Homes for Sale in Connecticut - Historic

/39
$874,900
- 4 Beds
- 2.5 Baths
- 3,700 Sq Ft
339 Main St S, Woodbury, CT 06798

One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm

Marian Van Egas

Berkshire Hathaway NE Prop.

(475) 405-2250

339 Main St S, Woodbury, CT 06798
/20
$1,200,000
- 1 Bed
- 4 Baths
- 1,824 Sq Ft
24-26 Lyme St, Old Lyme, CT 06371

*TENANT FREE* Two well-maintained historic buildings in the heart of the Old Lyme Historic District! 24 & 26 Lyme Street are being sold together, offering a unique chance to invest in a high-visibility location within this charming New England village. * 24 Lyme Street (built in 1800) features 1,824 sq. ft. of retail and office space, ideal for business use or potential redevelopment. * 26 Lyme

Logan Hayes

NestSeekers International

(860) 743-0604

24-26 Lyme St, Old Lyme, CT 06371
/34
$850,000

Open Sun 12PM - 2PM
- 3 Beds
- 2 Baths
- 2,489 Sq Ft
47 South St, Roxbury, CT 06783

Step back in time and own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic

Michelle Alvord

Berkshire Hathaway NE Prop.

(860) 934-0323

47 South St, Roxbury, CT 06783
/38
$199,000

Coming Soon
- 3 Beds
- 1 Bath
- 1,685 Sq Ft
41 Center St, Hartford, CT 06120

Timeless character meets modern updates in this beautifully renovated brick home. Filled with natural light, the spacious interior features gleaming hardwood floors, oversized rooms, and stunning bay windows that add charm and architectural appeal. The stylish kitchen offers quartz countertops, custom cabinetry, stainless steel appliances, and abundant workspace for everyday living and

Ilka Torres

Torbello Real Estate Advisors

(860) 351-1672

41 Center St, Hartford, CT 06120
/28
$1,148,000

Open Sat 1PM - 3PM $101K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,803 Sq Ft
332 Belden Hill Rd, Wilton, CT 06897

Welcome to the historic James Benedict House, one of Wilton's most notable and beautifully preserved 18th-century residences. This thoughtfully updated antique Colonial seamlessly blends timeless craftsmanship with modern convenience, offering 2,803 square feet across three full levels-including a true third floor with tall ceilings (not an attic)-plus a walk-out lower level ready to be finished.

Cosmo Iadanza

Century 21 AllPoints Realty

(475) 260-5520

332 Belden Hill Rd, Wilton, CT 06897
/40
$374,900
- 3 Beds
- 2 Baths
- 1,485 Sq Ft
128 Broad St, Plainville, CT 06062

Step back in time and experience the charm of the historic Norman Smith Home, a classic Greek Revival residence built in 1854. Nestled among a collection of Victorian-era homes on Broad Street, this property offers a unique blend of historical character and everyday functionality. The home features three bedrooms, two full bathrooms, and a versatile floor plan that includes an eat-in kitchen,

Jennifer Hunt

Berkshire Hathaway NE Prop.

(860) 792-5106

128 Broad St, Plainville, CT 06062
/40
$2,200,000
- 6 Beds
- 4 Baths
- 3,131 Sq Ft
26 Pearl St, Groton, CT 06340

Nestled in the heart of Mystic's Historic District, The Captain William Morgan House presents a rare opportunity to own one of the village's most distinguished income-producing properties. Set on nearly a half-acre just moments from downtown Mystic, the Mystic River, restaurants, shops, galleries, and marinas, this circa-1852 Greek Revival sea captain's residence blends historic character with

Tim Bray

Seaport Real Estate Services

(959) 271-2545

26 Pearl St, Groton, CT 06340
/44
$3,795,000
- 4 Beds
- 5 Baths
- 3,421 Sq Ft
88 Water St, Stonington, CT 06378

At the edge of Stonington Harbor, where sailboats move slowly through the water and the village wakes each morning to the rhythm of the tide, 88 Water Street offers a rare opportunity to live directly within one of New England's most beloved coastal communities. This historic home dates to 1840, yet today it feels distinctly current following an extensive renovation completed in 2022. The result

