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

  $1,900,000

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

  47 E Kings Hwy, Chester, CT 06412

  The Johnathan Warner house, and later known as the Warner-Brooks House was built by Johnathan Warner in 1798 and is a remarkable testament to early American prosperity, craftsmanship, and vision. Listed on the National Register of Historic Places, this exceptional Federal-style residence retains extraordinary architectural integrity. Heavily documented during construction are original bills,

  

  Al Chiarito

  Chiarito Real Estate LLC

  47 E Kings Hwy, Chester, CT 06412
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  /33

  $675,000

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,156 Sq Ft

  340 Toby Hill Rd, Westbrook, CT 06498

  Welcome home to this classic colonial beautifully situated in a serene Westbrook setting! Conveniently located just north of Route 95, this property offers the ultimate blend of peaceful privacy and prime accessibility, putting you just an 8-minute drive from the beautiful Connecticut shoreline and local beaches, as well as being close to shopping centers and schools. Set back from the road and

  

  Cory Tyler

  Berkshire Hathaway NE Prop.

  340 Toby Hill Rd, Westbrook, CT 06498
• 

  

  

  /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
• 

  

  

  /40

  $1,450,000

  • 4 Beds
  • 4.5 Baths
  • 4,621 Sq Ft

  8 Lindera Ln, Clinton, CT 06413

  Welcome to 8 Lindera Lane, an exceptional private retreat set on nearly nine acres within desirable Houpert's Landing. At the heart of the home is a beautifully appointed kitchen, anchored by an impressive oversized granite island with abundant seating, generous cabinetry and expansive workspace, creating a natural gathering place for both everyday living and entertaining. Outdoors, the property

  

  Tammy Tinnerello

  William Pitt Sotheby's Int'l

  8 Lindera Ln, Clinton, CT 06413
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  /38

  $499,900

  • 3 Beds
  • 2 Baths
  • 1,774 Sq Ft

  55 Wig Hill Rd, Chester, CT 06412

  Set in the charming town of Chester, this three-bedroom, two-bath home offers a versatile layout with thoughtfully updated spaces throughout. The main level features an updated kitchen, wood floors, and an inviting living room anchored by a striking raised gas fireplace that serves as a beautiful focal point. Recent improvements include a new roof and new central air conditioning condenser,

  

  Kelly Puorro

  Puorro Realty Group

  55 Wig Hill Rd, Chester, CT 06412
• 

  

  /38

  $585,000

  • 4 Beds
  • 2 Baths
  • 2,523 Sq Ft

  24 Long Hill Rd, Deep River, CT 06417

  Generous proportions, versatile living spaces and exceptional outdoor amenities define this beautifully appointed four-bedroom, two-bath split-level ranch. The open-concept kitchen, living and dining areas feature hardwood floors, creating an inviting and connected main living space. A fireplace anchors the living room, while the kitchen features stainless steel appliances, including a Sub-Zero

  

  Kelly Puorro

  Puorro Realty Group

  24 Long Hill Rd, Deep River, CT 06417
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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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  /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
• 

  

  /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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  /8

  $928,000

  Open House 10/03 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 2,950 Sq Ft

  60 Bushy Hill Rd, Ivoryton, CT 06442

  Born in 1835. Reimagined for life today. Expanded to over 2,950 sq. feet, the new floor plan emphasizes light, proportion, and seamless flow from one room to the next. At its center, a beautifully composed chef's kitchen pairs a waterfall island with white cabinetry and an oversized walk-in pantry, making entertaining feel wonderfully uncomplicated. The adjoining vaulted great room is the home's

  Patsy Metcalf Compass Connecticut, LLC

  60 Bushy Hill Rd, Ivoryton, CT 06442
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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
• 

  

  /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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  /2

  $769,000

  Open House 10/03 Coming Soon

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

  103 Bushy Hill Rd, Deep River, CT 06417

  Coming soon! This Stunning, completely remodeled ranch style home is truly move in ready! With an open concept living area, perfect for entertaining or everyday living. There is pleanty of kitchen space with an island, new cabinets & quartz countertops and new appliances, living room area with gas fireplace and dining space. High ceilings and plenty of window to let in the natural light. On one

