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Cheshire Homes for Sale

Newest Gaylordsville, CT Homes For Sale

589 Kent Rd, New Milford
$299,900
2 Beds ⋅ 2 Baths ⋅ 24215379 MLS
Tucked away on .28 acres with seasonal views of the Housatonic River, this eclectic 1920 cottage is full of character and potential. Featuring 2 bedrooms, hardwood floors, central air, and a cozy woodstove, the home offers a unique opportunity for buyers looking to restore and personalize a property with charm. The detached artist studio provides the perfect space for creative pursuits, while an additional detached shed offers extra storage. In need of updating and repairs, this one-of-a-kind property is ideal for those with vision who appreciate distinctive homes, a peaceful setting, and the chance to create something special.

589 Kent Rd, New Milford
656 Kent Rd, New Milford
$599,900
3 Beds ⋅ 2 Baths ⋅ 24210382 MLS
This unique and versatile property offers more than meets the eye! The main home features an inviting and distinctive floor plan highlighted by a spacious living room with vaulted ceilings, exposed character, and a stunning stone fireplace that serves as the focal point of the space. The main level also includes an eat-in kitchen, formal dining room, home office, two bedrooms, and a full bath, providing flexible living options. The upper level is dedicated to the primary suite, featuring a full bath, a bright sunroom, and sliders leading to a private deck overlooking the property. Adding exceptional value is the extensive detached outbuilding, offering garage space and potential for an in-law suite, studio, or workshop. Whether you're seeking multi-generational living, hobby space, vehicle storage, or room to grow, this impressive structure provides endless possibilities. Set on a picturesque property with ample outdoor space, this one-of-a-kind offering combines character, flexibility, and opportunity.

656 Kent Rd, New Milford
12 Loormann Ln, New Milford
$795,000
3 Beds ⋅ 3 Baths ⋅ 24210145 MLS
Tranquil Contemporary Colonial Retreat in Northern New Milford. Tucked away on a quiet private lane in the picturesque northern rural section of New Milford, this beautifully crafted contemporary colonial offers an exquisite blend of privacy, thoughtful design, and everyday convenience. Despite its secluded, countryside feel, the property provides incredibly easy access to the train, making it an ideal haven for commuters and weekenders alike. The home features three spacious bedrooms and two-and-a-half baths, office, lower level game room, providing ample room for comfortable living and entertaining. Outdoor living is elevated to an art form here, a charming covered porch and patio complete with a relaxing hot tub offer the perfect settings for morning coffee or evening gatherings. The property is enveloped by master gardener-designed grounds, beautifully framed by classic New England stone walls. Adding immense value and lifestyle versatility to the estate is a two stall barn. The barn's second level features a convenient walk-out directly to the upper yard, creating a sunlit, inspiring canvas that is perfectly suited for an art studio, craftsman's workshop, or a private yoga sanctuary. Easement with right of way over Loormann Lane. A/C on second floor, Electric and oil hot water baseboard heat.

12 Loormann Ln, New Milford
34 Gaylord Rd, New Milford
$303,050
3 Beds ⋅ 2 Baths ⋅ 24210566 MLS
Opportunity awaits with this authentic 1700s Colonial located in the picturesque Gaylordsville section of New Milford. Offering over 1,800 square feet with three bedrooms and two full baths, this historic home is ready for its next chapter. In need of renovation and updating throughout, the property provides a unique opportunity to restore a classic New England home while preserving its original character and charm. A large two-car garage offers substantial additional space above, providing even more flexibility and potential. With a generous footprint, traditional Colonial architecture, and plenty of room to reimagine, this is an ideal project for a buyer looking to bring their vision to life. A true fixer-upper with history, character, and tremendous potential.

