Redding Homes for Sale

Welcome to Redding, Connecticut, a picturesque town nestled in the scenic Fairfield County. Known for its charming rural atmosphere and close-knit community, Redding offers the perfect blend of tranquility and convenience. With rolling hills, lush woodlands, and an abundance of outdoor recreational opportunities, this town is a haven for nature lovers and families alike.

Redding boasts a rich history, with beautiful historic homes that reflect its heritage. The town is home to several parks, including the expansive Redding Town Park and the serene Putnam Memorial State Park, offering residents plenty of space for hiking, picnicking, and enjoying the great outdoors. The vibrant arts scene, highlighted by the Redding Historical Society and various local galleries, adds to the town’s charm, making it a cultural hub in the region.

For those considering a move, Redding has a diverse array of homes for sale that cater to various tastes and budgets. From cozy cottages to sprawling estates, each property offers unique features and plenty of character. The real estate market in Redding is thriving, with opportunities for first-time homebuyers, families seeking more space, and those looking for a peaceful retreat from the hustle and bustle of city life.

With excellent schools, a strong sense of community, and a commitment to preserving its natural beauty, Redding is more than just a place to live; it’s a place to call home. Explore the homes for sale in this charming town and discover the perfect setting for your next chapter!

Newest Redding Homes for Sale

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 24211675 MLS

Rare West Redding Opportunity: Massive Upside, Privacy & Unmatched Potential. An exceptional property nestled in one of West Redding's most prestigious estate areas. Spanning over 5,000 sq ft of partially finished space across 3 levels, this distinctive custom-built Contemporary Colonial sits on 12.04 private, park-like acres in a secluded woodland setting. 3 bedrooms include a main level Primary suite, 3 full baths, and 3 half baths. The main living areas are bathed in natural light through walls of windows, with multiple decks taking in the spectacular, tree-lined views. The expansive walk-out lower level adds versatility and flexible living space-ready to make it your own. Adding incredible value and utility is a separate, working two-bay barn-ideal for a contractor, landscape equipment, large vehicle storage, or a workshop. While the residence requires a full interior and exterior renovation, the structure, grounds, and premier location make this a rare value-add investment and an outstanding treasure. Bring your inspiration, passion, and ingenuity to restore and preserve the deep-rooted spirit and enduring legacy of this remarkable residence. Enjoy a sought-after Redding location convenient to the train, top-rated schools, local shopping, and commuter routes-all just 65 miles to the Upper West Side of Manhattan. A real diamond-in-the-rough to be sold "as is"- Price reflects condition.

260 Umpawaug Rd, Redding

$539,000

2 Beds ⋅ 2 Baths ⋅ 24216380 MLS

Welcome to 85 Lonetown Road! This charming New England home offers a wonderful blend of character, comfortable living, and beautiful outdoor space. This 2 bedroom 2 bathroom home features a beautifully updated kitchen with granite countertops and stainless steel appliances, and a cozy brick fireplace. Additional living space on the upper level provides flexibility for a variety of needs. Outside, enjoy the open lawn, mature trees, and picturesque natural scenery that abuts a beautiful golf course. A spacious stone patio and covered porch make it ideal for entertaining or unwinding. The property also features an attached garage with washer and dryer included and a detached storage shed for added convenience. This home is a wonderful opportunity to enjoy classic Connecticut charm. (Property to be sold as is) *Also included is water softener system, outdoor security system, and Invisible Fence*

