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$394,900
4 Beds ⋅ 2 Baths ⋅ 24206482 MLS
Welcome to 33 Chestnut Grove in Watertown! This well-maintained 4-bedroom, 2-bath home offers approximately 1,500 sq. ft. of comfortable living space. Featuring beautiful hardwood floors throughout, a freshly painted interior, and a brand-new driveway, this home is move-in ready. Additional highlights include a spacious 2-car garage and plenty of room for everyday living and entertaining. Conveniently located near local amenities, shopping, dining, and major routes. Schedule your showing today!

33 Chestnut Grove Rd, Watertown
$380,000
4 Beds ⋅ 2 Baths ⋅ 24205654 MLS
16 Slade Ter is a residence with a functional layout and comfortable living spaces throughout. The kitchen features an accent backsplash and stainless steel appliances, creating a well-equipped space for cooking and entertaining. Interior paint extends throughout. The primary bathroom includes double sinks for everyday convenience. A deck extends the living space outdoors, creating ample room for relaxation and entertaining, and exterior paint completes the exterior. This residence combines practical design with comfortable living spaces, delivering functional amenities throughout every room.

16 Slade Ter, 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
$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
$359,900
2 Beds ⋅ 3 Baths ⋅ 24198813 MLS ⋅ Watertown Old Farms BLDG.
Tastefully remodeled Watertown Old Farms condo. Remodeled eat-in-kitchen with quartz countertops, stainless steel appliances, and tile backsplash. Living room with fireplace and slider to nice private deck. Half bath and main level laundry room. Two bedrooms upstairs both with attached remodeled full baths. 1 car garage. Full basement for additional sqft or or storage. New hot water heater. Central air. City water and sewer.

319 Thomaston Rd Unit 39, 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
$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
$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
$379,900
3 Beds ⋅ 2 Baths ⋅ 24202764 MLS
Welcome to this move-in-ready 3-bedroom, 2-full-bath Ranch nestled in the Oakville section of Watertown! Set on approximately a quarter acre of beautifully landscaped, level property, this charming home offers comfortable one-level living with thoughtful updates throughout. Step inside to find gleaming hardwood floors, a bright and inviting layout, and a well-appointed kitchen featuring granite countertops and stainless-steel appliances. The spacious living areas provide plenty of room to relax and entertain, while three comfortable bedrooms and two full bathrooms offer the convenience today's buyers are looking for. The partially-finished, heated basement provides valuable additional living space with endless possibilities-use it as a recreation room, home office, guest space, or potential in-law area. The possibilities are yours to make it fit your lifestyle! Outside, enjoy the professionally landscaped, flat yard and restored, freshly painted deck-perfect for morning coffee, summer gatherings, or simply enjoying your own private outdoor space. The entire exterior of the home has also been freshly painted, adding to its excellent curb appeal. Conveniently located in Watertown's Oakville section, this home combines easy living, versatile space, and a beautifully maintained property. Just unpack and enjoy!

40 Westview Dr, 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
$369,900
2 Beds ⋅ 3 Baths ⋅ 24201305 MLS ⋅ Watertown Old Farms BLDG.
MOVE RIGHT IN TO THIS LOVELY CONDO SET IN SOUGHT AFTER COMMUNITY! OPEN THE NUMEROUS WINDOWS & ENJOY SUNLIGHT & FRESH AIR THROUGHOUT YOUR HOME! BRIGHT KITCHEN WITH NEW STAINLESS STEEL APPLIANCES & BREAKFAST BAR. DINING ROOM WITH HARDWOOD FLOORING & SLIDERS TO DECK. LIVING ROOM IS ENHANCED BY COZY FIREPLACE & HARDWOOD FLOORING. HALF BATH & ADDITIONAL ROOM WITH POTENTIAL FOR DEN, OFFICE OR 3RD BEDROOM COMPLETE THE FIRST LEVEL. SECOND LEVEL FEATURES 2 BEDROOMS EACH BOASTING AN ENSUITE! PRIMARY BEDROOM HAS LARGE CLOSET WITH BUILT-INS. SPACIOUS FINISHED LOWER LEVEL WITH SLIDERS TO PATIO IS PERFECT FOR FAMILY ROOM, EXERCISE ROOM & MORE! ONE CAR GARAGE.

319 Thomaston Rd Unit 106, Watertown
$399,900
3 Beds ⋅ 1 Baths ⋅ 24200863 MLS
One of Watertown's most sought after neighborhoods, less than 1 block to Prestigous Taft School, This cozy 3 br ranch home is updated with lovely kitchen with new cabinets, granite counters, stainless appliances, full remodeled bathroom, gleaming hardwood floors, main level enclosed sunroom off the kitchen overlooking huge level back yard with unlimited possibilites, potential in basement for additional living space, garage access, huge driveway. Great curb appeal, Gas heating, central air, city water and city sewers...Don't miss out..

