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28 Lake Dr, New Milford
$1,499,000
4 Beds ⋅ 3 Baths ⋅ 24193954 MLS
Waterfront Candlewood Lake living, elevated. This exceptional retreat at 28 Lake Drive commands roughly 50 feet of coveted direct lake frontage, complete with a private sandy beach and dock- a rare offering on one of Connecticut's premier lakes. A dramatic stone fireplace rises beneath soaring vaulted ceilings and hand-hewn beams, anchoring a living room bathed in natural light, while the adjoining dining room frames uninterrupted water views through a wall of windows. The eat-in kitchen flows effortlessly to a main-level deck, made for entertaining against a backdrop of lake and treetops. Upstairs, the primary suite feels like a private sanctuary, with its own balcony overlooking the water and a spa-caliber bath featuring a freestanding soaking tub, glass-enclosed shower, and dual vanity set beneath an octagon window framed on the lake. A walk-up attic offers refined extra space, while the finished lower level, appointed with its own full bath, opens to a stone patio designed for lakeside gatherings. Set on 0.13 acres within the desirable Candlewood Trails community, this 2,336-square-foot residence, built in 1935, pairs timeless craftsmanship with an unmatched waterfront lifestyle. Marinas, boat launches, and New Milford's finest dining are just minutes away. A true direct-waterfront property with a private beach on Candlewood Lake rarely comes to market - don't miss the opportunity to make it yours.

28 Lake Dr, New Milford

168 Fern Ave, Litchfield
$1,499,000
4 Beds ⋅ 4 Baths ⋅ 24166479 MLS
Welcome to Fern House at 168 Fern Avenue-an extraordinary private country estate set on 3.71 picturesque acres in one of Litchfield's most coveted enclaves. Perfectly tucked behind mature landscaping and approached by a graceful circular drive, this quintessential New England retreat offers the rare combination of luxury living, equestrian amenities, and resort-style outdoor spaces just moments from the storybook charm of downtown Litchfield. Spanning more than 3,600 square feet, this expansive contemporary residence is filled with natural light, soaring ceilings, and oversized windows that frame lush views in every direction. A dramatic double-height foyer opens to an airy, open-concept main living area anchored by a stunning floor-to-ceiling fireplace-creating both warmth and architectural impact. Designed for elevated everyday living and effortless entertaining, the chef's kitchen is beautifully appointed with premium appliances including double KitchenAid wall ovens, a five-burner cooktop, dishwasher, pantry, and dedicated office nook, all flowing seamlessly into gracious gathering spaces and a formal dining room. The flexible and thoughtfully designed floor plan offers four bedrooms and three-and-a-half baths, including a desirable first-floor primary suite option.

168 Fern Ave, Litchfield

197 Skyline Ridge Rd, Bridgewater
$1,495,000
4 Beds ⋅ 4 Baths ⋅ 24067675 MLS
Rarely available. 1880 antique gem on 10 acres, with a first level primary bedroom and bath, situated on one of Bridgewater's most prestigious and quiet roads, offering a private setting. This residence masterfully blends historic character with an airy, open floor plan where the kitchen flows seamlessly into a spacious great room and a formal living room anchored by a classic fireplace. The interior living space consists of a main floor primary bedroom and bath, second level with 2 bedrooms and shared bath and a third level bedroom with it's own bath. The spaces transition beautifully to a 24 x 18 screened porch with slate flooring, opening onto a bluestone terrace. Perfect for entertaining, the terrace overlooks the pool and captures western exposures. The property is further enhanced by a two-story barn, providing ample space for storage or workshop. This is a unique opportunity to own a quintessential New England retreat in a premier location.

197 Skyline Ridge Rd, Bridgewater

28 Sunny Ridge Rd, Washington
$1,495,000
6 Beds ⋅ 5 Baths ⋅ 24137365 MLS
Historic home with untapped potential in Washington. Set on 4 serene acres in the Sunny Ridge Historic District, this 1846 Colonial contains elements of the original house which was built in 1768 on the same location. With approximately 4,200 square feet of living space, the home's six bedrooms and three full, two half baths provide a flexible layout ready for a thoughtful renovation. The proportions of the rooms reflect the era - cozy in scale yet filled with authentic detail: original wood floors, period moldings and working fireplaces that speak to nearly two centuries of character. A large eat- in kitchen and extended screened porch add to its charm. Outside, the 3.8 acre parcel balances privacy and manageability. Surrounded by mature trees and open lawn, there is ample space for gardens, patios, or potentially a pool. Four outbuildings can be used as garages, sheds or possibly a pool house. The location on Sunny Ridge Road, with its historical significance and easy proximity to the Depot's shops, dining and cultural amenities, makes the setting especially desirable. This is an opportunity to write the next chapter of a Washington landmark. Exact property acreage is subject to completion of new survey and lot line revision.

