Refine Search
Map
Sort by
$124,900
2 Beds ⋅ 1 Baths ⋅ 24174996 MLS
Exceptional opportunity to build near one of Northwest Connecticut's 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 convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a picturesque, natural lake in historic Winchester, spanning approximately 444-445 acres, about three miles long, with three distinct bays and depths reaching approximately 63 feet. Known for boating, fishing, swimming, and year-round enjoyment, Highland Lake has long been treasured for its scenic shoreline, established lake community, and recreational appeal. The lake is also recognized by Connecticut DEEP with a public boat launch and boating regulations, further supporting its active recreational use. The location is equally compelling: enjoy the peaceful feel of a classic Litchfield County lake setting while remaining convenient to Salisbury, Lakeville, Norfolk, Torrington, and downtown Winsted. Hartford is roughly 40 minutes away by car, making this an ideal retreat without sacrificing accessibility.

624 Wynne Rd, Winchester
$124,900
24175027 MLS
Exceptional opportunity to build near one of Northwest Connecticut's 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 convenient access to some of Litchfield County's most sought-after destinations. Highland Lake is a true Connecticut gem-a picturesque, natural lake in historic Winchester, spanning approximately 444-445 acres, about three miles long, with three distinct bays and depths reaching approximately 63 feet. Known for boating, fishing, swimming, and year-round enjoyment, Highland Lake has long been treasured for its scenic shoreline, established lake community, and recreational appeal. The lake is also recognized by Connecticut DEEP with a public boat launch and boating regulations, further supporting its active recreational use. The location is equally compelling: enjoy the peaceful feel of a classic Litchfield County lake setting while remaining convenient to Salisbury, Lakeville, Norfolk, Torrington, and downtown Winsted. Hartford is roughly 40 minutes away by car, making this an ideal retreat without sacrificing accessibility.

624 Wynne Rd, Winchester
$765,000
3 Beds ⋅ 3 Baths ⋅ 24173895 MLS
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 throughout the home add charm. Classy center island Kit with new subzero, granite counters & bow window-Fireplaced Dining room opens to large back deck overlooking fenced in private backyard-Massive sunken fireplaced living room -1st floor office-Private fireplaced Family room-huge master suite with fireplaced sitting room,walk-in closet & thermo-spa master bath. Large upper level bonus room with cozy private office-CAIR& whole house generator system are pluses-Beautiful professionally landscaped private level yard add lasting ambiance to this special home

184 Smith Hill Rd, Winchester
$895,000
4 Beds ⋅ 2 Baths ⋅ 24172121 MLS
HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 , 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, New propane heat in the sunken living room,200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!

469 Platt Hill Rd, Winchester
$200,000
24171867 MLS
Look no further for A Very Private location to build your Dream Home. A Wooded Hill top building site overlooking beautiful Winchester Center which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester. Convenient access agreement to the Rear lot is though 151 Chapel Rd. property.

00 Chapel Rd, Winchester
$250,000
24170540 MLS
One-of-a-Kind Opportunity! Don't miss your chance to own this turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location.-Owner Financing Available! This well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year track record of success and a loyal customer base, this restaurant has earned recognition in top publications including the New York Times, Wall Street Journal, Hartford Courant, CT Magazine, and numerous local publications - Sale includes the business only (real estate excluded) and comes fully equipped with all infrastructure items. This is a rare opportunity to step into a thriving, reputable restaurant with an exceptional reputation-ready to operate from day one - Numerous infrastructure items are included in the sale totaling well over 100k (See list in attached docs)

436 Main St, Winchester
$239,000
7 Beds ⋅ 3 Baths ⋅ 24169258 MLS
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 residence also has great potential to convert to a multi family home or could be renovated for commercial office space. The possibilities are endless. The barn has the capability for multiple uses as well such as a workshop, studio, office, storage or to just park vehicles.

