Middlesex County CT Homes for Sale with Acreage

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  /21

  $850,000

  • 4 Beds
  • 2 Baths
  • 8,382 Sq Ft

  26 Ferry Rd, Chester, CT 06412

  Located in the Town of Chester, this mixed-use property presents a rare opportunity to acquire a distinctive asset in one of Connecticut's most desirable markets. As it stands, the property consists of approximately 5,000 square feet of commercial space, including one loading dock, three (3) garages, and an oversized on-site parking lot, supporting a wide range of operational and occupancy needs.

  

  Anthony Velez

  VC Property Group, LLC

  (860) 579-1600

  26 Ferry Rd, Chester, CT 06412
• 

  

  

  /40

  $650,000

  • 3 Beds
  • 3 Baths
  • 2,752 Sq Ft

  1 Ferry Rd, Chester, CT 06412

  An extraordinary offering in one of Connecticut's most beloved river towns. Stunning sunrises over unobstructed views of Chester Creek sets the tone for this rare piece of Chester history. The Bani Denison homestead dates to 1781 and once served as Chester's first post office. Thoughtfully restored, this classic embankment Colonial with Dutch kick gambrel style roof offers modern amenities while

  

  Jennifer D'Amato

  Real Broker CT, LLC

  (860) 454-6525

  1 Ferry Rd, Chester, CT 06412
• 

  

  

  /40

  $1,895,000

  • 4 Beds
  • 4.5 Baths
  • 5,610 Sq Ft

  108 Westbrook Rd, Essex, CT 06426

  Amazing custom built Nantucket style Cape situated on sprawling grounds, terraced high above a picturesque great yard & overseen by natural highlands. The setting is nothing but breathtaking! Inclusive is an inground Gunite pool engulfed by the primary hardscape which walks-out from the lower level & is situated high above the great yard. A magnificent carriage house featuring a 4 bay garage &

  

  Kevin Geysen

  William Pitt Sotheby's Int'l

  (860) 321-5635

  108 Westbrook Rd, Essex, CT 06426
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  /2

  $789,900 New Construction

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

  62 Cornwall St, Portland, CT 06480

  Come custom build the Home of your dreams. With a wide selection of plans, and possible Options and upgrades, this is something you do not want to wait for!

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 943-4408

  62 Cornwall St, Portland, CT 06480
• 

  

  /2

  $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
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  /39

  $1,200,000

  • 4 Beds
  • 3.5 Baths
  • 4,176 Sq Ft

  21 & 23 Olmstead Rd, East Haddam, CT 06423

  Sophisticated Colonial Retreat with Resort-Style Backyard. Just one mile from East Haddam Town Beach and moments from the Connecticut River, Goodspeed Opera House, and scenic trails, this exceptional 4-bedroom, 3.5-bath Dutch Colonial offers over 4,000 square feet of refined living space. A dramatic two-story foyer with custom millwork is flanked by a formal dining room and private office with

  Tina Rupp William Pitt Sotheby's Int'l

  21 & 23 Olmstead Rd, East Haddam, CT 06423
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  /40

  $1,049,900 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  90 Meshomasic Trail, Portland, CT 06480

  Newly constructed home offering over 3,100 sq ft of refined living space, privately set on 1.30+ acres in the desirable Chatham Ridge community, just minutes from Glastonbury. Thoughtfully designed with exceptional craftsmanship and elevated finishes, this home blends modern style with timeless design. The open-concept layout features 4 bedrooms, 4 bathrooms, and an oversized three-bay garage. A

  Angie Santoro Realty Executives Boston West

  90 Meshomasic Trail, Portland, CT 06480
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  /2

  $995,000

  • Land
  • 1.25 Acres
  • $796,000 per Acre

  1333A Boston Post Rd, Old Saybrook, CT 06475

  An exceptional opportunity - Nestled on 1.25 acres of vacant land with public water access, this prime property is located in the sought-after Gateway Business B-4 District Within mile of national tenants, boasting a daily traffic count of 15,900. This versatile lot is zoned for a variety of uses such as retail stores, professional offices, medical clinics, theaters, and more. Its

  Ron Lyman Lyman Real Estate Brokerage & Development

  1333A Boston Post Rd, Old Saybrook, CT 06475
• 

  

  /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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  /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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  /15

  $400,000

  • 3 Beds
  • 2 Baths
  • 1,816 Sq Ft

  35 Sipples Hill Rd, Moodus, CT 06469

  Well kept two-family residence that may be utilized as a single family home or perfect in-law unit on two private level acres with detached four car heated garage and large shed. Garage has 220V AC for welding or large air compressor. Upstairs has two bedrooms, large family room, large eat in kitchen and a large three seasons porch that leads to a deck. Downstairs has a single bedroom, large

