Thomaston Real Estate

Welcome to Thomaston, a charming town nestled in Litchfield County, Connecticut. With a rich history dating back to the early 19th century, Thomaston offers a perfect blend of small-town charm and modern amenities.

Known for its picturesque Main Street lined with historic buildings and locally-owned shops, Thomaston is a tight-knit community where neighbors become friends and visitors are always welcomed with open arms. The town's vibrant arts scene, including galleries and studios, adds to its unique character and provides residents with a creative outlet to explore.

Nature enthusiasts will appreciate Thomaston's proximity to outdoor recreational opportunities, with numerous parks, hiking trails, and scenic overlooks just a short drive away. The town's location along the Naugatuck River also offers fishing and boating opportunities for those looking to connect with nature.

Families are drawn to Thomaston for its top-rated schools and safe, family-friendly neighborhoods. With community events and festivals held throughout the year, there is always something happening in town to bring residents together and create lasting memories.

Whether you're looking to settle down in a peaceful New England town or simply explore all that Thomaston has to offer, this quaint town is sure to capture your heart. Come and discover the beauty and charm of Thomaston, Connecticut.

Newest Listings in Thomaston

$250,000

2 Beds ⋅ 2 Baths ⋅ 24206195 MLS ⋅ Black Rock Village BLDG.

Beautifully maintained 2-bedroom, 1.1-bath condo in the desirable Black Rock Village community. The open first floor offers a spacious kitchen, living room, and dining area, plus a half bath, storage closet, and attached 1-car garage. Upstairs are two generously sized bedrooms with ample closet space, a full bath with tub/shower, and a separate laundry room. A well-designed floor plan with plenty of storage and convenient features throughout.

203 Branch Rd Unit 1C, Thomaston

$350,000

3 Beds ⋅ 1 Baths ⋅ 24176924 MLS

One level living in this 6 room home. Living room and all bedrooms have hardwood flooring. Applianced kitchen w/ separate dining area. Remodeled bath w/ heated floors. Walk up attic for easy storage. One car garage under the house and a 2 car garage detached wired for electricity. Large yard for a garden area or entertaining. Being sold as.

129 Atwood Rd, Thomaston

$299,900

3 Beds ⋅ 1 Baths ⋅ 24203649 MLS

Historic charm with convenient updates and a peaceful setting. Built in the 1850s, this well maintained home offers a blend of historic character and practical updates. The first floor features wood flooring and brightly enclosed front porch that provides a welcoming space to relax and enjoy the seasons. The home offers three bedrooms upstairs. Recent improvements include an energy efficient boiler installed in 2017, and a drilled well completed in 2015. The property also includes a newer asphalt driveway and garage, with an attached shed, providing excellent storage and workspace, built in 2023. Enjoy the peaceful backyard setting, complete with a patio with a motorized awning and a brook along the rear of the property. Convenient located near Route 8, the home offers easy access to nearby town amenities. The property is served by natural gas and has passed a recent septic inspection, offering added peace of mind. An excellent opportunity to own a home with character, practical updates, and a convenient location.

229 Jackson St, Thomaston

$499,900

3 Beds ⋅ 3 Baths ⋅ 24199076 MLS

Welcome to 459 Bayberry Dr. Thomaston, CT. Located in quiet area of fine homes, you'll find this Large contemporary 3 bedroom, 2.1 bath home situated on 1.0 level acres. Upon entry you'll fall in Love with the oversized living room offering vaulted ceiling and open flow directly into the formal dining room - Perfect for large gatherings and conversations between friends. The fully appliance kitchen offers stainless steel appliances, tile floor and plenty of cabinetry space for all your cooking needs! Also on the first floor is the Kitchen eating area, Den with Fireplace and hearth, first floor laundry room AND LARGE Family room with vaulted ceiling. Could also be Office OR possible in-law bedroom! French door off kitchen opens to rear deck overlooking level rear yard abutting woods. Perfect place for peace and quiet. Walk down the street to Thomaston's own Nystroms Park and enjoy a game of tennis, a jog on the professional track or a swim. Or relax all day while kayaking on Nystroms pond. Home offers NEW Central Air. Generator Hook Up. 2 car garage, front patio.

459 Bayberry Dr, Thomaston

$499,000

3 Beds ⋅ 3 Baths ⋅ 24198007 MLS

Move right into this Beautifully Maintained Colonial! Main Level offers a Large Livingroom, Dining Room and Kitchen with half bath. Slider doors off of the kitchen lead you to a New Deck overlooking the back yard. Second Level has a Master Bedroom with walk-in closet and Full Bath. There are 2 additional Bedrooms and another Full Bath on the Second Level. Full Basement with washer dryer hook-ups and walkout door to back yard. Immaculate 2 Car Garage.

587 High Street Ext, Thomaston

$239,900

1 Beds ⋅ 1 Baths ⋅ 24198969 MLS

Remodeled one-bedroom home set on a quiet lot in Thomaston. Updates include a new kitchen with granite countertops, a remodeled bathroom, new flooring throughout, and fresh interior paint. The property sits on a nice-sized lot surrounded by trees and natural scenery, giving it a peaceful, almost nature-preserve feel. Located in a quiet neighborhood with a comfortable amount of privacy, this is a simple, move-in-ready home with a lot of character and a great setting. A few finishing touches and minor items are still in the process of being completed. Seller is also providing a $2,000 credit toward the purchase of a new refrigerator and stove.

