Homes for Sale near Pearson School

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  /38

  $1,295,000

  • 3 Beds
  • 3 Baths
  • 2,420 Sq Ft

  722 Lake Dr, Winsted, CT 06098

  Welcome to lake living at its finest! Built in 2014 and first time on the market. Impeccably maintained, this stunning three bedroom, 3 bath home on Highland Lake, Winchester offers the perfect blend of comfort, style, and breathtaking VIEWS! From the moment you enter you will be captivated by the open-concept design, high-end finishes and panoramic lake views from both inside and out. Enjoy

  Joanne Donne The Washington Agency

  722 Lake Dr, Winsted, CT 06098
• 

  Explore Pearson School

• 

  

  

  /40

  $799,000

  • 5 Beds
  • 2.5 Baths
  • 2,950 Sq Ft

  151 Losaw Rd, Winsted, CT 06098

  Feel worlds away while being less than 2 miles to town amenities in this like-new retreat nestled on an expansive 11.59-acre lot. This property is your personal sanctuary, complete with private trails for hiking your own land. The eat-in-kitchen is well-equipped with ample cooking space, seamlessly connected to the formal dining room and open to living space, and leads out to the large deck with

  Breanna Goebel Compass Connecticut, LLC

  151 Losaw Rd, Winsted, CT 06098
• 

  

  

  /34

  $625,000

  • 5 Beds
  • 3 Baths
  • 3,404 Sq Ft

  441 Platt Hill Rd, Winsted, CT 06098

  Welcome to 441 Platt Hill Road - a home that offers warmth, charm, and plenty of space to make memories. This inviting residence features an open and airy layout filled with natural light thanks to large windows and multiple skylights. Solid hardwood floors and tile run throughout the main level, creating a timeless foundation for your personal touch. The spacious eat-in kitchen, while vintage in

  David Sartirana Northwest CT Realty

  441 Platt Hill Rd, Winsted, CT 06098
• 

  

  

  /27

  $449,900

  • 4 Beds
  • 1.5 Baths
  • 2,239 Sq Ft

  51 Pratt St, Winsted, CT 06098

  This stunning Renovated home is perfectly situated in the beautiful town of Winsted could be yours! Just a leisurely walk from the beautiful Highland Lake. Offering more than 2,200 square feet of thoughtfully designed living space, this home blends timeless charm with modern updates. The bright and spacious kitchen opens effortlessly into a welcoming dining area and a cozy yet expansive living

  Arlene Gonzalez The Gonzalez Property Group

  51 Pratt St, Winsted, CT 06098
• 

  

  

  /39

  $779,900

  • 3 Beds
  • 3.5 Baths
  • 4,953 Sq Ft

  111 South Rd, Winsted, CT 06098

  Perched up higher than the rest with sweeping views up a private driveway in beautiful Winchester Center you'll find this custom built 4,953 sq ft Colonial nestled in on 3.97 serene & bucolic acres. For the car enthusiasts, you'll see a 3 bay garage that can fit up to at least 7 cars if lifts are installed including a bonus 2 car tandem garage within the 3 bays. Plenty of room for oversized

  Dawn Rousseau Showcase Realty, Inc.

  111 South Rd, Winsted, CT 06098
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  /35

  $450,000

  • 3 Beds
  • 3 Baths
  • 2,747 Sq Ft

  117 South Rd, Winsted, CT 06098

  Nestled in a peaceful rural setting of Winchester Center, this charming home offers a perfect blend of rustic character and modern convenience. The property is located on over 3.3 acres of land and is adjacent to a scenic pond. Inside you will find a three bedroom two bath home with an additional in law apartment with one full bath and one bedroom and its own private entrance. The home also

  Christina Niziolek William Raveis Real Estate

  117 South Rd, Winsted, CT 06098
• 

  

  /35

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  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, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
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  /37

  $515,000

  • 5 Beds
  • 4 Baths
  • 5,016 Sq Ft

  55 Walnut St, Winsted, CT 06098

  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

  David Sartirana Northwest CT Realty

  55 Walnut St, Winsted, CT 06098
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  /36

  $499,000 Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,892 Sq Ft

  819 E Wakefield Blvd, Winsted, CT 06098

  Perched directly across the street from Highland Lake's 3rd Bay, this charming 1,900 sq. ft. Cape offers sweeping lake views and the enjoyment of a permanent right-of-way to access the water. The home features 7 rooms, including 3 bedrooms and 1.5 baths, and has been thoughtfully maintained with important updates: new propane heating and hot water systems (2022), a new roof on both the house and

