Homes for Sale near John F. Kennedy High School

• 

  

  

  /27

  $349,000

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft

  26 Oakleaf Dr, Waterbury, CT 06708

  Charming Ranch in the Heart of Town Plot! Don't miss this well-maintained 3-bedroom ranch located in one of Town Plot's most desirable neighborhoods. Step into a spacious eat-in kitchen featuring granite countertops, stainless steel appliances, and tile flooring ideal for everyday living and entertaining. The oversized living room offers plenty of natural light and hardwood floors hidden beneath

  

  Ken Demirs

  Regency Real Estate, LLC

  (203) 580-6683

  26 Oakleaf Dr, Waterbury, CT 06708
• 

  

  

  /40

  $339,999

  • 4 Beds
  • 1 Bath
  • 1,504 Sq Ft

  135 Elise Dr, Waterbury, CT 06708

  Welcome to 135 Elise Dr, a charming, recently remodeled four-bedroom cape on 1.5 acres! Inside you will find a spacious living room, with built in wooden shelving, and two wood burning stoves! A recently updated kitchen features new stainless-steel appliances, and granite counter tops. There is a large sun/bonus room that can be used for entertaining, which leads through glass doors to a giant

  Maria Convertito Regency Real Estate, LLC

  135 Elise Dr, Waterbury, CT 06708
• 

  

  

  /20

  $425,000

  • 4 Beds
  • 3.5 Baths
  • 2,075 Sq Ft

  26 Trowbridge St, Waterbury, CT 06710

  Welcome to 26 Trowbridge Street - a beautifully remodeled Cape Cod-style gem tucked away in a quiet Waterbury neighborhood. This spacious single-family home offers 4 generously sized bedrooms and 3.5 baths, blending classic charm with modern upgrades. Step inside to a warm and inviting main level featuring a sunlit living room, a convenient half bath for guests, a formal dining room perfect for

  Ruth Lara Deane Seer Realty

  26 Trowbridge St, Waterbury, CT 06710
• 

  

  

  /30

  $370,000 Open Sat 2PM - 4PM

  • 3 Beds
  • 3 Baths
  • 1,649 Sq Ft

  27 White Rose Ave, Waterbury, CT 06708

  Location, Location, Location....a well-loved home tucked away in a peaceful desired neighborhood. For eight years, this property has been more than just a house, it's been the heart of countless memories. The street is known for its quiet, neighborly feel, making it the kind of place where you can safely ride bikes, run around, and enjoy the simple joys of being outside. Just minutes from I-84,

  Ashley Henry The Washington Agency

  27 White Rose Ave, Waterbury, CT 06708
• 

  

  

  /38

  $364,900

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  36 Ernest Ave, Waterbury, CT 06708

  Welcome to 36 Ernest Avenue, a well-maintained Colonial built in 2014, located in the sought-after Town Plot neighborhood of Waterbury! This home offers 3 generously sized bedrooms, 1.5 bathrooms, and a bright, open layout perfect for comfortable living. The spacious kitchen features classic oak cabinets, stainless steel appliances, and a sliding glass door that leads directly to a stunning paver

  Emily Fitzgerald William Raveis Real Estate

  36 Ernest Ave, Waterbury, CT 06708
• 

  

  /23

  $350,000

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft

  89 Kelsey St, Waterbury, CT 06706

  Well maintained single family home offering 4 bedrooms and 2 full baths with potential for an in-law set-up on the upper level finished walk-up attic. Laundry hookups in basement and upper level; gas dryer hook-up. Features a covered front porch, large yard on a spacious lot, private driveway and 2 car garage. Conveniently located just minutes from I-84 and Route 8 with easy access to shopping,

  Viviana Rocha Hernandez Fercodini Properties, Inc.

