9 Long Meadow Ln, Redding, CT 06896
• 

  Est $316,824

  Not Listed For Sale

  659 Redding Rd, Redding, CT 06896

  659 Redding Rd, Redding, CT 06896

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Kris Kling Compass Connecticut, LLC
• 

  

  /40

  $3,950,000

  Pending

  • 6 Beds
  • 5.5 Baths
  • 3,264 Sq Ft

  240 Umpawaug Rd, Redding, CT 06896

  Steeped in history and natural beauty, the Charles Ives House (ca. 1913) is a masterfully restored 18-acre West Redding summer retreat where the famed modernist composer lived and created his signature works. Designed and built by Ives himself, this iconic Arts and Crafts estate seamlessly pairs vintage authenticity with ultra-luxury modern updates. Inside, original architectural integrity

  

  Roni Agress

  William Pitt Sotheby's Int'l

  240 Umpawaug Rd, Redding, CT 06896
• 

  

  /40

  $15,000 Per Month

  • 4 Beds
  • 4.5 Baths
  • 3,350 Sq Ft
  • House for Rent

  142 Seventy Acre Rd, Redding, CT 06896

  Privately nestled on over three spectacular acres, this exceptional gated 5 bed/4 bath estate delivers a lifestyle rarely found in Fairfield County. Blending striking architectural design with warm, inviting living spaces, the residence was crafted for both elevated entertaining and everyday comfort.Inside, soaring vaulted ceilings, expansive walls of glass, and dramatic open-concept spaces

  Erin Melson The Agency

  142 Seventy Acre Rd, Redding, CT 06896
• 

  $905,000

  Sold Jul 09, 2026

  81 Pinetree Rd, Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 2,436 Sq Ft
  • Built 1900

  Last Sold Summary

  • 10% Above List Price
  • $372/SF
  • 25 Days On Market

  Current Estimated Value $817,608

  Last Listing Agent Brianna Carvalho Compass Connecticut, LLC

  81 Pinetree Rd, Redding, CT 06896
• 

  Est $1,163,227

  Not Listed For Sale

  158 Old Redding Rd, Redding, CT 06896

  • 4 Beds
  • 4.5 Baths
  • 3,200 Sq Ft
  • Built 2025

  158 Old Redding Rd, Redding, CT 06896

  Last Sold Summary

  • 47 Days On Market

  Last Listing Agent John Frey Coldwell Banker Realty
• 

  

  /26

  $1,675,000

  $120K PRICE DROP

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

  2 Longwood Dr, Redding, CT 06896

  ***NEW PRICE*** $1,675,000! MORE HOUSE. MORE LAND. MORE PRIVACY. EXCEPTIONAL VALUE. If you've been searching Westchester or Fairfield County for a quintessential country estate that gives you substantial space without sacrificing access to the NYC metropolitan area, this exceptional custom built Redding Colonial deserves your attention. Offering 6,259 square feet, 2.72 private acres, 4 bedrooms,

  Jeffrey Kaplan William Raveis Real Estate

  2 Longwood Dr, Redding, CT 06896
• 

  $779,000

  Sold Sep 03, 2025

  731 N Park Ave, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 3,306 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $236/SF
  • 52 Days On Market

  Current Estimated Value $889,666

  Last Listing Agent Kelly Higgins Coldwell Banker Realty

  731 N Park Ave, Redding, CT 06896
• 

  Est $2,072,269

  Not Listed For Sale

  1 Chestnut Woods Rd, Redding, CT 06896

  • 3 Beds
  • 3 Baths
  • 2,783 Sq Ft
  • Built 2021

  1 Chestnut Woods Rd, Redding, CT 06896

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Karla Murtaugh Compass Connecticut, LLC
• 

  

  /37

  $624,000

  $10K PRICE DROP Under Contract

  • 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
• 

  $800,000

  Sold Nov 12, 2025

  1 Long Wall Rd, Redding, CT 06896

  • 5 Beds
  • 3 Baths
  • 5,176 Sq Ft
  • Built 1950

  Last Sold Summary

  • 1% Above List Price
  • $155/SF
  • 79 Days On Market

  Current Estimated Value $849,952

  Last Listing Agent William Whitehead Berkshire Hathaway NE Prop.

  1 Long Wall Rd, Redding, CT 06896
• 

  Est $752,513

  Not Listed For Sale

  7 Simpaug Turnpike, Ridgefield, CT 06877

  • 3 Beds
  • 2 Baths
  • 1,828 Sq Ft
  • Built 1955

  7 Simpaug Turnpike, Ridgefield, CT 06877

  Last Sold Summary

  • 85 Days On Market

  Last Listing Agent Svetlana Mastrogiannis William Raveis Real Estate
• 

  

  /40

  $1,495,000

  • 6 Beds
  • 5 Baths
  • 4,033 Sq Ft

  12 Werf Dr, Redding, CT 06896

  Extraordinary, beautifully updated six-bedroom Colonial, where timeless architecture meets modern luxury. Set on an impressive 2.42-acre estate, this property offers a rare blend of privacy, scale, and refined presence creating a true retreat just moments from everyday conveniences. A sweeping wraparound driveway delivers a grand and memorable arrival, complementing the home's stately facade

