Middlesex County CT Homes for Sale

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  /10

  $365,000

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  8 Prospect Hill, Deep River, CT 06417

  This home possesses structural integrity and endless potential. Many updates including new boiler in 2024, roof, garage doors front and back, new appliances include sink and countertop. Originally had a 3rd bedroom and wall could be put back up if interested in adding back. Short walking distance to charming downtown Deep River and 3/4 mile to the gorgeous CT river. Only 2 hours from NYC. Whether

  Craig Milton Re/Max Valley Shore

  8 Prospect Hill, Deep River, CT 06417
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  /39

  $395,000

  • 9 Beds
  • 3 Baths
  • 3,906 Sq Ft

  259 Pearl St, Middletown, CT 06457

  Great investment opportunity with added flexibility for an owner occupant. This clean and well maintained three unit multi family offers three similar updated layouts, each with 3 bedrooms, a spacious eat in kitchen with pantry, and a large living room that gives every unit a comfortable, functional feel. Two units are currently rented, while the second floor is vacant, creating an ideal setup

  Mike Rethis Coldwell Banker Realty

  259 Pearl St, Middletown, CT 06457
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  /40

  $449,900

  • 4 Beds
  • 2 Baths
  • 1,771 Sq Ft

  4 Robin Ln, Clinton, CT 06413

  Perfectly positioned just moments from Clinton's shoreline, this expanded 4-bedroom, 2-bath Cape offers a compelling blend of space, updates, and coastal setting. Set on a level, usable lot with glimpses of the surrounding marsh, the property delivers both privacy and proximity to beaches, marinas, and town amenities. Inside, the home features a thoughtfully designed layout anchored by a

  

  Dylan Walter

  William Raveis Real Estate

  (860) 743-0566

  4 Robin Ln, Clinton, CT 06413
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  /21

  $375,000

  • 5 Beds
  • 2 Baths
  • 2,243 Sq Ft

  121 Saybrook Rd, Middletown, CT 06457

  Come see this two family investment property in the heart of Middletown, offering over 2,200 sq. ft. of living space. Each unit is thoughtfully laid out and provides comfortable, functional living. The first floor unit features three bedrooms, a full bathroom, and spacious living and dining areas. The second-floor unit offers two bedrooms, one full bathroom, and access to a full walk-up attic

  Michael Reiman William Raveis Real Estate

  121 Saybrook Rd, Middletown, CT 06457
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  /38

  $6,600,000

  • 6 Beds
  • 4 Baths
  • 5,739 Sq Ft

  11 River Edge Rd, Old Saybrook, CT 06475

  Riverside Elegance Meets Neoclassical Grandeur: Experience the pinnacle of waterfront living in this breathtaking Grecian Colonial estate, perfectly situated on 3.43 pristine acres overlooking the majestic Connecticut River. Spanning an impressive 5,739 square feet, this residence combines timeless architectural sophistication with the serene beauty of nature. Leave the world behind as you travel

  Colette Harron William Pitt Sotheby's Int'l

  11 River Edge Rd, Old Saybrook, CT 06475
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  /38

  $434,900

  • 5 Beds
  • 3 Baths
  • 1,644 Sq Ft

  207 Timber Ridge Rd, Middletown, CT 06457

  Don't miss this beautiful Cape Cod featuring five bedrooms and three full baths. Well maintained and thoughtfully updated, this home has seen many renovations over the past three years and is filled with natural light throughout. The main floor offers two bedrooms, a comfortable living room, and a welcoming kitchen perfect for everyday cooking and gathering. The kitchen opens to a large deck,

  Himanshu Singh Singh Realty

  207 Timber Ridge Rd, Middletown, CT 06457
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  /40

  $2,800,000

  • 5 Beds
  • 5.5 Baths
  • 5,234 Sq Ft

  88 Main St, Ivoryton, CT 06442

  Move into this elegantly designed, meticulously restored estate in the nationally registered historic village of Ivoryton in the town of Essex. Built by the prominent Essex industrialist, Samuel Comstock, the 5,234 sq. ft. property on 1.86 acres offers history and grandeur to those seeking privacy and tasteful opulence. Preserved in the same family for five generations and recently completely

