Homes for Sale near Capital Prep Harbor Upper School

• 

  

  

  /23

  $1,575,000

  • 5 Beds
  • 3.5 Baths
  • 3,596 Sq Ft

  35 S Benson Commons, Fairfield, CT 06824

  Nestled on a quiet cul-de-sac just minutes from town, train, and beach, this beautifully crafted Colonial offers the perfect blend of elegance, comfort, and convenience. A charming front porch welcomes you into a light-filled home featuring a dramatic two-story foyer, a chef's kitchen, granite countertops, and premium Viking, Wolf, and Sub-Zero stainless steel appliances. The adjoining family

  Katie O'Grady Compass Connecticut, LLC

  35 S Benson Commons, Fairfield, CT 06824
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• 

  

  

  /20

  $550,000

  • 8 Beds
  • 3 Baths
  • 2,679 Sq Ft

  18-20 Clinton Ave, Bridgeport, CT 06605

  This very large 2,679 sqft 2 family property is perfect for any home owner or investor. The 1st floor unit consists of 3 bedrooms and 1 bathroom. The 2nd unit is a very spacious two floor apartment that has 5 bedrooms and 2 bathrooms that was recently updated. Conveniently located just minutes from I-95 and I-91. Schedule your showing today!!!

  Thomas Payne Century 21 Scala Group

  18-20 Clinton Ave, Bridgeport, CT 06605
• 

  

  

  /25

  $2,899,999

  • 14 Beds
  • 13 Baths
  • 9,590 Sq Ft

  1795 North Ave, Bridgeport, CT 06604

  Baldwin Pearson & Co, Inc. is pleased to present 1795 North Avenue, Bridgeport, CT, an exceptional opportunity to acquire a turnkey multifamily asset in one of Fairfield County's strongest rental markets. This impressive brick apartment building consists of 15 fully renovated residential units and offers investors a stable, low-maintenance income-producing property with significant long-term

  Daniel Shawah Baldwin Pearson & Co., Inc

  1795 North Ave, Bridgeport, CT 06604
• 

  

  

  /11

  $699,900

  $89K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,195 Sq Ft

  225 Winnepoge Dr, Fairfield, CT 06825

  Endless opportunities clean up, move in, expand or build your new dream house. Lake Hills Association...enjoy all the beautiful beaches, kayaking, swimming, etc.

  Stacey DiDio Coldwell Banker Realty

  225 Winnepoge Dr, Fairfield, CT 06825
• 

  

  

  /32

  $1,999,900

  $250K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,381 Sq Ft

  125 Battery Park Dr, Bridgeport, CT 06605

  Perched on a quiet cul-de-sac, this exceptional home offers breathtaking 220-degree panoramic views of Long Island Sound, Black Rock Harbor, and Fayerweather lighthouse. Designed for effortless main-level living, the residence captures stunning water views from the living room, dining room, and luxurious primary bedroom suite. The remodeled primary bath features elegant marble flooring with

  Gail Robinson William Raveis Real Estate

  125 Battery Park Dr, Bridgeport, CT 06605
• 

  

  /39

  $749,900

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,754 Sq Ft

  4386 Main St, Stratford, CT 06614

  Spoil yourself! Move right into this beautifully renovated 3-bedroom, 2.5-bath expanded Cape located in Stratford's desirable Mill River neighborhood! This move-in-ready home offers the perfect blend of comfort, style and convenience. The main level features a stunning designer kitchen with a center island, double ovens, stainless steel appliances, and a new gas range. The kitchen flows

  Jill Taylor RE/MAX Right Choice

  4386 Main St, Stratford, CT 06614
• 

  /2

  $950,000

  • 6 Beds
  • 6 Baths
  • 5,304 Sq Ft

  50 Carleton Ave, Bridgeport, CT 06604

  On the market for the first time in nearly 20 years. This legal 6 family is a cash cow with loads of growth potential. Each unit boasts a living room, dining room, eat-in-kitchen, one bedroom and a full bathroom. There is potential to convert each unit into a two bedroom. The property is currently fully occupied, so new owners will have immediate cash flow. The long standing tenants are currently

