Moving to Winchester CT | real estate for sale in Winchester Connecticut | Property Statistics of living in Winchester
Winchester, including the village of Winsted, offers a diverse housing market with historic homes, multifamily properties, and more affordable residential opportunities. The town serves as an important regional center in northwestern Connecticut. Affordability and access to outdoor recreation attract a wide range of buyers. While prices are generally lower than in many southern Litchfield County communities, ongoing revitalization efforts may support future appreciation.
205 Wallens Street
Winchester, Connecticut 06098
$600,000 | Active
4 Beds | 3 Baths | 3486 Sqft | 2.03 Acres | 1 Days on Market
Property Type: Single Family For Sale
Welcome to this beautifully crafted 3,486 sq. ft. Colonial, offering exceptional quality, thoughtful design, and plenty of space both inside and out. Set privately on 2.03 acres at the end of a long driveway, this 10-room home was built in 2007 and has been meticulously maintaine...
804 Wakefield Boulevard
Winchester, Connecticut 06098
$799,900 | Active
2 Beds | 1 Baths | 1044 Sqft | 0.08 Acres | 2 Days on Market
Property Type: Single Family For Sale
Experience an everyday vacation at 804 W. Wakefield Blvd on beautiful Highland Lake! This exceptional turnkey, year-round waterfront retreat is ideal as a primary residence, weekend escape, vacation home, or income-producing rental. Perfectly positioned on the widest part of High...
600 Wakefield Boulevard
Winchester, Connecticut 06098
$649,900 | Active
2 Beds | 1 Baths | 1361 Sqft | 0.11 Acres | 7 Days on Market
Property Type: Single Family For Sale
Set along the highly desirable east side of Highland Lake, 600 East Wakefield Boulevard offers a unique opportunity to create a waterfront retreat tailored to your lifestyle. Brimming with charm and character, this home is ready for its next chapter and the fresh vision. Spend yo...
46 Cherry Street
Winchester, Connecticut 06098
$199,900 | Active
4 Beds | 2 Baths | 1376 Sqft | 0.37 Acres | 15 Days on Market
Property Type: Single Family For Sale
A wonderful opportunity to own a spacious antique Colonial with endless potential! This 4-bedroom, 2-full-bath home features a living room, dining room, and an eat-in kitchen, providing a solid foundation for your vision. While the home would benefit from updates, it offers an ex...
122 Standard Avenue
Winchester, Connecticut 06098
$399,900 | Active
4 Beds | 2 Baths | 1944 Sqft | 0.92 Acres | 11 Days on Market
Property Type: Single Family For Sale
Well-maintained 4-bedroom Colonial tucked away on a quiet dead-end street. This inviting home features a newly renovated eat-in kitchen with updated cabinetry, countertops, and finishes, perfect for everyday living and gathering. The comfortable layout includes a spacious living ...
70 Walnut Street
Winchester, Connecticut 06098
$349,900 | Active
4 Beds | 2 Baths | 2722 Sqft | 0.13 Acres | 30 Days on Market
Property Type: Single Family For Sale
Step back in time and experience the timeless elegance of this spacious 2,722 sq. ft. Victorian offering 10 rooms, 5 bedrooms, and 1.5 baths. Rich in original character and architectural detail, this classic home showcases beautiful hardwood floors, impressive natural woodwork, p...
132 Lake Street
Winchester, Connecticut 06098
$365,000 | Active
3 Beds | 2 Baths | 1820 Sqft | 0.23 Acres | 63 Days on Market
Property Type: Single Family For Sale
Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breeze...
103 Cordano Road
Winchester, Connecticut 06098
$305,000 | Active
3 Beds | 2 Baths | 1442 Sqft | 2.26 Acres | 47 Days on Market
Property Type: Single Family For Sale
Well-maintained Cape in a desirable rural setting, yet just minutes from shopping, dining, schools, and other everyday conveniences. This 7-room home offers 3 bedrooms and 1.5 baths with a flexible floor plan designed for comfortable living. The main level features a formal livin...
55 Walnut Street
Winchester, Connecticut 06098
$429,000 | Active
5 Beds | 4 Baths | 5016 Sqft | 0.56 Acres | 566 Days on Market
Property Type: Single Family For Sale
Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900s. Nestled in the TCR Zone, this versatile building offers a wealth of potential....
