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$2,950,000
7 Beds ⋅ 6 Baths ⋅ 24169503 MLS
This stunning 1874 Federal house sits on a 3.93-acre lot and backs up to land-trust property. It was fully renovated and designed by Percy Steinhart, the design maven who created Stubbs & Wooton shoes. The estate contains a 6,641 square foot Main House, plus a wonderful Pool House and Carriage House. In the Main House, the spacious Entry Hall leads to the Living Room with a fireplace and a charming bay window. A large Library with a fireplace opens into a spacious Garden Room. The elegant Dining Room has a corner fireplace and double exposures. Adjacent is a gourmet Kitchen with a large island, high-end appliances, and a sizeable breakfast area with a spacious Cloak and Powder Room nearby. The front and back staircases lead to the second floor and a Primary Suite consisting of a large bedroom with a bay window and fireplace, and an elegant en-suite Bath. A second Bedroom with a fireplace is adjacent to the Primary. Two additional Bedrooms with en-suite Baths, and a Laundry Room, complete the second floor. On the third floor is a center gathering room plus two large Bedrooms and Baths. A large, unrenovated room has potential for use as an additional Bedroom, Gym, or Office. The Basement has a two-car garage with a Half Bath and generous storage rooms. The property is beautifully landscaped with a Croquet Lawn, a large pool, and Pool House with an outdoor fireplace for cooking, and a Greenhouse. The Main House and Pool House have updated HVAC systems with Central Air.

148 North St, Litchfield
$2,600,000
4 Beds ⋅ 5 Baths ⋅ 24166876 MLS
On nearly an acre in the Borough of Litchfield, the 1775 Benjamin Tallmadge House is a rare offering in the Litchfield Historic District. A decade of museum-quality stewardship under the current owners has produced one of the most thoughtful restorations ever undertaken on a North Street residence, with every original architectural detail preserved. This antique Colonial blends preserved character with thoughtful updates, including original wide-board pine floors, plaster walls, refurbished Indian shutters, 10 fireplaces, and a chef's kitchen with soapstone counters, La Cornue range, butler's pantry, and built-in banquette. Four bedrooms are joined by a third-floor den currently configured as a 5th bedroom.The primary suite features a 2026 expanded glass-and-tile shower, walk-in dressing room, and cedar closets. Grounds by Michael Trapp include a 44-foot gunite pool, planted rooftop deck with 10-foot spa, tea house, gazebo, gas fire pit, and attached 3-car garage. This is the rare offering where architecture, national history, and daily livability all carry equal weight - a Georgian landmark with Revolutionary War provenance, museum-quality restoration, and a Trapp landscape compound, presented in turnkey condition for its next generation of stewardship.

47 North St, Litchfield
$2,255,000
4 Beds ⋅ 5 Baths ⋅ 170602941 MLS
Welcome home! Enjoy the holidays in this village home. Nothing to do but move in. Can be purchased furnished! Conveniently located in Litchfield Historic District. This gracious colonial is meticulously maintained. The main level consists of a very spacious kitchen with an open floor plan that opens to a comfortable family room, formal dining room with Fireplace, spacious living room with fireplace, light splashed sunroom, library with rich woodwork, FP & bookcases and a powder room. Upper level consists of a dedicated primary bedroom suite, dressing room built in cabinets.Additional en-suite bedroom. 2 other spacious bedrooms with 2 full baths, spacious Laundry room, office and exercise room. Lower level you will find a wine cellar. Professionally landscaped level yard with flower beds and fruit trees. 2 car attached garage that’s conveniently located to the mud room and kitchen. Additional 2 car detached oversized garage. Enjoy Litchfield village, shops, restaurants, library, museum and nearby White Memorial Foundation with numerous hiking trails and Bantam Lake.

42 Old South Rd, Litchfield
$2,188,000
5 Beds ⋅ 7 Baths ⋅ 24150605 MLS
In the heart of Litchfield's coveted Historic District, along one of the town's most admired streets, stands the circa-1855 Woodruff House, an iconic Italianate Victorian Villa and enduring centerpiece of the neighborhood. Built for prominent Litchfield resident George Morris Woodruff, this beloved home blends architectural pedigree with modern livability. Signature elements include a shallow hipped roofline, distinctive columned verandah, double-tiered gallery, and dramatic two-story octagonal bays, a rare and remarkably preserved example of the period. Inside, grand yet inviting spaces unfold: formal entry hall, multiple living rooms for gathering and quiet retreat, dining room, den, office, and a spacious kitchen opening to a comfortable family room. The home offers five bedrooms including two primary suites, along with four full and three half baths, allowing guests and owners alike to live graciously. French doors lead to a sunroom and deck overlooking mature, landscaped grounds designed for entertaining with two patios, an updated heated pool, and the kind of setting that makes weekends linger longer. Modern comforts integrate seamlessly: elevator to primary bedroom, generator, four fireplaces and laundry room. A heated two-story barn provides flexible space for studio, workshop, or collector storage with room for two vehicles. Moments to the Litchfield Green. A rare opportunity to own not simply a home, but a recognized piece of Litchfield's architectural legacy.

