Taft School Real Estate

Welcome to the charming neighborhood surrounding Taft School in Watertown, Connecticut—a hidden gem nestled in Litchfield County. This picturesque area is characterized by its rich history, vibrant community spirit, and stunning natural landscapes, making it an ideal place to call home.

Taft School, a prestigious private institution founded in 1890, serves as the cornerstone of the neighborhood, attracting families who value education and a close-knit community. The school’s beautiful campus, with its historic architecture and sprawling green lawns, creates a serene backdrop that enhances the overall appeal of the area. Residents often enjoy leisurely strolls around the campus, soaking in the beauty of the surroundings.

The neighborhood around Taft School boasts a delightful mix of charming homes, from classic New England colonials to modern residences, each with its own unique character. Tree-lined streets invite families to explore the outdoors, while nearby parks and recreational areas provide ample opportunities for hiking, biking, and enjoying nature.

Watertown itself is known for its friendly atmosphere and a variety of local shops, restaurants, and cafes. Residents can indulge in the delectable offerings of local eateries or take advantage of the vibrant farmers' market, showcasing the best produce and artisanal goods from the region.

With its strong sense of community, excellent schools, and scenic beauty, the Taft School neighborhood is more than just a place to live; it’s a lifestyle. If you’re looking for a welcoming environment that combines educational excellence with the charm of small-town living, this area is the perfect choice for you and your family. Come discover the warmth and beauty of Watertown today!

Newest Listings in Taft School

$369,900

3 Beds ⋅ 2 Baths ⋅ 24194409 MLS

PRIME WATERTOWN LOCATION ON ALMOST 1 ACRE! Nestled on a private 0.90 acre lot right down the street from Veterans Memorial Park, this 3 bedroom, 1.5 bath Ranch offers a functional layout and unbeatable local convenience. Step inside to a sun drenched living room anchored by a large bay window and gleaming hardwood floors that extend throughout the main level. The heart of the home features a spacious eat in kitchen complete with warm cherry cabinetry, tiled flooring, recessed lighting, and newer stainless steel appliances. Sliders off the kitchen lead directly to an expansive Trex deck overlooking a peaceful backyard, perfect for outdoor entertaining. The main level offers 3 comfortable bedrooms with hardwood floors, including a primary suite with a private half bath, plus a full hall bathroom. Downstairs, the finished walk out lower level delivers versatile bonus space for a family room, home office, or gym, along with a dedicated laundry area, tiled floors, direct access to the attached 2 car garage, and a door leading out to a covered patio. Unmatched Location: Walk to Veterans Memorial Park for sports fields, pavilion, and playground. Enjoy quick access to Crestbrook Park and Golf Course, local schools, shopping, and major routes. Endless potential in a top tier neighborhood!

532 Nova Scotia Hill Rd, Watertown

$575,000

4 Beds ⋅ 3 Baths ⋅ 24193664 MLS

**Much larger than it appears!** Offering 2,512 square feet of living space, this beautifully updated Cape blends timeless New England charm with the spacious layout today's buyers are searching for. Nestled on 267 North Street, this home offers exceptional curb appeal with professionally designed paver walkways, attractive stonework, and beautifully landscaped grounds. Step inside and prepare to be surprised. The expansive main level is the true centerpiece, featuring a desirable primary suite, a second main-level bedroom perfect as a nursery, guest room or home office, and inviting living spaces designed for both everyday comfort and entertaining. Rich hardwood flooring, abundant natural light, recessed lighting, and a gas fireplace create a warm, welcoming atmosphere throughout. The stunning kitchen is truly the heart of the home, showcasing white cabinetry, stainless steel appliances, elegant stone countertops, and an oversized center island with generous seating. The spacious dining area and multiple oversized French doors create an effortless flow between indoor and outdoor living.

267 North St, Watertown

$899,900

6 Beds ⋅ 7 Baths ⋅ 24192575 MLS

Welcome to 47 Academy Hill, a stately Victorian-era Colonial where timeless craftsmanship meets modern comfort in the heart of Watertown. Offering more than 3,700 square feet of beautifully maintained living space, this exceptional home is just a five-minute walk from The Taft School and minutes from downtown shops, restaurants, and amenities. A gracious wraparound porch creates an impressive first impression and sets the tone for the remarkable period details found throughout. Inside, soaring 10-foot ceilings, extensive moldings, custom built-ins, and generously proportioned rooms reflect a level of craftsmanship that would be extraordinarily difficult to reproduce in today's building climate. The versatile layout includes several en suite bedrooms and baths, providing excellent flexibility for family, guests, or multigenerational living. A bright sun porch overlooks the private backyard and in-ground pool, creating a beautiful space to relax and enjoy the changing seasons. The pool area offers a peaceful setting for summer entertaining and everyday enjoyment. Rich in character and filled with irreplaceable architectural details, this distinctive home presents a rare opportunity to own one of Watertown's truly special properties.

47 Academy Hl, Watertown

$399,900

3 Beds ⋅ 2 Baths ⋅ 24191323 MLS

Welcome to 161 Chestnut Grove Road, where timeless charm meets everyday comfort. Nestled on a peaceful half acre lot, this inviting 3/bed, 2/bath bungalow offers over 1500 sq/ft. of living space filled with character and natural light. The spacious dining room features a classic built-in hutch and flows into the living room, complete with French doors leading to a generous deck overlooking the private backyard and established gardens. The flexible floor plan includes a first-floor primary bedroom and full bath, while two bedrooms and a second full bath are located upstairs. Outside, enjoy a partially fenced year, patio and a detached 2-car garage with an attach workshop-ideal for hobbies, storage or additional workspace. Conveniently located just minutes from Watertown's town center, schools, shopping, parks and commuter routes, this home offers the perfect blend of privacy, charm and accessibility.

