Homes for Sale in Connecticut - Historic

• 

  

  

  /35

  $785,000

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft

  16 River Rd, Sharon, CT 06069

  Picture starting your morning watching the sun rise over the water and ending your day with peaceful river views from almost every room in your home. Set on 2 acres along the majestic Housatonic river near Cornwall Bridge, 16 River Road has been completely transformed by a major renovation in 2024 into a modern waterfront sanctuary, while keeping its timeless antique character intact. Inside,

  Alan O'Doherty William Pitt Sotheby's Int'l

  16 River Rd, Sharon, CT 06069
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  /40

  $4,250,000

  $245K PRICE DROP

  • 10 Beds
  • 7 Baths
  • 12,145 Sq Ft

  117 Water St, Stonington, CT 06378

  Ocean House is an eleven unit, mixed use, historic property, comprised of seven residential suites and four commercial suites. The cornerstone of Stonington Borough's commercial Village District, each of the occupied, renovated residential suites features a fully applianced kitchen with dishwasher and a private laundry. Each of the four commercial spaces offer off-the-sidewalk entry and glass bay

  Lori Hopkins-Cavanagh Lori Hopkins-Cavanagh Broker

  117 Water St, Stonington, CT 06378
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  /40

  $1,499,000

  $100K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,168 Sq Ft

  677 N Salem Rd, Ridgefield, CT 06877

  Rarely does a property of this character and versatility come to market. Welcome to 677 N Salem Road - known historically as the Jamesway Barn Estate - a truly singular 2-acre compound in the heart of Ridgefield that blends 19th-century craftsmanship with extraordinary potential. The main Colonial residence is a diamond in the rough, offering 3 bedrooms, rich wide-plank hardwood floors, two

  Stephen Mele Houlihan Lawrence

  677 N Salem Rd, Ridgefield, CT 06877
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  /36

  $359,900

  • 3 Beds
  • 3 Baths
  • 2,072 Sq Ft

  475 W Woods Rd, Hamden, CT 06518

  Come home to this well-maintained colonial that blends historic charm and modern updates. With a separate detached in-law suite and driveway, this property is perfect for generating rental income or generational living. Built on what was once a fruit farm, this home boasts thoughtful updates such as a recently replaced roof (2022), central air conditioning/forced air heating (2022), and beautiful

  Kevin Kennedy Coldwell Banker Realty

  475 W Woods Rd, Hamden, CT 06518
• 

  

  

  /40

  $449,900

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

  323A Gallup Hill Rd, Ledyard, CT 06339

  Nestled in private woods, this commanding 3,456-sq.ft contemporary home offers peaceful seclusion close to coastal CT. Situated on 4.2 forested acres at the end of a long private driveway, this property is a true sanctuary. Offered AS-IS, this spacious residence awaits your custom renovation-the perfect blank canvas for your dream home. The upper main living level features an open layout with

  Michael Tomaszek Garden Realty

  323A Gallup Hill Rd, Ledyard, CT 06339
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  /40

  $10,995,000

  $1M PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,560 Sq Ft

  123 Saddle Rock Rd, Stamford, CT 06902

  Surrounded by the Long Island Sound on three sides, this extraordinary waterfront compound has defined the southern tip of Shippan Point for more than a century. Set on a private peninsula, it offers the rare privilege of watching the sun rise over the Sound and set back into the water with the Manhattan skyline shimmering in the distance. Designed by Hunt & Hunt Architects and completed in 1914

  Leslie McElwreath Sotheby's International Realty

  123 Saddle Rock Rd, Stamford, CT 06902
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  /40

  $1,900,000

  • 4 Beds
  • 4 Baths
  • 3,392 Sq Ft

  31 Splitrock Rd, Norwalk, CT 06854

  Absolutely amazing mid century modern waterfront home. Located in the historic Village Creek community, this renovated home offers lovely and serene water views from every room. Perched higher in the neighborhood, there is no flood insurance required. So many special features highlight this home including a dramatic sun drenched open floor plan encased in floor to ceiling windows and stone

  Nancy Manby William Raveis Real Estate

  31 Splitrock Rd, Norwalk, CT 06854
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  /31

  $725,000

  • 5 Beds
  • 3 Baths
  • 1,365 Sq Ft

  50 Southbury Rd, Roxbury, CT 06783

  Cottage & Guest House Located in pastoral Southern Roxbury, just 90 minutes from New York City. Set on 2 acres, the property features a historic c.1817 three-bedroom antique cape-featured in Elle Decor-a charming two-bedroom guest house. The main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls and it has