  Kellie Kubica Better Homes and Gardens Real Estate Executive Real Estate

  103 Bushy Hill Rd, Deep River, CT 06417
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  /38

  $439,900

  $35K PRICE DROP

  • 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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  /34

  $2,200,000

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

  88 N Main St, Essex, CT 06426

  Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40

  Kirsten Adams William Pitt Sotheby's Int'l

  88 N Main St, Essex, CT 06426
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  /30

  $284,900

  • 3 Beds
  • 1 Bath
  • 1,217 Sq Ft

  92 Water St, Chester, CT 06412

  Charming 1927 Colonial offering a rare chance to own directly on the water in the heart of Chester. This 3-bedroom, 1-bath home spans 1,217 sq ft across two stories, with a classic layout featuring a living room and dining room on the main level and three bedrooms upstairs. Set on a 0.27-acre lot with vinyl siding and a paved driveway, the home sits right on the water with tranquil river views -

  Ryan O'Keeffe Salzillo Realty Company

  92 Water St, Chester, CT 06412
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  /39

  $769,000

  $26K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,547 Sq Ft

  Unlisted Address

  A truly one-of-a-kind, architecturally designed home offering the perfect blend of luxury, privacy, and functionality. Approximately 2,550 square feet of first-floor living space and over 3,100 square feet of total finished living area. The modern open-concept floor plan is enhanced by soaring 10 to 12-foot ceilings throughout, creating an airy and inviting atmosphere. The gourmet kitchen is

  Alison Perrelli Coldwell Banker Realty

  Unlisted Address
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  /37

  $559,000

  • 3 Beds
  • 3 Baths
  • 1,740 Sq Ft

  28 Deep Hollow Rd, Chester, CT 06412

  This beautifully maintained 1890 Farm House in coveted Deep Hollow Road is a rare opportunity and has been a labor of love over the time that the sellers have lived here. This 1.04 acre property on "The Hollow" consists of a house, an oversized 24' x 24' garage/shop, antique "pony" barn with authentic outhouse and custom built service barn suited for a man cave, cigar lounge or whatever else you

  Tom Pentalow Property Shoppe, LLC

  28 Deep Hollow Rd, Chester, CT 06412
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  /38

  $2,995,000

  • 4 Beds
  • 6 Baths
  • 4,926 Sq Ft

  288 Middlesex Ave, Chester, CT 06412

  Set along a coveted and historic stretch of the Connecticut River, East View is a rare waterfront compound where extraordinary frontage, architectural integrity and Connecticut River Valley charm converge. Just over one mile from the village, this turnkey 2.65-acre estate offers 285 feet of direct river frontage, protected views and deep-water access. The river is the focal point framed by

  Nancy Mesham Coldwell Banker Realty

  288 Middlesex Ave, Chester, CT 06412
• 

  

  /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
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  /36

  $1,495,000

  $100K PRICE DROP

  • 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
• 

  

  /23

  $2,750,000

  • 3 Beds
  • 5 Baths
  • 4,711 Sq Ft

  150-1 Mitchell Hill Rd, Lyme, CT 79532

  UNIQUE and AMAZING! Step into a storybook estate where grandeur meets modern luxury. Set on an expansive 22.92 acres, this castle-inspired residence offers a rare blend of timeless architecture and exceptional comfort. Inside, a breathtaking living room welcomes you with soaring beam-lined ceilings and a massive stone fireplace that anchors the space in warmth and character. The heart of the home

  Cynthia Bahl Anchor Real Estate LLC

  150-1 Mitchell Hill Rd, Lyme, CT 79532
• 

  

  /40

  $349,900

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,006 Sq Ft

  85 River Rd Unit E8, Essex, CT 06426

  Welcome home to low-maintenance riverfront living in desirable Essex, CT! Tucked away in the sought-after Heritage Cove community, this 2-bedroom end-unit offers 1,006 sq. ft. of light-filled, open-concept space featuring scenic water views and easy coastal living. Key Features & Interior Details Living Area: 1,006 sq. ft. open floor plan Bedrooms / Bathrooms: 2 Spacious Bedrooms | 1 Full Bath

