254

Homes for Sale in Connecticut - Historic

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  • /16

    $950,000

    • 2 Beds
    • 2 Baths
    • 1,135 Sq Ft

    11 Judges Hollow Rd, Fairfield, CT 06824

    Eight minutes from downtown Westport, escape to 11 Judges Hollow-a 1930's rustic hunting cabin on 1.6 private wooded acres at the end of a long secluded driveway. A one of a kind private in holding completely surrounded by the 180 acre Brett Woods Conservation Area, this rare property offers ultimate privacy with protected open space as your permanent neighbor. Judges Hollow is nestled within

    Lisa Hartmann William Pitt Sotheby's Int'l

    11 Judges Hollow Rd, Fairfield, CT 06824
  • /33

    $5,200,000

    • 6 Beds
    • 6 Baths
    • 4,002 Sq Ft

    32 Broadway Ave, Stonington, CT 06378

    This property offers an incredible opportunity to own a small boutique hotel with with upscale rooftop amenities and offering great views of Mystic all while enjoying the rooftop dip pool, sun deck, dining deck and lounge along with elements for a contactless (aka low labor) business model. Located in the heart of Mystic Connecticut, a popular year round and summer resort location, this six suite

    Donna Simmons Mott & Chace Sotheby's Intl Rt

    32 Broadway Ave, Stonington, CT 06378
  • /4

    $1,850,000

    • Land
    • 0.2 Acre
    • $9,250,000 per Acre

    31 Franklin St, Westport, CT 06880

    This transformative site is located on quaint street lined with early 1900s properties in the Historic Saugatuck area of Westport. One block away from train station I-95. Adjacent to the recently developed Saugatuck Center and Saugatuck River with restaurants, Cafes and luxury residential. Potential to acquire adjacent 19 Ketchum that is fully occupied as well as 31 Franklin. Please do not walk

    Peter Lane Ogents, LLC

    31 Franklin St, Westport, CT 06880
  • /28

    $799,000

    • 2 Beds
    • 2 Baths
    • 1,220 Sq Ft

    25 E Shore Rd, New Preston Marble Dale, CT 06777

    Renovated c.1860 cottage set along the East Aspetuck River in the heart of historic New Preston. This charming turnkey, retreat offers 2 bedrooms, 2 expansive bathrooms, and a gourmet kitchen, all complemented by the soothing sounds and views of a nearby waterfall. Relax at the river's edge, gather around the fire pit, or stroll into town to enjoy boutiques, antique shops, wine bar/restaurant,

    Melissa Smith Houlihan Lawrence

    25 E Shore Rd, New Preston Marble Dale, CT 06777
  • /39

    $3,449,000

    • 5 Beds
    • 7 Baths
    • 5,515 Sq Ft

    2683 Bronson Rd, Fairfield, CT 06824

    In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family

    Tara Hawley Coldwell Banker Realty

    2683 Bronson Rd, Fairfield, CT 06824
  • /20

    $499,000

    • Land
    • 8.64 Acres
    • $57,755 per Acre

    200 North St, Roxbury, CT 06783

    ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. THIS IS THE LAST AVAILABLE LOT FROM PHASE II, (LOT #1) AND IT MUST BE SEEN AND HEARD TO UNDERSTAND HOW YOUR FUTURE HEIRLOOM HOME WILL BE

    Jill Sloane Brown Harris Stevens

    200 North St, Roxbury, CT 06783
  • /40

    $7,400,000

    • 7 Beds
    • 7 Baths
    • 6,844 Sq Ft

    102 Melius Rd, Warren, CT 06754

    Reverie Farm is an exceptionally rare late 18th century stone and shingle estate, on more than one hundred acres, located in one of the highest and most private parts of Connecticut. Situated in the heart of Litchfield County, the property rises more than 1,200 feet in elevation across four distinct tax parcels, among which are several estate quality building sites. The setting is dreamlike in

