Redding CT Homes for Sale and Town Profile

Explore and download Redding demographics and school report cards, discover local neighborhoods and condo/townhouse communities, and learn about commuting routes and popular landmarks.

Snapshot

Where: Northern Fairfield County, Western CT
Population: ~8,800 residents
Size: ~31.5 sq mi
ZIP / Area code: 06896 / 203

Where It Is

By car: Accessible via Route 107 and Route 58, with connections to I-84 to the north and the Merritt Parkway to the south. About 60–75 minutes to NYC depending on traffic. By rail: No train station in Redding itself; residents typically use the Branchville Station in adjacent Ridgefield (Danbury Branch) or Bethel Station. Nearby: Borders Ridgefield, Weston, Bethel, Newtown, and Easton.

Overview

Connecticut Magazine has ranked Redding its #1 Small Town — not once, but repeatedly over the past decade. It's easy to see why. With fewer than 9,000 residents spread across more than 31 square miles, Redding offers a level of peace, privacy, and natural beauty that's increasingly rare in Fairfield County. This is a town where the landscape is deliberately protected, the community is intentional, and the pace of life is — by design — unhurried.

Community & Lifestyle

Redding doesn't have a conventional commercial downtown, and that's the point. Georgetown, the community's most active village, offers a small Main Street with local businesses, dining, and services. The town hosts a farmers' market, seasonal community events, and a strong volunteer culture. Residents tend to be highly educated, independent, and deeply connected to the natural environment. The Redding Community Center hosts events and programs that bring residents together throughout the year.

Education

Redding is served by Regional School District 09, which Redding shares with the neighboring town of Easton. The district includes Redding Elementary School (PreK–4), John Read Middle School (grades 5–8) — a designated National Blue Ribbon School — and Joel Barlow High School (shared with Easton, grades 9–12). John Read earned the National Blue Ribbon distinction in 2012, placing it among the top 269 schools in the country that year. The district's small size means students develop strong bonds with teachers and classmates throughout their entire school career — a meaningful differentiator from larger district towns.

Parks & Recreation

Redding dedicates more than 25% of its land to open space — a remarkable commitment to environmental preservation. Putnam Memorial State Park, known as the 'Valley Forge of Connecticut,' commemorates the Revolutionary War encampment of 1778–79. Collis P. Huntington State Park and Paugussett State Forest offer hundreds of acres of trails, wildlife observation, and fishing. The entire town feels like a nature preserve — because in many ways, it is.

Real Estate & Housing

Redding's housing market is defined by privacy, land, and architectural diversity. Expect historic colonial farmhouses, mid-century homes, and contemporary estates — all on large lots, most surrounded by woods or fields. The median home value sits above $900,000, reflecting both the town's affluent buyer profile and the scarcity of available inventory. This is not a market for buyers seeking density, condos, or walkable amenities; it's a market for buyers who deeply value privacy, land, and natural beauty.

Government

Redding operates under a First Selectman / Board of Selectmen form of government with direct citizen participation through town meeting. The town is known for its engaged and thoughtful civic culture.

Notable Facts

Connecticut's #1 Small Town: Connecticut Magazine has ranked Redding #1 or #2 for the past decade.
National Blue Ribbon School: John Read Middle School received the National Blue Ribbon designation in 2012.
Revolutionary History: Putnam Memorial State Park preserves the 1778–79 winter encampment site.
Open Space Leader: Over 25% of Redding's land is permanently protected open space.

Vibe

Profoundly rural, intellectually rich, and completely intentional. Redding attracts a particular kind of buyer — one who genuinely wants space, quiet, and nature, and who has no interest in being close to a Starbucks. There's a strong artistic community here (the town has more artists and designers per capita than 90% of American communities), a deeply educated population, and a shared commitment to keeping the town exactly as it is.

Who It's For

Perfect for: Buyers who prioritize privacy, land, and natural beauty above all; remote workers; those drawn to a highly educated, arts-oriented community with exceptional schools. Consider elsewhere if you need walkability, train access, or a lower price point.

Thinking About Redding?

Redding's inventory is limited and listings rarely last. I'd love to help you navigate this quiet but competitive market — get in touch to be among the first to hear about new opportunities.

Newest Listings in Redding CT

$1,450,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$599,999

ACTIVE Status ⋅ 24215777 MLS

Unlock Premier Development Potential in Redding Ridge, Redding, CT! Imagine crafting a stunning Luxury subdivision on this expansive 15+ acre parcel of vacant land in prestigious Redding, Connecticut. The property may be sub-dividable (subject to approvals), offering flexibility and opportunity for a discerning developer to bring custom designs to life. This exceptional land is not located in a flood zone, adding peace of mind to your plans. Enjoy unparalleled convenience with nearby shopping, renowned golf courses, and abundant recreational activities. Commuting is easy with the Danbury Fair Mall and I-84 just a 20-minute drive away. Located within the highly rated Redding school district, this is the ideal setting to create an exceptional residential enclave.

Black Rock Tpke, Redding

$925,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$350,000

ACTIVE Status ⋅ 24214406 MLS

Create your own private retreat in the heart of Redding Ridge. Set back from the road, this 7.22-acre parcel offers a private setting and the opportunity to bring your vision for a home to life in one of Connecticut's most scenic communities. Raw and undeveloped, the land is zoned for a single building site, offering space to thoughtfully shape a home and landscape around the way you want to live. The property backs to nearly 14 acres of Connecticut DEP-owned land, 48 acres of Aquarion-owned land, and the Aspetuck River. This expansive backdrop offers a meaningful buffer from neighboring homes and enhances the property's exceptional sense of privacy. Whether you envision a timeless country home or a contemporary retreat, this is an exceptional opportunity to own a private piece of Redding and create something distinctly your own. Showings are strictly by appointment only. Do not enter or walk the property unaccompanied.

81 Sport Hill Rd, Redding

$975,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

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