  Kirsten Adams William Pitt Sotheby's Int'l

  88 Main St, Ivoryton, CT 06442
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  /32

  $389,900

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  32 Porges Rd, East Haddam, CT 06423

  Inviting, totally updated colonial with CT River views. Serene location yet near everything! Practically walk to Goodspeed Opera house and restaurants. Miles of CT River to explore. Charming interior in this 3 bedroom home. Primary bedroom holds a king sized bed and the other 2 bedrooms are spacious as well. Great storage throughout the home and everything arranged for convenience.Updated baths

  Cathleen Hall Berkshire Hathaway NE Prop.

  32 Porges Rd, East Haddam, CT 06423
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  /30

  $419,000

  • 3 Beds
  • 2 Baths
  • 1,281 Sq Ft

  405 Pond Meadow Rd, Westbrook, CT 06498

  Charming Cape is set on a lovely, level lot in a desirable location just minutes from picturesque Westbrook Center and the beautiful shoreline. Inside, you'll find a spacious living and dining room combination featuring a cozy fireplace with wood-burning stove-perfect for relaxing or entertaining. The main level offers the convenience of a first-floor primary bedroom, along with an additional

  

  Cathy Lynch

  Coldwell Banker Realty

  (860) 351-4080

  405 Pond Meadow Rd, Westbrook, CT 06498
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  /26

  $419,900

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  17 Flatbrook Rd, East Hampton, CT 06424

  **HIGHEST AND BEST DUE BY END OF DAY SUNDAY APRIL 12th** Welcome to 17 Flatbrook Road in East Hampton, a 4-bedroom, 2 full bath Cape set on a private 1.6-acre lot. This home offers approximately 1,500 square feet of living space with a flexible layout featuring two bedrooms and a full bath on the first floor, and two additional bedrooms and a full bath on the second floor. The main level includes

  Carl Guild Carl Guild & Associates

  17 Flatbrook Rd, East Hampton, CT 06424
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  /20

  $149,900

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  23 Linden Ave N, Westbrook, CT 06498

  If you've been waiting for something that just feels right, this is it. Welcome to 23 N Linden Ave in one of Westbrook's sought-after 55+ shoreline communities. What makes this home stand out is the enclosed sun porch, a bonus space you don't often see and one you'll actually use every day for coffee, relaxing, or coming back from the beach! Inside offers a bright, open living area with an easy,

  Eliesha Johnson William Raveis Real Estate

  23 Linden Ave N, Westbrook, CT 06498
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  /26

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  15 Barrie Rd, East Hampton, CT 06424

  Enjoy the best of lake house living in this exceptionally well-maintained 3-bed contemporary home in the desirable Brookhaven Park Association of East Hampton. LAKE RIGHTS: Just steps to the private association beach, boat docks and boat launch on Lake Pocotopaug, this home offers the perfect blend of comfort, natural light, and outdoor living. The open-concept living area features vaulted

  Mary Milewski Berkshire Hathaway NE Prop.

  15 Barrie Rd, East Hampton, CT 06424
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  /38

  $219,000

  • 2 Beds
  • 2.5 Baths
  • 1,284 Sq Ft

  124 Skyview Dr, Cromwell, CT 06416

  Fantastic three level condominium waiting to be spruced up. Lower level is a large open family room. The main level has a good size kitchen and dining room /family room with a fireplace and deck. The upper level has two bedrooms both with full baths and a laundry room located in the hallway. Sale is As Is Condition

  Charlie Lilley Century 21 AllPoints Realty

  124 Skyview Dr, Cromwell, CT 06416
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  /26

  $159,900

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  4 Country Squire Dr Unit 4G, Cromwell, CT 06416

  This Cromwell one-bedroom condo has the updates that are hard to find at this price point. The kitchen features granite counters and has been refreshed without being overdone. Newer flooring runs through the living area and ties the space together nicely. A walk-in closet and additional dedicated storage area round out the unit nicely. Two sliders open to two connected patios with a view that

  Beth Diloreto Berkshire Hathaway NE Prop.

