Refine Search
Map
Sort by
$367,750
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
$350,000
3 Beds ⋅ 2 Baths ⋅ 24199759 MLS
Well-built Ranch offering single-level living at its best! Featuring 3 bedrooms with ceiling fans, a spacious living room with a beautiful floor-to-ceiling stone fireplace, and hardwood floors throughout the main level. Spacious eat-in kitchen offers ample cabinet space and a slider leading to the fully screened-in porch overlooking the private backyard. The full walk-out basement includes a family room, generous closet space, large storage room, half bath with laundry, and access to the attached 1-car garage. Updates within the last 5 years include newer central air, boiler, roof, replacement windows, and a newly installed air purification system for enhanced indoor air quality. Enjoy summer fun in the above-ground pool with deck, set in the tree-lined, level backyard. Conveniently located near schools, shopping, Route 63, Route 8, and Route 84. Schedule your showing today!

46 Jason Ave, Watertown
$350,000
4 Beds ⋅ 2 Baths ⋅ 24184049 MLS
This 4-bedroom, 1.5-bathroom single-family home is located at 34 Shelter Hill Ave, in the Oakville section of Watertown, in Litchfield County and was built in 1910. This home offers 1,314 square feet of living space with 7 total rooms and has been continually upgraded by the owner; however, they are no longer motivated to put more time into creating their vision (rendering included in photos). The home sits on a 0.65-acre level grass lot. It is served by municipal sewer, water and natural gas. There is an Invisible animal containment fence included and a storage shed. Great Bones, and some nice detail. Needs to be finished. This would be a good candidate for a renovation loan, 203K loan.

34 Shelter Hill Ave, Watertown
$345,000
3 Beds ⋅ 1 Baths ⋅ 24183305 MLS
Welcome to a classic Colonial brimming with character, warmth, and opportunity. Situated on a generous corner lot in one of Oakville's established neighborhoods, this inviting three-bedroom home offers timeless appeal and comfortable everyday living. Step inside to discover sun-filled living spaces accented by hardwood floors, original door hardware, and classic New England charm. The bright kitchen flows effortlessly into the home's main living area, creating a welcoming environment for both daily life and entertaining. Upstairs, three comfortable bedrooms provide flexibility for family, guests, or a home office. Outside, the private backyard with secret garden vibes that offers space to relax, garden, or enjoy outdoor gatherings, while the detached garage and full walk-out basement provide valuable storage and future potential. Whether you're a first-time homeowner, downsizing, or searching for a home with character and room to personalize, this property delivers exceptional value. Conveniently located near shopping, dining, schools, parks, and major commuter routes, 462 Davis Street combines small-town charm with everyday convenience. Walk to shops and restaurants! This is a wonderful opportunity to own a classic Oakville home and enjoy all that the Watertown community has to offer.

462 Davis St, Watertown
$325,000
3 Beds ⋅ 2 Baths ⋅ 24201416 MLS
Welcome to 68 Frances Street, a charming property offering versatile living space, comfortable amenities, and inviting outdoor areas. The main level features two bedrooms, a well-appointed kitchen with a center island, and a full bathroom. The upper level offers two additional rooms along with a second full bathroom, providing flexibility for bedrooms, office space, hobby areas, or other needs. Enjoy outdoor living on the deck with a gazebo overlooking the fenced-in backyard. A private driveway and detached garage provide convenient parking and storage. This property offers a great opportunity to make the space your own while enjoying all that it has to offer! Check it out today!

68 Frances St, Watertown
$325,000
2 Beds ⋅ 1 Baths ⋅ 24199900 MLS
Escape to this 2 bedroom knotty pine cottage/ranch nestled on 2.5 picturesque acres in one of the most desirable locations in Watertown. Let your design style run wild because all the BIG ticketed mechanicals have all been updated. All you need to focus on is creating a space that reflects your unique design style. UPDATES include: NEW SEPTIC System installed 2010, NEW Roof, (GAF Timberline shingle with 50yr warranty) installed in 2021. NEW Electrical Service 200 AMP installed in 2010, NEW Windows installed in 2010, NEW Siding installed in 2023, NEW Paved Driveway in 2106 and NEW Boiler in 2010.

