Redding, CT Homes for Sale

Welcome to this expansive and beautifully updated six-bedroom Colonial, offering three full and two half baths and thoughtfully positioned on a sprawling 2.42-acre lot that provides both privacy and presence. A grand wraparound driveway creates a striking approach to the home, offering ample parking in addition to a two-car attached garage ideal for guests, entertaining, and everyday convenience.

Jonathan Gineo Silver and Oak Realty

***Exceptional Value in Redding CT*** A refined Connecticut country residence for full-time living or weekend enjoyment. Set on nearly three meticulously landscaped acres on a private cul-de-sac drive with only 4 residences, you will enjoy living in one of Redding's most desirable residential enclaves. 2 Longwood Drive offers a safe, secure, and sophisticated country lifestyle that resonates

Jeffrey Kaplan William Raveis Real Estate

Set on over 2 private acres in a coveted neighborhood in SW Redding, this sun-filled 4 BR Colonial blends timeless style, scale and effortless living. Designed for both entertaining and daily life, the main level centers around a spacious EIK w/center island, all-new appliances and seamless flow to the adjoining family room w/gas fireplace. Sliders open to the deck and grounds beyond, creating an

Brianna Carvalho Compass Connecticut, LLC

Nestled on a tranquil cul-de-sac in bucolic Redding, this expansive 3,650 SqFt, 4 bedroom, 3.5 bath classic Colonial has been completely re-imagined and renovated, both inside and out. This 11 room home offers 5 fireplaces; a new eat-in kitchen with oversized island and large dining area with a wood burning fireplace; step-down living room with fireplace; formal dining room with custom millwork.

Michael McKee William Pitt Sotheby's Int'l

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,

Brianna Carvalho Compass Connecticut, LLC

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

Brianna Carvalho Compass Connecticut, LLC

Welcome to this exceptional custom-built 5-bedroom, 5-bathroom Colonial offering over 5,000 square feet of thoughtfully designed living space. Set on 2.88 acres off a private driveway, this home showcases generously proportioned rooms throughout and provides an ideal balance of comfort, functionality, and refined living. The well-appointed, open-concept kitchen serves as the centerpiece of the

Alexis Bennett Coldwell Banker Realty

Nestled on three private acres in highly sought-after Redding, Connecticut, with a private backyard gate entering directly into Topstone Park, this exceptional property offers a lifestyle defined by tranquility, privacy, and space. Surrounded by mature trees and drenched in natural light, the home embodies the timeless charm that has earned Redding its reputation as the 'Vermont of Connecticut".

Giuseppe 'Joe' Melillo William Raveis Real Estate

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

Tyler Toren Compass Connecticut, LLC

Custom-built in 2004 and meticulously maintained, this 2.18-acre home offers a true escape from the everyday. Surrounded by perennial gardens, stone walls, and specimen trees, the grounds are anchored by a stunning stone patio-your own private sanctuary for quiet mornings or lively entertaining. Inside, discover 3,669 square feet of sun-drenched living space featuring 11 rooms, 4 bedrooms, and

Paul Gervais William Pitt Sotheby's Int'l

Highest & Best Offers due 5PM TUESDAY, 4/14.Welcome to this sophisticated country Cape blending modern living with charm in Weston's Georgetown area. White picket fences & stepping stones through an arbor welcome you to the front porch of this beautiful home! Set at the end of a quiet cul-de-sac on a level acre w/inviting circular driveway, the open floor plan creates comfortable flow for

Dianne DeWitt Berkshire Hathaway NE Prop.

