Woodstock Homes under $400,000

Welcome to Woodstock, Connecticut: a quaint New England town nestled in the picturesque Windham County. Known for its rich history, stunning landscapes, and tight-knit community, Woodstock offers a perfect blend of rural charm and modern conveniences. With its lush forests, serene lakes, and rolling hills, this town is a haven for nature lovers and outdoor enthusiasts. Whether you enjoy hiking, fishing, or simply taking in the beauty of the changing seasons, Woodstock has something for everyone.

One of the most appealing aspects of Woodstock is its diverse real estate market, particularly for those seeking homes under $400,000. Here, you can find a variety of charming properties that cater to different lifestyles. From cozy cottages tucked away in the woods to spacious family homes with sprawling yards, Woodstock's real estate options provide an inviting atmosphere for first-time buyers, growing families, and retirees alike.

The community is also known for its vibrant local culture, with farmers' markets, artisanal shops, and seasonal festivals that celebrate the town's heritage. The excellent schools and friendly neighbors create a welcoming environment that makes Woodstock feel like home.

Living in Woodstock means enjoying the tranquility of small-town life while still being within easy reach of larger cities like Hartford and Worcester. With affordable housing options and a strong sense of community, Woodstock is a hidden gem just waiting to be discovered. Come explore the possibilities and find your dream home in this enchanting Connecticut town!

Newest Woodstock Homes under $400,000

$369,000

3 Beds ⋅ 1 Baths ⋅ 24187880 MLS

A little charm, a lot of heart, and a location worth getting excited about! Nestled in Woodstock with deeded rights and beach access to highly sought-after Witches Woods Lake, this inviting 3-bedroom, 1-bath ranch offers comfort, warmth, and the ease of one-level living. The home has been lovingly maintained and thoughtfully updated, including a kitchen remodel in 2023 with new cabinets, appliances, and flooring, offering a fresh and functional space for everyday living. The spacious deck is a wonderful place to enjoy morning coffee, gather with friends, or simply unwind. Downstairs, the finished lower level offers a cozy rec room and dedicated office area, providing extra space to make your own. Improvements over the years include a roof in 2018, water heater in 2021, interior and exterior doors in 2023, and well tank and well cap in 2024. Filled with warmth, character, and pride of ownership, this inviting home is ready for its next chapter and someone new to make it their own.

1629 Rte 171, Woodstock

$339,900

4 Beds ⋅ 2 Baths ⋅ 24212685 MLS

What started as just a summer cottage has been transformed over the 50 years of ownership into a great lake view & access home. This home features over 1,700 sq. ft. on two floors, 4 total bedrooms along with 2 full bathrooms. The first floor has a large living room with pellet stove heating that satisfies the major of the heating needs. There is a good working space kitchen along with a rear sunroom/plant room/dining area. There are two bedrooms, a full bathroom with tub/shower along with the laundry on the main level. The second floor was a full addition years ago. There are two very good-sized bedrooms, a sitting area/den, along with an additional full bathroom. You will even find a second story open deck for enjoying nature. Home features a full walk-up attic with good access & storage. The basement, once just a small crawl space, was excavated out and a block foundation was installed. A propane warm air heating system, propane water heater, along with an additional chimney flue for woodstove can be found. Home has deeded access & lake rights to Lake Bungee and is just walking distance from private beaches and boat launches.

101 Beaver Dam Rd, Woodstock

$379,900

3 Beds ⋅ 2 Baths ⋅ 24211726 MLS

If you're looking for a place to be surrounded in all that nature has to offer, you'll want to call this home! This 3 bedroom, 2 bath, saltbox colonial is sited on a double lot, bordering Wyndham Land Trust. You'll love watching the deer and other wildlife from the 10'x20' deck. As a part of the private community of Lake Bunggee, you may also take a short stroll to the beaches to enjoy water rights and access. The lake is about 112 acres to enjoy boating, fishing, swimming and hiking areas. The light filled, open floor plan is perfect for entertaining; vaulted ceiling living room/dining area has hardwood flooring, an expansive wall of windows, and slider open to deck. Tiled kitchen has cozy breakfast bar and spacious walk-in pantry. 1st floor bedroom has ensuite bath with shower. 2nd floor primary also has ensuite bath with tub/shower unit and walk-in closet. Additional bedroom on second floor. Walk-out lower level has wood stove. Updates include newer hot water tank, septic system, and oil tank. Roof shingles 2015. Welcome Home!

35 Old Sawmill Rd, Woodstock

$379,000

3 Beds ⋅ 2 Baths ⋅ 24209276 MLS

Move in ready ranch offering updated one level living, a finished walkout basement, and a private, level yard, all in the desirable town of Woodstock! The open concept main floor features hardwood floors, abundant natural light, and an updated kitchen with upgraded cabinetry, countertops, center island, and eat-in area. The kitchen opens to the living room, creating an inviting space for everyday living and entertaining. Three spacious bedrooms and an updated full bath complete the first floor. The finished lower level adds flexible living space with an open layout, pellet stove, walkout access, half bath, and laundry room. This space is ideal for a family room, home office, recreation space, or guest area. Outside, enjoy the spacious deck overlooking the private yard, plus a storage shed. Set in a quiet Woodstock location with easy access to 395 and 84, this home is convenient to major routes and surrounding communities. An affordable opportunity to enjoy the charm of Woodstock with updates already in place. Nothing to do but move in!

