Homes for Sale near John Winthrop Middle School

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  /37

  $1,150,000

  • 8 Beds
  • 6 Baths
  • 7,300 Sq Ft

  87 Main St, Deep River, CT 06417

  VC Property Group is proud to present a rare two-parcel assemblage in Deep River, Connecticut, featuring a newer construction single-family residence, a five-unit mixed-use building with four residential apartments and one retail unit, and a contiguous 0.30-acre vacant parcel. Located in the highly desirable Lower Connecticut River Valley, the property is just 0.4 miles from Downtown Deep River

  

  Anthony Velez

  VC Property Group, LLC

  87 Main St, Deep River, CT 06417
• 

  Explore John Winthrop Middle School

• 

  

  

  /40

  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,957 Sq Ft

  47 E Kings Hwy, Chester, CT 06412

  A once-in-a-generation opportunity to become the steward of one of the Connecticut River Valley's most important historic estates. Built in 1798 by Jonathan Warner-founder of the Chester-Hadlyme Ferry, merchant, ship owner, farmer, Constable, Justice of the Peace, civic leader, and director of the Middlesex Turnpike-the Warner-Brooks House stands as a remarkable testament to early American

  

  Al Chiarito

  Chiarito Real Estate LLC

  47 E Kings Hwy, Chester, CT 06412
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  /37

  $999,000

  $191K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,905 Sq Ft

  13 Mill Rd, Essex, CT 06426

  Nestled at the end of a private lane in one of Essex Village's premier waterfront settings, this exceptional residence offers a rare blend of privacy, natural beauty, and walk-to-town convenience. Set on 1.5 acres overlooking Falls River Pond and North Cove, the property enjoys year-round water views, abundant wildlife, and room for future expansion. Designed to embrace its surroundings, the home

  

  Kelly Puorro

  Puorro Realty Group

  13 Mill Rd, Essex, CT 06426
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  /27

  $220,000

  • Studio
  • 1 Bath
  • 540 Sq Ft

  15 Sunset Terrace Unit 9, Essex, CT 06426

  Thoughtfully reimagined and beautifully remodeled, this fully furnished studio condominium offers a rare opportunity to own a turnkey retreat in the heart of Essex Village. Just bring your clothes-everything else has been carefully curated. Designed with both style and function in mind, the interior features all new windows, skylights, flooring, lighting, paint, custom details, and a beautifully

  

  Kelly Puorro

  Puorro Realty Group

  15 Sunset Terrace Unit 9, Essex, CT 06426
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  /6

  $979,860

  New Construction

  • 4 Beds
  • 3 Baths
  • 2,246 Sq Ft

  130 Mares Hill Rd, Essex, CT 06442

  Stunning new construction ranch set on a beautiful level lot, just under an acre. Thoughtfully designed for both comfort and flexibility. This To-Be Built contemporary home will feature an open-concept layout with a spacious kitchen, center island, and seamless flow to the living and dining areas-perfect for entertaining and everyday living. The private primary suite offers a walk-in closet and

  

  Kiki Sydnor

  Choice Realty

  130 Mares Hill Rd, Essex, CT 06442
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  /37

  $499,000

  $26K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,668 Sq Ft

  382 Cold Spring Dr, Westbrook, CT 06498

  Now offered at $499,000! Move right into this beautifully maintained 3-bedroom, 1.5-bath home set on a large, level, private lot in Westbrook. Enjoy the perfect balance of convenience and privacy-just minutes to the Westbrook train station, with easy on/easy off access to I-95, yet tucked away in a quiet neighborhood near the end of a cul-de-sac. Close to the Valley Shore YMCA, shopping,