44 South St, Litchfield
$1,925,000
5 Beds ⋅ 4 Baths ⋅ 24011881 MLS
Remarkable setting on the Shepaug River in historic Milton section of Litchfield. 5 bedrooms, 3 full and 1 half baths. Main floor primary suite, 2 beds and full bath upstairs, 2 beds and full bath lower level with full windows/walkout. Fabulous great room with kitchen island, dinning, fireplace and sitting area that leads to outdoor living room overlooking yard and river. Large lower level media/rec/gym with ample storage areas remaining. The getaway you have been looking for! Close to Bantam, Litchfield Green, Washington, New Preston, Bantam Lake, Mohawk Mtn state park. Total privacy on 20+ acres.

19 Saw Mill Rd, Litchfield
$1,895,000
4 Beds ⋅ 8 Baths ⋅ 170571563 MLS
Stunning Contemporary Estate set in one of the highly desirable areas of Litchfield, just a short walk to acres of hiking/mountain biking trails. This architect designed gem offers 6.9 acres of lush plantings, level lawn and light woods along with tennis court, gunite pool and terrace with pergola, double grills and stone wall which make it perfect for outdoor living. The main level of the home with its gourmet kitchen offers butlers pantry, Wolf Range, separate Sub Zero refrigerator and freezer, commercial pizza oven along with a cozy family room and fireside conversation pit is the hub of the home. The double height living room with loft and a sumptuous dining room create a great place to entertain. In addition, there is 4 season porch w/Danish stove and a private artist's studio/office with separate entry, gym, laundry room and semi-finished wine cellar. The upper level features the primary suite with sauna, expansive closets, reading loft and luxurious bath. Additionally, there are 2 en-suite bedrooms, a vaulted family suite w/bedroom, playroom and 2 baths. An upper level Media room and office make a perfect place to work or enjoy a movie. This uniquely designed estate creates your own "private oasis," yet minutes to Litchfield Green for great dining and shopping! Amenities: Luxurious updated baths, highest grade Marvin windows/doors, pool, jacuzzi, tennis court, outdoor kitchen, bluestone terrace, pergola, perimeter deer fencing, 6 car garaging w/electric.. see more

254 Chestnut Hill Rd, Litchfield
$1,850,000
4 Beds ⋅ 4 Baths ⋅ 24012798 MLS
Welcome to 231 Maple Street, a meticulously restored 1799 colonial estate, where historic charm meets modern elegance and luxury. Nestled on 6.4 acres of beautifully landscaped grounds with a serene pond and extensive stonework, the property boasts breathtaking western views of the Litchfield Foothills and backs up to 180 acres held in easement with the Litchfield Land Trust. Just minutes from Arethusa Al Tavolo, Arethusa Farm Dairy, and Arethusa a Mano, as well as the Bantam Market, Bantam Bread, and the Litchfield Town Center, this exceptional offering provides a tranquil escape while remaining close to vibrant shops and renowned, award-winning restaurants. Step inside and discover a light-filled haven featuring a thoughtfully designed open concept layout on the main level. Wide-plank antique floors and exposed beams create a sense of warmth and character throughout the living areas. A stunning gourmet kitchen boasts top-of-the-line stainless steel appliances, a DeVol Kitchen brass faucet, top of the line light fixtures, quartz countertops, and a restored stone fireplace, original to the home. There is also a dedicated butcher block baking station. The kitchen, along with the adjoining living and dining rooms feature French doors leading out to a picturesque stone terrace overlooking the recently updated pool with bluestone surround, pea gravel hardscaping and captivating vistas. A delightful library with custom bookcases and its own fireplace provides a dedicated s

231 Maple St, Litchfield
$1,825,000
3 Beds ⋅ 4 Baths ⋅ 24083295 MLS
Step into the pages of history with the beautifully revitalized Col. Charles Webb house, circa 1830, a centerpiece of Litchfield's storied past. This iconic residence has been thoughtfully updated, blending classic elegance with modern amenities. As you enter through the entryway, you are greeted by the warmth of wide board flooring and an inviting arched doorway. The journey continues to a convenient wet bar and into the sunlit formal living room, where a wood-burning fireplace, built-in cabinets and polished hardwood flooring create an atmosphere of timeless charm. The formal dining room, with another wood-burning fireplace, offers ample storage and two closets. The great room is a marvel of architectural design, featuring a soaring ceiling, elegant French doors and luminous Palladian windows that invite the outside in. Culinary enthusiasts will revel in the chef's kitchen, boasting a gas range, dual new dishwashers, a Subzero refrigerator, a breakfast bar and a cozy dining area. A versatile mud/playroom and a half bath complete the main level's offerings. Ascend to the upper level, where the primary bedroom suite has been freshly painted and adorned with new oak floors and custom molding, creating a serene escape. The en-suite primary bath has been transformed with a new custom shower and linen closet. Two additional guest bedrooms (one en-suite) have undergone complete renovations, featuring new oak flooring, fresh paint and remodeled

