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.
812 Wakefield Boulevard
Winchester, Connecticut 06098
$749,900 | Active
2 Beds | 1 Baths | 760 Sqft | 0.06 Acres | 2 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...
138 Rockwell Street
Winchester, Connecticut 06098
$189,000 | Active
3 Beds | 2 Baths | 1664 Sqft | 0.17 Acres | 2 Days on Market
Property Type: Single Family For Sale
Welcome to 138 Rockwell Street in charming Winchester, CT! This inviting home offers a wonderful blend of comfort, character, and everyday convenience. Step inside to discover bright living spaces filled with natural light, a functional layout, and generously sized rooms designed...
103 Cordano Road
Winchester, Connecticut 06098
$324,900 | Active
3 Beds | 2 Baths | 1442 Sqft | 2.26 Acres | 16 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...
121 Wakefield Boulevard
Winchester, Connecticut 06098
$679,000 | Active
4 Beds | 4 Baths | 2265 Sqft | 1 Acres | 101 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...
119 Wakefield Boulevard
Winchester, Connecticut 06098
$849,900 | Active
4 Beds | 2 Baths | 1781 Sqft | 0.62 Acres | 7 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,...
46 Cherry Street
Winchester, Connecticut 06098
$199,900 | Active
4 Beds | 2 Baths | 1376 Sqft | 0.37 Acres | 5 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...
147 E. Wakefield Boulevard
Winchester, Connecticut 06098
$269,900 | Active
2 Beds | 1 Baths | 702 Sqft | 0.24 Acres | 65 Days on Market
Property Type: Single Family For Sale
Come enjoy Highland Lake living just in time for Summer. Relax in this one level living, cozy cottage home with views of the lake from your deck and just a short distance to Resha beach. Enter through a large mudroom to your open living room with large window to let in natural li...
195 Reaching Hill Road
Winchester, Connecticut 06098
$353,500 | Active
3 Beds | 2 Baths | 1324 Sqft | 0.93 Acres | 8 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...
132 Lake Street
Winchester, Connecticut 06098
$389,900 | Active
3 Beds | 2 Baths | 1820 Sqft | 0.23 Acres | 32 Days on Market
Property Type: Single Family For Sale
Welcome to East Lake Street at Highland Lake, where privacy, comfort, and year-round recreation come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained 2-story home offers peaceful surroundings, refreshing breezes, and glimpses...
426 Platt Hill Road
Winchester, Connecticut 06098
$679,900 | Under Contract - Continue
3 Beds | 3 Baths | 2806 Sqft | 3 Acres | 27 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...
752 Lake Drive
Winchester, Connecticut 06098
$1,600,000 | Active
4 Beds | 3 Baths | 2129 Sqft | 0.38 Acres | 10 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...
30 Upland Road
Winchester, Connecticut 06098
$220,000 | Under Contract
4 Beds | 2 Baths | 1844 Sqft | 0.17 Acres | 45 Days on Market
Property Type: Single Family For Sale
Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood while still being close to many local amenities. Hardwood floors run throughout the home, adding warmth and character, and the tree-lined backyard offers a privat...
70 Walnut Street
Winchester, Connecticut 06098
$369,900 | Coming Soon
4 Beds | 2 Baths | 2722 Sqft | 0.13 Acres | 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...
736 Wakefield Boulevard
Winchester, Connecticut 06098
$544,000 | Under Contract
1 Beds | 2 Baths | 1308 Sqft | 0.2 Acres | 27 Days on Market
Property Type: Single Family For Sale
Welcome to WatersEdge a Seasonal Cottage perched on a landscaped hillside overlooking Third Bay of beautiful Highland Lake. Views Views Views! Highland is a fully recreational lake. On the main floor of the cottage you will find one bedroom, a bath with shower, a spacious family...
293 Torringford Street
Winchester, Connecticut 06098
$495,000 | Under Contract - Continue
4 Beds | 3 Baths | 3834 Sqft | 22.23 Acres | 24 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...
237 Wallens Hill Road
Winchester, Connecticut 06098
$579,900 | Active
4 Beds | 3 Baths | 2628 Sqft | 0.82 Acres | 29 Days on Market
Property Type: Single Family For Sale
Welcome to 237 Wallens Hill Road, where comfort, quality, and exceptional entertaining spaces come together in a beautiful rural setting. This 9-room Colonial with a farmhouse front porch is set on .80 acres and offers 4 bedrooms and 2.5 baths. The main level features a formal di...
104 Maloney Court
Winchester, Connecticut 06098
$279,000 | Under Contract - Continue
3 Beds | 1 Baths | 1008 Sqft | 0.31 Acres | 60 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...
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 | 51 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...
624 Wynne Road
Winchester, Connecticut 06098
$174,900 | Active
2 Beds | 1 Baths | 672 Sqft | 0.12 Acres | 67 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...
660 Wakefield Boulevard
Winchester, Connecticut 06098
$749,999 | Under Contract
2 Beds | 2 Baths | 1320 Sqft | 0.27 Acres | 8 Days on Market
Property Type: Single Family For Sale
Nestled along the coveted east side of Highland Lake, 660 East Wakefield Blvd offers a rare opportunity to create the waterfront retreat youve always imagined. Bursting with classic lake charm and timeless character, this home is ready for a new owner to make it their own and bri...
9 Loomis Street
Winchester, Connecticut 06098
$469,900 | Active
3 Beds | 2 Baths | 1768 Sqft | 0.35 Acres | 58 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 | 65 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 | 87 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...
431 Wakefield Boulevard
Winchester, Connecticut 06098
$1,850,000 | Active
9 Beds | 6 Baths | 7000 Sqft | 3 Acres | 106 Days on Market
Property Type: Single Family For Sale
Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the pe...
55 Walnut Street
Winchester, Connecticut 06098
$449,000 | Active
5 Beds | 4 Baths | 5016 Sqft | 0.56 Acres | 535 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....
469 Platt Hill Road
Winchester, Connecticut 06098
$895,000 | Active
4 Beds | 2 Baths | 3088 Sqft | 7.11 Acres | 79 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 ...