3,456

Redding, CT Homes

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  • 219 Redding Rd, Redding, CT 06896
    219 Redding Rd, Redding, CT 06896
    219 Redding Rd, Redding, CT 06896
    /27

    $569,000

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

    219 Redding Rd, Redding, CT 06896

    Clean, turnkey and ready for immediate occupancy, 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

    Cher Iravani Redevelopment Realty Group

    219 Redding Rd, Redding, CT 06896
  • 9 Brick School Dr, Redding, CT 06896

    $865,000 Sold Aug 15, 2025

    • 3,284 Sq Ft
    • $263/SF
    • 87 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1969

    9 Brick School Dr, Redding, CT 06896

    Beautifully maintained 4-bedroom, 3-bathroom colonial nestled on a picturesque cul-de-sac in one of Redding's most desirable neighborhoods. A nature lover's dream set on nearly 3 private acres of professionally landscaped grounds. Hardwood floors throughout, large kitchen with granite countertops, and a peaceful sunroom overlooking the private backyard. Upstairs, the primary suite is a luxurious

    Alec Nyman Corcoran Centric Realty

    9 Brick School Dr, Redding, CT 06896
  • 176 Picketts Ridge Rd, Redding, CT 06896
    176 Picketts Ridge Rd, Redding, CT 06896
    176 Picketts Ridge Rd, Redding, CT 06896
    /5

    $279,000

    • Land
    • 2.16 Acres
    • $129,167 per Acre

    176 Picketts Ridge Rd, Redding, CT 06896

    Build Your Dream Home with Breathtaking Lake Views. Imagine waking up each morning to the serene beauty of water and tranquil nature. This is your opportunity to turn that vision into reality on this exquisite lake view property. Offering a rare chance to design and construct your custom sanctuary, this land is the perfect foundation for the home you've always dreamed of. Nestled in a peaceful

    Kristi Vaughan William Pitt Sotheby's Int'l

    176 Picketts Ridge Rd, Redding, CT 06896
  • 12 Winding Brook Ln, Redding, CT 06896

    $884,000 Sold Aug 08, 2025

    • 3,019 Sq Ft
    • $293/SF
    • 71 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 1971

    12 Winding Brook Ln, Redding, CT 06896

    TIMELESS CLASSIC Colonial in the heart of picturesque Redding that offers TOP RATED schools. This spacious, move-in ready residence features FOUR generously sized bedrooms & THREE full bathrooms, all adorned with beautiful HDWD floors. The home's layout boasts a fantastic flow. An updated Eat-In Kitchen, Large Family Room, & sophisticated Dining Room await you, along with a Living Room featuring

    Annmarie Del Franco Blackstone Properties of CT

    12 Winding Brook Ln, Redding, CT 06896
  • 18 Great Meadow Rd, Redding, CT 06896
    18 Great Meadow Rd, Redding, CT 06896
    18 Great Meadow Rd, Redding, CT 06896
    /32

    $679,000

    • 3 Beds
    • 2 Baths
    • 2,009 Sq Ft

    18 Great Meadow Rd, Redding, CT 06896

    Welcome to 18 Great Meadow Road, a newly renovated home with a completely flat 2.5 acre lot on a quiet, cul-de-sac street. This house is the perfect combination of country side living but in a state of the art, almost new construction house. Although quiet and scenic, you are only 2 miles from the highly rated Joel Barlow high school and essentially in "central" Fairfield County close to all

    Jason Saphire www.HomeZu.com

    18 Great Meadow Rd, Redding, CT 06896
  • 22 Woods Way Unit 22, Redding, CT 06896

    $790,000 Sold Aug 06, 2025

    • 2,022 Sq Ft
    • $391/SF
    • 55 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2000

    22 Woods Way Unit 22, Redding, CT 06896

    Welcome to 22 Woods Way, a distinguished freestanding home in the highly sought-after Redding Woods community-an enclave of elegant residences built in. This home offers superb outdoor living, with a private side porch featuring rich mahogany Ipe decking and a rear patio that opens directly from the spacious eat-in kitchen-ideal for seamless indoor-outdoor entertaining. The foyer's limestone

    Sandra Juliano Berkshire Hathaway NE Prop.

