Winsted Homes under $750,000

Welcome to Winsted, a charming neighborhood nestled in the heart of Winchester, Connecticut, within the picturesque Litchfield County. Known for its rich history and vibrant community spirit, Winsted offers an inviting atmosphere that seamlessly blends small-town charm with modern conveniences.

As you stroll through the tree-lined streets, you’ll discover a diverse array of homes that cater to various lifestyles, with many properties available for under $750,000. Whether you’re a first-time homebuyer, a growing family, or looking to downsize, Winsted has something for everyone. From cozy bungalows and classic Victorian homes to contemporary residences, the real estate market here presents an excellent opportunity to find your dream home without breaking the bank.

Winsted is not just about beautiful homes; it’s about community. Residents enjoy access to local parks, recreational facilities, and a vibrant downtown area filled with quaint shops, delicious eateries, and cultural events. The nearby Highland Lake offers a perfect spot for summer activities, while nearby hiking trails provide year-round outdoor adventures.

Families appreciate the quality education provided by the local school system, making Winsted an ideal place to raise children. With its friendly atmosphere, rich history, and an array of affordable housing options, Winsted is truly a gem in Litchfield County. Come explore this delightful neighborhood and discover why so many are proud to call Winsted home!

Newest Winsted Homes under $750,000

$300,000

4 Beds ⋅ 3 Baths ⋅ 24210637 MLS

Valued by Redfin at $497,000 and Realtor at $516,000 - this house is a gem! Welcome to 205 Perch Rock Trail, a spacious 4-bedroom, 2.5-bath home in the highly desirable Highland Lake area of Winsted. Offering an incredible combination of space, location, and value, this property is a rare opportunity for a buyer looking to create something special. The home needs renovations and is being sold As Is, but the potential is substantial.The home offers approximately 2,369 square feet of living space, including a finished lower level with a kitchenette and full bath - ideal for an in-law setup, guest suite, home office, recreation space, or extended-family living. Enjoy lake views, nearby water access, a private backyard, two fireplaces, a balcony, generous storage, and an under-house garage. Public water and public sewer. With 4 bedrooms, multiple living areas, and flexible lower-level space, the possibilities here are exceptional. Whether you are looking for a year-round residence, weekend lake retreat, renovation opportunity, or investment property, 205 Perch Rock Trail offers tremendous upside. Bring your vision and make this Highland Lake gem your own!

205 Perch Rock Trl, Winchester

$239,900

3 Beds ⋅ 1 Baths ⋅ 24210294 MLS

3 bedroom home offering comfortable living with the convenience of gas heat as well as a wood stove and main level laundry. The layout provides plenty of space for everyday living, relaxing, and entertaining. Enjoy Highland Lake with Resha Beach just a half mile away, perfect for summer days by the water. A short drive takes you to the nearby boat launch, making it easy to enjoy boating, fishing, and all that the area's lakes have to offer.

35 Prospect St, Winchester

$289,900

4 Beds ⋅ 2 Baths ⋅ 24210073 MLS

Welcome to this charming 4-bedroom, 1.5 bath home in Winsted, where classic character meets comfortable everyday living. Built in 1927, this well-maintained home features beautiful hardwood floors, original woodwork, detailed trim, and spacious rooms filled with natural light. The main level offers generous living and dining spaces while the bright kitchen features ample cabinetry, stainless steel appliances, and plenty of counter space. A convenient half bath completes the main level. Upstairs, you'll find four well sized bedrooms, a full bath, and additional built-in storage, along with preserved woodwork and charm throughout. This property offers a private yard with mature trees and established landscaping, providing a nice outdoor space to enjoy. A wonderful opportunity to own a character-filled home with space, charm, and comfort in the heart of Winsted!

173 Gilbert Ave, Winchester

$339,900

3 Beds ⋅ 1 Baths ⋅ 24210012 MLS

Lovingly maintained by the same family since it was built in 1949, this 3-bedroom Colonial offers approximately 1,500 sq. ft. of living space on a 1-acre lot on the outskirts of town, yet within walking distance to the beach at Highland Lake. The main level features a spacious living room, large kitchen, dining room, full bath and inviting 3-season porch. Upstairs are three comfortable bedrooms with ample closet space. Hardwood floors run throughout the home, adding to its classic charm. Energy-conscious features include three heating sources: an oil-fired boiler, pellet stove in the living room and a magnificent soapstone wood stove in the lower level. The home also offers plenty of insulation, thermopane windows and a roof installed in 2021. Outside, you'll find excellent garage and storage space, including a large barn/garage with room for vehicles and a workshop, plus an additional detached garage. Set on nearly an acre with convenient access to Highland Lake and town amenities, this well-cared-for home is ready for its next chapter. This one is worth seeing!

50 Overlook Rd, Winchester

$575,000

14 Beds ⋅ 12 Baths ⋅ 24209933 MLS

99 High St, Winsted, CT 06098 is a multi family residential property. The Building was built in 1958 and includes 4 units as well as a garage for multi purpose storage warehouse use. It has a large swing up garage door for excellent storage. There is also a small office with an interior bathroom. 1 unit is a 2 bedroom 1.5 bath. 3 units are a 1 bedroom, 1 bath. Each unit is rented with a stable long term paying tenant. The garage is also rented to a long term tenant. The driveway parking area was recently redone with new concrete for parking access. The exterior was recently painted and has been well maintained, a new furnace has been added as well, 3 of the 4 units have been updated.

