Redding Real Estate

Welcome to Redding, a charming town nestled in Fairfield County, Connecticut. Known for its picturesque landscapes and tight-knit community, Redding offers a peaceful escape from the hustle and bustle of city life.

Situated in the heart of New England, Redding is surrounded by natural beauty. The town is home to several parks and open spaces, including the stunning Devil's Den Preserve, which boasts over 1,700 acres of hiking trails and scenic views. The Saugatuck Reservoir is another popular spot for outdoor enthusiasts, offering fishing, boating, and birdwatching opportunities.

Redding is also rich in history and culture. The town is famous for being the former residence of renowned American author Mark Twain, who found inspiration in the tranquil surroundings. The Mark Twain Library, located in Redding, is a testament to his legacy and offers a wide range of literary events and programs.

In addition to its natural beauty and cultural heritage, Redding boasts excellent schools, making it an ideal place for families. The town also offers a variety of dining and shopping options, with charming local boutiques and restaurants that cater to all tastes.

Whether you're looking to settle down or simply visit, Redding offers a unique blend of small-town charm and natural beauty. With its convenient location in Fairfield County, you'll have easy access to nearby cities like Stamford and Bridgeport, as well as the stunning Connecticut coastline.

Come and experience the tranquility and beauty of Redding, Connecticut – a hidden gem in New England.

Newest Listings in Redding

$1,349,000

5 Beds ⋅ 6 Baths ⋅ 24049650 MLS

Fabulous 5BR colonial with main level primary suite and in-ground pool! Nestled on nearly three gorgeous and level acres is 62 High Ridge Road, which boasts more than 5,800SF of luxurious living and many recent upgrades. Entertaining comes easy in this home with a gorgeous chef's kitchen that leads to a new Trex deck and bluestone patio, an oversized dining room with woodburning fireplace, and a game room (family room) that is lined with floor to ceiling windows and built-ins. You will find an 48" Wolf range with double ovens, island with seating, wet bar, walk-in pantry, and heated tile floors in the eat-in kitchen. The heart of the home is the stunning living room that features a dramatic vaulted ceiling, 2nd woodburning fireplace, exposed beams and window seats. Each room boasts hardwood floors and streams with natural light. In the main level primary suite is a gorgeous full bath featuring double vanities, soaking tub, and large walk-in shower. On the upper level, are two more en-suite bedrooms, and two additional bedrooms that share a hall bath. Tucked away on the far side of the house is a playroom and potential in-law/au pair suite. There is no shortage of fun in this home - family BBQs on the deck, summer parties by the heated in-ground pool, and long evenings in the game room that includes a bar and temperature controlled wine closet. Generator hookup available, two AC units replaced and new well and pool pump installed last year. This is a must-see home

62 High Ridge Road, Redding

$995,000

5 Beds ⋅ 7 Baths ⋅ 24049609 MLS

Extraordinary private setting in sought after Farview Farms neighborhood on 2.40 picturesque acres with stone pillars, gated entry, pool house, heated gunite pool and spa, sport courts, and unlimited potential to restore this home to its former glory. The main home has been gutted to the studs after an unfortunate fire. The silver lining is that no one was hurt, and this is a very unique opportunity to purchase one of the prettiest lots in Redding, in one of the best neighborhoods, with extensive improvements that were untouched by the fire, including Belgian block lined circular drive; free-standing covered porch w/outdoor fireplace; inground trampoline, basketball & volleyball courts; exceptional pool house w/covered patio, kitchen w/custom cabinetry & S/S appliances incl. dishwasher & wine chiller, plus full bath; gorgeous gunite pool w/spa & expansive stone patio; plus the most spectacular landscape & hardscape including stone terraces, walkways, custom bridge, lush mature trees, privacy screening, & flowering gardens. The house fire was contained to the garage & adjoining areas, but there was significant additional damage due to the water used by the fire fighters. The restoration company has been cleaning all of the debris, and much appears salvageable including the well, septic, fully custom wood paneled sun room, and the framework for this house that formerly offered over 7,000 sf on 3 floors with 5 BRs, 4 full/3 half baths, walk-up attic, walk-out LL, & 3 car garage.