  Dale Bunn Riverview Realty, LLC

  35 Sipples Hill Rd, Moodus, CT 06469
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  /40

  $379,900

  • 3 Beds
  • 2.5 Baths
  • 1,716 Sq Ft

  55 Saw Mill Rd, Middletown, CT 06457

  Set on a picturesque 1.4-acre lot and lovingly maintained by its original owner, 55 Saw Mill Road offers a rare opportunity to own a truly special property in Middletown. This home reflects years of meticulous care, with thoughtful upkeep evident throughout! One of the standout features is its exceptional setting-directly facing the Highland Pond Preserve. Enjoy peaceful views, natural beauty,

  Jeffrey Anderson William Pitt Sotheby's International Realty

  55 Saw Mill Rd, Middletown, CT 06457
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  /35

  $575,000 Open Sat 11AM - 1PM

  • 2 Beds
  • 2.5 Baths
  • 4,205 Sq Ft

  286 Marlborough St, Portland, CT 06480

  A Rare Blend of Space, Flexibility & Opportunity. Currently configured with a bright and inviting two-bedroom, one-bath apartment upstairs, the home also features a spacious lower level that was formerly used as a salon. With its generous layout and separate entrance, this space can be thoughtfully reimagined and seamlessly converted into additional living areas-ideal for expanding the home into

  Kris Robinson Eagle Eye Realty PLLC

  286 Marlborough St, Portland, CT 06480
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  /24

  $349,900

  • 4 Beds
  • 1 Bath
  • 1,509 Sq Ft

  475 Ballfall Rd, Middletown, CT 06457

  Welcome to this charming Colonial-style home set on a generous 3.3-acre lot, offering the perfect blend of comfort, space, and modern updates. The exterior showcases classic appeal with a welcoming front entry & an attached 2 car garage, all surrounded by open land that provides privacy and endless possibilities. Step inside to discover a beautifully updated kitchen featuring stainless steel

  Michelle Mazzotta eXp Realty

  475 Ballfall Rd, Middletown, CT 06457
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  /40

  $3,995,000

  • 6 Beds
  • 4.5 Baths
  • 5,536 Sq Ft

  41 Watrous Point Rd, Old Saybrook, CT 06475

  Discover one of the most coveted vantage points on the lower Connecticut River-a mid-century modern sanctuary perched on a private 2.7-acre waterfront peninsula where land, river, and sky converge in perfect harmony. With an extraordinary 875 feet of water frontage embracing both the Connecticut River and the pristine Turtle Creek nature preserve, this property is a haven for bird enthusiasts and

  Teri Lewis William Pitt Sotheby's Int'l

  41 Watrous Point Rd, Old Saybrook, CT 06475
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  /37

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,062 Sq Ft

  5 Rosewood Ln, Ivoryton, CT 06442

  Tucked away at the end of a quiet cul-de-sac in desirable Ivoryton, this 15-year-young custom-built home offers the perfect blend of privacy, flexibility, and future potential. Thoughtfully designed with a "live like a ranch" layout, the main level features three bedrooms and two full baths, ideal for easy everyday living. The heart of the home is the open-concept kitchen and living area, perfect

  Gigi Giordano Taylor Compass Connecticut, LLC

  5 Rosewood Ln, Ivoryton, CT 06442
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  /3

  $295,000

  • Land
  • 6.5 Acres
  • $45,385 per Acre

  0 Brainard Rd, Westbrook, CT 06498

  Nestled in the desirable Pond Meadow area, this private 6.5 Acre property offers a rare opportunity to create your ideal retreat in this idyllic coastal community. Featuring multiple leveled building sites, the land is well suited for flexibility and privacy. In initial feasibility study has been completed and additional site work would be necessary to begin construction. The property showcases a

  Rick Allen William Raveis Real Estate

  0 Brainard Rd, Westbrook, CT 06498
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  /39

  $2,125,000

  • 5 Beds
  • 4.5 Baths
  • 3,532 Sq Ft

  13 Hemlock Dr, Essex, CT 06426

  A sprawling luxury home offering one level living with stunning views of South Cove and quintessential Essex village beyond. With over 3,500 sf of newly designed and renovated living space including 11 rooms with 5 bedrooms and multiple baths. A soaring two-story sunroom overlooks stunning patio and garden areas complete with an inground pool set on over 1 acre of park-like grounds. Gorgeous

  Pat Park Berkshire Hathaway NE Prop.

