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19 Henry St, Watertown
$355,000
3 Beds ⋅ 2 Baths ⋅ 24140910 MLS
Step into effortless, turnkey living at 19 Henry Street, a beautifully updated 3 bedroom, 1.5 bathroom Colonial tucked away on a quiet Oakville cul-de-sac and filled with abundant natural light. The spacious living room with a cozy fireplace flows seamlessly into the dining room, which opens to a large deck and connects to the completely remodeled kitchen featuring stainless steel appliances, white cabinetry with new hardware, quartz countertops, and a crisp white tile backsplash perfect for everyday living or entertaining. Both the full and half bathroom have been fully renovated, complementing the home's many upgrades including recessed lighting throughout, new windows, refinished hardwood floors, and fresh paint from top to bottom. Enjoy outdoor living on the expansive deck overlooking a cleared, well-maintained lot, along with a welcoming front porch that adds to the home's charm. Conveniently located near I-84 and Route 8 for an easy commute, and just minutes from shopping, restaurants, Watertown Parks & Rec, public transportation, and all that Litchfield County has to offer, this move-in-ready gem is truly one you won't want to miss.

19 Henry St, Watertown
163 Pawnee Rd, Watertown
$299,900
2 Beds ⋅ 2 Baths ⋅ 24152104 MLS
Charming two-bedroom Colonial tucked away in a sought-after private area of Watertown with picturesque views of Lake Winnemaug. Step inside to a cozy living room featuring a beautiful stone, wood-burning fireplace, perfect for relaxing evenings. The bright kitchen offers pine cabinetry, stainless steel appliances and luxury Formica countertops. The main level is complete with a laundry area and full bath. Upstairs, you'll find two nicely sized bedrooms and an additional full bath. Hardwood flooring throughout both levels. This home features propane-fueled forced hot air and baseboard electric heat to supplement, along with numerous updates including a newer well pump and holding tank, propane wall heating unit, electrical service, plumbing, roof, and windows, plus skylights throughout. Enjoy the added bonus of a finished outbuilding offering extra heated recreational space. Low taxes complete this exceptional opportunity. MOVE QUICK!

163 Pawnee Rd, Watertown
319 Thomaston Rd Unit 95, Watertown
$385,000
3 Beds ⋅ 3 Baths ⋅ 24159239 MLS ⋅ Watertown Old Farms BLDG.
Welcome to Watertown Old Farm and Enjoy Easy Condo Living in this Beautifully maintained 3 Bedroom Suites, 3 Full Bath Beacon Hill Model. There is a Primary Bedroom on the Main Level with a Full Bath that has a Stand-Up Shower. This Wonderful Unit features an Eat-in Kitchen w/Oak Cabinets, Newer SS Appliances, Pantry, and Dining Area w/Sliders that Lead to a Spacious Deck, Ideal for Relaxing or Entertaining. The Light & Bright Formal Living Room offers a Cozy Fireplace to Enjoy w/Family & Friends. The Ample Size 2nd & 3rd Bedrooms (each with own Full Bathrooms) also have Large Closets & Storage Space. The Lower-level Basement is a Partly Finished Walk-out, with Full Size Windows & a New Slider, which can Offer Endless Possibilities of Additional Living Space. This Unit Has a 1 Car detached Garage that has easy access from the Front Door. New A/C, Water Heater & Washer & Dryer. This Unit is a Must See and Close to all the Amenities that Watertown has to Offer with a Convenience of Condo Living.

319 Thomaston Rd Unit 95, Watertown
1123 Middlebury Rd, Watertown
$465,000
3 Beds ⋅ 2 Baths ⋅ 24161748 MLS
Welcome to this beautiful ranch-style home offering convenient one-level living. The main floor features a charming kitchen, dining room, and a cozy living room with a fireplace-perfect for relaxing or entertaining. Three comfortable bedrooms and a full bath complete the first floor, along with a newly renovated porch ideal for enjoying your morning coffee or evening unwind. The finished basement provides valuable additional living space, including a family room with an electric fireplace and French doors leading out to the patio area-creating a seamless indoor-outdoor flow. A fully renovated bathroom with laundry adds extra convenience, making this space perfect for guests or extended living needs. Step outside to a fully fenced yard featuring a large, gated garden area-great for gardening, pets, or outdoor enjoyment. Major updates completed in 2025 include a new roof, siding, windows, and doors, along with solar panels for improved energy efficiency and long-term savings. This move-in ready home combines comfort, style, and smart upgrades-don't miss your chance to make it yours!