  Thomas Chanaca Chanaca Real Estate

  50 Carleton Ave, Bridgeport, CT 06604
• 

  /2

  $699,000

  • Land
  • 16,117 Sq Ft
  • $1,889,189 per Acre

  1 Battery Park Dr, Bridgeport, CT 06605

  Welcome to an exceptional opportunity in the highly sought after enclave at Black Rock! Nestled on a .37 acre lot this parcel boasts unparrelled vistas of the majestic Long Island Sound a canvas for your visionary masterpiece. This prime location beckons investors and builders alike to sieze the potential of coastal living at its finest. Edmbrace the allur of seaside living and capitalize on this

  Steven Koleno Beycome of Connecticut

  1 Battery Park Dr, Bridgeport, CT 06605
• 

  

  /9

  $575,000

  $25K PRICE DROP

  • 8 Beds
  • 3 Baths
  • 3,328 Sq Ft

  464-466 Wilmot Ave, Bridgeport, CT 06607

  Very nice over-sized remodeled two family with finish upper story for added potential. Off Street parking-turnkey, a must see!!!

  Komica Coote-Burwell Coote & Burwell Realty,LLC

  464-466 Wilmot Ave, Bridgeport, CT 06607
• 

  

  /32

  $679,000

  • 3 Beds
  • 2.5 Baths
  • 1,600 Sq Ft

  181 Eastern Pkwy, Milford, CT 06460

  In Milford's coveted Rivercliff neighborhood With serene water views, this stunning home has been masterfully transformed AND EXPANDED from the studs out by Walk Invest, LLC - A premier residential renovation firm with 20+ years of experience and 40+ completed high-end renovations statewide. Their signature is total transformation, and this home is no exception. A reimagined floor plan with

  Lauren Auresto BHGRE Gaetano Marra Homes

  181 Eastern Pkwy, Milford, CT 06460
• 

  

  /19

  $550,000

  • 4 Beds
  • 2 Baths
  • 1,884 Sq Ft

  96 Allencrest Dr, Stratford, CT 06614

  This is beautiful 4 bedrooms 2 full bathrooms Cape in a sought after "Nichols" section of Stratford. This house has many unique property features which includes, huge primary bedroom, bedroom #2 and a full bath on the main level. The main level also has hardwood floor throughout, a fireplace in the living room, huge kitchen/dining, breezeway, a 1 car garage, hardwire security system and active

  Donald Ormsby LIONHEART REALTY & MGMT LLC

  96 Allencrest Dr, Stratford, CT 06614
• 

  

  /12

  $669,900

  • 8 Beds
  • 3 Baths
  • 3,073 Sq Ft

  1179 Noble Ave Unit 1181, Bridgeport, CT 06608

  Beautiful home ready for its new owners. Boasting new roof and vinyl siding. Large units with modern kitchens and baths. Hardwood floors throughout. Gas heat. Thermopane windows. Private yard with garage. Convenient to train, shopping, and all major highways. Value add in bringing rents up to market. Perfect for investor or owner occupant. Field card lists as 3f, do your own due diligence. Can be

  Basil Amso RE/MAX Right Choice

  1179 Noble Ave Unit 1181, Bridgeport, CT 06608
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  /32

  $449,900

  $10K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,454 Sq Ft

  53 Raycroft St, Milford, CT 06461

  Here's your opportunity to move into Milford's desired Naugatuck Gardens Neighborhood! Fall in love with this charming light filled 1454 sqft cape with relaxing covered front porch or living room with the fireplace. This home features hardwood floors throughout the dining room, living room, and two first floor bedrooms with a full bath, a full walk out basement with extra freezer, and central

  Debra McGinley Coldwell Banker Realty

  53 Raycroft St, Milford, CT 06461
• 

  

  /5

  $369,900

  Coming Soon

  • 2 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  41 Calderwood Ct, Bridgeport, CT 06605

  Location, Location, Location! Great opportunity to live just steps to Seabright Beach on Black Rock Harbor and Long Island Sound. This affordable two bedroom, 1.5 bathroom half duplex with a finished lower level family room is located between Captain's Cove Seaport, Fayerweather Yacht Club, Port 5 Naval Veterans Club, S.S. Norden Club and the Black Rock Yacht Club, a boater's paradise. Enjoy the

  John Kleps Berkshire Hathaway NE Prop.

