Redding, CT Homes

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  $1,595,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,854 Sq Ft

  42 Topstone Rd, Redding, CT 06896

  Nestled on three private acres in highly sought-after Redding, Connecticut, with a private backyard gate entering directly into Topstone Park, this exceptional property offers a lifestyle defined by tranquility, privacy, and space. Surrounded by mature trees and drenched in natural light, the home embodies the timeless charm that has earned Redding its reputation as the 'Vermont of Connecticut".

  Giuseppe 'Joe' Melillo William Raveis Real Estate

  42 Topstone Rd, Redding, CT 06896
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  $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 $1,020,202

  Last Listing Agent David Landau RE/MAX Right Choice

  194 Lonetown Rd, Redding, CT 06896
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  Est $1,938,926 Not Listed For Sale

  72 George Hull Hill Rd, Redding, CT 06896

  • 5 Beds
  • 4.5 Baths
  • 5,513 Sq Ft
  • Built 2001

  72 George Hull Hill Rd, Redding, CT 06896

  Last Sold Summary

  • 5% Above List Price
  • $336/SF
  • 37 Days On Market

  • Last Sold Price $1,850,000
  • Jul 18, 2024

  Last Listing Agent Mary Phelps William Pitt
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  $825,000 Coming Soon

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

  81 Pinetree Rd, Redding, CT 06896

  A rare opportunity to own a thoughtfully updated antique home with a separate guest cottage, set on 1.66 picturesque acres in Redding, blending timeless character with modern livability in a way that is increasingly hard to find. A welcoming foyer with a vaulted ceiling sets the tone, leading into a sunlit living room anchored by a gas fireplace, custom built-ins, and a large picture window. The

  Brianna Carvalho Compass Connecticut, LLC

  81 Pinetree Rd, Redding, CT 06896
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  $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 $412,343

  Last Listing Agent Harry Stark William Raveis Real Estate

  280 Newtown Turnpike, Redding, CT 06896
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  Est $1,351,429 Not Listed For Sale

  44 Umpawaug Rd, Redding, CT 06896

  • 4 Beds
  • 5 Baths
  • 3,268 Sq Ft
  • Built 2001

  44 Umpawaug Rd, Redding, CT 06896

  Last Sold Summary

  • 10% Above List Price
  • $376/SF
  • 43 Days On Market

  • Last Sold Price $1,230,000
  • Dec 07, 2023

  Last Listing Agent Sharon Hoverman Coldwell Banker Realty
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  $849,900 Pending

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

  45 Great Pasture Rd, Redding, CT 06896

  Antique lovers, prepare to fall in love! The historic Deacon Samuel Read house, a Federal style colonial, built in 1745 by the founding family of Redding, CT. Enter the stunning 11 X 24 entry hall with exquisite millwork, a gracious sweeping staircase and original wide plank oak floors that run throughout the house. 9+ foot ceilings on the first floor enhance the elegant formal living room and

  Joe Scozzafava William Raveis Real Estate

  45 Great Pasture Rd, Redding, CT 06896
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  $601,000 Sold Jun 16, 2025

  30 Pine Mountain Rd, Redding, CT 06896

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

  Last Sold Summary

  • 20% Above List Price
  • $376/SF
  • 2 Days On Market

  Current Estimated Value $634,936

  Last Listing Agent Debbie Blum William Raveis Real Estate

  30 Pine Mountain Rd, Redding, CT 06896
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  Est $1,609,051 Not Listed For Sale

  4 Long Wall Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 3,596 Sq Ft
  • Built 2019

  4 Long Wall Rd, Redding, CT 06896

  Last Sold Summary

  • 15% Above List Price
  • $388/SF
  • 7 Days On Market

  • Last Sold Price $1,395,000
  • Feb 16, 2024

  Last Listing Agent Dee Braaten Keller Williams Realty
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  $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
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  $1,600,000 Sold Oct 02, 2025

  46 Dayton Rd, Redding, CT 06896

  • 6 Beds
  • 4.5 Baths
  • 3,573 Sq Ft
  • Built 1780

  Last Sold Summary

  • 5% Below List Price
  • $448/SF
  • 63 Days On Market

  Current Estimated Value $551,050

  Last Listing Agent Michele Tesei Houlihan Lawrence

  46 Dayton Rd, Redding, CT 06896
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  Est $1,423,996 Not Listed For Sale

