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$1,325,000
5 Beds 4 Baths ACTIVE Status 24175555 MLS
You will take a deep breath as soon as you drive through the beautiful and tranquil landscape of this part of Redding. As you approach the driveway you are greeted by a large antique barn for storing Animals/Cars/Toys. driving down the driveway you see the large colonial farmhouse with expansive front porch 5 bedroom and 4 full baths. The flexible open floor allows for easy daily life as well as being great for entertaining. Kitchen has a huge pantry and large island overlooking a stone fireplace in Living room and dining area. 1st floor ensuite with entrance to front porch(Could be great for in-law, nanny or office.) A Large mudroom leads to an oversized 3 car garage. There is a huge playroom over the 3 car garage. The large patio is a great spot to sun or watch nature. Miles of hiking trails are steps from the front door. The house has a large walk up attic for storage in addition to the 2000 unfinished sq ft in basement with walkout utility garage door.

28 Goodridge Rd, Redding

$15,000
4 Beds 5 Baths ACTIVE Status 24175407 MLS
Privately nestled on over three spectacular acres, this exceptional gated 5 bed/4 bath estate delivers a lifestyle rarely found in Fairfield County. Blending striking architectural design with warm, inviting living spaces, the residence was crafted for both elevated entertaining and everyday comfort.Inside, soaring vaulted ceilings, expansive walls of glass, and dramatic open-concept spaces create an atmosphere that is both sophisticated and relaxed. A chef's kitchen with separate prep kitchen anchors the home, while multiple lounges, recreation spaces, gym, sauna, media room, and a signature English pub offer endless opportunities to unwind and entertain. Outside, the property transforms into a true private resort. Enjoy a sparkling pool and spa, pool house/guest house, beautifully landscaped grounds, and a multi-use sport court designed for tennis, pickleball, basketball, and even seasonal skating. Located just minutes from Westport, Georgetown, Ridgefield, dining, shopping, and train access, this extraordinary furnished rental offers the perfect balance of luxury, privacy, and convenience. Unfurnished option as well.

142 Seventy Acre Rd, Redding

$995,000
4 Beds 4 Baths ACTIVE Status 24138909 MLS
Stunningly renovated Vintage Antique. Up-to-date and yet still very authentic with beams and wide board floors. Set on over 2 level Acres ringed by trees for privacy; includes a lofted barn with possible potential to convert to a 1 BR guest ctg. The kitchen with new stainless appliances, granite and wood floors steps down to the cozy family rm warmed with a wood burning stove, built-in window seat, and sliders leading out to a large stone patio with sunset views. The formal dining rm has a built-in vintage corner cabinet and wide board flrs. The formal living rm also features wide board pegged flrs and is centered with an original stone fireplace updated with rustic gas logs. There is a main flr primary bedroom and ensuite bathrm w blt-ins and a large walk-in closet. Also on the main level in a quiet corner is an inviting library plus a den presently serving as an art studio. The upper level features two bedrooms with wide board floors, beams and antique doors; an updated full bath and a third bedroom presently a home office. In the past, this home served as a two-family so there is a second kitchen with a cork floor on the second flr which opens to a balcony/deck with steps to the private back lawn. The third flr highlights a guest/ in-law space that includes a full bath, bedrm and cozy TV rm. The property explodes with color in the spring and summer with perennials like peonies and hydrangeas and a large fenced garden. Metro North Train to NYC is just around the corner.

Redding

$1,595,000
4 Beds 5 Baths ACTIVE UNDER CONTRACT Status 24157566 MLS
Nestled on three picturesque acres and surrounded by open space, this beautiful country retreat offers privacy, comfort, and exceptional outdoor living. The expansive patio is perfect for entertaining, featuring a full outdoor kitchen, fireplace, TV, and integrated audio system. A large level yard provides plenty of space for recreation and the potential for a pool. Inside, the home showcases high-end finishes and a thoughtful layout. The spacious eat-in kitchen features custom cabinetry, granite countertops, and premium appliances from Thermador, Wolf, and Sub-Zero. The family room is highlighted by dramatic picture windows and a stunning floor-to-ceiling stone fireplace. The main level also includes a welcoming two-story foyer, formal living and dining rooms, a private home office, two powder rooms, and a mudroom with access to the three-car garage. Upstairs, the primary suite offers a luxury bath and dual walk-in closets. Two bedrooms share a Jack-and-Jill bath, while a fourth has its own ensuite. A laundry room and large bonus room complete the upper level. Additional features include radiant heated floors in the kitchen and baths, a home sound system, Generac whole-house generator, security system, irrigation, and unfinished basement. Ideally located in West Redding close to the train, hiking trails, Routes 7 & 84, shopping, and dining.

