Redding Real Estate

Welcome to Redding, Connecticut – a hidden gem nestled in the picturesque Fairfield County! Known for its stunning natural beauty and charming rural character, Redding offers a perfect blend of tranquility and community spirit, making it an ideal place to call home.

Redding is renowned for its lush landscapes, with over 1,000 acres of parkland and nature preserves. The scenic trails of the Redding Land Trust provide residents with endless opportunities for hiking, biking, and enjoying the great outdoors. The town is also home to the tranquil Lake Waccabuc and the serene Putnam Park, perfect spots for family picnics, fishing, or simply unwinding amidst nature.

This quaint town boasts a rich history, with well-preserved colonial architecture and a vibrant arts scene. Redding's cultural offerings include local galleries, theater productions, and community events that foster a strong sense of belonging among residents. The town also hosts various farmers' markets and seasonal festivals that celebrate local produce and crafts, showcasing the best of what Redding has to offer.

Families will appreciate Redding's highly-rated schools, which provide a nurturing environment for children to thrive academically and socially. The town's commitment to education is evident in its dedicated educators and robust extracurricular programs.

With its easy access to major highways and proximity to bustling cities like Danbury and Norwalk, Redding offers a serene escape without sacrificing convenience. Whether you're seeking a peaceful retreat or a vibrant community, Redding, CT, is a wonderful place to explore, live, and grow. Come discover your dream home in this enchanting town!

Newest Listings in Redding

$419,900

1 Beds ⋅ 2 Baths ⋅ 24194246 MLS ⋅ Georgetown Place BLDG.

Welcome home to this charming, light-filled condo in the heart of Georgetown! Featuring an open floor plan with soaring vaulted ceilings and a ceiling fan, this inviting home is filled with natural sunlight and offers a bright, airy feel throughout. The thoughtfully updated interior includes beautiful laminate flooring (2020), a new dishwasher (2022), washer and dryer (2022), range and microwave (2023), and major mechanical updates completed in 2025, including a new heating system, electric heat pump, and hot water heater, providing comfort and peace of mind for years to come. A newer smoke detector with a 10-year battery adds another valuable update. The versatile loft offers endless possibilities as a home office, fitness area, guest room, or creative space. The spacious primary bedroom features a walk-in closet, and the home also includes a very large storage unit for all your extra belongings. The exterior of the building was freshly painted in 2024, enhancing the property's curb appeal. With its blend of modern updates, flexible living space, and convenient Georgetown location, this move-in-ready condo is one you won't want to miss!

56 Portland Ave Unit 3, Redding

$1,800,000

4 Beds ⋅ 5 Baths ⋅ 24193453 MLS

A once-in-a-generation offering. Once part of the Redding's historic Samuel Clemens (Mark Twain) estate, this extraordinary 5.41 acre property was later home to renowned American Abstract Expressionist painter Robert Natkin, whose creativity inspired its remarkable evolution. Set beside the 161-acre Stormfield Preserve, this secluded private compound offers miles of hiking trails just beyond your doorstep. The understated approach gives way to an unforgettable interior where architecture masterfully employs "compression and release". Step through the glass entry and the home unfolds to a spectacular designer-renovated chef's kitchen with Wolf range/double ovens, Sub-Zero refrigerator, quartz waterfall island, wet bar and a full wall of glass that opens creating seamless indoor-outdoor living to the screened porch, heated saltwater pool and sweeping grounds, ideal for entertaining on any scale. Every principal room captures views of the surrounding landscape, creating a seamless connection to its setting. A climate-controlled studio with 9' glass garage doors opening to the landscape-equally suited as an art studio or fitness space. Designed for multi-generational living with first and second-floor primary suites, three ensuite bedrooms, guest/in-law/au pair apartment, workshop, entry gallery and temperature controlled pole barn for collectors, equestrians, car enthusiasts or hobbyists. R-2 zoning on 5.41 acres offers possible subdivision potential with due diligence.

24 Mark Twain Ln, Redding

$999,500

4 Beds ⋅ 4 Baths ⋅ 24190805 MLS

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 includes a center island, butler's pantry, and casual dining area, while separate formal living and dining rooms provide additional space for gatherings. Upstairs, the primary bedroom includes a walk-in closet and a freshly renovated en suite bathroom. Three additional bedrooms and an expansive recreation room offer flexible space for a home office, playroom, or a media room. The finished walkout lower level provides even more living space, with a full bathroom, ample storage, a workshop area, and a separate room well suited for an office, gym, or hobby space. A large backyard deck and pergola ideal for entertaining complete the property. The home is located in a sought after location with close proximity to Huntington and Putnam Memorial State Parks.

