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

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

Timeless elegance meets exceptional value, a truly "must see" home. This exceptional custom-built 5-bedroom, 5-bathroom Colonial offers 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,

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

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

Live your best life in this timeless 2003 Ridgefield Colonial. Situated on 1.57 acres of level land at the end of a serene cul-de-sac, this home offers ultimate privacy, surrounded by nature and protected land. Step inside to discover four bedrooms and five bathrooms across 4,174 square feet on the main and upper levels, with an additional 1,788 square feet of partially finished lower-level

Ashley Hamedi Compass Connecticut, LLC

A rare opportunity to own a thoughtfully updated antique home with a separate guest cottage, set on 1.66 picturesque acres in Redding, blending timeless character with modern livability in a way that is increasingly hard to find. A welcoming foyer with a vaulted ceiling sets the tone, leading into a sunlit living room anchored by a gas fireplace, custom built-ins, and a large picture window. The

Brianna Carvalho Compass Connecticut, LLC

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 a rare combination of privacy, scale, and opportunity. Set on 2.62 lightly wooded acres framed by mature trees and stone walls, the property invites a lifestyle connected to nature

Julie Setterlund William Pitt Sotheby's Int'l

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

Jessica Christ Coldwell Banker Realty

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

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

Serenity awaits in this classic colonial nestled on two level acres in a walker-friendly cul de sac neighborhood. This turn-key home has perfect flow for entertaining. French double doors off the spacious, quartz countered kitchen open up to the sun-soaked four season room with the light and bright great room attached featuring skylights, cathedral ceilings, a fireplace, and a bar area. The bonus

Katherine Fassman Higgins Group Real Estate

Welcome to this well maintained 3-bedroom, 3-bath Colonial ideally situated on a quiet cul-de-sac with stunning front yard views and a peaceful setting. This spacious home offers an inviting layout designed for both comfortable living and entertaining. The sun-filled living room flows seamlessly into the formal dining room featuring a bay window overlooking the picturesque front yard. The custom

Lynne Murphy Berkshire Hathaway NE Prop.

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

Welcome to 121 Picketts Ridge Rd - A truly one-of-a-kind retreat at 121 Picketts Ridge Road, a sprawling custom-designed ranch privately set on 2+ lush acres bordering protected watershed land & preserved open space. Offering exceptional one-level living, this remarkable residence features 11 spacious rooms, including a private in-law apartment or ideal home office with separate entrance, vaulted

Brian Appel Higgins Group Real Estate

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

Set in the heart of charming Redding, Connecticut, this meticulously maintained home offers the perfect blend of New England character, modern efficiency, and everyday convenience. Known for its award-winning schools, scenic walking trails, and peaceful, serene surroundings, Redding provides an exceptional lifestyle-and this property places you right in the center of it all, just minutes to the

Mia Capella William Raveis Real Estate

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

Completely reimagined from top to bottom, this beautifully renovated Redding residence offers the comfort, efficiency, and peace of mind of a newly built home. Every major system and finish has been replaced, including a brand-new roof, siding, windows, doors, plumbing, electrical, and a new central A/C and heating system, ensuring modern performance and long-term reliability. Inside, the home

Thomas Casey Live Real Estate LLC

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

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.