39 Killorin Rd, Watertown
$325,000
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
$320,000
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
$319,900
2 Beds ⋅ 2 Baths ⋅ 24187800 MLS
Conveniently located in a fantastic commuter-friendly location with easy access to town, this well-maintained 2-bedroom, 2-full-bath home offers comfort, updates, and flexible living space throughout. The updated kitchen features granite countertops and flows into the main living areas with beautiful hardwood floors. The finished walk-up attic provides additional versatile space, perfect for a home office, playroom, or guest area. The finished lower level boasts a spacious rec room with a cozy fireplace, a full bath, and direct access to a private backyard-ideal for entertaining or relaxing. Major improvements include newer roof, windows, doors, driveway, and garage door, providing peace of mind for years to come. Additional features include city utilities and a 1-car detached garage. Whether you're commuting to work or looking for a move-in-ready home with extra living space, this property offers exceptional value in a convenient location. Don't miss this opportunity!

13 Roberts Ave, Watertown
$300,000
3 Beds ⋅ 2 Baths ⋅ 24190590 MLS
3 Bedroom Ranch with remodeled eat-in-kitchen, garage, and large fully finished basement! Eat-in-kitchen with stainless steel appliances and tile countertops. Living Room with hardwood parquet floors. 3 bedrooms with laminate faux wood floors. 1 and a half bathrooms. Lower level family room and additional room. Front and back deck. Home has a gas heater in the basement that owner used to heat the home. It also has electric baseboard heat. 200 amp electrical service. This is a great home! Town Card has 1.0 baths. Home has 1.1 baths.

98 Greenwood St, Watertown
$299,999
2 Beds ⋅ 1 Baths ⋅ 24172822 MLS
Welcome to this beautiful ranch style home in Oakville, offering a large open kitchen with granite countertops and an island, with plenty cabinet space and stainless steel appliance. Offering 3 comfortable bedrooms, living room with fireplace, detached 2 car garage with a loft area for office or playroom. A private yard surrounding the home perfect for outdoors activities and entertaining. Property has a shared driveway. Huge reduction on price, seller relocating.

251 Riverside St, Watertown
$299,500
4 Beds ⋅ 2 Baths ⋅ 24205469 MLS
Welcome to 282 Sunnyside Avenue a home filled with charm and character. This 4-bedroom, 1.5 bath home offers a flexible layout featuring a convenient first floor bedroom with an attached bath. Kitchen features a peninsula for extra counter space and an adorable breakfast nook. The large dining room with attached living room is warmed by a pellet stove creating a cozy gathering space. Upstairs are three bedrooms and a full bathroom with plenty of storage space. Outside the property truly shines with an oversized level yard complete with flowering plants, beautiful trees and an additional piece that was previously added to bring the total acreage to .84 acres. This provides plenty of room to garden, play, entertain, or simply enjoy the outdoors. Your covered front porch is a great spot for morning coffee. The detached two car garage adds valuable storage and parking space. This special home has so much to offer and is ready for its next chapter.

282 Sunnyside Ave, Watertown
$279,987
3 Beds ⋅ 1 Baths ⋅ 24168298 MLS
$279,999 When would you like to see it? 82 Porter Street, Watertown, CT 06795. 3-bedroom, 1-bath single-family home built in 1919. Nestled on a generous 0.52-acre level lot. Sold twice at $300,000. Full inspection report available. Asbetos removed, oil tank removed and radon system being installed before close.

82 Porter St, Watertown
$279,900
4 Beds ⋅ 1 Baths ⋅ 24199317 MLS
Rich in history, this enchanting 1869 Colonial welcomes you with its traditional architecture and classic layout. The main floor boasts distinct living spaces, including a warm living room, a gracious dining room, and an intimate den that invites relaxation. Four generously sized bedrooms offer ample space for family or guests. Outside, a standalone detached garage adds functionality while preserving the property's historic aesthetic.Estate being sold "As Is"

54 Litchfield Rd, Watertown
$265,000
2 Beds ⋅ 2 Baths ⋅ 24199585 MLS
A Painstakingly Preserved, Serene, 2 Bedroom, 940SF+ Capacious Cape Oozing with potential in the Heart of Oakville. This timeless abode is Beaming with Period Era Custom Craftsmanship, perfectly balanced with functional comforts. The open concept, main level, boasts warm original wood flooring, encapsulated beneath the current carpeting, intricate custom woodwork, vintage fully-glassed sunroom windows & a delightfully charming sunroom. The eat-in kitchen is stocked with a full appliance package, a butlers Dream pantry and mudroom access to the private, well shaded, sprawling grounds. A resounding testament to Golden Era Construction of the 1920's, this homes 2 spacious bedrooms are painted in tasteful/warm earth tones with painstaking attention paid to integrity preservation by maintaining the original crystal door hardware and wood flooring. Nestled comfortably within one of Watertown's coveted neighborhoods conveniently close to major transit & a plethora of fine dining establishments further enhance the homes intrinsic value. Consistently maintained & updated mechanicals, a Newer Roof, a detached garage with ample parking & a desirable Location distinguish this property amongst its peers.