  David Sartirana Northwest CT Realty

  819 E Wakefield Blvd, Winsted, CT 06098
• 

  

  /29

  $225,000

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  210 Walnut St, Winsted, CT 06098

  Discover the potential in this raised ranch located in beautiful Winsted, CT! Featuring 3 bedrooms and 1.5 bathrooms, this home offers a functional layout and a great opportunity to bring your vision to life. An attached two-car garage adds everyday convenience and plenty of storage. Set on a nice lot, the property is close to town amenities, schools, and outdoor recreation that make Winsted

  Nicole Araujo Trend 2000 Real Estate

  210 Walnut St, Winsted, CT 06098
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  /21

  $150,000

  • 1 Bed
  • 1 Bath
  • 635 Sq Ft

  38 Riveredge Dr Unit 38, Winsted, CT 06098

  End Unit Ranch-Style Condo - Winchester. Discover privacy and convenience in this well-maintained one-level end unit nestled in the foothills of the Berkshire Mountains. Offering an open-concept layout, this ranch-style condo features a spacious living room, dining area, kitchen, large bedroom, full bathroom with in-unit laundry, & excellent closet space. While the condo would benefit from

  Suzie Larson Turning Point Realty, LLC

  38 Riveredge Dr Unit 38, Winsted, CT 06098
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  /31

  $350,000

  • 6 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  157 Elm St, Winsted, CT 06098

  Victorian Charm Meets Modern Potential - 5-Bedroom Home Across from Pearson School Step into timeless elegance with this spacious 5-bedroom, 2.1-bath Victorian-style home located directly across from Pearson School in Winsted. Featuring hardwood floors throughout and a beautifully updated kitchen, this property blends classic character with modern convenience. From its distinctive architectural

  Doreen Gagnon Coldwell Banker Realty

  157 Elm St, Winsted, CT 06098
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  /40

  $355,750

  • 3 Beds
  • 1.5 Baths
  • 1,833 Sq Ft

  126 Forest Ave, Winsted, CT 06098

  Charming Cape 2 minutes to Highland Lake. Welcome to this one owner, 3 bedroom, two bath Cape Cod home offering over 1,800 sq. ft. of living space on nearly one acre of land. Owned by the original family. This property has been lovingly maintained and thoughtfully update. Step inside to find a fully appliance kitchen, fresh carpeting, and updated windows and gutters. The flexible seven- room

  Joanne Donne The Washington Agency

  126 Forest Ave, Winsted, CT 06098
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  /8

  $389,000

  • Land
  • 20.87 Acres
  • $18,639 per Acre

  7 Stadler Heights, Winsted, CT 06098

  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

  Hector Ortiz KW Legacy Partners

  7 Stadler Heights, Winsted, CT 06098
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  /38

  $375,000 Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,584 Sq Ft

  111 Old Rd N, Winchester, CT 06098

  Two parcels for the price of one! Discover this beautifully maintained split-level ranch at 111 Old North Road in Winchester, offered together with the adjoining already-subdivided 2.5-acre buildable lot at 113 Old North Road. Enjoy the home as-is or explore the endless possibilities-build an in-law house, sell the lot, or develop it as an investment. Inside, the home features a unique layout

  Christopher Clarke Coldwell Banker Realty

  111 Old Rd N, Winchester, CT 06098
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  /27

  $399,900

  • 2 Beds
  • 1.5 Baths
  • 1,440 Sq Ft

  212 Spencer Hill Rd, Winsted, CT 06098

  Welcome to your peaceful retreat in the heart of Winchester - a quiet, scenic town surrounded by natural beauty. Tucked away on a private lot, this thoughtfully maintained home offers a perfect blend of rustic charm and modern comfort, with every detail designed to enhance your connection to the outdoors. Step inside to discover gleaming original hardwood floors that stretch across the sun-filled

