Redding, CT Homes

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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
• 

  $1,200,000

  Sold Jul 15, 2026

  5 Musket Ln, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 3,650 Sq Ft
  • Built 1976

  Last Sold Summary

  • 2% Above List Price
  • $329/SF
  • 49 Days On Market

  Current Estimated Value $1,159,643

  Last Listing Agent Michael McKee William Pitt Sotheby's Int'l

  5 Musket Ln, Redding, CT 06896
• 

  Est $1,139,480

  Not Listed For Sale

  75 Stepney Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 3,998 Sq Ft
  • Built 2004

  75 Stepney Rd, Redding, CT 06896

  Last Sold Summary

  • 31 Days On Market

  Last Listing Agent Laura Ancona William Pitt Sotheby's Int'l
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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
• 

  $1,675,000

  Sold Sep 03, 2025

  279 Black Rock Turnpike, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 4,495 Sq Ft
  • Built 1820

  Last Sold Summary

  • 4% Below List Price
  • $373/SF
  • 267 Days On Market

  Last Listing Agent Karla Murtaugh Compass Connecticut, LLC

  279 Black Rock Turnpike, Redding, CT 06896
• 

  Est $451,660

  Not Listed For Sale

  779 N Park Ave, Redding, CT 06896

  • 4 Beds
  • 1.5 Baths
  • 928 Sq Ft
  • Built 1955

  779 N Park Ave, Redding, CT 06896

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Jonathan Gineo Silver and Oak Realty
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  /27

  $499,000

  $40K PRICE DROP Pending

  • 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
• 

  $812,500

  Sold Nov 10, 2025

  29 Meeker Hill Rd, Redding, CT 06896

  • 4 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Built 1971

  Last Sold Summary

  • 7% Above List Price
  • $431/SF
  • 5 Days On Market

  Current Estimated Value $846,189

  Last Listing Agent JaKeith Action Jackson ASJ Realty Partners

  29 Meeker Hill Rd, Redding, CT 06896
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  Est $707,000

  Not Listed For Sale

  118 Mountain Rd, Redding, CT 06896

  • 5 Beds
  • 7 Baths
  • 7,162 Sq Ft
  • Built 1900

  118 Mountain Rd, Redding, CT 06896

  Last Sold Summary

  • 128 Days On Market

  Last Listing Agent Karla Murtaugh Compass Connecticut, LLC
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  /38

  $1,100,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,525 Sq Ft

  123 Cross Hwy, Redding, CT 06896

  Beautiful and serene, this special property has been lovingly maintained by the same family for the past 37 years. Set on 6.18 picturesque acres in a desirable neighborhood surrounded by other expansive properties, the 4 bedroom, 3.5 bath home offers privacy, space, and a wonderful sense of tranquility. Well maintained throughout, the home features thoughtful updates, including a roof that is

  Nicole Van Alsytne William Pitt Sotheby's Int'l

  123 Cross Hwy, Redding, CT 06896
• 

  $940,000

  Sold Mar 30, 2026

  22 Ledgewood Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 3,578 Sq Ft
  • Built 1976

  Last Sold Summary

  • 4% Below List Price
  • $263/SF
  • 150 Days On Market

  Current Estimated Value $967,059

  Last Listing Agent Barbara Pincione Houlihan Lawrence

  22 Ledgewood Rd, Redding, CT 06896
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  Est $678,026

  Not Listed For Sale

  32 Mountain Rd, Redding, CT 06896

  • 3 Beds
  • 1.5 Baths
  • 1,400 Sq Ft
  • Built 1914

  32 Mountain Rd, Redding, CT 06896

  Last Sold Summary

  • 241 Days On Market

  Last Listing Agent Chip Parrish Keller Williams Realty
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  /31

  $849,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,612 Sq Ft

  23 Church St, Wilton, CT 06897

  Back on the market through no fault of the home! Due to the previous buyers' inability to close, this exceptional property is available once again. Nestled in Wilton's Historic District, this beautifully updated 3-bedroom, 1.5-bath antique Colonial has been featured in The New York Times, Realtor.com, & Homes.com for its distinctive character & timeless appeal. Just a short stroll to Georgetown's

  Michele Ferguson Nichols Douglas Elliman of Connecticut

  23 Church St, Wilton, CT 06897
• 

  $810,000

  Sold Jul 14, 2026

  35 Deer Spring Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 2,912 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Above List Price
  • $278/SF
  • 41 Days On Market

  Current Estimated Value $805,578

  Last Listing Agent Laura Ancona William Pitt Sotheby's Int'l

  35 Deer Spring Rd, Redding, CT 06896
• 

  Est $797,477

  Not Listed For Sale

  43 Pine Mountain Rd, Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 2,931 Sq Ft
  • Built 1969

  43 Pine Mountain Rd, Redding, CT 06896

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Joanne Grasso Coldwell Banker Realty
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  /39