  89 Kelsey St, Waterbury, CT 06706
• 

  

  /24

  $339,900 Open Sat 11AM - 1PM

  • 4 Beds
  • 1 Bath
  • 1,348 Sq Ft

  273 Piedmont St, Waterbury, CT 06706

  Welcome to this beautifully maintained Cape-style home, cherished by the same family for over 41 years. Full of heart and history, this 3-bedroom gem offers a blend of classic character and thoughtful updates that make it truly special. Step onto the inviting covered front porch-perfect for morning coffee or relaxing evenings-and enter a home filled with warmth. Inside, you'll find unique

  Karyn Bedard RE/MAX RISE

  273 Piedmont St, Waterbury, CT 06706
• 

  

  /40

  $327,000

  • 3 Beds
  • 1.5 Baths
  • 1,044 Sq Ft

  839 Washington Avenue Extension, Waterbury, CT 06708

  Welcome to this beautifully updated ranch in the heart of the sought-after Town Plot neighborhood! This move-in-ready gem offers peace of mind with all major mechanicals and big-ticket items replaced from top to bottom - including a new roof, new siding, new furnace, new windows, new water heater, and brand-new gas line to power the economical gas heating system. Step inside to a warm and

  Soraida Valentin-Trotman Showcase Realty, Inc.

  839 Washington Avenue Extension, Waterbury, CT 06708
• 

  

  /21

  $380,000

  • 3 Beds
  • 2 Baths
  • 1,692 Sq Ft

  25 Parkwood Ave, Waterbury, CT 06708

  Welcome home to this beautiful completely renovated raised ranch located on a quiet cul-de-sac in a highly desirable neighborhood. With professionally landscaped immaculate grounds, enjoy the morning tending to your raised garden beds of fresh fruit and vegetables or an evening relaxing by the stone firepit. Entertaining is effortless with a show stopping brand new kitchen and high end

  Devon O'Neill Litchfield Hills Properties LLC

  25 Parkwood Ave, Waterbury, CT 06708
• 

  

  /37

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 2,334 Sq Ft

  864 Baldwin St, Waterbury, CT 06706

  New Construction Colonial - 2,334 SF | Finished Basement | 2.5 Baths | Completed Late 2024 Welcome to this beautifully finished new construction Colonial, built in 2020 and completed at the end of 2024, offering 2,334 sq ft of stylish, modern living with an open floor plan. This home features 3 bedrooms, 2.5 bathrooms, a finished basement ideal for a spacious family room or potential 4th bedroom,

  Chris Marshall YellowBrick Real Estate LLC

  864 Baldwin St, Waterbury, CT 06706
• 

  

  /25

  $335,000

  • 6 Beds
  • 3.5 Baths
  • 3,659 Sq Ft

  103 Buckingham St, Waterbury, CT 06710

  Come view this unique brick Colonial home in Waterbury, located on a scenic lot of land! This home features 6 bedrooms and 3.5 baths complete with a spacious living room and formal dining room with hardwood flooring throughout! Office/playroom can be found off the main living area and has it's own beautiful fire place surround and mantle. Enjoy the convenience of an eat-in kitchen just off the

  Levi Judqin Brass Moon Realty

  103 Buckingham St, Waterbury, CT 06710
• 

  

  /4

  $330,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,384 Sq Ft

  00 Milton Ave, Waterbury, CT 06706

  Seize the unique opportunity to personalize your dream home! This beautiful 1,384 square foot house is currently under construction, allowing you to work directly with the builder to add your personal finishing touches. Featuring three spacious bedrooms and two modern bathrooms, this home includes a cozy living room, an elegant dining room, a modern kitchen with stylish quartz countertops, and a

  Alexander Brooks Showcase Realty, Inc.

  00 Milton Ave, Waterbury, CT 06706
• 

  

  /31

  $334,900 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,812 Sq Ft

  135 Park Terrace, Waterbury, CT 06708

  Step into timeless elegance with this beautiful, 1928 Colonial that seamlessly blends classic character with modern updates. Offering 7 rooms, 3 bedrooms, and 1.5 baths. Enjoy cozy evenings in the large living room with a fireplace, leading to heated sunporch bathed in natural light. The oversized primary bedroom boasts a walk-in closet, while the brand-new kitchen dazzles with quartz countertops

  Vasco Silva Great Estates, CT

  135 Park Terrace, Waterbury, CT 06708
• 

  

  /23

  $275,000

  • 3 Beds
  • 1.5 Baths
  • 1,792 Sq Ft

  508 Congress Ave, Waterbury, CT 06708

  Welcome to this beautiful Colonial brimming with character and opportunity! Nestled on a desirable corner lot, this spacious property features 3 large bedrooms with tall ceilings that create a bright and airy atmosphere throughout. The main level offers a classic layout with a kitchen, living room, and formal dining room - a perfect canvas to create a timeless yet functional space. A charming

  Lysa Napoli Showcase Realty, Inc.