    22 Woods Way Unit 22, Redding, CT 06896
  • 118 Sanfordtown Rd, Redding, CT 06896
    118 Sanfordtown Rd, Redding, CT 06896
    118 Sanfordtown Rd, Redding, CT 06896
    /23

    $999,000

    • 4 Beds
    • 1.5 Baths
    • 3,111 Sq Ft

    118 Sanfordtown Rd, Redding, CT 06896

    Sparkling jewel box in the center of Redding, the Wakeman Smith House is a masterful blend of historic charm and modern refinement. Originally built in 1780 and expanded in 1840 into a graceful Georgian Revival, this architectural gem sits on 1.4 tranquil, park-like acres surrounded by stone walls, mature trees, and professionally designed perennial gardens; all within one of Redding's most

    Holly Hill Higgins Group Greenwich

    118 Sanfordtown Rd, Redding, CT 06896
  • 98 Hopewell Woods Rd, Redding, CT 06896

    $1,250,000 Sold Aug 01, 2025

    • 3,773 Sq Ft
    • $331/SF
    • 22 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2004

    98 Hopewell Woods Rd, Redding, CT 06896

    Pride of ownership abounds in this immaculate home, custom built in 2004 by the original owners with extensive recent updates. Exceptional private setting on 2.18 tranquil acres w/stone walls, mature professional landscaping including specimen trees, perennial gardens, stone patio, plus 5 minute walk to scenic Huntington State Park w/over 1,000 acres of hiking/biking trails & 5 ponds. Impressive

    Laura Ancona William Pitt Sotheby's Int'l

    98 Hopewell Woods Rd, Redding, CT 06896
  • 229 Umpawaug Rd, Redding, CT 06896
    229 Umpawaug Rd, Redding, CT 06896
    229 Umpawaug Rd, Redding, CT 06896
    /34

    $7,495,000

    • 6 Beds
    • 11 Baths
    • 7,528 Sq Ft

    229 Umpawaug Rd, Redding, CT 06896

    Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor plan, formal and informal rooms, embracing the incredibly private 6.5 acres of hand-stacked walls, privacy gates and

    Stacy Young William Raveis Real Estate

    229 Umpawaug Rd, Redding, CT 06896
  • 36 Pheasant Ridge Rd, Redding, CT 06896

    $914,000 Sold Jul 31, 2025

    • 2,954 Sq Ft
    • $309/SF
    • 48 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1971

    36 Pheasant Ridge Rd, Redding, CT 06896

    Welcome home to this beautiful colonial set on just over two private, level acres in a desirable SE Redding cul-de-sac neighborhood close to Huntington State Park. Enjoy indoor and outdoor living in this spacious, sun-drenched home. On the first floor you will find an oversized family room with fireplace, living room and dining room with hardwood flooring throughout. The light-filled kitchen

    Margi Esten Coldwell Banker Realty

    36 Pheasant Ridge Rd, Redding, CT 06896
  • 0 Black Rock Turnpike, West Redding, CT 06896
    0 Black Rock Turnpike, West Redding, CT 06896
    0 Black Rock Turnpike, West Redding, CT 06896
    /20

    $1,100,000

    • Land
    • 16.47 Acres
    • $66,788 per Acre

    0 Black Rock Turnpike, West Redding, CT 06896

    Unlock Premier Development Potential in Redding Ridge, Redding, CT! Imagine crafting a stunning 4-5 home luxury subdivision on this expansive 15+ acre parcel of vacant land in prestigious Redding, Connecticut. The property may be subdividable (subject to approvals), offering flexibility and opportunity for a discerning developer to bring custom designs to life. This exceptional land is not

    Christine Ricci Keller Williams NY Realty

    0 Black Rock Turnpike, West Redding, CT 06896
  • 6 Middlebrook Pond Rd, Redding, CT 06896

    $900,000 Sold Jul 30, 2025

    • 2,484 Sq Ft
    • $362/SF
    • 53 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1985

    6 Middlebrook Pond Rd, Redding, CT 06896

    Welcome to 6 Middlebrook Pond Rd, Redding! Beautiful & Charming 8 room, 4 bedroom, 2.5 bath Cape situated on a nice private lot in established tree lined subdivision with underground utilities & Cul-de-sac with close proximity to Huntington & Putnam Memorial State Parks. Main level features include hardwood flooring, crown molding, formal living room with fireplace, built-in bookshelves, large

    Gary Gilroy Alpine Realty

    6 Middlebrook Pond Rd, Redding, CT 06896
  • 145 Limekiln Rd, Redding, CT 06896
    145 Limekiln Rd, Redding, CT 06896
    /2

    $599,000

    • Land
    • 9.31 Acres
    • $64,339 per Acre

    145 Limekiln Rd, Redding, CT 06896

    Single homesite located in beautiful Redding. This 9.3 acre parcel of meadowland features panoramic views and borders land preserve woodlands. Perfect horse property. Deep & Perc test done in past. Close to Country Club, school.