28 Sunny Ridge Rd, Washington

55 Mount Tom Passway, Morris
$1,450,000
4 Beds ⋅ 5 Baths ⋅ 24213310 MLS
Experience Litchfield County from this custom-built modern Craftsman in Morris, set on three private acres along quiet Mount Tom Passway overlooking Mount Tom Pond. Built in 2009, the approximately 3,300-square-foot home offers a rare blend of privacy, open space, and luxury, with conservation land directly across the road and seasonal pond views that deepen the connection to its natural surroundings. Thoughtfully positioned to maximize natural light, the first floor features south-facing living spaces and a westerly orientation that captures sunsets. An open-concept kitchen with walk-in pantry flows into dining and living areas, complemented by a half bath and solarium-ideal for everyday living and entertaining. Maple floors, doors, and cabinetry add warmth throughout, paired with granite countertops and cedar siding. The second floor includes four bedrooms, each with a private bath, along with an office and laundry room. The inviting primary suite features floor-to-ceiling windows, two walk-in closets, and a spa-like bath with dual sinks, a soaking tub, steam shower, sauna, and private water closet- The walkout basement offers exceptional potential for additional living, recreation, or workspace, with nine-foot ceilings, a separate HVAC zone, garage access, and partial finishing in place. A whole-house Kubota generator with a dedicated diesel tank adds year-round peace of mind. Unfinished attic space provides even greater flexibility for future expansion.

55 Mount Tom Passway, Morris

39 Gorham Rd, Kent
$1,435,000
4 Beds ⋅ 3 Baths ⋅ 24196681 MLS
Experience the ease of single-level living in this Hobie award-winning custom home in St. John's Peak - where luxury homes are beautifully set in the hills of Kent, CT. This modern farmhouse built in 2022 offers the perfect balance of sophisticated design and low-maintenance functionality on over five private acres. An open floor plan with 9' ceilings and oversized windows is bathed in natural light and anchored by 8" white oak hardwood floors throughout that allow for a seamless flow between the dramatic living area with its floor-to-ceiling fireplace-and a stunning custom kitchen with Thermador appliances overlooking an expansive dining space. The primary suite serves as a private retreat on one wing of the home, while a dedicated guest wing with two additional bedrooms and a full bath provides flexibility for hosting visitors. With a 4-bedroom septic, a flex room on the main level can be utilized as an additional guest bedroom, private office, den, gym, or studio. An additional 2,714 sq ft of unfinished space on the lower level provides room to expand or store more than you can imagine.

39 Gorham Rd, Kent

108 Squire Hill Rd, New Milford
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 24203561 MLS
Stunningly renovated 1806 federal colonial estate house in Upper Merryall graciously sited on 1.88 acres of level land. Classic New England Antique exuding elegance, craftsmanship and prominence. Basement to attic restoration in 2020 restored the original wide plank chestnut floors, exposed hand-hewn chestnut beams, 9' ceilings, 6 fireplaces and classic trim back to their 220 year glory. Restoration preserved the antiquity and also allowed for new touches: a modern country kitchen with top appliances; central AC; pampering bathrooms; wine cooler and other of today's amenities. The slate floored sunroom with oversized windows offers both sunlight and views. The formal dining room with exposed beams and fireplace has French doors to the stone terrace. There are two living room parlors both boasting fireplaces and new lighting. The status of the family that built this home is apparent as the exquisite trim work is carried throughout the residence also details each of the three large bedrooms on the second level. There is a whimsical game room with a wet bar at the back of the second floor that conveniently has back stairs to the kitchen. All three full bathrooms are sumptuous with the primary bath situated off the dressing room. More details that one can count here with built in bookshelves, wine cave, huge fire pit, antique windows, locks and hinges.