380 Black Rock Tpke, Redding

$1,329,000

5 Beds ⋅ 5 Baths ⋅ 24191583 MLS

The Rebecca Denison Homestead, established in 1708 with the present Greek Revival residence built in 1824, is a rare historic offering that beautifully combines architectural significance with modern-day living. Listed with the Connecticut State Historical Commission, this exceptional property is privately situated on 2.37 park-like acres and showcases timeless craftsmanship, meticulous maintenance, and thoughtful updates throughout. Offering more than 4,100 square feet of living space, this distinguished 12 room residence features 5 bedrooms, 4 updated full baths, and an updated half bath. Details include the original historic front door, exposed beams, paned windows, hardwood floors, five fireplaces (one gas fireplace in the family room and four wood-burning fireplaces), and abundant natural light throughout. Designed for both elegant entertaining and comfortable everyday living, the home offers gracious living and dining spaces with exceptional versatility, including a private entrance to a potential home office, study, or guest suite with Jotul cast iron gas stove. The chef's kitchen serves as the heart of the home, featuring high-end appliances, modern finishes, a large center island, generous pantry with prep sink, additional refrigerator, and abundant workspace. The kitchen flows seamlessly to the expansive deck, creating a wonderful indoor-outdoor living experience.

286 Black Rock Tpke, Redding

$1,995,000

2 Baths ⋅ 24191067 MLS

Church campus located in the Georgetown section of Redding, consisting of a one story frame bi-level religious facility and a single family dwelling. The campus also includes a separate residential building lot containing +/- 0.76 acres known as 36 Portland Ave. The church and house are well maintained and have parking for more than 50 cars. With a total land area of +/- 2.2 acres, the property lends itself to a wide variety of development or expansion options.

44 Portland Ave, Redding

$899,000

4 Beds ⋅ 4 Baths ⋅ 24189050 MLS

Expansive colonial home on 2.62 private acres in top West Redding location with mature trees & flowers, stone walls, large deck for outdoor enjoyment, & 3 car garage. This light-filled home offers a grand foyer with two story staircase, open to the adjoining living room & dining room for ease of entertaining. The elegant living room features custom millwork including the impressive coffered ceiling & custom fireplace surround. Gather family & friends in the lovely oversized dining room with graceful arched opening & hardwood floor. The heart of this spacious home is the 29' kitchen with center island & sunny dining area with walls of windows & French door to the deck. The kitchen opens directly to the soaring vaulted family room with dramatic floor to ceiling stone fireplace, skylights, built-in display shelving, hardwood floor, & double set of French doors to the inviting deck and sprawling level side yard. There's room to spread out on the second floor too - the stylish primary suite offers a vaulted ceiling, third fireplace, more custom built-ins, huge walk-in-closet, plus marble bath with double vanity, jetted tub, & separate shower. There are three additional spacious bedrooms, all with hardwood floors, including one with a private half bath, plus the shared hall bath, convenient laundry room, and back stairway. Don't miss the huge lower level & attic with tons of storage. Idyllic natural setting, yet moments to shops, restaurants, train, & just 60 miles to Midtown.

123a Peaceable St, Redding

$910,000

4 Beds ⋅ 4 Baths ⋅ 24189421 MLS

Nestled on a quiet residential loop in one of Redding's desirable neighborhoods, this beautifully maintained 4-bedroom, 3 full and 1 half bath center hall Colonial offers timeless design, generous living space, and a secluded setting surrounded by mature landscaping. The gracious floor plan begins with a large living room that flows seamlessly into the formal dining room, where dramatic floor-to-ceiling windows fill the space with natural light and provide beautiful views of the yard. The kitchen combines warmth and function with rich wood cabinetry, soapstone countertops, stainless steel appliances, a large eat-in area, and generous workspace for everyday living. A butler's pantry between the kitchen and dining room provides additional storage, a prep sink, a desk/work area. The inviting family room features a classic fireplace, an oversized picture window, and hardwood floors. A screened porch and expansive deck overlook the backyard, offering an ideal setting for outdoor dining, relaxing, or entertaining. A highlight - the bonus suite above the garage, featuring a full bath and walk-in closet. Ideal as an in-law or au pair suite, guest quarters, home office, or recreation room. Upstairs, the primary suite is complemented by three additional bedrooms, including one with a charming loft that creates a unique retreat for reading, play, or additional sleeping space. This exceptional Colonial offers flexible living spaces, comfort, and a peaceful setting.

