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Homes for Sale near John Winthrop Middle School

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  • /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

    Agent Photo

    Al Chiarito

    Chiarito Real Estate LLC

    (860) 846-4174

    47 E Kings Hwy, Chester, CT 06412
  • /40

    $1,795,000

    $100K PRICE DROP
    • 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 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 &

    Agent Photo

    Kevin Geysen

    William Pitt Sotheby's Int'l

    (860) 321-5635

    108 Westbrook Rd, Essex, CT 06426
  • /37

    $1,350,000

    • 7 Beds
    • 6 Baths
    • 3,787 Sq Ft

    87 Main St, Deep River, CT 06417

    VC Property Group is proud to present a two-parcel assemblage in Deep River, Connecticut, offering stabilized mixed-use income with residential value and land optionality. The assemblage includes: 87 Main Street - a parcel improved with: a Newer Construction Single Family Residence and a 5-unit mixed-use building (four residential apartments and one retail unit) 55 Prospect Street - a contiguous

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    Anthony Velez

    VC Property Group, LLC

    (860) 579-1057

    87 Main St, Deep River, CT 06417
  • /39

    $1,195,000

    Open Sat 11AM - 1PM
    • 5 Beds
    • 3.5 Baths
    • 3,902 Sq Ft

    8 Squire Ln, Essex, CT 06426

    Nestled on a cul-de-sac just a short stroll from the Village of Essex, this exceptional Colonial offers timeless elegance, modern comfort, and resort style living. Thoughtfully designed and beautifully maintained, the home welcomes you with a gracious foyer, detailed millwork, and sun filled living spaces that create an inviting atmosphere throughout. At the heart of the home is a beautifully

    Agent Photo

    Tammy Tinnerello

    William Pitt Sotheby's Int'l

    (860) 852-6398

    8 Squire Ln, Essex, CT 06426
  • /40

    $949,000

    Open Sat 11AM - 1PM
    • 6 Beds
    • 4.5 Baths
    • 2,772 Sq Ft

    7 Orchard Heights Rd, Essex, CT 06426

    Set on a picturesque street in the charming town of Essex, 7 Orchard Heights Road offers classic New England living with spacious interiors and inviting outdoor spaces designed for everyday comfort and entertaining. This well maintained Colonial features a generously sized kitchen with ample cabinetry and workspace, flowing seamlessly into the main living areas for easy gatherings and relaxed

    Agent Photo

    Tammy Tinnerello

    William Pitt Sotheby's Int'l

    (860) 431-2021

    7 Orchard Heights Rd, Essex, CT 06426
  • /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 contemporary home features 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 en-suite bath,

    Agent Photo

    Kiki Sydnor

    Choice Realty

    (860) 288-9987

    130 Mares Hill Rd, Essex, CT 06442
  • /34

    $10,000,000

    • 5 Beds
    • 8 Baths
    • 7,021 Sq Ft

    153 Ferry Rd, Lyme, CT 06439

    Welcome to 'Highover,' a 25-acre hilltop estate on the Connecticut River, voted the WSJ House of the Month nationwide. Over half a mile of waterfront, with natural barriers, ensures unmatched privacy and security. Accommodation for extended family and live-in help. Uniquely poised between New York and Boston, and less than an hour by helicopter from JFK, Logan, and Bradley. The home, designed by

    Edward Hillyer William Raveis Real Estate

    153 Ferry Rd, Lyme, CT 06439
  • /40

    $825,000

    • 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
  • /40

    $950,000

    • 4 Beds
    • 2.5 Baths
    • 2,841 Sq Ft

    10 Shelter Rock Rd, East Haddam, CT 06423

    A private approach which leads to this refined colonial home, set on more than four secluded acres. The property includes a heated mineral pool, expansive stone patios, Brazilian Ipe decking and full-property indoor/outdoor sound-an exceptional setting for effortless entertaining. With roughly 20 acres of protected association land as its backdrop, the grounds offer rare privacy along with

    Bill Moore Coldwell Banker Realty

    10 Shelter Rock Rd, East Haddam, CT 06423
  • /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
  • /40

    $945,000

    $50K 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
  • /31

    $449,500

    $5K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,122 Sq Ft

    85 River Rd Unit G2, Essex, CT 06426

    Well appointed two story, two bedroom townhouse located in the waterfront community of Heritage Cove. An updated kitchen, primary bath, neutral color palette for the walls, trim and flooring makes this home truly move in ready. Conveniently located for on street parking and the units assigned carport. Just a stroll across the lawn to enjoy the pool and community fire table add to this unique

