55 Houses For Sale in Redding, CT

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Open 2/28
$569,000Est. Payment
3 Beds | 3 Baths | 2,141 Sqft
14 Wood Road, Redding, CT 06896
House For Sale

Escape the city life to enjoy the charming town of Redding voted one of the Best CT towns to live in! This friendly community located in the heart of Fairfield County and just 60 miles to Midtown Manhattan, is committed to excellence in education, maintaining open space and preserving its historical and natural resources. Know as the "Vermont of Connecticut" Redding is host to summer concerts on The Green, a local farmers market, vibrant local restaurants and pubs, a Boys and Girls Club, a community center with programming for all ages, athletic fields, public tennis courts, Redding Country Club, and a thriving year-round local arts and music community. 14 Wood Road is located between Putnam and Huntington Parks where you will find over 1,000 acres, trails and lake. Updates of this fine home include open concept renovation, built-in entry cabinets, newer roof, windows, gutters, garage doors, driveway, kitchen and bathrooms. Additionally, the home has an open airy feel with tons of windows to enjoy the wonderful seasonal lake views. Pack your bags and enjoy creating your own memories.

$1,175,000Est. Payment
5 Beds | 6 Baths | 7,526 Sqft
9 John Todd Way, Redding, CT 06896
House For Sale

First time to market! This custom-built, 5 bedroom, 6 bathroom (4 full + 2 half) colonial in north Redding sits on a gracious plot of 8+ acres. Surrounded by picturesque woods and beautiful rock outcroppings, this property has unmatched features and has been engineered for easy living. Privately located on a cul-de-sac and surrounded by recently updated landscaping, this property features 6 separate garage bays perfect for the car enthusiast. The formal, two-story foyer provides access to all areas of the home including a library, a formal dining room, a sizable family room with built-in wet bar, a chef's kitchen with Subzero fridge, commercial gas range and an appliance pantry to keep the countertops uncluttered. One bedroom is located on the first floor, great for guests. Take one of the two staircases to the second floor to find 3 more bedrooms, 2 more bathrooms, plus main bedroom suite including its own sitting room with fireplace, and an opulent hotel-like en suite bathroom. A hidden feature exists on the third floor which is a private, fully wired home office allowing you to work from home without disturbances. From there you can access the house's widow walk to catch the beautiful sunsets over the hills, or watch meteors on a starry night. The fully-finished 2161 Sq Ft lower level has endless possibilities and is currently set up with multiple game rooms, movie room, purpose-built art room, and also includes a half bath and walk-out. This truly is the ultimate retreat!

$835,000Est. Payment
3 Beds | 3 Baths | 2,518 Sqft
52 Topstone Road, Redding, CT 06896
House For Sale

Converted Barn/Farmhouse -- best address and location. 4 beautiful level acres of meadow and woods and includes raised bed organic garden, attached 36' Greenhouse and Gazebo overlooking neighboring Steichen Pond. Originally part of the famed Edward Steichen estate, this charming country home is light and bright throughout with fabulous versatile 3 floors of living. Hardwood floors, structural beams, built-ins, and Fireplace. Large Living and Family Rooms plus main floor Office or Den. Immaculate white cooks Kitchen opens to Patio and Greenhouse. Two-car Detached Garage with Loft ready for finishing for studio/office or simply storage. Tucked away from it all on Topstone Road, a designated scenic road, yet minutes from Ridgefield, RT 7, trains, shops and restaurants. One hour to NYC. One of Redding's gems.