102 North St, Litchfield
$1,800,000
7 Beds ⋅ 6 Baths ⋅ 170606380 MLS
Enjoy in-town living on a country estate in this Chic Country Antique on one of Litchfield's most sought after walk-to-town locations with an inground pool. This exceptionally updated light-filled home with 4 fireplaces has maintained its architectural integrity throughout the 1786 structure, and the later Italianate addition and is ideal for contemporary living. This classic has all the modern conveniences; new hardwood floors on most of the main level, an upscale and recently expanded & remodeled kitchen with heated floors, AC wall units in bedrooms, kitchen & office, recessed lighting, lots of closets & built-ins with up to date mechanicals and new generator. Bedrooms include a remodeled primary suite and bath with heated floors, 3 ensuite bedrooms, and 3 additional bedrooms with a remodeled full bathroom and heated floors on the 3rd floor for staff or guests. Professionally decorated, the paint colors, wallpaper, finishes & fixtures are to the highest standard. Privately set on 2.58 English inspired park-like acres of boxwood hedges, perennial gardens, mature trees, and vegetable garden, this quiet yard becomes your own oasis. Other features include a brick courtyard, a 3 car garage with new concrete floor and a newly created attached office. The lower level has access from backyard with a bathroom, gym & mudroom with new heated floors. An extraordinary amount of effort, creativity and skill went into remodeling this impeccable residence. Litchfield is your oyster!

55 Prospect St, Litchfield
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 24103342 MLS
Step into a harmonious blend of history and modern luxury at Bittersweet Ranch, a meticulously updated home home dating back to 1767, set upon 39 magnificent acres backed by state land for privacy and no neighbor obstructions. This exquisite property features diverse topography with meadows, trails and forests, ideal for horseback riding, hunting and birdwatching. The chef's delight kitchen boasts a gas range, electric oven, sleek stainless steel appliances, a farmhouse sink and granite countertops. The large sunroom is a haven for relaxation with brick flooring and sliding glass doors, while original wide board oak floors add timeless elegance. Entertain in the formal dining room with a rolling barn door and propane fireplace. The den invites gatherings with its custom built bar and woodstove. A well appointed office space is complete with built-in bookcases. Guests will revel in the ensuite bedroom with propane fireplace. The primary suite offers a walk-in closet, sliding door, ceiling fan and custom built bed. A media room and laundry room add convenience. The lower level features a mudroom, playroom, half bath, laundry area and a three-car garage. Outside, the expansive patio is perfect for entertaining amidst meadows. The property includes a 72 x 28 greenhouse with potential for a nursery and is adorned with berry patches and classic stonewalls.

93 Northfield Rd, Litchfield
$1,660,000
3 Beds ⋅ 3 Baths ⋅ 24027447 MLS
Introducing Windswept Farm: a quintessential New England retreat that masterfully blends the charm of its 1850 Colonial Farmhouse heritage with modern updates and expansions, all set upon 7 acres of pastoral beauty. This enchanting hobby farm is a dream for those with a passion for the outdoors and a love for equestrian pursuits, featuring a pristine four-stall stable constructed in 2015 and a versatile detached three-car garage with a spacious workshop above. The heart of the home is the updated kitchen, a culinary haven with Corian countertops, a farm sink and an island graced with a granite top. High-end appliances, including a Subzero refrigerator and dual dishwashers compliment the well-appointed pantry. The adjoining sunroom, with its radiant heat and French doors, offers a warm, light-filled space for relaxation or entertaining. Classic elegance defines the formal living room where a wood-burning fireplace and built-in bookshelves create a cozy ambiance. The dining room, with its wide-board flooring and second fireplace, invites formal gatherings, while the office space, complete with French doors and crown molding, provides a quiet corner for work or study. The main level also includes a convenient full bath and a mud/laundry room, ensuring practicality meets style. Upstairs, the primary bedroom suite is a luxurious retreat, boasting dual walk-in closets, wall-to-wall carpeting and a full bath with whirlpool tub, tile shower and dual sink vanity.