  4 Country Squire Dr Unit 4G, Cromwell, CT 06416
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  /35

  $1,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,448 Sq Ft

  18 Little Point St, Essex, CT 06426

  Classic Cape Cod home in Essex Village. Little Point Street leads to the CT River for you to launch your canoe, kayak or paddle board. Gaze out the picture window in the kitchen to river views while you have coffee or dine. First floor primary bedroom has a remodeled ensuite bath, walk-in second closet and storage cabinetry wall. Upper bedroom with balcony deck also has water views. Newer garage

  Louisa Ketron Berkshire Hathaway NE Prop.

  18 Little Point St, Essex, CT 06426
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  /3

  $611,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,349 Sq Ft

  67 Wildwood Ln, Middletown, CT 06457

  Rarely does a home of this caliber become available in the prestigious South Farms district of Middletown. Tucked away at the end of a private cul-de-sac, 67 Wildwood Ln. is a masterpiece of craftsmanship, custom-built by the renowned Jean Gullitti. This exceptional property has been meticulously maintained by its original owners, offering a unique opportunity to own a "one-family" home with a

  Stefania Bramato Berkshire Hathaway NE Prop.

  67 Wildwood Ln, Middletown, CT 06457
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  /2

  $160,000

  • 1 Bed
  • 1.5 Baths
  • 1,037 Sq Ft

  711 Lake Vista Dr Unit 711, East Hampton, CT 06424

  Lake Vista Condo Available! This home is ready for your personal touch and offers incredible potential to build equity. The open concept layout offers a seamless transition from the foyer to the living room and dining area, with sliding doors that lead to a private deck, perfect for enjoying views of the lake. Upstairs, you will find a generously sized primary suite with a full bath, along with a

  

  Sandra Lindstrom

  Carl Guild & Associates

  (860) 415-8648

  711 Lake Vista Dr Unit 711, East Hampton, CT 06424
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  /29

  $469,900

  • 2 Beds
  • 2 Baths
  • 1,252 Sq Ft

  46 Main St, Essex, CT 06426

  Discover the perfect blend of income potential and small-town charm with this centrally located two-unit property. Ideal for investors or owner-occupants seeking rental income, this well-maintained home offers flexibility and walkable convenience in the heart of Centerbrook. First Floor - Private entrance with direct access from the parking area. Freshly painted and flooded with natural light,

  Tracy Lenz William Pitt Sotheby's Int'l

  46 Main St, Essex, CT 06426
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  /40

  $569,900

  • 4 Beds
  • 2.5 Baths
  • 2,916 Sq Ft

  73 Lake Rd, Portland, CT 06480

  A Tranquil New England Retreat w Panoramic Lake & Mountain Views. Nestled on a nearly 1 acre lot. This beautifully remodeled Cape offers a rare blend of rustic charm & modern comfort. Originally built in 1925, rebuilt from the studs in 2008 w premium grade materials, 2,916 sqft of thoughtfully designed living space. It isn't just a house it's a lifestyle. A sanctuary for those seeking peaceful

  Shawnna Kelly SalCal Real Estate Connections

  73 Lake Rd, Portland, CT 06480
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  /25

  $290,000

  • 2 Beds
  • 2 Baths
  • 1,094 Sq Ft

  92 Main St Unit 206, Deep River, CT 06417

  Historic Charm Meets Modern Luxury at The Piano Works building. Once the heart of the 19th-century ivory industry, the iconic Piano Works building-now featured on the National Register of Historic Places is home to this stunning, move-in-ready townhouse. This 2 bedroom, 2-bathroom townhouse condominium perfectly balances industrial heritage with 2025 luxury. Inside, you'll find stunning exposed