  508 Congress Ave, Waterbury, CT 06708
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  /7

  $20,000

  • Land
  • 0.25 Acre
  • $80,000 per Acre

  0 Hawthorne Ave, Waterbury, CT 06708

  Discover the potential with these two adjacent residential land parcels, totaling approximately .36 acres (.25 acres and .11 acres) being sold together in the sought-after Town Plot neighborhood. These side-by-side, interior lots offer flexibility for one or more new construction homes in a well-established area with strong market appeal. Located close to schools, parks, shopping, and major

  Lisa Novakowski Better Living Realty, LLC

  0 Hawthorne Ave, Waterbury, CT 06708
• 

  

  /17

  $260,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  116 Esther Ave, Waterbury, CT 06708

  Welcome home! Don't miss the opportunity to come see this beautiful home featuring two bedrooms one bathroom. One level living at its finest with a remodeled kitchen and bath. The partially finished basement adds extra living space. Additional features include a one car garage and plenty of functional yard space with two different levels. The yard also includes fencing for privacy and is in a

  Maria Monteiro Regency Real Estate, LLC

  116 Esther Ave, Waterbury, CT 06708
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  /40

  $599,900 Open Sat 2PM - 4PM

  • 8 Beds
  • 3 Baths
  • 3,438 Sq Ft

  220 Hillside Ave, Waterbury, CT 06710

  Welcome to 220 Hillside Avenue, a fully renovated 3-family property offering unmatched value and versatility in the heart of Waterbury. Featuring 8 bedrooms and 3 full bathrooms, this property has been completely renovated from top to bottom, making it ideal for investors or owner-occupants seeking a move-in-ready multi-family opportunity. Renovations include a brand-new roof, updated

  Christopher Germosen King Realty Group LLC

  220 Hillside Ave, Waterbury, CT 06710
• 

  

  /40

  $449,900

  • 6 Beds
  • 3.5 Baths
  • 3,510 Sq Ft

  124 Geddes Terrace, Waterbury, CT 06708

  Location, Location, Location! Attention all investors nows yours chance to own this one of a kind Town Plot Trophy Piece! Nestled in the heart of Town Plot on a dead end road, this oversized fully renovated two-family home is the investment property opportunity or multi-generational living solution you've been waiting for! Perfectly situated on a very private corner lot, this property boasts a

  Patrick Capobianco Dave Jones Realty, LLC

  124 Geddes Terrace, Waterbury, CT 06708
• 

  

  /37

  $318,999

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  50 Norman St, Waterbury, CT 06708

  They say homes can't talk... but I have a story to tell. "I'm not just renovated. I've been reimagined-elegantly, inside and out." Hi, my name is Norma. I've just had a glow-up and let me tell you, I'm feeling brand new from the inside out. With a brand-new roof, fresh interior and exterior paint, sparkling new windows, and a fully renovated kitchen with sleek granite countertops, I'm more

  Diogenes Espinal Coste eRealty Advisors, Inc.

  50 Norman St, Waterbury, CT 06708
• 

  

  /7

  $239,999

  • 3 Beds
  • 2 Baths
  • 1,086 Sq Ft

  26 Highview St, Waterbury, CT 06708

  Cape Cod house 3 BED 2 BATH and garage! Come in and make this lovely home your own! Perfect starter home! OH 7/12/25

  Dillon Cass eRealty Advisors, Inc.