28 Winding Brook Ln, Redding

$869,900

3 Beds ⋅ 3 Baths ⋅ 24150713 MLS

Welcome to 119 Peaceable Street! Set on over 5 private acres in one of Redding's most picturesque settings, this lovingly maintained 3-bedroom, 3-bath home is being offered for the first time by its original owners. Thoughtfully cared for throughout the years, the home reflects pride of ownership at every turn. Large windows throughout the home flood the interior with natural light, creating bright, inviting living spaces while framing beautiful views of the surrounding property. Freshly painted inside and out and featuring a new water heater, this move-in-ready home offers the perfect balance of comfort and peace of mind. Step outside to your own private retreat, where an in-ground pool is surrounded by mature landscaping and serene natural beauty. Whether entertaining guests, enjoying a quiet morning coffee, or unwinding poolside, the setting offers exceptional privacy and tranquility. Rarely does a property combine this level of seclusion, natural beauty, and meticulous care. A unique opportunity to own a cherished home with over 5 acres of land in the heart of Redding.

119 Peaceable St, Redding

$65,000

24188701 MLS

Nestled in a peaceful setting, this lightly wooded property offers an ideal blend of privacy, natural beauty, and everyday convenience. With approximately 150 feet of road frontage and R-2 zoning, this property presents a wonderful opportunity to bring your vision to life. Enjoy the serenity of country living while remaining just minutes from shopping, dining, parks, schools, and commuter routes. Private well and septic required. Buyers to verify all information independently.

14 W Woodland Dr, Redding

$975,000

24188749 MLS

Listing is for 2 previously approved building lots, 4.09 acres and 3.479 acres. Lots have been rough graded, 2 septic's installed, build your dream house, build 2 homes, horse property? property tax is combined amounts of both lots. More photos to come

26 & Rd, Redding

$625,000

2 Beds ⋅ 2 Baths ⋅ 24187187 MLS

Discover the quintessential Redding lifestyle in this charming circa 1898 home, perfectly positioned to enjoy the town's excellent schools, open space, and recreational opportunities like hiking, fishing, and kayaking. This 2/3 bedroom (3rd bedroom being used as a study) residence features a 3-bedroom septic system, central air and 2 full bathrooms, offering versatile living options. Step inside to discover timeless character with original hardwood floors and high ceilings. The living areas and 2 bedrooms are highlighted by four fireplaces-three decorative and one fully functional with a heater insert - adding warmth. The dining room boasts exposed beams, original leaded glass windows while newer windows throughout the remainder of the house ensure modern efficiency. Relax and unwind on the inviting covered and screened front porch. Need flexible space? The partially heated basement has been used as a home office, and a newer, spacious shed on the property offers endless potential as a workshop or a creative studio. Additionally, existing expansion plans-drawn up by previous owners-are available to help you visualize future possibilities (not submitted for town approval). Ideally located for an easy commute, you are just moments from Joel Barlow High School and the convenient shopping hubs of Bethel and Georgetown. A rare opportunity to embrace the peace of Redding living while staying connected to it all.

78 Black Rock Tpke, Redding

$435,000

1 Beds ⋅ 2 Baths ⋅ 24181361 MLS ⋅ Georgetown Place BLDG.

Nestled in the charming village of Georgetown, this sun-filled first-floor end unit offers over 1,700 square feet of thoughtfully designed living space and a rare opportunity for convenient single-level living. The main level features a spacious one-bedroom primary suite with abundant windows that fill the home with natural light. The bright and inviting kitchen flows seamlessly into the dining area, creating an ideal space for everyday living and entertaining. A generously sized living room offers comfortable gathering space, while updated flooring throughout adds a fresh, modern touch. The finished lower level expands the living space with a large family room featuring a cozy fireplace, an additional bedroom or flexible office space, a full bathroom, laundry room, and ample storage. Move right into this light-filled home and enjoy all that Georgetown has to offer, including local dining, nearby train stations for easy commuting, and the convenience of Caraluzzi's just moments away.

56 Portland Ave Unit 9, Redding

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