  Jeff Phillips William Pitt Sotheby's Int'l

  50 Southbury Rd, Roxbury, CT 06783
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  /40

  $1,250,000

  $49K PRICE DROP

  • 3 Beds
  • 6 Baths
  • 6,312 Sq Ft

  116 S Main St, Wallingford, CT 06492

  Rare opportunity to own a unique mixed use property in the heart of Wallingford. The main residence is a charming and beautifully maintained home offering 3614sqft of living space, with flexibility for a home office or professional use. Features include an updated kitchen, inviting sitting room, spacious living room, formal dining room, first floor living room and 3 bedrooms. The 3rd floor

  Dana Longley Coldwell Banker Realty

  116 S Main St, Wallingford, CT 06492
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  /36

  $795,000

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft

  51 Mill St, Riverton, CT 06065

  Introducing: Fawns Leap, a masterclass in historic preservation. Following an exhaustive, $1.5 million meticulous restoration, this property offers a rare real estate dream: the undeniable charm and soul of an antique home, with absolutely none of the discomforts, drafts, or maintenance costs of one. Stripped down to the studs and thoughtfully rebuilt, the exterior boasts completely new

  John Harney William Pitt Sotheby's Int'l

  51 Mill St, Riverton, CT 06065
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  /38

  $219,000

  • 2 Beds
  • 2 Baths
  • 1,073 Sq Ft

  839 Main St Unit 84, Torrington, CT 06790

  Today is a special day! A rare oppurtunity awaits you! Unit #84 at Warrenton Mills is now offered for sale! This property is unique in so many ways! It actually is one of the two units at Warrenton with a two bedroom/two level/two full bath floor plan! Being it is on the upper level of the North Mill building, it has the full length skylights that this complex is known for! This historic saw

  Robert Ficks Berkshire Hathaway NE Prop.

  839 Main St Unit 84, Torrington, CT 06790
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  /26

  $1,075,000

  Coming Soon

  • 12 Beds
  • 6 Baths
  • 5,763 Sq Ft

  63 Whitmore St, Hartford, CT 06114

  CORE INCOME-PRODUCING ASSET, Fully Renovated Six-Unit Multifamily | Established Short-Term Rental Operation. A compelling acquisition opportunity in Hartford's Historic South End. Featuring a fully renovated brick six-family property accompanied by an established furnished Airbnb operation. The asset consists of six 2-bedroom, 1-bath residences, upgraded throughout with contemporary kitchens,

  Andrea Rodriguez Eagle Eye Realty PLLC

  63 Whitmore St, Hartford, CT 06114
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  /39

  $520,000

  $29K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft

  101 Child Hill Rd, Woodstock, CT 06281

  Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases

  Kristen Kaskela Berkshire Hathaway NE Prop.

  101 Child Hill Rd, Woodstock, CT 06281
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  /6

  $750,000

  $151K PRICE INCREASE

  • Land
  • 29.2 Acres
  • $25,685 per Acre

  00 Above All Rd, Warren, CT 06754

  29.20 acres of unspoiled beauty for sale in historic Warren, Connecticut - one of the oldest towns in Connecticut, first settled in 1737. The property has been in the same family since the1800's. This woodland parcel is located on a quiet dead-end road and gives one the chance to build a retreat in a small country farming community. It offers access to power lines as well as substantial road

  John Sniffen William Pitt Sotheby's Int'l

  00 Above All Rd, Warren, CT 06754
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  /6

  $239,986

  $146K PRICE DROP

  • Land
  • 1.91 Acres
  • $125,647 per Acre

  00 Main St, Winsted, CT 06098

  Exceptional 2+ Acre Development Opportunity - Route 44, Winsted, CT** Rare opportunity to acquire approximately 2+- acres with nearly 700 feet of frontage on Main Street (Route 44), one of Winsted's primary commercial corridors. Located within the Town Gateway Zone, this highly visible parcel offers outstanding flexibility for a variety of development opportunities, including commercial,

  Dan Merrigan Merrigan & Lefebvre Realty

  00 Main St, Winsted, CT 06098
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  /40

  $1,295,000

  • 6 Beds
  • 5.5 Baths
  • 4,258 Sq Ft

  201 Route 37 S, Sherman, CT 06784

  Tucked back from the road behind a privacy screen of mature evergreens on almost an acre and a half of level property, is the c. 1862 Charles A. Briggs House-famously known as the Timber Trails Inn of the early 1900s. This historic Sherman landmark has been thoughtfully modernized to pair 19th-century soul with 21st-century luxury. Antique wide-board floors, authentic exposed beams, and original