  Tammy Powling Coldwell Banker Realty

  212 Spencer Hill Rd, Winsted, CT 06098
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  /23

  $197,500

  • 2 Beds
  • 1.5 Baths
  • 1,204 Sq Ft

  111 Riverton Rd Unit 37, Winsted, CT 06098

  Picture yourselves in this bright, roomy end unit condominium with room to spare! Totally renovated bathtub and fixtures in the full bath. Lovely, updated kitchen that not only has a pantry but sliding glass doors that lead out to the brand-new deck. 3-year-old pellet stove that will keep your entire unit toasty all winter long. The living room features beautiful sliding glass doors that also

  Sandra Marchetti The Washington Agency

  111 Riverton Rd Unit 37, Winsted, CT 06098
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  /13

  $199,900

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  14 Curtice St, Winsted, CT 06098

  Attention investors and buyers looking to build equity! Welcome to 14 Curtice Street, a home has incredible value and potential in the heart of Winsted. This 3-bedroom, 1-bath home features approximately 1,248 square feet of living space and is ideal for sweat-equity seekers or rehab-minded buyers. Exterior updates have already been completed, including a newer roof, siding, and windows, giving

  Michael Johnson Lock and Key Realty, Inc

  14 Curtice St, Winsted, CT 06098
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  /33

  $380,000

  • 3 Beds
  • 2 Baths
  • 2,024 Sq Ft

  166 Torringford St, Winsted, CT 06098

  Nothing to do but move right in to this meticulous colonial farmhouse nestled in the Litchfield Hills. This unique home combines a tasteful modern style mixed with rustic charm. Inside the fully renovated home offers a sprawling kitchen with ample counter and cabinet space, a breakfast bar with elegant quartz countertops and newer stainless steel appliances. The space is open to the dining area

  Lana Van Valkenburgh Vision Real Estate

  166 Torringford St, Winsted, CT 06098
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  /13

  $179,900

  • 3 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  14 Pratt St, Winsted, CT 06098

  Don't let the outside fool you! Perfect alternative to condominium living! No HOA and plenty of off street parking at this in-town location. Nice size living room; large kitchen/dining combination with access to the deck and the 1/2 bath laundry room make up the first floor of this cute home. Upstairs you will find 2 modest size bedrooms along with the large primary and the full bath which has a

  Amy Sartirana Northwest CT Realty

  14 Pratt St, Winsted, CT 06098
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  /40

  $1,149,000

  • 3 Beds
  • 3 Baths
  • 2,097 Sq Ft

  674 E Wakefield Blvd, Winsted, CT 06098

  Experience premier waterfront living on Highland Lake in this beautifully maintained 3-bedroom, 3-bath home offering stunning panoramic lake views and direct water access. Situated in the desirable 3rd Bay, this property boasts a private dock-perfect for boating, swimming, and enjoying all the lake lifestyle has to offer. Inside, you'll find an open and inviting layout with a spacious living

  Patrick Smith Smith & DeGroat Real Estate

  674 E Wakefield Blvd, Winsted, CT 06098
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  /27

  $235,000 Open Sat 11AM - 1PM

  • 1 Bed
  • 2 Baths
  • 1,334 Sq Ft

  174 Wallens St Unit H1, Winsted, CT 06098

  Discover effortless living in this inviting home at the sought-after Clockmaker's Hill community. The thoughtfully designed open floor plan creates seamless flow from the spacious living room-anchored by a cozy gas fireplace-to the dedicated dining room, perfect for hosting friends and family. The sun-drenched kitchen features a convenient breakfast bar for casual dining and morning coffee. The

  Kim D'Andrea William Pitt Sotheby's Int'l

  174 Wallens St Unit H1, Winsted, CT 06098
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  /20

  $255,000

  • 3 Beds
  • 1 Bath
  • 1,334 Sq Ft

  22 Curtice St, Winsted, CT 06098

  Step into timeless elegance with this beautifully updated colonial-style home, where classic charm meets modern convenience. Gleaming hardwood floors flow seamlessly throughout the main living areas, creating a warm and inviting atmosphere. The fully renovated kitchen is a chef's dream, featuring premium finishes, sleek countertops, and top-of-the-line appliances. Upstairs, you'll find spacious

