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5-Bedroom Homes for Sale in Litchfield County CT

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  • /40

    $799,000

    • 5 Beds
    • 4 Baths
    • 4,696 Sq Ft

    89 East St, Morris, CT 06763

    Welcome to your dream retreat! Set on over 4 private acres of scenic countryside, this spacious contemporary home offers the perfect blend of style, comfort, and room to grow. With 5 generously sized bedrooms and 4 full bathrooms, there's space for everyone-whether you're hosting guests, working from home, or building your family's future. The home's distinctive floor plan positions the bedrooms

    Sonia Peck William Pitt Sotheby's Int'l

    89 East St, Morris, CT 06763
  • /14

    $595,000

    • 8 Beds
    • 4 Baths
    • 3,500 Sq Ft

    230 Winsted Rd, Torrington, CT 06790

    Beautiful, cash flowing 4 Family in one of Connecticut's most highly desired multifamily markets. Property features 2 buildings on one lot, for a total of 4 units, each with an attached 2 car garage. Units have undergone recent renovations. Great opportunity to start or add a stabilized investment asset to the portfolio. The property consists of one 3 Bedroom, two 2 Bedroom and one 1 Bedroom

    Connor Wenchell VC Property Group, LLC

    230 Winsted Rd, Torrington, CT 06790
  • /14

    $349,900

    • 5 Beds
    • 4 Baths
    • 2,770 Sq Ft

    683 Torringford St, Torrington, CT 06790

    Estate Sale: 2,770 Sq. Ft. Colonial w/In-Law Apartment on 2.29+/- Acres with Subdivision Potential! Being Sold in its "As Is and Where Is" Condition. Ideal for Contractor, Custom Builder or Antique Home Renovation Specialist.The Torringford Area of the City is where you'll discover this "Hidden Gem"! A Circa 1825 Early Colonial possessing Original Wide Board Floors, Windows, and Generous Size

    Marshall Cohen Cohen Agency

    683 Torringford St, Torrington, CT 06790
  • /2

    $369,000

    • 5 Beds
    • 3 Baths
    • 2,371 Sq Ft

    48 Brookside Ave, Torrington, CT 06790

    A maintained three-unit multifamily property offering strong income potential in the heart of Torrington. Each unit provides spacious living areas, functional layouts, and reliable rental history, making this an ideal choice for investors seeking consistent cash flow. 48 Brookside Ave delivers location, functionality, and long-term growth potential. Can be bought in combination with 41 Brookside

    Connor Wenchell VC Property Group, LLC

    48 Brookside Ave, Torrington, CT 06790
  • /36

    $1,195,000

    • 5 Beds
    • 5 Baths
    • 2,804 Sq Ft

    286 South St, Roxbury, CT 06783

    Discover this charming 4-bedroom Colonial with 1 additional bedroom is attached in-law apt on the southern side of Roxbury, offering an idyllic escape with seamless access to NYC. This privately situated home rests in a serene meadow, gracefully bordered by Pierce Brook. The main residence features a comfortable layout with a living room and fireplace that flows into the dining area and kitchen.

    Kathryn Clair William Pitt Sotheby's Int'l

    286 South St, Roxbury, CT 06783
  • /40

    $485,000

    • 5 Beds
    • 2 Baths
    • 1,971 Sq Ft

    1153 Guernseytown Rd, Watertown, CT 06795

    Welcome to 1153 Guernseytown Road, Watertown CT - a charming 1835 Cape-style, timber frame farmhouse once known as the Dickinson Farm. A graceful wraparound driveway leads you to this historic gem, perched on a knoll with 2.25 acres of panoramic countryside views, a backyard patio perfect for gatherings, and a classic 5000 sq. ft. Two story barn, weathered by time yet rich with potential. At the

    Jordan Ostrofsky KW Legacy Partners

    1153 Guernseytown Rd, Watertown, CT 06795
  • /28

    $3,495,000

    • 5 Beds
    • 3 Baths
    • 2,008 Sq Ft

    25 Arrow Point Rd, Warren, CT 06777

    Location. Location. Location. Rarely available Direct Lakefront on Lake Waramaug. 5-bedroom Contemporary with long lake views. Open floor plan with vaulted living room with fireplace, Dining room and Eat-in Kitchen. Screened porch. 1st floor bedroom & full bath. Family Room with fireplace. Walkout lower level. Level lawn to water's edge. 100' of direct waterfrontage with Long Lake Views. Floating