  Mary Worstell Real Property Purveyors Inc

  201 Route 37 S, Sherman, CT 06784
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  /38

  $2,550,000

  • 6 Beds
  • 5 Baths
  • 3,669 Sq Ft

  44 Williams Ave, Stonington, CT 06355

  A turn-key investment opportunity in the heart of Mystic. This completely updated multi-unit building blends coastal sophistication with a high-yield asset model, making it a true trophy property for your portfolio. In the LS-5 zone, it is positioned perfectly for an owner occupier on the second floor with rental units for the modern traveler on the first level. Or, use all units as long-term

  Jonathan Shockley Serhant Connecticut, LLC

  44 Williams Ave, Stonington, CT 06355
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  /38

  $599,900

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

  187 Whitehall Ave, Stonington, CT 06355

  Victorian charm, modern updates, and investment potential come together at 187 Whitehall Ave in Old Mystic. Set on just under an acre, this character-filled three-bedroom, two-full-bath home offers tremendous versatility for an owner-occupant, investor, or those seeking a flexible multi-generational setup. Timeless on the outside and thoughtfully refreshed within, the home preserves its historic

  Stephano Stravoravdis Real Broker CT, LLC

  187 Whitehall Ave, Stonington, CT 06355
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  /38

  $899,000

  $76K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 3,745 Sq Ft

  390 Three Mile Rd, Glastonbury, CT 06033

  This extraordinary custom residence seamlessly blends timeless elegance with relaxed sophistication. Originally a log cabin and thoughtfully reimagined into a luxurious estate, the home showcases exceptional craftsmanship, distinctive architectural details, and premium finishes throughout. A stunning wraparound porch with rich mahogany flooring and beadboard ceilings creates an inviting first

  Thomas Simjian Keller Williams Coastal

  390 Three Mile Rd, Glastonbury, CT 06033
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  /40

  $599,900

  $50K PRICE DROP

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

  25 Old Turnpike Rd, Storrs Mansfield, CT 06268

  A rare blend of historic charm and modern craftsmanship, the beloved "Ash House" offers an exceptional living experience along one of Mansfield's designated scenic roadways. Originally built circa 1732, the saltbox colonial was meticulously dismantled, preserved, and rebuilt on its current 2.5 acre setting. Completed in 2013, this "new antique home" honors its heritage while providing the

  Lindsey Niarhakos RE/MAX One

  25 Old Turnpike Rd, Storrs Mansfield, CT 06268
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  /40

  $7,900,000

  • 7 Beds
  • 9 Baths
  • 8,100 Sq Ft

  246 Brookside Rd, Darien, CT 06820

  Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and

  Keiley Fuller Compass Connecticut, LLC

  246 Brookside Rd, Darien, CT 06820
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  /40

  $839,000

  • 6 Beds
  • 3.5 Baths
  • 5,109 Sq Ft

  45 Huntington Ave, Norwich, CT 06360

  Nestled in history and beautifully preserved, the E.A. Huntington Homestead c.1717 offers a rare opportunity to own one of Norwichtown's most distinctive properties. Set among mature trees, historic stone walls, and peaceful grounds, this remarkable estate features over 5,100 square feet of living space between the main residence and detached guest house. The main home showcases original

  Brian Mason eXp Realty

  45 Huntington Ave, Norwich, CT 06360
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  /40

  $1,085,000

  $105K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  120 Ivy Hill Rd, Ridgefield, CT 06877

  Welcome to effortless luxury living in the heart of Ridgefield. This stunning newly constructed home offers 2,900 square feet of thoughtfully designed living space, blending timeless elegance with modern convenience just minutes from Ridgefield's celebrated historic downtown. A welcoming front foyer sets the tone for the home. The kitchen is appointed with Bosch appliances, quartz countertops, a

  Kelley Vanacore Century 21 AllPoints Realty

  120 Ivy Hill Rd, Ridgefield, CT 06877
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  /40

  $365,000

  • 3 Beds
  • 2 Baths
  • 2,318 Sq Ft

  207 Summit St, Willimantic, CT 06226

  Step into a truly one-of-a-kind home where history, character, and creativity come together. Originally built circa 1892 as the historic Hilltop Hose Company No. 3 Firehouse, this remarkable property has been thoughtfully transformed into an eclectic single-family residence while honoring its architectural roots. The 1,000-square-foot first floor offers an expansive open layout with soaring