Danielle Malloy

Serhant Connecticut LLC

(860) 483-3587

88 Water St, Stonington, CT 06378
/38
$1,695,000
- 5 Beds
- 3.5 Baths
- 3,912 Sq Ft
30 Meeting House Ln, Madison, CT 06443

Historic gem on the Madison Village Green. Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the

Cathy Lynch

Coldwell Banker Realty

(475) 244-1665

30 Meeting House Ln, Madison, CT 06443
/40
$365,000
- 3 Beds
- 2 Baths
- 2,438 Sq Ft
60 Chaplin St, Chaplin, CT 06235

Welcome to place where time truly is the most beautiful thing. There is a particular kind of feeling when you walk through a historic door like this. Maybe it's the hardwood plank floors that have held two centuries of footsteps. Maybe it's the way the morning light hits the windows on every home on Chaplin Street, a village so notable it's listed on the National Register of Historic Places.

Stephen Daly

KW Legacy Partners

(860) 813-2932

60 Chaplin St, Chaplin, CT 06235
/39
$599,000

$26K PRICE DROP
- 4 Beds
- 3 Baths
- 1,941 Sq Ft
256 Nichols Ave, Shelton, CT 06484

Experience the charm of this beautiful antique Colonial home located in Huntington at 256 Nichols Avenue, on a picturesque, park-like grounds, complete with a small barn, gardening shed, and elegant stonework. This residence combines classic historic features with modern updates, showcasing solid mechanics and evident pride of ownership. Original wide plank floors grace the living room, dining

Cheryl Arbelo

Real Estate Two

(475) 255-7331

256 Nichols Ave, Shelton, CT 06484
/39
$469,900
- 3 Beds
- 2.5 Baths
- 2,336 Sq Ft
380 Main St, Meriden, CT 06451

Step into timeless charm with this beautifully renovated 1803 Colonial at 380 Main St in Meriden. This 3-bedroom, 2.5-bath home blends historic character with modern updates, featuring new ductless heating and cooling, windows, and deck for peace of mind. Inside, you'll find a warm and inviting eat-in kitchen with a cozy gas fireplace-perfect for gatherings year-round. The home offers two

Samantha Conde

RE/MAX One

(475) 275-9118

380 Main St, Meriden, CT 06451
/40
$798,000

$77K PRICE DROP
- 3 Beds
- 3 Baths
- 2,080 Sq Ft
98 Carmel Hill Rd N, Bethlehem, CT 06751

A turnkey Litchfield County retreat just 90 min from NYC, offering historic character, designer finishes, and effortless weekend living moments from Washington, Litchfield, and Woodbury.Originally an 1800s caretaker's cottage, this beautifully renovated antique has been thoughtfully expanded & extensively updated between 2023 and 2026, blending timeless New England charm w/modern luxury. Set on

Rebecca Doh

W. Raveis Lifestyles Realty

(475) 269-6838

98 Carmel Hill Rd N, Bethlehem, CT 06751
/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

Anthony Velez

VC Property Group, LLC

(860) 579-1057

87 Main St, Deep River, CT 06417
/40
$995,000

$400K PRICE DROP
- 5 Beds
- 4 Baths
- 4,636 Sq Ft
45 Clark Rd, Old Lyme, CT 06371

After a year of rehabilitation, this beautiful & spacious colonial home has been thoughtfully & tastefully completely remodeled & enhanced! Located in the heart of Lyme just a short distance from the historic ferry, Gillette's Castle & Fox Hopyard Country Club, this home boasts a very modern feel with an open & airy floor plan. All aspects have been brilliantly brought to life inside & out! The