$579,000Est. Payment
3 Beds | 3 Baths | 1,640 Sqft
39 Beeholm Rd, Redding, CT 06896
House For Sale

Charming hideaway in the desirable Georgetown neighborhood, minutes away from local parks and train station. This property has lots of open space, a babbling brook runs through the property, and rock gardens with many rare plants originally crafted by members of the American Rock Garden Society. Upon entry to the property, you will see the spacious garage, the walls of which are beautifully hand-constructed with local stone. The walkways and stone walls throughout the landscape are all handcrafted by the homes original owner. The home offers remarkable details; custom built-in bookshelves span the living room walls, as light floods the space through a wall of windows overlooking the backyard rock gardens and brook. Each of the three bedrooms on the main floor includes large windows facing the stunning brook and rolling hills. The cozy basement has plenty of storage, work, and entertainment space, as well as direct access to a back patio with it's outdoor cooking space. The stone room located in the basement is a true masterpiece, its walls and fireplace were entirely hand-laid by the original owner. Throughout the house you will find plenty of nooks ideal for reading, relaxing, and creative activities. Across the brook sits a picturesque old barn with rare arched beam entrances. Beside the barn is a greenhouse, which overlooks the brook. This unique haven has endless potential, call to schedule your showing today. MULTIPLE OFFERS, HIGHEST AND BEST DUE BY TUESDAY 2/16 @ 10am

$2,775,000Est. Payment
4 Beds | 5 Baths | 4,009 Sqft
42 Meeker Hill Road, Redding, CT 06896
House For Sale

Less than 90 minutes from NYC tucked away in the lush green woods of Redding, CT and being sold fully furnished is a modern, stunning at every turn home set on 5 acres with everything you need to live life and focus on what really matters. The perfect country retreat.This custom-built home has been designed to embrace nature with meticulous attention paid to every detail. All features in the home were thought out by the owner in collaboration with Charles Allem of CAD International. Beginning with the ten-foot custom pivot glass door to the floating walls and fully recessed mood lighting. This home is designed to celebrate nature. The Nano Walls and windows bring the outside in and allow for enjoyment and entertaining throughout the four seasons. A minimalistic, clutter free approach to living.Exquisite views from every window bring the garden and nature into the homeA cantilevered staircase hand crafted from a 50ft sheet of metal floats in the entrance.The living room features a functioning fireplace fashioned from a slab of Italian marble accentuating the 25-foot soaring ceiling. The fully retractable Nano Walls create an unobstructed view of the sundeck, pool and luscious garden, bringing the outside in. A dining room that seats 10 comfortably illuminated by a Holly Hunt mobile light fixture. With retractable Nano Walls on one side and black lacquered pocket doors sectioning off the kitchen. Custom designed chefs kitchen with a 10-foot island, a Gagganau fridge, freezer and wine fridge, a 6 burner Wolf stove, grill and griddle plus two ovens. The spacious butlers pantry is complete with its own Viking stove, Subzero Fridge/Freezer and Miele dishwasher. And oodles of room for storage.Master bedroom suite with retractable Nano Walls leading to the deck overlooking the pool and garden. Master bathroom with a walk-in closet, rain shower and its own private bathroom garden and patio.A spacious upstairs includes an open plan office with a balcony overlooking the pool

$875,000Est. Payment
5 Beds | 6 Baths | 5,673 Sqft
38 Deacon Abbott Road, Redding, CT 06896
House For Sale

Welcome home to 38 Deacon Abbott Road! This expanded colonial is situated on 2 park-like acres on a desirable cul-de-sac in Redding center. This light, bright and spacious home is move-in-ready and offers the flexible floor plan that todays discerning buyer is looking for. With enough space to spread out, yet ample room to gather, you will enjoy entertaining in this light-filled home. Enjoy cooking in the chefs kitchen that opens to the family room and sunroom, both of which feature cathedral ceilings and oversized windows. The rear corridor offers a workspace with views of the beautiful property. Unwind in the great room that features coffered ceilings, a fireplace, and water fountain. Retreat to the master bedroom that is separate from the other four bedrooms and features vaulted ceilings and a large master ensuite with soaking tub, shower, and walk in closets. Enjoy the many other features that make this home so warm and comforting. Redding, often referred to as the Vermont of Connecticut, offers award winning schools, endless opportunities for outdoor recreation and the Mark Twain Library, and all within an hours drive to NYC!