  Paula Turley CR Premier Properties

  382 Cold Spring Dr, Westbrook, CT 06498
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  /40

  $795,000

  $30K PRICE DROP

  • 6 Beds
  • 3 Baths
  • 4,184 Sq Ft

  163 Main St, Deep River, CT 06417

  Rare mixed-use investment opportunity located in the heart of desirable Deep River Village. Positioned directly on Main Street, this 5-unit asset offers a strong blend of residential and commercial income within one of the Connecticut shoreline region's most sought-after rental and retail markets. The property consists of 3 residential apartments and 2 commercial storefronts occupied by long-term

  Connor Wenchell VC Property Group, LLC

  163 Main St, Deep River, CT 06417
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  /39

  $1,295,000

  • 4 Beds
  • 5 Baths
  • 4,937 Sq Ft

  53 Oakridge Dr, Westbrook, CT 06498

  Discover your own private oasis, this expansive custom-built home built on over 8 acres offers the perfect blend of privacy, comfort, and modern amenities. Featuring 4 bedrooms, 3 full bathrooms, 2 half bathrooms, and an oversized 2-car garage. Situated on the end of a private cul-de-sac the home is surrounded by peaceful natural beauty and thoughtfully designed for both everyday living and

  Cheryl Cook Re/Max Valley Shore

  53 Oakridge Dr, Westbrook, CT 06498
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  /26

  $2,195,000

  • 8 Baths
  • 12,155 Sq Ft

  31 N Main St, Essex, CT 06426

  Signature building in Essex Village. Originally the EE Dickinson corporate offices; grandfathered use in a residential zone. Reimagine this amazing space, water views, Essex Village, .78 acres of land, large footprint. Rare opportunity to own a cherished piece of Essex history

  Susan Malan William Pitt Sotheby's Int'l

  31 N Main St, Essex, CT 06426
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  /40

  $1,150,000

  • 2 Beds
  • 2.5 Baths
  • 3,278 Sq Ft

  112 River Rd, Essex, CT 06426

  A remarkable blend of architecture, nature, and modern comfort, this modernist custom home offers a living experience unlike any other. Nestled within a private and serene setting, the property is surrounded by natural beauty, where meandering streams feed a tranquil pond that spills into a cascading waterfall before winding through the marshlands toward the Connecticut River. The setting is both

  Gigi Giordano Taylor Compass Connecticut, LLC

  112 River Rd, Essex, CT 06426
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  /40

  $399,900

  • 2 Beds
  • 1 Bath
  • 1,817 Sq Ft

  79 River St, Deep River, CT 06417

  Move right into this Deep River home just moments from the Connecticut River and the charming village and town center. Since purchasing the property, the current owner has completed numerous valuable improvements, including a brand-new roof, new furnace, new oil tank, a tastefully remodeled kitchen, and an updated full bathroom. The main level offers inviting living spaces that blend character

  Gigi Giordano Taylor Compass Connecticut, LLC

  79 River St, Deep River, CT 06417
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  /40

  $900,000

  $95K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,343 Sq Ft

  136 Goose Hill Rd, Chester, CT 06412

  Welcome to 136 Goose Hill Rd. This home has been tastefully redesigned inside and out with no expense spared. Featuring 4 bedroom, 3 full bathroom, over 3,300 sq ft of beautifully finished living space sitting on just over 2 acres. Step inside to discover all-new hardwood flooring throughout the main level and a thoughtfully designed open-concept layout ideal for both everyday living and

  Chris Torrez RE/MAX One

  136 Goose Hill Rd, Chester, CT 06412
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  /40

  $1,459,000

  $31K PRICE DROP

  • 5 Beds
  • 5 Baths
  • 3,978 Sq Ft

  23 Welsch Farms Rd, Killingworth, CT 06419

  Nestled behind the circular driveway and surrounded by curated landscaping, this exceptional French Normandy country home offers a rare combination of architectural charm, artistic vision, quality craftsmanship and complete privacy. With 4,000 square feet of living space, the residence features five bedrooms and five baths, a beautiful modern kitchen, dining room with wet bar and large living