99 High St, Winchester

$449,000

3 Beds ⋅ 3 Baths ⋅ 24208283 MLS

Enjoy lake living with this inviting 3 bedroom, two and a half bath home located directly across the street from Highland Lake. Offering water views and a convenient location, this property is a wonderful opportunity for a year round residence or weekend getaway. The home features a two car garage and plenty of parking and storage. Enjoy the convenience of having two beaches and a boat launch within walking distance, making it easy to spend your days swimming, boating, fishing, or simply relaxing by the water. Come take a look!

150 E Lake St, Winchester

$425,000

3 Beds ⋅ 2 Baths ⋅ 24198146 MLS

Situated on a side street just outside the town, this contemporary 3-bedroom residence exudes an open and spacious ambiance, enhanced by vaulted ceilings that impart a sense of grandeur to the living room. The home features numerous updates, including a stunning kitchen, two living areas, a separate dining space, and two decks accessible from both the dining and living rooms. The first-floor laundry room is convenient and adjacent to the half bath. The upper level comprises three bedrooms and a full bath. Additionally, a finished lower level and an attached garage complete this home's layout. This Winchester property offers a private yard and a convenient location, placing you in the heart of Litchfield County.

120 Moore Ave, Winchester

$350,000

4 Beds ⋅ 2 Baths ⋅ 24207462 MLS

3.7-acre property offering a 4-bedroom, 2-bath Cape with plenty of room and flexibility. Formerly operated as a small farm, the property provides space for gardening, animals, recreation, or other uses. The first floor features an open floor plan with impressive 10-foot ceilings and a layout that can adapt to a variety of needs. Four bedrooms provide room for family, guests, or a home office. A unique opportunity for buyers looking for acreage, space, and the ability to make a property their own.

100 Norfolk Rd, Winchester

$595,900

8 Beds ⋅ 5 Baths ⋅ 24200869 MLS

One of the finest grand classic Colonial homes where timeless charm and beautiful details can still be found throughout. Features include elegant crown molding, rich wood paneling, wide baseboard molding, gleaming hardwood floors, and a sweeping grand staircase-all adding to the warmth and character of this truly special home. This home features formal dining room, sitting room with fireplace, remolded kitchen offering two sinks, granite counter large palladium windows allowing in natural light a main floor study with fireplace /built in bookshelves. On second floor are 6 bedrooms and 3 full baths, primary bedroom has unique alcove with sink /dressing area. Vintage Blue stone patio is for quiet times to enjoy watching the wildlife, or you can play a game of billiards on the standard size table in the game room. Only three families have lived in this elegant 101 year young home. A home filled with elegance, history and warmth All this elegance can be yours. Wonderful home for extended family or possible Bed & Breakfast. There is many possibilities with this property. Minutes from Rt 8, easy drive to Bradley Airport, enjoy recreation at Highland lake.

143 Holabird Ave, Winchester

$749,900

3 Beds ⋅ 2 Baths ⋅ 24206406 MLS

Highest and best offer by noon on Monday 21st. Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with quality finishes and thoughtful attention to detail throughout. Step inside to a bright, inviting interior filled with natural light from newer Andersen windows and doors. The beautifully renovated kitchen features modern appliances, sleek countertops, abundant cabinetry, and an open, welcoming feel that's perfect for entertaining after a day on the lake. Both full bathrooms have been tastefully remodeled, while LifeProof luxury plank flooring provides durability and easy maintenance. Enjoy year-round comfort with updated heating and central air conditioning. Outside is where this property truly shines! A newer deck and patio overlook Highland Lake, creating the perfect setting for morning coffee, summer dinners, sunsets, and unforgettable gatherings with family and friends. Step outside and enjoy direct access to one of Connecticut's most beautiful recreational lakes. Whether you're searching for a primary residence, weekend escape, or spectacular AirBnB, 180 Shore Dr delivers the lifestyle, location, and views that make waterfront ownership so special.

180 Shore Dr, Winchester

$439,900

4 Beds ⋅ 2 Baths ⋅ 24202969 MLS

Welcome to 136 Losaw Rd! Built in 1984, this nicely maintained and updated home offers 1,977 sq. ft. of living space with 4 bedrooms, 2 full baths, and a comfortable open floor plan, all set on 1.76 acres. The main living level features an open dining area and kitchen with breakfast bar overlooking the sunken living room, highlighted by a beautiful arched fieldstone fireplace with propane log set. Two modest-sized bedrooms and a full bath complete this level. Upstairs, you'll find two generously sized bedrooms, a second full bath, and a large storage closet. The lower level features a fieldstone hearth and approximately 400 sq. ft. of additional space ready to be finished to suit your needs. Outside, the property offers a two-stall horse barn with additional room for hay and storage, adding great versatility for equestrian use, hobbies, or additional storage. Nicely maintained and thoughtfully updated over the years, this property offers plenty of space both inside and out. Don't let this one slip away!

136 Losaw Rd, Winchester

$325,000

4 Beds ⋅ 3 Baths ⋅ 24199882 MLS

Investment Opportunity! Well-maintained two-family house offering the ideal combination of functionality and income potential. Each unit features 5 rooms, including 2 bedrooms and 1 full bath. Enjoy the benefits of a convenient downtown location, close to schools, shopping, dining, and everyday conveniences. Both units are currently rented, making this property a strong choice for investors seeking steady cash flow.

48 Center St, Winchester

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