Homes for Sale in Connecticut - Historic

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  /35

  $1,845,000

  • 6 Beds
  • 5 Baths
  • 4,219 Sq Ft

  28 Sunny Ridge Rd, Washington, CT 06793

  Historic home with untapped potential in Washington. Set on 3.8 serene acres in the Sunny Ridge Historic District, this 1846 Colonial contains elements of the original house which was built in 1768 on the same location. With approximately 4,200 square feet of living space, the home's six bedrooms and three full, two half baths provide a flexible layout ready for a thoughtful renovation. The

  Sally Cornell Klemm Real Estate Inc

  28 Sunny Ridge Rd, Washington, CT 06793
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• 

  

  

  /40

  $1,097,700 Open Sat 1PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 5,134 Sq Ft

  371 N Main St, Suffield, CT 06078

  Attention location buyers: Your Extraordinary lifestyle awaits, with 5 bedrooms, including walk out studio apartment with separate entrance. From the sidewalk of historic main street, you are greeted with a professional office or living room off the foyer. The Wolf/Subzero chef's kitchen with custom white cabinetry, an 11' island with soapstone counters, a coffee bar with sink, a large panty with

  Kathy Murphy KW Legacy Partners

  371 N Main St, Suffield, CT 06078
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  /29

  $519,000

  • 2 Beds
  • 2 Baths
  • 1,476 Sq Ft

  4 Currycross Rd Unit 4, Madison, CT 06443

  Welcome to highly desirable Windermere East. Windermere is nestled in a private picture perfect setting along the Madison Shoreline. 4 Currycross Road is a charming free standing home with 2 spacious bedrooms, a pretty backyard, and one detached garage just steps to your front door. Home has been freshly painted and boast a lovely open floor plan with a wood burning fireplace, cathedral ceiling,

  Terry Morgan CT Realty Exchange, LLC

  4 Currycross Rd Unit 4, Madison, CT 06443
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  /40

  $850,000

  • 5 Beds
  • 3 Baths
  • 3,712 Sq Ft

  10 Yogananda St, Sandy Hook, CT 06482

  SUBMIT OFFERS-HIGHEST & BEST BY SUNDAY, MAY 10th, 5:00 pm Sip lemonade on your wrap-around front porch while enjoying the distant mountain views in this sought after neighborhood. This home has so many unique features like a 5th bedroom on the main level with a full bath, a private hidden office near the primary suite, and a he/she shed that will captivate you. Step inside to discover an open

  Patty McCarthy William Raveis Real Estate

  10 Yogananda St, Sandy Hook, CT 06482
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  /40

  $849,000

  • 5 Beds
  • 4.5 Baths
  • 5,957 Sq Ft

  133 Blake Rd, Hamden, CT 06517

  Renovated & expanded 1830's Colonial with 5 bedrooms & 4.5 baths located minutes from Yale & downtown New Haven on Blake Road in Hamden. With over 4000 sq ft this home blends historic charm with modern comforts. The inviting entryway leads to a formal living room with fireplace & picture window, as well as a bright formal dining room with cheerful wallpaper & chandelier. The spacious kitchen

  Jack Hill Seabury Hill REALTORS

  133 Blake Rd, Hamden, CT 06517
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  /37

  $875,000

  • 3 Beds
  • 3 Baths
  • 2,784 Sq Ft

  28 White Hollow Rd, Lakeville, CT 06039

  Live next to a Legend with this rare opportunity to own a stunning, antique home, walking distance to Lime Rock Park. This 1850 antique charmer sits steps from the iconic track on the same road - perfect for motorsport weekends, driver lifestyles, and tack side living. This 2,784 sq.ft. home on 1+ acre offers almost 400 ft. of riverfront serenity along the storied Salmon Kill with a private

  Lynn Attella Marrin Santore Realty LLC

  28 White Hollow Rd, Lakeville, CT 06039
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  /29

  $895,000

  • 4 Beds
  • 2.5 Baths
  • 2,624 Sq Ft

  403 Beach St, Litchfield, CT 06759

  Circa 1870 Restored Farmhouse in beautiful Litchfield. Discover your dream mini-farm on 9.1-acres of lush countryside. Whether you're longing for a hobby farm or a peaceful retreat, this versatile property lets you channel your inner farmer. This charming home showcases beautifully preserved vintage details including wide board wood floors, exposed beams, and three fireplaces, blending historic