  Jay Kelly William Raveis Real Estate

  23 Welsch Farms Rd, Killingworth, CT 06419
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  /19

  $75,000

  $25K PRICE DROP

  • Land
  • 1 Acre
  • $75,000 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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  /38

  $475,000

  • 1 Bed
  • 1.5 Baths
  • 1,430 Sq Ft

  159 Wrights Pond Rd, Westbrook, CT 06498

  Welcome to 159 Wrights Pond, this secluded Chalet built on over 3 private acres, features beautiful hardwood floors, open floor plan ideal for entertaining and views of Wrights Pond. Other features include an oversized two car garage, detached two car garage with wood shop, and whole house generator. Wrights pond is ideal for kayaking, fishing ect. Located just minutes from award-winning

  Cheryl Cook Re/Max Valley Shore

  159 Wrights Pond Rd, Westbrook, CT 06498
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  /37

  $1,995,000

  $105K PRICE DROP

  • 11 Beds
  • 12 Baths
  • 8,500 Sq Ft

  59 Maple St, Chester, CT 06412

  A mixed-use and multifamily package located in Chester and Deep River, two of the most desirable towns in the Lower Connecticut River Valley. The offering includes: 59 Maple Street (Chester): 7-unit multifamily asset with an additional ~1,500 SF commercial warehouse on 2.5+ acres. 163 Main Street (Deep River): 5-unit mixed-use property positioned at the gateway to the downtown retail corridor.

  Connor Wenchell VC Property Group, LLC

  59 Maple St, Chester, CT 06412
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  /36

  $1,595,000

  • 3 Beds
  • 2.5 Baths
  • 2,708 Sq Ft

  46 West Ave, Essex, CT 06426

  1/2 mile walk to Essex Village, the marina, shops, and restaurants, this historic residence is nestled within one of Essex's most desirable neighborhoods. Thoughtfully reimagined by an established interior designer, the home masterfully blends modern luxury with the timeless charm quintessential to Essex. Original architectural details including hand-carved doors, staircase banister, fireplace

  Steve Wollman Wollman Realty

  46 West Ave, Essex, CT 06426
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  /40

  $3,395,000

  $1M PRICE DROP

  • 5 Beds
  • 6 Baths
  • 4,734 Sq Ft

  53 -1 Selden Rd, Lyme, CT 06371

  Selden Farm, a landmark 1690s property steeped in history and set in a picturesque corner of Lyme, is once again available for new stewardship. Upheld by only three families since 1695 when it sat on over 6,000 acres, it presents a rare opportunity to own a beautiful country Antique home now set on 9 pastoral acres abutting conservation land with sweeping views of Selden Cove and the CT. River.

  Joseph Rhodes Coldwell Banker Realty

  53 -1 Selden Rd, Lyme, CT 06371
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  /40

  $659,900

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  73 Long Hill Rd, Deep River, CT 06417

  Good design is all about the details and this well maintained custom Colonial is just what you have been looking for in the perfect shoreline home. Recently updated, the current owner's signature style has magically taken this charming home from ordinary to extraordinary with her colorful design. From the warm and welcoming entrance, to the well-appointed kitchen or the cozy family room centered

  Peg Mitchel Coldwell Banker Realty

  73 Long Hill Rd, Deep River, CT 06417
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  /14

  $205,000

  • 1 Bed
  • 1 Bath
  • 454 Sq Ft

  391 Main St Unit 134, Deep River, CT 06417

  Welcome to one of Deep River's hidden treasures! Ideally located in the heart of the beautiful Connecticut River Valley, this inviting condominium with low monthly HOA of $272 offers comfortable, low-maintenance living in a well-maintained 50-unit community with easy access to Routes 9 and I-95.Enjoy the convenience of nearby Main Street, where you'll find a grocery store, liquor store, charming