  Jill Pilgrim William Pitt Sotheby's Int'l

  92 Main St Unit 206, Deep River, CT 06417
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  /25

  $172,500

  • 1 Bed
  • 1.5 Baths
  • 738 Sq Ft

  111 Dekoven Dr Unit 708, Middletown, CT 06457

  This condo unit will dazzle you! It has been tastefully remodeled with modern conveniences, flooring and kitchen appliances. Sliding glass doors from your living room lead to your private balcony, overlooking the Ct. River with spectacular views all year long. Relax in your outdoor living space and take in the sensational sunsets, breathtaking fall foilage and amazing Four of the July fireworks

  Sally McMahon William Raveis Real Estate

  111 Dekoven Dr Unit 708, Middletown, CT 06457
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  /37

  $588,000

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

  68 Brittany Dr, Durham, CT 06422

  Welcome to this exceptionally well-built home on nearly 4 acres! Tucked at the end of a cul-de-sac, this oversized Cape offers sunny interiors within its 3,000+ sf with 3 bedrooms & 3 full baths. Multiple living areas afford great layout flexibility: family room with fireplace, living room, dining room, eat-in kitchen, sun room, home gym & mudroom. Anchoring these spaces is the large, remodeled

  Claudia O'Connell William Raveis Real Estate

  68 Brittany Dr, Durham, CT 06422
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  /40

  $875,000

  • 3 Beds
  • 3 Baths
  • 2,515 Sq Ft

  16 Parker Terrace, Essex, CT 06426

  Experience the perfect blend of charm and sophistication in this newly remodeled and expanded Cape, offering comfort and convenience in every detail. The home impresses with high-end finishes, including a modern kitchen with European tile flooring, two-tone cabinetry with double pantries, a farm sink, GE Cafe appliances in matte white with bronze accents, and Amish barnwood shelving. Two Primary

  Jay Lafleur William Pitt Sotheby's Int'l

  16 Parker Terrace, Essex, CT 06426
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  /19

  $249,900

  • 2 Beds
  • 1 Bath
  • 1,155 Sq Ft

  280 E Main St Unit B5, Clinton, CT 06413

  Breathe in the ocean air as you take in serene causeway views from the kitchen window of this tastefully remodeled ranch style condo. This spacious 2-bedroom, 1-bath home showcases modern touches throughout. Both the kitchen and bathroom were recently renovated, featuring new flooring, updated lighting, a tiled shower with built-in seat, a quartz topped vanity, and granite kitchen countertops

  Antonella Vertucci William Pitt Sotheby's Int'l

  280 E Main St Unit B5, Clinton, CT 06413
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  /30

  $225,000

  • 2 Beds
  • 2 Baths
  • 1,038 Sq Ft

  111 Dekoven Dr Unit 202, Middletown, CT 06457

  Experience easy one-level living in vibrant downtown Middletown at the desirable Rivers Edge community. This high-rise ranch condominium features 2 bedrooms and 2 full bathrooms, plus the added convenience of a washer and dryer combo right in the unit. The generous living room offers direct access through sliding doors to a private balcony where you can relax and take in scenic views of the

  

  Cheryl Zalewski

  eXp Realty

  (860) 485-7124

  111 Dekoven Dr Unit 202, Middletown, CT 06457
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  /19

  $99,900

  • Land
  • 1 Acre
  • $99,900 per Acre

  0 Turkey Hill Rd, Chester, CT 06412

  Discover the perfect setting to build your dream home in the desirable Wig Hill area of Chester, Connecticut. Located near Cockaponset Sate Forest and the scenic Connecticut River valley. This beautiful one-acre level building lot features approximately 211 feet of road frontage and dimensions of roughly 200 x 200 feet, offering ample space and flexibility to bring your custom plans and ideas to

  Charles Kroopneck Charles Kroopneck Real Estate

  0 Turkey Hill Rd, Chester, CT 06412
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  /24

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,404 Sq Ft

  240 Elm St, Old Saybrook, CT 06475

  Welcome to a home where quality meets comfort, starting with a charming brick walkway and vibrant perennials that lead to an inviting front entrance with a character-filled full dining area. This seamless one-floor layout continues into the eat-in kitchen, which boasts a spacious countertop, and a convenient first-floor laundry room complete with a half bath. Relax in the living room, featuring a