812 Wakefield Boulevard
Winchester, Connecticut 06098
$749,900 | Under Contract - Continue
2 Beds | 1 Baths | 760 Sqft | 0.06 Acres | 14 Days on Market
Property Type: Single Family For Sale
Year-round waterfront retreat with breathtaking sunrise views from one of the widest sections of the lake! This well-maintained 2-bedroom, 1 bath home offers comfortable living with a flexible loft area for additional sleeping space and a convenient half bath on the lake level. T...
752 Lake Drive
Winchester, Connecticut 06098
$1,600,000 | Under Contract - Continue
4 Beds | 3 Baths | 2129 Sqft | 0.38 Acres | 22 Days on Market
Property Type: Single Family For Sale
Experience the best of lakefront living with breathtaking views, spectacular sunsets, and exceptional outdoor spaces. This amazing waterfront home features a brand-new 100 x 14 Brazilian hardwood deck, a 35 x 6 stationary Trex and steel dock, and a private cabana-perfect for rela...
729 Wakefield Boulevard
Winchester, Connecticut 06098
$320,000 | Under Contract
2 Beds | 1 Baths | 1128 Sqft | 0.23 Acres | 1 Days on Market
Property Type: Single Family For Sale
Lake views that will knock your socks off! Welcome to your own slice of paradise on the shores of Highland Lake, where every day feels like a vacation. Perfectly positioned on one of Connecticuts most sought-after lakes. This home needs some love, but has great bones! Bring your ...
104 Maloney Court
Winchester, Connecticut 06098
$279,000 | Under Contract
3 Beds | 1 Baths | 1008 Sqft | 0.31 Acres | 66 Days on Market
Property Type: Single Family For Sale
Perched on desirable Wallens Hill with beautiful western sunset views, this lovingly maintained 3 bed 1957 ranch is full of warmth, charm, and pride of ownership. Bright and sunny throughout, the home offers 1,008 square feet of comfortable living space with hardwood floors, cent...
624 Wynne Road
Winchester, Connecticut 06098
$124,900 | Under Contract - Continue
2 Beds | 1 Baths | 672 Sqft | 0.12 Acres | 79 Days on Market
Property Type: Single Family For Sale
Exceptional opportunity to build near one of Northwest Connecticuts most desirable lake communities. Just steps from beautiful Highland Lake, this water-view parcel offers the chance to create your dream home in a setting that combines lake lifestyle, natural beauty, and convenie...
121 Wakefield Boulevard
Winchester, Connecticut 06098
$679,000 | Under Contract - Continue
4 Beds | 4 Baths | 2265 Sqft | 1 Acres | 113 Days on Market
Property Type: Single Family For Sale
PRICE REDUCTION !! Discover unparalleled Highland Lake living with this exceptional 1.00-acre retreat, boasting 50 feet of direct lake frontage and a newly renovated dock/deck. Enjoy breathtaking water views from your sunroom, dining room, and multiple bedrooms within this versat...
195 Reaching Hill Road
Winchester, Connecticut 06098
$353,500 | Under Contract - Continue
3 Beds | 2 Baths | 1324 Sqft | 0.93 Acres | 20 Days on Market
Property Type: Single Family For Sale
Please submit your clients highest and best offer by Sunday 07/19 at 3:00 PM. Beautifully remodeled and move-in ready, 195 Reaching Hill Rd in Winsted, CT features modern updates, comfort, and functionality throughout. This 3-bedroom, 2-bath conventional-style home sits on nearly...
119 Wakefield Boulevard
Winchester, Connecticut 06098
$849,900 | Active
4 Beds | 2 Baths | 1781 Sqft | 0.62 Acres | 38 Days on Market
Property Type: Single Family For Sale
Have you been dreaming of breathtaking lake views and a property that is truly special, unique, and turn-key? This exceptional home includes 50 feet of waterfront access with a boat dock and lift, making it a dream for lake enthusiasts! Nestled across from the tranquil First Bay,...
426 Platt Hill Road
Winchester, Connecticut 06098
$679,900 | Under Contract - Continue
3 Beds | 3 Baths | 3086 Sqft | 3 Acres | 39 Days on Market
Property Type: Single Family For Sale
Custom built log Home!This home sits on a 3 acre, private landscaped lot with mountains laurel and a park nearby. This sprawling home with a covered front porch(28x 8)is perfect for relaxing and features over 1100 sq of decking which wraps around the house for entertaining. The H...
