Connecticut Real Estate Search

Cheshire Homes for Sale

Newest Homes For Sale

349 Allen Rd Unit 12A, Torrington
$205,000
2 Beds ⋅ 1 Baths ⋅ 24216814 MLS ⋅ Allendale BLDG.
JUST BEAUTIFUL!! MOVE IN READY 2BR TOWNHOUSE. FRESHLY PAINTED IN THE PRIVATE, QUIET, 24 UNIT ALLENDALE COMPLEX, KITCHEN WITH GRANITE COUNTERTOPS, NEW STOVE, AND NEW KITCHEN FAUCET. MORE NEW FEATURES. NEWFLOORING FLOWING INTO THE DINING AREA AND HUGE LIVING ROOM. AND CONTINUING UPSTAIRS INTO THE GENEROUS SIZED BEDROOMS AND FULL BATH. WONDERFUL VIEWS THROUGHOUT GIVING A RELAXING FEELING IN THIS LIGHT AND SUNNY UNIT. EVERYTHING IS THERE WITH A LOWER-LEVEL GARAGE WITH UTILITY ROOM AND LAUNDRY. CLOSE TO ALL SHOPPING, RESTAURANTS AND MAJOR HIGHWAYS!!

349 Allen Rd Unit 12A, Torrington
22 Houlton St, Watertown
$232,000
3 Beds ⋅ 1 Baths ⋅ 24217075 MLS
Enjoy one-level living in this 3-bedroom, 1-bath home featuring hardwood floors. The screened-in porch opens to a spacious back deck, creating additional space to relax or entertain outdoors. A full unfinished basement offers abundant storage or the opportunity to customize the space to suit your needs. An attached 2-car garage adds everyday functionality. Access to Routes 8 and 6 connects you to local shopping, dining, schools, and services. Nearby recreation includes Echo Lake Park, Veterans Memorial Park, Crestbrook Park's golf course and tennis courts, and Black Rock State Park, offering opportunities for hiking, fishing, swimming, and enjoying the outdoors. A wonderful opportunity to make this home your own!

22 Houlton St, Watertown
48 Rockdale Ave, Watertown
$309,900
3 Beds ⋅ 1 Baths ⋅ 24217028 MLS
Beautifully renovated with modern finishes and thoughtful updates throughout, this charming three-bedroom home offers an inviting blend of style, comfort, and everyday functionality. The beautifully updated kitchen features all-new appliances, creating a fresh and welcoming space for cooking and gathering. A conveniently located first-floor bedroom adds flexibility to the home's layout, while the additional bedrooms provide comfortable living spaces. Set on approximately 0.30 acres, the property offers outdoor space to relax, entertain, and enjoy the changing seasons. Completely renovated and move-in ready, this home offers modern comfort in an established neighborhood. Nestled in the Oakville section of Watertown, it enjoys a convenient location close to shopping, dining, parks, and everyday essentials, with easy access to Waterbury and major commuter routes. A wonderful place to call home, with everything you need just moments away.

48 Rockdale Ave, Watertown
337 Kent Rd, New Milford
$777,000
3 Baths ⋅ 24215035 MLS
Amazing Opportunity to have your own commercial building right in the intersection of New Milford, Sherman, Gaylordsville and minutes to NY border. This building has been renovated top to bottom with over 200k in updates. Potential 9 room dividable rental spaces, full kitchen, 2 full baths and one-half bath. The possibilities are endless here. Wide plank refinished hardwood flooring in main areas. Newly painted inside and out. New Luxury vinal in several of the rooms. 2 baths redone top to bottom. Brand new Roth tanks for efficient/ clean heating. Propane heat and central ac in upstairs apartment, plus brand-new roof over whole right-side apartment. This building is a true gem!! Owner Agents

337 Kent Rd, New Milford
27 Roberts Ave, Watertown
$470,000
4 Beds ⋅ 2 Baths ⋅ 24216969 MLS
Rich in New England charm, this Colonial blends timeless character with inviting outdoor spaces in a desirable Watertown location. The home welcomes you with a convenient mudroom, leading to a sun filled kitchen that continues the New England charm with a distinctive tin ceiling, farmhouse sink, and granite countertops with all stainless steel appliances. The main level also features a traditional foyer, a spacious dining room, and a living room anchored by the fireplace, with access to a covered side porch great for hosting or just sipping on a morning coffee. Upstairs, four bedrooms with hardwood floors throughout, a full bath, and a large walk up attic offering endless possibilities for the future or just as great storage. Rounding out the house is a detached two car garage, greenhouse, and a peaceful brook winding along the property, all complemented by established gardens throughout the entire exterior that only add to the property's appeal! Meanwhile, a new roof on both the house and garage in 2025 provides a valuable recent update. Ideally situated a short walk away from Watertown's historic Main Street, local shops, restaurants, major routes, and Taft School, this distinctive property combines the character of an older charm with a setting and location that are hard to find!

