Taft School Real Estate

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

70 Eastwood Hall Rd, Watertown
$615,000
3 Beds ⋅ 3 Baths ⋅ 24216854 MLS
Located in Watertown's desirable Taft area with views of Watertown Golf Club, this 3 bedroom, 2.5 bath Colonial offers light filled spaces and modern updates throughout. MAJOR UPDATES in the last 5 years include: Roof, Siding, Windows, Furnace, Central Air and Solar Panels. Enjoy hardwood floors, a remodeled kitchen with granite counters, stainless steel appliances, beverage bar and custom pantry with butcher block top. The family room features vaulted ceilings, a fireplace and double doors leading to a newly installed deck-perfect for indoor/outdoor entertaining. Completing the main floor is a dining room with large picture window offering views of the private yard and a formal living area. This space offers flexibility for your growing needs! Upstairs, you have 3 nicely sized bedrooms, a full bath and laundry for convenience. A remodeled primary suite features a walk in closet and private bath. Move right in and enjoy the perfect blend of modern updates, outdoor living and room to entertain in Watertown's sought after Taft area!

70 Eastwood Hall Rd, Watertown
815 Cheyenne Rd, Watertown
$189,900
2 Beds ⋅ 1 Baths ⋅ 24214341 MLS
A little cottage with big potential! Just a short walk to the water at Lake Winnemaug, this one-bedroom, one-bath home offers a peaceful setting with a private yard and nature all around. A full basement with walkout access provides convenient storage and room for your ideas. Bring your vision and personal touches to create a cozy private home, weekend getaway, or potential investment property. Explore the possibilities for an Airbnb or vacation rental. A wonderful opportunity for buyers looking to build value and enjoy life near the lake! Property is being sold as is; cash offers preferred.

815 Cheyenne Rd, Watertown
104 Northwest Dr, Watertown
$615,000
4 Beds ⋅ 3 Baths ⋅ 24211413 MLS
Custom Craftsmanship, Unparalleled Curbside Appeal, and Pride of ownership to a Majestic Magnitude on full display with this 4 Bedroom 2.5 Bath, 2800sf+ Watertown Colonial. A master class in skilled carpentry abounds immediately upon entry into this open concept, hardwood laden main level living space. The Living room adorns built ins, recessed lighting, and a wood burning masonry fireplace tastefully encased w/ ornate woodwork. Eat-In Kitchen w/ island is equipped with stainless steel appliances, beaming granite countertops, tile flooring and offers slider access to the freshly revitalized Trex decking guiding owners to the lush emerald, green rear grounds, bursting with leisurely potential. The sundrenched formal dining room features bay windows and crown molding. A cavernous family room w/ cathedral ceiling and split system rounds out the main level living space. Upper level features a Capacious primary bedroom suite w/ recently remodeled full bath. Each of the additional 3 spacious bedrooms has ample closet space, plush carpeting and ceiling fans. Brand new, finished lower level w/ walkout adorns engineered wood flooring and a delightful addition of 550+ sf to enjoy. Precision, focus and skillful detail noted upon Every nook of this spectacular home. A highly advantageous solar program, thorough updating, soothing earth tone vibes and a desirable neighborhood further distinguish this estate from all its peers. The time is Now to Capture this Captivating Watertown Jewel.

104 Northwest Dr, Watertown
96 Neill Dr, Watertown
$599,900
5 Beds ⋅ 4 Baths ⋅ 24208411 MLS
WELCOME to 96 Neill Drive this Beautifully remodeled Colonial with Finished basement, located in one of the area's most sought-after neighborhoods! This home features 5 SPACIOUS bedrooms and 3.5 updated bathrooms with stylish tile flooring. You'll love the open-concept layout that includes a bright family room, an eat-in kitchen with custom solid-wood cabinets, Corian countertops, and a center island - Perfect for Entertaining. The formal dining room opens seamlessly into a large living room, ideal for gatherings. Additional highlights include GLEAMING HARDWOOD FLOORS THROUGHOUT Central air and Central vacuum, Fireplace in the living area French doors leading to a Covered wood deck overlooking a private backyard. Convenient mudroom/laundry room off the garage Remodeled bathrooms with modern finishes The Finished Basement fully remodeled and features its own private entrance (walkout basement), open floor plan, 1 bedroom, and a full bath - perfect for extended family or guests. Located close to the Prestigious Taft School and Watertown Golf Club Whether you're looking for multigenerational living or simply a spacious and updated home in a desirable location, this property has it all. Schedule your private showing today!

96 Neill Dr, Watertown
368 Hamilton Ave, Watertown
$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
101 Cannon Ridge Dr Unit 101, Watertown
$379,999
3 Beds ⋅ 2 Baths ⋅ 24201695 MLS ⋅ Artillery Hill BLDG.
BACK ON MARKET, BUYER UNABLE TO PERFORM. 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. Turn-key, meticulously maintained, and full of upgrades.

101 Cannon Ridge Dr Unit 101, Watertown
47 Academy Hl, Watertown
$849,900
6 Beds ⋅ 7 Baths ⋅ 24192575 MLS
The Mary A. Merriman Residence, circa 1871, is one of Watertown's most distinctive historic homes, combining exceptional architectural significance with timeless craftsmanship and modern comfort. Listed on the National Register of Historic Places and just a five-minute walk from The Taft School, this remarkable Victorian-era residence was originally part of the Heminway family estate. Beautifully preserved period details include soaring ceilings, intricate millwork, custom built-ins, floor-to-ceiling windows, multiple fireplaces, original lighting, and a striking butterfly staircase. A spectacular 60-foot mahogany-covered porch sets the tone for the gracious interiors beyond. Generous living spaces include formal dining and living rooms, a great room, library, sunroom, and updated kitchen with an expansive butler's pantry. Several en suite bedrooms offer flexibility, while the impressive primary suite includes multiple private rooms and its own balcony. Outside, mature grounds, a stone patio, original greenhouse, and an in-ground pool create a private setting for entertaining and relaxation. Carefully maintained for generations, this is a rare opportunity to own a truly extraordinary piece of Watertown history.

47 Academy Hl, Watertown
190 Charter Oak Dr, Watertown
$695,000
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
87 Woodruff Ave, 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
319 Thomaston Rd Unit 13, 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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