  41 Calderwood Ct, Bridgeport, CT 06605
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  /40

  $995,000

  $405K PRICE DROP

  • 7 Beds
  • 3.5 Baths
  • 4,987 Sq Ft

  65 Arrowwood Place, Stratford, CT 06614

  Exceptional end of cul-de-sac private North Stratford oasis tucked away on 1.6 acres. Home has been lovingly cared for by the original owners and offers an expansive 4,987 square feet, fourteen rooms, seven bedrooms, three and one half baths and three car garage. All generously sized rooms with thoughtfully designed living spaces that offer flexibility for extended families, accommodations for

  Michael Henetz William Raveis Real Estate

  65 Arrowwood Place, Stratford, CT 06614
• 

  

  /13

  $950,000

  New Construction

  • 10 Beds
  • 4 Baths
  • 2,830 Sq Ft

  391 Coleman St, Bridgeport, CT 06604

  Welcome to 391 Coleman Street-an exceptional, fully updated multifamily opportunity in the heart of Bridgeport. This beautifully reimagined property offers modern living, thoughtful design, and outstanding versatility for both owner-occupants and investors alike. Inside, you'll find bright, open-concept layouts featuring stylish new kitchens with crisp white cabinetry, sleek countertops, and

  Alexia Andrade US Asset Realty

  391 Coleman St, Bridgeport, CT 06604
• 

  

  /40

  $699,900

  • 4 Beds
  • 2.5 Baths
  • 2,744 Sq Ft

  200 Captains Walk, Stratford, CT 06614

  Welcome to 200 Captains Walk, tucked away at the end of a quiet cul-de-sac in the sought-after Captain's Walk community, just steps from the scenic Housatonic River. Surrounded by nature yet minutes from shopping, Metro-North, and major highways, this location offers the perfect balance of serenity and commuter convenience. This beautiful center-hall Colonial offers 2,280 SQFT of above-grade

  Gina Williams Preston Gray Real Estate

  200 Captains Walk, Stratford, CT 06614
• 

  

  /15

  $240,000

  • 1 Bed
  • 1 Bath
  • 836 Sq Ft

  155 Short Beach Rd Unit 102, Stratford, CT 06615

  Welcome to this perfectly-located condo in Stratford's desirable Lordship neighborhood, offering the perfect blend of coastal living and everyday convenience. Situated just moments from Short Beach and alongside a scenic golf course, residents enjoy a peaceful setting with easy access to outdoor recreation, walks along the beach, sunrise and sunsets! Enjoy nearby waterfront dining, marinas, and

  Lisa Nuzzo RE/MAX Heritage

  155 Short Beach Rd Unit 102, Stratford, CT 06615
• 

  

  /40

  $1,000,000

  • 7 Beds
  • 5 Baths
  • 7,715 Sq Ft

  1365 E Main St, Bridgeport, CT 06608

  Prime Mixed-Use Investment Opportunity in Bridgeport's East End. Investors take notice! Do not miss this exceptional income-generating opportunity located in the heart of the East End. This versatile mixed-use property offers immediate multi-stream revenue potential, featuring three residential apartments, a commercial storefront, and a detached 3-car garage capable of generating additional

  Brethela Love J & S Realty Services, LLC

  1365 E Main St, Bridgeport, CT 06608
• 

  

  /40

  $599,990

  • 5 Beds
  • 2 Baths
  • 1,652 Sq Ft

  75 Commercial St, Bridgeport, CT 06604

  Welcome to 75 Commercial st. This fully remodeled two-family property offering excellent updates, comfortable living spaces, and strong investment potential. Both units have been renovated from top to bottom and feature new flooring, updated kitchens with brand-new appliances and quartz countertops, and beautifully remodeled bathrooms. Major improvements include a new roof, new water heaters, and