    Patrick Kilty William Raveis Real Estate

    85 River Rd Unit G2, Essex, CT 06426
  • /32

    $599,900

    • 2 Beds
    • 1 Bath
    • 980 Sq Ft

    17 Grandview Terrace, Essex, CT 06426

    Village living at its best! Lovely inviting Ranch offering Living Rm. with cozy Fireplace, 2BR, charming Kitchen, HW floors, Breezeway/Sun rm. and attached garage. Fun and adventure is just a short walk to nearby Library, Playground, Tennis Courts, Pond, Dog Park, Town Center Shops, and Dining. Furnace 10yr, HW heater 5yr old. Roof 2025. Dining preferences possible in LR nook or Sun Rm. Come

    Diane Beckwith Popolizio William Raveis Real Estate

    17 Grandview Terrace, Essex, CT 06426
  • /40

    $1,490,000

    • 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
  • /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
  • /15

    $212,000

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft

    92 Main St Unit 107, Deep River, CT 06417

    Step into a loft-style townhouse in the historic Piano Works building that blends vintage charm with modern living. With its own private entrance and location in a 4-unit outbuilding, this home offers peace and privacy-no upstairs or downstairs neighbors to worry about! With its impressive 9-foot-plus ceilings and exposed ductwork, this home exudes a chic, industrial vibe. Right outside your

    Anna Kilty Compass Connecticut, LLC

    92 Main St Unit 107, Deep River, CT 06417
  • /2

    $282,225

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3 Kirtland Ave, Chester, CT 06412

    REO Occupied - NO ACCESS OR VIEWINGS of this property - no interior photos. Please DO NOT DISTURB the occupant. Built in 1974, this one level home offers approximately 1344 finished square feet, two bedrooms and two full baths, fireplace, unfinished basement and attached one car garage. This home sits on an approximate 14810 sqft lot. "As is" cash only sale with no contingencies or inspections.

    Sherry Price Realhome Services & Solutions

    3 Kirtland Ave, Chester, CT 06412
  • /37

    $2,100,000

    • 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
  • /9

    $450,000

    • 2 Beds
    • 1 Bath
    • 1,006 Sq Ft

    85 River Rd Unit M4, Essex, CT 06426

    River views from your living room, primary bedroom and patio. Meticulously maintained two bedroom ground floor unit. Brick fireplace with lovely wood mantelpiece surround. Kitchen updates include granite countertops, newer appliances and open plan with large island. Bathroom entry from primary bedroom has larger door and level shower handicap access. Patio with brick and flagstone has water view.

    Louisa Ketron Berkshire Hathaway NE Prop.

    85 River Rd Unit M4, Essex, CT 06426
  • /35

    $399,900

    • 4 Beds
    • 1.5 Baths
    • 1,664 Sq Ft

    41 Roberts Rd, Westbrook, CT 06498

    Welcome to 41 Roberts Road, a wonderful opportunity to create your ideal shoreline retreat. Situated on 1.84 private acres at the end of a quiet cul-de-sac, this 4-bedroom, 1.5-bath home offers over 1,600 square feet of living space and endless potential for customization. Whether you're looking for a year-round residence, vacation getaway, or investment opportunity, this property provides the

    Cheryl Cook Re/Max Valley Shore

    41 Roberts Rd, Westbrook, CT 06498
  • /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
  • /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
  • /37

    $525,000

    • 3 Beds
    • 2 Baths
    • 1,188 Sq Ft

    135 Middlesex Ave, Chester, CT 06412

    Beautiful view from this WATERFRONT home on Chester Cove! Steps to fishing or kayaking just out your door. Enjoy watching the wildlife from the 20x10 deck directly off the kitchen/dining/living rooms. Wonderful light enters through the abundant windows on the first floor with its open floor plan, kitchen with granite, newer appliances and a window over the kitchen sink you won't want to walk away

    Lisa Genovali Re/Max Valley Shore

    135 Middlesex Ave, Chester, CT 06412
  • /40

    $679,900

    • 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
  • /35

    $485,000

    Open Sat 10:30AM - 12:30PM Coming Soon
    • 3 Beds
    • 2 Baths
    • 1,650 Sq Ft