  13 Hemlock Dr, Essex, CT 06426
• 

  

  /5

  $215,000

  • Land
  • 7.4 Acres
  • $29,054 per Acre

  0 Plains Rd Unit 24163414, Haddam, CT 06438

  Prime 7.4-acre land in Haddam offering two buildable lots with flexible options-keep as a large private estate or split into two parcels thanks to the available free split. Located in a tranquil, rural setting near Route 154, the Connecticut River, and scenic hiking trails. Close to Gillette Castle and the Goodspeed Opera House, with easy access to major routes. Perfect for investors or buyers

  Danielle Spada Coldwell Banker Realty

  0 Plains Rd Unit 24163414, Haddam, CT 06438
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  /39

  $369,900 Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  113 W High St, East Hampton, CT 06424

  Enjoy easy one-floor living in this well maintained 3 bedroom ranch, conveniently located near town, schools, and Lake Pocotopaug. The home features a spacious living room with a cozy wood burning fireplace, perfect for relaxing or entertaining, along with pegged plank wood floors and solid wood doors throughout, adding warmth and character. The primary bedroom includes both a standard closet and

  Craig Milton Re/Max Valley Shore

  113 W High St, East Hampton, CT 06424
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  /40

  $769,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 3.5 Baths
  • 2,940 Sq Ft

  38 Beech Tree Ridge, Killingworth, CT 06419

  Tucked away on 3.4 peaceful, private acres, this beautifully updated Colonial has been thoughtfully improved from top to bottom since it was built in 1997. The kitchen is a standout, featuring gorgeous marble countertops, high-end appliances, and the added bonus of double dishwashers and ovens-perfect for hosting and everyday convenience. It opens right into a cozy family room with a wood-burning

  Katie Cassidy Real Broker CT, LLC

  38 Beech Tree Ridge, Killingworth, CT 06419
• 

  

  /31

  $999,500

  • 3 Beds
  • 2.5 Baths
  • 1,476 Sq Ft

  559 Route 81, Killingworth, CT 06419

  Contractors and hobbyists take note of this incredible opportunity in Killingworth! This adorable, gabled Cape is set back on a spectacular 2.3 acre lot and features two large accessory barns offering unparalleled storage, workshop, or home business possibilities. The wood-sided main home boasts 3 bedrooms, 2.5 baths, and an attached 2-car garage. Inside, this freshly painted, delightful 1937

  Tina Rupp William Pitt Sotheby's Int'l

  559 Route 81, Killingworth, CT 06419
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  /37

  $699,000

  • 3 Beds
  • 2 Baths
  • 2,948 Sq Ft

  24 Tower Hill Rd, Clinton, CT 06413

  Tucked away on over 7.5 private acres and abutting protected state forest, this rare Clinton property offers the perfect blend of tranquility, space, and flexibility. A true retreat, the setting provides exceptional privacy while still being conveniently located near shoreline amenities. This one owner home was designed for easy one-level living, the home features an inviting open floor plan with

  Gigi Giordano Taylor Compass Connecticut, LLC

  24 Tower Hill Rd, Clinton, CT 06413
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  /40

  $1,895,000

  • 3 Beds
  • 3 Baths
  • 2,966 Sq Ft

  12 Jackson Rd, Killingworth, CT 06419

  Welcome to Stone Heron Farm, an extraordinary 74+ acre estate offered as five parcels, creating one of the most versatile and rare compound opportunities in Connecticut. Tucked away on a quiet country road, 12 Jackson Road combines timeless New England charm with exceptional land value, privacy and multi-use potential.The main residence, an updated 1806 Cape, features exposed beams, rich

  Patricia Guarantano William Pitt Sotheby's Int'l

  12 Jackson Rd, Killingworth, CT 06419
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  /24

  $439,900

  • 3 Beds
  • 1.5 Baths
  • 1,488 Sq Ft

  89 S End Ave, Durham, CT 06422

  Charm, Location, convenience. Just outside the Town Center. Find this endearing three bedroom colonial. Genuine character is found throughout every inch of this call from the past. Living room is warm and inviting with pine floors, beams and working fireplace with built in hutch. Dining room as built in corner hutch.Has 1.26 acres, out door living is splendid - grow your own vegetables, raise

  Raymond Valenti RE/MAX Alliance

  89 S End Ave, Durham, CT 06422
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  /40

  $949,900

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft

  1 Beamon Meadow Place, Old Saybrook, CT 06475

  Tucked away in a tranquil setting overlooking an ever changing tidal marsh, this exceptional coastal retreat offers a rare blend of privacy, natural beauty, and coveted deeded access to Cornfield Point Beach just a short stroll away. Privately set on 1.44 acres and approached by a charming bridge, the property feels like a hidden sanctuary while remaining just moments from the vibrant heart of

