Watertown Real Estate

Welcome to Watertown, a charming town located in Litchfield County, Connecticut. Watertown is a picturesque New England town known for its historic charm, beautiful landscapes, and strong sense of community.

With its convenient location in the heart of Litchfield County, Watertown offers residents the perfect balance of small-town charm and modern amenities. The town is surrounded by lush greenery, rolling hills, and scenic views, making it a peaceful and idyllic place to call home.

Watertown boasts a rich history dating back to the 17th century, with many historic buildings and landmarks still standing today. Residents can explore the town's historic sites, museums, and cultural attractions to learn more about its fascinating past.

In addition to its historical significance, Watertown offers a variety of recreational activities for residents to enjoy. From hiking and biking trails to parks and outdoor spaces, there are plenty of opportunities to stay active and connect with nature.

Watertown is also home to a vibrant community with a strong sense of camaraderie. Residents can participate in local events, festivals, and community gatherings throughout the year, fostering a warm and welcoming atmosphere for all who call Watertown home.

Whether you're drawn to Watertown for its history, natural beauty, or sense of community, this charming town has something to offer everyone. Come discover the magic of Watertown and find your perfect place to call home in Litchfield County, Connecticut.

Newest Listings in Watertown

$359,000

3 Beds ⋅ 3 Baths ⋅ 24197215 MLS ⋅ Artillery Hill BLDG.

Three-bedroom condominiums are a rare find in Watertown, and this spacious end-unit townhouse at Artillery Hill offers an exceptional combination of space, flexibility, and low-maintenance living. With more than 1,500 square feet, 2.5 baths, an attached garage, central air, and a full basement, the home provides many of the features of a single-family residence with the convenience of condominium ownership. The main level features an updated kitchen with white cabinetry, stainless steel appliances, a Carrera-style backsplash, and pantry storage. The adjoining dining area opens to a private deck, while the comfortable living room is anchored by a wood-burning fireplace. Two generously sized bedrooms and an updated full bath with a walk-in shower offer the possibility of convenient main-level living. Upstairs, a private bedroom suite with a full bath and walk-in closet creates an ideal primary retreat, guest suite, or dedicated home office. A skylight above the staircase fills the interior with natural light, and laundry hookups are available on the main level. The expansive unfinished basement offers excellent storage and direct access to the attached one-car garage. Additional guest parking is conveniently located across from the unit, and Artillery Hill residents enjoy access to the community's in-ground pool.

20 Cannon Ridge Dr Unit 20, Watertown

$499,900

3 Beds ⋅ 2 Baths ⋅ 24184918 MLS

Located in a well-established Watertown neighborhood just moments from Smith Pond, this well-maintained 3-bedroom, 2-bath Raised Ranch offers a great combination of space, updates, and convenience. Set on a beautiful 1-acre lot, the property provides plenty of outdoor space while remaining close to shopping, dining, parks, major commuter routes, and the Watertown school district. Inside, you'll find hardwood floors throughout the main level, a versatile floor plan, and a partially finished lower level that's ideal for a family room, home office, or recreation space. The all-season sunroom adds valuable living space and provides easy access to the fully fenced backyard, perfect for entertaining, pets, gardening, or play. Recent improvements include a brand-new furnace and central A/C system, new refrigerator and gas range, and newer windows with a transferable warranty. A whole-house generator offers added peace of mind. Whether you're a first-time buyer, looking for more space, or searching for a home in an established neighborhood, this property offers an excellent opportunity to make it your own. With its spacious lot, thoughtful updates, and convenient location, it's ready for its next chapter.

379 Smith Pond Rd, Watertown

$339,000

3 Beds ⋅ 1 Baths ⋅ 24195402 MLS

Welcome to this beautifully renovated 3-bedroom home, perfectly situated on a spacious, level lot overlooking attractive Brooke views. Completely updated from top to bottom, this move-in ready property offers modern finishes and effortless living. The bright, inviting kitchen features stainless steel appliances, stylish cabinetry, and plenty of workspace for everyday cooking and entertaining. Outside, you'll find a large, flat backyard with a fire pit, creating the perfect setting for relaxing evenings, gatherings with friends, or enjoying the outdoors. With nothing left to do but unpack, this home is an excellent opportunity for first-time buyers, downsizers, or anyone looking for a turnkey property. MOVE QUICK!

48 Rockdale Ave, Watertown

$289,999

3 Beds ⋅ 1 Baths ⋅ 24188604 MLS

Welcome home to this well maintained 3 bedroom, 1 bathroom ranch located in a quiet Oakville neighborhood! Offering comfortable one-level living, this home features a beautifully renovated full size bathroom & hardwood flooring in the living room and two of the three bedrooms. The eat in kitchen offers a sliding glass door that leads to a spacious , fully fenced backyard- perfect for entertaining, outdoor gatherings, gardening, or simply relaxing. Stay cool during the summer months with the convenience of a mini-split air conditioning system. Additional highlights include an attached one car garage, an additional parking pad for extra convenience, an approximately 8 yr old roof equipped with solar panels, and a pellet stove in the basement that serves as an excellent supplemental heat source. Whether you're a first time homebuyer, looking to downsize, or searching for a home that's been lovingly cared for, this charming ranch offers the perfect blend of comfort, functionality, and value. **The seller has received multiple offers and is calling for HIGHEST AND BEST OFFERS DUE BY SATURDAY 8/1 AT 8PM. **

