Umpawaug Homes under $1.25 million

Welcome to Umpawaug, a hidden gem nestled in the picturesque town of Redding, Connecticut, within the charming Fairfield County. This enchanting neighborhood is characterized by its serene landscapes, lush greenery, and a tight-knit community that exudes warmth and hospitality. With its tranquil atmosphere, Umpawaug is the perfect retreat for those seeking a peaceful lifestyle while still enjoying the conveniences of suburban living.

The homes in Umpawaug offer a delightful mix of architectural styles, from classic New England colonials to modern contemporary designs, all set against the backdrop of nature’s beauty. The real estate market here has a range of options, with many stunning properties available for under $1.25 million. These homes often feature spacious layouts, expansive yards, and modern amenities, making them ideal for families or anyone looking to enjoy a comfortable lifestyle.

Residents of Umpawaug benefit from easy access to outdoor activities, with numerous parks and nature trails just a stone’s throw away. The community is also known for its excellent schools, making it a desirable location for families. Additionally, the vibrant town center of Redding, with its charming shops and restaurants, is just a short drive away, offering a taste of local culture and cuisine.

Whether you’re looking for a peaceful retreat or a place to raise a family, Umpawaug offers a unique blend of tranquility and community spirit. Explore the opportunities that await you in this delightful neighborhood, where your dream home is just around the corner!

Newest Umpawaug Homes under $1.25 million

$1,100,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217394 MLS

Idyllic country charm meets modern luxury in this turnkey Cape Cod home, nestled on 3.24 private acres complete with your own tranquil, spring-fed pond! Step inside through a dramatic two-story entry to find gleaming, richly-hued hardwood floors flowing seamlessly throughout the entire home. Thoughtfully designed for both entertaining and everyday comfort, the layout features elegant formal living and dining rooms bathed in natural light. At the heart of the home is the chef's kitchen with chic creamy-white cabinetry, timeless soapstone countertops, premium appliances, and a generous center island. It opens directly to an inviting family room anchored by a cozy fireplace and sunny bay-window seating and to a charming screened porch. The highly desirable main-level primary suite serves as a peaceful retreat, featuring a lavish en-suite spa-inspired bath designed for pure relaxation. Upstairs, you will discover three generously proportioned bedrooms, a stylishly updated full bath, and an expansive bonus room illuminated by bright skylights-a versatile space ready to become your home office, private gym, media lounge, or playroom. Peace of mind comes built-in with extensive improvements, including fresh exterior paint (2023), a comprehensive kitchen renovation (2021), a new roof (2015), updated interior painting (2015-2021-2026), and a stylishly renovated hall bath(2022). A truly ideal blend of classic architectural charm, modern luxury, and scenic country privacy. A win-win!

77 Wayside Ln, Redding

$1,099,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24209017 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

$649,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24149260 MLS

NEW AGRESSIVE PRICE! 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 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 two story 2-car garage. Upstairs is the grand primary bedroom with 3 closets and a 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 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 including NEW ROOF 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 (7th in the order)

268 Umpawaug Rd, Redding

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Umpawaug Homes under $1.25 million

Newest Umpawaug Homes under $1.25 million

How much is your home worth?

How much is your home worth?