1123 Middlebury Rd, Watertown
173 Pond View Dr, Watertown
$615,000
4 Beds ⋅ 4 Baths ⋅ 24155758 MLS
Beautifully maintained colonial in sought-after Pond View Estates offering rich, dark hardwood flooring that beautifully contrasts the home's bright, sun-filled interiors, creating a warm and sophisticated atmosphere throughout the main living spaces. The main level offers a wonderful flow for both everyday living and entertaining with a spacious living room featuring a gas fireplace, and French doors opening to a versatile room, currently used as a playroom, and can easily serve as a private home office, study, or additional living space. A sun filled formal dining room surrounded by beautiful windows provide the perfect setting for gatherings and special occasions. The eat in kitchen features custom maple cabinetry, quartz countertops, stainless steel appliances, & generous storage, with sliders leading out to a private deck overlooking the backyard. Upstairs you'll find a primary bedroom suite with walk-in his & her closets, along with two additional bedrooms & a full bathroom featuring a convenient laundry closet. The finished lower level expands the home's living space, offering a fourth bedroom, a full bath, and family room with walk out access to a bluestone patio. Recent improvements include a Navien high efficiency natural gas tankless water heater, a 96 percent efficient Rheem natural gas furnace, and central air system installed in late 2024. The backyard was also leveled in No 2020. This is a wonderful opportunity to own a spacious home in a desirable neighborhood

173 Pond View Dr, Watertown
21 Hidden Pond Dr, Watertown
$775,000
5 Beds ⋅ 4 Baths ⋅ 24160061 MLS
Stunning 4,414 Sq Ft Colonial in one of Watertown's most desirable neighborhoods! This beautifully maintained home offers exceptional space, comfort & versatility meeting multi-generational needs. Enjoy relaxing mornings & peaceful evenings on the inviting covered porch featuring removable screens. Inside you will find a large foyer with a grand spiral staircase. There is a large formal living room as well as a generous sized formal dining room perfect for entertaining family & friends. A gorgeous eat-in kitchen any home chef would enjoy is just off the dining area with a center island, large walk-in pantry, double ovens, dishwasher & cooktop make this a great functional kitchen. Off the kitchen is a large family room with sliders to the covered 3 season porch providing access to a beautiful brick patio. Upstairs there is a primary bedroom with ensuite & walk in closet. You'll also find 3 additional bedrooms, a full bath & a separate laundry room. Through the breezeway area there is an extra large office for working from home or great work out space. Upstairs off the breezeway is a guest area/in-law suite featuring a spacious living room/dinning room area, great kitchen, bedroom, full bath with a compact washer/dryer. This home is nestled on a professionally landscaped 1.92 acre lot! Don't miss this one!

21 Hidden Pond Dr, Watertown
55 Cannon Ridge Dr Unit 55, Watertown
$293,000
2 Beds ⋅ 2 Baths ⋅ 24159099 MLS ⋅ Artillery Hill BLDG.
Welcome home to this wonderful updated end unit townhouse. Located in desirable Artillery Hill. Come an experience a comfortable life style you deserve for years to come. Enjoy cooking in this elegant kitchen with SS appliances, granite counter tops perfect for everyday living and entertaining. Inviting living room to relax by the cozy fireplace. Two Spacious bedroom each offers generous closet space and comfort. Full bath an convenient half-bath for guest. Oversized garage with plenty of storage area. This townhouse is perfect for first time home buyers, downsizers, or anyone looking for low-maintenance living with stylish upgrades.

55 Cannon Ridge Dr Unit 55, Watertown
781 Hamilton Ave, Watertown
$351,800
3 Beds ⋅ 2 Baths ⋅ 24144298 MLS
Welcome to this charming 3-bedroom, 2-bath home in the heart of Watertown! Perfectly situated close to the center of town, this well-loved property offers comfort, convenience, and incredible potential for its next owner. Step inside to find a bright main level with a traditional layout and hardwood floors waiting beneath the carpet-an easy opportunity to elevate the home's character and style. The spacious living and dining areas flow comfortably, creating a warm setting for everyday living and hosting. Outside, the home truly shines with its large, private backyard-a rare find in this location. Whether you envision gardening, play areas, or summer gatherings, this yard is ready to become your personal retreat. Located just minutes from Watertown's shops, restaurants, parks, and amenities, this home blends privacy with everyday convenience. With solid bones and room to make it your own, this is a fantastic opportunity in one of Watertown's most desirable areas.