  Linda Toscano Coldwell Banker Realty

  1 Beamon Meadow Place, Old Saybrook, CT 06475
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  /39

  $969,900 Open Sat 12PM - 2PM

  • 3 Beds
  • 4.5 Baths
  • 2,756 Sq Ft

  55 North Rd, Cromwell, CT 06416

  This stunning custom-built Ranch sits on 5 secluded acres of land. The home features 4-5 bedrooms, 3-1/2 baths and has every upgrade and amenity imaginable, including 4 bedrooms & 2-1/2 baths on main level. The lower level potential is unlimited - Possible in-law w/ additional huge finished area, including full bath, additional den/bedroom, walkout entrance, big media/game room & bright windows.

  Elizabeth Harrison Hagel & Assoc. Real Estate

  55 North Rd, Cromwell, CT 06416
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  /38

  $775,000 Open Sat 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,600 Sq Ft

  10 Cove Hill Rd, Essex, CT 06426

  Private 2.2 acre property with an in-ground pool just minutes from Essex Village. Set on a lightly wooded lot, this 2 bedroom, 2 full bath home offers a combination of privacy and convenience near the shops, restaurants, and marinas in the village. Inside you will find a spacious kitchen and great room with vaulted ceilings, island seating, and plenty of room for a dining table. A formal living

  Kara Bell J.M. REALTY

  10 Cove Hill Rd, Essex, CT 06426
• 

  

  /31

  $765,000

  • 3 Beds
  • 3 Baths
  • 2,701 Sq Ft

  74 Oxbow Rd, Higganum, CT 06441

  Nestled on a quiet deadend street among a collection of custombuilt homes, this stately colonial enjoys a rare frontrow view of more than 500 acres of protected state land. The first floor welcomes you with an open layout and 9foot ceilings that create an airy, connected flow throughout the main living spaces. A wellappointed mudroom-complete with laundry-sits just off the kitchen and includes a

  Cortney Emshwiller-Swokla Coldwell Banker Realty

  74 Oxbow Rd, Higganum, CT 06441
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  /12

  $449,900

  • 3 Beds
  • 2.5 Baths
  • 1,680 Sq Ft

  71 Schulman Veslak Rd, East Haddam, CT 06423

  Appealing Colonial nestled on a sprawling 7-acre lot. Boasting impressive frontage on two roads, this property offers both privacy and accessibility, making it a truly unique find. Enjoy the peaceful ambiance of a brook meandering through your backyard, while the partially fenced and relatively flat terrain provides both security and endless possibilities for outdoor activities. Step inside to a

  Alexis Devlin Coldwell Banker Realty

  71 Schulman Veslak Rd, East Haddam, CT 06423
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  /26

  $539,900

  • 5 Beds
  • 2 Baths
  • 1,808 Sq Ft

  296 E Main St, Clinton, CT 06413

  Downtown Two-Family Investment Opportunity! Well-located two-family home close to everything - including shops, restaurants, and nearby beaches. Major updates have already been completed, including the roof, windows, mechanical systems, kitchens, and baths, making this a strong turnkey investment. Enjoy marsh views from the backyard, offering a scenic and relaxing outdoor setting. Owner financing

  Bonnie Fillion Berkshire Hathaway NE Prop.

  296 E Main St, Clinton, CT 06413
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  /17

  $114,900

  • Land
  • 2.36 Acres
  • $48,686 per Acre

  91-A Flatbrook Rd Unit 91, East Hampton, CT 06424

  This exceptional, approved building lot presents a unique opportunity to create a custom residence tailored to your preferences. The generous size of this property provides ample room for a well-designed home and extensive outdoor amenities. Envision a home that seamlessly integrates with its natural surroundings. Whether your architectural style leans towards a contemporary aesthetic with clean

  Kelvin Wilson Berkshire Hathaway NE Prop.