$779,000Est. Payment
4 Beds | 3 Baths | 4,348 Sqft
155 Gallows Hill Road, Redding, CT 06896
House For Sale

Looking for a quiet, private retreat where you can relax & enjoy beautiful sunrises, sunsets & observe nature? Nestled at the end of a quiet cul-de-sac sits this meticulously maintained Colonial. Appealing features include elegant flr to ceiling entrance w curved stairway, 3 FPLCS, designer kitchen, oversized wrap around deck & stunning spa like MSTR BTH. The well designed gourmet EIK w custom cabinetry, double ovens, HUGE granite ctr island w striking chandelier like pendants, murano glass backsplash & copper sink has cozy sitting area by the FPLC. 2 sets of sliding doors open from the KTCH to the expansive deck. Spacious FRM w FPLC & built ins also has sliders to the deck. 1st fl Office adjacent to FBTH can serve as GST RM. Formal DRM w bay window & front to back LRM w FPLC complete the 1st flr. 2nd flr features a generously sized MBRM w huge WIC & fabulous bath w oversized shower, stylish claw foot soaking tub, tile floor, custom granite double sink vanity. 3 add'l BDRMS w spacious closets complete the 2nd flr. Finished w-out BSMT w wonderful light allows for 2nd FRM, Game RM, Gym/Home Office. 3 car garage. Redding CT boasts an excellent school system and is a town that values safety & preservation of open space. Enjoy hiking trails, private golf course, biking, kayaking...a perfect retreat from city life but close enough for add'l venues of entertainment & culture. Freshly painted, Automated standby generator, hardy board exterior, immaculate! Just move in!

Laura Freed Ancona

$899,000Est. Payment
4 Beds | 4 Baths | 4,144 Sqft
8 Chapman Place, Redding, CT 06896
House For Sale

Exceptional 2003 custom colonial in top West Redding location, set back privately on 2.2 picturesque acres adjoining Redding Land Trust open space. The park-like setting includes expansive level front and back yards; Belgian block lined driveway to the 3 car garage; 2 decks plus brick patio for outdoor enjoyment; convenience to the West Redding MTA station, shopping/restaurants in Ridgefield and Bethel, plus only 61 miles to Midtown. Impressive construction, appointments and attention to detail with 9' ceilings, moldings, French doors, hardwood floors, plus open flow. The welcoming two story foyer offers French doors to the private library; wide cased opening to the adjacent living and dining rooms; and views to the dramatic two story family room with floor to ceiling fieldstone fireplace plus back stairway to the second floor with balcony overlook. This great room serves as the central hub for gracious living and entertaining with the adjoining sunny breakfast room featuring angled wall of windows/French slider to the deck and true cook's kitchen showcasing center island with bar overhang, stainless steel appliances including double ovens, Absolute black granite counters and Carrera marble tiled backsplash. Total 4,144 square feet with 4 bedrooms, 3/1 baths including the elegant master bedroom suite with double walk in closets and lux private bath with marble topped double vanities, separate shower, and jetted tub; plus additional ensuite bedroom and 2 more with shared Jack and Jill bath. Total 1,565 square feet partially finished in walk-out lower level with potential for game, recreation room and in-law/au-pair suite.

$1,175,000Est. Payment
5 Beds | 5 Baths | 4,556 Sqft
37 Chalburn Rd, Redding, CT 06896
House For Sale