  Sang Jee Eagle Eye Realty PLLC

  240 Elm St, Old Saybrook, CT 06475
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  /30

  $180,000

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft

  21 Mill Pond Ln Unit E, Durham, CT 06422

  Tucked along a quiet stretch of Mill Pond Lane in Durham, this inviting home in a 62+ community offers a blend of privacy, charm, and convenience. Set in a peaceful, natural setting, it provides a relaxed lifestyle while remaining close to local amenities and commuter routes. Inside, the home features a functional layout with bright, comfortable spaces ideal for everyday living and entertaining.

  Christina Bates Coldwell Banker Realty

  21 Mill Pond Ln Unit E, Durham, CT 06422
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  /19

  $1,100,000

  • 8 Beds
  • 4 Baths
  • 5,176 Sq Ft

  0 Portland St, Middletown, CT 06457

  Exceptional Multi-Family Investment Opportunity in CT! Located in desirable Middletown, this unique property package offers two two-family homes-for a total of four income-producing units-along with a versatile 2,898 sq ft workshop and two additional vacant land parcels. Each residential building offers approximately 1,380 sq ft with new roofs, new windows, upgraded electrical, and modernized

  Jamie Smigel Carl Guild & Associates

  0 Portland St, Middletown, CT 06457
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  /39

  $2,250,000

  • 4 Beds
  • 2 Baths
  • 2,678 Sq Ft

  39 Chapman Ave, Westbrook, CT 06498

  A rare opportunity to own a truly special year-round waterfront retreat with its own private sandy beach and breathtaking, unobstructed views of Long Island Sound. Offered for the first time in years, this cherished family home blends timeless beach cottage charm with thoughtful updates for modern coastal living. Spanning approximately 2,700 sq ft, the home features 4 bedrooms and 2 full baths,

  Joel Lucas Coldwell Banker Realty

  39 Chapman Ave, Westbrook, CT 06498
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  /37

  $684,900

  • 3 Beds
  • 2 Baths
  • 2,125 Sq Ft

  70 Cedar Dr, Durham, CT 06422

  Experience the perfect blend of classic New England charm and modern luxury in this meticulously updated 3-bedroom, 2-bathroom Cape, situated on over 12 serene acres in Durham. This property offers a rare "best of both worlds" opportunity: maintain a massive private forest retreat for outdoor enthusiasts, or take advantage of a prepared site plan to subdivide and create an additional buildable

  Luke Florian SSG Real Estate LLC

  70 Cedar Dr, Durham, CT 06422
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  /35

  $339,000

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft

  1 Yellow Wood St, Middletown, CT 06457

  Bright and spacious home with an open floor plan. Features an oversized deck overlooking the yard, along with a paver patio, gardens, and electrical in place for a potential hot tub. The finished lower level offers flexible living space ideal for a family room, recreation area, or home office. Generous garage space provides additional storage. Located in a community offering amenities such as

  Stephen Mele Houlihan Lawrence

  1 Yellow Wood St, Middletown, CT 06457
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  /25

  $1,350,000

  • 3 Beds
  • 3 Baths
  • 2,475 Sq Ft

  6 Leeway Dr, Westbrook, CT 06498

  Pristine year round Contemporary home with views of the Marina at Pilots Point. Relax on the 12'x35' deck with an electric retractable awning or just enjoy the evening setting sun. The back patio has an enclosed shower and an area to grill. This home has been renovated and features many upgrades. The family room on the first floor could have an office. The Great room on the 2nd level has windows

  Salome Kirkutis SKS Realty

  6 Leeway Dr, Westbrook, CT 06498
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  /40

  $799,900

  • 3 Beds
  • 3 Baths
  • 2,407 Sq Ft

  112 Main St, Centerbrook, CT 06409

  Nestled on a prime 0.5-acre corner lot in the heart of Centerbrook, 112 Main Street is a meticulously maintained 3-bedroom home that perfectly blends classic charm with serious modern utility. The residence has been extensively updated, featuring an exterior professionally painted in August 2025 with a three-year guarantee and a refreshed kitchen boasting new countertops and a functional kitchen