  Terence Dominick Complete Real Estate

  22 Curtice St, Winsted, CT 06098
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  /10

  $225,000

  • 2 Beds
  • 1 Bath
  • 768 Sq Ft

  130 Stanton Ave, Winsted, CT 06098

  Step right into effortless living with this charming 2bedroom ranch-style home, nestled right in town and wrapped in durable, lowmaintenance vinyl siding. As you approach, you'll appreciate the tidy curb appeal and generous driveway-perfect for guests or extra vehicles. Inside, an open concept living and dining area welcomes you with abundant natural light and easy flow, ideal for both everyday

  David D'Amore Northwest CT Realty

  130 Stanton Ave, Winsted, CT 06098
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  /14

  $214,900

  • 3 Beds
  • 1 Bath
  • 980 Sq Ft

  99 Norfolk Rd, Winsted, CT 06098

  99 Norfolk Rd, Winsted CT - Opportunity Knocks! This cute 3-bedroom Cape sits proudly on 1.3 acres and is ready for its next chapter! With vinyl siding, replacement windows, and a lovely setting perched high up from the road, the bones are here-now it just needs your vision. For those seeking an investment opportunity or ready to roll up their sleeves and bring this gem back to life, this could

  Lisa McCarthy Coldwell Banker Realty

  99 Norfolk Rd, Winsted, CT 06098
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  /36

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,736 Sq Ft

  38 Upland Rd, Winsted, CT 06098

  Estate Owned 3 to 4 Bedroom Colonial in Immaculate Move In Condition! Tucked away on a quiet street but within walking distance of Schools, Medical Facilities and Shopping. Special features include a huge cedar closet, Hardwood floors throughout the entire house, bay windows, 24' x 14' Family Room with Propane Gas Stove and an Oversized Full Bath The Master Bedroom features its own office.

  Holly Blinkoff Cohen Agency

  38 Upland Rd, Winsted, CT 06098
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  /4

  $250,000

  • Land
  • 15.9 Acres
  • $15,723 per Acre

  00 Chapel Rd, Winchester, CT 06098

  Look no further for A Very Private location to build your Dream Home?? On this Lot there is the Hilltop which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester may be the place for you. The access to the Rear lot is though 151 Chapel Rd. property.

  Linda Ganem Borla & Associates Real Estate

  00 Chapel Rd, Winchester, CT 06098
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  /26

  $1,200,000

  • Land
  • 65.29 Acres
  • $18,380 per Acre

  257 Torringford St, Winchester, CT 06098

  65+ Acre Property with infrastructure and natural features. Spanning over 65 acres, this private property is accessed via a 5,000 foot driveway and features a mix of open space and wooded terrain. The land is bordered by historic stone walls on both sides, adding character and clear boundary lines. Bonus: 14x40 horse barn, ready for livestock or storage. 24x32 building on a concrete slab,

  Sabrina Janco Century 21 Bay-Mar Realty

  257 Torringford St, Winchester, CT 06098
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  /4

  $39,000

  • Land
  • 0.41 Acre
  • $95,122 per Acre

  130 Alpha Ave, Winsted, CT 06098

  Discover the Perfect Canvas for Your Dream Home in Winchester, Connecticut! This exceptional .41-acre parcel (owner reports closer to .5 ac) combines eight contiguous lots to create a prime opportunity for building your ideal residence. Nestled in the serene surroundings of the Highland Lake neighborhood, the property is lightly wooded with mature, straight-standing hardwoods and features a

  Suzie Larson Turning Point Realty, LLC

  130 Alpha Ave, Winsted, CT 06098
• 

  /2

  $39,900

  • Land
  • 0.92 Acre
  • $43,370 per Acre

  256 Colebrook Rd, Winchester Center, CT 06098

  Just under an acre of land and over 100 feet of road frontage available on Colebrook Road!

  Austin Brochu Sullivan Real Estate Inc

  256 Colebrook Rd, Winchester Center, CT 06098
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  /39

  $995,000

  • 4 Beds
  • 2 Baths
  • 3,088 Sq Ft

  469 Platt Hill Rd, Winsted, CT 06098

  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,

  Marshall Cohen Cohen Agency

  469 Platt Hill Rd, Winsted, CT 06098
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  /34

  $749,900

  • 7 Beds
  • 3 Baths
  • 3,486 Sq Ft

  39 S Main St, Winsted, CT 06098

  THREE PROPERTIES ONE PRICE!!! Includes single family, multi family & additional lot totaling 4.36 acres. 1. 3500 sq ft 2 family home featuring 1800's architecture including massive period correct windows, wrap around porch, beautiful stone foundation, and detached 2 car garage. 5 bed, 2 1/2 bath main house with 2 bed, 1 bath attic apartment, freshly updated. Brand new whole house natural gas