26 Fairview St, Watertown
$235,900
2 Beds ⋅ 2 Baths ⋅ 24200579 MLS
MOVE-IN READY & BEAUTIFULLY UPDATED! Don't let the size fool you-this charming Oakville home offers more living space than you might expect! The main level features a bright, updated interior with modern finishes and a comfortable, easy-to-maintain layout. The finished, heated walk-out lower level provides valuable additional living space complete with a second kitchen and full bathroom-ideal for extended living, guests, a home office, or recreation space. Enjoy the convenience of central air, natural gas, public water and sewer, plus exterior improvements including newer retaining walls and stairs. Conveniently located near shopping, restaurants, schools, and major routes. A great alternative to renting or condo living! Move right in and make it yours!

54 Buckingham St, Watertown
$220,000
2 Beds ⋅ 2 Baths ⋅ 24186305 MLS ⋅ Highgate BLDG.
Welcome home to this well-maintained 2-bedroom, 2-bath condo offering over 1,000 square feet of comfortable living space. Inside, you'll find a clean, inviting interior with spacious rooms and well-kept carpeting throughout. Step outside onto the low-maintenance Trex deck, the perfect spot to enjoy your morning coffee while overlooking the peaceful backyard. Tucked away in a quiet setting, this condo offers the perfect blend of comfort, convenience, and easy, low-maintenance living with plenty of space to make your own.

245 Cherry Ave Unit E24, Watertown
$219,900
3 Beds ⋅ 1 Baths ⋅ 24198831 MLS
A terrific condo alternative without the monthly HOA fees! This affordable single-family home features hardwood floors throughout and offers a flexible two or three-bedroom layout third bedroom would make a great home office. The inviting eat-in kitchen includes a tiled floor and stainless-steel appliances. Additional highlights include one full bath, natural gas heat, a newer roof, and an updated electrical panel. The walkout basement features washer and dryer hookups, plenty of storage, and convenient access to the fenced-in backyard-perfect for relaxing, entertaining, or pets. A wonderful opportunity to enjoy the privacy of a single-family home at an affordable price!

144 Sunnyside Ave, Watertown
$205,000
2 Beds ⋅ 2 Baths ⋅ 24187354 MLS ⋅ Highgate BLDG.
Welcome home to this spacious, two-bed, two bath, upper level end unit in a quiet, peaceful complex! Enjoy well-maintained grounds, open fields, scenic views, and a swimming pool that is perfect for summer. Find a beautiful built-in entertainment center/bookshelf/display case built and installed by the current owner. A roomy kitchen overlooks an open lawn. Two large bedrooms both have ample closet space and large windows to let in a lot of natural light! A small hall between bedrooms has a full bathroom, while the main bedroom has its own full bathroom. Find extra storage space in a walk-up attic. Relax in a large living/dining area. The Highgate complex is located in a pretty, small-town, picturesque neighborhood. Come make this home your own! Minutes from highways for commuters, shopping, schools, restaurants, recreation, local lakes, and more.

245 Cherry Ave Unit A24, Watertown
$205,000
1 Beds ⋅ 1 Baths ⋅ 24176270 MLS ⋅ The Ledges At Echo Lake BLDG.
Why rent when you can own? Welcome to The Ledges at Echo Lake, a newly built community completed in 2024 and designed for modern, low-maintenance living. This desirable first-floor ranch-style unit offers the convenience of one-level living with an open floor plan and bright, spacious living room that flows seamlessly into the fully applianced kitchen. The kitchen features stylish and durable engineered vinyl flooring, perfect for everyday living. The spacious bedroom includes a walk-in closet, and the unit is equipped with laundry hookups for added convenience. The full bathroom features a tiled walk-in shower. Additional amenities include central air conditioning and energy-efficient construction for year-round comfort. Whether you are a first-time or downsizing, or looking for an affordable alternative to renting, this unit offers outstanding value. Conveniently located near shopping, restaurants, parks, and major commuting routes, this is an excellent opportunity to own in one of Watertown's newest communities Don't miss your chance to become part of The Ledges at Echo Lake!