    Andrew Gates Past Member

    102 Melius Rd, Warren, CT 06754
  • /40

    $738,500 Coming Soon

    • 3 Beds
    • 1.5 Baths
    • 1,982 Sq Ft

    6 Pelton Hill Rd, Chester, CT 06412

    Nestled at the end of a peaceful, dead-end street, this beautifully maintained Carpenter Gothic home offers the perfect blend of historic charm and modern comforts. With its unique architectural style and serene private setting, this property is truly a hidden gem. The three Bedrooms are spacious and bright, each bedroom offers a cozy retreat with plenty of natural light and charming details that

    John Zubretsky Century 21 AllPoints Realty

    6 Pelton Hill Rd, Chester, CT 06412
  • /22

    $179,999

    • 1 Bed
    • 1 Bath
    • 636 Sq Ft

    1150 Whitney Ave Unit 5, Hamden, CT 06517

    This beautifully remodeled townhouse-style 1 bedroom condo is the perfect first step into homeownership. Blending historic charm with modern upgrades, the unit has been fully refreshed so you can move right in without the stress of renovations. Enjoy brand new flooring throughout, fresh paint that brightens every room, and updated electrical for safety and peace of mind. The layout offers

    Amber Berry Weichert, Realtors-On The Mark

    1150 Whitney Ave Unit 5, Hamden, CT 06517
  • /35

    $792,000 Open Sat 12PM - 3PM

    • 4 Beds
    • 2 Baths
    • 1,960 Sq Ft

    42 Scodon Dr, Ridgefield, CT 06877

    This beautifully maintained, sun-filled 4-bedroom, 2 full bath Colonial is set on a level 2-acre lot in a highly desirable North Ridgefield neighborhood. Gleaming hardwood floors extend throughout the home. The main level features a spacious, light-filled living room with a cozy wood-burning fireplace, perfect for relaxing or entertaining. The eat-in kitchen opens to sliding doors that lead to an

    Tim Dent Coldwell Banker Realty

    42 Scodon Dr, Ridgefield, CT 06877
  • /34

    $579,000

    • 6 Beds
    • 3 Baths
    • 2,716 Sq Ft

    584 Kossuth St, Bridgeport, CT 06608

    A charming three-family property is now available in the highly desirable Historic East Side of Bridgeport, ideally situated directly across from scenic Washington Park. This stately residence is set on a charming, tree-lined street, offering a perfect blend of urban convenience and neighborhood appeal. Enjoy relaxing evening strolls through the park or along the peaceful surroundings. Each of

    Kathleen Dattilo Lamacchia Realty

    584 Kossuth St, Bridgeport, CT 06608
  • /40

    $1,399,000

    • 4 Beds
    • 3.5 Baths
    • 4,103 Sq Ft

    40 Great Ring Rd, Sandy Hook, CT 06482

    EXCITING NEW LISTING DEVELOPMENT! Now offered independently, with the adjoining land available if desired - two properties, one extraordinary opportunity at 40 Great Ring Road. This modern vision of New England living blends refined architectural character with forward-thinking innovation, energy independence, and sustainable design. The four-bedroom home features a spacious primary suite and

    Stephanie Barnes William Raveis Real Estate

    40 Great Ring Rd, Sandy Hook, CT 06482
  • /40

    $659,000

    • 4 Beds
    • 4 Baths
    • 2,780 Sq Ft

    712 Main St, South Glastonbury, CT 06073

    Welcome to this beautifully restored and fully renovated 1800s antique home, where timeless charm meets modern convenience-allowing you to move right in without lifting a finger. Every detail has been thoughtfully updated while preserving the character and craftsmanship of the era. Major improvements include a new roof, new siding, new boiler, updated electrical & plumbing, many replaced windows

