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241 Black Rock, Redding
$4,000,000
6 Beds ⋅ 11 Baths ⋅ 170562604 MLS
Love life? Love it even more when you arrive home to this exquisite Normandy Chateau with all the special attributes you would expect from a luxurious estate. Set on over 19 acres of lush property, the setting is nothing but idyllic with beautiful gardens, wide open pastures, koi ponds and scenic water views. The best surprise is how inviting & comfortable the home truly is. Of course, there are the fabulous formal living & dining spaces one would expect to find, and a chef's kitchen any culinarian would find a delight, but the amenities are what make this residence one-of-a-kind. Start your staycation lounging at the pool, then enjoy lunch al fresco on the terrace, relax in the sauna and then meet up at the bar for a cool beverage. After dinner, take a sunset sail in the canoe on the pond and then catch a movie in your private theater. Still not ready to end the evening? Head up to the recreation room for a game of ping pong or chess. Retire to the first-floor primary bedroom suite with a spa-like bath & two-story custom/cedar closet. Each of the five family bedrooms has a full bath & unique nook for imaginative play. Just a few of the many special features: European-style windows, reclaimed wood beams, antique slate roof tiles, a potting room. Highly sophisticated infrastructure with a fire sprinkler system, four high-efficiency Buderus boilers, generator, two floors of radiant heat & more. Install paddock and barn & bring the horses. Come & love life in Redding, CT!

241 Black Rock, Redding

40 Deer Hill Rd, Redding
$1,225,000
4 Beds ⋅ 4 Baths ⋅ 24169044 MLS
Tucked away on a quiet, tree-lined street in the center of town, 40 Deer Hill Road offers the rare balance of privacy, comfort, and everyday convenience. The moment you step inside, you are greeted by cascading natural light from a dramatic wall of windows. At the heart of the home is the main living area, an inviting space anchored by a fireplace, soaring cathedral ceilings, and windows that frame the changing seasons and bring the outdoors in. Just beyond, the deck serves as a private retreat, perfect for morning coffee or summer dinners overlooking the serene property. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring a center island, double ovens, and generous space to gather. With comfort and flexibility in mind, the home also features a first-floor primary suite with a fireplace, private deck, dual walk in closets and a spacious primary bath w/oversized shower and soaking tub, creating a true retreat. The main level is rounded out with a second bedroom, 2 additional baths, dining room, & an office. Upstairs are 2 large bedrooms sharing a full bath. A bonus room above the garage offers versatility, ideal as a second office, playroom, media room, or guest space. With extensive improvements, peaceful surroundings, and a location that offers convenient access to town, schools, commuter routes & dining, this is a home that effortlessly combines everyday ease with the space to relax, gather, & truly enjoy.OFFER DEADLINE TUES 4/28 12PM

40 Deer Hill Rd, Redding

6 Winding Brook Ct, Redding
$1,050,000
5 Beds ⋅ 3 Baths ⋅ 24173873 MLS
**Final offers due by Monday 5/18 at 5pm** Tucked at the end of a cul-de-sac down a long private driveway, 6 Winding Brook Ct offers the rare balance of quiet living and everyday convenience. Surrounded by mature landscaping and nature, this classic 5-bedroom Colonial captures the warmth and character so many buyers are searching for, while still being just minutes to Georgetown's restaurants and cafes and Redding schools. Built in 1971 and thoughtfully designed for both gathering and retreat, the home features beautifully scaled living spaces filled with warmth and charm. The inviting living room centers around a traditional wood-burning fireplace, while the spacious family room-with its dramatic fieldstone fireplace-serves as the heart of the home. Just beyond, a screened-in porch offers the perfect setting for morning coffee, al fresco dining, or quiet evenings listening to the sounds of nature. The eat-in kitchen offers a layout that comfortably supports modern living, flowing naturally into the home's gathering spaces. A dedicated office/library lined with built-ins creates an ideal work-from-home or reading retreat, while the dining room strikes the perfect balance between classic and comfortable.