    Ellie Fiorita William Raveis Real Estate

    145 Limekiln Rd, Redding, CT 06896
  • 24 Newtown Turnpike, Redding, CT 06896

    $800,000 Sold Jul 29, 2025

    • 2,920 Sq Ft
    • $274/SF
    • 65 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1956

    24 Newtown Turnpike, Redding, CT 06896

    A RARE RETREAT - perched overlooking the Saugatuck Reservoir is one of the very few residential properties on the waterfront side of Newtown Turnpike. With 6.7 acres of private property, the freshly renovated 2,920 sqft home enjoys unmatched views of the reservoir and surrounding sanctuary of forest filled with hiking trails, fishing spots and stunning natural beauty. The main floor has an open

    Leslie Clarke Compass Connecticut, LLC

    24 Newtown Turnpike, Redding, CT 06896
  • 45 Great Pasture Rd, Redding, CT 06896
    45 Great Pasture Rd, Redding, CT 06896
    45 Great Pasture Rd, Redding, CT 06896
    /39

    $849,900

    • 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
  • 12 Rob Rider Rd, Redding, CT 06896

    $1,399,000 Sold Jul 25, 2025

    • 4,143 Sq Ft
    • $338/SF
    • 16 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1995

    12 Rob Rider Rd, Redding, CT 06896

    Welcome to 12 Rob Rider, nestled in a serene and private neighborhood. Thoughtfully renovated with exceptional design and detail, this 5-bedroom, 4.5-bath home offers comfort and elegance throughout. A grand foyer with architectural openness welcomes natural light. New herringbone wood flooring adds sophistication, complemented by refinished oak floors. The luxurious kitchen features custom

    Peggy Jorgensen Compass Connecticut, LLC

    12 Rob Rider Rd, Redding, CT 06896
  • 241 Black Rock Turnpike, Redding, CT 06896
    241 Black Rock Turnpike, Redding, CT 06896
    241 Black Rock Turnpike, Redding, CT 06896
    /40

    $4,495,000

    • 6 Beds
    • 11 Baths
    • 17,548 Sq Ft

    241 Black Rock Turnpike, Redding, CT 06896

    Love life? Love it even more when you arrive home to this exquisite Normandy Chateau with all the special attributes you would expect from a luxurious estate. Set on over 19 acres of lush property, the setting is nothing but idyllic with beautiful gardens, wide open pastures, koi ponds and scenic water views. The best surprise is how inviting & comfortable the home truly is. Of course, there are

    Jodi Gutierrez Alliance R.E. Consultants

    241 Black Rock Turnpike, Redding, CT 06896
  • 23 Old Mailcoach Rd, Redding, CT 06896

    $1,051,500 Sold Jul 25, 2025

    • 4,315 Sq Ft
    • $244/SF
    • 79 Days On Market
    • 5 Beds
    • 4.5 Baths
    • Built 1941

    23 Old Mailcoach Rd, Redding, CT 06896

    Prepare to be captivated by this Normandy-style architectural gem-an extraordinary home that defies convention & redefines country living. Nestled on 4 beautifully landscaped acres in scenic Redding, this 4,200+ SF post-and-beam estate is a rare blend of design, nature & tranquility. From the moment you arrive, the two-story fieldstone archway & tiered design-w/ entrances on all ground levels-set

    Matthew Nuzie RE/MAX Right Choice

    23 Old Mailcoach Rd, Redding, CT 06896
  • 67 Umpawaug Rd, Redding, CT 06896
    67 Umpawaug Rd, Redding, CT 06896
    67 Umpawaug Rd, 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
  • 4 Longwood Dr, Redding, CT 06896

    $2,600,000 Sold Jul 25, 2025

    • 10,197 Sq Ft
    • $255/SF
    • 45 Days On Market
    • 7 Beds
    • 7 Baths
    • Built 2000

    4 Longwood Dr, Redding, CT 06896

    Welcome to 4 Longwood Drive, a quintessential New England retreat set on 3.75 serene acres of amenity filled living spaces. This exquisite property provides an idyllic lifestyle amidst natural beauty, making it a perfect haven for families and individuals seeking comfort, elegance, and tranquility. The stone and shingle exterior of this elegant, custom-designed colonial residence was influenced

    Jeffrey Kaplan William Raveis Real Estate

    4 Longwood Dr, Redding, CT 06896
  • 65 Umpawaug Rd, Redding, CT 06896
    65 Umpawaug 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
  • 3 Dan Beard Ln, Redding, CT 06896

    $1,600,000 Sold Jul 24, 2025

    • 5,945 Sq Ft
    • $269/SF
    • 2 Days On Market
    • 5 Beds
    • 6 Baths
    • Built 1986

