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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

36 Falls Ter, Watertown
$349,000
2 Beds ⋅ 1 Baths ⋅ 24210723 MLS
If you are looking for a flat piece of land with modern updates throughout, this is for you. Move in ready 3 bed 2 bath Overlook nearly half an acre of cleared land from your newly installed Trex deck with gazebo. Home offers a comfortable layout with beautiful wood kitchen cabinetry, granite countertops, and plenty of windows that fill the space with natural light. The current owners have lovingly called this their first home for the past 10 years and have taken great care of the property. They made the most of the space, creating a home that is comfortable and functional for their children. They planted Evergreens along the front lawn, adding backyard privacy for years to come. A large, cleared yard, inviting outdoor space, updated interior, and a home that has been truly cared for make this one worth seeing.

36 Falls Ter, Watertown

85 Claxton Ave, Watertown
$349,900
3 Beds ⋅ 2 Baths ⋅ 24210793 MLS
Welcome to this beautifully maintained Cape, ideally situated in an established Watertown neighborhood and filled with the warmth and character that make a house feel like home. Set on a level.27-acre lot framed by mature trees, the property offers wonderful curb appeal, a private fenced backyard, and a covered porch perfect for relaxing, entertaining, or enjoying a quiet morning coffee. Inside, hardwood floors and charming architectural details add character throughout. The spacious front-to-back living room features a wood-burning fireplace and built-in cabinetry, while the formal dining room offers additional built-ins and plenty of space for gathering. The eat-in kitchen, a first-floor bedroom, and a full bath provide a comfortable and flexible main-level layout. Upstairs, you'll find two generously sized bedrooms, including the current primary bedroom, along with a convenient half bath. The finished lower level provides even more living space and features its own heating zone-ideal for a family room, home office, recreation area, gym, or combination of uses. A detached one-car garage, newer roof, windows, and siding add to the home's appeal. With its classic Cape architecture, inviting outdoor spaces, flexible floor plan, and desirable Watertown location, this is a home you'll want to see in person.

85 Claxton Ave, Watertown

57 Sunnyside Ave, Watertown
$359,900
4 Beds ⋅ 2 Baths ⋅ 24209970 MLS
ATTENTION INVESTORS & OWNER-OCCUPANTS! This longtime-owned two-family in the Oakville section of Watertown offers a unique opportunity with multiple possibilities. Set on a beautiful & spacious 1.17 acres, the property is ideal for an owner-occupant, investment, or multi-generational living arrangement. The second-floor owner's unit is filled with charm and character, featuring one bedroom with a bright bonus room right off of it flooded with natural light-perfect for a home office, art room, library and reading sanctuary or quiet retreat. The living room offers hardwood floors and a custom cherry built-in wood cabinet, while the partially finished third-floor attic includes two additional rooms with built-in beds and dressers. The first-floor apartment is ready for its next chapter, with much of the space already gutted to the studs, insulated and prepared for renovation. Major updates include a newer furnace, hot water heater, updated electrical and replacement windows. Add a welcoming front porch with the original antique carved hardwood front door with custom glass window, carport, off-street parking and convenient access to Route 8, I-84, shopping and area amenities. Bring your vision and make this unique property your own!

57 Sunnyside Ave, 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

215 Smith Pond Rd, Watertown
$545,000
3 Beds ⋅ 3 Baths ⋅ 24209717 MLS
Custom Crafted Cape nestled on level private 1.35 acre lot is destined to impress! Main level offers an open flow in the floor plan with living room, dining area with sliding glass doors to spacious deck, stunning kitchen appointed with cherry cabinets, granite counter tops, center island and stainless appliances. Main level primary bedroom boasting full bath, walk in closet and ceiling fan, half bath with laundry and hardwood flooring throughout complete this level. The upper story features 2 generous sized bedrooms, bonus room and second full bath with double vanities. The lower level features recreational room, and plenty of storage space. Additional amenties include oversized two car garage, central air conditioning, cost effective propane gas heating, fenced lot and storage shed. This gem is located just minutes to Interstates 8 and 84 as well as multiple restaurants, golf course, parks and shopping!