Peaceful waterfront home, custom built by Master Builder Theodore Dachenhausen is set on 10+ acres of beautiful park-like landscape. The home was designed with the outdoors in mind, nearly every room offers a view of the beautiful shared lake and private pond. The main level has an open floor plan perfect for entertaining; the stately living room is inviting and serene with its marble fireplace and large sliders leading out to the wraparound deck. Enjoy dinners with a view in the formal dining room; the beautiful and bright eat-in kitchen is the perfect spot to enjoy your breakfast. On nice days enjoy your coffee out on the deck. After a day of swimming and fishing in the summer or skating and playing hockey in the winter, retreat to the master suite with its large master bath. The marble fireplace and private balcony being the ideal place to watch the sunset over the lake, this is the perfect place to spend a relaxing evening at home. The main level has 2 additional bedrooms and 1 and a half baths. The spacious lower level offers lots of living space, the large family room with stone fireplace, office area, 2 bedrooms, and 2 full baths. Large sliders offer access to a screen in patio as well as outdoor patio area. This home has the ideal location, a short drive to Ridgefield Town Center, and approximately 60-minute drive to New York City. You will not want to miss your opportunity to own this special home, call today to schedule your showing.

$509,000Est. Payment
4 Beds | 3 Baths | 1,850 Sqft
26 Pine Mountain Road, Redding, CT 06896
House For Sale

Simplicity...A Great Home in a Fantastic, Desirable South Redding Neighborhood. Terrific Sun-Washed Open Floor Plan Home Offering 3/4 Bedrooms with 2.5 Baths. The Bright Living Room has a Vaulted Ceiling with Skylight & Cozy Wood-Burning Fireplace. The Relaxed Dining Room has Sliding Glass Doors that Lead to the Peaceful Screened Porch with Stairs to Private Yard & Huge Deck. Back Inside the Cheerful Eat-in-Kitchen is Welcoming & Clean-lined with New Stainless Steel Range & Moveable Island. The Casual Master En-suite has a Updated Bath with Tiled Shower. The Additional Bedrooms are Good in Size & all Offer Hardwood Floors. The Finished Lower Level with Large Family Room has a Wood-Burning Fireplace & is Ideal Space for Gaming or Movies. The Adjacent Extra Room with Closet is Versatile & can Serve as a 4th Bedroom or Home Office. The Laundry & Mud Room with 1/2 Bath are Located here too & has Convenient Walk-out Access to the Rear Deck. Great Area for Barbecues, Games & Outdoor Fun. The Sprawling Enchanting Property is Situated on 2.5+ Acres with your very Own Hiking Trails! Features Include: C/A, Younger Roof, 200 Amp Service, Portable Generator, Updated Baths, Oversized 2 Car Garage, & Shed. Perfect Location, Close to all Amenities & Just a 1/2 Mile to the Branchville Train Station (Metro-North) to NY. Redding, is a Warm Small Community Known for it's "Small Town, Big Outdoors". Enjoy 2 State Parks, Mark Twain Library, Topstone Park, New Pond Farm, Award Winning Schools.

$595,000Est. Payment
3 Beds | 2 Baths | 1,486 Sqft
6 Old Dimon Road, Redding, CT 06896
House For Sale

An original midcentury modern built in 1955 and designed by Edward Lloyd Flood, an architect employed by Edward Durrell Stone, allegedly a student of Frank Lloyd Wright. These are the 2nd owners in 66 years! Many aspects built into the home were revolutionary and cutting edge at the time including radiant heat, poured concrete floors, passive solar, and walls of glass. Built as a single-story home, the focus was to create a space that felt as though you were protected by the elements yet still living in the dramatic beauty of the surrounding wooded area. Large overhangs surround the 12 floor-to-ceiling windows and 13 glass doors (every room has a doorway and stunning view to the great outdoors), that give you unobstructed views to the outside its picture perfect for your viewing pleasure. Radiant floor heating throughout provides a gentle warmth to the floor. The back-to-back insert woodstoves set into the large see-through fireplace (living room to a cozy reading room), create a nostalgic and homey feeling. Exposed western cedar beams are in every room of the house. Double French doorways from almost every room, lead to outside gardens and patios. Open the doors for a cross breeze. Two sides of the property border the untouched (+ untouchable) Aquarion Watershed property. Devils Den Nature Preserve (the largest tract of protected land in Fairfield County), and hiking trails can be reached from your front door with ease. 65 miles to mid Manhattan. See attached video.