27 Roberts Ave, Watertown
15 Chatham Ct, Goshen
$549,000
4 Beds ⋅ 2 Baths ⋅ 24215512 MLS
Experience the ultimate lake community lifestyle in this beautifully updated 4 bed, 2 bath Contemporary Split-Level home offering over 2,000 sq ft of charm and modern living space. Situated on a private, nearly 1 acre lot on a cul-de-sac, this home combines thoughtful updates with serene natural surroundings just moments from the Woodridge Lake clubhouse, beach, and amenities. Step inside to an open and light filled floor plan featuring all new flooring, stylish new lighting fixtures, and tastefully updated bathrooms. The inviting main living area showcases a fireplace anchored by a new pellet-burning stove insert and a striking accent wall, perfect for cozying up after a day on the lake. The spacious bedrooms include plush, new carpeting and convenience being on the main floor and upstairs you'll find a loft currently office space with beautifully renovated primary bedroom and bathroom plus additional bedroom with new closet space and private balcony. Step outside to enjoy exceptional outdoor living: entertain on your expansive wraparound deck or relax in the screened in porch, ideal for 3-season enjoyment while taking in views of your private, wooded lot. Major mechanical and structural updates provide complete peace of mind, including a new roof and oil tank. An attached, under house 2 car garage provides convenience and extra storage space. Don't miss this rare opportunity to own a wonderfully renovated home in one of Goshen's most desirable lake communities.

15 Chatham Ct, Goshen
135 New Harwinton Rd, Torrington
$344,900
4 Beds ⋅ 2 Baths ⋅ 24216972 MLS
Welcome to 135 New Harwinton Road! This charming four-bedroom Cape combines inviting living spaces with a flexible layout. An enclosed front porch leads inside to an updated kitchen, formal dining room, comfortable living room, and separate family room-offering plenty of space to relax and entertain. A main-level bedroom adds convenience, while an additional room with deck access makes an ideal home office or den. Enjoy outdoor gatherings on the deck overlooking a spacious backyard with a stream along the rear of the property. A detached two-car garage and full unfinished basement provide ample storage. Conveniently located near downtown Torrington's shops and restaurants, Torrington Commons Shopping Center, and Coe Memorial Park, with easy access to Route 8 for commuting and exploring the surrounding area. Schedule your private showing today!

135 New Harwinton Rd, Torrington
70 Eastwood Hall Rd, Watertown
$615,000
3 Beds ⋅ 3 Baths ⋅ 24216854 MLS
Located in Watertown's desirable Taft area with views of Watertown Golf Club, this 3 bedroom, 2.5 bath Colonial offers light filled spaces and modern updates throughout. Enjoy hardwood floors, a remodeled kitchen with granite counters, stainless steel appliances, beverage bar and custom pantry with butcher block top. The family room features vaulted ceilings, a fireplace and double doors leading to a newly installed deck-perfect for indoor/outdoor entertaining. Completing the main floor is a dining room with large picture window offering views of the private yard and a formal living area. This space offers flexibility for your growing needs! Upstairs, you have 3 nicely sized bedrooms, a full bath and laundry for convenience. A remodeled primary suite features a walk in closet and private bath. Major Updates in the last 5 years include: Roof, Siding, Windows, Furnace, Central Air and Solar Panels. Full list in attachments! Move right in and enjoy the perfect blend of modern updates, outdoor living and room to entertain in Watertown's sought after Taft area!

70 Eastwood Hall Rd, Watertown
264 Florence St, Winchester
$265,000
3 Beds ⋅ 2 Baths ⋅ 24213670 MLS
Charming 3 bedroom 2 bath Cape, Oil heat with Natural gas connected if you'd prefer to switch over at some point. Nicely landscaped yard, repl windows, propane insert fireplace, wood floors, wired for a portable generator, new garage door (2025), furnace (2003), hot water heater (2026), 100 amp service, Central air. Well established, wonderful neighborhood, priced to sell. Rare opportunity to downsize or realize the dream of your 1st home!

