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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
$2,188,000
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
$1,825,000
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
$1,700,000
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
$1,356,000
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
$1,300,000
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
$1,275,000
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 ⋅ 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
$1,150,000
4 Beds ⋅ 5 Baths ⋅ 24169204 MLS
Welcome to Riverbend Farm, in the Borough of Litchfield. The property includes almost 7 acres with over 1,000 feet of frontage on the Bantam River! Set back from the road, is 415 South Street, the 6.7 acre parcel, with four structures, house, garage, garden shed and three stall barn. With stunning views of rolling property down to the river this Mid Century home has a flexible floor plan that features 4 bedrooms, 4.5 baths and over 4,000 sqft. The walk out living area has walls of windows overlooking a large blue stone patio, pool with flower garden, mature trees, rolling hill down to the river. The heart of the home includes: kitchen, dining area and 2 seating areas, one with a fireplace. With custom cabinetry, granite counter, gas cooktop and two ovens, microwave and a huge island, the spacious kitchen has ample space for multiple cooks. Adjacent to the kitchen is a half bath with laundry and a walk in pantry. The primary suite, on the entry floor, has a wall of windows, a gas fireplace, hardwood floors and French door access to a patio and the in-ground pool. This room has a large en-suite bath with a double sink. Adjacent to the entry is one of the bedrooms/home office/library/den spaces with large windows and hardwood floors.

415 South St, Litchfield
$1,060,000
6 Beds ⋅ 7 Baths ⋅ 24140724 MLS
A rare opportunity to own a piece of Litchfield history. This stunning Colonial Revival residence graces iconic North Street, one of Connecticut's most distinguished addresses. Built by Julius Deming for his daughter, Clarissa Deming Perkins, this architecturally significant home is a contributing property to the historic character of Litchfield's celebrated streetscape. Spanning 4910 sf, this home offers 12 gracious rooms and 5 fireplaces with 4 en-suite bedrooms upstairs and 2 bedrooms in the rear of the main level, a potential in-law or guest area. Period details and timeless design are evident throughout, from the authentic colonial revival fence-an excellent example of the era- to the classical proportions and refined millwork. This is more than a home, it is a stewardship opportunity for those who appreciate historic preservation and New England's architectural heritage. Live on one of the most photographed and admired streets in Litchfield, where every season brings new beauty to this treasured setting. Ready for the next chapter and waiting for your inspiration and thoughtful design ideas. Enjoy fine dining, shopping, antiquing, hiking, skiing, lakes, horseback riding, all conveniently close by, the Litchfield village is steps away, close to Bantam, Washington, 2hrs.+- to NYC Come home to the Hills!

124 North St, Litchfield
$910,000
3 Beds ⋅ 4 Baths ⋅ 24122414 MLS
Tucked away on 8 private acres at the end of a cul-de-sac, this Bantam Cape Cod offers some of the best views in Litchfield County! Rolling lawns and panoramic vistas create a setting of unmatched beauty and tranquility. The home's interior is refined and thoughtfully designed, showcasing an open, airy floor plan. The main-level primary suite offers comfort and privacy, while the upper level includes two additional bedrooms, a full bath, plus a spacious bonus room and office. The kitchen is outfitted with stainless steel appliances, a center island cooktop, a breakfast bar, and an informal dining area that flows seamlessly into the family room. A formal dining room provides the perfect setting for gatherings and holidays. The rear of the home features a large deck that overlooks rolling greenery, ideal for entertaining or simply soaking in the scenery. The newly finished walkout lower level elevates the home with a custom bar, movie lounge, game area with pool table, and an additional full bath, creating the ultimate retreat for relaxation and entertaining. Located in the sought-after Bantam section of Litchfield, you're just minutes from Arethusa ice cream, bakery, and restaurant, Bantam Market, Krafted Brew Lab, and other local favorites. Bantam Lake is also less than five minutes away, blending country living with modern convenience. A rare opportunity to own a refined retreat with forever views in one of Connecticut's most desirable destinations.