    Lauren Freedman Coldwell Banker Realty

    712 Main St, South Glastonbury, CT 06073
  • /8

    $1,799,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,345 Sq Ft

    41-1 Whippoorwill Rd, Old Lyme, CT 06371

    Nestled in the charming coastal town of Old Lyme, Connecticut, this expansive 3345-square-foot farmhouse offers a perfect blend of rustic elegance and modern comfort. Set on a serene lot, this home welcomes you with its classic New England charm, featuring a sprawling layout designed for both relaxation and entertaining. The first-floor master bedroom is a true retreat, complete with ample space,

    Allyson Cotton William Pitt Sotheby's Int'l

    41-1 Whippoorwill Rd, Old Lyme, CT 06371
  • /24

    $187,720

    • 4 Beds
    • 2.5 Baths
    • 1,984 Sq Ft

    86 Linsley Ave, Meriden, CT 06451

    Back on the market due to buyer's financial issues. Discover the character and opportunity awaiting you at 86 Linsley Avenue, a versatile property located in the heart of Meriden. This home offers a wonderful blend of historic charm and functional living space, perfect for those looking to create their dream residence or expand their investment portfolio. The home's interior is defined by the

    Mark Porriello RE/MAX Right Choice

    86 Linsley Ave, Meriden, CT 06451
  • /16

    $425,000

    • 11 Beds
    • 1.5 Baths
    • 3,748 Sq Ft

    30 Main St, Plainfield, CT 06374

    Nestled in the heart of history, this extraordinary three-level estate exudes timeless elegance and vintage charm. With soaring ceilings, sprawling rooms, and intricate architectural details, this home captures the essence of a bygone era while offering the space and amenities for today's lifestyle. Every corner of this impressive residence tells a story-from the grand entryway with original

    Adam Gonzalez Century 21 Limitless

    30 Main St, Plainfield, CT 06374
  • /40

    $699,000

    • 3 Beds
    • 3.5 Baths
    • 3,210 Sq Ft

    58 Good Hill Rd, Woodbury, CT 06798

    Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming

    Christina Zainc BHGRE Gaetano Marra Homes

    58 Good Hill Rd, Woodbury, CT 06798
  • /5

    $40,000

    • Land
    • 0.25 Acre
    • $160,000 per Acre

    1175 Worthington Ridge, Berlin, CT 06037

    Tired of competing against other buyers and feeling like you're settling for a home you don't really love?!?! Build your own dream home the way you want with the style you want and the finishes you want!! This building lot sits in the lovely historic district of Berlin in a convenient yet quiet neighborhood. Previously approved for a 3/4 bedroom home with gas and public water. Easement -

    Cheryl Bergeron-Lucca LPT Realty - IConn Team

    1175 Worthington Ridge, Berlin, CT 06037
  • /13

    $985,000

    • 3 Beds
    • 2 Baths
    • 1,772 Sq Ft

    179 South St, Roxbury, CT 06783

    Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity

    Kathryn Clair William Pitt Sotheby's Int'l

    179 South St, Roxbury, CT 06783
  • /31

    $3,995,000

    • 6 Beds
    • 5.5 Baths
    • 6,121 Sq Ft

    79 Hilltop Rd, Sharon, CT 06069

    1880's perfection, a true rare find in the heart of Sharon, CT. Magnificent seven bedroom, 5.5 bath estate, beautifully preserved and situated on a sprawling 4-acre lot with a pool. Large eat-in kitchen with massive center island. Screen porch overlooking the pool with beautiful hilltop views. 79 Hilltop masterfully combines historic charm with modern luxury, offering you the best of both worlds.

    Carolyn Morrison William Pitt Sotheby's Int'l

    79 Hilltop Rd, Sharon, CT 06069
  • /36

    $998,000

    • 4 Beds
    • 3.5 Baths
    • 2,964 Sq Ft

    32 Catalpa Rd, Wilton, CT 06897

    Perched on a beautifully terraced 1.51-acre property in Wilton, the historic Louis Warncke House (circa 1909) offers a rare blend of architectural character, warmth, and modern livability. This distinctive residence showcases exceptional craftsmanship throughout, including rich original wood paneling, coffered ceilings, hardwood floors, and striking millwork rarely found in homes today. The main