264 Florence St, Winchester
49 South St, Washington
$895,000
24214861 MLS
Bring your architect and your ambition-your slice of paradise is ready to be built. Western Sunset Views, a short distance from The Mayflower Inn and Washington Green. Discover the ultimate renovation project or the foundation for your future estate. Also, included 1890s Barn-style home-complete with its signature silo and 1970s additions-awaits a visionary touch. Whether you envision a meticulous restoration of a historic showpiece or a chic, modern transformation, the potential here is as vast as the western horizon. The acreage has been strategically cleared to unveil stunning western exposures. The property is anchored by a mature landscape, featuring: Stone Terrace & Deck: Perfect for seamless indoor-outdoor entertaining. Rustic Writer's Cottage: A charming, detached retreat for creative pursuits or a quiet home office. Additional structures offering utility and historic character. The interior features an existing open floor plan, providing a fluid transition between the kitchen, dining, and living areas. Renovate the existing structure into a sprawling, personalized dream retreat that blends 19th-century charm with 21st-century luxury. The Guest House Strategy: Scale back the current residence to serve as a sophisticated guest house or secondary dwelling while you build a new primary manor. Note: current home requires a new septic --

49 South St, Washington
28 Horse Heaven Rd, Washington
$1,900,000
3 Beds ⋅ 4 Baths ⋅ 24216723 MLS
Set on five pristine acres along a quiet country road in Washington, Connecticut, this charming home offers exceptional privacy and beautiful western views over the surrounding hills. Mature gardens and a lovely bluestone patio create an inviting outdoor setting. Inside, an open floor plan, high ceilings, and hardwood floors throughout provide bright, spacious living areas. The beautifully designed kitchen features a long center island and flows seamlessly into the main living spaces, making it ideal for entertaining. The home offers four bedrooms and 3.5 bathrooms, including a spacious guest suite above the garage that could also serve as the primary. A wonderful loft provides additional space for the library/billiards room, while the finished basement offers a game/playroom. There is a town approved pool site. A wonderful combination of comfort, privacy, and natural beauty in one of Washington's most desirable locations

28 Horse Heaven Rd, Washington
1144 Old Northfield Rd, Thomaston
$310,000
2 Beds ⋅ 2 Baths ⋅ 24216703 MLS
Well-maintained 3-bedroom raised ranch set on a spacious half-acre lot. The main level features a large living room, country kitchen with a door leading to the back deck, and hardwood floors throughout the upper level. The full bathroom was updated in 2026 with a new walk-in shower (no tub), linen closet, and convenient access to the primary bedroom. Two additional bedrooms complete the main level. The lower level offers a comfortable family room with tongue-and-groove paneling, woodstove, and electric heat, along with a full bathroom with shower added in 2022. A separate laundry room with well tank, additional storage space, and a one-car garage provide added convenience and functionality. A great opportunity to enjoy comfortable living with flexible space inside and room to enjoy the outdoors.

1144 Old Northfield Rd, Thomaston
35 Raven Rock Rd, Roxbury
$12,995,000
5 Beds ⋅ 8 Baths ⋅ 24216276 MLS
Privately set at the crest of a hill beyond a gated drive, 35 Raven Rock Road commands breathtaking views across miles of bucolic Litchfield County countryside and the Shepaug River Valley. Spanning over 114 acres, this exceptional country compound offers extraordinary privacy, with 20+ acres of cultivated lawns, extensive gardens, sculptures, pond and specimen trees creating a remarkable estate setting. Built in 2002, the approximately 13,600 SF stone and slate residence pairs gracious proportions with exquisite finishes, superb custom millwork, marble floors, and 8 fireplaces. A marble entry hall leads to an elegant living room opening onto an expansive stone terrace overlooking the grounds and countryside. A formal dining room, paneled library and inviting family room adjoining a heated porch provide beautiful settings for entertaining and everyday living. The chef's kitchen features a professional range, Traulsen refrigeration and a separate cooking room with charbroilers and a stone pizza oven. The main-level primary suite offers a fireplace, dual walk-in closets, separate water closets and a marble bath. Four additional bedrooms feature en suite baths, complemented by an upstairs media/rec room. The finished lower level includes a gym, steam room, cedar closets and wine cellar. A heated pool, pool house, Har-Tru tennis court, 4-car garage with guest quarters and heated barn enrich the estate. Major infrastructure upgrade includes newly installed additional well system.

35 Raven Rock Rd, Roxbury
589 Kent Rd, New Milford
$299,900
2 Beds ⋅ 1 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
53 Orchard Rd, North Canaan
$499,000
3 Beds ⋅ 2 Baths ⋅ 24214550 MLS
Welcome to this beautifully renovated and professionally decorated 3-bedroom, 2-full-bath ranch, offering the perfect combination of style, comfort, and easy one-level living! Thoughtfully updated throughout, this home features a spacious, flowing floor plan, abundant closet space, and tasteful finishes that create a warm and inviting atmosphere. The beautifully landscaped, level lot provides a wonderful setting for outdoor enjoyment, while the gorgeous rear stone patio is perfect for entertaining or simply relaxing. Recent improvements include new appliances, new windows, a new oil burner, updated electrical panel, totally renovated bathroom, and the addition of a third bedroom, adding valuable living space and functionality. The flexible layout also offers potential for an in-law arrangement, providing options for extended family or guests. Truly move-in ready, this exceptional home offers the charm of ranch-style living with the benefits of extensive modern updates.

53 Orchard Rd, North Canaan
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!