183 Goodhouse Rd, Litchfield
$1,600,000
4 Beds ⋅ 5 Baths ⋅ 170569864 MLS
Introducing the Col. Charles Webb house, circa 1830 centrally located in historic Litchfield. Features of this grand home include an elegant formal living room with woodburning fireplace; formal dining room with built-in cabinet and wood burning fireplace; chef's kitchen with gas range, island and Subzero refrigerator, wine cooler and breakfast bar, dining area; massive great room with vaulted ceiling and wood burning fireplace; French doors that lead to the terrace with gorgeous easterly views of the back yard. A large game room, wet bar and half bath complete the main level. The upper level showcases a library with built-in cabinets and recessed lighting; guest bedroom with full bath; guest bedroom with full bath across the hall; primary bedroom suite with luxurious bathroom and walk-in closet. An attached two-car garage is located under the house. An inviting inground Gunite, heated pool is located in the backyard along with a charming one-bedroom guest cottage featuring a cathedral ceiling, French doors, kitchen, and full bathroom. Beautifully maintained, lush gardens, mature plantings, white picket fence and circular, crushed stone driveway on an oversized 2.02 acre parcel complete this historic property. Mechanical features include central air and generator. A magnificent village home.

102 North St, Litchfield
$1,508,000
4 Beds ⋅ 4 Baths ⋅ 24037474 MLS
Superb views from this light-filled 4 bed, 3 1/2 bath country home that combines the best of classic details with modern and open living spaces. Built in 2022 by a well-known Litchfield County design and building firm, this home is sited to take advantage of the spectacular views of Mt. Tom and the surrounding countryside. The 4+ acre property includes an apple orchard, stone walls, and white fencing at the front entrance, and a tiered bluestone porch and terrace along with a rolling meadow at the rear. The interior is equally impressive with 10-foot ceilings on the first floor, top-of-the-line finishes, and impressive craftsmanship throughout. The stunning English-style kitchen, with its 48-inch range, massive island, and separate bar area, opens to a sun-filled living/family room with a wood-burning fireplace and an adjacent dining area with a vaulted ceiling and sliding doors leading to the terrace. An office with built-in cabinets, a front-entry mudroom, spacious pantry, powder room, and three-car garage complete the first floor. Upstairs consists of the primary bedroom and elegant bath with double custom vanities, an ensuite bedroom, and two other bedrooms joined by a full bath. A large loft area, two linen closets, a laundry room, and ample walk-in closets complete the second floor. The property is graciously landscaped with numerous trees and plantings, a stone circular drive, bluestone walkways, and a custom potting/tool shed. Builder's own home.

248 Old Mount Tom Rd, Litchfield
$1,500,000
3 Beds ⋅ 4 Baths ⋅ 24006040 MLS
Unique & Special Litchfield County Waterfront Property: Perfect for those who want year round water views, serenity and privacy. This contemporary home with post & beam construction is ready to move in with renovated kitchen and baths, abundant natural light, and room to spread out. Usable space much larger than stated square footage. 3 large Bedrooms + Bonus/Guest Room, 3.5 Baths, main floor primary suite, and an inviting glass-enclosed porch. The home is smartly designed to appreciate water views from many of the rooms, with multiple outdoor decks, patios, a firepit, and easy access to your private dock. Perched right on Lake Floren, a private pond-like body of water that is perfect for swimming and kayaking. Truly great location, less than 5 minutes to downtown Bantam (Arethusa, Bantam Market) and 5 minutes to the Litchfield town green.About two hours from NYC but a world away in bucolic Litchfield County.

272 Brush Hill Rd, Litchfield
$1,495,000
6 Beds ⋅ 4 Baths ⋅ 24039496 MLS
Nestled in the historic village of Litchfield, this circa 1940 colonial has been masterfully reimagined by a local architect, offering a seemless blend of classic charm and modern sophistication on a meticulously landscaped acre lot. As you step inside, you're greeted by an open floor plan that boasts a chef's kitchen equipped with top-of-the-line stainless steel appliances, including a Viking gas range. The large center island, cathedral ceiling, recessed lighting and built-in hutch all contribute to the kitchen's allure, making it a culinary artist's dream. Adjacent to the kitchen, the spacious dining area features elegant French doors that open to the private backyard, creating an ideal flow for indoor-outdoor living. The sophisticated L-shaped living room is a study in refinement with a wood-burning fireplace, custom built-in cabinets and wide board flooring that exude a sense of warmth and history. The glorious sunroom is a true retreat with radiant heat, limestone flooring and walls of windows that invite natural light to dance across the space. A practical mudroom with wide board flooring, laundry area and a half bath adds to the home's functionality. Retreat to the tranquility of the first floor primary bedroom suite, complete with engineered wood flooring, a bay window and a luxurious spa bathroom that promises relaxation and rejuvenation. The upper level is a haven for guests, showcasing four bedrooms with refinished hardwood floors, one of which includes