    Bryan Morris William Pitt Sotheby's Int'l

    32 Catalpa Rd, Wilton, CT 06897
  • /40

    $3,450,000

    • 8 Beds
    • 11 Baths
    • 11,696 Sq Ft

    11 Mountain Spring Rd, Farmington, CT 06032

    Tucked away on over 4.5 private acres off Historic Mountain Spring Road this Georgian inspired estate is an extraordinary example of American architectural heritage. It encompasses over 11,000 square feet of refined living space, offering 8 bedrooms, 7 full baths, and 3 half baths. A majestic Great Hall greets visitors with soaring ceilings and elegant millwork. The residence boasts formal

    Scott Holmes William Pitt Sotheby's Int'l

    11 Mountain Spring Rd, Farmington, CT 06032
  • /12

    $1,195,000

    • 4 Beds
    • 4 Baths
    • 2,392 Sq Ft

    51 Pearl St, Guilford, CT 06437

    Rare opportunity in Guilford! This home is currently used as a multifamily but can revert to a one family residence. Approximately 2400 sqft with the possibility of future expansion. Conveniently located close to Guilford's Historic Green, shops, restaurants, beaches and shoreline attractions.

    Philip Warner William Pitt Sotheby's Int'l

    51 Pearl St, Guilford, CT 06437
  • /40

    $1,199,999

    • 9 Beds
    • 9 Baths
    • 4,982 Sq Ft

    209 Main St, Deep River, CT 06417

    Experience the timeless beauty of New England living! This meticulously restored 1854 Colonial blends historic charm with modern comfort in the heart of Deep River. Every detail has been thoughtfully preserved or reimagined-from the gleaming pumpkin pine wide-plank floors and custom-milled woodwork to carefully selected reproduction hardware that speaks to its heritage. Six fireplaces grace the

    Diane Devries William Pitt Sotheby's Int'l

    209 Main St, Deep River, CT 06417
  • /37

    $1,650,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 4 Baths
    • 3,861 Sq Ft

    125 Ridgewood Dr, Milford, CT 06460

    Welcome to one of Morningside's most beautifully reimagined homes, where classic character and modern design come together in perfect harmony. This one-of-a-kind residence blends historic details-like a stunning original floor-to-ceiling stone fireplace-with the light-filled openness of contemporary living. Step inside to a sweeping first floor with soaring 10-foot ceilings and a seamless flow

    Jeremy Goun KNG Realty LLC

    125 Ridgewood Dr, Milford, CT 06460
  • /40

    $9,900,000

    • 21 Beds
    • 40 Baths
    • 51,830 Sq Ft

    50 Poplar Hill Dr, Farmington, CT 06032

    Once home to both Mike Tyson and 50 Cent, this extraordinary estate sits on more than 17 private acres in Farmington, Connecticut-a historic town just 10 miles west of Hartford and ideally positioned between Boston and New York City. Spanning an impressive 51,000 square feet, the residence embodies unmatched opulence, with over $3 million in recent renovations elevating it to a world-class

    Sherry Borgeson Berkshire Hathaway NE Prop.

    50 Poplar Hill Dr, Farmington, CT 06032
  • /40

    $1,595,000

    • 6 Beds
    • 5.5 Baths
    • 3,791 Sq Ft

    19 Pearl St, Groton, CT 06340

    Historic Downtown Mystic Well Maintained 4 Family Property. Income producing Well maintained Colonial with Private Parking. 100 percent Occupied with one year lease. This exceptional property features two covered porches and valuable off-street parking, just steps from Mystic's renowned shops, acclaimed restaurants, the iconic Bascule Bridge, sailing, kayaking, and year-round waterfront