108 Squire Hill Rd, New Milford

12 W Mountain Rd, Sharon
$1,399,000
5 Beds ⋅ 4 Baths ⋅ 24198204 MLS
COUNTRY HOME Nestled in the foothills ...Within short distance to NYC, Boston, and the beautiful eastern shores of Connecticut sits a quiet, well maintained retreat in Litchfield County for family, friends, guests, or the solitary traveler. Abutting a private land preserve and enclosed on 5.5 woodland acres off a private road sits this lovely country home. Thoughtfully Equipped with chefs kitchen opening to family room with wood burning stove and enclosed sun porch ..there to relax. All rooms overlook large expanse of the gently wooded yard, showcasing mature trees and planted gardens ... the views from every room of the house offer quiet and breathtaking seasonal pleasures. Master bedroom and guest room are both located on the main level. Upstairs discover 4 rooms with built-in bookshelves, full closets, full bath and a separate sitting room, Above the two car garage is separate bonus room for exercise, private office or artistic exploration. All of this is not exaggerated... The residence was designed and built by a well respected local developer as a timeless country masterpiece offering all conveniences of easy living and low maintenance...with easy proximity to Sharon, Amenia, Kent, Millerton and surrounding areas. Priced well and within reach.

12 W Mountain Rd, Sharon

14 Gate Post Ln, Litchfield
$1,397,500
4 Beds ⋅ 5 Baths ⋅ 24193748 MLS
This new construction home is perfectly sited on 10+ private acres located on the border of Litchfield and Washington. It abuts 70 acres of open space land with access to the Shepaug River, and is located within a few minutes drive of the villages of Bantam, New Preston, Washington, and private schools in the area. With 4 bedrooms and 4 1/2 bathrooms, this home has an open floor plan with many windows and tall ceilings for light-filled, airy spaces. Coming in from the attached garage you enter a large mudroom with 1/2 bath, built in bench, and plentiful storage. The custom kitchen with high end appliances features a breakfast bar, dining area, and opens up to a large deck. The family room is bathed in sunlight by windows facing south and west and features a built-in bookcase and a fireplace. There is a private office off the entry foyer. The second floor includes 4 en-suite bedrooms, a loft area, and laundry room. The primary bedroom suite includes an all-marble bath with oversized shower and a generous walk-in closet. The full, unfinished basement is a walkout with lots of windows and access to the backyard. The property is professionally landscaped with brick walkways to the front porch and rear deck. The backyard has ample space for a pool site . Agent/Owner

14 Gate Post Ln, Litchfield

14 Flanders Ln, Kent
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 24184750 MLS
First time ever on the market: this custom Contemporary abuts hundreds of acres of conserved land owned by the State of Connecticut, offering sweeping pastoral views and exceptional privacy less than five minutes from Kent Village Center. Inside the ~2,800 sq ft main house, an open floor plan blends with sophisticated country character. The main level kitchen is light-filled with breakfast bar seating, opening to a sitting area that flows into a sunroom and out to a bluestone patio framing the view. A formal dining room with vaulted ceiling opens to the living room, anchored by a fireplace. A main level bedroom with private bath completes this floor. Upstairs, the primary suite features a vaulted ceiling opening onto a sleeping porch, with a private bath of its own. Two more bedrooms share a full bath on this level. The home was also expanded to include an ~800 sq ft separate guest apartment, currently used as an expansive home office. This area would make a wonderful guest space, with the two existing offices easily converted into two additional bedrooms. The space already includes a living room, dining area, kitchenette, and full bath. The lower level of the main house has been finished to include a media room and laundry, and the original two-car garage is now finished storage space, easily converted back if needed. A rare find in a sought-after location, just two hours from NYC.

14 Flanders Ln, Kent

30 Hollow Rd, Woodbury
$1,395,000
5 Beds ⋅ 5 Baths ⋅ 24168618 MLS
Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury

33 Sentry Hill Rd, Roxbury
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 24163570 MLS
Mint/Move-in Condition! Private c. 2002 Colonial Clapboard 4+ bedroom home on a scenic dirt road along the Shepaug River and just down the road from Land Trust with trails. Heated Gunite Pool surrounded by endless summer hydrangea and 3 acres of level lawn bordered by the Moosehorn Brook. Magnificent design, 4 wood-burning fireplaces, beautiful wide-board softwood floors, over-sized living room, spacious dining room and chef's kitchen with striking polished hardwood center island. Upstairs, Primary En Suite Bedroom with lovely clawfoot tub, double sinks, large separate shower and spacious dressing room. Two more bedrooms share a charming hall bath. Finished lower level currently outfitted as a family room with French doors to a serene patio leading out to the pool, another en suite bedroom and two more finished flexible spaces. (Makes the total finished sq feet: 3676!)The perfect peaceful location, minutes from the centers of Roxbury and Washington. Must see!