Kevin Geysen

William Pitt Sotheby's Int'l

(860) 809-1876

45 Clark Rd, Old Lyme, CT 06371
/40
$615,000

Open Sun 1PM - 3PM
- 5 Beds
- 3 Baths
- 2,528 Sq Ft
700 Watertown Rd, Middlebury, CT 06762

This beautifully maintained Vintage Colonial blends historic charm with thoughtful updates throughout. Set on 1.25 meticulously landscaped acres, this 5-bedroom, 3-bath home offers warmth, space, and versatility. Built-in equity is an added bonus, with a recent appraisal valuing the home at $715,000. The stunning grounds feature mature plantings, classic New England stone walls, and inviting

Erin Giguiere

Regall Realty, LLC

(475) 244-1504

700 Watertown Rd, Middlebury, CT 06762
/40
$2,200,000
- 4 Beds
- 3.5 Baths
- 3,957 Sq Ft
47 E Kings Hwy, Chester, CT 06412

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

Al Chiarito

Chiarito Real Estate LLC

(860) 846-4174

47 E Kings Hwy, Chester, CT 06412
/40
$1,799,900

$75K PRICE DROP
- 5 Beds
- 3 Baths
- 3,032 Sq Ft
82 Lee Dr, Fairfield, CT 06824

Ideally located in the highly sought-after Sasco Hill neighborhood, this exceptional coastal home offers the rare advantage of beach-area living outside the flood zone-no flood insurance required. Perfectly positioned between town and shoreline, the property features a stunning second-floor addition completed in 2025 with over $200,000 invested, including a rooftop deck with beautiful Long Island

Jacek Mikolajczyk

Berkshire Hathaway NE Prop.

(475) 269-6318

82 Lee Dr, Fairfield, CT 06824
/40
$1,999,000
- 4 Beds
- 5 Baths
- 4,016 Sq Ft
445 Orange St, New Haven, CT 06511

A rare opportunity to own one of New Haven's most distinguished mid-19th century landmarks. Believed to have been designed by renowned architect Henry Austin for prominent New Haven physician Dr. William DeForest in 1858, this stately Greek Revival brick residence occupies a prominent site in the southern section of the coveted East Rock neighborhood. Meticulously restored by the current owner,

Wojtek Borowski

Pearce Real Estate

(475) 335-8825

445 Orange St, New Haven, CT 06511
/40
$1,199,000

Open Sat 12PM - 2PM
- 3 Beds
- 3 Baths
- 3,113 Sq Ft
60 Lyme St, Old Lyme, CT 06371

A Rare Mixed Use Offering with River Access in the Heart of Old Lyme Village. Set in the center of Old Lyme Village, this storied 1897 landmark, originally the James Bugbee Store offers a compelling opportunity to reimagine a historic property as a refined live/work compound or gallery driven residence. The flexible zoning allows for both residential and commercial use, making it particularly

Tammy Tinnerello

William Pitt Sotheby's Int'l

(860) 752-1176

60 Lyme St, Old Lyme, CT 06371
/24
$595,000
- Land
- 100 Acres
- $5,950 per Acre
259 Quarry Rd, Woodstock, CT 06281

Discover the possibilities on this exceptional 100-acre parcel on Quarry Road in scenic Woodstock, Connecticut. Boasting approximately 1,900 feet of road frontage, this expansive property offers a rare combination of privacy, natural beauty, and development potential. The current owner has already cleared three beautiful potential building sites, each positioned to take advantage of the

Carol Ryniewicz

CR Premier Properties

(860) 288-3922

259 Quarry Rd, Woodstock, CT 06281
/38
$1,695,000

Open Sat 1PM - 3PM Coming Soon
- 4 Beds
- 5 Baths
- 3,615 Sq Ft
137 Sturges Ridge Rd, Wilton, CT 06897

The Levi Coley House, circa 1848, is widely regarded as Wilton's most significant Greek Revival residence. A grand portico with four Doric columns sets a striking tone, while inside, historic character blends seamlessly with modern updates. Original wide-plank floors, soaring ceilings, oversized windows, and five of six original fireplaces (four functional, 2 gas and 2 wood burning) highlight the