  Maria Taylor Klemm Real Estate Inc

  403 Beach St, Litchfield, CT 06759
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  /12

  $895,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,283 Sq Ft

  253 Bacon Pond Rd, Woodbury, CT 06798

  Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are

  Christian Jensen William Pitt Sotheby's Int'l

  253 Bacon Pond Rd, Woodbury, CT 06798
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  /28

  $985,000

  • 3 Beds
  • 3 Baths
  • 3,225 Sq Ft

  28 Headquarters Rd, Litchfield, CT 06759

  Stimulating and easily managed home is perfect for weekending in an idyllic, small, historic village very close to big-time cultural, sports, and wildlife attractions. Living, dining, and kitchen areas are perfectly set up for entertaining. State-of-the-art appliances. Each bedroom has its own full bath and more. Multi-person ThermoSpa hot tub in enclosed (and air-conditioned) porch looks out on

  Cleve Fuessenich Klemm Real Estate Inc

  28 Headquarters Rd, Litchfield, CT 06759
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  /25

  $339,000

  • 1 Bed
  • 1 Bath
  • 1,115 Sq Ft

  817 Grand Ave Unit 202, New Haven, CT 06511

  Sophisticated New York-style loft offering 1,115 SQ FT of living space with 1 bedroom & 1 bath in a chic complex just steps from Wooster Square Park, Downtown NH & Yale. The open-concept floor plan has HW floors throughout and is perfect for entertaining. The generous flex living & dining area features an expansive window that overwhelms the room with natural light. The sleek, contemporary

  Jack Hill Seabury Hill REALTORS

  817 Grand Ave Unit 202, New Haven, CT 06511
• 

  

  /17

  $1,049,000

  • 8 Beds
  • 5 Baths
  • 2,902 Sq Ft

  16 Lynwood Place, New Haven, CT 06511

  Spacious and historic home for sale in the heart of Downtown New Haven. Renovated in 2018, this home is a legal rooming house and features 8 bedrooms and 5 full baths, currently leased by a sorority thru May 31, 2027. Rent is $10,350.00 per month. Main living area on the 1st floor and secondary living areas on garden floor and 3rd floor. Fully equipped kitchen with stainless steel appliances; gas

  Josh James Farnam Realty Group

  16 Lynwood Place, New Haven, CT 06511
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  /40

  $1,149,000

  • 3 Beds
  • 4 Baths
  • 3,199 Sq Ft

  252 Florida Hill Rd, Ridgefield, CT 06877

  This picturesque ca 1780 farmhouse retains all of its historic charm but has been updated & expanded for today including significant 3 car garage addition with magnificent great room above. Stunning 2.09 acres with scenic pond for kayaking & skating, rolling lawn, front porch, rear screened porch & deck, electrified cottage/shed, chicken coop, horse barn with one stall, fruit trees including

  Laura Ancona William Pitt Sotheby's Int'l

  252 Florida Hill Rd, Ridgefield, CT 06877
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  /40

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  779 Prospect Ave Unit 4, West Hartford, CT 06105

  Welcome to Barclay Court, a historic condo community offering a peaceful yet vibrant lifestyle in an unbeatable location. This move-in ready home perfectly blends style, comfort, and convenience, with thoughtful upgrades throughout. The updated kitchen is a true standout, featuring sleek stainless steel appliances, granite countertops, recessed lighting, and a stunning backsplash that adds a

  Rebecca Makas KW Legacy Partners

  779 Prospect Ave Unit 4, West Hartford, CT 06105
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  /25

  $1,095,000

  • 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
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  /40

  $995,000

  • 4 Beds
  • 3.5 Baths
  • 3,053 Sq Ft

  2222 Ridge Rd, North Haven, CT 06473

  The historic Joel E. Bassett House, originally a one room farmhouse built in 1802, elegantly remodeled in 2018 to meet the demands of modern living. The spacious home is 3,053 sq ft with 4 bedrooms 3.5 baths and is sited on a 1.76 acre corner lot. The expansive great room includes the living room, formal dining room & chef’s kitchen, and has gorgeous dark hardwood floors, coffered ceilings &