  Jonathan Gineo Silver and Oak Realty

  12 Werf Dr, Redding, CT 06896
• 

  $900,000

  Sold Jun 23, 2026

  19 Marchant Rd, Redding, CT 06896

  • 3 Beds
  • 3 Baths
  • 3,514 Sq Ft
  • Built 1993

  Last Sold Summary

  • 14% Below List Price
  • $256/SF
  • 46 Days On Market

  Current Estimated Value $985,835

  Last Listing Agent Luke Eddinger Robert C White & Company LLC

  19 Marchant Rd, Redding, CT 06896
• 

  Est $1,521,912

  Not Listed For Sale

  38 Goodsell Hill Rd, Redding, CT 06896

  • 5 Beds
  • 6 Baths
  • 6,515 Sq Ft
  • Built 2006

  38 Goodsell Hill Rd, Redding, CT 06896

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Ellen Steckler Houlihan Lawrence
• 

  

  /5

  $305,000

  • Land
  • 3.69 Acres
  • $82,656 per Acre

  162 Lonetown Rd, Redding, CT 06896

  A wonderful opportunity in the Putnam Park neighborhood of bucolic Redding Connecticut. Bring your dream home to life on 3.69 acres of raw undeveloped land. Potentially build to suit or buy direct. Previously an approved building lot for a 4 Bedroom home with a pool. Approximately one acre partially cleared and has a deeded right of way for access to a beautiful wooded rear lot. This is your

  Adam Roy BHGRE Gaetano Marra Homes

  162 Lonetown Rd, Redding, CT 06896
• 

  $1,600,000

  Sold Nov 18, 2025

  35 Diamond Hill Rd, Redding, CT 06896

  • 5 Beds
  • 3 Baths
  • 3,407 Sq Ft
  • Built 1972

  Last Sold Summary

  • 7% Above List Price
  • $470/SF
  • 6 Days On Market

  Last Listing Agent Tanya Sprague Coldwell Banker Realty

  35 Diamond Hill Rd, Redding, CT 06896
• 

  Est $757,640

  Not Listed For Sale

  101 Peaceable St, Redding, CT 06896

  • 2 Beds
  • 2 Baths
  • 1,486 Sq Ft
  • Built 2008

  101 Peaceable St, Redding, CT 06896

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Connie Widmann William Raveis Real Estate
• 

  

  /26

  $769,900

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,576 Sq Ft

  429 Rock House Rd, Redding, CT 06896

  Privately set on a serene back lot, this spacious 4-Bedroom, 2.5-Bath Colonial offers the perfect blend of classic charm and everyday comfort. Gleaming Hardwood Floors run throughout the home - excluding the Kitchen and Baths - adding warmth and continuity to the well designed layout. The Main Level features a gracious Formal Living Room with stately FP and Slider access to the expansive,

  T.R. Durkin William Raveis Real Estate

  429 Rock House Rd, Redding, CT 06896
• 

  $1,020,000

  Sold Dec 03, 2025

  194 Lonetown Rd, Redding, CT 06896

  • 5 Beds
  • 3.5 Baths
  • 3,181 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $321/SF
  • 68 Days On Market

  Current Estimated Value $1,056,608

  Last Listing Agent David Landau RE/MAX Right Choice

  194 Lonetown Rd, Redding, CT 06896
• 

  Est $1,450,710

  Not Listed For Sale

  21 Long Wall Rd, Redding, CT 06896

  • 4 Beds
  • 5 Baths
  • 5,598 Sq Ft
  • Built 2001

  21 Long Wall Rd, Redding, CT 06896

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Sarah Fair William Raveis Real Estate
• 

  /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
• 

  $408,000

  Sold Feb 19, 2026

  280 Newtown Turnpike, Redding, CT 06896

  • 2 Beds
  • 1 Bath
  • 1,035 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $394/SF
  • 5 Days On Market

  Current Estimated Value $433,029

  Last Listing Agent Harry Stark William Raveis Real Estate

  280 Newtown Turnpike, Redding, CT 06896
• 

  Est $1,251,612

  Not Listed For Sale

  17 Long Wall Rd, Redding, CT 06896

  • 4 Beds
  • 4.5 Baths
  • 5,000 Sq Ft
  • Built 2002

  17 Long Wall Rd, Redding, CT 06896

  Last Sold Summary

  • 59 Days On Market

  Last Listing Agent Kim Vartuli Keller Williams Realty
• 

  

  /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
• 

  $975,000

  Sold May 21, 2026

  45 Great Pasture Rd, Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 3,982 Sq Ft
  • Built 1745

  Last Sold Summary

  • 15% Above List Price
  • $245/SF
  • 277 Days On Market

  Current Estimated Value $1,088,075

  Last Listing Agent Joe Scozzafava William Raveis Real Estate

  45 Great Pasture Rd, Redding, CT 06896

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