35 Peach Orchard Ln, Litchfield
$873,500
3 Beds ⋅ 4 Baths ⋅ 24172315 MLS
Ridge View where summer evenings are spent gathered around the fire pit, and winter days by the wood stove, watching snow fall across the valley. If you've been searching for privacy, sweeping views, and land roam, this is it. Set on over 13 acres, the property unfolds with hidden cleared pastures and meandering trails, ready to be reimagined. Whether you envision horses, livestock, or simple summer strolls along your own private trails. In addition there is over 14 acres of community land that is accessible for exploring. Perched atop a hill, the home takes full advantage of its surroundings. Southern exposure and abundant windows fill the interior with natural light and welcome warmth through the colder months. Inside, beautiful pine flooring and a striking stone hearth anchor the living space, creating a cozy and inviting focal point. The main-floor primary suite is a retreat of its own, complete with a private bath, two walk-in closets, and direct access to the deck. Where each morning begins with a view. The kitchen is well-appointed with a gas range, double ovens, and a pantry, while the main-floor laundry, breezeway, and half bath are thoughtfully positioned for days spent outdoors when coming in with muddy boots is part of the routine. Upstairs, two additional bedrooms offer generous closets and charming bonus spaces-perfect for secret play areas or quiet homework nook and share full bath.

25 Spruce Dr, Litchfield
$840,000
4 Beds ⋅ 4 Baths ⋅ 24162889 MLS
Newly renovated Litchfield Riverfront Oasis with pool, four bedrooms and a designer's eye throughout. This thoughtfully reimagined 4-bedroom Colonial sits on 2.85 park-like acres that lead directly to frontage on the Bantam River. At the heart of the home is a true Chef's Kitchen -showcasing Dekton countertops (the preference of culinary legend Thomas Keller), a Bertazzoni range + hood and an expansive appliance garage. The open-concept main level flows seamlessly from the formal living room with gas fireplace to a sun-drenched sunroom with French doors, leading to a composite deck and heated in-ground pool. Every inch has been refined, from the refinished hardwoods and designer lighting to the newly epoxy-floored home gym/garage. The upper level features a spacious Primary Suite with newly renovated bathroom and walk-in closet (with custom built-ins). Along with three additional guest bedrooms with hardwood flooring. The partially finished lower level includes a full bath and abundant storage. Enjoy mature Japanese Maples, stunning cherry tree and raised garden beds in a quiet country setting just minutes from Litchfield Green, Morris, and Washington. Whether a weekend retreat or full-time residence, your riverfront oasis awaits.

352 Norfolk Rd, Litchfield
$806,500
3 Beds ⋅ 3 Baths ⋅ 24111118 MLS
RARE FIND CUSTOM BUILT STUNNER! NEW CONSTRUCTION. Another Quality Home by Litchfield County Builder. Comfortable Living is found in this 2,500 Sq. Ft. Home all on one level! Capacious Open floor plan having a Contemporary Flair! Main core area offers a Welcoming "Great Room" Layout. Extraordinary Floor to Ceiling Granite Stone Fireplace. Beautifully designed baths. Spacious bedrooms! Attractive Kitchen has Granite Counters, Center Island and a Plethora of Cabinets. Special Features: Propane Heat, Central Air, 200 Amp Electric, Cathedral Ceilings. Skylights, Recessed lighting throughout, Lighted closets. Oversized Deck, Central Vac and 3 Bay Attached "Clear Span" Garage. Huge Basement with its own access. Level and lightly wooded 5.19 acre lot. Countryside location yet within Close Proximity to the Litchfield Village Green and surrounding towns for Shopping, Medical Facilities, Restaurants, State Parks, Lakes, White Memorial, Cultural and Art Venues. 2 Hours to New York City, 2.5 hours drive to Boston and a 45 minute drive to the Lovely Berkshires. One Fabulous Custom Home!