25 Farview Farm Road, Redding

$699,000

4 Beds ⋅ 3 Baths ⋅ 24047617 MLS

Welcome to this amazing home in West Redding on 2.38 acres providing plenty of privacy for your peace of mind. Located near western Connecticut's route 7 with easy access to get where you need to be when you're not at home enjoying all the space this home provides. This over 2800 s.f. split-level ranch comes with 4 bedrooms (3 upper, 1 lower), 3 full bathrooms, large living areas upstairs and down, and a screened porch perfect for all seasons. The latest property upgrades include a new central air system, Leaf Filter gutter system, and a Generac 13-kilowatt transfer switch generator to keep you comfortable during any situation. This home is conveniently located just 5 minutes from the Redding train station providing plenty of options for anyone commuting to Stamford, CT (45 minutes) or Manhattan, NY (90 minutes). If the train isn't for you, Route 7 is an easy drive for your daily work schedule. The property provides plenty of usable land for all your hobbies with enough space for parties, bar-b-ques, holiday celebrations, and general recreation including a nicely sized hill for winter snow sledding or a very large 31x18 above ground swimming pool. A fun nature trail on the perimeter within your property line gives you complete privacy for your hiking pleasure. That's right! Take a walk around your property with approximately 0.20 miles per lap giving you safe exercise without leaving your driveway. Tremendous opportunity in bucolic Redding!

107 Simpaug Turnpike, Redding

$1,495,000

24047855 MLS

Welcome to Newtown Turnpike and the opportunity to purchase 3 homes on almost six bucolic acres in the heart of Redding Ct. This property has been in the same family for over 35 years and could be your Generational Compound! With excellent schools and only 90 minutes from NYC, Redding is an idyllic town to call home. Enjoy Country Living! Also listed as individual parcels: MLS# 24047616, MLS# 24047619, MLS#2407624. This Property is held in an estate. Bring your enthusiasm, creativity and vision.

374, 376 & 380 Newtown Turnpike, Redding

$495,000

2 Beds ⋅ 1 Baths ⋅ 24047624 MLS

Welcome to 380 Newtown Turnpike. This two-bedroom cottage is beautifully sited on 2 bucolic acres in the heart of Redding CT.. It's a perfect downsizer, starter home, or weekend retreat. Make this home your own or bring your vision. There are endless possibilities that await. The town of Redding is located near wonderful restaurants, shops, hiking trails, arts, a great escape and just 65 miles to NYC. Make this gem of a cottage your home. This home can be purchased with an option to buy the additional lots and cottages located at 374 and 376 Newtown Turnpike.

380 Newtown Turnpike, Redding

$495,000

2 Beds ⋅ 1 Baths ⋅ 24047619 MLS

Welcome to 376 Newtown Turnpike. This two-bedroom cottage is beautifully sited and tucked back on a bucolic 1.82-acre lot. It's a perfect downsizer, starter home, or weekend retreat. Make this home your own or bring your vision. There are endless possibilities that await . The town of Redding is located near wonderful restaurants, shops, hiking trails, arts, a great escape and just 65 miles to NYC. This home can be purchased with an option to buy the additional lots and cottages located at 374 and 380 Newtown Turnpike.

376 Newtown Turnpike, Redding

$625,000

3 Beds ⋅ 3 Baths ⋅ 24047616 MLS

Welcome to 374 Newtown Turnpike. This home has been in the family for over 35 years. This three bedroom Ranch is beautifully sited and tucked back on a bucolic 2-acre lot. Make this home your own or bring your vision. There are endless possibilities that await . The town of Redding is located near wonderful restaurants, shops, hiking trails, arts, a great escape and just 65 miles to NYC. This home can be purchased with an option to buy the additional lots and cottages located at 376 & 380 Newtown Turnpike.