  RYAN HORVAY Smith & DeGroat Real Estate

  39 S Main St, Winsted, CT 06098
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  /9

  $739,900

  • Land
  • 93.38 Acres
  • $7,924 per Acre

  0 Old Robertsville Rd, Winchester, CT 06098

  Nestled along a peaceful country road near the Colebrook and Barkhamsted town lines, this breathtaking 93.38-acre parcel embodies the timeless charm of rural New England. Once part of a cherished family farm, the land offers a harmonious blend of rolling meadows, majestic forests, and the gentle, winding presence of the Still River, which meanders through a substantial portion of the property.

  David Sartirana Northwest CT Realty

  0 Old Robertsville Rd, Winchester, CT 06098
• 

  

  /36

  $849,900

  • 4 Beds
  • 2 Baths
  • 1,781 Sq Ft

  119 W Wakefield Blvd, Winsted, CT 06098

  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, this beautifully renovated two-family home can be enjoyed as a single-family retreat or an income-generating

  Mela Veltri Case KW Legacy Partners

  119 W Wakefield Blvd, Winsted, CT 06098
• 

  /2

  $49,000

  • Land
  • 0.37 Acre
  • $132,432 per Acre

  99 Hubbard St, Winsted, CT 06098

  99 Hubbard St. - Private Lot Near Downtown & Highland Lake. Tucked away at the end of a quiet dead-end street, this .37-acre lot offers both privacy and convenience. While enjoying a peaceful setting, you're still just minutes from downtown with easy access to shopping, dining, and entertainment. Plus, Highland Lake is just a short distance away, providing endless opportunities for boating,

  David Sartirana Northwest CT Realty

  99 Hubbard St, Winsted, CT 06098
• 

  /2

  $29,000

  • Land
  • 0.44 Acre
  • $65,909 per Acre

  124 Rockwell St, Winsted, CT 06098

  124 Rockwell St. - Versatile .44-Acre Lot Near Downtown This .44-acre lot offers a prime location close to downtown with city water and sewer available in the street. The previous home sat at street level, while the majority of the lot slopes below, creating a unique landscape with plenty of potential. With a little imagination and the right site contractor, this property presents endless

  David Sartirana Northwest CT Realty

  124 Rockwell St, Winsted, CT 06098
• 

  

  /40

  $2,199,000

  • 9 Beds
  • 5.5 Baths
  • 7,000 Sq Ft

  431 W Wakefield Blvd, Winsted, CT 06098

  This waterfront estate at 431 W. Wakefield Blvd in Winchester, CT, is not just a home but the ultimate Highland Lake lifestyle. Imagine waking up each day to stunning lake views, with endless seasonal activities awaiting just beyond your doorstep. In the summer, dive into boating, jet skiing, swimming, and fishing right from your private dock, or simply unwind along the shoreline. As winter

  Lisa Ogren Berkshire Hathaway NE Prop.

  431 W Wakefield Blvd, Winsted, CT 06098
• 

  

  /5

  $158,000

  • Land
  • 1.18 Acres
  • $133,898 per Acre

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098

  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

  David D'Amore Northwest CT Realty

  843-845 (lots - 10A, E Wakefield Blvd, Winchester, CT 06098
• 

  

  /5

  $295,000

  • Land
  • 51 Acres
  • $5,784 per Acre

  393 Winchester Rd, Winsted, CT 06098

  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.

  Tom McGowan Elyse Harney Real Estate

  393 Winchester Rd, Winsted, CT 06098
• 

  /2

  $69,000

  • Land
  • 2 Acres
  • $34,500 per Acre

  503 N Main St, Winsted, CT 06098

  Prime Building Lot Near Downtown & Highland Lake-Discover the perfect setting for your dream home on this 2 acre lot at 503 N Main Street. The Property has over 500' of road frontage, permitted uses include; accessory residential uses, family day care home, farm, seasonal cottages, single family dwelling. The property offers a peaceful atmosphere while maintaining easy access to downtown

  Charles Albertario William Raveis Real Estate

  503 N Main St, Winsted, CT 06098

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