74 George Hull Hill Rd, Redding

$1,295,000
5 Beds 5 Baths ACTIVE Status 24167807 MLS
Exceptional opportunity for today's buyer! Tucked away in a private, yet neighborhood-like setting, the craftsmanship and beauty of this custom colonial reveals itself the moment you walk through the door. Seamless flow, a sprawling primary suite with fireplace, private office with built-ins and French doors that lead to a porch, as well as a finished basement are just a few of the features that make this home so special. The open-concept kitchen serves as the centerpiece of the home, connecting to the main living areas, including a sun-filled breakfast room, formal dining room, spacious family room, living room, private office, and two powder rooms-perfectly suited for both everyday living and effortless entertaining. The upper level features an expansive primary suite with private sitting room, walk-in closet and a bright, en-suite bath. The additional bedrooms are generously sized and share Jack-and-Jill or en-suite bath configurations. The beautifully designed stone patio and outdoor living area create an inviting space for entertaining and the walk-up attic presents additional storage and opportunity for future customization. With its expansive layout showcasing generously proportioned rooms, custom craftsmanship, and exceptional indoor-outdoor living, this home has so much to offer.

281 Newtown Tpke, Redding

$749,000
4 Beds 4 Baths ACTIVE Status 24149260 MLS
Don't miss the opportunity to live in this special well cared for 8 room Colonial tucked away on 2.93 very private low maintenance acres on sought after Umpawaug Rd, so convenient to Topstone Park, the NY Metro train, walking distance to New Pond Farm, and close to commuting highways and shopping. The welcoming entry hall opens into the inviting light filled living room with a fireplace surrounded with extensive built-in bookcases. Step up to the sunny dining room with built-in corner cabinet, slider to the newer deck and entrance into the eat-in kitchen with ample cabinets and small hallway with access to a powder room and the oversized 2-car garage. Upstairs is the grand primary bedroom with 3 closets and a beautifully remodeled primary bath. There are 3 other bedrooms, all with excellent closets and a hall tub bath. The lower level includes a comfortable family room with a second fireplace and new slider to a patio. The rest of the remodeled walk out basement includes the laundry room, half bath and storage room. Built in 1969, this attractive colonial awaits a few of your personal touches but boasts so many improvements: SEE JULY 2026 IMPROVEMENTS in Documents! Also newer windows, new wood floors on the main level and 2 bedrooms, new hot water heater, and more. See the full list in documents. A SPECIAL HOME AWAITS! PLEASE NOTE: SELLER'S ATTORNEY PREFERS TO USE OWN CONTRACT; SO PLEASE USE THE PLAIN LANGUAGE OFFER IN DOCUMENTS (3rd in the order)

268 Umpawaug Rd, Redding

$1,395,000
5 Beds 6 Baths ACTIVE Status 24161725 MLS
Old Redding charm meets elevated modern living at this exceptional gated Contemporary Colonial offering over 4,700 SF plus approximately 1,800 SF of finished walk-out lower level. Set behind stately iron gates and stone pillars, a private drive leads to a dramatic marble foyer and grand staircase. The custom Clark Construction kitchen, enhanced in 2023, features dual full-size Thermador ovens, Sub-Zero refrigerator, quartz countertops, expansive island, and butler's pantry with additional Sub-Zero, opening to a sun-filled great room w/stone fireplace and wall of windows overlooking private, level grounds. Seamless indoor-outdoor living extends to an expansive deck surrounded by mature landscaping and stone walls. The main level includes a flexible private office suite with multiple entrances, sitting area, bedroom, and full bath, ideal for guests or multigenerational living. Upstairs, the primary suite offers a sitting area, dual-sided fireplace, automated blackout shades, 2 walk-in closets, and spa bath w/steam shower and soaking tub. A secondary suite and 2 additional bedrooms with Jack-and-Jill bath complete the upper level. The walk-out lower level features gym, theater, billiards, and studio space. Notable upgrades include a 26kW generator, new roof (2024), updated HVAC (2025), EV charging, and fully integrated smart home system. Moments to Joel Barlow High School with convenient commuter access, this property offers refined country living with modern luxury.

74 Black Rock Tpke, Redding

$1,599,000
4 Beds 5 Baths ACTIVE Status 24149592 MLS
Sweeping meadow views, privacy & sunsets from an elevated setting 7 Long Meadow Lane is a distinctive property defined by its scale, setting, and versatile layout, offering generous proportions and an architectural presence that supports a wide range of lifestyles. Sited on an elevated, scenic 4.39 acres with exceptional privacy and open meadow outlooks, the home enjoys a peaceful setting surrounded by natural beauty and expansive skies. The interior features light-filled spaces with wide hallways, oversized rooms, and a layout that emphasizes flow and functionality. Multiple living and gathering areas provide flexibility for entertaining, everyday living, and extended stays with family and guests. Large windows throughout capture abundant natural light and tranquil views, with sweeping sunrises and sunsets unfolding across the landscape and changing with the seasons. The home's scale and configuration allow the spaces to adapt naturally over time. Outdoor living is a standout feature, highlighted by an in-ground pool with an expanded patio surround, thoughtfully positioned to maximize privacy and open views. The generous patio provides ample space for dining, lounging, and entertaining, creating a true extension of the home and a resort-like setting for relaxed summer living. Located within reach of NYC yet feeling distinctly removed, the property offers an appealing sense of retreat-ideal as a weekend escape, multi-generational residence, or long-term family compound.