  91-A Flatbrook Rd Unit 91, East Hampton, CT 06424
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  /39

  $699,900

  • 4 Beds
  • 2.5 Baths
  • 2,831 Sq Ft

  85 McVeagh Rd, Westbrook, CT 06498

  Exceptional Country Living Close to Town - Westbrook, CT Discover the perfect blend of country charm and modern comfort in this beautifully maintained farmhouse colonial, ideally located in the scenic shoreline town of Westbrook. Built in 2002 by a respected local builder, this spacious home offers over 2,800 sq. ft. of living space, plus additional finished (unheated) basement area-plenty of

  Lynn Lehrman Re/Max Valley Shore

  85 McVeagh Rd, Westbrook, CT 06498
• 

  

  /19

  $539,900

  • 4 Beds
  • 3.5 Baths
  • 4,390 Sq Ft

  57 Summer St, Portland, CT 06480

  Set on a generous 1.2-acre lot in Portland, this expansive ranch offers an incredible amount of space and potential for someone ready to bring their vision to life. With over 4,300 square feet of living space, the home features 10 rooms including 4 bedrooms and 3 full baths plus a half bath, providing plenty of room for extended living, hobbies, or multi-generational needs. The layout offers the

  Carl Guild Carl Guild & Associates

  57 Summer St, Portland, CT 06480
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  /36

  $519,900

  • 3 Beds
  • 3 Baths
  • 1,847 Sq Ft

  280 Tuttle Rd, Durham, CT 06422

  Welcome to this beautiful 3-bedroom, 3 full bath, attached 2-car garage sprawling ranch set on 1.08 acres, offering breathtaking views of downtown Durham. This unique home also features a finished lower level with its own living space and direct garage access, creating a great potential for an in-law living arrangement. Step inside to a bright, open entryway with cathedral wood ceilings and

  Giulia Terese Hagel & Assoc. Real Estate

  280 Tuttle Rd, Durham, CT 06422
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  /40

  $1,400,000

  • 3 Beds
  • 2.5 Baths
  • 2,446 Sq Ft

  301 Fox Hopyard Rd, East Haddam, CT 06423

  Welcome to 301 Fox Hopyard Road In the Fox Hopyard Golf and Country club community. The impeccably crafted 3 bedroom, 2.5 bath Colonial with first floor Primary suite, featuring 2,446 sqft. of refined living space and distinctive architectural detailing. Step into the stunning Great room open to the kitchen with French doors that frame the formal dining room. The sundrenched 4 season glass den

  Maddy Mattson Coldwell Banker Realty

  301 Fox Hopyard Rd, East Haddam, CT 06423
• 

  

  /40

  $1,350,000

  • 4 Beds
  • 2.5 Baths
  • 3,301 Sq Ft

  6 Parkman Place, Old Saybrook, CT 06475

  Nestled on a quiet cul-de-sac in the heart of the Connecticut River Shoreline, this stunning 3,301 SF, 4-bedroom, 2.1 bath home represents a masterclass in coastal sophistication. Meticulously renovated, this residence offers a rare combination of high-end design, graceful grounds, and absolute peace of mind and privacy, situated in a town recognized as one of the top ten places to live in

  Rick Weiner William Pitt Sotheby's Int'l

  6 Parkman Place, Old Saybrook, CT 06475
• 

  

  /40

  $1,179,900 Open Sat 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 4,109 Sq Ft

  96 Ayers Point Rd, Old Saybrook, CT 06475

  Discover the serenity of Ayers Point in this spacious 3400 sq ft home with captivating views of the Connecticut River and surrounding marshland. Privately set with a beautiful inground pool and lush gardens, this retreat is perfect for those seeking a coastal lifestyle near boating and village charm. The home features both main and upper level primary suites, offering flexibility and comfort for

  Joel Lucas Coldwell Banker Realty

  96 Ayers Point Rd, Old Saybrook, CT 06475
• 

  

  /29

  $750,000

  • 4 Beds
  • 3.5 Baths
  • 3,655 Sq Ft

  322 Tuttle Rd, Durham, CT 06422

  HIGHEST AND BEST BY 5p, TUESDAY, March 31. Built in 2019, this exceptional ranch offers 2,732 square feet of refined single-level living, complemented by approximately 883 square feet of newly finished lower-level space. Designed with both elegance and functionality in mind, the home features 4 bedrooms, 3.5 bathrooms, and a sophisticated open-concept layout ideal for modern living. The expansive

  Jamie Dumaine KW Legacy Partners

  322 Tuttle Rd, Durham, CT 06422
• 

  

  /39

  $799,900

  • 3 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  45 Main St, Essex, CT 06426

  The Parker Bull House, circa 1754 located in Ivoryton overlooking the Falls River, this stately home is a unique blend of original antique features with updated modern amenities. The large sunny kitchen has granite countertops and stainless-steel appliances, hardwood floors, and is adjacent to a spacious pantry/laundry room, heated sunroom, and a covered porch. The living room has a large

  Susan Malan William Pitt Sotheby's Int'l

  45 Main St, Essex, CT 06426

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