128 Middlebury Rd, 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
$375,000
3 Beds ⋅ 2 Baths ⋅ 24198416 MLS ⋅ Artillery Hill BLDG.
Welcome to this beautifully updated three-bedroom condo in the highly desirable Artillery Hill complex! Offering a flexible floor plan, this home can live like a ranch or a townhouse. The first floor features two bedrooms, a full bath, a spacious living room with a fireplace, and an updated kitchen with quartz countertops and newer stainless-steel appliances. Upstairs, the private primary bedroom suite includes its own updated full bath and walk-in closet. Additional improvements include updated flooring and mechanicals. Enjoy outdoor entertaining on the large deck, plus a one-car garage with additional storage above. Ideally situated in one of the complex's most desirable locations on a quiet cul-de-sac, this move-in-ready condo offers comfort flexibility and style a wonderful place to call home!

118 Cannon Ridge Dr Unit 118, Watertown
$387,000
24199419 MLS
All building permits in place. Approved, recently poured foundation and approved plot plan for a 3-5 bedroom house with walkout. Beautiful 3.24 acre lot. Ready to build. The largest lot in Highview Estates, possibly subdividable. Short drive to 84, 8, and 6; well-located. All utilities are underground at CURBSIDE: water, sewer, electric, gas, cable. Ready to build your dream house and don't want to start from scratch clearing land and getting approvals? This lot is for you!

100 Loop Rd, 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
$359,000
3 Beds ⋅ 3 Baths ⋅ 24197215 MLS ⋅ Artillery Hill BLDG.
Three-bedroom condominiums are a rare find in Watertown, and this spacious end-unit townhouse at Artillery Hill offers an exceptional combination of space, flexibility, and low-maintenance living. With more than 1,500 square feet, 2.5 baths, an attached garage, central air, and a full basement, the home provides many of the features of a single-family residence with the convenience of condominium ownership. The main level features an updated kitchen with white cabinetry, stainless steel appliances, a Carrera-style backsplash, and pantry storage. The adjoining dining area opens to a private deck, while the comfortable living room is anchored by a wood-burning fireplace. Two generously sized bedrooms and an updated full bath with a walk-in shower offer the possibility of convenient main-level living. Upstairs, a private bedroom suite with a full bath and walk-in closet creates an ideal primary retreat, guest suite, or dedicated home office. A skylight above the staircase fills the interior with natural light, and laundry hookups are available on the main level. The expansive unfinished basement offers excellent storage and direct access to the attached one-car garage. Additional guest parking is conveniently located across from the unit, and Artillery Hill residents enjoy access to the community's in-ground pool.

20 Cannon Ridge Dr Unit 20, Watertown
$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
$340,000
3 Beds ⋅ 2 Baths ⋅ 24193146 MLS
Welcome to this well-maintained home in a desirable Watertown neighborhood, offering numerous quality updates and timeless features. Beneath the wall-to-wall carpeting, you'll find hardwood flooring throughout, providing an excellent opportunity to reveal the home's original character. The spacious interior is complemented by central air conditioning, a whole-house fan, and added attic insulation for enhanced year-round comfort and energy efficiency. Major improvements include a new furnace (2024), water heater (2018), New windows installed 2018 throughout , and a roof replaced approximately 8 years ago. Outside, enjoy relaxing or entertaining on the low-maintenance Trex deck overlooking the yard. The driveway was replaced just 3 years ago, adding to the home's curb appeal and long-term value. With strong mechanical updates already completed, this move-in-ready property offers peace of mind while allowing the next owner to add their own personal touches. Conveniently located near schools, parks, shopping, and major commuting routes, this is a wonderful opportunity to own a beautifully cared-for home in Watertown.

78 Westview Dr, Watertown
$369,900
3 Beds ⋅ 2 Baths ⋅ 24194409 MLS
Highest & Best offer deadline is TONIGHT, Sunday (8/2), at 8:00 PM. PRIME WATERTOWN LOCATION ON ALMOST 1 ACRE! Nestled on a private 0.90 acre lot right down the street from Veterans Memorial Park, this 3 bedroom, 1.5 bath Ranch offers a functional layout and unbeatable local convenience. Step inside to a sun drenched living room anchored by a large bay window and gleaming hardwood floors that extend throughout the main level. The heart of the home features a spacious eat in kitchen complete with warm cherry cabinetry, tiled flooring, recessed lighting, and newer stainless steel appliances. Sliders off the kitchen lead directly to an expansive Trex deck overlooking a peaceful backyard, perfect for outdoor entertaining. The main level offers 3 comfortable bedrooms with hardwood floors, including a primary suite with a private half bath, plus a full hall bathroom. Downstairs, the finished walk out lower level delivers versatile bonus space for a family room, home office, or gym, along with a dedicated laundry area, tiled floors, direct access to the attached 2 car garage, and a door leading out to a covered patio. Unmatched Location: Walk to Veterans Memorial Park for sports fields, pavilion, and playground. Enjoy quick access to Crestbrook Park and Golf Course, local schools, shopping, and major routes. Endless potential in a top tier neighborhood!