85 Lonetown Rd, Redding

$925,000

4 Beds ⋅ 3 Baths ⋅ 24215752 MLS

Idyllic and historic 4 bedroom Colonial, built in 1805 by Revolutionary War Loyalist John Pickett, formerly the Burr Sanford Dairy Farm, and lovingly cared for and updated over the past two centuries. Set on two park-like, level acres and surrounded by estates and farmland, this special property has mature trees and gardens and a sweeping grassy lawn leading to the detached barn/garage, making it ideal as a potential equestrian property. Inside you're greeted by formal dining and living rooms with hardwood flooring, plus multiple fireplaces and charming built-in nooks throughout. The cozy Family Room features a large stone fireplace and exposed beams and the generously sized kitchen leads to a versatile sitting room with bay window and wood stove. On this level there is also a convenient powder room, laundry room/pantry and a bright sunroom leading to the back gardens. The second floor features gorgeous wide plank flooring and original wood working, with four spacious bedrooms and two full baths, including a primary suite with walk-in closet and full bathroom. Finished third level attic with cathedral ceiling and original wood beams adds 899 sqft. The lower level offers plenty of room for storage and the detached barn garage has a loft above. Take in the picturesque views of the property from your side porch or private stone patio. Situated just minutes to the West Redding train station, Route 7 and 90 minutes to NYC making this an ideal spot for year-round or vacation living

126 Picketts Ridge Rd, Redding

$825,000

3 Beds ⋅ 3 Baths ⋅ 24215319 MLS

Completely renovated and move in ready on two private, wooded acres in beautiful Redding! Blending architectural character with modern comfort, this stunning home features soaring cathedral ceilings, exposed beams, expansive windows, and a fireplace. The beautifully updated kitchen showcases marble countertops, skylights, a Wolf gas range, and Sub-Zero refrigerator. Enjoy peace of mind with extensive renovations, including a brand new roof, septic system, high-efficiency heating & cooling systems, and beautifully updated interiors, with warranties on applicable improvements. Unwind on the private wraparound deck overlooking tranquil woods, perfect for birdwatching and morning coffee. Once lovingly tended by a gardening enthusiast, the grounds offer wonderful potential to bring the gardens back to life. Conveniently located near Georgetown's shops and restaurants, Route 7, Metro-North, and scenic trails. All the character, none of the renovation headaches. Simply move in and enjoy!

34 Dorethy Rd, Redding

$1,400,000

3 Beds ⋅ 4 Baths ⋅ 24215045 MLS

Welcome to "Stone Fences"-a historic 10-acre country estate tucked away in the quiet forests of Redding, Connecticut, just 90 minutes from Manhattan. Custom-built in 1938 by architect Richard Rowe for his wife, the home was awarded House Beautiful's top design honor in 1941. An MIT and Ecole des Beaux-Arts graduate who refined his craft alongside NYC architect Aymar Embury II, Rowe achieved an exceptional balance: an intimate, cozy atmosphere paired with an expansive living room built for grand entertaining. The architecture features a captivating fusion of English, Early American, French Provincial, and subtle Modern elements. Anchored by a Cotswold-style main cottage with two bedrooms and 3.5 bathrooms under an authentic slate roof, the residence opens onto grounds that unfold like a private sanctuary with manicured gardens, a gentle waterfall, a 14-foot-deep stone "bathing pool" pond, and a dramatic bridge spanning Gilbert Bennett Brook. A separate guest cottage, heated three-car garage, and custom chicken coop complete the estate, while comprehensive modern upgrades-including high-efficiency HVAC, updated windows, insulation, a full-house generator, a newer septic tank, roof, driveway, and bridge-ensure timeless beauty meets complete contemporary comfort.

76 Peaceable St, Redding

$749,000

3 Beds ⋅ 2 Baths ⋅ 24215005 MLS

Set along the Redding/Ridgefield line in scenic West Redding, 82 Simpaug Turnpike offers timeless character, thoughtful modern updates, and beautiful views of Umpawaug Pond. Cherished by one family for over 50 years, the home is rich in history, with an expansive living room anchored by a striking stone fireplace handcrafted from materials gathered on the property. A beautifully refreshed kitchen features a center island topped with soapstone, while three bedrooms, including a primary suite, two fully renovated baths, and a second wood-burning fireplace offer comfort and character throughout. Extensively updated since 2023, improvements include a new roof, HVAC, whole-house generator, electrical upgrades, and refinished hardwood floors. Outside, a fully fenced backyard creates a private retreat, complete with a low-maintenance Trex deck and a new paver patio. A two-car finished attached garage with new doors and epoxy flooring adds everyday convenience. Less than 10 minutes from Ridgefield's vibrant Main Street, with easy access to Route 7, shopping, dining, and nearby Topstone Park, this exceptional location offers the best of country living with everything close at hand.

