65 Redding, CT Real Estate Listings

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$899,900Est. Payment
5 Beds | 4 Baths | 3,492 Sqft
18 Great Pasture Road, Redding, CT 06896
House For Sale

FABULOUS Colonial Reproduction home set on nearly 3 gorgeous acres of land. This picturesque property is located on a sought after scenic road, so close to Redding Center, award winning Redding schools and commuter roads/Metro North train. Originally built in 1939, this home has been completely renovated and expanded - MOVE IN READY! The heart of the home is the amazing kitchen! You'll love the high ceilings, wood burning fireplace with heat insert, honed slate counters, deep farm sinks, refrigerator drawers, stainless appliances and the beautiful variegated wide plank oak flooring. The 1st floor boasts a spacious Great Room (current Owner using as home office) & Family Room plus the original house front rooms w/chestnut flooring, hand hewn beams & butler's pantry - ALL with wood burning fireplaces! The 2nd floor has 5 bedrooms w/separate laundry room & back staircase. Enjoy the fireplace in the master bedroom & the renovated dual sink bathroom with private dressing room & plenty of built-ins for your clothing & accessories. Bonus: HUGE walk up attic and 2 lower level basements provide plenty of storage space. Above the 2 car detached garage you'll find a vaulted ceiling 20 x 20 unfinished space - perfect for a home office/half bath (Permits already approved by the Town of Redding) - Ready for the next Owner to easily finish! Gorgeous grounds with flowering gardens, stonewalls, and plenty of outdoor entertaining space on the brick patio. A Redding BEAUTY! Septic system is a 5 bedroom septic and Town of Redding has approved this house as a 5 bedroom house.

$645,900Est. Payment
4 Beds | 3 Baths | 4,100 Sqft
51 Old Stagecoach Road, Redding, CT 06896
House For Sale

Incredible value mini compound with a custom 4BR Contemporary with gourmet Chefs kitchen, Granite, Wolf, Subzero. Luxury master bath with steam shower and spa tub. Large decks front and back with protected location Hot Springs hot tub. Rental/ Guest Cottage currently rented month to month, great to lower your mortgage or have available for your guests/ family. Oversize 3 Car garage with large overhead doors. 2nd flr over garage finished 850sf Office/ Studio Space, great for quiet home office, business owners, artists, writers. All three buildings have separate utilities. Additional .99AC lot part of sale total land 4.27AC. New lifetime 50yr roofs installed all 3 buildings recently. Central AC replaced in main house 2020. Redding Center location, high rated schools. Owner/ Broker.

$850,000Est. Payment
4 Beds | 4 Baths | 3,928 Sqft
32 Dayton Road, Redding, CT 06896
House For Sale

Stunning architect designed contemporary built in 2002 features a creative custom variety of metal finishes & accents, special lighting effects, & dramatic use of fieldstone throughout. Certainly not a typical home, this country casual sophisticate has an open floor plan with so many surprises making it ideal for entertaining and an everyday enviable life style. Two-story window walls & French doors flood the home with natural light. The dream kitchen has stainless steel appliances, ample concrete countertops and a large working island with elevated bronze eating bar. Wide open to the kitchen is the breathtaking Great Rm with soaring 20 foot ceilings & floor to ceiling fieldstone fireplace, an amazing focal point. Formal dining rm w/copper wall has a French door beckoning you to step out onto the private stone patio for alfresco dining. Vaulted ceilinged living room features a gas fireplace, built-ins and French doors to a balcony. Main level master bedroom enjoys a luxurious bath with an oversized steam shower & very large walk-in closet. Custom metal handrails guide you to the upper level hallway overlooking both the Great Room & Living room and lead to 3 generous bedrooms, an office & two full baths. Large lower-level game room walks out to the front yard. Close to extensive hiking trails yet so convenient to Redding's Blue Ribbon Schools, Mark Twain Library, shopping, restaurants and commuter roads & trains to NYC. ENJOY AN IDEAL WEEKEND GETAWAY OR AN EVERYDAY PLEASURE!

Open 3/6
$479,000Est. Payment
3 Beds | 3 Baths | 1,570 Sqft
108 Sport Hill Road, Redding, CT 06896
House For Sale

Charming rebuilt country home in idillic Redding CT. Relax and enjoy the quiet setting near parks, swimming, hiking trails, fishing, horseback riding, golf, tennis and more outdoor activities just 53 miles from New York City. Close to award winning Redding Schools. Redone in 2017 with new everything: New furnace, HVAC system, James Hardie siding, kitchen, bathrooms, flooring, framing, electrical system, patio, fixtures, roof, gutters, windows, doors, plumbing, you name it - it's probably new. For anyone looking for a fully redone, energy efficient, move-in ready house with minimal maintenance and low utility costs - look no further. 3 bedroom, 2.5 bathroom, Master suite w/ walk-in closet, 1,570 square feet 1.05 flat acres. The best deal in town! Tenants in place do not drive up driveway. Owner related to agent.