532 Nova Scotia Hill Rd, Watertown
$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
$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
$399,900
4 Beds ⋅ 4 Baths ⋅ 24188687 MLS
Located in a quiet Watertown, CT neighborhood just minutes from shopping, dining, and major conveniences, this 4-bedroom, 2.5-bath home offers space and flexibility. The upper level features a bright kitchen, dining area, and a spacious family room with skylights that fill the home with natural light, along with three generously sized bedrooms, a full bath, and a half bath in the primary bedroom. The lower level is ideal for an in-law setup, complete with a full kitchen, large living room with fireplace, bedroom, full bath, and private entrance. Outside, enjoy a fenced backyard with a private deck offering plenty of space and privacy. Subject to probate court approval.

15 Monroe St, Watertown
$319,000
3 Beds ⋅ 2 Baths ⋅ 24189088 MLS
BACK ON MARKET AFTER HAVING THE EXTERIOR FRESHLY PAINTED SO Any loan WILL WORK CHFA,FHA,Conv. & more, Move in condition, 4 Level Split Level on Corner Lot, 3 Bedroom, 1 1/2 Bath's, 12x17 Living Room / Dining Room with Hardwood Floors & Electric F/place, Eat-In Kitchen with Granite Countertops & Highend Kitchen Cabinets and Stacked Stone Backsplash & Bamboo Floor,Lower-Level Family Room / Living Room 11x20, 12x12 Rear Deck, home is approximately 1250 ft.2, definitely bigger than Town records show, hard Wood Floors, throughout bedrooms, living room, and hallway,1 Car Garage, Home has solar panels with a very cheap electric bill, A/C Works but has a Freon leak

50 Porter St, Watertown
$399,000
4 Beds ⋅ 2 Baths ⋅ 24187591 MLS
Investors delight! A Prime, downtown located, aesthetically appealing, 1500 sf+, 2 family w/ ample off street parking, just oozing with potential! This 1915 home has stood the test of time and welcomes your finishing touches to restore her luster to generate optimal passive income. Previously utilized as a single family residence, this balanced estate can easily be converted back with minimal investment. Each unit offers a main level eat in kitchen, a generous family room with front porch access, and spacious rear sunroom. Units upper living space adorns 2 commodious bedrooms and full bathrooms. Bring your vision as you convert and transform this home to optimize investment income! This jewel of an investment is ripe for the taking!

77 Westbury Park Rd, Watertown
$390,000
3 Beds ⋅ 2 Baths ⋅ 24186780 MLS
Well-maintained 3-bedroom, 2 full bath home situated on a desirable corner lot. The interior offers a warm, inviting layout with great natural light and a beautifully kept living space. Two pellet stoves provide efficient supplemental heat to help offset winter heating costs. The attached 2-car garage adds convenience and storage. The lower level includes a second kitchen, creating excellent flexibility for in-law or multigenerational living possibilities. A versatile, move in ready home with room for everyone. BEST AND FINAL OFFERS DUE 11:59 PM Tuesday 07/07/2026

127 Eaton St, Watertown
$369,900
4 Beds ⋅ 2 Baths ⋅ 24184144 MLS
Welcome home to this beautiful two-family property located in the heart of Watertown. Sitting on a spacious .66 acre lot, this home offers a perfect blend of comfort, space, and convenience. The first floor features three bedrooms, a full bathroom, a bright living room, a formal dining room, and a well-appointed kitchen-ideal for everyday living or entertaining. Upstairs, the second unit offers three bedrooms, a full bathroom, a cozy living room, a dining area, and a functional kitchen with a walk-in pantry, providing a great layout for extended family or rental income potential. Located just a short walk from Watertown's vibrant downtown, you'll enjoy easy access to local shops, restaurants, parks, and public transportation. Whether you're looking for an investment opportunity or a place to call home, this property has it all.

87 Woodruff Ave, Watertown
$389,000
3 Beds ⋅ 2 Baths ⋅ 24183904 MLS
This well maintained raised ranch located at the end of the culdesac offers privacy and relaxing living in a well established neighborhood. This home offers 3 good size bedrooms with hardwood floors and 2 full baths. Roof is newer and also has central air! The basement offers a mostly complete lower level adding more square footage and could possibly be an inlaw entering thru the garage. This home has a laundry room off the main living floor which could possibly be turned into another bathroom. This home needs some minor updating but new owners could move in and update as they go! A show is a sale! Needs probate approval. More pics Monday

152 Saugus 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
$359,900
3 Beds ⋅ 2 Baths ⋅ 24182796 MLS
REDUCED! Watertown/Oakville Raised Ranch in desirable quiet neighborhood! Property includes a living room with a fireplace, three bedrooms, and one and a half baths. Updated kitchen with stainless steel appliances. Lower level provides a large, finished family room, plus an additional large sunroom and another den/office area. Nice deck leading out to level yard. Efficient propane hot water heat, plus the propane Lupi stove for added comfort and heating. A one-car garage completes this very nice home. New Roof and New skylights just installed on 7/18/26. SUBJECT TO PROBATE APPROVAL! Being Sold AS IS.

38 Highwood Ave, Watertown

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