    Peter Klemm Klemm Real Estate Inc

    25 Arrow Point Rd, Warren, CT 06777
  • /40

    $6,750,000

    • 5 Beds
    • 7 Baths
    • 5,500 Sq Ft

    158 Popple Swamp Rd, Washington Depot, CT 06794

    Escape to an award-winning estate nestled in the heart of Washington, CT-just 90 miles from New York City. Situated on over 80 acres of pristine, level land, this exceptional modern farmhouse offers a rare combination of architectural excellence, luxurious amenities, and unparalleled natural beauty. Featured in New England Home and honored with CTC&G's prestigious Innovation in Design award, this

    Kathryn Clair William Pitt Sotheby's Int'l

    158 Popple Swamp Rd, Washington Depot, CT 06794
  • /15

    $1,200,000

    • 11 Beds
    • 7.5 Baths
    • 6,365 Sq Ft

    45 Sunny Ridge Rd, Washington, CT 06793

    Unique Opportunity to restore a grand c. 1910 Colonial or build new on 10+/- open acres surrounded by large estates in top Washington, CT location. Currently, the main floor comprises 2 apartments with an attached garage, the second floor has 5 en suite bedrooms plus a sitting room with a wet-bar and the third floor has 3 bedrooms, 1 full bath and a kitchen. With many original period features

    Peter Klemm Klemm Real Estate Inc

    45 Sunny Ridge Rd, Washington, CT 06793
  • /32

    $595,000

    • 5 Beds
    • 3 Baths
    • 2,596 Sq Ft

    310 S Kent Rd, South Kent, CT 06785

    This captivating antique property, located in South Kent, is a treasure trove of history, set against the backdrop of Kent's rolling hills. The residence, rich in character, features original details that tell a story of craftsmanship and care. Some of the details that offer a unique nod to the past, include hand-hewn beams, repurposed from a local barn and heart pine hardwood floors that have

    Phil Fox William Pitt Sotheby's Int'l

    310 S Kent Rd, South Kent, CT 06785
  • /27

    $549,999

    • 6 Beds
    • 3.5 Baths
    • 3,534 Sq Ft

    187 Hillside Ave, Torrington, CT 06790

    Beautiful single family custom/remodeled colonial home with 3534 SQ. the house is nestle in a peaceful neighborhood, most of the new addition was built in 2006, including foundation for this home, the house boasts 6 generously - sized bedrooms, 3 1/2 bathrooms, the primary suite bedroom will exceed every expectation, custom jacuzzi and shower separately, large walk-in closets, a large kitchen

    Milena Quinto MQ Realty

    187 Hillside Ave, Torrington, CT 06790
  • /20

    $3,250,000

    • 5 Beds
    • 4.5 Baths
    • 4,836 Sq Ft

    Unlisted Address

    Tower Hill house sits on 7 acres with 800 feet of frontage along the western shore of Doolittle Lake in Norfolk, CT. Designed by a local architect and built by local craftspeople, the house is privately sited down a long driveway and sits on a little bluff so there are lovely views over the lake. The Doolittle community takes great care to protect the health of the lake and its surrounding

    Betsy Little Betsy Little Real Estate LLC

    Unlisted Address
  • /37

    $3,250,000

    • 5 Beds
    • 5.5 Baths
    • 5,455 Sq Ft

    Unlisted Address

    Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious media room. The main floor primary suite includes a fireplace, office space, and large walk in closet. There is an addl

    Stacey Matthews W. Raveis Lifestyles Realty

    Unlisted Address
  • /40

    $3,999,000

    • 8 Beds
    • 9 Baths
    • 8,072 Sq Ft

    1 Great Elm Dr, Sharon, CT 06069

    Enjoy estate living with the convenience and ease of a shared community. Amenities include a 70ft heated pool, tennis and separate paddle/pickle courts. Owned by a noteworthy family for over 100 years, this is a rare opportunity to reside in one of Sharon's most treasured properties. The home encompasses the majority of the original mansion and was thoroughly renovated in 2013 with tasteful

    Pels Matthews W. Raveis Lifestyles Realty

    1 Great Elm Dr, Sharon, CT 06069
  • /39

    $729,000

    • 5 Beds
    • 3.5 Baths
    • 5,676 Sq Ft

    6 High Meadow Rd, New Milford, CT 06776

    Large unique and custom 5 bedroom Contemporary with Forever Views and open layout!! Lots of glass and views from most rooms. Huge vaulted family room with awesome entire wall floor to ceiling stone fireplace. Granite eat in kitchen with stainless appliances. Main level primary bedroom with full bath, double sink, whirlpool tub and walk in closet. Living room/den with custom built ins. Hardwood