51 Turner Ave, Watertown

$495,000

3 Baths ⋅ 24194650 MLS

mixed-use investment opportunity! This income-producing property features a two-family residence with a commercial retail storefront, offering outstanding versatility for investors or owner-occupants. The residential portion offers a total of 2,012 square feet. The first-floor apartment features 2 bedrooms and includes a washer, dryer, refrigerator, range and dishwasher. The second-floor apartment offers 3 bedrooms and includes a refrigerator, range, washer and dryer. Both units provide spacious layouts and strong rental potential. The commercial space consists of approximately 1,660 square feet and is currently operating as a successful restaurant, providing an established retail presence with excellent visibility and additional income potential. Whether you're looking to expand your investment portfolio or occupy one of the units while generating rental income, this unique property offers multiple income streams and endless possibilities. Conveniently located near shopping, restaurants, schools, and major highways, this is a rare opportunity to own a versatile mixed-use property with both residential and commercial appeal.

202 Main St, Watertown

$369,900

3 Beds ⋅ 2 Baths ⋅ 24194409 MLS

Highest & Best offer deadline is TONIGHT, Sunday (8/2), at 8:00 PM. 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

$995,000

4 Beds ⋅ 3 Baths ⋅ 24192726 MLS

Coming Soon! Exceptional New Construction on 6.59 private acres in Watertown with breathtaking views and a setting that's perfect for horse enthusiasts, car collectors, or anyone seeking the ultimate country retreat. This stunning 3 or 4 bedroom, 3 full bath home offers a bright, open floor plan with soaring vaulted ceilings, gorgeous hardwood floors throughout, and a spacious bonus room over the garage. Designed with today's lifestyle in mind, the finished walk-out lower level with a full bath provides exceptional flexibility and presents an outstanding opportunity for multigenerational living. With only minimal modifications, this space could easily accommodate an in-law suite, guest quarters, or a private living area, making it ideal for extended family or long-term visitors. The primary suite features direct access to an expansive deck overlooking the picturesque property, with additional deck access from the family room, creating the perfect setting for relaxing or entertaining while taking in the spectacular views. At the rear of the property sits an impressive 24' x 48' two-story post-and-beam barn, with an approximate replacement value of $250K. Whether you're an equestrian looking for exceptional horse facilities or car enthusiast this remarkable barn is a true showpiece. Offering the perfect blend of privacy, and versatility, this rare new construction combines modern design with endless possibilities.Coming to the market next week. Available by appointment only.

191 Northfield Rd, Watertown

$429,999

3 Beds ⋅ 3 Baths ⋅ 24193923 MLS

***HIGHEST & BEST DEADLINE MONDAY 9PM 7/27/26*** THE ONE THAT IS ALREADY DONE. Most homes arrive with a punch list. This one arrives finished. Rebuilt from top to bottom through eight years of meticulous ownership, 332 Williamson Circle is the turnkey raised ranch Oakville rarely sees. The open main level is anchored by a fully remodeled kitchen with white cabinetry, center island, and stainless appliances, flowing into bright living and dining space over hardwood floors that run throughout. Every bathroom has been tastefully renovated and a wood burning fireplace warms the heart of the home. The finished walkout lower level flexes as family room, office, or gym, with a laundry closet and direct access to the yard and side entry two car garage. The systems tell the same story. Owned rooftop solar installed in 2021 transfers with no lease to assume and pairs with ductless heating and cooling added in 2024 to keep utility costs remarkably low. A new electrical panel with professional rewiring in 2018, a roof about four years young, Andersen windows throughout, and city water and sewer complete the picture. Outside, a three season sunroom overlooks a covered patio at the walkout, while a custom retaining wall patio turns a sloped corner of the yard into a private outdoor patio framed by garden beds and a newer shed. Level lot on a quiet Oakville street, minutes to Route 8 and Main Street shops, restaurants, schools, and parks.

332 Williamson Cir, 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

$89,900

24193739 MLS

Prime 2.75 acre lot in Oakville. Perfect for your dream home! Discover this incredible opportunity to own a spacious 2.75-acre lot in the desirable Oakville neighborhood of Watertown, Connecticut. Nestled on a peaceful dead-end street, this property offers ultimate privacy and tranquility, making it the perfect setting to build your dream home or create a stunning compound. Whether you're envisioning a sprawling estate, a modern retreat, or a personal sanctuary, this expansive lot gives you the flexibility to design and customize every detail. Surrounded by nature yet conveniently close to local amenities, schools, and major roadways, this is the ideal location for those seeking both serenity and accessibility. Buyer are to do their own due diligence.

Old Colonial Rd, Watertown

$195,000

24191411 MLS

Prime Main Street Location in the heart of Watertown! This highly visible property offers exceptional exposure with a high daily traffic count, sidewalks leading directly to the downtown business district, and Starbucks as a neighboring business, making it an ideal location for a variety of commercial opportunities. Located in Watertown's Business Central (BC) Zone, the property offers a wide range of potential uses, including retail stores, professional offices, medical and financial offices, restaurants, cafes, bakeries, personal service businesses such as salons, barber shops, spas, and fitness studios, as well as mixed-use development with commercial space on the first floor and residential apartments above. The BC District is designed to promote a vibrant downtown environment. All applications subject to applicable Town approvals. Buyers are encouraged to verify all permitted uses and zoning requirements with the Town of Watertown Planning & Zoning Department for their specific intended use.

854 Main St, Watertown

$369,900

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

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