  Kathy Schellens William Pitt Sotheby's Int'l

  391 Main St Unit 134, Deep River, CT 06417
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  /40

  $7,250,000

  • 5 Beds
  • 4 Baths
  • 4,544 Sq Ft

  41 Joshua Ln, Old Lyme, CT 06371

  Elevated on a dramatic rise above the Connecticut River, this captivating property, aptly named "River Knoll," showcases one of the most breathtaking private settings on the river. The historic home has been featured in multiple publications such as Veranda and CTC&G for its exceptional beauty. Stunning landscape design frames every vista from the river's edge to the meticulously tended grounds

  Teri Lewis William Pitt Sotheby's Int'l

  41 Joshua Ln, Old Lyme, CT 06371
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  /36

  $1,650,000

  • 2 Beds
  • 3 Baths
  • 1,880 Sq Ft

  24 Mallard Point Rd, Essex, CT 06426

  Spectacular South Cove views, contemporary design, and effortless one-level living define this exceptional ranch in the heart of historic Essex. Perched above the tranquil waters of South Cove, this beautifully appointed home offers more than 3,000 square feet* of light-filled living space, where expansive windows frame ever-changing water views and create a seamless connection between indoors

  Sharon Craig William Raveis Real Estate

  24 Mallard Point Rd, Essex, CT 06426
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  /3

  $199,000

  $96K PRICE DROP

  • Land
  • 6.5 Acres
  • $30,615 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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  /40

  $599,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 3 Baths
  • 1,846 Sq Ft

  32 Sunset Terrace, Essex, CT 06426

  Welcome home to this beautifully maintained Cape-style residence offering over 1,800 square feet of finished living space, including 1,370 square feet on the main and upper levels plus an additional 476 square feet in the finished lower level. The main floor features a newly remodeled kitchen complete with quartz countertops, stainless steel appliances, and ample cabinet space, seamlessly flowing

  Chris Torrez RE/MAX One

  32 Sunset Terrace, Essex, CT 06426
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  /17

  $2,120,000

  Coming Soon

  • Land
  • 20.82 Acres
  • $101,825 per Acre

  0 Westbrook Rd, Essex, CT 06426

  Available for the first time in nearly 90 years, this exceptional 20.8 ACRES represent one of the very last large tracts of undeveloped land in historic Essex, widely celebrated as one of America's "Best Small Towns." The property features a striking combination of 8.5 level acres of virgin open field--ideal for farming, equestrian use or building--framed beautifully by an elevated wooded

  Todd Gould William Pitt Sotheby's Int'l

  0 Westbrook Rd, Essex, CT 06426
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  /12

  $899,900

  New Construction $10K PRICE INCREASE

  • 3 Beds
  • 3.5 Baths
  • 2,164 Sq Ft

  48A Ironworks Rd, Clinton, CT 06413

  Welcome to "The River Wood" a 3-bedroom custom home, nestled on a sprawling 4.81-acre parcel boasting an impressive 624 feet of riverfront along the scenic Menunketesuck River. This architectural gem is a seamless blend of luxurious living spaces, natural beauty, and tranquil surroundings. Upon entering, you'll be greeted by an inviting double door that leads into the heart of the home. The first

  Gigi Giordano Taylor Compass Connecticut, LLC

  48A Ironworks Rd, Clinton, CT 06413
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  /38

  $429,900

  $20K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,114 Sq Ft

  58 Union St, Deep River, CT 06417

  Welcome to 58 Union Street in the heart of charming Deep River! Just moments from the vibrant downtown, this beautifully updated home offers the perfect blend of character, comfort, and modern efficiency. Inside, you'll find hardwood floors, timeless architectural charm, and a thoughtfully renovated interior featuring a remodeled kitchen with all-new stainless-steel appliances, an updated

  Gigi Giordano Taylor Compass Connecticut, LLC

  58 Union St, Deep River, CT 06417
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  /40

  $829,000

  • 4 Beds
  • 6 Baths
  • 7,309 Sq Ft

  33 Deep River Rd, Centerbrook, CT 06409

  Incredible investment opportunity. Mixed use/flex space including two existing apartments. Historic building that has had multiple uses including an antique book store and once a brush factory. Many updates in recent years with a variety of potential uses. Level .74 acre lot, gravel parking lot, great visibility and signage. There are two apartments and multiple office/flex spaces. The property