  Jack Hill Seabury Hill REALTORS

  2222 Ridge Rd, North Haven, CT 06473
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  /28

  $338,000

  • 1 Bed
  • 1 Bath
  • 743 Sq Ft

  85 Olive St Unit T, New Haven, CT 06511

  Adorable ranch-style condo set within a charming historic building in the heart of the Wooster Square neighborhood. A large entry foyer opens seamlessly into a spacious living room featuring a decorative fireplace and ample space for a dining table, creating an inviting setting for everyday living and entertaining. The kitchen blends character and function with retro GE appliances, butcher block

  Beth Cantor Coldwell Banker Realty

  85 Olive St Unit T, New Haven, CT 06511
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  /26

  $999,900

  • 3 Beds
  • 2.5 Baths
  • 2,042 Sq Ft

  27 Middle Quarter Rd, Woodbury, CT 06798

  Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room

  Tim Drakeley Drakeley Real Estate, Inc.

  27 Middle Quarter Rd, Woodbury, CT 06798
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  /40

  $979,900

  • 4 Beds
  • 3.5 Baths
  • 3,492 Sq Ft

  1209 Daniels Farm Rd, Trumbull, CT 06611

  Step into a piece of Trumbull's history with this enchanting, updated Craftsman Cape loc in the highly sought-after Daniels Farm section, close to top-rated schools, parks, shopping, restaurants, & major highways. Originally built by Col. William C. Weeks when Daniels Farm Rd was a rural farm district, this unique home, known as "Kobble Cot," blends historic charm w/ modern comfort & has long

  Jay Cannone William Raveis Real Estate

  1209 Daniels Farm Rd, Trumbull, CT 06611
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  /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
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  /38

  $340,000

  • 4 Beds
  • 1 Bath
  • 1,756 Sq Ft

  30 Chestnut Hill Rd, Killingworth, CT 06419

  ** A Unique Opportunity at 30 Chestnut Hill Road, Killingworth** Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of

  Nutan Pawar DreamHomes Realty LLC

  30 Chestnut Hill Rd, Killingworth, CT 06419
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  /12

  $785,000

  • 2 Beds
  • 2 Baths
  • 1,386 Sq Ft

  511 Route 81, Killingworth, CT 06419

  Have you ever wanted to own your own Connecticut farm that dates back to the 1850s? For the very first time in over 170 years, this beautiful property is being offered to the market. Passed down through generations, this remarkable 35+ acre property has been in the same family since the mid-1800s. A true piece of New England history waiting to be brought back to life. Picture yourself stepping

  Adam Bronko RE/MAX Right Choice

  511 Route 81, Killingworth, CT 06419
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  /37

  $3,495,000

  • 7 Beds
  • 8 Baths
  • 11,075 Sq Ft

  214 Good Hill Rd, Weston, CT 06883

  Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with

  John Schiaroli Coldwell Banker Realty

  214 Good Hill Rd, Weston, CT 06883
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  /15

  $25,500

  • 612 Sq Ft

  379 Whitfield St Unit AS2136, Guilford, CT 06437

  This 36-ft dock with unobstructed south-facing views of LI Sound, in the Guilford Yacht Club, is located on the protected West River in the charmingly historic town of Guilford CT. Not only does ownership of the dock provide you with a safe and easily accessible haven for your boat, but it also gives you and your family access to the spacious clubhouse, the heated pool with showers, and tennis

  Jake Wyman William Raveis Real Estate

  379 Whitfield St Unit AS2136, Guilford, CT 06437
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  /40

  $7,995,000

  • 8 Beds
  • 9 Baths
  • 8,934 Sq Ft

  236 & 250 Main St, Ridgefield, CT 06877

  Unprecedented opportunity to purchase two landmark, historic residences, situated side by side on Ridgefield's beloved Main St., which have been developed into an unparalleled lifestyle compound. This once in a lifetime sale includes the treasured Hawley House at 236 Main St. - Ridgefield's oldest home, on its original lot (5) which was built by the proprietors in 1713 for the Rev. Thomas Hawley,

  Laura Ancona William Pitt Sotheby's Int'l

  236 & 250 Main St, Ridgefield, CT 06877
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  /39

  $3,395,000

  • 7 Beds
  • 9 Baths
  • 7,002 Sq Ft

  10 Sunny Ridge Rd, Washington, CT 06793

  Major estate with the highest standards of construction located within the Sunny Ridge historic district. Situated on 10 private, park-like acres with an over-sized heated pool, fabulous stonewalls, giant dining terraces, pond and orchard. 7+ bedrooms, Billiard room, screening room, paneled library, sunroom, new country kitchen, 100-person party room boasts a restaurant size bar, sound system and