  26 Highview St, Waterbury, CT 06708
• 

  

  /40

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,114 Sq Ft

  141 Joshua Town Rd, Waterbury, CT 06708

  New Construction - Country Club Estates 2114 SQ Ft Raised Ranch - On a Cul De Sac - Abuts Country Club - Spacious open-concept floor plan, highlighted by gleaming hardwood floors, abundant natural light, Seasonal Views and sophisticated finishes throughout. The chef's kitchen featuring custom cabinetry, quartz countertops, a large center island, and GE Cafe Series Connected Appliance - 5 Burner

  Robert Ghent Ghent Realty Advisors

  141 Joshua Town Rd, Waterbury, CT 06708
• 

  

  /15

  $224,500

  • 2 Beds
  • 1.5 Baths
  • 1,288 Sq Ft

  827 Oronoke Rd Unit 5-6, Waterbury, CT 06708

  Welcome to 827 Oronoke Rd Unit 5-6, Waterbury, CT! This beautifully renovated 2-bedroom, 1.5-bath townhouse-style condo is move-in ready and full of charm. Step inside to discover gleaming hardwood floors throughout and an open-concept living and dining area, perfect for everyday living and entertaining. Upstairs, you'll find two generously sized bedrooms featuring vaulted ceilings that add an

  Jessica Lopez Our Home Realty Advisors

  827 Oronoke Rd Unit 5-6, Waterbury, CT 06708
• 

  

  /24

  $2,750,000

  • 9 Beds
  • 3 Baths
  • 7,728 Sq Ft

  701 S Main St, Waterbury, CT 06706

  Truly TURN KEY portfolio opportunity with 8% CAP in the South End almost entirely renovated inside and out! The sale consists of 3 adjacent parcels with 6 buildings = 23 apartments and 2 commercial spaces for a total of 25 units. The unit mix is: (6) 4 bed units, (11) 3 bed units and (6) 2 bed units. 5 Bldgs feature separate, and tenant paid utilities - all electric H, HW & cooking. Bldg 701 has

  Amanda Sheehan Oxford Realty

  701 S Main St, Waterbury, CT 06706
• 

  

  /26

  $475,000

  • 8 Beds
  • 3 Baths
  • 2,822 Sq Ft

  69 W Liberty St, Waterbury, CT 06706

  3 Family with all New Pressure treated - Front and Rear Outside Staircases & Decks to all 3 Floors, 3/3/2 Bedrooms, All Floors Rented but on a Month to Month Basis, All Floors can be Higher

  Paul Roger Full Service Realty LLC

  69 W Liberty St, Waterbury, CT 06706
• 

  

  /23

  $299,000

  • 2 Beds
  • 1 Bath
  • 1,020 Sq Ft

  52 Hewey St, Waterbury, CT 06708

  One floor living at it's best with many updates!! This move in ready ranch offers a remodeled eat-in kitchen with granite counters, tiled backsplash and stainless steal appliances. Hardwood and tile flooring throughout. New windows, new roof and gutters, boiler is two years young, condensing unit is 7 years young, newer cement patio and the yard is fenced in too. Schedule a tour today.

  Simonne Corriveau KW Legacy Partners

  52 Hewey St, Waterbury, CT 06708
• 

  

  /33

  $349,900

  • 6 Beds
  • 3 Baths
  • 2,553 Sq Ft

  1007 Highland Ave, Waterbury, CT 06708

  Great Town Plot multifamily. This property features large first floor unit with full kitchen a center island table, living room, full bathroom and two bedrooms. There is a separate in-law apartment off the back with full kitchen, living, bedroom, full bath and separate entrances. The 2nd floor unit is a two-level apartment with eat in kitchen, living room, one bedroom on first floor and two large

  Gary Bonaldi Better Living Realty, LLC

  1007 Highland Ave, Waterbury, CT 06708
• 

  

  /20

  $210,000

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft

  17 Geddes Terrace Unit 2, Waterbury, CT 06708

  Spacious Townhouse Living in the Heart of Town Plot! Welcome to this desirable 2-bedroom, 1.5-bathroom townhouse-style condo offering space, comfort, and convenience across two well-designed levels. The main floor features a bright living room, formal dining area, and an eat-in kitchen-perfect for entertaining. You'll also find a half bath and washer/dryer hookup in the garage for added

  Rashida Forrester KW Legacy Partners

  17 Geddes Terrace Unit 2, Waterbury, CT 06708
• 

  