    Joe Chemero Coldwell Banker Realty

    6 High Meadow Rd, New Milford, CT 06776
  • /30

    $5,495,000

    • 5 Beds
    • 5 Baths
    • 3,200 Sq Ft

    18 Arrow Point Rd, Warren, CT 06777

    Rare Direct Waterfront Lake Waramaug 5 bedroom / 3 full & 2 half bathroom home with stunning western views on beautifully maintained double lot. Eat-in Kitchen. Vaulted Living Room with fieldstone fireplace & sliders. Vaulted Family Room with built-in bookshelves & gas fireplace. Vaulted Dining Room with gas fireplace & French doors. Covered porch. Wraparound stone terrace. Primary bedroom suite

    Peter Klemm Klemm Real Estate Inc

    18 Arrow Point Rd, Warren, CT 06777
  • /40

    $899,000

    • 5 Beds
    • 3 Baths
    • 2,859 Sq Ft

    2 Surdan Mountain Rd, Sharon, CT 06069

    Great opportunity to own this expansive New England farm/horse property situated on 70+ acres with great views of the CT Litchfield Hills! This is an estate sized parcel adjacent to National Audubon Society owned land and features multiple homes, barns/garages and paddock. The main farmhouse was built in 1780 and has been added to over the years including a post and beam addition with first floor

    Peter Carbutti Carbutti & Co., Realtors

    2 Surdan Mountain Rd, Sharon, CT 06069
  • /39

    $12,995,000

    • 9 Beds
    • 12 Baths
    • 7,528 Sq Ft

    Unlisted Address

    A once in a lifetime opportunity to own over 230 acres overlooking Lake Waramaug. Nestled high in the hills overlooking the pristine beauty of the lake, this offering comprises six parcels of open fields and forest with exceptional views. Owned by the same family for the last 70 years, dignitaries from the worlds of art, politics, and industry have been entertained here while the stables,

    Pat Lahoud William Pitt Sotheby's Int'l

    Unlisted Address
  • /37

    $2,450,000

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

    293 Lake Rd, Warren, CT 06777

    Simply stunning long western views of Lake Waramaug and the Litchfield Hills! 16 acre 5 bedroom estate located minutes from the lake with access to Warren Town Beach, hiking trails at Steep Rock or the Warren Land Trust. Village of New Preston is only minutes away for dinning and shopping. Less than 30 minutes to skiing at Mohawk Mtn. 5 large bedrooms with 3 full and 4 half baths spread over 3

    Pels Matthews W. Raveis Lifestyles Realty

    293 Lake Rd, Warren, CT 06777
  • /39

    $8,750,000

    • 5 Beds
    • 5 Baths
    • 8,240 Sq Ft

    841 Winchester Rd, Norfolk Historic District, CT 06058

    Gracefully nestled at water's edge among lofty pines on over 115 utterly private and unspoiled woodland acres, this breathtaking lakefront country home features five bedrooms and four-and-a-half bathrooms and over 8,000 sq ft of luxurious living space. With extraordinary craftsmanship and exceptional materials, this custom built contemporary residence harmoniously integrates with its natural

    Jennifer Leahy Compass Connecticut, LLC

    841 Winchester Rd, Norfolk Historic District, CT 06058
  • /37

    $689,900

    • 5 Beds
    • 3.5 Baths
    • 4,550 Sq Ft

    96 Neill Dr, Watertown, CT 06795

    Motivated Seller! Charming Remodeled Colonial w/ in-law in one of the most sought out neighborhoods. Main house has 5 generous size Bdrms,2.5 bathrooms(Tile flooring), Layout boosts a spacious open floor plan w/ Family room & Kitchen w dining area, Formal Dining room open to Living Room, Mud room/Laundry room off the Garage. Hardwood floors throughout, Central air, Central Vac, custom solid-wood

    Christina Moulthrop Showcase Realty, Inc.

    96 Neill Dr, Watertown, CT 06795
  • /23

    $1,150,000

    • 15 Beds
    • 5 Baths
    • 5,755 Sq Ft

    243 N Elm St, Torrington, CT 06790

    ATTENTION INVESTORS! Turnkey 5-unit income-producing property in the desirable north end of town with a 7.72% cap rate! This fully occupied AND FULLY UPDATED multi-family includes one spacious 2-bedroom unit, three well-designed 3-bedroom units, and one 4 bedroom unit all with functional layouts. Recent upgrades include a new heating system and water heaters (2021), a newer roof, updated heating

    Chris Carozza RE/MAX Right Choice

    243 N Elm St, Torrington, CT 06790
  • /37

    $1,325,000

    • 5 Beds
    • 4 Baths
    • 3,427 Sq Ft

    31 E Hyerdale Dr, Goshen, CT 06756

    This dramatic Woodridge Lake home has year round western views of the lake, this home has all the newest features sought by home buyers today. The home offers picture sliders overlooking the deck, lake and backyard views. There are four bedrooms and 4 full baths featured in the floor plan. The great room/kitchen boasts a propane fireplace with a stone surround, as well as a convenient enclosed