Megan Sullivan

Douglas Elliman of Connecticut

(475) 281-3801

137 Sturges Ridge Rd, Wilton, CT 06897
/14
$215,000
- 2 Beds
- 1 Bath
- 1,202 Sq Ft
46 S Cherry St Unit 327, Wallingford, CT 06492

Welcome to Judd Square, where historic charm meets easy one-level living. This spacious ranch-style condominium offers an open and airy feel with oversized rooms, soaring ceilings, and abundant natural light streaming through the large windows that have made Judd Square one of Wallingford's most distinctive communities. The generous living and dining areas provide the perfect space for

Heike Severine

Coldwell Banker Realty

(833) 315-5239

46 S Cherry St Unit 327, Wallingford, CT 06492
/34
$749,000

Open Sat 11AM - 1PM Coming Soon
- 3 Beds
- 2 Baths
- 1,913 Sq Ft
20 Forest Hills Dr, Madison, CT 06443

Picture-perfect English Cape built in 1935, brimming with timeless charm and classic architectural details. A welcoming center-hall foyer features graceful archways leading to the formal living room, where custom built-ins frame the fireplace, and the elegant dining room with its original corner cabinet. It offers a sun-filled kitchen and a family room that opens to a rear deck overlooking a

Dana Weinstein

Coldwell Banker Realty

(475) 471-1357

20 Forest Hills Dr, Madison, CT 06443
/2
$4,200,000
- 6 Beds
- 7.5 Baths
- 7,450 Sq Ft
760 Valley Rd, New Canaan, CT 06840

A Historic Masterpiece, Reimagined for Modern Living Originally crafted in 1931 by renowned architect Frazier Forman Peters, this iconic stone residence has been completely reinvented-expanded, redesigned, and redefined for today's luxury lifestyle. The newly completed home now offers over 9,000 square feet of exquisite living space with 6 bedrooms, 7.5 baths, and every modern comfort imaginable,

Richard Breglia

Coldwell Banker Realty

(203) 721-7670

760 Valley Rd, New Canaan, CT 06840
/37
$774,900

$25K PRICE DROP
- 4 Beds
- 2.5 Baths
- 2,276 Sq Ft
1246 Pequot Trail, Stonington, CT 06378

Located in Stonington, 1246 Pequot Trail is a timeless treasure that perfectly blends historic charm with modern potential. Built in 1840, this well-loved antique home boasts four bedrooms, two and a half bathrooms, and an array of original details that tell a story of craftsmanship and heritage. From the moment you step inside, you'll be captivated by the character-rich woodwork, antique

Fran Wiehn

Compass Connecticut, LLC

(860) 321-5887

1246 Pequot Trail, Stonington, CT 06378
/33
$989,000
- 4 Beds
- 2.5 Baths
- 2,468 Sq Ft
21 Elm St, Stonington, CT 06378

Situated in the heart of Stonington Borough, 21 Elm Street is a striking historical colonial that pairs late-19th-century character with modern updates, leaving endless possibilities for a new owner to make the house their own. Spanning nearly 2,500 square feet of living space, the residence features four bedrooms, two full baths and one half bath, plenty of room to entertain and relax with two

Jonah Tomsick

Flagship Real Estate Advisors

(860) 364-8625

21 Elm St, Stonington, CT 06378
/14
$650,000
- Land
- 153 Acres
- $4,248 per Acre
0 Kozey Rd, Eastford, CT 06242

Extraordinary 153-acre parcel nestled in the heart of Connecticut's scenic Last Green Valley, offering exceptional privacy and natural beauty. This remarkable property borders Natchaug State Forest, Yale Meyers Forest, and the historic Old Connecticut Path, placing thousands of acres of protected woodland at your doorstep. Rolling terrain, hardwoods, and abundant wildlife create a stunning

