Taft School Homes under $400,000

Welcome to the charming neighborhood of Taft School in Watertown, Connecticut, where history and community spirit blend seamlessly to create an inviting atmosphere. Nestled in Litchfield County, this area is renowned for its picturesque landscapes and rich educational heritage, thanks to the prestigious Taft School, one of the country’s leading preparatory institutions.

As you stroll through the tree-lined streets, you’ll find a delightful mix of architectural styles, from classic New England colonials to cozy bungalows. The neighborhood boasts a variety of homes priced under $400,000, making it an attractive option for first-time buyers, families, and those looking to downsize. These homes often feature spacious yards, perfect for outdoor gatherings or simply enjoying the serene surroundings.

Living in Taft School means more than just a beautiful home; it offers a vibrant community with access to excellent schools, parks, and recreational facilities. The nearby Watertown Town Park and the scenic Lake Quassapaug provide ample opportunities for outdoor activities, from hiking and biking to fishing and picnicking.

Residents enjoy a close-knit community feel, with local shops, cafes, and restaurants just a stone's throw away. The area is also conveniently located near major highways, providing easy access to larger cities like Waterbury and Hartford for those commuting for work or leisure.

In Taft School, you’ll find not just a house, but a place to call home, where community and comfort come together in a picturesque setting. Explore the possibilities today!

Newest Taft School Homes under $400,000

$365,000

3 Beds ⋅ 2 Baths ⋅ 24199743 MLS

Set in the highly sought-after Taft area, this 3-bedroom, 2-bath Cape offers a spacious 1.97-acre setting with calm stream & large lawn space, classic character, and plenty of opportunity. The park-like yard, small stream, fruit trees, and garden areas create a peaceful backdrop, while the location puts you close to amenities, downtown Watertown, and the Watertown Country Club. Inside, the home offers 1,238 square feet with a refreshed eat-in kitchen featuring granite counters and hardwood floors, a comfortable living room and dining room, and convenient main-level laundry room. The enclosed front porch adds additional flexible relaxation space and could easily become a favorite gathering spot or cozy retreat. Upstairs, the primary bedroom has direct access to it's deck, along with two additional bedrooms and a full bath. The outdoor spaces offer even more to enjoy, including the 2 decks, shed, an outdoor shower, and unique steam room heated by a wood stove which can be refreshed and utilized, or simply used as an extra space for storage. An attached over-sized garage provides valuable room and convenience. The home has had the major cost items done such as the roof & water system, plus a regularly-serviced mechanical system. With its desirable location, generous lot size, and unique features, this property offers a wonderful opportunity to create a home that truly reflects you! Come check it out!

368 Hamilton Ave, Watertown

$399,000

3 Beds ⋅ 2 Baths ⋅ 24204811 MLS

Cute as a button, this expanded Cape is conveniently located near Taft School and within walking distance to downtown Watertown. Hardwood floors run throughout much of the home, where the first floor offers a spacious living room with a pellet stove, dining room, kitchen, and full bath. Just off the kitchen, the sunken family room is a welcome addition, featuring a propane fireplace flanked by built-ins and access to the back deck. Upstairs, the primary suite offers an updated bathroom and generous closet space, along with two additional bedrooms, including one with built-ins. Outside, enjoy the large back deck, a level yard with room to play, and a one-car under-house garage. A charming home in a convenient Watertown location!

286 North St, Watertown

$379,999

3 Beds ⋅ 2 Baths ⋅ 24201695 MLS ⋅ Artillery Hill BLDG.

Welcome to your dream home! This lovely, rarely available ranch-style condo in Watertown, Connecticut, offers the perfect blend of elegant architectural details and modern, worry-free upgrades. From the moment you step inside, you will love the sophisticated craftsmanship, featuring vaulted and coffered ceilings, classic chair rails, and elegant picture frame molding that add timeless character to the space. The heart of the home is a spacious, open-concept kitchen designed for effortless entertaining and daily living. Upgraded for maximum peace of mind, the kitchen features a brand-new dishwasher, stove, microwave and garbage disposal (all new in 2026), along with select newly replaced windows that bring in beautiful natural light. This single-level floor plan offers 3 bedrooms & 2 bathrooms, including a comfortable primary suite. Major mechanical updates have already been taken care for you, including a new furnace and central air system installed in Feb, 2025. Need more space? The massive walkout finished basement provides incredible potential. Framed and ready for your personal touch; all it needs is your choice of flooring to become the ultimate rec room, home office or gym. Perfectly situated within a lovely, highly desirable community, this unit is just steps away from the community pool and tennis courts. Enjoy the convenience of being local to excellent shopping, dining and daily amenities. Turn-key, meticulously maintained, and full of upgrades.

101 Cannon Ridge Dr Unit 101, Watertown

$345,900

4 Beds ⋅ 2 Baths ⋅ 24184144 MLS

Welcome home to this beautiful two-family property located in the heart of Watertown. Sitting on a spacious .66 acre lot, this home offers a perfect blend of comfort, space, and convenience. The first floor features three bedrooms, a full bathroom, a bright living room, a formal dining room, and a well-appointed kitchen-ideal for everyday living or entertaining. Upstairs, the second unit offers three bedrooms, a full bathroom, a cozy living room, a dining area, and a functional kitchen with a walk-in pantry, providing a great layout for extended family or rental income potential. Located just a short walk from Watertown's vibrant downtown, you'll enjoy easy access to local shops, restaurants, parks, and public transportation. Whether you're looking for an investment opportunity or a place to call home, this property has it all.

87 Woodruff Ave, Watertown

$305,000

2 Beds ⋅ 3 Baths ⋅ 24158069 MLS ⋅ Watertown Old Farms BLDG.

Desirable Watertown Old Farms townhome offering open-concept living, custom stone, natural gas fireplace with built-in shelving, granite kitchen, and a private deck overlooking serene wooded surroundings. The bright living and dining area features warm wood-style flooring, a natural gas fireplace framed by custom stonework and flanked by built-in bookshelves, and a sliding door that leads to a private deck with a retractable awning-perfect for relaxing while enjoying the wooded backdrop. The kitchen includes granite countertops, warm wood cabinetry, tile backsplash, stainless steel refrigerator and stove, and a convenient pass-through to the living and dining area that keeps the space open and connected. The main level also features a powder room with washer/dryer hookups. Upstairs you'll find two generously sized bedrooms with ample closet space, each with its own full bathroom for added comfort and privacy. The home also includes a partially finished lower level offering versatile bonus space along with plenty of storage. Additional highlights include a one-car garage and a short, convenient walk from the parking area to your front door. Ideally located just minutes from two town centers, Route 8, and everything Litchfield County has to offer.

319 Thomaston Rd Unit 13, Watertown

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