  /19

  $350,000

  • 4 Beds
  • 2 Baths
  • 1,904 Sq Ft

  56 Vine St, Waterbury, CT 06704

  Welcome to 56 Vine Street, this thoughtfully updated two-family home. This well-maintained property features a total of four bedrooms and two full bathrooms, with each unit offering two spacious bedrooms and one recently renovated bathroom. Both units have been updated with modern kitchens, fresh paint, and new flooring, giving the home a clean, contemporary feel. Whether you're an investor

  Rob Squeglia Sky Realty Group

  56 Vine St, Waterbury, CT 06704
• 

  

  /17

  $312,900

  • 5 Beds
  • 2.5 Baths
  • 1,828 Sq Ft

  18 Morningside Ave, Waterbury, CT 06708

  Welcome to this charming 1,828 sq ft single-family home nestled on a quiet street in the desirable Bunker Hill area. Situated on a generous 0.17-acre lot, this property offers plenty of space both inside and out. The home features 5 bedrooms, 2 full bathrooms, and 1 half bathroom, perfect for a growing family or those who love to entertain. Hardwood floors run throughout the home, adding warmth

  Jaquan Jones RE/MAX Right Choice

  18 Morningside Ave, Waterbury, CT 06708
• 

  

  /6

  $900,000

  • 1 Bed
  • 1 Bath
  • 7,302 Sq Ft

  995 Bank St, Waterbury, CT 06708

  Great opportunity for a value add property in Waterbury's Brooklyn neighborhood. One building with 11 units, all 1 bed/1 bath w/LR. Aluminum siding, asphalt shingle roof and rear porches. Owner pays heat and hot water (central gas; included in rents). Electric is separate and tenant paid. There is parking for 5 cars in back. Rents are way below market offering great upside potential with 9%

  Amanda Sheehan Oxford Realty

  995 Bank St, Waterbury, CT 06708
• 

  

  /16

  $950,000

  • 19 Beds
  • 8 Baths
  • 6,458 Sq Ft

  203 S Leonard St, Waterbury, CT 06708

  Fantastic investment opportunity that's turn key and cash flowing with 10% ROI and upside! This corner building is a total of 9 units with big unit mix featuring (5) 3 bed/1 bath units, (1) 2 bed, 1 bath unit & 3 studios/1 bath units. All units are spacious AND renovated (8/9) with new flooring throughout, updated kitchens (appliances, cabinets, counters, fixtures); updated bathrooms and overall

  Amanda Sheehan Oxford Realty

  203 S Leonard St, Waterbury, CT 06708
• 

  

  /24

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 12,480 Sq Ft

  197 S Leonard St, Waterbury, CT 06708

  Fantastic S End investment opportunity that's turn key with upside. This corner building is a total of 16 units that feature 2 beds, 1 beds and studio units. Many of the units offer a variety of renovations including new flooring, paint, fixtures, kitchen cabinets, counters, appliances and updated bathrooms. The hallways have been recently painted with new flooring as well. All utilities are

  Amanda Sheehan Oxford Realty

  197 S Leonard St, Waterbury, CT 06708
• 

  

  /37

  $920,000

  • 1 Bed
  • 1 Bath
  • 10,401 Sq Ft

  63 Cherry St, Waterbury, CT 06702

  Investors take notice of this package offering 2 adjacent properties with cash flow and big unit mix with a 9% CAP! TOTAL OF 9 UNITS = 8 apartments + 1 large commercial space. 57 Cherry St is a 2-family with two 2 bed/1 bath units - fully occupied. The property has separate & tenant paid utilities. 63 Cherry is a large mixed-use building with six 3 bed/1 bath apartments + 1 large commercial space

  Amanda Sheehan Oxford Realty

  63 Cherry St, Waterbury, CT 06702
• 

  

  /22

  $138,500

  • 1 Bed
  • 1 Bath
  • 610 Sq Ft

  81 Chipman St Unit 6, Waterbury, CT 06708

  Price Reduced! Excellently maintained one bedroom condo with attached garage and walk out balcony with great views. Enjoy the convenience of in unit laundry, off street parking and a garage. Tile and carpet in great condition throughout. Plenty of closet space and well lit rooms. The condo complex is located in the Town Plot neighborhood, walking distance to restaurants, stores, parks and much