Elizabeth Scranton

Kazantzis Real Estate, LLC

(860) 454-6435

0 Kozey Rd, Eastford, CT 06242
/38
$645,500
- 3 Beds
- 2.5 Baths
- 2,478 Sq Ft
429 New Sweden Rd, Woodstock, CT 06281

Step back in time and discover the charm of this beautifully preserved 2,400 sq. ft. farmhouse, originally built in 1805. Rich in character and timeless appeal, this property offers the perfect blend of country living and modern convenience. Whether you dream of cultivating extensive gardens, raising animals, creating a self-sustaining homestead, or simply enjoying wide-open spaces, this property

Elizabeth Scranton

Kazantzis Real Estate, LLC

(860) 351-6156

429 New Sweden Rd, Woodstock, CT 06281
/40
$1,800,000

Open Sat 11AM - 1PM
- 4 Beds
- 2.5 Baths
- 2,944 Sq Ft
36 Pearl St, Groton, CT 06340

The Lanman Lamb House, circa 1840 - a graceful Colonial in Mystic's Historic District, still bearing its original builder's plaque. On a fenced 0.25-acre corner lot steps from the river and downtown: 4 bedrooms, 2.5 baths, hardwood floors, built-ins, a bay-window living room, wood-stove parlor, and remodeled island kitchen. Sunroom overlooking the 30x15 pool, screened porch, detached 2-car

Tim Bray

Seaport Real Estate Services

(860) 672-1418

36 Pearl St, Groton, CT 06340
/31
$1,200,000

Open Sat 12PM - 2PM
- 6 Beds
- 3 Baths
- 3,322 Sq Ft
116 Deer Hill Ave, Danbury, CT 06810

Danbury's historic and prestigious Deer Hill Avenue sets the perfect stage for this 3322 Square Foot 1900 Victorian Dream Home. This stunning classic legal two family combines 21st Century updates and conveniences with old world craftmanship and charm. The potential for income is amazing for an investor. If your goal is to enjoy the ultimate in luxury and comfort as 0wner-occupied this is the

Victor Vescera

Keller Williams Realty

(475) 270-1856

116 Deer Hill Ave, Danbury, CT 06810
/36
$3,400,000
- 6 Beds
- 9 Baths
- 6,995 Sq Ft
351 Erskine Rd, Stamford, CT 06903

Rich in history and beautifully reimagined for modern living, this extraordinary North Stamford property began as a c.1780 Saltbox Colonial and has evolved into a gracious country estate. Set on 2.7 bucolic acres, the property artfully blends historic character with contemporary comfort. Expanded in the 1940s and meticulously renovated in 2020, the home honors its architectural heritage while

Suzette Kraus

Compass Connecticut, LLC

(475) 270-5765

351 Erskine Rd, Stamford, CT 06903
/37
$1,350,000

Open Sun 1PM - 4PM
- 3 Beds
- 3.5 Baths
- 3,570 Sq Ft
1335 Pequot Trail, Stonington, CT 06378

Tucked behind mature trees and framed by classic stone walls, this remarkable Stonington property feels more like a private country estate than a traditional residence. Set on nearly three beautifully maintained acres, the grounds unfold with expansive lawns, established gardens, and peaceful outdoor spaces that create an immediate sense of calm and privacy. The setting tells a story of timeless

Tammy Tinnerello

William Pitt Sotheby's Int'l

(860) 718-4906

1335 Pequot Trail, Stonington, CT 06378
/26
$475,000

Coming Soon
- 3 Beds
- 1.5 Baths
- 2,017 Sq Ft
130 Marvelwood Dr, New Haven, CT 06515

Charming Tudor Revival brick home blending timeless character with thoughtful updates in the heart of Westville. Offering 2,017 square feet of inviting living space, this home features 3 bedrooms, 1.5 baths, and an attached two-car garage on a beautifully landscaped 0.32-acre lot set well above the street for added privacy. Rich hardwood floors, graceful arched doorways, and a wood-burning