  Adam Zak Century 21 Classic Homes

  112 Main St, Centerbrook, CT 06409
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  /37

  $419,900

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

  65 Main St Unit 24, Essex, CT 06426

  Enjoy easy living just steps from the charm of Ivoryton Village in this beautifully maintained 2-bedroom home, 2 full and 1 half bath, offering 1,384 sq ft of bright, inviting space. The main level features an open and airy layout, highlighted by a remodeled eat-in kitchen with sliders leading to a spacious deck, perfect for entertaining or relaxing outdoors. Hardwood flooring flows throughout,

  Craig Milton Re/Max Valley Shore

  65 Main St Unit 24, Essex, CT 06426
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  /30

  $245,000

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  1271 Washington St Unit 4, Middletown, CT 06457

  Beautifully Renovated Townhome in the sought-after Woodgate Community. This sun-filled unit offers effortless living with an open layout. The updated kitchen has new cabinets, granite countertops, tile backsplash, and new appliances. Townhome features 3 bedrooms, with 2 bedrooms on the main floor each having their own sliding door that opens to the new deck. Decks are oversized and perfect for

  Julie Luchina Coldwell Banker Realty

  1271 Washington St Unit 4, Middletown, CT 06457
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  /33

  $229,000

  • 2 Beds
  • 2 Baths
  • 1,025 Sq Ft

  111 Dekoven Dr Unit 703, Middletown, CT 06457

  Enjoy one-level living in the heart of downtown Middletown! This high-rise ranch condo at Rivers Edge offers 2 bedrooms and 2 full baths, along with the convenience of an in-unit washer and dryer. The spacious living room features custom built-ins and opens via slider to a private balcony showcasing beautiful views of the Connecticut River Valley and a slight view of CT River. Residents enjoy a

  

  Cheryl Zalewski

  eXp Realty

  (860) 788-4711

  111 Dekoven Dr Unit 703, Middletown, CT 06457
• 

  

  /19

  $669,900

  • 3 Beds
  • 1.5 Baths
  • 1,818 Sq Ft

  23 Meadowood Ln, Old Saybrook, CT 06475

  A lovely renovated ranch in the heart of "Meadowood", a desirable family friendly community in the charming town of Old Saybrook. The home features hardwood floors throughout, and a comfortable open layout with a large living room, stylish dining room, and a beautiful kitchen designed by local Hanford Kitchens. Three ample bedrooms await just around the hall. The yard is nicely landscaped and

  Craig Milton Re/Max Valley Shore

  23 Meadowood Ln, Old Saybrook, CT 06475
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  /29

  $739,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,564 Sq Ft

  794 Route 148, Killingworth, CT 06419

  Completed new construction set on 1.4 acres in Killingworth, this beautifully crafted Colonial offers 4 bedrooms and 2.5 bathrooms, including a spacious primary suite with a walk-in closet and full bath. Designed with modern living in mind, the open-concept floor plan seamlessly connects the main living spaces, creating a warm and inviting atmosphere ideal for both everyday living and

  

  Dana Weinstein

  Coldwell Banker Realty

  (860) 615-3927

  794 Route 148, Killingworth, CT 06419
• 

  

  /30

  $649,000 Open Fri 3:30PM - 5:30PM

  • 3 Beds
  • 3 Baths
  • 2,521 Sq Ft

  54 Lakeview Terrace, Westbrook, CT 06498

  Tucked away at the end of a quiet cul-de-sac, this beautiful 3 bedroom Cape-style home offers the perfect blend of privacy and comfort. With a dramatic two-story fireplace, the spacious interior includes two additional rooms ideal for home offices, a playroom, or guest space. The main-level master bedroom allows for easy first floor living, complemented by modernized kitchen and baths and all

  Jake Pulcini Chiarito Real Estate LLC

  54 Lakeview Terrace, Westbrook, CT 06498

Showing Results 41 - 80, Page 2 of 8