33 Sentry Hill Rd, Roxbury

Candlewood Mountain Road, New Milford
$1,390,000
24137997 MLS
Nestled in the serene landscape of New Milford, CT, past horse farms and fields, this special property on Mountain Drive presents a once-in-a-lifetime opportunity to own a piece of local history. Offered for the first time since its original ownership (back before the lake existed), this three-acre estate is a testament to refined countryside living. The level lot, adorned with a charming barn, invites you to design and build your dream home amidst nature's embrace. Complementing this vast expanse is a coveted 0.28-acre waterfront parcel that boasts a private beach, a personal dock, and breathtaking water views. Imagine mornings spent basking in tranquil waters and evenings enjoying the sunlight glistening off the lake, right from your own backyard. This property, rich with history and potential, offers a unique canvas for crafting a bespoke lifestyle, combining elegance and comfort with unparalleled water access. Seize this opportunity to create a legacy estate, perfectly situated to enjoy both the peace of the countryside and the allure of lakeside living. Taxes on the barn are: $5,606.00 Taxes on the waterfront portion are: $3,179.00

Candlewood Mountain Road, New Milford

11 Gaffney Rd, New Milford
$1,375,000
4 Beds ⋅ 4 Baths ⋅ 24202206 MLS
This is a rare Litchfield County country property offering 8.32 private acres, Gunite pool, pond, meadow, oversized four-car garage, separate workshop and exceptional outdoor living-all surrounding a distinctive four-bedroom contemporary residence extensively improved by its current owners. Designed to connect with its beautiful setting, the light-filled home features a dramatic vaulted living room with floor-to-ceiling stone fireplace and direct access to the pool and outdoor spaces. The modern kitchen opens to a pergola-covered dining patio, while west-facing decks on multiple levels overlook the surrounding grounds. A light-filled first-floor primary-suite addition creates a private retreat with skylights, a wall of windows, vaulted ceiling, walk-in closet, luxurious bath and private deck overlooking your private meadow. Upper levels provide additional bedrooms, baths, another fireplace and private west-facing decks. Outside is where 11 Gaffney becomes truly distinctive. The 8+ acre property combines a Gunite pool, pond, meadow, mature landscaping, extensive patios and decks, oversized four-car detached garage, separate 15'x9' workshop building, 8x4' attached garden shed and additional storage, one car garage and mechanical room below the primary suite.

11 Gaffney Rd, New Milford

Chestnut Land Road, New Milford
$1,300,000
24170226 MLS
An exceptional offering awaits with this beautiful 61.54-acre parcel ideally positioned in a prime New Milford location, bordering the charming village of Washington Depot. This property is designated prime agricultural land, while also offering exceptional potential for a variety of future uses, including subdivision, a vineyard, equestrian estate, or private country retreat, solar farm. Featuring sweeping views with substantial level, usable land, the setting provides a beautiful and versatile landscape with endless possibilities. Originally subdivided in 1990 for 26 lots, any future subdivision would require new approvals, offering the opportunity to reimagine the property to today's standards. Enjoy the best of Litchfield County living with close proximity to downtown New Milford, as well as the scenic beauty of Lake Waramaug and surrounding towns. Maps and additional information available. A rare opportunity to bring your vision to life. Close to schools, shopping, dining, commuting with the ambience of New Milford and surrounding charming town of Washington Depot.

Chestnut Land Road, New Milford

11 Evergreen Dr, Roxbury
$1,300,000
4 Beds ⋅ 4 Baths ⋅ 24154135 MLS
This is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a classic farmhouse design Cape with a covered front porch with metal roof. The ceiling height on the main level 9'and 8' on the upper level. Both levels have wood floors. The primary suite is on the main level with a large bath including a shower a free standing tub and a walk in closet. The kitchen is open to the family room which has a bank of 3 sets of sliders to the back deck area and a fireplace on the end wall. The main level includes a formal dining room, formal living room and a main level laundry/mud room. The upper level includes 3 additional bedrooms and 2 full baths. There is a study area as well as a rec room over the garage. The large 2 car garage will have an electric car charger. Roxbury is a lovely small town with bucolic farms and farmers markets. It is very sought after for weekend and summer homes. There are many land trust areas for hiking and exploring. The Shepard river is great for fishing and tubing. Litchfield County has many lakes for out door recreation. There are ski areas close by and lots of summer fairs. The area is known for art galleries, antique shops and great restaurants. Taxes TBD