96 Prospect St, Litchfield
$1,425,000
6 Beds ⋅ 5 Baths ⋅ 24002779 MLS
Located in a neighborhood of iconic Colonial Revival homes, this Litchfield landmark allows you to be part of local history. "Sunnymead" was built by Henry R. Jones c. 1840 and extensively renovated by the current owners, who skillfully reconfigured and modernized main living spaces and systems, while preserving the charm and classic details of an historic residence. The main level boasts a grand central hallway, sweeping staircase, lofty ceilings and light-filled voluminous spaces for formal entertainment and casual living. Upper level includes primary bedroom suite with fireplace, dressing room, full bath. Three additional bedrooms with newly renovated bathrooms, millwork and high-end decorative features. The renovated third floor includes recreational space, dual office, gym, media room and full bath. New roof, rebuilt chimneys, central air and updates to plumbing, electric and insulation complete the effort. Professionally designed landscaping with specimen trees and re-laid original Belgian Block masonry. Three classic porches and restored porte-cochere. Very desirable location among notable Litchfield residences. Walk or bike to restaurants, shopping, Litchfield Green, library, White Memorial and the Greenway. An extraordinary amount of effort, planning and skill went into restoring this impeccable residence.

221 North St, Litchfield
$1,356,000
3 Beds ⋅ 5 Baths ⋅ 24093088 MLS
RARELY AVAILABLE PROPERTY NEAR VILLAGE ~ SPACIOUS ROOMS~ FIRST FL PRIMARY SUITE ~ GREAT ROOM WITH FP ~ UL MEDIA ROOM~ 3AC LANDSCAPED ~ 3-CAR-ATTACHED GARAGE W LOFT. Elegant yet comfortable, this expansive 4765sf Cape-style home with spacious rooms, is set on a beautifully manicured and professionally landscaped 3-acres. The setting provides peace and tranquility, yet it is only minutes from the village of Litchfield. Step inside where you are greeted by tasteful decorations that compliment the home's classic architecture with modern amenities. Perfect for entertaining or a quiet evening at home, the main floor with 3 Fireplaces, includes a formal Living Room, Dining Room, Pantry and gourmet Kitchen that opens to a Great Room with a dining area overlooking the terrace, woodland gardens and pond. The hallway includes a laundry room, wine room and half-bath, connecting to a breezeway and attached 3-car garage with an upper level that has great potential. The Primary suite and full bath, guest half-bath and en-suite 2nd bedroom, complete this level. The upper level includes a 3rd bedroom with generous closets,full bath,hallway cedar closet and a media room and large home office with skylights that has potential to become a 4th BR. A generator and CAIR are just some of the amenities included. Enjoy fine dining in area restaurants, boutique hotels and inns, shopping, golf, boating, hiking, horseback riding, nature trails, Topsmead State Forest and White Memorial Conservation Cen

39 Fern Ave, Litchfield
$1,350,000
5 Beds ⋅ 4 Baths ⋅ 24098258 MLS
LOCATED IN THE HEART OF HISTORIC LITCHFIELD on one of the town's most celebrated streets, this South Street residence offers a rare opportunity to own a piece of Connecticut's past. Known as the Huntington-Andrews House, this c.1800 home was once the residence of Charles B. Andrews-Connecticut's only Governor to serve as Chief Justice-making it a true local landmark. SET AMONG other stately Colonial homes, the property has been comprehensively renovated to blend classic character with modern comfort. NEW HEATING/AC SYSTEM. NEW ROOF AND SOLAR PANELS INSTALLED IN JUNE/JULY 2025. Interior features include 9' ceilings, an elegant staircase, and light-filled spaces designed for both entertaining and everyday living. MAIN LEVEL: A beautifully appointed kitchen with radiant heat, custom Vermont cabinetry, and high-end appliances anchors the main level. Spacious rooms with excellent flow and elegant millwork. UPSTAIRS, primary suite includes a fireplace and bay window, private dressing area, lovely bath, and a flexible room ideal for an office or nursery. The front bedroom uses a charming hall bath with vintage claw-foot tub and fireplace. Two other bedrooms share a Jack 'n Jill bath. THE PROPERTY has undergone significant landscape and structural improvements ensuring both beauty and soundness. Just a short walk to the Litchfield Green, museums/shops, fine dining, and nature trails, this home offers historic distinction in a storied Litchfield County town.

118 South St, Litchfield
$1,320,000
4 Beds ⋅ 4 Baths ⋅ 24008864 MLS
Welcome to 171 South Street - the historic former carriage house to one of Litchfield's most iconic residences - originally designed by "guilded age" architect Ehrick Rossiter. Extensively renovated over the years, owners reconfigured and modernized main living spaces and systems, while preserving classic details. The main level boasts a central hallway, leading to spacious open living room with wood burning fireplace and a garden room with VIEWS down sweeping lawn. Formal dining room, cozy den, chef's kitchen and bonus room currently used as a bedroom on main floor with full bath. Upper level includes primary bedroom suite with dressing room, full bath and two additional bedrooms with renovated bathroom AND a private office. New roof, rebuilt chimneys and updates to plumbing, electric and insulation complete the effort. Landscaping with native specimen plantings. Deck with southeastern views of neighboring meadow and hot tub. Private access to bordering Bantam River and White Memorial Conservation land through backyard trails. Very desirable location among notable Litchfield residences with access to nature. Walk or bike to restaurants, shopping, Litchfield Green, library, White Memorial and Greenway. Best of both worlds - in-town living in PRIVATE natural setting.