10 Maple View Trl, Litchfield
$775,000
4 Beds ⋅ 3 Baths ⋅ 24154290 MLS
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 character with comfortable and updated modern living. Offering 4 bedrooms and 2.1 baths, the home retains its timeless farmhouse appeal while providing generous living space. The property is well-equipped with a 378 sq ft 1-story barn with a fenced paddock - perfect for small livestock or equestrian pursuits. There is also a poultry house, a 2-bay garage, and a 664 sq ft workshop/studio. Relax and take in the pastoral setting from the inviting screened porch. A rare opportunity to own a restored New England farmhouse offering acreage, charm, and versatility. Property consists of 2 adjacent parcels. House on 7.32 acres and 1.8 acre lot in Goshen. Taxes for both pieces is $7,136.70.

403 Beach St, Litchfield
$775,000
4 Beds ⋅ 4 Baths ⋅ 24131076 MLS
Opportunities like this don't come along very often so don't miss your chance to bring back to glory this incredible period 10-room Center-Chimney Colonial on 27.03 acres minutes from Litchfield Center! Beautiful wood beams, period details, 4 fireplaces and original floors are just a few details that provide that colonial charm while the home features a flexible floor plan and first floor primary suite for today's modern living. The 27 acres features almost 800 feet of frontage of E Litchfield Rd and Buell Rd across from Topsmead State Forest with beautiful stone walls, historic trees and two barns. Just two miles from Litchfield Center this property offers privacy and tranquility while being close to everything Litchfield County has to offer. This property is truly a must see, your opportunity awaits!

182 E Litchfield Rd, Litchfield
$770,000
4 Beds ⋅ 3 Baths ⋅ 24145766 MLS
Classic 1925 Colonial in Litchfield's Historic District Discover timeless elegance at 137 Old South Road, a well maintained 4-bedroom, 2.5-bath Colonial set on nearly three-quarters of an acre in Litchfield's coveted Historic District. Built in 1925, this 9-room, 2,702-square-foot home showcases the craftsmanship and charming period details that define classic New England architecture. Step inside to find well-proportioned living spaces that balance historic character with comfortable, everyday living with fireplace. Four generous bedrooms provide flexibility for family, guests, or a home office, while two and a half baths offer modern convenience. A finished 3rd floor completes this interior with a well-defined space for an office, exercise room, play area or quiet retreat with generator. A Lovely open porch on the south side, perfect for entertaining. The .7-acre grounds provide a peaceful setting with room to garden, play, or simply enjoy the changing seasons. This prime in-town location offers the best of Litchfield living-walkable to the village's specialty shops, galleries, and restaurants, yet just moments from the 4,000-acre White Memorial Conservation Center, where miles of trails await hikers, bikers, and nature lovers year-round. Enjoy Topsmeade State Forest, area skiing at Mohawk Mtn. A rare opportunity to own a piece of Litchfield history with the ease of in-town convenience.

137 Old South Rd, Litchfield
$765,000
5 Beds ⋅ 4 Baths ⋅ 24140262 MLS
Period Details | Modern Comfort | Room to Grow Welcome home to 11 West Chestnut Hill, a remarkable piece of Connecticut history now awaiting its next chapter. This magnificent 5-bedroom, 3.5-bathroom property is set on 1.6 picturesque acres, ideally nestled just a half-mile from the historic Litchfield town green. Lovingly hand-built in 1804 by Stephen Clark for his wife and daughter on the site of an old blacksmith and tannery, this residence offers an unparalleled blend of architectural integrity and storied past. As a superb example of colonial architecture, the home retains its traditional "4 over 4" floor plan, featuring four grand, sun-drenched rooms on the first level and four generous bedrooms above, all connected by an elegant central hallway. Step inside and experience the character of historic construction. Watch the light truly dance through the mesmerizing antique crown-glass window panes. The interiors are adorned with exquisite original details, including wide-plank chestnut flooring in the primary suite, built-in closets, and five stately fireplaces that serve as captivating focal points throughout the main rooms.