82 Simpaug Tpke, Redding

$985,000

4 Beds ⋅ 4 Baths ⋅ 24207344 MLS

Discover a striking contemporary retreat nestled on nearly three private acres of lush, wooded Redding privacy. Featuring a picturesque brook, tranquil pond, and private waterfall, this property blends modern design with natural splendor. At the heart of the home, a magnificent double-sided fieldstone fireplace anchors the sun-filled living and dining rooms. Expansive windows and sliding glass doors frame serene views, opening to an oversized wraparound deck designed for effortless indoor-outdoor living, entertaining, or peaceful mornings. The meticulously renovated kitchen showcases custom-cut marble countertops imported specifically for the home, complemented by updated baths featuring custom tile. The spacious main-level primary suite serves as a true sanctuary with vaulted ceilings, a large distinctive open loft overlooking the bedroom, an updated ensuite bath, and a private balcony. Three additional bedrooms, updated bathrooms, and flexible living spaces offer exceptional comfort and versatility. The finished walkout lower level adds spacious recreation room, wet bar, half bath, and abundant storage. Ideally located close to New Pond Farm, Top Stone park, scenic hiking trails, nature preserves, local shops, and dining. Enjoy seamless commuting with convenient access to Metro-North train lines and NYC, plus close proximity to neighboring Ridgefield, Weston, and Wilton. A private country escape with convenience to everything.

131 Peaceable St, Redding

$975,000

4 Beds ⋅ 4 Baths ⋅ 24212649 MLS

True pride of ownership in this exceptional colonial home with extensive recent improvements, set back on 3 picturesque acres surrounded by nature & protected watershed forest with access to the Little River trail system & its 100 acre land preserve. This sophisticated home offers 3,350sf of living space with 4 BRs, 3 full/1 half updated baths, 3 fireplaces, crown moldings, built-ins, hdwd floors & open floor plan. The main level offers the generous LR with elegant brick fireplace & custom wood mantle/surround with French door access to the private office featuring a wall of custom bookshelves with lower cabinetry. The 1st floor also features the inviting kitchen with white cabinetry, contrasting black granite counters, & direct access to the stunning new screened porch, dining room, plus adjoining FR w/floor to ceiling brick fireplace & sliders to the Trex deck for outdoor enjoyment. Upstairs is equally impressive with elegant primary suite featuring a large custom WIC & luxe bath with mosaic stone floor, marble topped double vanities, plus oversized shower with elegant arched opening. There are 3 additional BRs, all with hdwd floors, one with vltd ceiling & 3rd fireplace, plus convenient laundry room. The lower level features a spacious rec/game room plus mudroom access to the attached 2 car garage. Recent improvements: new roof/gutters & chimney rebuilt; exterior repainted; Bluestone walkway; new windows; deck rebuilt & part converted to screened porch; new C/A; plus more!

85 Cross Hwy, Redding

$995,000

3 Beds ⋅ 3 Baths ⋅ 24211132 MLS

Sunlit architectural modern residence set back deeply on 4.03 private acres surrounded by woodlands, wildflowers, picturesque stream fed pond, & adjoining the 72 acre Gallows Hill Nature Preserve, featuring historic Revolutionary War camp sites & peaceful trails. This Zen sanctuary is a rare find - tucked fully into its natural surroundings yet expansive open floor plan that blurs the lines between indoor & out with soaring 2 story windows, skylights, extensive glass walls/sliders, plus wrap around Ipe deck for panoramic views. Significant improvements by the current owners including: new Hardie plank batten board siding; new windows, exterior doors & skylights; new HVAC; roof (2016); portable generator; new main floor office converted from laundry; & other designer enhancements. Total 2,740 sf of inviting living space including 3 BRs; 2 full/1 half baths; & lower level studio/fitness room, plus laundry & mudroom leading directly to the 2 car garage. Clean lines & modern flow from the sun drenched, two story entry foyer to the wide open great room including striking Brazilian cherry floors, vaulted living room with sliders to the deck, open dining room with double sliders to the deck, plus sleek, state of the art kitchen featuring Carrera marble counters, center island with bar overhand, S/S appliances & custom glass front stainless pantry system. Enjoy luxe main floor primary suite with spa like bath & custom closet, plus top West Redding location, just 56 miles to Midtown.

