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$299,500
4 Beds 2 Baths ACTIVE Status 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

$389,900
3 Beds 2 Baths ACTIVE Status 24203142 MLS
Welcome to 21 Lancaster Street in Watertown! This well-maintained 3-bedroom raised ranch offers a comfortable layout with finished living space on both levels and central air throughout. The main level features a spacious living room, dining area, and kitchen with granite countertops, along with three bedrooms, including one with newer vinyl plank flooring. A full bathroom completes the main level. The finished lower level provides additional flexible living space and includes a half bathroom, laundry area, and direct access to the attached two-car garage. A pellet stove has been added to the lower level, providing an additional source of heat and creating a warm and inviting space to relax. Outside, enjoy the private two-tier Trex deck overlooking the above-ground pool. The pool features a new liner, while the fenced backyard provides a private space to enjoy the warmer months. The current owners have also utilized a wood-fired setup to help heat the pool, providing an additional option for extending pool season. The home is conveniently located close to Swift Middle School and offers easy access to shopping, dining, recreation, and major routes. With its finished lower level, pellet stove, central air, two-car garage, private Trex decking, and above-ground pool with a new liner, 21 Lancaster Street offers a great combination of comfort and functionality.

21 Lancaster St, Watertown

$650,000
4 Beds 3 Baths ACTIVE Status 24202221 MLS
Welcome to this beautifully updated 9-room Georgetown Dr. Colonial, offering 4 upper level bedrooms with a practical laundry room, a dedicated office, 3 bathrooms, a 2 car garage, and a landscaped .46-acre lot with the convenience of public water and sewer. This exceptional Strachan built home combines timeless architectural details with modern updates and everyday comfort. Inside, you'll find the quality finishes you would expect in a custom home, including crown molding, window cornices, built-in bookshelves, window seats, sliding doors, molded wainscoting, hardwood floors, a propane fireplace, and hydro-air heating and central air. The spacious kitchen has been beautifully updated with quartz countertops and GE appliances, and is accessible to the other main level rooms creating an inviting space for both everyday living and entertaining. Additional improvements over the last ten years include a new boiler and BoilerMate hot-water tank, a new roof with gutters and gutter covers, a refreshed composite rear deck, a repaved driveway, two newer A/C units, and a recently updated primary bathroom. The lower level adds even more versatility, featuring a rec. room & convenient kitchenette. Sliding doors open to a private concrete patio, offering a wonderful spot to relax or entertain. With its desirable Georgetown Dr. location, thoughtful updates, beautiful craftsmanship, and flexible living spaces, this home offers the ideal blend of classic charm and modern convenience.

263 Georgetown Dr, Watertown

$424,999
3 Beds 2 Baths ACTIVE Status 24204824 MLS
Completely renovated from top to bottom-this home has been thoughtfully redone with virtually nothing left untouched. Updates include a brand-new septic system, oil tank, heating system, plumbing, electrical service and panel, kitchen, bathrooms, well pump and tank, water heater, and windows. The roof is less than 10 years old, and the lawn has been freshly seeded and hayed for new grass to grow. All there is left to do is move in. All of this is completely private and tucked away, offering a peaceful setting surrounded by open land that cannot be developed, providing a rare sense of privacy, tranquility, and beautiful views. Despite the secluded feel, you're just minutes from major amenities and close to local farms offering fresh, locally grown products. Enjoy the best of both worlds-a quiet country setting with everyday conveniences close at hand, all in a home where the major work has already been done.