171 South St, Litchfield
$1,300,000
4 Beds ⋅ 4 Baths ⋅ 24163053 MLS
A Vintage Revival! Circa 1756 Historic Saltbox on 7 acres of level, sunny, totally useable acres in the Litchfield CT is completely renovated top to bottom; this is a home that marries the best of both the past and the present for modern living. Preserving the antique details and charm with new baths, a new kitchen and four new out buildings to the property the result is a home that's simple, clean, cozy and encourages outdoor hobbies/activities and offers endless live/work possibilities in a quiet country setting. There are exposed beams, hardwood floors throughout, multiple fireplaces, Plaster walls. Off the side of the house a wonderful stone terrace for entertaining complete with a pergola and a wood burning pizza oven. Take in the views of the open meadow and star glaze at night. A two car garage with gym area above offers tons of storage. A large post and beam barn for equipment could become a studio or guest house. There is even a chicken coop, an Orchard with a variety of apple trees, peach, cherry, and pear trees as well as 600+ different varieties of Xmas trees, a greenhouse, a chicken coop and a pond. There is room for a pool. This is an all American Classic only better!

566 Maple St, Litchfield
$1,300,000
3 Beds ⋅ 5 Baths ⋅ 24124922 MLS
In the heart of historic Litchfield CT, this 2004 colonial sits on a private 1-acre flag lot a short walk to the Green. 4,065sqft with an open, light-filled layout, 9ft ceilings, and wide-plank white oak floors. The great room with fireplace connects to the 2023 kitchen with granite counters, GE Cafe appliances, a Viking wine fridge, and a Miele steam oven. A library with a 16.5ft cathedral ceiling has radiant heat. A powder room with brick courtyard tile, a laundry with granite-effect tile and large sink, and a mudroom with a half bath complete the main level. Upstairs, the primary suite has a tray ceiling, Italian-tiled bath with radiant heat, and plumbing for a spa tub. 2 additional en-suite bedrooms have custom-tiled baths (1 with spa tub). A 400sqft bonus room with window seats sits over the 3-car garage.The 1,600sqft walkout basement (8ft ceilings, historic windows) suits a gym, office, or apartment. Exterior features include a columned entry with granite steps, red brick walkways, 46 Woodwright windows with custom trim/shutters, a paved 24ft driveway with turnaround, and a 3-car garage with 10ft bays, workshop, and masonry floor. A private deck, hot tub, landscaped gardens, evergreens, and fieldstone walls create a quiet in-town setting.Systems: 4-zone geothermal on the 1st floor; oil furnace with AC upstairs; rubberized basement walls; 20-gpm well; city sewer; 240V outlets; insulated attic;Recent updates: GAF roof (Oct 2024), , fresh Benjamin Moore exterior paint.

68 South St, Litchfield
$1,300,000
5 Beds ⋅ 4 Baths ⋅ 170606618 MLS
Located in a neighborhood of iconic Colonial Revival homes, this Litchfield landmark allows you to be part of local history. The c. 1800 Huntington-Andrews house was home to Judge Charles B. Andrews who later became both Governor and Chief Justice of Connecticut, the only person ever to hold the State's two highest offices. The entire property was extensively renovated by the current owners, who skillfully reconfigured and modernized main living spaces and systems, while preserving an historic residence. The main level boasts a grand central hallway, sweeping staircase, lofty ceilings, light-filled voluminous spaces for entertaining guests and family - as well as a cozy den to settle in front of the fireplace. Chef's kitchen with Vermont crafted cabinetry, large working island, high end appliances, new countertops, tile work and radiant heat. Upper level includes a major reconfigured primary bedroom suite with fireplace, dressing room, full bath and an office or nursery. Two additional bedrooms share new jack-and-jill bathroom. Fourth bedroom has bathroom with period piece claw-foot tub and bay windows. Extensive landscaping and structural work was done to improve the quality and integrity of the home. Very desirable location among iconic Litchfield residences. Walk or bike to restaurants, shopping, Litchfield Green, library, White Memorial and the Greenway. An extraordinary amount of effort, planning and skill went into restoring this impeccable residence.