1619 Rte 171, Woodstock

$339,900

3 Beds ⋅ 2 Baths ⋅ 24205731 MLS

WAKE UP TO THE LAKE AND LIVE THE LAKE LIFE! Welcome to 91 Beaver Dam Rd, where everyday living feels like a getaway. This inviting 3-bedroom, 2-bath home is ideally situated across the road from the beach, putting swimming, fishing, kayaking, and canoeing practically at your doorstep. Imagine starting your morning with a beautiful sunrise over the lake, enjoying your coffee, then heading out for a paddle or some of the area's great fishing. Take a leisurely walk along the quiet community roads, meet your neighbors, and enjoy the relaxed atmosphere of this wonderful lake neighborhood. Whether you're searching for a year-round home, a weekend escape, or a place where you and friends can gather and make lasting memories, this property offers the lifestyle you've been looking for. Spend your days on the water, enjoy peaceful evenings, and leave the hustle and bustle behind. This isn't just a home-it's an opportunity to own a piece of the lake lifestyle.

91 Beaver Dam Rd, Woodstock

$199,900

2 Beds ⋅ 1 Baths ⋅ 24201823 MLS ⋅ Fawn Ridge BLDG.

Welcome to this beautifully renovated 832 sq. ft. end-unit condo in Woodstock, CT, offering an inviting opportunity to trade renting for owning and start building equity of your own. Freshly updated with new paint and flooring, this home provides a clean, comfortable setting that's ready for you to make your own. As an end unit, the home offers added privacy and a desirable layout. Whether you're a first-time homebuyer ready to take the next step or simply looking for an affordable way to put your monthly housing toward ownership, this condo is a smart place to begin. Enjoy the simplicity of condo living while taking advantage of all that charming Woodstock has to offer. Why keep paying rent when you can start building something of your own? Come see how easy homeownership can be!

12 Fawn Rdg Unit 12, Woodstock

$289,900

2 Beds ⋅ 2 Baths ⋅ 24198944 MLS ⋅ Woodstock Meadows BLDG.

Charming Woodstock countryside condo privately set off the road with beautiful meadow views and a peaceful, natural setting. This inviting home offers easy, low-maintenance living with the exterior upkeep, lawn care, and snow removal handled by the association. The first floor features hardwood flooring, a spacious living room with a wood-burning fireplace and slate hearth, and a dining area conveniently located off the kitchen. A newer sliding door leads from the living room to the deck, creating an ideal spot to relax and enjoy the tranquil surroundings. Upstairs are two comfortable bedrooms, including the primary bedroom with double closets, with a full bath conveniently situated between them. There's plenty of storage with an additional large closet in the hallway. The finished lower level adds valuable living space with a cozy family room/den, carpeting, a large closet, and a slider leading to a patio and small fenced area. The lower level also includes a utility/laundry area with washer and dryer, utility tub, hot water heater, and a workshop area. Windows were replaced in 2009. Enjoy the best of the Woodstock countryside with nearby walking trails, Roseland Park, restaurants and Woodstock Golf Course. The condo association allows up to two pets. An appealing opportunity for those seeking an affordable home in a private setting without the maintenance responsibilities of a single-family property.

33 Woodstock Mdws Unit 33, Woodstock

$74,999

2 Beds ⋅ 1 Baths ⋅ 24193441 MLS

Welcome to your summer "Home away from Home" Looking for your "Seasonal Home Away from Home" Look no further this cute as a button, privately situated park model. Fresh new updates and newly applied finishing touches, makes this unit able to just move on in and start enjoying the rest of the season. Just steps from the amenities. pool, pavilion, mini golf, cornhole field, basketball and short walk to the catch and release fishing pond. While also enjoying the tranquility of the home away from home feeling. This unit comes almost completely furnished.

25 Rte 197th Rte, Woodstock

$245,000

3 Beds ⋅ 2 Baths ⋅ 24147222 MLS

Welcome to this charming colonial with stenciled details that add character & style! This delightful antique property is the perfect fixer upper and features 3 bedrooms, 1 and a 1/2 bathrooms, and a clapboard exterior. Situated on a 0.9 acre lot, this home boasts a garden in the side yard and a large backyard, perfect for outdoor enjoyment. Additionally, a shed provides convenient storage for your tools and equipment. As you step inside, the exterior mudroom/laundry area offers a practical entry point and as well as storage. The main level has a kitchen that has country charm and ample cabinets as well as a full bath with a tub. The living room and dining area are adorned with a traditional fireplace and woodstove, creating a warm and inviting atmosphere. The primary bedroom and a dedicated craft room complete this floor. Upstairs, two more bedrooms await, each offering its own unique charm. One of the bedrooms features an ensuite half bathroom and a walk-in closet and skylight, providing privacy and convenience. Don't miss the opportunity to make this house your home!

1250 Rte 171, Woodstock

Start Your Search

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

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.