6 Winding Brook Ct, Redding

194 Lonetown Rd, Redding
$1,020,000
5 Beds ⋅ 4 Baths ⋅ 24129438 MLS
Tucked away on more than three acres, this light-filled contemporary offers space, style, and flexibility in one of Fairfield County's most desirable towns. With 5 bedrooms, 3.5 baths, and over 3,100 square feet, the home is designed for everyday comfort as well as year-round entertaining. The main level highlights dramatic architecture with vaulted ceilings and walls of windows that frame the outdoors. A chef's kitchen with center island connects seamlessly to the dining room, sunroom, and deck, all overlooking the 20x40 heated pool. The private main-level suite includes a sitting room, gas fireplace, spa bath, and walk-in closet. The lower level features three additional bedrooms and a large family room with French doors, creating plenty of space for guests or play. An in/law suite with its own entrance, kitchenette, and full bath is ideal for in-laws, an au pair, or a home office. Just minutes from the train, Redding Country Club, and scenic parks-and less than 90 minutes to Manhattan-this property combines the best of country living with everyday convenience.

194 Lonetown Rd, Redding

45 Great Pasture Rd, Redding
$975,000
4 Beds ⋅ 3 Baths ⋅ 24071709 MLS
Antique lovers, prepare to fall in love! The historic Deacon Samuel Read house, a Federal style colonial, built in 1745 by the founding family of Redding, CT. Enter the stunning 11 X 24 entry hall with exquisite millwork, a gracious sweeping staircase and original wide plank oak floors that run throughout the house. 9+ foot ceilings on the first floor enhance the elegant formal living room and dining rooms, each with a wood burning fireplace to warm your guests. The spacious Sun room with stone floors looks out on the beautifully landscaped, sloping property. A "new" addition built in 1857 includes a cozy family room with a 3rd wood burning fireplace and access to a charming porch where you will sit in the warm weather and enjoy the designated scenic road in front of the homestead. An office/bedroom sits between the family room and the large country kitchen. The dining area in the kitchen opens to a stone patio that leads to the heated in-ground pool. There is a powder room area with a separate shower also on the main level. At the top of the staircase is a large landing area where you will find three generous sized bedrooms and 2 full baths. There are two attic areas that offer expansion possibilities. This property must be seen to fully appreciate the unique character and exudes from every corner. Redding CT is considered "a slice of Vermont" within 60 miles of New York. Come be awed by the area and this magnificent home!

45 Great Pasture Rd, Redding

90 Old Stagecoach Rd, Redding
$955,000
4 Beds ⋅ 3 Baths ⋅ 24132001 MLS
This Contemporary-style home offers space, privacy, and a peaceful connection to nature. With 3,080 square feet of thoughtfully designed living space, this 4-bedroom, 2.5-bath home combines modern comfort with a warm, open feel. The dramatic two-story foyer, cathedral ceilings and lots of large windows welcomes you with natural light and a feeling of openness, perfect for both everyday living and entertaining. The updated kitchen features generous workspace, granite counters, center island, Miele stainless steel appliances and a seamless flow to the dining and living areas. Each room feels spacious and inviting, offering plenty of flexibility for your lifestyle. Step outside to an expansive, two-level Trex floored deck with built-in planters and benches offering a perfect spot for morning coffee, gatherings with friends, or simply taking in the tranquility. Complete with a 2-car attached garage, this home is sited on 2.31 acres and tucked well back from the road by a long, gravel driveway with plenty of parking spaces for guests. Across the street, conservation land with scenic trails invites you to explore the outdoors right from your doorstep. Recent upgrades that add to the home's comfort & reliability include New Miele dishwasher (2025), New ice maker (2025), Freshly painted interior (2025), Refinished main-level hdwd floors (2025, 2022), New well tank (2025), New well pump (2025), New central air conditioning system (2023), New washer & dryer (2021). See Virtual Tour!

90 Old Stagecoach Rd, Redding

94 Old Stagecoach Rd, Redding
$915,000
4 Beds ⋅ 3 Baths ⋅ 24129197 MLS
Welcome to this absolutely turnkey and beautifully updated 4 bedroom, 2.5 bath center-hall Colonial offering stunning curb appeal, an open floor plan, and a prime location in the heart of Redding. Set on a quiet, walkable street close to schools and town center, it offers the perfect blend of comfort and convenience. Inside, light-filled spaces have been thoughtfully opened up for modern living. The main level showcases a spacious layout with a large kitchen featuring a center island, custom cabinetry, Bosch and Thermador appliances with gas range and dining area that seamlessly flows into the family room, living room with wood-burning stove and home office. A convenient mudroom connects the home and garage for everyday ease. Upstairs are 4 generous bedrooms, including a serene primary suite with large bathroom and closet, a hall bath for the additional bedrooms, and bright versatile flex space up the back staircase above the garage - perfect as a playroom, studio, or lounge. A large unfinished basement offers abundant storage or potential gym/playroom. Extensive upgrades include new central A/C (2025), Marvin windows and James Hardie siding (2022), a complete kitchen remodel (2018) and a 16x12 shed (2024). Every detail has been done-simply move in, unpack, and start enjoying life at 94 Old Stagecoach Road!