781 Hamilton Ave, Watertown
42 Wentworth Ct Unit 11, Watertown
$544,087
3 Beds ⋅ 2 Baths ⋅ 24095284 MLS
Easy Living Begins at Turnberry Estates - a thoughtfully designed 55+ adult community offering 32 single-story homes tailored for low-maintenance living. These to-be-built residences combine style and practicality with open-concept layouts, vaulted ceilings, and a range of customizable finishes to suit your personal taste. Each home features 3 bedrooms, 2 full bathrooms, and floor plans ranging from 1,444-1,610 square feet with an optional 12'x12' cathedral three or four-season sunroom. Highlights include a fireplaced living room, kitchen with island and stainless steel appliances, primary suite complete with walk-in closet and en-suite bath, an attached 2-car garage, full basement, covered front porch, and 10'x12' patio or deck. Enjoy the perfect balance of design and convenience in a serene setting just minutes from local dining, shopping, parks and rec, and Route 8. This Planned Unit Development will start occupancy Fall 2025. Phases 1 and 2 are fully reserved - Phase 3 waitlist now forming. Agent related.

42 Wentworth Ct Unit 11, Watertown
99 Cannon Ridge Dr Unit 99, Watertown
$401,000
3 Beds ⋅ 2 Baths ⋅ 24162734 MLS ⋅ Artillery Hill BLDG.
"Coming Soon" Completely renovated and move-in ready, this exceptional 3-bedroom residence at 99 Cannon Ridge Drive offers refined living across three thoughtfully designed levels. The main level showcases a beautifully remodeled eat-in kitchen, seamlessly flowing into an expansive living and dining area anchored by a fireplace creating a warm yet sophisticated space for both everyday living and entertaining. Sliders in the dining area open to a private deck, offering the perfect setting for morning coffee or evening relaxation. Two generously sized bedrooms and a well-appointed full bath complete the main level, providing both comfort and flexibility. The upper level is dedicated to a private primary suite retreat, featuring a full bath, walk-in closet, and a separate office area ideal for today's work-from-home lifestyle. A conveniently located second-floor laundry room and additional attic access enhance everyday functionality. The fully finished walk-out lower level adds a new dimension of living space, offering a gym area, spacious family room, and recreation area with a wet bar perfectly suited for entertaining, extended stays, or multi-generational living. Additional highlights include a one-car garage and access to a meticulously maintained complex of 125 units, with recent improvements including newly paved driveways and roadways. Residents enjoy low-maintenance living complemented by community amenities such as a swimming pool. Don't wait call Today!!

99 Cannon Ridge Dr Unit 99, Watertown
5 Plungis Rd, Watertown
$520,000
4 Beds ⋅ 3 Baths ⋅ 24163004 MLS
Set on just over 4.5 beautiful acres, this updated 4 bedroom, 2.5 bath home offers a wonderful blend of comfortable living and outdoor enjoyment. The home features an updated kitchen, along with newer windows throughout the home and a newer boiler, providing both style and efficiency. Central air upstairs, mini splits 1st floor for complete comfort in the warmer months. Sliders lead out to a spacious deck, ideal for relaxing or entertaining while enjoying views of the expansive yard. Outdoor highlights include an aboveground salt water swimming pool and a large pond offering year round enjoyment, perfect for ice skating in the winter, fishing, or canoeing. Ideally located close to Hawk Ridge Winery, local eateries, and nearby farms, this property offers a lifestyle connected to the best of the area's dining, agriculture, and recreation-all while enjoying generous land and inviting amenities.

5 Plungis Rd, Watertown
1729 Litchfield Rd, Watertown
$799,000
4 Beds ⋅ 4 Baths ⋅ 24155493 MLS
Exceptional custom contemporary set on a rare 9.4 acre private, interior lot, just minutes to Litchfield center! Offering approx. 3,400 sq ft, this home showcases custom woodwork and architectural detailing throughout. Upon entry, you're welcomed by a formal living room & dining room, defined by hardwood floors, soaring cathedral ceilings, a gas fireplace, & elegant custom pillars that create a striking first impression and timeless sense of scale. The home then flows seamlessly into the eat in kitchen, featuring a center island, granite countertops, stainless steel appliances, &a tray ceiling-ideal for both every day living & entertaining. The spacious sun room off of the kitchen offers sliders leading to an 18x34 heated in ground pool with a brand new liner & jacuzzi, all surrounded by peaceful, wooded privacy. A main level primary suite with full bath and convenient main level laundry add ease and functionality. The second floor features a loft overlooking the living room & dining room, three bedrooms, and an additional living room with gas fireplace, and wet bar. An additional room on the second level could easily function as a home office or use your imagination! 3.5 baths have all been remodeled. Additional features include a 3 car garage(3rd bay, negative pressure, dust free) central air (new first floor unit), 4 zone heat, central vac, abundant storage with tons of closets and pull down attic, central speaker system with subwoofer, & a 2500-watt generator.