215 Smith Pond Rd, Watertown

19 Pythian Ave, Watertown
$449,900
8 Beds ⋅ 3 Baths ⋅ 24209524 MLS
Investor-ready three-unit multifamily offering strong cash-flow potential in Watertown. 19 Pythian Avenue features two spacious side-by-side 3-bedroom units, plus a fully finished lower-level 2-bedroom unit, creating multiple income streams under one roof. This property is built for an investor looking for a straightforward addition to their portfolio - collect the keys, collect the rents, and start generating income. Major improvements include a roof approximately three years old, helping reduce near-term capital expenditure concerns. A standout feature is the property's solar system, which provides an additional income stream to the landlord through energy sold back to the grid, currently generating approximately $640+ per month. Combined with rental income from all three units, this creates an attractive opportunity to maximize the property's overall revenue potential. The property also offers convenient off-street parking and a practical multifamily layout that supports strong tenant demand. Whether you're expanding an existing portfolio, purchasing your first multifamily investment, or looking for an income-producing property with multiple revenue streams, 19 Pythian Avenue presents a compelling opportunity in Watertown. Three units. Multiple income streams. Parking. Newer roof. Solar revenue. Ready to cash flow.

19 Pythian Ave, Watertown

59 Dalton St, Watertown
$325,000
3 Beds ⋅ 2 Baths ⋅ 24208943 MLS
This beautifully maintained Cape is tucked away on a quiet back street, offering a welcoming setting and a fully fenced backyard-perfect for pets, play, relaxing, and entertaining. Step inside to find gleaming hardwood floors and updated tile throughout. With bedrooms and a full bath on both floors, the flexible layout offers comfortable living for a variety of needs. The convenient mudroom provides the perfect place to unload at the end of the day and opens directly to a spacious deck overlooking the gorgeous backyard. You'll especially appreciate the comfort of radiant heat on the first floor along with cozy steam heat throughout the home. Important mechanical updates include 200-amp electrical service, a Burnham boiler, and a double-wall stainless-steel oil tank, providing added confidence for years to come. Warm, comfortable, and beautifully cared for-this is a home you'll want to see!

59 Dalton St, Watertown

142 Lexington Dr, Watertown
$450,000
3 Beds ⋅ 2 Baths ⋅ 24208939 MLS
*** Highest and Best offers due Saturday Sept 26th 8PM*** Charming and beautifully updated ranch offering comfortable one-level living with plenty of flexible space. The inviting kitchen features beautiful wood cabinetry, a center island and an open flow into the dining room, making it a wonderful space for everyday living and entertaining. The primary bedroom offers a private half bath, with an additional room currently used as an office that provides the flexibility of a third bedroom. An updated full bath completes the main level. A true highlight is the expansive sunken family room/sunroom, filled with natural light and overlooking the beautifully established grounds. The finished lower level provides additional living space, while central air and a two-car garage add convenience. Outside, enjoy a large, level lot filled with mature perennials, colorful gardens and raised garden beds, plus a spacious shed for storage. A lovely home with flexible space, beautiful gardens and plenty of room to enjoy inside and out.

142 Lexington Dr, Watertown

600 Thomaston Rd, Watertown
$374,900
3 Beds ⋅ 2 Baths ⋅ 24208569 MLS
Make no mistake - this house is perfect for a handy person looking for a great opportunity! Nestled on a spacious, flat 2-acre lot, there's plenty of room in backyard for fun and outdoors activity. Enjoy an easy commute to Routes 8 & 84. Recent upgrades are a new roof and siding in 2024, ensuring low maintenance for years to come. There is an attached 2 car garage with a convenient walk up loft for extra storage. The Bico door in the basement has been replaced and new side walls were also replaced, to prevent water seepage. Inside, the loft master bedroom has a full bath. An eat-in kitchen, a fireplace in the living room and a first floor family room with wood stove-perfect for the chilly evenings coming up. With so much potential and space this property is a fantastic find for the right buyer.

600 Thomaston Rd, 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

282 Sunnyside Ave, 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

21 Lancaster St, Watertown
$389,900
3 Beds ⋅ 2 Baths ⋅ 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

263 Georgetown Dr, Watertown
$650,000
4 Beds ⋅ 3 Baths ⋅ 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

1774 Bunker Hill Rd, Watertown
$424,999
3 Beds ⋅ 2 Baths ⋅ 24204824 MLS
****Offer deadline is Sunday the 20th at 6pm**** 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

42 Windy Ridge Ln, Watertown
$740,000
4 Beds ⋅ 3 Baths ⋅ 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

286 North St, Watertown
$399,000
3 Beds ⋅ 2 Baths ⋅ 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

1620 Guernseytown Rd, Watertown
$399,900
3 Beds ⋅ 2 Baths ⋅ 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

245 Cherry Ave Unit D24, 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

101 Cannon Ridge Dr Unit 101, Watertown
$379,999
3 Beds ⋅ 2 Baths ⋅ 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

245 Cherry Ave Unit O21, 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

116 Pond View Dr, Watertown
$579,000
3 Beds ⋅ 2 Baths ⋅ 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 and furnace 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

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