1774 Bunker Hill Rd, Watertown

$740,000
4 Beds 3 Baths COMING SOON Status 24203816 MLS
Welcome Home! Set on a spacious 2.92-acre lot overlooking preserved farmland, this one owner, custom built beautifully appointed 4-bedroom, 2.5-bath home offers an exceptional blend of comfort, functionality, and tranquil surroundings. Enjoy both beautiful sunrise and sunset views and peaceful rolling hills from this thoughtfully designed property. The open-concept first floor features hardwood flooring throughout and a stunning kitchen with solid wood cabinetry, granite countertops, stainless steel appliances, and a convenient pantry. The kitchen flows seamlessly into the living room, complete with a gas-insert fireplace, smart thermostats for comfort and surround-sound speaker system, creating an inviting space for both everyday living and entertaining. The dining room features an attractive inlaid decorative hardwood border. A convenient mudroom/drop zone and powder room are located just off the oversized 3-car garage, which includes a workbench and built-in storage. An electric vehicle charging station and installed invisible-fence pet containment system add even more versatility. Upstairs, four bedrooms surround a comfortable sitting area overlooking the dramatic two-story foyer. The spacious primary suite features hardwood flooring, a private bath with an updated tiled walk in shower and a large walk-in closet. Two bedrooms feature newer carpet installed approximately one year ago while the 4th bedroom has hard wood and is currently serving as a private home office.

42 Windy Ridge Ln, Watertown

$399,000
3 Beds 2 Baths COMING SOON Status 24204811 MLS
Cute as a button, this expanded Cape is conveniently located near Taft School and within walking distance to downtown Watertown. Hardwood floors run throughout much of the home, where the first floor offers a spacious living room with a pellet stove, dining room, kitchen, and full bath. Just off the kitchen, the sunken family room is a welcome addition, featuring a propane fireplace flanked by built-ins and access to the back deck. Upstairs, the primary suite offers an updated bathroom and generous closet space, along with two additional bedrooms, including one with built-ins. Outside, enjoy the large back deck, a level yard with room to play, and a one-car under-house garage. A charming home in a convenient Watertown location!

286 North St, Watertown

$350,000
3 Beds 2 Baths ACTIVE Status 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

$399,900
3 Beds 2 Baths ACTIVE Status 24173196 MLS
"Coming Soon" Welcome to 1620 Guernseytown Road! Lovingly maintained by the same family for more than 50 years, this solid three-bedroom ranch reflects genuine pride of ownership. When something needed attention, it was repaired or replaced with care. The home features 11/2 baths, a remodeled eat in kitchen, some hardwood flooring, charming built-ins, and a spacious living room with a wood-burning fireplace. A dedicated home office provides a comfortable space for working from home or can be used as a cozy family room, while the gorgeous three-season room offers peaceful views of the beautifully cleared 1.36-acre property. Additional highlights include Central-air, an oversized two-car garage, a full basement with abundant storage, a newer roof, and newer windows. With a little cosmetic TLC and your own personal touches, this well-built home offers tremendous potential and the opportunity to make it truly your own.

1620 Guernseytown Rd, Watertown

$439,000
4 Beds 3 Baths ACTIVE Status 24203894 MLS
Step back in time and experience the timeless character of this beautiful Colonial in Watertown, built in 1840. Ideally situated on a spacious corner lot. Rich with rustic charm and historic details, this unique home features original wood floors, generous living spaces, and several fireplaces that add warmth and character throughout. The large kitchen provides plenty of room for gathering and everyday living, while a cozy den with a pellet stove opens to a stunning sunroom featuring soaring ceilings, and an abundance of windows overlooking the expansive backyard. With three bedrooms plus dedicated office space, the home offers a flexible layout to suit a variety of needs. One of the bedrooms features a distinctive spiral staircase leading to a private loft area, adding even more charm and versatility. The main-level bathroom is highlighted by a beautiful soaking tub, creating a relaxing retreat. Step outside and discover a backyard designed for both entertaining and relaxation, complete with an in-ground pool, outdoor firepit, and a rustic open-air pool house featuring a beautiful fireplace and bar. Additional features include an alarm system, an established dog fence surrounding the yard, and extra driveway space for convenient parking. Offering a rare combination of 1840s character, spacious indoor and outdoor living, and a desirable location, this one-of-a-kind Watertown property is ready for its next chapter. Property Sold in "AS IS" Condition

635 Northfield Rd, Watertown

$195,000
2 Beds 2 Baths ACTIVE Status 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

$379,999
3 Beds 2 Baths ACTIVE Status 24201695 MLS Artillery Hill BLDG.
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 and tennis courts. Enjoy the convenience of being local to excellent shopping, dining and daily amenities. Turn-key, meticulously maintained, and full of upgrades.