Winchester
$549,000
11 Beds ⋅ 6 Baths ⋅ 24166332 MLS
*PRICE REDUCTION* 150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3-4 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

150 Oak St, Winchester
$595,000
24165997 MLS
Property is visible from Route 44 (AKA Main St)and fronts on Willow St. and Case Ave. The facility has been an auto dealer, a boat dealer, and a storage facility. The building has a total of 12 overhead doors.

45 Willow St, Winchester
$679,000
4 Beds ⋅ 4 Baths ⋅ 24159801 MLS
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 versatile 4/5 bedroom home. A unique first-floor suite with a separate exterior entrance offers ideal flexibility as a main-floor master or in-law accommodation. The upper-level primary suite boasts a private balcony perfect for savoring morning coffee while overlooking the shimmering lake. Entertain effortlessly in the large private backyard space, complete with an expansive 2 tier deck and built-in fire pit. Recent major upgrades ensure worry free enjoyment, including a high-efficiency HVAC (2024), new roof (2022), new siding, exterior doors, added insulation, two remodeled baths, full interior paint, and newer carpet throughout. Extensive landscaping has been completed, including new front railings, leveling and removal of several large trees. Previously a successful Airbnb, this property offers abundant parking, a two-car garage, and dual laundry facilities. Embrace all seasons on Highland Lake - from summer boating and fishing, lake is stocked with trout and bass for fishing enthusiasts, to winter ice skating/fishing. Your lakeside dream awaits!

121 W Wakefield Blvd, Winchester
$1,850,000
9 Beds ⋅ 6 Baths ⋅ 24159989 MLS
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 perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

431 W Wakefield Blvd, Winchester
$1,900,000
1 Baths ⋅ 24154804 MLS
Property Highlights * 12,000 SF steel building - newly constructed, divided into eight (8) units of approximately 1,500 SF each, featuring modern design and high-quality materials * Sits on 20+ acres of land offering flexibility, privacy, and space for future expansion * Outstanding road visibility and access * Zoned for commercial/industrial use - ideal for a range of operations (verify with town planning) * Build-to-suit layout - customizable interior walls or open-span layout based on buyer needs * Suitable for contractors, light manufacturing, logistics, agricultural storage, retail showroom, or mixed-use site planning Key Features * Durable steel-frame construction with low maintenance needs * High ceilings and wide interior spans allow for efficient space use * Options for service bays, warehouse space, contractor units, or equipment storage * Eight (8) overhead (drive-in) doors. * Utilities in place * Plenty of space for parking.

144 Rowley St, Winchester
$799,000
24157681 MLS
Uncover this hidden gem - 65.29 pristine acres of raw land, with natural beauty and endless potential. This picturesque parcel features serene ponds and mature trees. Distant views and incredible sunsets can be enjoyed from the property. Much site work has been done to date. A driveway with a binder course is already in place offering easy access into and throughout the property. Many acres have been cleared including stump removal and the land has been rough grated. Topsoil and additional natural materials remain on the property for future use. Currently, a small barn and shed exist on the property. A large crystal-clear pond is stocked with fish and includes a dock for fishing or personal enjoyment. Featuring 545 ft of frontage, this property offers excellent potential for subdivision.

257-259 Torringford St, Winchester
$69,000
24143845 MLS
Well-maintained second-floor office condo in excellent condition, offering a versatile and efficient layout for a variety of professional uses. The space features three private offices, a generous bullpen area that can accommodate 4-6 desks, and ample storage throughout. The property offers ample parking, making it convenient for both staff and clients. Located just minutes from downtown, the building is home to a strong mix of professional neighbors, including an eye doctor, dentist, civil engineering firm, and attorney-an ideal setting for any business seeking a convenient and professional environment.

140 Willow St Unit STE 6, Winchester
$540,000
8 Baths ⋅ 24131609 MLS
**CALLING FOR ALL CASH/HARD MONEY INVESTORS! ** Unlock the potential of this solid 7-unit brick building, featuring a versatile mix of 5 residential apartments and 2 commercial office spaces. Ideal for investors seeking reliable cash flow or developers exploring expansion opportunities, this property offers both immediate income and long-term upside. With proper zoning and approvals, the two office spaces could be converted into additional residential units. The owner currently covers electric for the office spaces. Owner also covers heat and water for all units. A spacious rear lot provides ample off-street parking for tenants. Conveniently located near Routes 8 and 44, this property offers easy access to shopping, dining, Northwestern Connecticut Community College, and a variety of recreational options, making it a consistently easy to rent location. Property to be sold "AS IS."