Laura Freed Ancona

$599,000Est. Payment
5 Beds | 3 Baths | 2,728 Sqft
143 70 Acre Road, Redding, CT 06896
House For Sale

Enchanting Ca 1800 antique farmhouse on most picturesque 2.83 acres in the prestigious and historic Umpawaug area of West Redding. This storied property was part of the original larger farm across the street and was moved to its current location in the 1950s. While subsequently expanded and updated, this very special home retains all of the historic character and charm including the spacious living room with original wide board floors, exposed beams, built-in corner cupboard, and fireplace (as-is). Total 2,728 square feet with 2 car garage, 5 bedrooms and 3 full baths including the gracious main level master bedroom suite with private bath, multiple closets, and French doors to the adjoining deck and hot tub, plus the 2nd main level full guest suite. The first floor also features the inviting dining room with wide board floors and sliders to the rear terrace; paneled library with built-in window seat; plus large kitchen featuring bright breakfast nook with angled bay window, gas range, and French door to the rear patio/gardens. The second floor boasts 3-4 additional bedroom options including the expansive vaulted "great room" with adjoining bath and 3 more lovely rooms. The scenic property includes a sprawling and private backyard with raised planting beds, deck, and acres of walking paths/trails in the rear wooded portion. Top location, convenient to shopping, Georgetown and Ridgefield restaurants, West Redding station and only 68 miles to Midtown from this bucolic setting. Subject to owner finding suitable housing.

Laura Freed Ancona

$2,750,000Est. Payment
4 Beds | 7 Baths | 5,562 Sqft
36 Chestnut Woods Road, Redding, CT 06896
House For Sale

Most spectacular country estate on 11.58 acres with scenic pond in prestigious West Redding location. This breathtaking country compound includes the gracious main home with 5,562 square feet including 1,003 square feet in the dramatic lower level media/bar/billiard room; total 4 bedrooms, 5/2 fully remodeled baths; additional studio or guest quarters with private entry, bedroom and full bath; legal rental cottage with living room, kitchen and full bath (additional 741 square feet); and state of the art pool house (additional 504 square feet). Highest attention to detail both inside and out with apprx $500K in recent improvements by current owner including brand new slate roof; stunning kitchen and baths; new a/c; new lighting; full studio renovation; new pool house; updates in cottage including hardwood installation; full interior painting; fit out of main garage as a catering kitchen; hardwood installation in lower level; sun porch with retractable screen; and so many other tasteful touches which have polished this home to exquisite perfection. Casual elegance abounds with 6 fireplaces including the living room with exposed beams, dining room, paneled library, master bedroom suite, 2nd ensuite bedroom and lower level billiards room. Picturesque grounds with heated gunite pool; private pond; outbuildings including detached garage and barn/shed; plus potential to subdivide and permits in place to build a new large barn if desired. Bucolic privacy adjoining the 54 acre Connecticut Audubon Society's Edward Steichen Memorial Wildlife Preserve and just 61 miles to Midtown!

$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.

$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!

$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 home A 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 th

$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.

$865,000Est. Payment
5 Beds | 4 Baths | 3,877 Sqft
75 Fire Hill Road, Redding, CT 06896
House For Sale

Picture perfect! This welcoming colonial, with its beautiful front porch, is nicely situated on a cul de sac locale in West Redding, near Ridgefield. Unpretentious and warm, the home has an understated elegance and charm. The double storied foyer, flanked by the dining room to one side and living room to the other, makes quite an impression. One room flows into another, allowing for flexibility of use and function. The light filled family room with stone fireplace, merges indoor and outdoor spaces. That room connects to the living room, screened-in porch and deck and is adjacent and open to the spacious and well appointed eat-in kitchen (granite counters, center island with butcher block, Miele dishwasher, Thermador double wall ovens, Samsung fridge, and Wolfe 5 burner gas cooktop). The butler's pantry features a glistening brass sink, wine rack and mini fridge. Also on the main level are a powder bath, laundry room, access to 3 car garage and a bedroom/den. A surprise awaits at the top of the back staircase, a home office/gym. Up the front staircase, 4 generously sized bedrooms can be found; 2 of which are en-suite and the other 2 share a Jack and Jill bath. The unfinished, walkout basement (roughly 1,852 sq ft) offers unlimited possibilities. 20 KW Generac generator and new Trane air conditioning system. 2.15 acres w/stone walls, mature plantings and large lawn area, a portion of which is fenced in (pet friendly). Sale subject to sellers finding suitable housing.

$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

$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!

$600,000Est. 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.

$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.

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