  Peter Klemm Klemm Real Estate Inc

  10 Sunny Ridge Rd, Washington, CT 06793
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  /24

  $399,000

  • 6 Beds
  • 3.5 Baths
  • 1,899 Sq Ft

  934 Storrs Rd, Storrs Mansfield, CT 06268

  Located in Mansfield's historic district, this property offers 6 bedrooms and 3.5 bathrooms with a flexible layout across two levels. The main floor includes four bedrooms, including a primary suite with a Jack-and-Jill bath. The eat-in kitchen features skylights and connects to the main living areas. A living room and formal dining room with built-in cabinetry provide additional space. The

  Marlinette Pacheco mygoodagent

  934 Storrs Rd, Storrs Mansfield, CT 06268
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  /26

  $319,900

  • 3 Beds
  • 1.5 Baths
  • 1,596 Sq Ft

  252 Hauser St, Waterbury, CT 06704

  Summer's coming! Enjoy this beautifully renovated ranch in a quiet yet convenient area within walking distance of historic Fulton Park. Enter a bright living room with hardwood floors and overhead fan, perfect for entertaining and relaxing. Need a big open concept kitchen? This is it - all stainless appliances, gorgeous tile backsplash, and contemporary yet classic cabinets - always stylish. The

  Mayer Behrend Mary Helen Levine Real Estate LLC

  252 Hauser St, Waterbury, CT 06704
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  /34

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,815 Sq Ft

  22 Westford Rd, Eastford, CT 06242

  A rare opportunity to own a piece of early New England history, this circa 1780 antique Cape is set in Eastford's quiet village setting, surrounded by open fields and timeless charm. Sited on nearly an acre with classic stone walls, this 3-bedroom, 2-bath home offers over 1800 square feet of character-filled living space. Original details include wide plank floors, exposed masonry, and multiple

  Robin Delaney Robin Delaney Real Estate

  22 Westford Rd, Eastford, CT 06242
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  /14

  $400,000

  • 11 Beds
  • 2.5 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
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  /40

  $2,750,000

  • 3 Beds
  • 3 Baths
  • 2,619 Sq Ft

  92 Water St, Stonington, CT 06378

  Direct Waterfront with Private 90' fixed IPE dock constructed 2012 by Gwenmor Marine. Appx. 3.5' of water at Low Tide, all located in the Heart of Historic Stonington Borough. Water, Louvered Halogen Foot Lights and 30amp power box on your private dock. Walls of Windows overlooking Stonington Harbor and your dock from this Stunning fully renovated 3 Bedrooms, 3 Full Baths waterfront home. Open

  Judi Caracausa William Pitt Sotheby's Int'l

  92 Water St, Stonington, CT 06378
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  /22

  $3,995,000

  • 6 Beds
  • 7.5 Baths
  • 5,628 Sq Ft

  11 Clapboard Hill Rd, Westport, CT 06880

  An antique jewel set on 3.5 extraordinary acres in the heart of Greens Farms, ready to be transformed into your forever home. Brimming with timeless charm and endless potential, this rare offering showcases beautiful period details, including arched doorways, custom built-ins, and charming deep-set windows that reflect the home's historic character. The gracious main house is complemented by a

  Meredith Cohen Serhant Connecticut, LLC

  11 Clapboard Hill Rd, Westport, CT 06880
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  /50

  $6,250,000

  • 5 Beds
  • 10 Baths
  • 7,632 Sq Ft

  21 Calhoun Dr, Greenwich, CT 06831

  Welcome to ''Park Hill'', a reimagined 1923 English Manor in a Prestigious Private Association. Thoughtfully refreshed for modern living while preserving the architectural character that makes it timeless. Set on 1.81 private, park-like acres, this 7,632 sq. ft. manor blends historic charm with contemporary luxury in a way few properties can. 1923 English Tudor Revival with 2025 updates. Rare