Set on over six private, lightly wooded acres, this expansive single-level home offers more than 3,500 square feet of living space in a highly desirable Redding location, just 3 minutes to the West Redding train station with direct access to Grand Central. Hardwood and tile flooring run through the main living areas, with carpeted bedrooms for comfort. The home features a sunken living room with

Luke Eddinger Robert C White & Company LLC

Welcome to 123a Peaceable St. West Redding, Connecticut | 4 Bedrooms | 3,594 Square Feet | 2.62 Private Acres. Tucked away at the end of a quiet cul-de-sac in highly desirable West Redding, this classic Colonial offers the rare combination of privacy, scale, opportunity. Set on 2.62 lightly wooded acres with stone walls.Built in 1988 and offering 3,594sqft above grade, the home unfolds w/

Julie Setterlund William Pitt Sotheby's Int'l

Experience modern luxury in this beautifully renovated Colonial. A grand double-door entry opens to a bright foyer. The all-new gourmet chef's kitchen boasts a massive waterfall quartz island, high-end appliances, and pot filler. The open-concept main level flows into a spacious living room with brick fireplace, while a secondary family room features a dramatic floor-to-ceiling stone fireplace

Natalia Rathbauer William Pitt Sotheby's Int'l

This antique home is a blend of rustic charm and modern finishes. You'll love the spacious & extremely accommodating living and dining rooms that allow for memorable gatherings. A large room on the main floor with adjoining half bath could be an ideal guest room, office or primary bedroom, allowing this home the possibility to live like a 4 bedroom. Original beams throughout the home not only

Cher Iravani Redevelopment Realty Group

Tucked away, off the beaten path and down a quiet country lane, this charming 4-bedroom, 2.5-bath Cape Cod home offers a peaceful retreat surrounded by nature. With more than 2,300 square feet of living space, this well-loved home combines warmth, character, and endless potential. The main level features two bedrooms, a full bath, and a flexible layout that includes a kitchen, dining room and

Susan Warner-Lambert Carbutti & Co., Realtors

Welcome to your dream home located just steps from Devil's Den Park Trail. This beautifully updated property offers comfort, space, and privacy on nearly one acre of land. The home features a new roof and new siding, along with freshly painted interiors and hardwood floors throughout. There are new light fixtures that add a clean and modern feel to every room. The kitchen has been fully updated

Nikolina Kajtazovic Coldwell Banker Realty

Welcome to 18 Ledgewood, a beautiful Contemporary home offering 2,900 square feet of well-proportioned living space in a desirable Redding, Connecticut setting. This 4-bedroom, 3 full bath home features a flexible layout with a potential main-level 5th bedroom and full bath, ideal for guests, extended family, or a private home office. The home offers generously sized living and dining areas with

Brian Christy William Raveis Real Estate

Set on a level 2-acre property, bordered by over 200 acres of protected nature preserve with scenic trails, this exceptional home offers a rare blend of privacy, convenience, and outdoor beauty. The grounds are meticulously landscaped with exquisite stonework, creating stunning garden spaces, while an oversized backyard deck with a firepit provides the perfect setting for entertaining or relaxing

Tony Zaccardo Coldwell Banker Realty

Tucked away like a storybook retreat, 71 Picketts Ridge is a charming and cozy ranch-style home that lives like a private condo alternative, set on two secluded acres and reached by a long, winding driveway that opens to the peaceful serenity of the woods. Surrounded by nature and complete privacy, this special property offers the perfect blend of tranquility and convenience. Recently remastered

Kyle Neumann Houlihan Lawrence

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

Marilyn Sloper Coldwell Banker Realty

Nestled on a picturesque country road in the heart of Redding, this National Register of Historic Places landmark offers a rare blend of 18th-century soul and modern New England estate living. The home's historic integrity is preserved through twin stone chimneys, original wide-plank flooring, and exquisite period woodwork. Sun-filled living spaces flow seamlessly from the warm central hall to a

Susan Gardella William Pitt Sotheby's Int'l

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

Stacy Young William Raveis Real Estate

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

Linda Sweeny William Raveis Real Estate

Welcome to 31 Longview Drive in Ridgefield. Set on 1.21 acres, this 3 bedroom, 2 full bath home offers comfortable everyday living with central air, a cozy fireplace, and a 2 car attached garage. The 3 season enclosed porch is a great space for morning coffee, casual dining, or unwinding while overlooking the yard. Downstairs, the fully finished basement adds valuable flex space for a rec room,

Dylan Longmuir eXp Realty