  Susan Malan William Pitt Sotheby's Int'l

  33 Deep River Rd, Centerbrook, CT 06409
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  /40

  $5,775,000

  • 4 Beds
  • 3.5 Baths
  • 9,852 Sq Ft

  89 River Rd, East Haddam, CT 06423

  Where Architectural Inspiration Meets the Majesty of the Connecticut River. Perched majestically on 15.22 acres along the eastern bank of the Connecticut River, 89 River Road offers a rare convergence of architectural pedigree, natural beauty, privacy, and fully realized lifestyle design. Designed, owned, and meticulously crafted by one of America's leading architects, this 12,836-square-foot,

  Colette Harron William Pitt Sotheby's Int'l

  89 River Rd, East Haddam, CT 06423
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  /40

  $779,000

  $45K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,433 Sq Ft

  257 W Elm St, Deep River, CT 06417

  Tucked away on 4.4 acres of rolling countryside with direct frontage on a tranquil reservoir, this custom-built farmhouse Cape is a rare find. Thoughtfully constructed in 2002 and lovingly maintained by its original owner, the home offers three bedrooms, two and a half baths, and a first-floor primary suite with a generous walk-in closet and en suite bath. Hardwood floors, a wood-burning

  John Izzo William Raveis Real Estate

  257 W Elm St, Deep River, CT 06417
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  /15

  $995,000

  • Land
  • 1.02 Acres
  • $975,490 per Acre

  41B River Rd, Essex, CT 06426

  Extremely rare! Peaceful, tranquil waterfront lot available. This special location is on Falls River Cove with a shared dock and consists of 1+ acres ready for new construction. View restrictions in place. Please see declaration of restrictions, covenants and easements in the attached. The lot is not visible from the road; shown by appointment only.

  Susan Malan William Pitt Sotheby's Int'l

  41B River Rd, Essex, CT 06426
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  /2

  $175,000

  $25K PRICE DROP

  • Land
  • 10.4 Acres
  • $16,827 per Acre

  0 Kelseytown Bridge Rd, Clinton, CT 06413

  Build your dream home on this exceptional, expansive lot located in the highly desirable Kelseytown neighborhood of Clinton. Spanning a generous 10.4 picturesque acres, this beautiful parcel offers the ultimate canvas for a private estate, a sprawling ranch, or a custom multi-generational retreat. Enjoy a serene, nature-filled escape surrounded by peaceful woodlands while remaining just minutes

  Maria Phillips William Raveis Real Estate

  0 Kelseytown Bridge Rd, Clinton, CT 06413
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  /37

  $895,000

  $100K PRICE INCREASE

  • 3 Baths
  • 4,260 Sq Ft

  3 Essex Square, Essex, CT 06426

  A rare and unparalleled opportunity to acquire an iconic c.1900 property set atop a gentle rise at the head of Main Street in historic Essex Village. This substantial, professionally maintained building is comprised of two legal condominium units, and offers unmatched flexibility with its APPROVED MIXED RETAIL/OFFICE/RESIDENTIAL USE status. Potential to create your own custom Essex village

  Rick Weiner William Pitt Sotheby's Int'l

  3 Essex Square, Essex, CT 06426
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  /40

  $7,889,000

  • 3 Beds
  • 5 Baths
  • 4,664 Sq Ft

  175 River Rd, Essex, CT 06426

  Set along one of Essex's most coveted stretches of River Road, this exceptional waterfront estate offers a rare blend of understated elegance, privacy, and Connecticut River waterfront. Privately sited on nearly three acres, the property enjoys a serene, tucked-away feel while remaining just minutes from the heart of Essex Village. Custom-built and thoughtfully designed by its original owner, the