786 High St Ext, Thomaston

$289,900

3 Beds ⋅ 1 Baths ⋅ 24197533 MLS

Welcome to 99 Pine Hill Road, a welcoming 3-bedroom, 1-bath cape offering a thoughtfully updated interior and plenty of additional living space. Recent improvements include new stainless steel appliances, fresh neutral paint colors, new vinyl flooring, and a fully renovated bathroom, giving the home a fresh, move-in-ready feel. The lower level features approximately 900 SF of finished space, providing excellent flexibility for a family room, home office, recreation area, or additional living space. Updated mechanicals include an efficient tankless COMBI boiler providing heat and hot water. Outside, the lightly wooded backyard offers a comfortable sense of privacy, while the generously sized driveway provides ample off-street parking. Conveniently located near Black Rock State Park for hiking, swimming, and outdoor recreation, with easy access to major highways for commuting and everyday conveniences. A great opportunity for first-time buyers seeking an updated, well-maintained home in a desirable Thomaston location.

99 Pine Hill Rd, Thomaston

$249,900

2 Beds ⋅ 1 Baths ⋅ 24197496 MLS

Charming home offering comfortable living with practical updates throughout. The second floor features two bedrooms and a full bathroom, with the added convenience of a washer and dryer located within the bathroom area. Newer laminate flooring extends throughout the home, creating a clean and cohesive look. Enjoy efficient natural gas heat and hot water, along with the peace of mind that comes from a roof that is only two years old. The basement offers additional usable space with laminate flooring already installed and the beginnings of finishing work, including drywall, providing potential for a variety of uses. A walkout basement provides direct access to the backyard via a concrete and block pathway, adding convenience and functionality to the space. Outside, you'll find a spacious backyard perfect for outdoor enjoyment, a rear wood deck for relaxing or entertaining, and a storage shed for tools and seasonal items. The paved driveway provides off-street parking for up to three vehicles. Conveniently located near Thomaston's shops, restaurants, parks, and local amenities, this property offers an excellent opportunity for homeowners seeking affordability, efficiency, and room to enjoy both indoors and out. **Audio and video recording devices may be in use**

226 N Main St, Thomaston

$549,900

3 Beds ⋅ 3 Baths ⋅ 24196202 MLS ⋅ Whispering Pines Village BLDG.

Welcome to this beautifully maintained highly desirable 55+condominium community in the heart of Litchfield County. Offering an exceptional blend of comfort, style, and functionality. The open-concept floor plan is highlighted by oak hardwood floors on the main level, soaring cathedral and tray ceilings, fireplace, two interior balconies, elegant crown moldings, recessed lighting, paddle fans, and custom plantation shutters, creating a bright and inviting living space. The main level features primary bedroom suite with well-appointed full bath with a relaxing Jacuzzi tub. The professionally designed kitchen flows seamlessly to the living area together, making the home ideal for both everyday living and entertaining. Upstairs, you'll find a private third bedroom along with a versatile den or home office featuring skylights, perfect for working from home, reading, or enjoying a quiet retreat. Outdoor living is equally impressive with a charming back porch complete with a retractable awning, and a professional irrigation system that keeps the landscaping looking its best. Additional features include a security system, an attached two-car garage. A spacious partially finished basement with potential for a large family room or fitness area. This move-in-ready condo combines quality craftsmanship, generous living space, and desirable amenities in a peaceful yet convenient location. Low condo fees. A remarkable property guaranteed to exceed your expectations!

1 Stevens Blvd Unit 1, Thomaston

$229,900

3 Baths ⋅ 24196413 MLS

Value-Add Mixed-Use Investment Opportunity in GC zone! Prime high-visibility location on heavily traveled East Main Street offering outstanding redevelopment and income-producing potential. This mixed-use property has been a long-standing neighborhood landmark, with the main level operating as a successful bar for decades. Continue its existing use or reimagine the space as a restaurant, cafe, retail storefront, office, professional services, or other commercial venture (subject to local approvals). The second floor has historically operated as a rooming house consisting of 5 rentable rooms with shared kitchen, living room, and bathroom facilities, presenting the opportunity to restore rental income or explore alternative residential configurations where permitted. Property requires extensive renovation but some improvements have already been completed, including a newer roof and two newer gas furnaces. Ideal for investors, developers, or owner-operators seeking to unlock the property's full potential through renovation and repositioning. Endless possibilities for redevelopment, value creation, and future cash flow. Easy on/ off from Route 8, only minutes to I-84, Metro-North Train station in Waterbury, 45 mins from Danbury and 2 hours from NYC. Sold strictly "AS IS, WHERE IS." Cash offers preferred. Opportunities like this don't come along often, so schedule your showing and act quickly!

117 E Main St, Thomaston

$337,900

3 Beds ⋅ 2 Baths ⋅ 24192764 MLS

Wonderful split level home with 3 bedrooms, 1 1/2 bathrooms located in one of the most desirable areas. The heart of the home features a bright kitchen with granite countertops leading to a spacious deck overlooking the backyard. Spacious living areas and a basement fit for extra living space, family room, home office, play room or gym. The possibilities are endless. Step outside to your own private backyard, ideal for entertaining, summer barbecues, or simply relaxing in a peaceful setting. With generous sized bedrooms, an ideal layout for everyday living and a location close to shopping, restaurants, schools, park and major highways, this home truly checks all the boxes.

98 Edgewood Ave, Thomaston

$599,900

5 Beds ⋅ 2 Baths ⋅ 24191874 MLS

Welcome to 220 Jackson Street. This is a beautifully renovated home with an in-law suite. This spacious property offers an exceptional opportunity for generational living, investors and owner-occupants. Originally built in 1845, the home blends timeless character with modern updates and features two well-designed living areas, generous living space, and a large 1.8-acre lot. This versatile property offers endless possibilities in a convenient Thomaston location.

220 Jackson St, Thomaston

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