  951 N Park Avenue Extension, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 4,352 Sq Ft
  • Built 2001

  951 N Park Avenue Extension, Redding, CT 06896

  Last Sold Summary

  • 10% Above List Price
  • $298/SF
  • 55 Days On Market

  • Last Sold Price $1,295,000
  • Jul 14, 2023

  Last Listing Agent Julie Vanderblue Higgins Group Real Estate
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  $925,000

  • 4 Beds
  • 4 Baths
  • 3,594 Sq Ft

  123 Peaceable St, Redding, CT 06896

  Welcome to 123a Peaceable St. West Redding, Connecticut | 4 Bedrooms | 3,594 Square Feet | 2.62 Private Acres. Tucked away at the end of a quiet cul-de-sac in highly desirable West Redding, this classic Colonial offers the rare combination of privacy, scale, opportunity. Set on 2.62 lightly wooded acres with stone walls.Built in 1988 and offering 3,594sqft above grade, the home unfolds w/

  Julie Setterlund William Pitt Sotheby's Int'l

  123 Peaceable St, Redding, CT 06896
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  $835,000 Sold Mar 02, 2026

  41 Sullivan Dr, Redding, CT 06896

  • 5 Beds
  • 4.5 Baths
  • 4,801 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Below List Price
  • $174/SF
  • 77 Days On Market

  Current Estimated Value $923,505

  Last Listing Agent Carol Hanlon Coldwell Banker Realty

  41 Sullivan Dr, Redding, CT 06896
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  Est $1,288,642 Not Listed For Sale

  5 Windy Hill Rd, Redding, CT 06896

  • 5 Beds
  • 4 Baths
  • 4,631 Sq Ft
  • Built 1997

  5 Windy Hill Rd, Redding, CT 06896

  Last Sold Summary

  • 32% Above List Price
  • $211/SF
  • 27 Days On Market

  • Last Sold Price $975,000
  • Aug 07, 2023

  Last Listing Agent Caroline Besancon William Pitt
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  $949,000

  • 4 Beds
  • 3.5 Baths
  • 4,234 Sq Ft

  299 Redding Rd, Redding, CT 06896

  Experience modern luxury in this beautifully renovated Colonial. A grand double-door entry opens to a bright foyer. The all-new gourmet chef's kitchen boasts a massive waterfall quartz island, high-end appliances, and pot filler. The open-concept main level flows into a spacious living room with brick fireplace, while a secondary family room features a dramatic floor-to-ceiling stone fireplace

  Natalia Rathbauer William Pitt Sotheby's Int'l

  299 Redding Rd, Redding, CT 06896
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  $1,700,000 Sold Sep 03, 2025

  37 Giles Hill Rd, Redding, CT 06896

  • 5 Beds
  • 3.5 Baths
  • 6,101 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $279/SF
  • 35 Days On Market

  Current Estimated Value $1,755,273

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

  37 Giles Hill Rd, Redding, CT 06896
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  Est $1,257,564 Not Listed For Sale

  7 Windy Hill Rd, Redding, CT 06896

  • 5 Beds
  • 6 Baths
  • 5,363 Sq Ft
  • Built 1999

  7 Windy Hill Rd, Redding, CT 06896

  Last Sold Summary

  • 22% Above List Price
  • $191/SF
  • 24 Days On Market

  • Last Sold Price $1,027,000
  • Aug 14, 2023

  Last Listing Agent Kristi Vaughan William Pitt
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  $1,849,000

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

  2 Longwood Dr, Redding, CT 06896

  ***Exceptional Value in Redding CT*** A refined Connecticut country residence for full-time living or weekend enjoyment. Set on nearly three meticulously landscaped acres on a private cul-de-sac drive with only 4 residences, you will enjoy living in one of Redding's most desirable residential enclaves. 2 Longwood Drive offers a safe, secure, and sophisticated country lifestyle that resonates

  Jeffrey Kaplan William Raveis Real Estate

  2 Longwood Dr, Redding, CT 06896
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  $675,000 Sold Jul 21, 2025

  21 White Birch Rd, Redding, CT 06896

  • 3 Beds
  • 2 Baths
  • 1,364 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Below List Price
  • $495/SF
  • 111 Days On Market