    Stephen Drezen William Pitt Sotheby's Int'l

    31 E Hyerdale Dr, Goshen, CT 06756
  • /35

    $4,500,000

    • 5 Beds
    • 6 Baths
    • 5,940 Sq Ft

    8 Bayberry Hill, Roxbury, CT 06783

    Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a

    Graham Klemm Klemm Real Estate Inc

    8 Bayberry Hill, Roxbury, CT 06783
  • /39

    $3,349,000

    • 7 Beds
    • 9 Baths
    • 15,000 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
  • /39

    $4,321,000

    • 5 Beds
    • 8 Baths
    • 5,005 Sq Ft

    65 Hammertown Rd, Salisbury, CT 06068

    The post-and-beam residence showcases soaring ceilings and expansive windows that frame the spectacular landscape while highlighting the architectural character throughout. Natural materials-including local woods, native stone, and artisanal steel elements-create a sophisticated dialogue between interior spaces and the surrounding countryside. The heart of the main level features a grand Great

    Elyse Morris Elyse Harney Real Estate

    65 Hammertown Rd, Salisbury, CT 06068
  • /39

    $14,000,000

    • 5 Beds
    • 8 Baths
    • 10,203 Sq Ft

    220 Tinker Hill Rd, Washington, CT 06777

    Stunning Modernist Villa with Panoramic Views. Featured in Architectural Digest in August 2007, this dramatic property sits on a hillside with some of the most sweeping and magical views of Lake Waramaug. It was designed by award-winning architect Steven F. Haas and is situated on 18+/- beautifully landscaped acres, romantically designed by the well-known landscape designer Renny Reynolds with a

    Peter Klemm Klemm Real Estate Inc

    220 Tinker Hill Rd, Washington, CT 06777
  • /27

    $345,000

    • 6 Beds
    • 2 Baths
    • 2,826 Sq Ft

    58 Berry St, Torrington, CT 06790

    Back on the market! This oversized two-family home presents an excellent opportunity for investors or owner-occupants looking to maximize rental income. With many updates including conversion of the third-floor into a brand new one bedroom living space featuring a brand-new kitchen and bathroom, much of the major work has already been completed. The third floor could potentially transform this

    Tiffany Maldonado The Bella Group, LLC

    58 Berry St, Torrington, CT 06790
  • /40

    $5,450,000

    • 5 Beds
    • 7 Baths
    • 6,261 Sq Ft

    11 Valley Rd, Lakeville, CT 06039

    Sprawling Lakeville Compound On 21+ Acres - This idyllic gathering place boasts a 5-bedroom, 7-bath 6,261 sq. ft. Main House and a 3-bedroom, 2-bath, 1,987 sq. ft. Guest House overlooking a Heated 55-ft. Gunite Pool. The Main House was designed by renowned architect Alan Wanzenberg and landscaped by award-winning designer Susan Child. This compound offers peaceful seclusion and convenient access

    Elyse Morris Elyse Harney Real Estate

    11 Valley Rd, Lakeville, CT 06039
  • /7

    $649,000

    • 6 Beds
    • 3 Baths
    • 2,952 Sq Ft

    123 Littlefield Rd, New Milford, CT 06776

    Welcome to this charming, beautifully renovated antique home nestled in New Milford's historic north end. Boasting NEWER ROOF (4YRS OLD), UPGRADED WINDOWS, UPDATED BATHROOMS, NEW HARDWOOD FLOORS AND FRESHLY PAINTED... This home is a legal 2-family home which can easily be converted to a large single family. Both units have their own separate entrances. Rent both units for great rental income,

    Manny Patricio Misty Hollow Realty Group

    123 Littlefield Rd, New Milford, CT 06776
  • /39

    $950,000

    • 14 Beds
    • 7 Baths
    • 4,860 Sq Ft

    175 N Main St, Winsted, CT 06098

    Addresses include 175 Main Street and 183 Main Street in Winsted, CT. Amazing opportunity to acquire a 9 Unit Asset (7 Apartments + 2 Retail) in Winsted with anchor tenant Noli's Restaurant (Rent $2,266 w 3% increase/year) w over 20 years in business! Pride of Ownership is evident with Capital Improvements made by the current owners, including: new water heaters, heating zones, electrical

    Ryan Rea Berkshire Hathaway NE Prop.