  $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
• 

  $599,000

  Sold Oct 10, 2025

  Unlisted Address

  • 5 Beds
  • 3 Baths
  • 2,639 Sq Ft
  • Built 1968

  Last Sold Summary

  • 13% Below List Price
  • $227/SF
  • 139 Days On Market

  Current Estimated Value $670,445

  Last Listing Agent Sharon Hoverman Coldwell Banker Realty

  Unlisted Address
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  Est $628,562

  Not Listed For Sale

  30 Pine Mountain Rd, Redding, CT 06896

  • 3 Beds
  • 1.5 Baths
  • 1,597 Sq Ft
  • Built 1965

  30 Pine Mountain Rd, Redding, CT 06896

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Debbie Blum William Raveis Real Estate
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  /40

  $999,500

  • 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
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  $1,600,000

  Sold Sep 26, 2025

  171 Cross Hwy, Redding, CT 06896

  • 4 Beds
  • 4 Baths
  • 5,072 Sq Ft
  • Built 2001

  Last Sold Summary

  • 6% Below List Price
  • $315/SF
  • 95 Days On Market

  Current Estimated Value $1,664,584

  Last Listing Agent Laura Ancona William Pitt Sotheby's Int'l

  171 Cross Hwy, Redding, CT 06896
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  Est $1,276,119

  Not Listed For Sale

  24 Pine Mountain Rd, Redding, CT 06896

  • 4 Beds
  • 4 Baths
  • 4,482 Sq Ft
  • Built 1969

  24 Pine Mountain Rd, Redding, CT 06896

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Brianna Carvalho Compass Connecticut, LLC
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  /40

  $1,595,000

  $100K PRICE DROP Pending

  • 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
• 

  $1,195,000

  Sold May 28, 2026

  19 Mine Hill Rd, Redding, CT 06896

  • 5 Beds
  • 3.5 Baths
  • 4,407 Sq Ft
  • Built 1983

  Last Sold Summary

  • $271/SF
  • 16 Days On Market

  Current Estimated Value $1,174,225

  Last Listing Agent Chuck Ciambriello Coldwell Banker Realty

  19 Mine Hill Rd, Redding, CT 06896
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  Est $1,042,681

  Not Listed For Sale

  11 Seventy Acre Rd, Redding, CT 06896

  • 5 Beds
  • 4 Baths
  • 3,683 Sq Ft
  • Built 1948

  11 Seventy Acre Rd, Redding, CT 06896

  Last Sold Summary

  • 118 Days On Market

  Last Listing Agent Jeff Turner eXp Realty
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  /21

  $549,000

  • 2 Beds
  • 2 Baths
  • 1,125 Sq Ft

  19 Olmstead Rd, Redding, CT 06896

  If you want to enjoy all that Redding has to offer without the upkeep of a large home and expansive yard, this charming home may be just what you're looking for. Located in a quiet West Redding neighborhood, this home sits on an inviting corner lot and offers classic New England character throughout. As you enter through the enclosed front porch, you're welcomed by a wonderful sense of charm. The

  James Millington William Raveis Real Estate

  19 Olmstead Rd, Redding, CT 06896
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  $705,000

  Sold May 27, 2026

  101 Sport Hill Rd, Redding, CT 06896

  • 2 Beds
  • 2 Baths
  • 2,294 Sq Ft
  • Built 1953

  Last Sold Summary

  • 1% Above List Price
  • $307/SF
  • 53 Days On Market

  Current Estimated Value $715,947

  Last Listing Agent Nicholas Wilson Coldwell Banker Realty

  101 Sport Hill Rd, Redding, CT 06896
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  Est $660,711

  Not Listed For Sale

  74 Old Redding Rd, Redding, CT 06896

  • 3 Beds
  • 2.5 Baths
  • 2,540 Sq Ft
  • Built 1966

  74 Old Redding Rd, Redding, CT 06896

  Last Sold Summary

  • 46 Days On Market

  Last Listing Agent Patrick Russo Berkshire Hathaway NE Prop.
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  /39

  $1,695,000

  Pending

  • 5 Beds
  • 5.5 Baths
  • 5,308 Sq Ft

  110 Sport Hill Rd, Redding, CT 06896

  A rare blend of scale, privacy and value, this beautifully maintained Redding retreat offers over 6,000 square feet of flexible living space. From the gracious front entry, the home unfolds with purpose and ease. To the right, a private library/home office creates a quiet place to work. Straight ahead, the living room frames peaceful views of the pool and grounds, while the formal dining room

  Tara Hawley Coldwell Banker Realty

  110 Sport Hill Rd, Redding, CT 06896
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  $1,025,000

  Sold Sep 02, 2025

  149 Limekiln Rd, Redding, CT 06896

  • 5 Beds
  • 2.5 Baths
  • 3,217 Sq Ft
  • Built 1767

  Last Sold Summary

  • 15% Below List Price
  • $319/SF
  • 124 Days On Market

  Current Estimated Value $1,093,648

  Last Listing Agent Chadwick Ciocci Higgins Group Greenwich

  149 Limekiln Rd, Redding, CT 06896
• 

  Est $1,313,310

  Not Listed For Sale

  12 Old Redding Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 2,336 Sq Ft
  • Built 1987

  12 Old Redding Rd, Redding, CT 06896

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Susan O'rourke Brown Harris Stevens
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  /40