  Danielle Claroni Sotheby's International Realty

  21 Calhoun Dr, Greenwich, CT 06831
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  /14

  $350,000

  • Land
  • 1.3 Acres
  • $269,231 per Acre

  148 Kennedy Dr, Orange, CT 06477

  Rare opportunity to custom build a new home in an established neighborhood in the historic town of Orange. Beautiful, wide, quiet, residential road with a cul-de-sac bordering farmland at the end of the road. This mostly level, 1.30-acre lot is fully approved as a building lot with town approval of a complete site plan and septic plan for a 3-bedroom home with attached garage. Public water is

  Jorge Zea Blue Lighthouse Realty, Inc

  148 Kennedy Dr, Orange, CT 06477
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  /40

  $619,000

  • 4 Beds
  • 2.5 Baths
  • 2,126 Sq Ft

  64 Dohm Ave, Guilford, CT 06437

  This well-maintained ranch offers easy single-level living with a layout designed for comfort and convenience. Expanded and renovated to the studs in 2008, the home now features a new 1,500-gallon septic tank for a potential 5th bedroom and a radon-in-air mitigation system. Hardwood floors run throughout a bright, open floor plan with central air, while the spacious primary suite includes dual

  Linda Toscano Coldwell Banker Realty

  64 Dohm Ave, Guilford, CT 06437
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  /21

  $750,000 Open House 5/17

  • 2 Beds
  • 2 Baths
  • 1,179 Sq Ft

  1 Benson Ln, Essex, CT 06426

  Located in the Essex Village district on a corner lot at Saybrook Road and Benson Lane, this post-and-beam home was originally a cattle barn in the 1800s and was meticulously transformed into a residence by Sapia Builders in 1960. The home combines historic architectural details with modern updates, including wide plank floors, natural wood textures, and an open-concept main living area with a

  Katherine Bergeron Real Broker CT, LLC

  1 Benson Ln, Essex, CT 06426
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  /11

  $189,900

  • 2 Beds
  • 1 Bath
  • 955 Sq Ft

  839 Main St Unit 56, Torrington, CT 06790

  Welcome to Warrenton Mill - one of Torrington's most sought-after condo complexes - where historic charm seamlessly blends with modern living. This fully remodeled 2-bedroom, 1-bath condo with a second-story loft checks every box and more. The open-concept living space features soaring ceilings, exposed brick, and oversized windows that flood the home with natural light. The kitchen has been

  Derek Savoy Coldwell Banker Realty

  839 Main St Unit 56, Torrington, CT 06790
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  /40

  $699,900

  • 5 Beds
  • 3 Baths
  • 2,064 Sq Ft

  6 Jefferson St, New Haven, CT 06511

  Located in heart of beloved Historic Wooster Square; where timeless charm, vibrant city living, and smart investment potential beautifully align. This tastefully renovated two-family offers both lifestyle and opportunity. Set on a picturesque tree lined street just around the corner from WSQ Park, world-famous Wooster Street pizza, eateries & Farmer's Market, and just minutes to Yale University,

  Melanie Gunn Coldwell Banker Realty

  6 Jefferson St, New Haven, CT 06511
• 

  

  /15

  $212,000

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft

  92 Main St Unit 107, Deep River, CT 06417

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

  Anna Kilty Compass Connecticut, LLC

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

  

  /40

  $2,495,000

  • 5 Beds
  • 5.5 Baths
  • 5,543 Sq Ft

  137 Liberty St, Madison, CT 06443

  Rare opportunity to own in desirable Liberty Street area. This 1816 Federal-style residence & new detached historically designed barn, renovated and built by prominent historical design/build specialists Gulick & Co., creates a harmonious blend of formality and comfort. The main residence has 3,784 sq ft of living space, and the detached barn boasts 1,776 sq ft. The main residence is a

  Alison Gould Gould Group LLC

  137 Liberty St, Madison, CT 06443
• 

  

  /18

  $649,000

  • 2 Beds
  • 2.5 Baths
  • 1,868 Sq Ft

  91 Church St Unit 3, New Haven, CT 06510

  Urban oasis in the heart of Downtown New Haven! Welcome to The Lofts at 91 Church - where historic charm meets modern luxury. This stunning, one-of-a-kind loft condominium is part of a 2015 build-out within an early 1900's building, offering the perfect blend of classic architecture and contemporary design. This fabulous unit features soaring ceilings, expansive open-concept design, and refined

  Jill Nathanson-Zaengel Press/Cuozzo Realtors

  91 Church St Unit 3, New Haven, CT 06510

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