  Alvaro Tomas Baptista Ki Property Group

  75 Commercial St, Bridgeport, CT 06604
• 

  

  /22

  $625,000

  • 3 Beds
  • 1 Bath
  • 1,075 Sq Ft

  439 Stillson Rd, Fairfield, CT 06824

  Ideally situated in a highly convenient location, this home offers easy access to shopping, dining, schools, parks, transportation and everyday essentials within easy reach. Enjoy the ideal balance of comfort and accessibility, with everything you need just moments from your front door. This home has an open floor plan that connects the kitchen to the dining area with an easy entrance from the

  Rima Bishuti William Raveis Real Estate

  439 Stillson Rd, Fairfield, CT 06824
• 

  

  /16

  $149,000

  $20K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 604 Sq Ft

  2370 North Ave Unit 4C, Bridgeport, CT 06604

  Welcome to The Regency, where comfort, simplicity, and convenience come together in Bridgeport's desirable Brooklawn neighborhood. This bright and well-maintained one-bedroom condo offers an easy, low-maintenance lifestyle with a layout that feels open and inviting from the moment you step inside. Natural light fills the spacious living and dining area, complemented by hardwood floors and a

  Shane Mason-Fryer KW Legacy Partners

  2370 North Ave Unit 4C, Bridgeport, CT 06604
• 

  

  /35

  $315,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  2625 Park Ave Unit 11P, Bridgeport, CT 06604

  New to the Market. Rarely available, south facing 11th floor end unit. This two bedroom, two bath home offers 1128 sf of living space plus a 13x6 balcony with unobstructed spectacular views to Long Island Sound and beyond. This light filled unit is best described as part mid-century, part traditional. The sellers pride of ownership is obvious with all the remodeling completed. The kitchen offers

  Richard Henrietta William Raveis Real Estate

  2625 Park Ave Unit 11P, Bridgeport, CT 06604
• 

  

  /16

  $490,000

  • 3 Beds
  • 1.5 Baths
  • 2,030 Sq Ft

  26 Marsdale Ave, Bridgeport, CT 06606

  This beautiful colonial offers timeless charm with comfortable living spaces. Inside you will find a spacious living room a formal dining room and an eat in kitchen. Three generously sized bedrooms with hardwood floors, natural light and warmth throughout. Schedule your showing today.

  Colette Daye-Hall Century 21 AllPoints Realty

  26 Marsdale Ave, Bridgeport, CT 06606
• 

  

  /39

  $1,548,000

  • 4 Beds
  • 2.5 Baths
  • 3,665 Sq Ft

  485 Mountain Laurel Rd, Fairfield, CT 06824

  Picture coming home to your own Custom Colonial sitting on over half a private acre on a quiet, tree-lined street in lower Greenfield Hill, where you're minutes from everything but feel worlds away. An expansive front porch invites you to slow down the second you pull in. Inside, sunlight pours through every room and hardwood floors gleam underfoot. The high-end, spacious kitchen is made for

  Patricia Shea Coldwell Banker Realty

  485 Mountain Laurel Rd, Fairfield, CT 06824
• 

  /2

  $385,000

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  1109 Elm St, Stratford, CT 06615

  LOCATION! Perfectly situated in one of Stratford's most covenient locations, this 3-bedroom ranch is just minutes from everything. Enjoy being only a 5 minute drive to Short Beach, offering a playground, restaurant, golf course, basketball courts, and recreation area while the Stratford train station (Metro North) is just 5 minutes in the other direction for easy access to New York City. This

  Jocelyn Loukas Coldwell Banker Realty

  1109 Elm St, Stratford, CT 06615
• 

  

  /38

  $499,500

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,205 Sq Ft

  44 Wood Ave, Milford, CT 06460

  Coastal cottage charm with NO FLOOD INSURANCE awaits it's new steward! Welcome to this sweet beachy bungalow, nestled in one of Milford's most sought after coastal communities - Walnut & Windermere Beach. Enter through the open living & dining area, accented with custom built-in dry bar. This flows to the sunny kitchen with granite countertops, the most perfect breakfast nook, and full tile