Wojtek Borowski

Pearce Real Estate

(475) 270-4968

130 Marvelwood Dr, New Haven, CT 06515
/34
$4,625,000
- 3 Beds
- 2.5 Baths
- 3,000 Sq Ft
305 Pequot Trail, Pawcatuck, CT 06379

Welcome to Little Pond Farm in Stonington, CT. This private estate of 96 acres on the Connecticut shoreline is midway between Boston and New York and minutes from ocean beaches, sailing, and the historic village of Mystic. It offers the space and privacy of true country living within easy reach of the coast. The custom main residence pairs scale with warmth: a great room anchored by reclaimed

Mark Bevington

Coldwell Banker Realty

(860) 217-8040

305 Pequot Trail, Pawcatuck, CT 06379
/35
$1,299,000
- 4 Beds
- 3.5 Baths
- 2,958 Sq Ft
181 Georgetown Rd, Weston, CT 06883

Welcome to 181 Georgetown Road, a timeless Weston antique dating back to 1820 that beautifully blends historic character with modern comfort. Rich in period charm and thoughtfully updated for today's lifestyle, this inviting 4/5-bedroom, 3.5-bath residence offers nearly 3,000 square feet of living space set amidst picturesque grounds designed for year-round enjoyment. Inside, original

Brett Lieberman

The Riverside Realty Group

(475) 252-5365

181 Georgetown Rd, Weston, CT 06883
/2
$749,000

Coming Soon
- 5 Beds
- 5 Baths
- 3,622 Sq Ft
59 W Hill Dr, West Hartford, CT 06119

Your chance to get into the amazing historic neighborhood! Once the site of a Vanderbilt mansion, the West Hill neighborhood was transformed in 1918, and this home was built in 1923. Offering all the charm and character of the period, both inside and out. High ceilings, woodwork, built-ins, wood floors, and a classic Tudor exterior. But also find a high efficiency heating system, central air and

Carl Lantz

Coldwell Banker Realty

(860) 901-8490

59 W Hill Dr, West Hartford, CT 06119
/26
$535,000

$15K PRICE DROP
- 5 Beds
- 3.5 Baths
- 4,146 Sq Ft
142 Broad St, Norwich, CT 06360

Rare opportunity to own a beautifully renovated historic multi-family in Norwich with strong income potential and modern tenant-pleasing features! Currently a fully occupied 2-family with excellent rental history, this gem has zoning approval already in place to convert to a 3-family, unlocking even greater cash flow. There are existing stamped drawings with the layout ready to build. Apartments

Tracy O'Donnell

Berkshire Hathaway NE Prop.

(860) 926-0135

142 Broad St, Norwich, CT 06360
/4
$1,790,000

New Construction
- 4 Beds
- 3.5 Baths
- 3,200 Sq Ft
31 Stony Lane Lot 1 Rd, Madison, CT 06443

Indulge in refined living at our Barberry Farm Open Space subdivision with Waterside Building and Development. Your bespoke home, spanning 3,000 to 4,000+ sq ft, promises not just spacious elegance but high-end finishes and meticulous craftsmanship. Situated within walking distance to Madison beaches and a golf course, this enclave blends luxury with convenience. Revel in the exquisite details of

Lindsay Greenberg

William Raveis Real Estate

(475) 251-8746

31 Stony Lane Lot 1 Rd, Madison, CT 06443
/24
$288,990

$21K PRICE DROP
- 2 Beds
- 2.5 Baths
- 1,916 Sq Ft
54 Clubhouse Dr Unit 54, Woodbury, CT 06798

Welcome to this light-filled and beautifully maintained townhome in the highly sought-after Woodlake community in Woodbury. Spanning three levels, this inviting home offers a rare blend of space, comfort, and seasonal views of Wood Lake. The main level features a spacious living and dining area anchored by a striking floor-to-ceiling fireplace, enhanced with a wood-burning insert (2021). Sliding

Henrik K Kjaer Keller Williams Realty

54 Clubhouse Dr Unit 54, Woodbury, CT 06798

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