1729 Litchfield Rd, Watertown
249 Old Farms Rd, Watertown
$976,000
5 Beds ⋅ 5 Baths ⋅ 24164896 MLS
Proudly introducing, first time on market, 249 Old Farms Rd! Custom built with magnificent attention to detail. Timeless sophistication meets resort-style living in this 10-room Regal Colonial set in one of Watertown's premier locations. The kitchen is a chef's dream with custom cabinetry, and flows seamlessly into formal living areas. Family room leads to an outdoor sanctuary featuring a pristine in-ground pool and an architecturally matching pool house. Home office is located on main level with French doors to pool/patio area. The primary bedroom on the second level is a dream come true with ample closet space, full bathroom and gas log fireplace, perfect for a romantic night! 4 additional expansive bedrooms and 3 more bathrooms plus finished basement is perfect for your home theater or game room. The mechanicals are beyond expectation including a generator. Three car oversized garage is perfect for the car buff with epoxy floors and cabinet storage. The enormous walk in attic can be accessed from the garage or bedroom. All this and much more on a cul de sac with City water/sewer, underground utilities, this property defines LUXURY at $975. OPEN HOUSE HAS BEEN CANCELLED.

249 Old Farms Rd, Watertown
9 Rockland Ave, Watertown
$328,000
4 Beds ⋅ 3 Baths ⋅ 24158337 MLS
HIGHEST AND BEST 3/18 12:00 There's room for everyone in this thoughtfully updated Colonial featuring a flexible layout, spacious living areas, and a lower-level living area with its own private entrance. Set on 0.39 acres, this move-in-ready home features refinished hardwood floors on the main level and new flooring throughout the upstairs. The main level welcomes you with an open living and dining room layout that flows seamlessly into the oversized kitchen featuring a large center island, perfect for gatherings, meal prep, and entertaining. A full bathroom on the main level adds everyday convenience, while a spacious room with a closet offers endless possibilities as a bedroom, home office, playroom, or additional flex space. Step outside to the deck overlooking the backyard, ideal for relaxing or hosting friends and family. Upstairs you'll find a generously sized primary bedroom with its own private staircase providing convenient access to the main level or outdoors and adding a unique sense of privacy. Two additional bedrooms are also located on the upper level with a versatile bonus room between them, perfect for a sitting area, nursery, office, or creative space. The lower level offers excellent storage along with a finished space featuring its own private entrance complete with a bedroom and bathroom-ideal for an in-law arrangement, guest suite, or potential income opportunity. Additional features include a one-car detached garage.

9 Rockland Ave, Watertown
20 Grandview Ave, Watertown
$415,000
3 Beds ⋅ 2 Baths ⋅ 24156055 MLS
Enjoy the ease of single-level living in this beautifully updated home, perfectly situated on nearly half an acre with breathtaking views. Step inside to a light-filled formal dining room featuring hardwood floors-an inviting space for everyday meals or special gatherings. The recently renovated kitchen is truly the heart of the home, showcasing stainless steel appliances, elegant quartzite countertops, a stylish backsplash, and a spacious island with seating-ideal for entertaining. The kitchen flows seamlessly into a generously sized living room that has been fully updated with recessed lighting, luxury vinyl flooring, a mini-split heating and cooling system, and a recently added half bath. The sliding glass door opens to a deck overlooking the expansive backyard-offering stunning views and privacy. The main level also features three comfortable bedrooms and a beautifully remodeled full bathroom. The lower level provides additional flexibility with a partially finished space perfect for a play/rec room, home office, or potential fourth bedroom. A walk-out basement offers abundant storage and workspace, along with direct access to the backyard. Recent improvements include: New roof with spray foam insulation (2022), New heat pump (2019), New oil tank (2018), New driveway (2015), Updated interior doors and trim throughout. The backyard is ready for summer enjoyment with a brand-new above-ground pool installed in July 2025.

20 Grandview Ave, Watertown

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