  Sue Esposito Home Selling Team

  207 Summit St, Willimantic, CT 06226
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  /21

  $629,900

  • 5 Beds
  • 2.5 Baths
  • 2,986 Sq Ft

  317-319 Garden St, Wethersfield, CT 06109

  Calling all owner occupants and investors!! Incredibly rare opportunity to own a two-family located in historic Old Wethersfield within walking distance of Village district, Hanmer Elementary school, park, farmer's market and Wethersfield Cove! This asset features an updated first floor two bedroom unit leased at $2,150 until 6/30/27! Vacant three bedroom unit consists of combined second and

  Matthew Guida Eagle Eye Realty PLLC

  317-319 Garden St, Wethersfield, CT 06109
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  /25

  $675,000

  • 2 Beds
  • 1 Bath
  • 1,402 Sq Ft

  71 Hospital Hill Rd, Sharon, CT 06069

  This c. 1880 Colonial is nestled in the heart of the Village of Sharon. Thoughtfully restored from top to bottom, it is a truly turnkey offering that seamlessly blends Founding Era character with modern comfort. Inside, warm, inviting living spaces are filled with natural light and include a well-appointed kitchen with breakfast nook, two bedrooms, one beautifully finished bath, a living room and

  Dan Kessler Compass Connecticut, LLC

  71 Hospital Hill Rd, Sharon, CT 06069
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  /8

  $925,000

  • Land
  • 12.4 Acres
  • $74,597 per Acre

  30 Blackledge Dr, Marlborough, CT 06447

  Ample space to build your dream home! Quiet, peaceful surrounded by state forest, the Blackledge River, few neighbors. Subdivision maps are available. Current home sits on 1.84 acre parcel, remaining 10+ acres are considered lot#2. A historic building sits in the middle, once known as The Red Dog - a local watering hole way back when! Perc test was done many years ago.

  Zina Planeta Coldwell Banker Realty

  30 Blackledge Dr, Marlborough, CT 06447
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  /31

  $499,000

  $16K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,490 Sq Ft

  31 N Stonington Rd, Mystic, CT 06355

  Take a look at this beautiful historic home dating back to the 1700s, nestled in the charming coastal town of Mystic, Connecticut! If you love the warmth and character of a country home with exposed beams, wide-plank floors, and cozy fireplaces, this one is worth seeing in person. Situated on approximately half an acre, the property also offers additional yard space and a large clearing behind

  Luis Pagan RE/MAX One

  31 N Stonington Rd, Mystic, CT 06355
• 

  

  /40

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 3,276 Sq Ft

  85 Tolland Green, Tolland, CT 06084

  Step into a remarkable piece of history with this 3,276 sq. ft. Colonial, built in 1791, offering 3 bedrooms, 2.5 bathrooms and an incredible blend of timeless character and comfortable living. Beautiful wide-plank wood floors, original architectural details, rich woodwork and multiple fireplaces showcase the warmth and history found throughout this distinctive home. The first floor features an

  Pamela Moriarty Coldwell Banker Realty

  85 Tolland Green, Tolland, CT 06084
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  /23

  $765,000

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,862 Sq Ft

  3 Hall Rd, Hebron, CT 06248

  Introducing a beautiful new construction Colonial to be built on a fully approved, shovel-ready homesite in one of Hebron's most desirable locations. This thoughtfully designed home will feature 9-foot ceilings, an open-concept layout, a stunning kitchen with quartz/granite countertops, stainless steel appliances, tile backsplash, solid oak hardwood flooring, a sunroom, rear patio, full basement,

  Robyn Letourneau Berkshire Hathaway NE Prop.

  3 Hall Rd, Hebron, CT 06248
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  /21

  $2,995,000

  New Construction

  • 1 Bed
  • 1.5 Baths
  • 1,443 Sq Ft

  77 Beaver Dam Rd, Salisbury, CT 06068

  A Premier Estate Parcel Ready for Immediate Construction This exceptional 33.9 acre property on Beaver Dam Road-one of the most scenic addresses in Salisbury-offers a rare opportunity to create a private estate of lasting beauty and value. Surrounded on two sides by protected land, the property enjoys a remarkable sense of privacy and quiet, while being just minutes from the town center. The land

  Elvia Gignoux William Pitt Sotheby's Int'l

  77 Beaver Dam Rd, Salisbury, CT 06068
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  /40

  $1,825,000

  • 5 Beds
  • 9 Baths
  • 5,414 Sq Ft

  173 Highwoods Dr, Guilford, CT 06437

  A LEGENDARY GUILFORD ESTATE-where extraordinary history, artistry, architecture, & modern luxury converge. One of New England's most exceptional restorations, the Pitkin House is a remarkable 18th-century treasure set privately on nearly 4 acres of mature trees, stone walls, manicured lawns, enchanting gardens, & extraordinary recreational amenities. Originally constructed in East Hartford, the