34 Gaylord Rd, New Milford
10 Strid Ln, New Milford
$525,000
3 Beds ⋅ 3 Baths ⋅ 24204122 MLS
Peace, privacy, & classic New England charm! This beautifully maintained Colonial sits on over three acres of private, wooded land in a serene, park-like setting at the end of a forest-lined road. The main level features a spacious family room with cathedral ceilings, exposed wood beams, hardwood flooring, & a brick fireplace with a raised hearth & mantel. Dark accent walls & modern lighting add character, while large windows bring in natural light & peaceful views. The renovated open-concept kitchen, dining, & family room area creates easy flow for everyday living & entertaining, with a lovely bay window view. Updated bathrooms, a main-level laundry room, & half bath add convenience. Upstairs, the primary bedroom offers a private en-suite with a large shower & walk-in closet. Two additional bedrooms share a full bathroom-great for family, guests, or a home office. Outdoors, a three-season screened porch offers a peaceful retreat, & the deck extends living space for grilling, dining, & entertaining amid the private, wooded surroundings. The 1,104 sq ft unfinished basement includes a partially finished area with a wood stove-ideal for recreation, a home office, gym, or extra gathering space-plus direct access to the attached two-car garage for parking & storage. Recent updates: 2024 two-zone ducted heat pump HVAC (heating & cooling), 2024 family room renovation, 2026 duct drop & closet renovation, fresh interior paint (2026), & new gutter guards (2026).

10 Strid Ln, New Milford
2 Pilgrims Way, New Milford
$599,950
4 Beds ⋅ 3 Baths ⋅ 24203705 MLS
A RARE COMBINATION OF NEW ENGLAND CHARM AND MODERN LUXURY-MAKE AN OFFER TODAY! Welcome to 2 Pilgrims Way, a beautifully refreshed and meticulously updated 4-bedroom, 2.5-bath Colonial that perfectly blends classic character with turn-key convenience. Positioned on a gorgeous, park-like 1-acre corner lot in highly sought-after Gaylordsville, this home has been introduced at a highly attractive and competitive entry price to secure an immediate, smooth transaction. From the moment you step inside, you will feel entirely at home. The heart of the residence is a custom chef's kitchen anchored by a massive granite entertaining island, timeless subway tile, and premium stainless steel appliances-perfect for hosting family gatherings. Step down into the breathtaking, light-filled family room, where soaring cathedral ceilings, rustic exposed wood beams, and a magnificent brick fireplace create a cozy, unforgettable atmosphere for crisp autumn nights. The seamless indoor-outdoor flow transitions effortlessly to an expansive rear deck, overlooking a peaceful, private backyard oasis. Complete with a luxurious primary suite and a massive, fully finished walk-out lower level (ideal for a home gym, theater, or remote workspace), every inch of this home has been designed to elevate your lifestyle. YOUR OPPORTUNITY IS NOW. The seller is highly motivated, actively preparing for their next chapter, and ready to review all competitive proposals. Bring your best offer!

2 Pilgrims Way, New Milford
22 Waller Rd, New Milford
$399,000
4 Beds ⋅ 2 Baths ⋅ 24202055 MLS
Character, charm, privacy, and move in ready home come together in this beautifully renovated 4-bedroom, 2-bathroom home set on over 1.5 picturesque acres. Thoughtfully updated while preserving its inviting character, the home features a new kitchen, renovated bathrooms, new windows, and new flooring, offering the comfort of modern living without sacrificing charm. Enjoy peaceful views and the soothing sounds of a babbling brook in the distance, creating a serene backdrop for everyday living or as a weekend retreat. The property offers endless possibilities for outdoor enthusiasts, nature lovers, or artists seeking privacy and inspiration. The walk-out lower level provides additional flexible space and easy access to the outdoors. A wonderful opportunity to enjoy privacy and tranquility while maintaining convenient access to everyday amenities. Inviting and full of character-this special property is ready to welcome you home.