45 Elm St, Winchester
$879,990
24131284 MLS
Rare Multi-Parcel Land Opportunity 5 Contiguous Parcels | Colebrook & Winchester, CT Discover an exceptional land offering spanning five contiguous parcels across two of Litchfield County's most desirable rural towns. This unique property features a strong presence in highly sought-after Colebrook, known for its scenic beauty, low-density living, and unspoiled New England charm-paired with the convenience of nearby Winchester, offering easy access to shopping, dining, Bradley airport, and Highland Lake. This rare assemblage presents an opportunity to own a significant stretch of Connecticut countryside, where tranquility and natural beauty define the landscape. The property showcases a captivating blend of open meadows and mature woodland, providing both visual appeal and versatility. Elevated topography enhances privacy and offers potential for long-range views-hallmarks of the Colebrook setting. An established network of logging trails winds throughout the property, providing easy access to explore its natural features, including peaceful springs and gently flowing brooks that add to its character. Currently enrolled in Forest Land (490) classification, the property may offer tax advantages while preserving its natural integrity. A rare opportunity for outdoor enthusiasts, conservation-minded buyers, or visionary investors seeking a premier landholding in Northwestern Connecticut.

000000 Norfolk Rd, Winchester
$295,000
170078080 MLS
WINCHESTER CREST 51 acres of forested gently rolling land sited upland in Winchester Center. There is a former homesite and multiple choices for additional homesites affording complete privacy. There is abundant wildlife, trails, intermittent streams, dense and sparse forest. Perfect for year round home site, weekend retreat or recreational land.

393 Winchester Rd, Winchester
$449,000
24071862 MLS
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 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

55 Walnut St, Winchester
$59,900
170616672 MLS
105 & 107 Mountain Road parcels are contiguous and located on a dirt road . . Deed indicates right of way to Highland lake water frontage within walking distance. See documents attached for Deed , Site plan, Peculation tests , Survey and Septic testing available . Possible city sewer access at buyers expense . Seller will consider financing with a minimum of 15% DOWN PAYMENT FOR A 2 YEAR BALLOON MORTGAGE @7.5% WITH A 30 YEAR AMORTIZATION SCHEDULE .

105, 107 Mountain Rd, Winchester
$158,000
24003236 MLS
1.18 Acre ,Approximately 201 Ft Road fro . ntage )Lightly wooded E. Wakefield Blvd. lot located at the end of 3rd Bay . Panoramic view overlooking the length or lake. Survey , Zoning HL regulations and Deed are available , and Access is also available off E. Mtn Road . Survey shows Town of Winchester parcel with warterfront access Rare opportunity to build your dream home . , SELLER WILL CONSIDER HOLDING A 2 YEAR BALLOON MORTGAGE WITH 15% DOWN

843-845 (Lots - 10a, Winchester
$389,000
24122124 MLS
Welcome, You be the first, to come and conquer this land here in Winchester, Connecticut. There are 20.87 acres of virgin land. Come and build, do what you do best, you can have Peace and Privacy!!! There are no sidewalks, no streets that drive through. You are 40 minutes from multiple private schools. 16 minutes from Charlotte Hungerford Hospital. 1 hour from Tweed Airport New Haven. 39 minutes from Bradley Airport in Windsor Locks. Minutes from Golf course, and private fresh water lakes where you can see down 20 feet. Come enjoy The sunrise and sunsets on your land, Enjoy the Peace and PRIVACY you and your loved ones deserve. Copy and paste url. https://youtu.be/Z2J6NnBoxo0?si=AJnNb8rNRyzgDi_C

7 Stadler Hts, Winchester
$449,000
5 Beds ⋅ 4 Baths ⋅ 24071827 MLS
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 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

55 Walnut St, Winchester

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.