11 W Chestnut Hill Rd, Litchfield
$708,000
4 Beds ⋅ 3 Baths ⋅ 24154338 MLS
Highest & Best Deadline Tuesday 3/3 at 6pm!!! Nestled on over 8 private acres in the heart of Historic Litchfield, this beautifully maintained 4bed, 2.5bath home offers the perfect blend of classic New England charm and modern comfort. Built in 2008, the 3,100 sqft residence welcomes you into a vaulted foyer drenched in natural light, flowing seamlessly into a spacious kitchen designed for entertaining. Off of the kitchen is your great room offering vaulted ceilings and back deck access. The main floor offers high end finishes, tasteful crown molding, chair rail, and wainscoting throughout. Upstairs, the primary suite and additional bedrooms provide peaceful views of rolling lawns, mature trees, and the ultimate privacy. Step outside and enjoy your own private sanctuary. Outdoor spaces invite entertaining, gardening, or quiet mornings sipping coffee while taking in the tranquility of your surroundings. The landscaped mature trees create a sense of complete privacy while being just minutes from the Litchfield Green, boutique shops, dining, hiking trails, and local attractions. With a 2 car garage, ample storage, and thoughtful design throughout, this home perfectly balances everyday functionality with timeless style. Whether hosting gatherings, enjoying the outdoors, or relaxing in comfort, 3 Sally Burr Road offers a rare opportunity to live the quintessential Connecticut lifestyle, private, spacious, and full of charm. A home ready to welcome its next chapter

3 Sally Burr Rd, Litchfield
$660,000
3 Beds ⋅ 3 Baths ⋅ 24114744 MLS
A very special custom built Nine room Country Colonial with unlimited possibilities & an ideal home for entertaining large parties. There's an extremely functional & flexible floor plan, generous sized rooms, & a large 26' X 19' kitchen with two pantries, a wood stove, access to the deck, an enclosed porch, & a full bath! There are 3,514 square feet on the first, second, & third levels, & the extensive use of wood makes the home very charming. The original home is the Ranch portion that was built in 1961, & the large Colonial portion was added in 2009! Located at the end of Buell Road, a low traffic street, on a 4.1 acre wooded homesite, with five out-buildings including a chicken coop, a goat barn, and a woodshed! The Organic fruit trees are currently blooming and will be providing fruit soon and the peach trees are already! You will feel like you are stepping into a nature lovers paradise, & there is the benefit of privacy too. The second & third floors have four generous sized rooms each with a closet, & currently being used as bedrooms. There are three full baths, one on each floor! There's unlimited possibilities, and lots of storage space. There are many upgrades by the current owners, and a first-floor laundry, central air conditioning, two wells, septic, and a two-car garage with automatic openers. New furnace & hot water heater Aug. 2025. Must be seen to be appreciated! It can be used as a year round home or a country get away from the hustle and bustle of the City

284 Buell Rd, Litchfield
$654,000
4 Beds ⋅ 3 Baths ⋅ 24123522 MLS
Discover your own private sanctuary on this stunning 7.33 acre wooded residence where tranquility meets elegance on a peaceful country road. This beautifully updated four-bedroom Colonial seamlessly blends classic charm with modern conveniences throughout. The heart of the home features an expertly updated kitchen showcasing elegant quartz countertops, a functional center island and an inviting dining area that flows effortlessly to the expansive wood deck-perfect for entertaining against the backdrop of mature trees and natural beauty. The welcoming family room boasts rich hardwood flooring and a cozy wood-burning fireplace, while the formal living room impresses with refined dental molding and plush wall to wall carpeting. Entertaining is effortless in the sun-filled formal dining room, enhanced by gleaming hardwood floors and elegant dental molding. Practicality continues with a spacious mudroom offering abundant storage and seamless access to the oversized two-car garage, plus a convenient main-level powder room. The upper level reveals an expansive primary bedroom suite featuring two generous closets plus a charming cedar closet, comfortable wall to wall carpeting and a versatile bonus room ideal for a home office, exercise space or personal retreat. Three additional spacious guest rooms and a full bathroom complete this level.