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 2,819 Sq Ft

  Unlisted Address

  Stunningly renovated Vintage Antique. Up-to-date and yet still very authentic with beams and wide board floors. Set on over 2 level Acres ringed by trees for privacy; includes a lofted barn with possible potential to convert to a 1 BR guest ctg. The kitchen with new stainless appliances, granite and wood floors steps down to the cozy family rm warmed with a wood burning stove, built-in window

  Sharon Hoverman Coldwell Banker Realty

  Unlisted Address
• 

  $1,225,000

  Sold Jul 30, 2026

  40 Deer Hill Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 3,690 Sq Ft
  • Built 1988

  Last Sold Summary

  • 9% Above List Price
  • $332/SF
  • 18 Days On Market

  Current Estimated Value $1,117,824

  Last Listing Agent Brianna Carvalho Compass Connecticut, LLC

  40 Deer Hill Rd, Redding, CT 06896
• 

  Est $610,837

  Not Listed For Sale

  2 Old Redding Rd, Redding, CT 06896

  • 2 Beds
  • 2 Baths
  • 999 Sq Ft
  • Built 1948

  2 Old Redding Rd, Redding, CT 06896

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Dena Chelednik Houlihan Lawrence
• 

  

  /40

  $1,100,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 4,614 Sq Ft

  121 Picketts Ridge Rd, Redding, CT 06896

  Welcome to 121 Picketts Ridge Road in beautiful West Redding/ Picketts Ridge! This custom built home is the perfect family compound, sitting on massive 2.38 park-like acres. Enjoy level side-by-side, single level living with this Ranch separated by the 3 car garage. The sprawling family room and 2nd level bonus space loft can be used for either unit or as shared space for big/ multigenerational

  Brian Appel Higgins Group Real Estate

  121 Picketts Ridge Rd, Redding, CT 06896
• 

  $575,000

  Sold Oct 29, 2025

  6 Old Mailcoach Rd, Redding, CT 06896

  • 2 Beds
  • 1.5 Baths
  • 842 Sq Ft
  • Built 1900

  Last Sold Summary

  • 10% Above List Price
  • $683/SF
  • 42 Days On Market

  Current Estimated Value $595,163

  Last Listing Agent Mary Phelps William Pitt Sotheby's Int'l

  6 Old Mailcoach Rd, Redding, CT 06896
• 

  Est $905,367

  Not Listed For Sale

  23 Topledge Rd, Redding, CT 06896

  • 3 Beds
  • 2.5 Baths
  • 2,662 Sq Ft
  • Built 1995

  23 Topledge Rd, Redding, CT 06896

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Lynne Murphy Berkshire Hathaway NE Prop.
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  /37

  $1,099,000

  $200K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 4,316 Sq Ft

  16 Shady Ln, Redding, CT 06896

  Ideal setting and location! This spacious 12 room split level home tucked away on a country lane in the heart of Redding, offers the perfect blend of privacy, charm, and versatility. Set on 3.64 acres, this unique property features a spacious main residence with an open floor plan providing easy living, hardwood floors, an expansive primary suite, in-ground concrete pool, Ironwood deck, and

  Alexis Bennett Coldwell Banker Realty

  16 Shady Ln, Redding, CT 06896
• 

  $579,350

  Sold Jul 24, 2026

  9 Apple Ln, Redding, CT 06896

  • 3 Beds
  • 2 Baths
  • 1,952 Sq Ft
  • Built 1953

  Last Sold Summary

  • 5% Above List Price
  • $297/SF
  • 32 Days On Market

  Current Estimated Value $548,437

  Last Listing Agent Marilyn Sloper Coldwell Banker Realty

  9 Apple Ln, Redding, CT 06896
• 

  Est $806,432

  Not Listed For Sale

  52 Topledge Rd, Redding, CT 06896

  • 4 Beds
  • 2.5 Baths
  • 2,990 Sq Ft
  • Built 1977

  52 Topledge Rd, Redding, CT 06896

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Jay Contessa William Pitt Sotheby's Int'l
• 

  

  /34

  $699,000

  Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,111 Sq Ft

  29 Lonetown Rd, Redding, CT 06896

  Welcome to 29 Lonetown Road, a timeless 1915 Colonial, where historic character, thoughtful updates and an extraordinary setting come together. Set on 1.5 picturesque acres, this lovingly maintained home has been cherished by the same family for more than 36 years and is ready for its next chapter. Inside, original hardwood floors, built-ins and beautiful period details create warmth and

  Brianna Carvalho Compass Connecticut, LLC

  29 Lonetown Rd, Redding, CT 06896

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