101 Cannon Ridge Dr Unit 101, Watertown

$189,900
1 Beds 1 Baths ACTIVE Status 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

$589,000
3 Beds 2 Baths ACTIVE Status 24200345 MLS
Welcome to this beautifully maintained three-bedroom ranch nestled in one of Watertown's most sought-after neighborhoods. From the moment you step inside, you'll appreciate the bright, inviting atmosphere and comfortable layout. The spacious living room with a gas fireplace seamlessly flows into the updated kitchen, featuring stainless steel appliances, ample cabinetry, and plenty of workspace. Just off the kitchen, the dining area makes a statement with its soaring cathedral ceiling, oversized window bringing in an abundance of natural light, and elegant chandelier. Hardwood flooring extends throughout the main level, adding warmth and timeless appeal. The primary suite offers a relaxing retreat with a private full bath and generous walk-in closet. Two additional well-sized bedrooms provide flexibility for family, guests, or a home office. Convenient main-level laundry includes a laundry room already plumbed for a wash sink. Step directly from the kitchen onto the patio, complete with a charming pergola-an inviting space for morning coffee, outdoor dining, or entertaining guests. Additional highlights include newer central A/C installed in 2021 and a driveway paved within the last few years. This bright and welcoming ranch offers comfortable one-level living with thoughtful updates and plenty of appeal! MOVE QUICK!

116 Pond View Dr, Watertown

$235,900
2 Beds 2 Baths ACTIVE Status 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

$914,900
3 Beds 3 Baths ACTIVE Status 24197147 MLS
Single Owner - Custom Built 3093sqft all Brick and Stone Colonial set on 6.11 estate like acres with heated in-ground swimming pool, pool house, basketball court, and plenty of parking. Potential for further development with additional 1 acre lot included. Quality construction includes hardwood, tile, and granite countertops throughout. Living room with Fireplace and crown molding. Dining room with simulated paneling and crown. 3 season room with indoor hottub. Eat-in-kitchen with granite and breakfast bar center island. Mudroom, laundry room and 1/2 bath. Upstairs Master suite with large space, 3 walk-in closets, and attached full bath 2nd and 3rd bedrooms both with walk in closets. full bath. Bonus room with skylight and vaulted ceilings. Expansive lower level recreation room. Unfinished wine cellar in basement. Sprawling lot with in-ground pool, basketball court that could potentially be repurposed for pickleball or other sports, gardens, bocce courts. Large paved area for parking. Covered brick patio perfect for entertaining in all weather. Strong mechanicals include central air, hydro air, central vac and 200 amp electrical. Make this your own family compound! Sale includes a total of 3 parcels consisting of 4.89 acres at 555 Davis St, 1 acre on D'agostino Dr, which may be an additional building lot, and .22 acres on Elena Dr. Buyer to do due diligence.

555 Davis St, Watertown

$645,000
3 Beds 4 Baths ACTIVE Status 24194045 MLS
Off a quiet country road this circa 1941 Cape Cod style home is perched privately in the center of an idylic eight acre country estate. Reimagined and renovated 3 bedroom 3.5 bath 3343 square foot home features expanded kitchen, updated baths, new carpet, built-ins, and is ready for its new owner! Closets galore. New roof, new ductless mini split system. Upper level master bedroom suite boasts high ceilings, fireplace, and a Juliet balcony overlooking secret gardens and patio area with a "courting bench". 4 fireplaces. Whole house generator. Large red barn with walk-up stairs to extra storage space. Oversized 2 car detached garage with finished upper level apartment. The property itself is everything you might hope for: Trellis and arbor patio overlooking a waterfall, walking paths, stone walls, mature landscaping, specimen trees...simply amazing!

240 Skilton Rd, Watertown

$325,000
3 Beds 1 Baths ACTIVE Status 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

$899,900
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

$89,900
ACTIVE Status 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
ACTIVE Status 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

$367,750
3 Beds 2 Baths ACTIVE Status 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

$199,900
2 Beds 1 Baths ACTIVE Status 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

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