118 South St, Litchfield
$1,295,000
4 Beds ⋅ 5 Baths ⋅ 24016888 MLS
Tucked away in one of Litchfield's most desirable locations on the Litchfield / Washington border, this country colonial has undergone an extensive and meticulous renovation in 2023/2024. Set far back from the road on a large 6.53 acre parcel, its location commands stunning views of Mt. Tom and the surrounding hills of the Shepaug Valley. This unique parcel is composed of two approved building lots, providing great opportunity for future expansion/development. Originally built in 1951, this four- bedroom, three full and two-half bath home has been completely transformed to include a NEW, huge kitchen with two dining areas, quartz countertops, and a ten-foot center island that allows for easy entertaining. The versatile, circular first floor plan includes a family room with a wood-burning fireplace and a bank of French doors leading to the expansive deck, a step-down sunroom with exposed brick, and a library/media room also with a wood-burning fireplace and built-ins. Most striking is the cherry wide-plank flooring that is found throughout the entire house adding country elegance to the bright interior. Upstairs, the spacious primary suite has a fireplace, walk-in closet, and a NEW high-end bathroom with soaking tub and walk-in shower. Two other bedrooms are joined by a NEW Jack-and-Jill bathroom, while the fourth bedroom is an ensuite, also with a NEW bathroom. Charming and original built-in dressers and drawers remain in some of the bedrooms.

240 Old Mount Tom Rd, Litchfield
$1,275,000
4 Beds ⋅ 3 Baths ⋅ 24188011 MLS
Wonderfully maintained center hall colonial on 10 acres bordered by protected land. This peaceful 3,200 sqft home features large open concept kitchen and living room with cozy gas fireplace and access to the spacious deck overlooking the back yard and pool. Through the cozy den with another gas fireplace you can enjoy endless summer nights on the large screened in porch, finishing off the main floor isn an oversized dining room with additional seating area and stunning decorative stone fireplace mantle. Upstairs features 4 spacious bedrooms including a large primary suite with walk in closet and access to an additional sitting area/office space. Through the sitting area and with Additional access from the lower level to the finished rec room above the garage is perfect for additional guests. Large basement has tremendous opportunity for additional living space with exterior and garage access. Outside, the private large pool with automatic pool cover is perfect for long quiet summer afternoons. Don't miss the chance on this private oasis in Milton!

469 Milton Rd, Litchfield
$1,250,000
3 Beds ⋅ 3 Baths ⋅ 170583846 MLS
UNDER CONTRACT. Net Zero Country Mini Estate: Just 90 miles from NY City, near bustling Bantam Village is a surprising 2366 sq. ft. gem. At first glance, Swallowtail Farm's 5.2 acres looks like a classic New England farm, with sweeping views of the iconic Litchfield Hills. But this 2016 net zero luxury build utilizes solar and geothermal, producing all of the energy needed for A/C, heat, hot water, electricity, EV charger. A wide foyer leads to a sunny, private office with built-ins and French doors to a patio. A large, open concept kitchen, dining, living area features rows of windows, streaming sunlight and tranquil views of swallows swooping the meadow. A dream for entertaining, this space flows onto a gorgeous patio with built-in grill and fire pit area. Premiere quality white oak cabinets, soapstone countertops, dry bar/wine chiller, stainless steel appliances, walk-in pantry. Custom wire-brushed, white oak wide-width floorboards throughout the house feel warm underfoot. Genius floor plan with side entry, powder room, cubbies, laundry. First-floor primary suite with scenic views and primary bath with oversized shower, double vanity, water closet. Two more bedrooms up, full bath in hallway, storage rooms. Two post and beam outbuildings (with electric) offer multiple uses: 768 sq. ft. two-car garage with work area, full upper loft. 624 sq. ft. red barn with 50' x 80' electric-fenced irrigated garden. Whole house propane generator. Survey in supplements.

159 Old Mount Tom Rd, Litchfield
$1,250,000
3 Beds ⋅ 4 Baths ⋅ 24125636 MLS
Perfect country home impressively set in private location abutting White Memorial land trust and vineyard. Designed with impeccable taste and style and built of the highest quality and standards. In keeping with its romantic European style, the home boasts lofty ceilings, marble floors, french doors, limestone fireplaces and mahogany millwork throughout. Perfect for entertaining as dining and living spaces open onto stone terrace with western views and overlooking pond and grounds. Established gardens, ivy clad walls and old world stone work. Chef's kitchen with room for eat-in country table. Stainless steel countertops and professional grade appliances. Master suite with beautifully crafted built-ins. Well appointed master bath with marble throughout. Major feature includes a newly built 1 bedroom attached in-law apartment that can be rented. One owner, very well maintained and exactly one mile from the Litchfield town Green. Perfect for full time OR weekends.