293 Torringford Street
Winchester, Connecticut 06098
$495,000 | Under Contract - Continue
4 Beds | 3 Baths | 3834 Sqft | 22.23 Acres | 36 Days on Market
Property Type: Single Family For Sale
Unique opportunity to own this spacious 4-bedroom Colonial set on 27 acres in Winchester, CT. Previously home to animals, this property offers endless possibilities for hobby farming, equestrian pursuits, recreation, or simply enjoying the privacy and beauty of the countryside. I...
111 Moore Avenue
Winchester, Connecticut 06098
$250,000 | Under Contract
3 Beds | 1 Baths | 1392 Sqft | 0.62 Acres | 5 Days on Market
Property Type: Single Family For Sale
*Deadline set of Tuesday 6/30 at Noon. Seller reserves the right to take an offer at anytime.* Nestled on a well maintained lot, this charming Cape offers the perfect balance of privacy and convenience. Set just off the beaten path, the property enjoys a peaceful, rural feel whi...
441 Platt Hill Road
Winchester, Connecticut 06098
$474,900 | Under Contract
5 Beds | 3 Baths | 3404 Sqft | 2.09 Acres | 13 Days on Market
Property Type: Single Family For Sale
Tucked away on 2.09 private acres in the desirable Platt Hill area of Winchester, this custom-built contemporary offers the perfect blend of architectural character, space, and recent updates. With over 3,400 square feet, 5 bedrooms, 3 full baths, and a 2-car garage, this home pr...
107 Roberts Avenue
Winchester, Connecticut 06098
$349,000 | Under Contract - Continue
3 Beds | 2 Baths | 1888 Sqft | 1.6 Acres | 63 Days on Market
Property Type: Single Family For Sale
Peaceful country living with unlimited potential! Nestled on a quiet Winsted street, this three bedroom, two bathroom ranch sits on nearly 2 acres of private, setback land. It offers excellant structural bones and a functonal layout, making it an ideal candidate for a rewarding r...
9 Loomis Street
Winchester, Connecticut 06098
$469,900 | Active
3 Beds | 2 Baths | 1768 Sqft | 0.35 Acres | 89 Days on Market
Property Type: Single Family For Sale
Spacious 3 to 4 Bedroom Colonial Style Home on a 0.35 Acre Lot, plus located on a No Through Street. OPEN FLOOR PLAN. Beautifully Remodeled from TOP TO BOTTOM for Energy Efficient Living. Redesigned Country Style Kitchen offers Ample Cabinetry and includes New Oven/Range, Microwa...
184 Smith Hill Road
Winchester, Connecticut 06098
$765,000 | Under Contract - Continue
3 Beds | 3 Baths | 4387 Sqft | 8.46 Acres | 77 Days on Market
Property Type: Single Family For Sale
Beautiful Private Brick/Clapboard Tudor set back on 8.46 private acres (which includes an extra 2+ acre abutting lot). New Hand Split Cedar Shingled Roof and new rebuilt brick chimney set off this custom elegant home. All warm cherry wood floors and special custom moldings throug...
29 Center Street
Winchester, Connecticut 06098
$239,000 | Active
7 Beds | 3 Baths | 2400 Sqft | 0.16 Acres | 118 Days on Market
Property Type: Single Family For Sale
Brand new to the market. Must see large 2 story Colonial featuring 13 rooms, 7 Bedrooms, 3 Bathrooms, Walk up attic and full basement. Includes a 2 story barn. Convenient location in the heart of town lends itself to easy access to many nearby amenities. As an investment this res...
469 Platt Hill Road
Winchester, Connecticut 06098
$895,000 | Active
4 Beds | 2 Baths | 3088 Sqft | 7.11 Acres | 110 Days on Market
Property Type: Single Family For Sale
HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether Youre an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately ...
118 Meadow Street
Winchester, Connecticut 06098
$269,999 | Under Contract
3 Beds | 2 Baths | 1652 Sqft | 0.17 Acres | 83 Days on Market
Property Type: Single Family For Sale
This charming historic home, built in 1860, blends timeless character with thoughtful updates. Featuring 3-4 bedrooms, this property offers flexible living space to meet your needs. The beautifully remodeled upstairs bathroom is a standout feature, offering modern comfort within ...