22 Waller Rd, New Milford
41 Colonial Ridge Dr, New Milford
$624,900
4 Beds ⋅ 3 Baths ⋅ 24201406 MLS
If you've been dreaming of the perfect blend of peaceful living and everyday convenience, this classic Colonial delivers! Watch the sun rise from the spacious new deck with black metal balusters. Set on over an acre in a friendly, walkable neighborhood, this spacious 4BR home w/3 remodeled baths offers charm, thoughtful updates & room to grow. The center-hall foyer opens to large formal living & dining rooms, an office/den/poss 5th BR, and a beautifully renovated kitchen w/ceiling-height maple cabinetry, granite counters w/elegant Ogee edging, tumbled marble backsplash, large center island with seating, and stainless appliances-including a pot-filler over the range! The vaulted family room steals the show with exposed beams, a dramatic two-story brick fireplace, built-ins and sliders to a new oversized deck, perfect for summer gatherings. Upstairs are four generous bedrooms with a walk-in closet in the MBR and Closetmaid systems in the others, two updated full baths (think glass shower, tumbled marble bullnose chair rail, wainscoting, detailed tile, and even a chandelier over the soaking tub.) The finished lower level adds a large, tiled rec/play room, laundry and storage, while two separate, extended garage bays provide even more room. Rest easy, as recent improvements include roof, Anderson windows, boiler, oil tank, driveway and deck. Just 10 minutes to NY trains, Appalachian Trail access, recreational amenities, and Candlewood Lake-classic Connecticut living at its best

41 Colonial Ridge Dr, New Milford
23 Front Of The Mountain Rd, New Milford
$895,000
2 Beds ⋅ 2 Baths ⋅ 24187580 MLS
Discover the perfect balance of architectural distinction, modern sophistication and serene nature at this stunning, custom-built retreat. The concept was brought to life in 2020 by a renowned local Architect & Designer team. Expertly crafted with high-quality construction, the home features a sleek shiplap exterior and a design that prioritizes both aesthetics and performance. This house is remarkably energy-efficient and built to last. The Curated Interior Living Space is defined by warmth and high-end design. The main living area features wide-plank white pine flooring, double height ceiling and thoughtfully curated fixtures, including a striking 50-inch Isamu Noguchi Akari light sculpture in the great room and custom Articolo glass pendants in the stairwell. The chef's kitchen is equipped with high-end Bosch appliances, hardwood maple cabinetry with custom pulls and a farmhouse sink, while the bathrooms offer a spa-like retreat with beautiful finishes such as an MTI soaking tub, Kohler Purist Collection Fixtures, Connecticut Blue Slate and Carrara marble floor tiles. Plenty of storage throughout fitted with California closet organization and a bedroom on each level. The mezzanine offers a TV den, office space and a custom-built murphy bed, perfect for guests. The great room and expansive deck are oriented to capture seasonal sunset views; designed to blur the line between indoor and outdoor living. Directly abutting conservancy land for protected peace & views!

23 Front Of The Mountain Rd, New Milford
685 Kent Rd, New Milford
$595,000
5 Baths ⋅ 24108523 MLS
Church for sale! Available to be used as a new denomination, or converted to a residence. Beautiful sanctuary complete with pews with more in balcony. It has several large meeting/class rooms and an office, with two restrooms. Bell in steeple. Organ and piano. Could be converted into a very cool house! There is also a 2931 sf 3BR antique rectory house on the property, part of which has been rented as a residence and part of which has been used as office space. The residence part could use updates, or convert the entire building back to residential use.Church for sale with 2931 sf 3BR antique house adjacent.

685 Kent Rd, New Milford
685 Kent Rd, New Milford
$595,000
6 Baths ⋅ 24108370 MLS
Church for sale! Available to be used as a new denomination, or converted to a residence. Beautiful sanctuary complete with pews with more in balcony. It has several large meeting/class rooms and an office, with two restrooms. Could be converted into a very cool house! There is also a 2931 sf 3BR antique rectory house on the property, part of which has been rented as a residence and part of which has been used as office space. The residence part could use updates, or convert the entire building back to residential use. May be suitable for a home based business in R-40 zone. This is a listing where you need to see it to understand the property. Schedule your private showing right away!

685 Kent Rd, New Milford
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