Umpawaug Real Estate

Welcome to Umpawaug, a hidden gem nestled in the picturesque town of Redding, Connecticut, within the scenic Fairfield County. This charming neighborhood seamlessly blends the tranquility of rural living with the convenience of modern amenities, making it an ideal place for families, professionals, and nature enthusiasts alike.

Umpawaug is characterized by its lush landscapes, rolling hills, and serene surroundings. The area is dotted with beautiful homes that reflect a variety of architectural styles, from classic New England colonials to contemporary designs, all harmoniously integrated into the natural environment. The community is known for its friendly atmosphere, where neighbors quickly become friends, fostering a strong sense of belonging.

Nature lovers will delight in the abundance of outdoor activities available in Umpawaug. The neighborhood is adjacent to several parks and nature reserves, offering miles of hiking trails, picturesque picnic spots, and opportunities for birdwatching. The nearby Redding Town Park and the scenic Lake Mamanasco provide the perfect backdrop for weekend adventures, whether you prefer kayaking, fishing, or simply soaking in the beauty of nature.

Families will appreciate the top-rated schools in the area, which are renowned for their commitment to academic excellence and community involvement. Umpawaug is conveniently located just a short drive from the vibrant downtown Redding, where you can find charming shops, delightful eateries, and local events that bring the community together.

In Umpawaug, you’ll discover not just a place to live, but a welcoming community that celebrates the beauty of life in Connecticut. Come explore this enchanting neighborhood and see why Umpawaug is the perfect place to call home!

Newest Listings in Umpawaug

$975,000

ACTIVE Status ⋅ 24188749 MLS

Listing is for 2 previously approved building lots, 4.09 acres and 3.479 acres. Lots have been rough graded, 2 septic's installed, build your dream house, build 2 homes, horse property? property tax is combined amounts of both lots. More photos to come

26 & Rd, Redding

$1,200,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24178497 MLS

Classic New England charm meets modern luxury in this beautifully updated 1921 Colonial. Perfectly situated just minutes from the quaint Georgetown boutique shops , restaurants, and Route 7. Set on nearly half an acre lot, this home offers effortless living and entertaining inside and out. The heart of the home features a renovated eat-in kitchen with timeless marble countertops, a 4 seated island, and newer stainless-steel appliances. Entertain with ease in the formal dining room, unwind by the gas fireplace in the living room, or settle into the versatile sunroom - equally suited as a home office. Upstairs, the primary suite is a true sanctuary, complete with gas fireplace, a spacious walk-in closet and renovated spa-inspired bathroom with soaking tub. Two additional bedrooms and a well-appointed hall bath round out the second floor. The third level offers a wonderfully flexible carpeted family room - ideal as a playroom, media space, or guest retreat. Step outside to a stunning country backyard oasis with a fresh 1,200 square foot bluestone patio equipped with a built in DCS grill and cozy fire pit nook. With its flat, usable property, timeless architectural character, and every major update already done, this home is a rare find in one of Redding's most convenient locations.

207 Redding Rd, Redding

$7,725,000

7 Beds ⋅ 13 Baths ⋅ ACTIVE Status ⋅ 24164249 MLS

Exquisite Nantucket-style country estate magnificently sited on seven sprawling acres in Redding, CT's coveted Umpawaug neighborhood. Comprised of three extraordinary residences, this masterfully crafted 2008 HOBI award-winning compound offers 13,904 sf of carefully constructed living space with meticulous architectural details, effortlessly balancing timeless elegance with modern function. The main residence greets with a sweeping two story entry bathed in natural light, flanked by gracious formal living & dining rooms with fireplaces. The heart of the home, a chef's kitchen with custom cabinetry, high-end appliances, butler's pantry & French doors to an expansive terrace, seamlessly integrated with spectacular grounds. Additional main-level highlights include great room & study with fireplaces, steps from a serene covered porch; mudroom, full bath, & attached three-car garage. Upstairs, a primary suite sanctuary with fireplace, sitting room with wet bar, dressing room with custom cabinetry & spa-like bath with soaking tub & steam shower. Completing the 2nd floor, four additional bedrooms featuring en-suite baths & walk-in closets, family room and laundry. On the 3rd level, 2nd office, gym, half bath & ample storage. Elevator to wine cellar, home theater, billiards room & walkout au pair suite; commercial grade utilities & generator. Award-winning pool house, carriage house with in-law suite, heated gunite pool, spa & manicured grounds complete a remarkable legacy property.

206 Umpawaug Rd, Redding

$499,000

ACTIVE Status ⋅ 24172380 MLS

Glorious interior lot in pine setting on scenic Umpawaug Rd. Owner architect/builder can design and build to suit. See listing #170511696 Owner/agent

65 Umpawaug Rd, 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

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