  Current Estimated Value $678,694

  Last Listing Agent Karen Gilmore Redfin Corporation

  21 White Birch Rd, Redding, CT 06896
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  Est $1,859,625 Not Listed For Sale

  78 George Hull Hill Rd, Redding, CT 06896

  • 4 Beds
  • 6 Baths
  • 6,218 Sq Ft
  • Built 2002

  78 George Hull Hill Rd, Redding, CT 06896

  Last Sold Summary

  • 11% Above List Price
  • $269/SF
  • 94 Days On Market

  • Last Sold Price $1,675,000
  • Jul 31, 2023

  Last Listing Agent Marilyn Caravetta Coldwell Banker Realty
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  $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
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  $865,000 Sold Aug 15, 2025

  9 Brick School Dr, Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 3,284 Sq Ft
  • Built 1969

  Last Sold Summary

  • 2% Below List Price
  • $263/SF
  • 87 Days On Market

  Current Estimated Value $892,019

  Last Listing Agent Alec Nyman Corcoran Centric Realty

  9 Brick School Dr, Redding, CT 06896
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  Est $1,612,593 Not Listed For Sale

  3 Quarry Rock Rd, Redding, CT 06896

  • 5 Beds
  • 3.5 Baths
  • 4,417 Sq Ft
  • Built 2000

  3 Quarry Rock Rd, Redding, CT 06896

  Last Sold Summary

  • 1% Above List Price
  • $362/SF
  • 25 Days On Market

  • Last Sold Price $1,600,000
  • Feb 27, 2025

  Last Listing Agent Tim Dent Coldwell Banker Realty
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  $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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  $800,000 Sold Jul 29, 2025

  24 Newtown Turnpike, Redding, CT 06896

  • 2 Beds
  • 2.5 Baths
  • 2,920 Sq Ft
  • Built 1956

  Last Sold Summary

  • 1% Above List Price
  • $274/SF
  • 65 Days On Market

  Current Estimated Value $851,598

  Last Listing Agent Leslie Clarke Compass Connecticut, LLC

  24 Newtown Turnpike, Redding, CT 06896
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  Est $1,199,359 Not Listed For Sale

  30 Wood Rd, Redding, CT 06896

  • 4 Beds
  • 2.5 Baths
  • 4,672 Sq Ft
  • Built 2001

  30 Wood Rd, Redding, CT 06896

  Last Sold Summary

  • 3% Above List Price
  • $248/SF
  • 14 Days On Market

  • Last Sold Price $1,160,000
  • Jun 26, 2024

  Last Listing Agent Jay Contessa William Pitt
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  $669,000 Under Contract

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

  101 Sport Hill Rd, Redding, CT 06896

  Set behind a classic New England stone wall in highly desirable West Redding, this move-in ready home offers space, flexibility, and charm across 2,294 sq ft on the main level plus 952 sq ft in the finished lower level. Thoughtfully laid out and currently utilized as a 3-bedroom, the home includes a versatile additional room ideal for a bedroom, office, or guest space. Bright, open layout with

  Nicholas Wilson Coldwell Banker Realty

  101 Sport Hill Rd, Redding, CT 06896
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  $1,525,000 Sold Dec 23, 2025

  61 Marchant Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 4,146 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Below List Price
  • $368/SF
  • 75 Days On Market

  Current Estimated Value $1,548,466

  Last Listing Agent Robert Neumann Houlihan Lawrence

  61 Marchant Rd, Redding, CT 06896
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  Est $1,369,512 Not Listed For Sale

  358 Newtown Turnpike, Redding, CT 06896

  • 4 Beds
  • 5 Baths
  • 4,365 Sq Ft
  • Built 2006

  358 Newtown Turnpike, Redding, CT 06896

  Last Sold Summary

  • 3% Above List Price
  • $304/SF
  • 278 Days On Market

  • Last Sold Price $1,325,000
  • Jan 16, 2024

  Last Listing Agent Sandra Juliano Berkshire Hathaway Home Services
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  $695,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  5 Iris Ln, Redding, CT 06896

  Set on a quiet cul-de-sac within a true neighborhood setting, this 3 bedroom, 2 bath ranch offers easy, one-level living on a beautifully flat .78-acre property, a rare find in Redding. Charming details throughout, including built-ins, multiple window seats, picture windows, and a wood-burning fireplace, create a warm and inviting atmosphere filled with natural light. The kitchen features a

  Brianna Carvalho Compass Connecticut, LLC

  5 Iris Ln, Redding, CT 06896
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  $939,000 Sold Feb 17, 2026

  283 Redding Rd, Redding, CT 06896

  • 4 Beds
  • 3.5 Baths
  • 4,641 Sq Ft
  • Built 1936

  Last Sold Summary

  • 1% Below List Price
  • $202/SF
  • 183 Days On Market

  Current Estimated Value $928,316

  Last Listing Agent Lynne Murphy Berkshire Hathaway NE Prop.