128 Gallows Hill Rd, Redding

$747,500

3 Beds ⋅ 2 Baths ⋅ 24208310 MLS

Set in a peaceful Redding setting, 87 Giles Hill Road is a charming Cape with a thoughtful and inviting floor plan and exceptional outdoor spaces designed for both relaxation and entertaining. The home has a warm and welcoming feel, with hardwood floors throughout the main living areas, generous natural light, and a comfortable flow from room to room. Two bedrooms located upstairs offer private retreats separate from the main living spaces. Outside, the property truly shines. A custom heated Gunite pool with spa and waterfall creates a private backyard retreat, while the custom outdoor fireplace provides another inviting gathering space for entertaining or relaxing outdoors. The lower deck grilling area is also conveniently equipped with a direct propane connection. With propane heat, classic Cape character, versatile living spaces, and exceptional outdoor amenities, 87 Giles Hill Road offers a wonderful opportunity to enjoy the privacy, natural beauty, and relaxed lifestyle that make Redding such a special place to call home.

87 Giles Hill Rd, Redding

$935,999

3 Beds ⋅ 3 Baths ⋅ 24211235 MLS

Set along scenic Redding Road across from the Mark Twain Stormfield estate, just minutes from the Wilton/Weston town line, this 3/4 bedroom home is the perfect blend of privacy and convenience in one of Redding's most desired settings. Set on a peaceful, picturesque, designated scenic road, the home features an open floor with vaulted ceilings, abundant natural light and a great flow for everyday living and entertaining. The first floor primary suite provides a sought-after single level living option. The second floor has two additional bedrooms and an office/bonus room with a full bathroom. Freshly painted, the home is move-in ready with modern conveniences throughout, including fiber-optic wiring, ethernet, and a whole-house generator. The expansive lower level offers exceptional versatility and ample room for a playroom, home gym, media/rec room. This is a rare opportunity to enjoy tranquility and natural beauty of Redding while remaining close to shopping, dining, schools and commuter routes. 1500+ sq ft of finished basement not included in the square footage

23 Lee Ln, Redding

$2,495,000

4 Beds ⋅ 7 Baths ⋅ 24185787 MLS

Architecturally Masterful design, inspired by famed architect HR Richardson's classic exteriors is married with a sophisticated, modern interior plan. This unique Redding estate home offers a scenic, private gated 9.54 acres and over 7200SF of modern living. The grand and gracious living room and dining rooms, formerly owned by a classical pianist, were utilized for elegant gatherings and concerts in the area & large enough for a concert grand. Warmed by a mantled fireplace with built-ins, the living area opens to a formal dining area to seat 12 special guests. The elegant foyer greets you with an expertly crafted, freestanding curved stair that leads to the upper floor. Adjacent to the dining room is a stark white kitchen with new quartz counters, an unusual contrast to the warm woods of the white oak floors and family room with stone,raised hearth fireplace. An adjacent Pecan wood study with walls of bookshelves and file drawers; an idea home office. A main level primary suite offers a series of custom closet built-ins & marble bath with shower, double sinks and even a bidet; a private owner retreat. Also, on this level is an excercise room w/whirlpool tub, sauna & full bath. Head up the back stair to the 2nd level w/2 bedroom suites, one serving as an ideal studio, with sink and an additional bedroom with large marble bath. A third bedroom & another full bath. The lower level offers a game room w/wood stove, office & den/ library wall. Inground gunite pool, 3 car garage

115 Limekiln Rd, Redding

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Redding Homes for Sale

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