  Melanie Gunn Coldwell Banker Realty

  44 Wood Ave, Milford, CT 06460
• 

  

  /13

  $170,000

  • 3 Beds
  • 1 Bath
  • 1,016 Sq Ft

  70 Fisher Ct, Stratford, CT 06614

  Tucked away on a cul-de-sac a three bedroom duplex with living spaces bathed in natural light, creating an airy, uplifting atmosphere that follows you from room to room. Large fenced yard with two connecting sheds perfect for summer barbecues or crisp autumn evenings under the stars. Convenient location with access to major commuter routes and the train station. This home is ready for its next

  Eveline Carvotta Compass Connecticut, LLC

  70 Fisher Ct, Stratford, CT 06614
• 

  

  /35

  $239,900

  • 1 Bed
  • 2 Baths
  • 1,131 Sq Ft

  2625 Park Ave Unit 14J, Bridgeport, CT 06604

  Whether you're looking for a rental alternative, downsizing, or just wish to add to your real estate investment portfolio in a convenient and safe location, then look no further. This is a rare opportunity to own a 'J' unit ,of which only 5 have gone to market in the last five years. These units are the largest in the building, with an abundance of closet/storage space. 14-J offers 2 full

  Robert Ganim RE/MAX Heritage

  2625 Park Ave Unit 14J, Bridgeport, CT 06604
• 

  

  /25

  $649,900

  $22K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  245 Unquowa Rd Unit 44, Fairfield, CT 06824

  Welcome to Mosswood condominiums: A must see updated second floor residence in this Fairfield sought-after well maintained complex. Perfectly located within walking distance to train and area restaurants. Interior was just repainted. Beautifully updated, renovated kitchen and two full bathrooms. New window treatments and lighting. Impeccably maintained. Large rear deck overlooking courtyard.

  Ed Pinto The Pinto Group R. E. Services

  245 Unquowa Rd Unit 44, Fairfield, CT 06824
• 

  

  /40

  $515,000

  • 5 Beds
  • 3 Baths
  • 2,313 Sq Ft

  644-646 Maple St, Bridgeport, CT 06608

  Discover an exceptional investment opportunity with this well-maintained 3-family property in the heart of Bridgeport. Built in 1892, this spacious multi-family home offers 2,313 square feet of living space with a total of 5 bedrooms and 3 full bathrooms across three separate units, providing flexibility for owner-occupants or investors seeking strong rental potential. Each unit features

  Ryan McEachern William Raveis Real Estate

  644-646 Maple St, Bridgeport, CT 06608
• 

  

  /40

  $1,699,000

  $1M PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 4,643 Sq Ft

  5060 Main St, Stratford, CT 06614

  Welcome to this stunning waterfront retreat on the scenic Housatonic River, offering panoramic views, luxury, and comfort. Perfect for relaxing or entertaining, this home features 3 spacious bedrooms, 3.5 baths, and a finish able bonus room above the 2-car garage-ideal for a guest suite or office. Elevator to all three levels provides added convenience. A stone wall and gated entry lead to a

  Karen Cross William Raveis Real Estate

  5060 Main St, Stratford, CT 06614
• 

  

  /30

  $749,000

  • 4 Beds
  • 3 Baths
  • 1,992 Sq Ft

  12 Cottage Place, Trumbull, CT 06611

  Set on a peaceful cul-de-sac, in Trumbull, this beautifully renovated 4-bedroom, 3-bath Cape Cod home combines timeless charm with stylish, custom updates throughout its 1,992 square feet of living space. This home features high end finishes, hardwood floors, recessed lighting, fresh paint, and skylights throughout. As you step inside, you're greeted by a striking stone tile accent wall with open

  Sara Fowler Coldwell Banker Realty

  12 Cottage Place, Trumbull, CT 06611
• 

  

  /38

  $1,200,000

  • 12 Beds
  • 6 Baths
  • 4,500 Sq Ft

  626 Stillman St, Bridgeport, CT 06608

  An amazing investment opportunity with great upside! Get ready to invest and make money. A modern 6-unit building built in 1989 and fully occupied on a month-to-month basis, situated across a charter school and close to a public school on the East Side of Bridgeport, off Pembroke Street near Boston Avenue. Can easily gross over $100K annually. The roof was replaced in 2020. The property has vinyl