  283 Redding Rd, Redding, CT 06896
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  Est $784,793 Not Listed For Sale

  65 Wayside Ln, Redding, CT 06896

  • 2 Beds
  • 3 Baths
  • 2,285 Sq Ft
  • Built 1918

  65 Wayside Ln, Redding, CT 06896

  Last Sold Summary

  • 9% Above List Price
  • $315/SF
  • 144 Days On Market

  • Last Sold Price $719,000
  • Mar 25, 2025

  Last Listing Agent John Frey Coldwell Banker Realty
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  $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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  $1,475,000 Sold Oct 15, 2025

  23 Sanfordtown Rd, Redding, CT 06896

  • 4 Beds
  • 4.5 Baths
  • 3,446 Sq Ft
  • Built 1987

  Last Sold Summary

  • $428/SF
  • 81 Days On Market

  Current Estimated Value $1,429,320

  Last Listing Agent Roni Agress William Pitt Sotheby's Int'l

  23 Sanfordtown Rd, Redding, CT 06896
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  Est $1,299,699 Not Listed For Sale

  32 Blueberry Hill Rd, Redding, CT 06896

  • 5 Beds
  • 4.5 Baths
  • 5,237 Sq Ft
  • Built 2004

  32 Blueberry Hill Rd, Redding, CT 06896

  Last Sold Summary

  • 11% Above List Price
  • $224/SF
  • 71 Days On Market

  • Last Sold Price $1,175,000
  • Sep 04, 2024

  Last Listing Agent Mike Albert RE/MAX
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  $799,000

  • 3 Beds
  • 2 Baths
  • 1,684 Sq Ft

  39 Seventy Acre Rd, Redding, CT 06896

  Idyllic & sprawling country ranch on 1.38 private acres with fenced in backyard in top West Redding location. Charming yet sophisticated with extensive designer updates throughout. Total 1,753 sf of light, bright & open living space, plus additional 963 sf of nearly finished space in the expansive walk-out lower level with wood grained tiled floor & flexible space for fitness, game room, or home

  Laura Ancona William Pitt Sotheby's Int'l

  39 Seventy Acre Rd, Redding, CT 06896
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  $725,000 Sold Jul 24, 2025

  116 Seventy Acre Rd, Redding, CT 06896

  • 5 Beds
  • 3.5 Baths
  • 3,786 Sq Ft
  • Built 1980

  Last Sold Summary

  • $191/SF
  • 88 Days On Market

  Current Estimated Value $893,394

  Last Listing Agent Shalini Madaras Silver Pine Real Estate

  116 Seventy Acre Rd, Redding, CT 06896
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  Est $1,452,546 Not Listed For Sale

  710 Redding Rd, Redding, CT 06896

  • 4 Beds
  • 5 Baths
  • 4,320 Sq Ft
  • Built 2002

  710 Redding Rd, Redding, CT 06896

  Last Sold Summary

  • 5% Above List Price
  • $321/SF
  • 131 Days On Market

  • Last Sold Price $1,387,500
  • Mar 24, 2025

  Last Listing Agent Matt Rose Keller Williams Realty
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  $750,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,092 Sq Ft

  148 Old Redding Rd, Redding, CT 06896

  HIGHEST and BEST By TUESDAY MAY 5TH. Tucked away, off the beaten path and down a quiet country lane, this charming 4-bedroom, 2.5-bath Cape Cod home offers a peaceful retreat surrounded by nature. With more than 2,300 square feet of living space, this well-loved home combines warmth, character, and endless potential. The main level features two bedrooms, a full bath, and a flexible layout that

  Susan Warner-Lambert Carbutti & Co., Realtors

  148 Old Redding Rd, Redding, CT 06896

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