243 Echo Lake Rd Unit B4, Watertown
$199,900
2 Beds ⋅ 1 Baths ⋅ 24188866 MLS ⋅ Porter East BLDG.
Here is the chance to get your hands on a well maintained and rare 3 units condos sold together as a part of 5-unit association with long-term tenants in place. Current unit is leased for $1500 per month and has 2 bedrooms and 1 bath, kitchen and living room, all in a good condition and updated throughout years. Kitchen has nice cabinets and laminate flooring put in lately and extends on the other rooms. A good size living room following in the back of the kitchen area with a sliding door that leads to outside porch, which is freshly painted and used as a hangout place. The only full bathroom has tile flooring and updated cabinets. Primary bedroom is spacious compared to the size of the unit and layout of the space which allows for maximum usage of the whole area. Unit has 2 assigned parking spaces as well as stackable washer and dryer (both new). This unit can be sold as a package(preferred) with 237 porter st listing MLS#24188844 and 243 Porter st listing MLS#24188869, but seller will consider selling separate. Call today to find out for more details and get this investment package before is too late!

239 Porter St Unit 239, Watertown
$195,000
2 Beds ⋅ 2 Baths ⋅ 24201110 MLS ⋅ Highgate BLDG.
Welcome to this beautifully maintained 2-bedroom, 2-bathroom ranch-style flat, located on the second floor as an end unit in the sought-after Highgate Condos community. This layout offers single-level living with the privacy and quiet of an end-unit. Inside, you'll find two spacious bedrooms, including a primary suite with its own en suite bathroom for added comfort and convenience. Hardwood floors run throughout the kitchen and hallways, while the living spaces feature freshly cleaned carpets, ready for you to move right in. The updated kitchen offers modern finishes, making everyday cooking and entertaining a pleasure. Step outside to enjoy valley views from the community pool and a private, wooded backyard setting that feels like a peaceful retreat. With heat and hot water included in the HOA payment, monthly expenses stay predictable and low. This is a fantastic opportunity to stop paying rent and start building equity in an affordable, move-in ready home in one of Watertown's most desirable neighborhoods. Don't miss your chance to make this condo yours!

245 Cherry Ave Unit D24, Watertown
$189,900
1 Beds ⋅ 1 Baths ⋅ 24203065 MLS ⋅ Highgate BLDG.
Charming One- Bedroom Condominium with a Beautiful Tree-Lined View!! Welcome home to this inviting one bedroom condominium featuring a wonderful combination of comfort, style and peaceful surroundings. The updated kitchen offers attractive butcher block and granite countertops, and plenty of cabinetry for all your storage needs. The spacious living room and dining area provide plenty of room for relaxing and entertaining with access to your private deck- the perfect spot to enjoy your morning coffee or unwind at the end of the day while taking in the beautiful views of the treed lined yard. A comfortable bedroom and full bath complete this lovely condo. Surrounded by mature trees and natural beauty , this lovely condo offers a peaceful setting while providing the convenience and easy maintenance of condominium living.

245 Cherry Ave Unit O21, Watertown
$159,900
2 Beds ⋅ 1 Baths ⋅ 24188844 MLS ⋅ Porter East BLDG.
Rare opportunity to own this well-maintained condo as a part of 5-unit condo association with low taxes and easy to manage. Property features kitchen with tile flooring, living room with new laminate flooring and sliding door that leads to a wooded patio for relaxing or family gatherings. The 2 good sized bedrooms are located on the back of the unit, and both have laminate flooring. Currently is rented to a long-term tenant for $1300 a month, below the market value. Seller owns majority of the units of the association and prefers selling this unit together as a package with units 239 and 243 Porter st, but will consider selling separate.

237 Porter St Unit 237, Watertown
$54,900
1 Baths ⋅ 24188869 MLS ⋅ Porter East BLDG.
Opportunity is knocking to get to an investment property with less work to maintain and increase your profits as you go. The stand-alone building condo/studio is part of a 5-unit association with low taxes, which make it more appealing to investors or owner occupied alike. Currently rented to a long-term tenant this unit is basically one bedroom, one bath, kitchen and living area good enough for someone that wants something on their own, without anything to do outside. Unit has 1 parking space. Rented at below market value on month-to-month basis, since tenant has been renting for a long time and keeping the unit in good condition. This unit can be sold together as a package with 237 Porter street listing MLS#24188844 and 239 Porter street listingMLS#24188866 or Separate.

243 Porter St Unit 243, Watertown

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.