374 Newtown Turnpike, Redding

$1,395,000

4 Beds ⋅ 4 Baths ⋅ 24045969 MLS

WOW! Exceptional timber frame country home with 4 floors of living on over 6 gorgeous, private acres in one of Redding's most coveted locations. Large gourmet kitchen w/6-burner Wolf range, island and amazing walk-in pantry opens to 35'x35' great room with soaring cathedral beamed ceiling and walls of two-story windows. French doors open to large deck w/stainless steel cable railings w/LED lighting, panoramic vista & sunset views. Main floor primary bedroom, bath, built-ins, and walk-in closet overlooks pastoral back property. Cozy den, office and large laundry room completes the main level. 3 additional bedrooms on upper floor off large open loft area library with another 4th floor loft living area w/vaulted ceiling & built-in couch. Simply spectacular. Finished lower level is currently set up w/office, add'l bedroom, full bath w/separate entrance and could easily be used as an in-law. Tons of storage and plumbed for w/d. 3 bay garage w/oversized doors can accommodate 4 vehicles or equipment. The professionally landscaped grounds are glorious in any season w/fruit trees, mature plantings, perennial gardens & circular drive. Plenty of parking. THE perfect house for entertaining! Many amenities include recently installed whole house generator. Extremely private yet easy access to RT 7, Ridgefield, trains, shops, restaurants and only 60 miles to NYC. You will fall in love with this one-of-a-kind property.

47 Chestnut Woods Road, Redding

$375,000

2 Beds ⋅ 1 Baths ⋅ 24046139 MLS

2 Bedroom Cape on 2 acres. Close to Putnam Park & Huntington State Parks. House in need of TLC. Small pond in rear of home. Good commute area to Down County. Small but cozy.

457 Black Rock Turnpike, Redding

$2,150,000

7 Beds ⋅ 7 Baths ⋅ 24045195 MLS

Welcome to 207 Poverty Hollow Road, a stunning retreat on a tranquil street in Redding. This impressive 2-acre property makes a grand first impression with its elegant half-circle driveway. You'll be greeted by a beautifully landscaped front yard that offers a park-like ambiance. The property features an attached 2-car garage and a detached 2-car garage with an apartment-ideal for an in-law/au-pair suite. Step inside to discover a thoughtfully designed, flowing floor plan with spacious, sunlit rooms. The formal living room, highlighted by a striking spiral staircase, offers a sophisticated space for relaxation. Adjacent, a media room provides versatile entertainment options. The dining room, with its charming exposed beams, comfortably accommodates large gatherings. The chef's kitchen is a culinary haven, equipped with stainless steel appliances, two dishwashers, ample pantry space, and an island bar with seating for four. There's also room for an informal dining table next to the bar area. This kitchen seamlessly connects to a cozy family room featuring a wood-burning fireplace and French doors that open to the patio. Enjoy your morning coffee or an afternoon read in the sunroom, which offers a picturesque view of an entertainer's paradise. French doors lead to the outdoor space with a generously sized table set under a charming pergola, surrounded by lush greenery.

207 Poverty Hollow Road, Redding

$264,900

2 Baths ⋅ 24045043 MLS

Doctor Dentist: Are you looking to own your own practice or expand into a satellite location? Discover this commercial, professional office condo in prestigious Fairfield County. This almost 1,600sf lower-level unit in a two-story building is in a prime location on Route 107 with excellent visibility and easy Metro rail access. Featuring 4 treatment suites & a private consultation office for patients, the entire space is cohesive & professionally designed with upscale decor, elegant moldings, and hardwood flooring. The practice includes a warm, inviting reception area and front desk, plus a lab, sterilization nook, doctor's office with private bathroom, & team break room/kitchenette. Ample free parking is available right outside the door-no more late patients to their appointments who are frantically searching for a spot! Join a distinguished roster of tenants, including Redding Pharmacy, Georgetown Orthodontics, a financial group, & a holistic practitioner. It's like having a "toothsome" lineup of neighbors, making this the perfect place for your dental practice. Hope you decide to check out this "plaque-tastic" opportunity!

73 Redding Road Unit 7, Redding

$1,049,000

4 Beds ⋅ 3 Baths ⋅ 24038433 MLS

Nestled on over three and a half acres, this log house is built like no other. Custom built by the owner himself, he spared no expense in the construction of this home. The exterior is a work of art -- beautiful logs interlocking perfectly with with a majestic stone chimney climbing the side of the house. Upon entering the home, turn left from the foyer to find a generous sized great room with fireplace and open floor plan. The kitchen, with top of the line appliances, opens to the dining area. The main level additionally includes the laundry, powder room and primary suite. Three large bedrooms, a full bathroom and a large storage room can be found upstairs. The basement has a finished living/play area and storage room, an enormous unfinished area for mechanicals, additional storage, and Bilko doors. Above the oversized two car garage is unfinished loft space. The large wrap around porch, made of durable composite material is the perfect place to relax and enjoy the tranquil surroundings. Come take a tour of this true country retreat, set in the town known as "Little Vermont".

59 Sidecut Road, Redding

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