    175 N Main St, Winsted, CT 06098
  • /40

    $8,000,000

    • 6 Beds
    • 9 Baths
    • 8,933 Sq Ft

    33 Nodine Pasture Rd, Kent, CT 06757

    West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open

    Jill Sloane Brown Harris Stevens

    33 Nodine Pasture Rd, Kent, CT 06757
  • /36

    $2,495,000

    • 5 Beds
    • 6 Baths
    • 3,743 Sq Ft

    9 Mallory Brook Rd, Washington, CT 06793

    Exceptional Washington Value. Wonderful Period Compound Replete with Main House, Guest House, Pool, Pond, Paddle Tennis & More! This Property Encompasses Both Sides of a Low-Traveled Town Road Merely 4 Min to the Village. 5 Bedroom, 3 Full & Two 1/2 Bath Main House + 2 Bedroom, 2 Bath Cottage + Heated Party/Sports Barn. A Terrific Floor-plan Includes: A Large Bright Eat-in Kitchen; Generous

    Graham Klemm Klemm Real Estate Inc

    9 Mallory Brook Rd, Washington, CT 06793
  • /37

    $515,000

    • 5 Beds
    • 4 Baths
    • 5,016 Sq Ft

    55 Walnut St, Winsted, CT 06098

    Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family

    David Sartirana Northwest CT Realty

    55 Walnut St, Winsted, CT 06098
  • /36

    $789,000

    • 5 Beds
    • 2 Baths
    • 1,876 Sq Ft

    202 Crane Hollow Rd, Bethlehem, CT 06751

    UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional

    Danielle Rownin Keller Williams Realty

    202 Crane Hollow Rd, Bethlehem, CT 06751
  • /23

    $749,000

    • 10 Beds
    • 11 Baths
    • 7,501 Sq Ft

    77 New Milford Turnpike, New Preston Marble Dale, CT 06777

    Potential awaits at this stunning antique stone home. The property was formerly used as a bed & breakfast and a retirement home. Currently used as a boarding house. The original 1800's stone bldg has additions to form over 7500 sq feet of living space Three separate entrances with two staircases. The main section hosts 9 bedrooms with 6 full baths and 4 half baths which share a communal kitchen

    Stacey Matthews W. Raveis Lifestyles Realty

    77 New Milford Turnpike, New Preston Marble Dale, CT 06777
  • /26

    $1,200,000

    • 5 Beds
    • 2.5 Baths
    • 3,307 Sq Ft

    77 Deer Hill Rd, Colebrook, CT 06021

    Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at

    MICHAEL CONLOGUE William Pitt Sotheby's Int'l

    77 Deer Hill Rd, Colebrook, CT 06021
  • /35

    $925,000

    • 5 Beds
    • 4.5 Baths
    • 4,400 Sq Ft

    5 Mountain Dr, New Milford, CT 06776

    Live by the Lake! Convenient commute to NYC. Beautiful Candlewood Lake is within moments from this lovely 5 Bedroom, 4 full and 2 half Bath "Contemporary" style home with 2 car attached garage. Perfect for those who work from home or multi generational living as this property provides opportunity for distance & privacy all under 1 roof. Level 1 consists of a large entry foyer that opens to the

    Aileen O'Connell Coldwell Banker Realty

    5 Mountain Dr, New Milford, CT 06776
  • /40

    $1,299,999

    • 8 Beds
    • 4.5 Baths
    • 5,231 Sq Ft

    435 W Wakefield Blvd, Winsted, CT 06098

    Welcome to this spectacular Highland Lake estate, offering a unique blend of luxury & tranquility. Situated on 1.3 acres of level land, the property includes a large barn/garage capable of housing multiple cars, boats, & equipment. The main home boasts generously sized rooms w/ high ceilings, offering an open, airy feel throughout. The kitchen has been updated w/ hardwood cabinets, featuring

    Heidi Picard-Ramsay Berkshire Hathaway NE Prop.

    435 W Wakefield Blvd, Winsted, CT 06098
  • /40

    $5,925,000

    • 5 Beds
    • 5.5 Baths
    • 9,165 Sq Ft

    51 Ferry Bridge Rd, Washington, CT 06793

    Built in 1885 as a Gilded Age summer retreat, Rock Gate is as well-known and celebrated in Washington as its architect: Ehrick Rossiter. Rossiter's generous rooms graced with restored carved butternut wood panels, walnut and fir floors, delicate turned spindles, alongside arched windows, porches, and turreted and gable roofs, define the Queen Anne shingle-style homes of the period. Updated and

    Maria Taylor Klemm Real Estate Inc

    51 Ferry Bridge Rd, Washington, CT 06793

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