94 Old Stagecoach Rd, Redding

28 Winding Brook Ln, Redding
$900,000
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

37 Lamppost Dr, Redding
$840,000
4 Beds ⋅ 3 Baths ⋅ 24175748 MLS
Highest and best due 6/1/@ 4PM Nestled on a quiet cul-de-sac in desirable West Redding, this inviting 4 bedroom, 2.5 bath home offers the perfect blend of comfort, space, sustainability, and commuter convenience. Located in a town affectionately known as the "Vermont of Connecticut," Redding is cherished for its scenic wooded landscapes, top ranked schools, and peaceful atmosphere. Inside, a thoughtfully designed floor plan provides both functionality and warmth. The spacious front to back living room features a classic wood burning fireplace, creating the perfect gathering space for relaxing or entertaining. A formal dining room with beautiful built in banquet cabinets, while a private home office offers flexibility for today's work from home lifestyle. A standout feature is the expansive bonus room, currently used as an art studio, offering endless possibilities as a playroom, media room, gym, or creative space. Upstairs, four generously sized bedrooms and two full baths provide comfortable accommodations for family and guests alike. Outdoor living is equally inviting. The large screened in porch is the ideal place to enjoy a quiet morning coffee or unwind with an afternoon cocktail while taking in the peaceful surroundings. Just beyond, the paver patio creates the perfect setting for roasting marshmallows, entertaining guests, or simply enjoying the idyllic scenery that makes Redding so special.

37 Lamppost Dr, Redding

10 Shady Ln, Redding
$630,000
5 Beds ⋅ 3 Baths ⋅ 24135649 MLS
Charming Ranch-Style Home with In-Law Potential in Beautiful Redding awaits, if your are looking for your first home or your next one, opportunity knocks in the heart of Redding on a quiet cul-de-sac. This spacious & versatile ranch-style home offers the perfect blend of comfort, functionality, & small-town charm. Step inside the main level, where you'll find a warm & inviting sunken living room with a gas fireplace, hardwood floors, and plenty of natural light. The spacious eat-in kitchen is just waiting for your design ideas. This level also features 3 bedrooms and 2 full baths, providing comfortable one-level living. Downstairs, the fully finished walk out LL opens up a world of possibilities. With its own kitchen, full bath, living room with fireplace, 2 bedrooms, & an office this flexible space walk-outs to the backyard-perfect for use as an accessory apartment, in-law suite, guest quarters, or extended family living. Additional highlights include a 2-car garage, a private yard, and endless potential. Located on a quiet cul-de-sac take advantage of a wonderful opportunity to make this home your own with personal updates and touches. Located in the scenic and welcoming town of Redding, known for its award-winning schools, quaint town center, & over 17 beautiful town parks and nature preserves-you'll enjoy a lifestyle surrounded by nature, yet still close to major amenities. Schedule your private showing today and discover all that Redding living has to offer

10 Shady Ln, Redding

6 Old Mailcoach Rd, Redding
$575,000
2 Beds ⋅ 2 Baths ⋅ 24119322 MLS
A Magical Country Cottage! This charming retreat is an intimate and cozy escape set among the trees and filled with history. It is rumored to have been the home of the blacksmith for the Barnum & Bailey circus in 1899. The home features 1-2 bedrooms and 1.5 baths, a completely remodeled kitchen with high-end appliances, white cabinets and quartz countertops. The luxurious full bath features a soaking tub and is also completely renovated. Imagine waking to the gentle chirping of birds and enjoying your morning coffee on the deck or screened-in porch while bathed in the soft glow of natural light filtering through the trees. The rustic barn hints at a simpler time and offers endless possibilities, from a creative studio to additional storage or even a quaint guest space. This property is more than a home; it's an opportunity to embrace a tranquil lifestyle!

6 Old Mailcoach Rd, Redding

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