  Susan Malan William Pitt Sotheby's Int'l

  175 River Rd, Essex, CT 06426
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  /36

  $4,650,000

  $500K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 6,346 Sq Ft

  150 Joshuatown Rd, Old Lyme, CT 06371

  Welcome to 150 Joshuatown Road in Lyme, a stunning, custom built residence sited on over 30 acres of bucolic land, with specimen trees, beautiful landscaping, and over 1/4 mile of impressive rebuilt stone walls. The main level features a welcoming foyer, Chef's kitchen with breakfast room, a cherry paneled library with vaulted ceiling and warming fireplace, commodious dining room, living room

  Jennifer Caulfield William Pitt Sotheby's Int'l

  150 Joshuatown Rd, Old Lyme, CT 06371
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  /39

  $850,000

  • 4 Beds
  • 2.5 Baths
  • 2,756 Sq Ft

  78 Meadow Woods Rd, Deep River, CT 06417

  An oasis of privacy, peace and elegance awaits you here at one of Deep River's most desirable locations. Spring and summer song birds serenade you from the refurbished deck nestled among mature trees covering 3.21 acres of gently sloping land. As you enter through colorful gardens professionally landscaped for minimal maintenance, you'll be greeted by rich Brazilian Cherry hardwood floors that

  Gerard Sullivan Coldwell Banker Realty

  78 Meadow Woods Rd, Deep River, CT 06417
• 

  

  /40

  $675,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,711 Sq Ft

  170 Dennison Rd, Westbrook, CT 06498

  Escape to your own private 3-acre compound offering endless possibilities! This charming 3-bedroom, 2-bath Cape Cod is nestled in a serene setting surrounded by nature. The bright, open floor plan features an updated kitchen with granite countertops, stainless steel appliances, and flows into a cozy dining area and den with heated hardwood floors. The main level also offers a spacious bedroom,

  Erin Connelly Coldwell Banker Realty

  170 Dennison Rd, Westbrook, CT 06498
• 

  

  /40

  $699,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 2,755 Sq Ft

  11 Kitteridge Hill Rd, Old Saybrook, CT 06475

  Tucked away on a peaceful cul-de-sac off School House Road, this beautifully maintained Cape offers over 2,700 square feet of finished living space in one of Old Saybrook's most desirable locations. Directly across from The Preserve trail access and just moments from Clark Park, this home is perfectly positioned for those who appreciate nature, recreation, and privacy. The inviting main level

  Jessica Blancato William Pitt Sotheby's Int'l

  11 Kitteridge Hill Rd, Old Saybrook, CT 06475
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  /33

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 3,141 Sq Ft

  340 Toby Hill Rd, Westbrook, CT 06498

  Your Westbrook Retreat Awaits. Welcome to 340 Toby Hill Road- a spacious 3141 square foot home offering the perfect opportunity to enjoy the comfort of a generous home in beautiful Westbrook. Discover the charm, space and privacy of this beautiful Westbrook home, ideally situated in one the Connecticut's most desirable coastal communities. Offering approximately 3,141 square feet of living space,

  Brian Jermainne Team Jermainne Real Estate Services, LLC

  340 Toby Hill Rd, Westbrook, CT 06498
• 

  

  /40

  $3,950,000

  • 4 Beds
  • 5.5 Baths
  • 7,124 Sq Ft

  274 Joshuatown Rd, Lyme, CT 06371

  PRIVATELY SITED ON 18 ACRES HIGH ABOVE THE CONNECTICUT RIVER, this extraordinary modern estate is defined as much by its setting as its architecture. A long, private drive creates a remarkable sense of arrival, revealing a residence thoughtfully positioned to capture sweeping river views, changing light, and the quiet beauty of the surrounding landscape. Extraordinary views and dramatic

  Margaret Douglas William Raveis Real Estate

  274 Joshuatown Rd, Lyme, CT 06371

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