Laura Freed Ancona

$929,000Est. Payment
4 Beds | 6 Baths | 6,106 Sqft
96 Hopewell Woods Road, Redding, CT 06896
House For Sale

Exceptional colonial set back privately through stone walled entry featuring Belgian block lined circular driveway and most picturesque 2.14 acres with scenic views of neighboring pond plus nearby Putnam State Memorial Park, "CT's Valley Forge" with 183 acres of hiking trails. This immaculate home offers 6,106 square feet of living space on 4 finished levels including walk-up 3rd floor and walk-out lower level with 4-5 bedrooms and 4/2 baths. Attention to detail abounds with custom moldings, mill-work, hardwood floors, and built-ins throughout; plus light and bright with open flow including the dramatic vaulted family room featuring floor to ceiling fieldstone fireplace flanked by custom built-in display shelving; wide open to the expansive cook's kitchen with sunny angled breakfast room, wet bar, island with bar seating, and back hallway to private library, mudroom, plus 3 car garage. The gracious entry foyer leads to both the elegant formal dining room and living room with custom built-in shelving/cabinetry, plus 2 story stairway to the 2nd floor offering: lux master bedroom suite with angled sitting area, double walk-in closet and private bath; 2 additional bedrooms with Jack andJill bath; plus 4th bedroom with hall bath. Walk-up to the expansive finished 3rd floor with multiple uses as office, art/yoga studio, recreation room or gym with half bath. The spacious finished lower level offers further room to spread out with additional private guest, au-pair or in-law suite, full bath, recreation room, office, plus media room with 2nd fieldstone fireplace and French doors to the expansive backyard. Park-like setting yet only 66 miles to Midtown!

$1,199,000Est. Payment
4 Beds | 5 Baths | 4,400 Sqft
4 Meadows Edge, Redding, CT 06896
House For Sale

If a private and secluded natural setting is what you are looking for, don't miss this quintessential Connecticut colonial! Set back from the road and backing up to a nature preserve, is this gorgeous, meticulously maintained custom colonial. This elegant home has flowing living spaces, huge custom kitchen, four bedrooms, a dramatic family room with stone fireplace, and dining and living rooms. Outdoor space has an expansive quartz stone patio, freshly painted exterior, new herringbone brick walkway, three-car attached garage and possible pool site. The gorgeous extensively landscaped yard, has a fenced in vegetable garden. This wonderful colonial is close to Georgetown, Redding center and trains. Welcome home!

$1,600,000Est. Payment
6 Beds | 5 Baths | 4,083 Sqft
150 Seventy Acre Road, Redding, CT 06896
House For Sale

One of the most beautiful properties located among Umpawaug Estates. The setting is unparalleled from its sweeping lawns, manicured gardens, 2-story open porch, stone patios, stone walls, wisteria covered stone arbor and in-ground heated pool. The 1880 neoclassical style Colonial is a perfect blend of old and new - original character and craftsmanship - beautiful moldings, arched doors, built-ins, wide board flooring - yet has been updated with all the expected modern luxuries. Highlights include the well appointed Chef's Kitchen - large island, 2 beverage drawers, 2 dishwashers, stainless appliances, honed granite counters, walk in Pantry with open flow to the Family Room and Dining Room - ideal for entertaining. The Sun Room with walls of windows overlooks the gardens. The Master Bedroom Suite is its own wing. The Bedroom is grand in size and has a gas fireplace, walk-in closet fitted with custom organization, private Full Bath and a private deck overlooking the beautiful grounds. All secondary Bedrooms are ensuite with updated private or Jack and Jill Baths. Additional outbuildings include the rustic 1 BR COTTAGE/POOL HOUSE built in 1890 with Kitchen and Full Bath w/Laundry. The BARN with the capacity to house 3 additional cars is currently being used as an Indoor Sport Court. The detached 3 CAR GARAGE has a private Office/Studio above for those WFH. Redding offers miles of trails to explore, award winning schools and is 60 miles to NYC.