  Brian Hammett Hammett Real Estate

  85 River Rd Unit E8, Essex, CT 06426
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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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  /30

  $2,120,000

  • 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
• 

  

  /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
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  /40

  $799,000

  $51K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 4,296 Sq Ft

  10 Shelter Rock Rd, East Haddam, CT 06423

  A private approach leads to this refined colonial home, set on more than four secluded acres. Now offered at a newly reduced price, the property features 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

  Bill Moore Coldwell Banker Realty

  10 Shelter Rock Rd, East Haddam, CT 06423
• 

  

  /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
• 

  /2

  $325,000

  Coming Soon Pre-Foreclosure

  • 3 Beds
  • 1 Bath
  • 1,170 Sq Ft

  33 Acorn Rd, Deep River, CT 06417

  **INVESTOR * CONTRACTOR * HANDYMAN OPPORTUNITY COMING SOON - Welcome to 33 Acorn Road, Deep River- a property with plenty of potential for the buyer ready to roll up their sleeves and bring their vision to life. This is a true handyman/renovation opportunity. The property needs work and updating, but the asking price reflects the condition and the improvements needed, giving the right buyer an

  Terry McDonald McDonald Real Estate, LLC

  33 Acorn Rd, Deep River, CT 06417
• 

  

  /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

  Laura Cariati William Raveis Real Estate

  0 Kelseytown Bridge Rd, Clinton, CT 06413
• 

  

  /40

  $6,595,000

  $1M PRICE DROP

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

  175 River Rd, Essex, CT 06426

  A rare opportunity to own a meticulously designed enclave set on nearly three private acres overlooking the Connecticut River. The main house has over 4600 square feet of beautifully scaled living space with elegant architectural finishes throughout. The first floor features a welcoming entryway which leads to a well-equipped kitchen, breakfast room, formal dining room, and both a living room and

  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
• 

  

  /39

  $824,900

  • 4 Beds
  • 3.5 Baths
  • 2,706 Sq Ft

  275 W Main St, Chester, CT 06412

  Completely Reimagined 4 Bedrooms, 3.5 Bathrooms, 2 Acres, Luxury Primary Suite, Finished Lower Level. This classic New England charm meets a stunning, comprehensive renovation. Directly across from Cockaponset State Forest, this exceptional Chester home has been thoughtfully transformed to deliver modern luxury, comfort, and effortless turnkey living. From the moment you step inside, you'll

  Shirley Tapper Great Estates, CT

  275 W Main St, Chester, CT 06412
• 

  

  /40

  $3,950,000

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

  274 Joshuatown Rd, Lyme, CT 06371

  A rare modern retreat - where extraordinary design meets an unexpected sense of warmth and ease. Privately set above the Connecticut River, 274 Joshuatown Road is remarkable for how beautifully it lives; intimate, inviting, and deeply connected to its natural surroundings. A long, private drive creates a profound sense of arrival, revealing a residence thoughtfully positioned to capture sweeping

  Margaret Douglas William Raveis Real Estate

  274 Joshuatown Rd, Lyme, CT 06371
• 

  

  /30

  $249,000

  $50K PRICE DROP

  • Land
  • 4.49 Acres
  • $55,457 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. The babbling brook, a tributary of the Indian River, winds gracefully through the landscape, enhancing the property's peaceful, storybook charm. Surrounded by mature trees, this property offers the

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

  4 Laurel Ln, Clinton, CT 06413
• 

  /2

  $2,200,000

  • Land
  • 30 Acres
  • $73,333 per Acre

  134 Meadow Woods Rd, Deep River, CT 06417

  Rare opportunity to acquire approximately 30 acres in one of Deep River's most desirable locations. This exceptional property presents a unique residential development opportunity combining privacy, natural beauty, existing improvements, and future potential. The property includes an existing Saltbox style residence and offers subdivision potential for approximately 5-7 residential lots, subject

  Jennifer Gurnell William Raveis Real Estate

  134 Meadow Woods Rd, Deep River, CT 06417

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