161 Chestnut Grove Rd, Watertown

$459,900

3 Beds ⋅ 2 Baths ⋅ 24190619 MLS

This updated, well maintained home, located on a quiet cul de sac, with a fenced in yard is now ready for new owners. The main level features a kitchen/dining room that flows to the living room. The large living room features a gas fireplace, wood floor and bay window. The sliders off the dining area lead to an expansive deck with gazebo. Three bedrooms and a full bath complete this level. The lower level is a large family room with gas fireplace, wet bar, a full bath and sliders to the patio. Many possibilities for additional living space. The fenced in backyard is ideal for gardening, entertaining and relaxing. There is a storage shed in the back yard as well.

15 Fieldwood Dr, Watertown

$725,000

4 Beds ⋅ 4 Baths ⋅ 24186419 MLS

Hard to find 1st floor 3 room in-law setup in this 9 room custom built brick split level home on a private and level 1.38 acre lot in a quiet Guernseytown subdivision minutes from town and hand-crafted in 1985 by a builder who intended it to outlast other homes. There is a total of 4 bedrooms and 4 full bathrooms in this unique European style multi level home with an attached 2 car oversize garage, a covered front porch with a balcony above off the 2nd floor and a fabulous rear covered patio all done with a level of architectural detail and craftsmanship that the current market simply does not produce. The main level is organized for real life; a living room with a fireplace, a large dining room with a slider to the patio, a full bathroom, and an eat-in kitchen generous in every dimension with loads of cabinets and counter space & GE Profile appliances. The upper level has 3 good size bedrooms and 2 full bathrooms, one with a steam shower. The ground level 3 room in-law is a proper, fully realized suite - built into the home from the beginning, designed to be lived in with dignity and independence with a full kitchen with appliances and garage access. There is a full basement under the main house for plenty of storage area with an unheated finished rec room. Other amenities include underground utilities, 2 split air conditioning units, an automatic Generac generator, a Vigilant cast-iron stove in the foyer, custom brick work making this an inviting and carefree residence.

190 Charter Oak Dr, Watertown

$399,000

3 Beds ⋅ 2 Baths ⋅ 24185455 MLS

Step into a piece of Watertown's rich history at 52 Wheeler Street, a residence brimming with antique character and timeless appeal. This home offers a rare blend of preserved original details and essential modern updates. Situated on a quiet, level lot just one block from the prestigious Taft School, the property welcomes you with a classic wraparound porch, featuring a screened-in section perfect for tranquil summer evenings. The interior reflects the craftsmanship of a bygone era, anchored by a cozy fireplace and a formal dining room. The layout is both functional and inviting, highlighted by a charming step-down eat-in kitchen and a convenient main-level full bath with integrated laundry. Upstairs, three spacious bedrooms surround a versatile flex space, ideal for a home office or playroom, while a second full bath completes the level. Beyond its historic beauty, the home boasts significant practical improvements for total peace of mind, including a new roof (2022), a newer boiler, and a one-year-old water heater. Abundant storage space-a rare find for a home of this age-is supplemented by a newer outdoor shed and off-street parking. This distinctive property presents a rare opportunity to own a storied historic home in one of Watertown's most desirable neighborhoods.

52 Wheeler St, Watertown

$399,500

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 two 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

$399,900

4 Beds ⋅ 3 Baths ⋅ 24172397 MLS

Back on the Market - No Fault of the Property. Welcome home to this beautifully maintained 4-bedroom, 3-bath property offering spacious living areas and a versatile layout. The Partial finished basement includes a full bathroom and provides additional flexibility for storage, recreation, a home office, or other personal needs. Enjoy comfortable bedrooms, ample storage, and a home designed for both everyday living and entertaining. Conveniently located near local amenities, schools, and major routes. Outside, you'll find a nicely sized backyard with plenty of room for outdoor gatherings, gardening, or simply relaxing, along with ample parking to accommodate multiple vehicles. Schedule your private showing today and come see everything this wonderful home has to offer!

93 Main St, Watertown

$750,000

4 Beds ⋅ 4 Baths ⋅ 24159719 MLS

Custom-built in 2015, this 3,900 sq ft property combines modern comfort with timeless heritage. The 3,200 sq ft main residence features 3 bedrooms, a private office (or 4th bedroom), and an open-concept layout that flows from a custom kitchen-complete with a brick backsplash, live-edge island, and coffee bar-into a cathedral family room with a granite-hearth fireplace. A standout feature is the 750 sq ft attached in-law/au pair apartment, offering a private kitchen, living area, bedroom, full bath, laundry, and optional chair lift access-ideal for multigenerational living, guest quarters, or rental income. This home blends reclaimed wood beams and granite from the original family farmhouse with modern amenities. The primary suite, private study, mudroom, and laundry complete the main level, while upstairs, two oversized bedrooms and an open balcony overlook the central gathering space. Efficiency features include central air, central vac, a multi-fuel furnace (coal/wood/propane), two high-efficiency propane tankless water heaters, and a heated two-car garage. Nestled between Tara Farm and Careyshire Farm, and less than a mile from Taft School and Hawk Ridge Winery, the location offers privacy with easy access to Route 6, Woodbury, Watertown Center shopping, dining, and commuter routes. Enjoy nearby hiking trails to Nonnewaug Falls, as well as snowmobiling and quad trails for an enhanced outdoor lifestyle.

195 Hinman Rd, Watertown

$325,000

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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