28 W Chestnut Hill Rd, Litchfield
$1,225,500
4 Beds ⋅ 3 Baths ⋅ 24120717 MLS
Set on 6.43 scenic acres at the foot of Cathole Mountain, this quintessential New England Colonial is paired with a beautifully restored barn-style guest house. Both antique structures have been thoughtfully renovated with a significant investment in energy-efficient infrastructure, blending historic charm with modern performance. The main house-lovingly known as Thyme Haven Farmhouse-features spacious rooms with original maple flooring and abundant natural light throughout. An impressive chef's kitchen anchors the main level, complete with a breakfast bar, walk-in pantry, 6 burner gas range, Sub-Zero refrigerator, and additional refrigerator drawers. A glass sliding door leads to the screened porch which offers views of the beautifully landscaped grounds, consisting of fruit trees and mature plantings. Adjacent to the kitchen is a bright dining room with a bay window and skylights, as well as a large mudroom/storage room. Two additional bay windows flank the spacious living room, which features a fireplace and two distinct seating areas-ideal for both entertaining and quiet evenings at home. A main-level bedroom with its own private powder room completes the first floor. Upstairs, you'll find two generously sized guest bedrooms, each served by a fully remodeled hallway bathroom. The expansive primary suite offers a second beautifully renovated bathroom, a large walk-in closet, and a private balcony.

87 Cathole Rd, Litchfield
$1,185,000
3 Beds ⋅ 2 Baths ⋅ 24052042 MLS
Expansive direct waterfront ranch on Connecticut's largest natural lake, Bantam Lake. This 3 bed 2 bath year round home is situated at the waters edge with 100' ft of private unobstructed shoreline. Bring your boat, the floating dock has been stored but is ready for next season. The wrap around deck is accessed easily from the great room and open concept kitchen/dining, perfect for entertaining and indoor/outdoor living. The walkout high ceiling basement is ideal for easy expansion, almost doubling your square footage! Central AC, recessed lighting, fireplace, updated vanities and decking, this house is move in ready. Not affiliated with an HOA has allowed for lucrative rental income, short or long term. Just minutes from downtown Bantam, White Memorial Nature Preserve, and Sandy Beach biking/hiking/boating and 5 star restaurants are ready to enjoy.

5 Breezy Knls, Litchfield
$1,170,000
5 Beds ⋅ 3 Baths ⋅ 170600108 MLS
NOW PRICED AT $1,295,000, All dressed up and ready for you to enjoy this summer. The Beckwith-Seymour house, built in 1817, is a fine example of the Federal period style. Set on iconic South Street in historic Litchfield, CT., The current owners have lovingly restored this 10 room colonial with many high-end features. A new English style kitchen, with hand rubbed white oak floors, English brass hardware, Bertazzoni range, Bosch refrigerator/freezer, Miele DW, Ruvatti farmhouse sink, DeVol window hardware, are just some examples. The new CAIR, high-velocity system, provides efficient cooling throughout. New Interior and exterior lighting including, George Nelson & Louis Paulsen has been installed. Attractive and cozy mudroom, immaculate attic, basement & garage. Totally renovated two-story screened porches. Large laundry room and powder room on main floor. New chimney liners. Delightful 2nd floor with 6 rooms, a TV "snug", sitting room/office, two bedrooms and a primary bedroom suite with additional sitting room. Lush private gardens have been installed by well known garden designer with fruit trees, antique stone terrace and a secluded back meadow with a lounging area. This home is ready for your family to move in. Enjoy all that the Litchfield village center and beyond has to offer! 2 hrs. to NYC. Enjoy dining, shopping, hiking, boating ,skiing & more in one of the prettiest towns in northwest CT. NOW PRICED AT $1,295,000. Most furnishings are available upon request

24 South St, Litchfield
$1,160,000
3 Beds ⋅ 4 Baths ⋅ 24044419 MLS
Nestled away in the hills of Litchfield, this private oasis gives peace & tranquility! This gorgeous 10 acre, park like setting with its own private pond awaits you. This spectacular 3 bedroom 3.5 bath Cape sits on just over 10 acres of park like grounds with its own private pond!! Enter through a new mahogany door into a beautifully open main floor which really allows for entertaining. Kitchen has all newer Viking appliances, 6 burner gas stove, 2 ovens, walk in pantry, vaulted ceilings, live edge island with ample seating, vaulted ceiling and wood beams throughout and a fireplace in the kitchen!! Living room also has a fireplace and open to a beautiful octagon shaped sun room with stone walls and slate floors which leads you out to a cozy patio ideal for morning coffee while listening to the birds and overlooking your beautiful, natural looking in- ground, heated saltwater, gunite pool. Off the kitchen you'll find a master wing with washer/dryer, onsuite and dressing area. Upper third floor has two bedrooms and a newly remodeled Jack & Jill. One is being used as an art studio taking advantage of the gorgeous natural light. Lower third level has a bedroom, full bath and den/rec room with private entrance right out to the pool! Potential in-law. Basement is another 2400 sq ft with work areas, tons of storage and seperate entrance to outside. 3 car garage also has full storage bay and above loft to make your own! All buildings have new roofs as of 2018. Updated list avail

66 Headquarters Rd, Litchfield

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