7 Long Meadow Ln, Redding

$14,500
3 Beds 2 Baths ACTIVE Status 24149390 MLS
Available in June for $14,500 and/or July for $20,000. The Otnes House is a true floating oasis and now available as a summer rental! This rolling property overlooks nearly 3.5 acres, complete with a one-of-a-kind pool carved into a natural stone quarry with beautiful surrounding gardens. John Johansen of the celebrated Harvard Five designed this mid-century modern for famous collage artist Fred Otnes, who lived here for over 50 years. Walls of glass bring in beautiful natural light; expansive decks & pergolas have created an open floor plan concept to bring the outside in. The renovated kitchen features Bauformat cabinetry and high end European appliances, and the primary bedroom has a sitting room, office area and attached artist studio. Two additional bedrooms and two bathrooms complete the main house, and adjacent to the home is a two-car garage with ample room for storage or an additional studio space. The property is approximately 50 miles/90min from New York City and 5 minutes to a Metro-North stop which takes you directly to Grand Central. Redding offers an abundance of trails, nearby shops and restaurants of Westport, Darien and Ridgefield. A wonderful place to call home.

26 Chalburn Rd, Redding

$7,400,000
7 Beds 7 Baths ACTIVE Status 24144503 MLS
Another Day in Paradise! Timeless grandeur, architectural mastery, and opportunity define this exceptional plantation-style colonial set on 39.23 acres bordered by 100+ acres of protected forestland-a rare opportunity for stately country living in a singular setting.For the sportsman, pristine woodlands and abundant wildlife offer boundless opportunities for hunting, hiking, and connecting with nature. The residence-a nod to Antebellum architecture-presents grand columns, symmetrical facades, a 97-foot wraparound veranda, and ornate interior design. Every detail has been thoughtfully curated for comfort and quality.Your journey begins with the breathtaking grand foyer flanked by dual staircases and crowned by a soaring domed ceiling artfully decorated with colorful rosettes. Exemplary features include seven fireplaces, an elegant banquet-worthy formal dining room, a chef's kitchen with top-grade appliances, a spacious fireplaced breakfast room, a dazzling sun-filled family room, and two home offices.The exquisite primary suite is a luxurious haven featuring its own artfully adorned domed ceiling, sitting room, and wall-of-glass French doors open to a private balcony with views of the in-ground pool and woodlands. The sumptuous marble bath is a spa-like sanctuary. An invaluable addition to this amazing property is the finished studio over the six-car drive-through garage providing flexible living space. All this and so much more awaits in this extraordinary estate!

63 Turney Rd, Redding

$13,000
3 Beds 2 Baths ACTIVE Status 24133865 MLS
The Otnes House is a true floating oasis and now available as a summer rental! This rolling property overlooks nearly 3.5 acres, complete with a one-of-a-kind pool carved into a natural stone quarry with beautiful surrounding gardens. John Johansen of the celebrated Harvard Five designed this mid-century modern for famous collage artist Fred Otnes, who lived here for over 50 years. Walls of glass bring in beautiful natural light; expansive decks & pergolas have created an open floor plan concept to bring the outside in. The renovated kitchen features Bauformat cabinetry and high end European appliances, and the primary bedroom has a sitting room, office area and attached artist studio. Two additional bedrooms and two bathrooms complete the main house, and adjacent to the home is a two-car garage with ample room for storage or an additional studio space. The property is approximately 50 miles/90min from New York City and 5 minutes to a Metro-North stop which takes you directly to Grand Central. Redding offers an abundance of trails, nearby shops and restaurants of Westport, Darien and Ridgefield. A wonderful place to call home.

26 Chalburn Rd, Redding

$7,495,000
6 Beds 11 Baths ACTIVE Status 24090021 MLS
Welcome to 229 Umpawaug Road, the quintessential estate of exceptional quality on the premier scenic road in Redding, Connecticut in Fairfield County. Surround yourself in luxury inside this sun-filled 6 bedroom, 11 bathroom, 6 fireplaces center hall colonial with a flowing floor plan, formal and informal rooms, embracing the incredibly private 6.5 acres of hand-stacked walls, privacy gates and immaculate landscaping. Numerous patios and outdoor spaces for year-round enjoyment. Dive into the oversized infinity pool with spa and pool pavilion with entertaining bar, full bath and living area. Don't forget your racket, with a private tennis court with California Corners for all levels of play. Private luxury apartment over the heated 3-car garage. This is also a great option for an office or studio. Enjoy all the best of parks, recreation, shopping and dining nearby, also accessible to NYC via Metro North and 56 miles to midtown.

229 Umpawaug Rd, Redding

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