  Zachary Pranger Group Realty LLC

  81 Chipman St Unit 6, Waterbury, CT 06708
• 

  

  /35

  $239,999

  • 2 Beds
  • 1.5 Baths
  • 1,330 Sq Ft

  925 Oronoke Rd Unit 36G, Waterbury, CT 06708

  Welcome to this inviting 2-bedroom townhouse located in one of the area's most desirable complexes for layouts and close proximity to two touching towns. The standout feature of this unit is its prime placement within the complex, easy in and out access, offering both privacy and easy access to amenities nearby, with backyard privacy and view. This well-maintained condo features 2 spacious

  Lauren Hill Mark Tavares Realty, LLC

  925 Oronoke Rd Unit 36G, Waterbury, CT 06708
• 

  

  /11

  $239,900

  • 2 Beds
  • 1.5 Baths
  • 1,330 Sq Ft

  925 Oronoke Rd Unit 17F, Waterbury, CT 06708

  Nice 2 bedroom townhouse style condo with garage and finished basement area.

  Jeanine Blanchette Showcase Realty, Inc.

  925 Oronoke Rd Unit 17F, Waterbury, CT 06708
• 

  

  /13

  $165,000

  • 2 Beds
  • 1.5 Baths
  • 988 Sq Ft

  35 Pearl Lake Rd Unit B, Waterbury, CT 06706

  Best Value - 2 Bed - 1 1/2 Bath condominium unit built in 1989 - Appliances include Electric Range, Refrigerator, Dishwasher - Parking area and drives recently paved - Full Depth Garage provide adequate space for car, storage & Laundry - property conveys subject to and together with any special assessment balances levied by association Sound entry level condo or investment opportunity

  Robert Ghent Ghent Realty Advisors

  35 Pearl Lake Rd Unit B, Waterbury, CT 06706
• 

  

  /11

  $395,000

  • 5 Beds
  • 3 Baths
  • 2,010 Sq Ft

  54 Morningside Ave, Waterbury, CT 06708

  BUNKER HILL 2 FAMILY TOTALLY RENOVATED IN 2017- 1ST FLOOR APT HAS 4 ROOMS, 2 BEDROOMS, 1 BATH & A GAS HOT WATER BOILER FOR HEAT- 2ND & 3RD FLOOR APT HAS 6 ROOMS, 3 BEDROOMS, 2 FULL BATHS & ELECTRIC HEAT- NEW ROOF IN 2017- NEWER ELECTRIC SERVICE- 1 CAR DET GARAGE- PLENTY OF OFF STREET PARKING

  Michael Vitale Vitale Realty

  54 Morningside Ave, Waterbury, CT 06708
• 

  

  /8

  $849,000

  • 10 Beds
  • 5 Baths
  • 4,800 Sq Ft

  227 Hillside Ave, Waterbury, CT 06710

  Prime 6-Family Investment Property - 227 Hillside Ave, Waterbury, CT A fantastic opportunity for investors! This fully renovated 6-family property features all 2-bedroom units, each updated for modern living and designed for long-term tenant retention. Located in a convenient and accessible area of Waterbury, this turn-key asset offers strong rental potential and minimal maintenance demands.

  Alban Dedvukaj Lakeshore Realty

  227 Hillside Ave, Waterbury, CT 06710
• 

  

  /40

  $425,000

  • 7 Beds
  • 3 Baths
  • 3,823 Sq Ft

  108 Highland Ave, Waterbury, CT 06708

  TURN-KEY TRIPLEX WITH VALUE-ADD POTENTIAL: 108-110 Highland Ave is a 3800sqft+ three-family in Waterbury's Town Plot that deposits cash today and leaves room to grow. Units 1 & 3 (2 BR/1 BA) bring in $1,150 and $1,050 per month, while the second-floor flat is VACANT and just remodeled-new paint, luxury-vinyl plank flooring, stainless appliances, updated lighting/fixtures, plus freshly painted

  Mustafa Muaremi Regency Real Estate, LLC

  108 Highland Ave, Waterbury, CT 06708

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