Taft School Real Estate

Taft School Real Estate

Welcome to Taft School, a prestigious and vibrant neighborhood nestled in the heart of Watertown, Connecticut. Known for its rich history and academic excellence, Taft School is more than just a renowned private preparatory school; it's a community that embodies the spirit of learning and growth.

Surrounded by the picturesque landscapes of Litchfield County, Taft School offers a serene and inviting atmosphere, perfect for families and individuals alike. The neighborhood is characterized by its charming tree-lined streets, historic architecture, and well-maintained green spaces, creating a welcoming environment that residents take great pride in.

Within walking distance, you’ll find an array of amenities, including quaint cafes, local boutiques, and vibrant parks that invite outdoor activities and community gatherings. The nearby Watertown Plaza provides convenient shopping and dining options, ensuring that everything you need is just a stone’s throw away.

Education is at the forefront of this community, with Taft School itself offering a rigorous academic curriculum and a plethora of extracurricular activities that cater to a diverse range of interests. The school’s commitment to fostering a nurturing and inclusive environment makes it a cornerstone of the neighborhood.

For those who appreciate the balance of a close-knit community with access to larger urban centers, Taft School is ideally situated. Just a short drive from Waterbury and other nearby towns, residents enjoy the tranquility of suburban life while remaining connected to the vibrant culture and opportunities of Connecticut.

Experience the charm and allure of Taft School, where education, community, and natural beauty come together to create an extraordinary place to call home.

Newest Listings in Taft School

70 Eastwood Hall Rd, Watertown
$615,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
96 Neill Dr, Watertown
$599,900
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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
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