143 Goodhouse Rd, Litchfield
$650,000
3 Beds ⋅ 2 Baths ⋅ 24159904 MLS
Escape the hustle and bustle of city life and uncover your perfect sanctuary at 29 Milton Rd, a beautifully remodeled custom multi level home in charming Litchfield, CT. Ideal for those looking to downsize or anyone seeking a peaceful retreat, this 3-bedroom, 2-bathroom home seamlessly blends modern luxury with a tranquil natural setting. Situated just a short distance from The Litchfield Green, you will enjoy delightful shopping, fantastic dining options, and the quintessential charm of New England right at your doorstep. Thoughtfully integrated into its landscape, 29 Milton Rd provides an inviting space perfect for both relaxation and entertainment. The lower level, which is not included in the square footage listed in property records, boasts a private office, laundry room, half bath, and a versatile open flex space-ideal for a home gym or recreation room. Lovingly remodeled by its owners over the past four years, this home features an architect-designed open floor plan, brand-new mechanical systems, central air conditioning and heating, a new engineered septic system, an advanced water filtration system, a gourmet kitchen, and new roofing and siding. Step outside to enjoy your morning coffee or evening cocktails on the sprawling deck, while listening to the babbling Moulthrop Brook, which offers amazing, snow-covered winter scenery. Host summer BBQs on the stone patio, or explore nearby White Memorial Conservation Center, which serves as your backyard canvas.

29 Milton Rd, Litchfield
$640,000
2 Beds ⋅ 2 Baths ⋅ 24079472 MLS
Delight in this fully renovated, 2,080 sq. foot, 2-3 bedroom ranch with a mid-century modern vibe, centrally located on 3.11 acres with stunning, far reaching views in a peaceful setting of mature trees , open meadows, and vistas ideal for horseback riding and gentlemen farming. The location is convenient to the Litchfield Green and amenities offered by this highly sought after destination. Features include: Solar energy that provides the power for your electric vehicle and all all electric needs, barn with four stalls, chicken coup and paddock (bring your sheep, cows, llamas), two fireplaces, central air, meandering stream, private patio and covered porch, 2 car attached garage, cathedral ceilings and a pool site.The primary suite has a dressing room and custom closet features. The light filled lower level with second bedroom suite, laundry room and family room has access to the attached garage making for an easy transformation to an in law apartment. A must see for value and quality of life.

73 Mcbride Rd, Litchfield
$638,000
3 Beds ⋅ 2 Baths ⋅ 24110318 MLS
Welcome to Milton Meadow. This classic center hall colonial is nestled in a sought-after country setting on nearly three acres of meticulously landscaped grounds. This recently renovated three bedroom home offers a harmonious blend of classic charm and modern living. As you step inside, the main floor unfolds into an expansive living room, complete with a cozy wood-burning fireplace, perfect for New England evenings. The adjacent dining room invites memorable gatherings, while the kitchen, featuring a convenient walk-out, serves as a gateway to outdoor deck and patio, with the security of a fenced yard. Upstairs, the large primary suite becomes a private retreat, boasting built-in storage, a comfortable area for seating, and its own fireplace, creating a sanctuary for relaxation. Two additional bedrooms on the upper level offer ample space for family or guests. The residence is surrounded by lush gardens and a private fenced backyard shielded by mature arborvitae hedging and abundant ferns. The location offers the convenience of proximity to the charming shops, parks, and restaurants of both historic Bantam and Litchfield.

318 Milton Rd, Litchfield
$635,000
3 Beds ⋅ 3 Baths ⋅ 24181907 MLS
Final touches of a gorgeous renovation complete this 3 bedroom and 2 1/2 bath Colonial in Litchfield, less than 1 mile to The Green. This 1914 home with a wide open floorplan and lots of natural light is loaded with character, and ready for it's new owner to move right in. The process started with stripping the walls to the studs, new wiring & plumbing, new warm air & central AC, new kitchen with Bosch appliances and bathrooms, replaced old flooring on both levels with white oak floors, new bluestone patio with a stone wall, painted inside & out, and more! The color palate is stunning, and the added wooden barn beams compliment the chic look. Outdoors enjoy the wrap around deck in front, or the recently added bluestone patio with a stone wall in the back. There's even a newly paved driveway! Savor a dinner at an award winning restaurant in town, or a glass of wine at the Abner's rooftop bar. Many take a hike on the great choices of trails throughout the area, and residents of Litchfield may use the Litchfield Town Beach at Bantam Lake. Only 2 hours to NYC and 2 1/2 hours to Boston.