11 Evergreen Dr, Roxbury

73 Dublin Rd, Canaan
$1,295,000
3 Beds ⋅ 2 Baths ⋅ 24203845 MLS
Tucked away on five private, professionally landscaped acres, this reimagined charcoal A-frame blends dramatic architectural style with refined modern living. Completely transformed from top to bottom, the residence features crisp new windows that flood the open interior with natural light, brand-new flooring throughout, and a brand-new kitchen designed for effortless comfort. The home's open layout flows seamlessly onto an expansive deck, perfect for outdoor dining or taking in the peaceful, scenic outdoors. Practical amenities abound with a spacious circle driveway for ample guest parking, plus a massive 1,200+ square foot detached 3-car garage with dedicated shop space-ideal for creators, hobbyists, or extra storage. Just two minutes from historic Falls Village-one of Connecticut's most charming small towns-offering cozy local eateries, immediate access to the Appalachian Trail, and the natural beauty of Great Falls. All the while, less than 30 minutes from Metro North train station!

73 Dublin Rd, Canaan

77 Judds Bridge Rd, Roxbury
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 24193455 MLS
A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry cabinetry, double oven, cook top, peninsula with seating, pantry, powder and laundry room, and a spacious den with vaulted ceilings, antique beams and centered around a soaring Rumford fireplace. The primary suite features a tray ceiling, en-suite bath with double sink, generous walk-in closet, while three additional bedrooms share a full bath. Out the French doors onto Ipe deck provides a refined setting for outdoor living and your private back yard. Additional highlights include a three-car garage, an unfinished bonus room over the garage that offers excellent expansion potential, new UV paned deck doors, updated mechanicals, architectural roof shingles, and a portable generator. Quintessential New England living at it's best!

77 Judds Bridge Rd, Roxbury

105 & 109 Us-7, Salisbury
$1,295,000
1 Baths ⋅ 24133160 MLS
Discover a rare opportunity in the heart of Salisbury with this exceptional mixed-use property at 105 & 109 Route 7, offering a perfect blend of commercial versatility and residential comfort. Set on a level one-acre lot, the property features a 2,583 square-foot five-bay automotive garage currently operating as a licensed car dealership and auto repair facility, along with a charming 1,270 square-foot three-bedroom home. Once a full-service gas station in the 1950s, the site remains approved and zoned for fuel service and also allows for restaurant, drive-thru coffee, and various other commercial or mixed-use opportunities. Engineering and architectural plans for proposed future uses are available upon request, making it even easier to bring your vision to life. With excellent visibility along Route 7, low annual taxes, and clean 2019 DEEP environmental testing, this property offers both peace of mind and incredible potential. Located just one mile from Lime Rock Park and two blocks from the regional high school, it benefits from steady local and seasonal traffic alike. Whether you envision expanding the existing business, reintroducing a gas station or cafe, or creating a new destination entirely, 105 & 109 Route 7 presents a unique chance to invest, create, and thrive in one of Litchfield County's most scenic corridors.

105 & 109 Us-7, Salisbury

509 Weekeepeemee Rd, Woodbury
$1,278,000
3 Beds ⋅ 3 Baths ⋅ 24192284 MLS
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

2540 Norfolk Rd, Torrington
$1,278,000
1 Beds ⋅ 4 Baths ⋅ 24175012 MLS
This one-of-a-kind custom designed home is a peaceful sanctuary, situated on top of a hill on 18 secluded acres (that is subdividable) and bordered by conservation land. To access the home, you drive over a bridge and up a paved and gravel driveway. The home is fine for entertaining, featuring a cook's kitchen with stainless steel appliances, a breakfast bar and granite leather suede countertops. The expansive dining area includes a gas fireplace, and the living room boasts a soaring ceiling and a wood burning fireplace. A large deck provides amazing views, and you can enjoy swimming all year round with the indoor 18x36 inground saltwater pool, complete with a dehumidifying system and alarm. The main level is completed by a laundry room, mud room and attached two-car garage. For a retreat, the primary bedroom suite offers a sitting room with custom crafted Mahogany doors and ceiling fan, with a luxurious primary bath featuring a soaking tub, tile shower and dual sinks. The lower level includes a possible in-law, wine cellar, a full bath, a tandem 2-car garage and a patio. An elevator which serves all 3 levels of the home. Mechanical features of the property include energy efficient geothermal heat and air conditioning, a generator and underground utilities. The grounds are thoughtfully cultivated featuring fruit trees, blueberry and raspberry bushes, fenced in gardens, a stone walkway and the paved driveway. A beautiful place to reside in the Litchfield Hills

2540 Norfolk Rd, Torrington

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