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63 Homes For Sale in Redding, CT

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New
$1,195,000Est. Payment
6 Beds | 5 Baths | 5,268 Sqft
28 Bridle Road, Redding, CT 06896
House For Sale

Country living meets waters edge. The bucolic 2-acre setting, encompassed by mature trees, boasts a sweeping lawn that gently slopes to a serene pond providing recreational enjoyment + captivating scenic views year-round. Distinctive 6-bedroom home features a silo that serves as a sitting area + loft. Legal apartment with kitchen, living room, bedroom and full bath in the barn. High-end custom millwork throughout the homes 4,124 sq ft, as well as in the 1,144 sq ft finished walk out lower level. Oak wood floors and wide-plank heart pine boards from Carlisle. Expansive living room window provides peaceful views. The ambience is enhanced by the fireplace, mantel and surround are antique wood from 18th century France. Gourmet kitchen will delight: handsome cabinetry, island, a breakfast area overlooking the pond + top-of-the-line appliances highlighted by a cast-iron AGA stove. The romantic first floor master suite boasts a cathedral ceiling, stained glass window, amazing views of the pond and marble bath. The family room w/Vermont Castings wood-burning oven, and office w/built-in desks, open to an amazing patio w/built-in outdoor kitchen, fire pit + hot tub, captivating views of the pond, encompassed by stone walls and lush landscaping for an enchanting setting. Garden-to-table lifestyle starts in the kitchen garden. The climate-controlled 1,000-bottle wine cellar is sure to please. Two sets of 2-car garages bookend the home. A Rambling Treasure in an Enchanting Setting.

New
$1,100,000Est. Payment
5 Beds | 3 Baths | 2,841 Sqft
44 Dayton Road, Redding, CT 06896
House For Sale

Private Country Compound on almost 3 park-like acres. The MAIN HOUSE is a 5BR Saltbox reproduction. Highlights include an updated Chef's Kitchen with soapstone counters, marble topped baking station, stainless appliances, farm sink, Butler Pantry, Fireplace, large Breakfast Nook, Mudroom with Laundry and a stunning Stone Patio for outdoor dining. The oversized Family Room has a second Fireplace and Built-ins. A Formal Dining Room, Study with third Fireplace and a Full Bath complete the main level with hardwood flooring throughout. Front and Back Staircases lead to all 5 Bedrooms. A full unfinished Walk-up Attic offers future expansion and storage. The CARRIAGE HOUSE with almost 4000 contiguous sq ft offers multiple spaces. The POOL HOUSE with direct access through french doors to the In-ground heated Pool with beautiful gardens including a Wisteria Arbor, a 1 BR COTTAGE (per Town Records) with 2nd BR potential, large Loft overlooking Full Kitchen, a Full Bath, Laundry Room and large Deck, STUDIO GUEST QUARTERS with Full Bath and Kitchenette, a huge WORKSHOP, a 2 Car Garage and a 1 Car Garage. Also on the property is a 200 year old BARN, originally from the Danbury Fair Grounds, that was reassembled here and has 3 Stalls, Tack Room, Electric and Running Water. There is also an established fenced in Garden (originally the Paddock), Half Basketball Court and a Chicken Coop. Miles of hiking trails at Devils Dens. This is a very special and unique offering.

New
$850,000Est. Payment
4 Beds | 5 Baths | 4,221 Sqft
32 Glen Hill Road, Redding, CT 06896
House For Sale

Connecticut Rambler at the end of a cul de sac. This house will not disappoint. Close to Route 7, Branchville Train Station, shopping and restaurants, yet privately located in a neighborhood setting. Gorgeous chefs kitchen with butlers pantry, 6 burner Viking stove with griddle, large stainless refrigerator, two dishwashers and Bosch double ovens with warming draw. Prep sink two refrigerator drawers and granite counters. Kitchen opens to family room with fireplace and dining area which leads to multi level decking to include a hot tub on your way to the in-ground pool! Main level master with spa bathroom, walk in closet, vanity and sitting room opens to the deck. Two other bedrooms and full bath complete this level. Up the stairs you will find a fourth bedroom with full bath and space with wet bar that can be used as a study or exercise room. Plenty of storage on this level. If this isn't enough, there is a lower level one bedroom with den in law suite with full kitchen (no dishwasher), living room and full bath. Lower level has a private entrance or can be accessed through the house. Garage has custom made large closets for storage. House has RING security, generator hook up and so much more!

New
$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.

New
$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.

New
Open 3/7
$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.

New
$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!

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.

$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.

$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 Road, 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

$1,175,000Est. 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!

$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

$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!

$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!

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