    216 Reservoir Rd, Killingworth, CT 06419

    Cape Cod with coastal perks, offers 3 bedrooms and 2 full baths. Open floor plan of main level includes a large eat in kitchen with slider to to small balcony/deck overlooking woodland. Alternatively, off of the kitchen is a sizable three season screened porch with vaulted ceiling that overlooks the back yard to create a perfect place for alfresco dining or a simple unwind. Relax in the cozy

    Paul Smyth William Pitt Sotheby's Int'l

    216 Reservoir Rd, Killingworth, CT 06419
  • /33

    $449,000

    • 4 Beds
    • 2 Baths
    • 1,430 Sq Ft

    88 Ironworks Rd, Clinton, CT 06413

    This well designed ranch style home offers the ease of one floor living with an open layout that feels both comfortable and functional. Hardwood floors run throughout creating a warm and inviting flow from room to room. The remodeled kitchen brings a fresh, updated feel to the heart of the home and opens seamlessly into the main living and dining spaces. Just off the back, a spacious deck

    Alan Spotlow William Raveis Real Estate

    88 Ironworks Rd, Clinton, CT 06413
  • /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
  • /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
  • /23

    $455,000

    $20K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,375 Sq Ft

    85 River Rd Unit B7, Essex, CT 06426

    Welcome to Heritage Cove and a rare opportunity. Unit B-7 in the desirable B building is on the market. Three story, three-bedroom townhouse has been owned by the same family since the earliest days of Heritage. Bring your decor ideas to this exceptionally located property. It is very unusual to find a legitimate three-bedroom condominium. This unit offers sweeping views of North Cove and the

    Patrick Kilty William Raveis Real Estate

    85 River Rd Unit B7, Essex, CT 06426
  • /36

    $739,900

    • 3 Beds
    • 2 Baths
    • 2,651 Sq Ft

    67 Break Neck Hill Rd, Westbrook, CT 06498

    Welcome to the Treehouse. Literally and figuratively. A suspension bridge leads to a custom treehouse hidden among the trees, and that's only the beginning! Set on 4.5 private wooded acres just minutes from Connecticut's shoreline, this completely custom full-round log home offers the feeling of a mountain retreat with the convenience of the coast. Surrounded by mature trees, rock outcroppings,

    Carl Guild Carl Guild & Associates

    67 Break Neck Hill Rd, Westbrook, CT 06498
  • /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
  • /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
  • /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
  • /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
  • /40

    $899,900

    $50K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,782 Sq Ft

    16 Glen Grove Rd, Deep River, CT 06417

    16 Glen Grove Road....a stunning custom built 2023 Colonial privately set on 4.53 acres in desirable Deep River. Tucked well off the road and surrounded by beautiful stone walls, this property offers exceptional privacy and endless possibilities to enjoy the outdoors, from garden areas & gorgeous rock walls, to creating your own walking trails throughout the wooded landscape. Inside, you'll find

    Sara Tufano Real Broker CT, LLC

    16 Glen Grove Rd, Deep River, CT 06417
  • /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
  • /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
  • /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
  • /17

    $589,000

    $10K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,594 Sq Ft

    46 School Hill Ln, Westbrook, CT 06498

    Welcome to 46 School Hill Ln, a spacious 4-bedroom, 2.5-bath home offering 2,594 sq ft of comfortable living space. The kitchen features white tile, Corian countertops, and a butcher block center island, perfect for everyday living and entertaining. The primary bath has been refreshed with new flooring and a new vanity. Major systems have been well maintained, including HVAC repairs completed

    Derek Greene Derek Greene

    46 School Hill Ln, Westbrook, CT 06498
  • /30

    $299,000

    • Land
    • 4.49 Acres
    • $66,592 per Acre

    4 Laurel Ln, Clinton, CT 06413

    Build Your Dream Home on 4.49 Acres of Privacy and Natural Beauty! Nestled in a serene wooded setting, this exceptional 4.49-acre property offers a rare opportunity to bring your vision to life. With key site improvements already in place-including a driveway, existing foundation for approximately a 2,000 sq. ft. home, septic system, well, and a charming bridge crossing a gentle brook-this parcel

    Jules Gaughran - Etes William Pitt Sotheby's Int'l

    4 Laurel Ln, Clinton, CT 06413

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