Winchester Homes under $400,000

Welcome to Winchester, Connecticut, a hidden gem nestled in the heart of Litchfield County. This charming town is known for its picturesque landscapes, rich history, and a welcoming community spirit that makes it a perfect place to call home. With its serene lakes, lush forests, and vibrant local culture, Winchester offers a unique blend of tranquility and adventure, making it an ideal setting for families, retirees, and everyone in between.

For those seeking affordable housing options, Winchester boasts a variety of homes under $400,000, providing an excellent opportunity for first-time buyers and seasoned investors alike. These homes range from quaint, historic properties to modern designs, ensuring that there’s something for everyone. Imagine waking up to the sound of chirping birds and sipping your morning coffee on a sunlit porch, all while being just a stone’s throw away from local parks, hiking trails, and charming shops.

Winchester is not just about beautiful homes; it also offers a strong sense of community with numerous events and activities throughout the year. From farmers' markets to seasonal festivals, there’s always something happening that brings residents together. Additionally, with easy access to major highways, commuting to nearby cities is a breeze, making it a convenient location for those who work in larger urban areas.

Explore the enchanting town of Winchester and discover your dream home today. With affordable options and a vibrant community, you’ll find that this quaint Connecticut town is not just a place to live, but a place to thrive.

Newest Winchester Homes under $400,000

$275,000

2 Beds ⋅ 2 Baths ⋅ 24212555 MLS ⋅ Clockmaker's Hill BLDG.

IMMACULATE, MOVE-IN READY 55+ CONDO IN CLOCKMAKER HILL! Welcome to 174 Wallens Street Unit 2C, where comfort, convenience, and beautifully updated one-level living come together in the highly desirable Clockmaker Hill 55+ community! From the moment you step inside, it is clear this home has been meticulously cared for and thoughtfully designed with today's lifestyle in mind. Light, Bright & Beautiful! An abundance of windows fills this home with natural sunlight, creating a warm and inviting atmosphere throughout. The open, thoughtfully designed floor plan offers effortless one-floor living with two generously sized bedrooms and two full bathrooms. The beautiful engineered hardwood flooring, elegant tray ceilings, updated finishes, and neutral decor create a sophisticated yet comfortable setting. The spacious living room features a cozy fireplace-perfect for relaxing on chilly evenings. The beautifully updated kitchen features granite countertops, updated appliances, and a brand-new dishwasher, making everyday living and entertaining a pleasure. The primary suite is exceptionally well designed, offering a generously sized walk-in closet and private attached full bathroom. The second bedroom is nicely proportioned and offers flexibility for guests, an office, or hobbies. Convenience is built right in to this condo! Enjoy direct interior access from the garage, making coming and going effortless in every season. The home also features a conveniently located washer

174 Wallens St Unit C2, Winchester

$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

$374,900

6 Beds ⋅ 3 Baths ⋅ 24207726 MLS

Opportunity and flexibility come together at 95 Williams Street in Winsted. Offering approximately 2,887 square feet of living space, this spacious multi-family property is currently configured as two generously sized units with plenty of room both inside and out. Set on a uniquely large .49-acre corner lot, the property offers an impressive amount of outdoor space and privacy-something rarely found with a multi-family home. The left-side unit features four bedrooms and two full baths, while the right-side unit offers three bedrooms and one full bath-providing a total of seven bedrooms and three full baths. Each unit also benefits from additional attic and basement storage, a feature that is always appreciated in a multi-family home. According to the property card, the home is classified as a three-family property. The two units on the left side were previously combined, creating the larger four-bedroom residence that exists today. A future owner may have the opportunity to separate the space again and restore the property to a three-unit configuration, subject to any required municipal approvals. Whether you're looking for an investment property, an owner-occupied multi-family with rental income, or a property with the potential for a future three-unit configuration, 95 Williams Street offers an unusual combination of space, versatility, privacy and possibilities that are increasingly hard to find. Property being sold AS IS, WHERE IS.

95 Williams 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

$260,000

3 Beds ⋅ 2 Baths ⋅ 24204964 MLS

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 this classic home. Enjoy your LARGE eat-in kitchen with laundry hook ups and plenty of natural lighting and ample amounts of storage. The home sits on a flat, level yard with a huge storage shed, perfect for outdoor gatherings, storage, gardening, and play. Multiple decks off the home create inviting spaces to relax and take in the surroundings. Located just moments from a local boat launch, this property is ideal for those who love recreational water access. You're also close to the town green, shops, and everyday conveniences, making this home the perfect blend of historic charm and modern lifestyle. Schedule to view today!!

118 Meadow St, Winchester

$299,900

5 Beds ⋅ 2 Baths ⋅ 24206151 MLS

Well-maintained two-family home offering excellent owner-occupant or investment potential. First-floor unit features 3 bedrooms, kitchen, and living room and is currently rented. Second-floor unit is vacant and offers 2 bedrooms, living room, and kitchen. Separate utilities and laundry for each unit. Full basement provides additional storage. Entire home has undergone lead remediation. Great opportunity to live in one unit while generating rental income.

18 Pratt St, Winchester

$289,000

2 Beds ⋅ 1 Baths ⋅ 24202928 MLS

Welcome to this relaxing seasonal cottage, situated high above road level and offering breathtaking panoramic views of the 444-acre Highland Lake. Enter through the oversized screened porch, where you can unwind with family or friends while taking in the beautiful perennial plantings and natural surroundings. This charming cottage features two bedrooms, a loft, one full bath, an open-concept kitchen, dining area, and living room. For your comfort, oil heat and a mini-split unit provide heat and air conditioning. Additionally, there's a rear deck area perfect for outdoor dining & grilling. An extra outdoor shower is available to refresh after spending time on the lake.

347 W Wakefield Blvd, Winchester

$304,900

2 Beds ⋅ 2 Baths ⋅ 24201785 MLS

Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features wide-plank wood flooring, a small dining area, and a walk-out porch leading to a Trex deck-perfect for enjoying the outdoors and water views. A small first-floor bedroom offers flexibility for guests, an office, or additional living space. Upstairs, the primary bedroom is generously sized to easily accommodate a king-size bed and features wood flooring and propane-fired baseboard heat. The second bedroom also offers wood flooring, a large closet, ceiling fan, two large windows, and propane-fired baseboard heat. The full bathroom includes a newer vanity, stall shower, and laminate tile flooring. Additional features include forced-air propane heating on the main level, window air-conditioning units, a carpeted stairway, and two off-street parking spaces. A boat launch on Highland Lake provides an exceptional opportunity to enjoy boating and waterfront recreation.Book a showing today. This property will not last!

325 E Wakefield Blvd, 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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