350 South St, Litchfield
$610,000
3 Beds ⋅ 4 Baths ⋅ 24169253 MLS ⋅ Hunter's Chase Of Litchfield BLDG.
Tucked within 77 pristine country acres in the heart of Litchfield, Hunter's Chase is among the Northwest Hills' most sought-after private communities. This impeccably maintained residence delivers refined craftsmanship and timeless design throughout. The chef's kitchen features marble countertops, a professional gas range, premium refrigeration, and an island with seating at the end and rear cabinetry for additional storage - perfect for both casual living and elegant entertaining. The open floor plan flows through the dining and living areas, anchored by a marble-accented gas log fireplace. A private composite deck overlooks protected conservation land, offering serene natural views year-round. The primary suite offers a spacious walk-in closet and sitting area, en suite full bath with jacuzzi tub. Two additional guest bedrooms, a full bath, and laundry complete the upper level. The finished lower level boasts 10-foot ceilings, flexible living space, a bath, and sliding doors to a private patio. Community amenities include a heated pool, sports court, and a clubhouse with fitness center, locker rooms, and a gathering space with fireplace, bar, and kitchen. Minutes to the Historic Litchfield Green with celebrated restaurants and shops.

302 Hunter Dr Unit 302, Litchfield
$610,000
4 Beds ⋅ 2 Baths ⋅ 24164952 MLS
Timeless craftsmanship meets modern elegance. This home is the perfect blend of historic integrity and contemporary luxury in this 1952 Cape, masterfully constructed by the renowned George Switzer. This Switzer-built original has been thoughtfully updated and a second floor was added in 2005 to meet the needs of today's lifestyle while preserving its "adorable" mid-century soul. The main floor has five rooms; a light-filled Living Room with fireplace, generously sized Dining Room perfect for intimate week-night dinners to festive holiday gatherings, a kitchen that has been beautifully restored for the "chef" in you and two spacious bedrooms, one with laundry and a hallway full bath that offer the convenience of single-level living. The second floor expands the home's footprint with a layout designed for work, rest and play. There are two bright and airy bedrooms a full hallway bath with double vanity, study loft and dedicated play area for creativity and fun. Set on 1.05 well-landscaped acres, the property offers a sense of privacy and space. Whether you're headed to the town pickleball/tennis courts , local playground or the community fields, everything you need is just moments away. This home is a turnkey opportunity to own a piece of local history with all the comforts. Close to the center of Litchfield's shopping, boutique hotels & dining. Visit White Memorial Conservation, Bantam Lake, Topsmead State Forest, enjoy horseback riding, skiing, hiking and more. 2+-hrs. to NYC

11 Sheldon Ln, Litchfield
$608,000
2 Beds ⋅ 2 Baths ⋅ 24196443 MLS
This turnkey 2-bedroom, 2-bathroom home sits on a level lot along one of Litchfield's most desirable roads. The home offers a well-designed floor plan with beautiful craftsmanship throughout. The side entry opens to a welcoming mudroom with access to the kitchen, complete with granite countertops and abundant storage. The kitchen flows into the dining area and cozy living room, where a gas log fireplace, beautiful built-ins, and a centrally located full bathroom highlight the space. Adjacent is the guest bedroom, which includes two large closets and direct access to one of the home's most unique features: a 15' x 13' atrium, providing wonderful indoor-outdoor living space to enjoy year-round. At the opposite end of the home, a 2007 addition houses the primary bedroom suite. The spacious bedroom offers vaulted ceilings, a full bathroom with both a shower and bathtub, and a large walk-in closet with a washer and dryer. On the lower level is a finished room ideal for use as an office or studio. The beautifully landscaped grounds are highlighted by an in-ground pool and a 24' x 12' poolside outbuilding. Conveniently located just minutes from local favorites including Arethusa Farm's famous ice cream, Bantam Lake, Mt. Tom State Park, White Memorial Conservation Center, charming shops, and award-winning restaurants. Approximately two hours from Manhattan, this stunning property is equally suited for a country retreat or year-round living.

336 Maple St, Litchfield

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