    Judi Caracausa William Pitt Sotheby's Int'l

    19 Pearl St, Groton, CT 06340
  • /39

    $4,400,000

    • 4 Beds
    • 4.5 Baths
    • 4,927 Sq Ft

    565 Oenoke Ridge, New Canaan, CT 06840

    Experience Architectural History: The Celebrated Celanese House. This is your chance to own a true masterpiece. Designed in 1959 by visionary architect Edward Durell Stone, the Celanese House is one of New Canaan's most celebrated mid-century modern landmarks-an architectural treasure admired by design publications for decades. Stone's signature elements remain unmistakable: the striking lattice

    Inger Stringfellow William Pitt Sotheby's Int'l

    565 Oenoke Ridge, New Canaan, CT 06840
  • /37

    $1,149,000

    • 2 Beds
    • 3.5 Baths
    • 3,285 Sq Ft

    49 South St, Washington, CT 06793

    Western Sunset Views, a short distance from The Mayflower Inn and Washington Green. Discover the ultimate renovation project or the foundation for your future estate. Situated in an elite enclave of fine homes, this 1890s Barn-style residence-complete with its signature silo and 1970s additions-awaits a visionary touch. Whether you envision a meticulous restoration of a historic showpiece or a

    Kathryn Clair William Pitt Sotheby's Int'l

    49 South St, Washington, CT 06793
  • /56

    $8,000,000

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

    640 Round Hill Rd, Greenwich, CT 06831

    This is an opportunity to own a piece of Greenwich history. A fully restored antique farmhouse offering approximately 3,669 square feet of refined living space, set on extraordinary level acreage with sweeping meadow views and an irreplaceable country setting across from protected conservation land with direct access to the Greenwich Riding Trails. The residence blends historic authenticity with

    Monica Webster Douglas Elliman of Connecticut

    640 Round Hill Rd, Greenwich, CT 06831
  • /40

    $1,725,000

    • 2 Beds
    • 2 Baths
    • 2,163 Sq Ft

    66 High St Unit 34, Guilford, CT 06437

    Historic Elegance Meets Modern Luxury at 66 High Street | Leete Building. Welcome to an extraordinary residence where Guilford's heritage blends with contemporary sophistication. This impeccably appointed 2-bedroom+, 2-bath condominium with office/guest room is situated in the prestigious 66 High Street complex-a masterful transformation of an historic site into luxury living. Built in 2018, the

    Nikki Travaglino William Pitt Sotheby's Int'l

    66 High St Unit 34, Guilford, CT 06437
  • /2

    $299,900

    • Land
    • 34 Acres
    • $8,821 per Acre

    00 Ramsgate Ln, Barkhamsted, CT 06063

    30 +/- acres in ideal location in Barkhamsted bordering American Legion State Forest in the rear. Minutes from historic Riverton Center and world-renowned fly fishing. Many outdoor activities close by including hiking, biking, tubing, skiing, boating and many more. Land is ideal for almost any application, subdividing, recreation, horses, etc. Land will be subdivided upon contract and prior to

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    00 Ramsgate Ln, Barkhamsted, CT 06063
  • /39

    $945,000

    • 6 Beds
    • 4 Baths
    • 2,783 Sq Ft

    82 State St, Guilford, CT 06437

    Rare opportunity to own an in-town retreat just steps from the historic Guilford Green. This unique and well maintained two-family home offers a combination of flexibility, charm, and outdoor space that is nearly impossible to find this close to town. Whether you're seeking multi-generational living, rental income, or a lifestyle property with room to spread out, this home delivers exceptional

    Claudia Bartlett William Raveis Real Estate

    82 State St, Guilford, CT 06437
  • /39

    $699,900

    • 4 Beds
    • 3 Baths
    • 2,629 Sq Ft

    141 Maple Tree Hill Rd, Oxford, CT 06478

    Welcome to Boxwood Glenn - a rare, lovingly restored vintage treasure in the heart of Oxford. Classic New England farmhouse charm meets thoughtful modern updates in this exceptional home, nestled among stone walls, curated gardens, and serene natural surroundings. Step through the slatefloored sunroom, drenched in natural light, where views unfold over the hexagon garden, clipping garden, and a

    Joseph Cirillo Showcase Realty, Inc.