  Patricia Anekwe YellowBrick Real Estate LLC

  626 Stillman St, Bridgeport, CT 06608
• 

  

  /30

  $330,000

  $19K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,620 Sq Ft

  134 Ogden St, Bridgeport, CT 06608

  Welcome to 134 Ogden Street, a charming Colonial-style home located in Bridgeport's East End. This property features spacious living across multiple levels, a bright living room, hardwood flooring, recessed lighting, an eat-in kitchen, and a functional layout with comfortable bedroom space and multiple bathrooms. Conveniently located near local shops, restaurants, public transportation, I-95,

  Oswaldo Torres Las Americas Real Estate

  134 Ogden St, Bridgeport, CT 06608
• 

  

  /7

  $849,900

  • 5 Beds
  • 5.5 Baths
  • 4,219 Sq Ft

  145 Dewey St, Stratford, CT 06615

  Welcome to this exceptional single-family residence in Stratford, CT, offering 3,219 square feet of living space with 5 bedrooms and 5.5 bathrooms. Extensively renovated and rebuilt in 2011, this remarkable home showcases superior craftsmanship, timeless character, and extraordinary custom stonework throughout. The exterior is truly one of a kind, featuring Natural Desert Creek stone veneer

  Rosania Melo Rosana Melo Realty

  145 Dewey St, Stratford, CT 06615
• 

  

  /37

  $699,999

  • 4 Beds
  • 2.5 Baths
  • 2,797 Sq Ft

  6 Norwood Terrace, Trumbull, CT 06611

  HIGHEST & BEST OFFERS DUE TUESDAY 8/11 @ 1:00PM. Modern living meets unbeatable convenience in this open-concept ranch. Set on a street that backs up to the Pequonnock River Valley Trail, you'll enjoy the rare luxury of being a short stroll to Trumbull Center yet close to beloved Trumbull parks. A stone front porch and sky-blue door welcomes you in, where a spacious great room offers endless

  Sarah Pritchard William Raveis Real Estate

  6 Norwood Terrace, Trumbull, CT 06611
• 

  /2

  $620,000

  • 6 Beds
  • 2 Baths
  • 3,558 Sq Ft

  695 Beechwood Ave, Bridgeport, CT 06605

  Welcome to 695 Beechwood Avenue, an exceptional multi-family property offering outstanding income potential and incredible flexibility. Whether you're an investor looking to expand your portfolio or an owner-occupant seeking to offset your mortgage with rental income, this property is a fantastic opportunity. Currently configured as three units, this property features separate utilities, making

  imelda isles eXp Realty

  695 Beechwood Ave, Bridgeport, CT 06605
• 

  

  /24

  $495,000

  $4K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 3,108 Sq Ft

  185 Grandview Ave, Bridgeport, CT 06606

  Welcome home to this spacious and beautifully maintained single-family colonial located in the North End of Bridgeport. This home features six bedrooms and two full bathrooms with an updated Kitchen newer stainless steal appliance's and tons of storage. With its expansive layout, this property offers endless possibilities to make it your own. You'll find a detached two-car garage providing

  Carolyn Colon-Ortega Century 21 Scala Group

  185 Grandview Ave, Bridgeport, CT 06606
• 

  

  /11

  $280,000

  • 2 Beds
  • 1.5 Baths
  • 1,500 Sq Ft

  3370 Madison Ave Unit 2B, Bridgeport, CT 06606

  Discover the perfect combination of space, comfort, and convenience in this beautifully maintained 2-bedroom, 1.5-bath townhouse offering approximately 1,500 square feet of living space. Ideally situated on Madison Avenue, this desirable residence features a spacious and inviting layout with generously sized rooms, abundant natural light, and plenty of storage throughout. Enjoy a prime location

  Kristen Heinrich BHGRE Gaetano Marra Homes

  3370 Madison Ave Unit 2B, Bridgeport, CT 06606

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