  Kiara Rusconi William Raveis Real Estate

  173 Highwoods Dr, Guilford, CT 06437
• 

  

  /31

  $284,999

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,624 Sq Ft

  82 Porter St, Watertown, CT 06795

  100% PRE-INSPECTED, REMEDIATED, & PRICED TO MOVE: $284,999. Anchored on an expansive, sun-drenched 0.52-acre level parcel, 82 Porter Street delivers classic 1919 New England architecture paired with the heavy lifting modern buyers demand. Offering 3 Bed, 1 bath, 1,624 SF of continuous, light-filled above-grade living space-now completely cleared, vacant, and primed for your bespoke vision. THE

  Steve Schappert Connecticut Real Estate

  82 Porter St, Watertown, CT 06795
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  /39

  $1,200,000

  Open Sat 1PM - 3PM

  • 4 Beds
  • 4 Baths
  • 4,200 Sq Ft

  391 Kent Cornwall Rd, Kent, CT 06757

  A Kent Landmark, Reimagined - This historic converted dairy barn offers 3,600 sq ft of flexible living space on over 14 private acres, with direct Housatonic River frontage and protected land trust borders. Hand-hewn beams, cathedral ceilings, and skylights carry the property's history throughout; while a converted silo houses a home office, art studio and gym. The sunny modern kitchen, renovated

  Vanessa Henderson William Pitt Sotheby's Int'l

  391 Kent Cornwall Rd, Kent, CT 06757
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  /25

  $969,000

  $126K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  23 Painter Hill Rd, Roxbury, CT 06783

  Mint Hilltop Home with Views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. New Anderson Luxe White Oak Windows. Wood-Burning Fireplace, Vaulted Primary Bedroom with Balcony and Private Bath. Dine or relax on the Flagstone Terrace. Must See!

  Peter Klemm Klemm Real Estate Inc

  23 Painter Hill Rd, Roxbury, CT 06783
• 

  /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
• 

  

  /40

  $759,000

  • 4 Beds
  • 4.5 Baths
  • 3,696 Sq Ft

  29 Diamond Ln, New Milford, CT 06776

  Welcome to 29 Diamond Lane, a spectacular retreat on 5.74 acres in desirable Merryall neighborhood. Set back from the road, this expansive home offers peace, privacy & a versatile floor plan for a variety of lifestyles. Sunlight pours through new oversized windows, illuminating an open living space w/ beautiful hardwood floors, gas fireplace, custom-built ins & charming breakfast nook. The space

  Laura Testa Kiwi Homes

  29 Diamond Ln, New Milford, CT 06776
• 

  

  /40

  $1,076,000

  • 4 Beds
  • 2 Baths
  • 3,418 Sq Ft

  18 East St, Bethlehem, CT 06751

  Rare Bethlehem Offering - 1740s Antique + Commercial-Ready Barn on 2 Acres Welcome to a rare offering in the heart of Bethlehem, CT, sited at the town's famous blinking light with easy proximity to Washington, Litchfield & Woodbury. Dating to the 1740s, this sensitively preserved 4-bedroom antique is rich with period charm - 5 fireplaces, including a 12' hearth housing a beehive oven, historic

  Brandy Granata Coldwell Banker Realty

  18 East St, Bethlehem, CT 06751
• 

  

  /30

  $489,000

  • 2 Beds
  • 2.5 Baths
  • 1,958 Sq Ft

  69 Sullivan Farm, New Milford, CT 06776

  Tucked away overlooking a peaceful babbling brook/waterfall, this private end-unit in award-winning Sullivan Farm offers the perfect balance of tranquility & community. A charming side porch welcomes you into spacious living areas, including a large eat-in kitchen with a center island topped in striking black granite- ideal for meal prep or gathering with friends. The formal dining room flows

  Lisa Briscoe William Raveis Real Estate

  69 Sullivan Farm, New Milford, CT 06776
• 

  

  /39

  $3,395,000

  • 7 Beds
  • 7 Baths
  • 7,060 Sq Ft

  259 N Main St, Stonington, CT 06378

  Cove Lawn - Historic Italianate Estate with Water Views & Guest House. Walk to Stonington Borough. Experience the charm of village living just moments from Historic Stonington Borough at Cove Lawn, a magnificent c.1860 Italianate estate steeped in local history and timeless elegance. Ideally located just a short stroll to the Borough's deep-water marinas, boutique shopping, seaside cafes, and

  Judi Caracausa William Pitt Sotheby's Int'l

  259 N Main St, Stonington, CT 06378

Showing Results 201 - 240, Page 6 of 13