    141 Maple Tree Hill Rd, Oxford, CT 06478
  • /29

    $899,999

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    208 Wood Creek Rd, Bethlehem, CT 06751

    Historic Estate with Pond, Barns and 12.7 Acres of Natural Beauty - Step into a piece of New England history with this exceptional 12.7-acre estate, featuring a historic sea captain's home originally built in Mystic and relocated to Bethlehem in 1961. Rich in heritage and thoughtfully updated with newer roof and mechanics, the home offers three spacious bedrooms, including a primary suite with a

    Judy Stebbins Houlihan Lawrence WD

    208 Wood Creek Rd, Bethlehem, CT 06751
  • /24

    $479,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,680 Sq Ft

    490 Quinnipiac Ave, New Haven, CT 06513

    A rare opportunity on the Quinnipiac River. This historic 1810 Oyster House was thoughtfully restored in 1988 and further updated in 2000, blending period character with modern comfort. The property includes a 30foot fixed pier with an aluminum ramp to a floating dock, plus the potential for four pile moorings extending 200 feet into the navigable channel - a dream setup for boat owners. Enjoy

    Cheryl Szczarba Seabury Hill REALTORS

    490 Quinnipiac Ave, New Haven, CT 06513
  • /38

    $2,250,000

    • 4 Beds
    • 4 Baths
    • 3,239 Sq Ft

    31 Splitrock Rd, Norwalk, CT 06854

    Fairfield County's Gold Coast best-kept secret. Located in the historic, mid-century enclave of Village Creek, this refined waterfront residence captures sweeping views of a protected 100-acre estuary. Owners enjoy an unparalleled array of private community amenities-including a private sandy beach, tennis courts, deep-water marina, paddle-craft storage, dog park, playground, and athletic field.

    David White OwnerEntry.com

    31 Splitrock Rd, Norwalk, CT 06854
  • /16

    $775,000

    • Land
    • 26.68 Acres
    • $29,048 per Acre

    204 North St Unit Lot 3, Roxbury, CT 06783

    1st Time LISTED! LOT 3 at 204 North Street has ENGINEERING and DRIVEWAY APPROVED! THERE ARE LOTS AND THEN THERE ARE MAGICAL, SPECIAL, UNPARALLELED LOTS, STEEPED IN HISTORY WHERE YOU CAN ACTUALLY FEEL AND HEAR THE TERRAIN SINGING TO YOU. THE WOODS ROXBURY IS SUCH A PLACE AS EVIDENCED BY OUR RECENT SALES. This 25 acre lot features un-touched historic stone walls, a beautiful stream flowing, gently

    Jill Sloane Brown Harris Stevens

    204 North St Unit Lot 3, Roxbury, CT 06783
  • /39

    $1,350,000

    • 4 Beds
    • 3 Baths
    • 4,025 Sq Ft

    354 Route 7 N, Falls Village, CT 06031

    Seeking a serene, beautifully appointed home where you can live, work, and unwind surrounded by the natural beauty of Litchfield County? Look no further. Set on 6.29 acres of landscaped grounds, this meticulously restored 4,025 sq ft home-built in 1790-offers 4 spacious bedrooms and 3 full bathrooms. Thoughtfully renovated and expanded, the residence seamlessly blends modern comfort with historic

    Ann Stettner Neil Charles Real Estate

    354 Route 7 N, Falls Village, CT 06031
  • /38

    $630,000

    • 3 Beds
    • 2 Baths
    • 2,065 Sq Ft

    5 South Ln, Redding, CT 06896

    Perched at the crest of Redding Ridge on a lane shared by only five homes, this beautifully restored Cape occupies a truly commanding position. The property encompasses an entire side of South Lane, framed by original stone walls and mature trees that provide a sense of established privacy. In a region known for its rolling terrain, this home offers the rare luxury of an entirely usable,

    Thomas Skillman William Pitt Sotheby's Int'l

    5 South Ln, Redding, CT 06896

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