    3 Dan Beard Ln, Redding, CT 06896

    Stunning New England Saltbox w/ Guest Cottage (legal ADU) in Picturesque Redding CT: Exquisite New England Saltbox, complete w/ detached guest cottage, is nestled in the heart of Redding, a charming town in Fairfield County known for its historical significance & natural beauty. Surrounded by rolling hills, forests, & meadows, this property boasts a tranquil escape while being just a short drive

    Keith Evans William Raveis Real Estate

    3 Dan Beard Ln, Redding, CT 06896
  • 94 Old Stagecoach Rd, Redding, CT 06896
    94 Old Stagecoach Rd, Redding, CT 06896
    94 Old Stagecoach Rd, Redding, CT 06896
    /28

    $879,000 Pending

    • 4 Beds
    • 2.5 Baths
    • 2,177 Sq Ft

    94 Old Stagecoach Rd, Redding, CT 06896

    Welcome to this absolutely turnkey and beautifully updated 4 bedroom, 2.5 bath center-hall Colonial offering stunning curb appeal, an open floor plan, and a prime location in the heart of Redding. Set on a quiet, walkable street close to schools and town center, it offers the perfect blend of comfort and convenience. Inside, light-filled spaces have been thoughtfully opened up for modern living.

    Brianna Carvalho Compass Connecticut, LLC

    94 Old Stagecoach Rd, Redding, CT 06896
  • 116 Seventy Acre Rd, Redding, CT 06896

    $725,000 Sold Jul 24, 2025

    • 3,786 Sq Ft
    • $191/SF
    • 88 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1980

    116 Seventy Acre Rd, Redding, CT 06896

    Charming Cape Cod-Style Home with Exceptional Potential Set back off the road with eye-catching curb appeal, this spacious Cape offers the perfect blend of warmth, character, & room to grow on beautiful level grounds. Featuring 5 generously sized bedrooms & 3.5 baths, including a primary suite w/attached bath & walk-in closet, it's ideal for both comfort & entertaining. Through the large & many

    Shalini Madaras Silver Pine Real Estate

    116 Seventy Acre Rd, Redding, CT 06896
  • 66 Portland Ave, Redding, CT 06896
    66 Portland Ave, Redding, CT 06896
    66 Portland Ave, Redding, CT 06896
    /24

    $549,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,964 Sq Ft

    66 Portland Ave, Redding, CT 06896

    IDEAL FOR AN INVESTOR, HOME IS ZONED AS A 2-FAMILY. However, this home has been used for so many years with the upstairs unit used by family members. The upstairs unit consists of 918 sq ft of 4 rooms, 2 bedrooms plus a tub bath and has as a remodeled kitchen, newer windows and newer floors. The main level has 1046 sq ft and enjoys an open front porch with a view of the Gilbert & Bennett Pond

    Marilyn Sloper Coldwell Banker Realty

    66 Portland Ave, Redding, CT 06896
  • 2 Meadows Edge, Redding, CT 06896

    $2,009,000 Sold Jul 22, 2025

    • 5,768 Sq Ft
    • $348/SF
    • 90 Days On Market
    • 4 Beds
    • 5 Baths
    • Built 1998

    2 Meadows Edge, Redding, CT 06896

    Welcome to 2 Meadows Edge-the pinnacle of luxury living in Redding's most exclusive neighborhood. Set on 3.4 of the most coveted, manicured land in the area, this magazine-worthy modern farmhouse is a like-new construction masterpiece-without the wait. Every inch has been reimagined with expert craftsmanship and design precision. The exterior pairs timeless materials with clean, modern lines:

    Matthew Nuzie RE/MAX Right Choice

    2 Meadows Edge, Redding, CT 06896
  • 23 Goodsell Hill Rd, Redding, CT 06896
    23 Goodsell Hill Rd, Redding, CT 06896
    23 Goodsell Hill Rd, Redding, CT 06896
    /40

    $1,350,000 Pending

    • 4 Beds
    • 3 Baths
    • 4,386 Sq Ft

    23 Goodsell Hill Rd, Redding, CT 06896

    This charming 1870 antique home is pure perfection conveniently located in West Redding. The secluded 3+ acre property with rolling landscape and exquisite perennial gardens with old stone walls is a true gem with beautiful period home features, wide-planked floors and 5 working fireplaces. The master suite with fireplace and full bath is conveniently located on the main floor with private access

    Bonnie Troy Howard Hanna Rand Realty

    23 Goodsell Hill Rd, Redding, CT 06896

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