Laura Freed Ancona

$699,000Est. Payment
3 Beds | 4 Baths | 3,342 Sqft
139 Old Redding Road, Redding, CT 06896
House For Sale

Exceptional modern craftsman style home on 2 level acres in top West Redding location adj. 280 acre Topstone Park w/picturesque lake used for swimming/kayaking plus nature trails. Just moments to both West Redding/Branchville train stations and the Ridgefield border for shopping/restaurants, plus only 60 miles to Midtown. This impeccable home has been upgraded throughout with top of the line designer appointments and open flow including state of the art kitchen/great room showcasing Wolf and Sub Zero appliances, soapstone counters, stone floor, French doors to the rear deck, and one of a kind English Elm island, open to the beamed/vaulted family room with wall of windows and built-in media console. The open concept main level also features hardwood floors; crown moldings; dining room with sliders to the deck overlooking the private backyard with wooded views; vaulted living room with sleek fireplace and contrasting rustic beamed mantle; plus private office/optional bedroom with built-in desk/cabinetry and Murphy bed. Total 3,342 square feet including 3-4 bedrooms, 3/1 baths, and 640 square feet in the walk-out lower level. The 2nd floor features the elegant master bedroom suite wtih top of the line newly remodeled master bath offering concrete topped double vanity and frameless shower, plus 2 additional spacious bedrooms with shared hall bath. The finished lower level features a recreation/media room; climate controlled 400+ bottle wine cellar; separate dog/mud room with adjoining outside fenced kennel/pen; plus full bath with dog shower. Subject to owner finding suitable housing.

$660,000Est. Payment
4 Beds | 3 Baths | 2,100 Sqft
207 Lonetown Road, Redding, CT 06896
House For Sale

Wonderful opportunity to start the summer in a newly-built home surrounded by a level yard and 4+ acres of quiet privacy, scheduled for spring completion. Light-filled open floor plan with four bedrooms, three full baths & the walk-out lower level all offer the flexibility in function so necessary for today's lifestyle. Features inc gas fireplace & hardwood floors on main level, 12' ceilings, family room & 4th bedroom with full BA in lower level, perfect for office/guest. There is still time to choose finishing details. Located near the center of Redding, less than 5 minutes to Redding Elementary School, the Community Center with tennis courts & community gardens, and Concerts on the Green held every Sunday during the summer. Redding, a small town focused on enjoying nature ~ 100's of miles of hiking trails, kayaking in Huntington State Park, swimming at Topstone, and wandering around gorgeous New Pond Farm ~ offers an unrushed lifestyle with small scale, award-winning schools, the iconic Mark Twain Library (The Pudd'nhead Festival, juried Art Show, the Frog Frolic), family-owned farm stands, breweries, and the Umpawaug Farm Winery. Bethel's Greenwood Avenue, with small shops, gourmet grocery, and excellent restaurants, is a 5-minute drive north. Ridgefield, offering endless restaurants, entertainment & a charming Main Street, is 10 minutes away. The Merritt Pkwy, Long Island Sound beaches, and Westport shopping is a no-highway, 25-minute drive.

$525,000Est. Payment
4 Beds | 4 Baths | 3,724 Sqft
23 Ridgewood Drive, Redding, CT 06896
House For Sale

Seeking ultimate privacy? Look no further! Situated at the end of a cul-de-sac and a private driveway sits this classic 11 room, 3700+ sqft, 4 Bedroom/ 3.5 Bathroom, center hall colonial situated on 2 acres & surrounded by 200 acres of open-space woods. Central A/C, 4 fireplaces, hardwood floors throughout the home (even under wall-to-wall carpet), 2 cedar closets, whole house backup generator, large fenced-in back yard, beautiful mature plantings, finished walk-out lower-level w/ in-law potential and more. Beautiful Redding awaits... townofreddingct.orgSchedule your private showing today

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