Woodstock Homes under $600,000

Welcome to Woodstock, Connecticut—where charming New England aesthetics meet a vibrant community spirit. Nestled in the picturesque Windham County, Woodstock boasts a rich history, breathtaking landscapes, and a serene lifestyle that beckons both families and retirees alike. Known for its lush green spaces, quaint farms, and historic architecture, Woodstock offers a delightful escape from the hustle and bustle of city life, making it the perfect place to call home.

As you explore the real estate market in Woodstock, you'll discover a variety of homes available for under $600,000. This price point opens the door to a wealth of options, from cozy cottages to spacious family homes, each exuding character and warmth. Many properties are set against stunning backdrops of rolling hills and vibrant foliage, providing a tranquil environment for relaxation and recreation.

The community is rich in amenities, with local shops, farmers' markets, and dining options that highlight the area's unique charm. Families will appreciate the top-rated schools and numerous parks, while nature enthusiasts can indulge in outdoor activities such as hiking, fishing, and exploring the nearby Quinebaug River.

Investing in a home in Woodstock means embracing a lifestyle filled with community events, seasonal festivals, and the simple joys of small-town living. With homes under $600,000, your dream of owning a piece of this idyllic town is well within reach. Experience the warmth and hospitality of Woodstock—where your perfect home awaits!

Newest Woodstock Homes under $600,000

$490,000

3 Beds ⋅ 2 Baths ⋅ 24214001 MLS

SOLAR PAID OFF AT CLOSING! Move in with owned solar working to keep your electric bills low from day one! This updated colonial sits on a peaceful acre on a quiet cul-de-sac in sought-after Woodstock, and the BIG-TICKET items are done: brand new roof and siding, new hot water heater, water filtration system, new washer and dryer, and a freshly painted back deck overlooking the yard and the above ground pool. The hard work is done and the peace of mind is included; all that's left is to make it your own. Enter through the new mudroom to a bright living room, separate dining room, and a kitchen with granite counters, stainless appliances and a breakfast bar. Off the kitchen, the bonus room with a wood stove is ready for whatever you need: home office, guest space, or den. Right next to it, the laundry room includes a second shower and sink, with the half bath just down the hall. Upstairs, the primary bedroom has a walk-in closet, plus two more bedrooms and a full bath with a brand new double vanity. Generator ready, with a 2-car attached garage. Minutes from Woodstock Academy, scenic Route 169, local farms, orchards and the Woodstock Fairgrounds, with easy access to I-395 and Massachusetts.

21 Fairfield Dr, Woodstock

$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

$499,900

6 Beds ⋅ 3 Baths ⋅ 24212211 MLS

Beautifully charming and beaming with character is this very spacious 2-family duplex; a rare find in Woodstock! This home is not your typical duplex and has a great floor plan in each unit. Perfect for an owner that wants to occupy a lovely home in a great location. Also nice for investors because the nicely updated and generously-sized units, each with their own laundry on the main floors, brings a higher rental income! The very large main house has attractive character, 4 large bedrooms, 2 full bathrooms, a dreamy updated kitchen with open floor plan to living room and dining areas. A first floor 4th bedroom and a laundry room on the main floor is large enough to be a 5th bedroom or office space! The second floor has three large bedrooms and a very large open den/craft room/office/home or college school area and a 2nd full bath! This unit has more space than you can dream to fill! The second unit is also generously-sized and nicely updated with 2 large bedrooms and a laundry room large enough to be a 3rd bedroom or office. Large living room leads to the updated open kitchen with an island and separate dining room. The home has a 3-car detached garage and peacefully landscaped grounds with room to garden. All separate utilities. Well water and public sewer. Listing Agent related to Seller. Come see this hidden gem before its gone!

9 Ellen Ln, 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

$499,900

3 Beds ⋅ 3 Baths ⋅ 24203840 MLS

To be built 6.5 room Colonial Home in a cozy neighborhood in Woodstock, At this price, this home will go quick! You have time to make several customized selections. Located on a fairly level and private lot, Tayler Tr is a quiet 20 year old open space subdivision (all homes less 20 years old) located on the Union town line off Tayler Rd, of which the remaining 27.77 acres of the original 44 acres on Tayler Rd was donated to the Wyndham Land Trust. The 94 acres across the street on Tayler Rd (south side) was donated to Nature's Conservancy, so no other homes will ever be built on Tayler Rd. AI says 36 minutes to 1 College St, Worcester (Holy Cross) and 40 minutes to Hartford. Owner is licensed real estate agent.

8-2 Tayler Trl, Woodstock

$509,000

3 Beds ⋅ 2 Baths ⋅ 1422207 MLS

Looking for a home that exudes the character and craftsmanship of bygone days without the challenges of a true antique? 15 Paine District Road looks and feels like it's been here for centuries, but this gorgeous reproduction Saltbox is less than 40 years old. Hand-built by its original owner with extraordinary attention to craftsmanship and period-inspired detail, it offers the warmth and character of early New England architecture recreated for modern living. Huge blocks of granite form the entry steps to each of the three doors, while exposed rough hewn beams and an oversized fireplace harken back to quieter days. Custom cabinetry and millwork by the renowned craftsmen at Brunarhans can be found throughout the home, from the solid wood kitchen, custom chair rails and molding to the raised paneled wall surrounding the fireplace. The kitchen features a cooking island and charming bay window dining nook with built-in seating. The flexible floor plan offers 3 bedrooms, including one on the first floor currently used as an office with more beautiful built in floor to ceiling custom cabinetry. The second floor offers a spacious primary and two additional bedrooms, the smaller one currently being used as a separate laundry area and playroom. The oversized garage includes a workshop area and storage loft. If you think this property looks pretty now, just imagine it when the fall foliage blooms. Act now and you can be moved in by peak leaf season, your pumpkins and scarecrow await!

15 Paine District Road, Woodstock

$595,000

4 Beds ⋅ 3 Baths ⋅ 24204008 MLS

Modern amenities meet unmatched seclusion in this 2,000+ sq ft colonial. A mostly level lot offers abundant green space, fruiting plants, and perennials, while the side deck and yard open to a beautiful natural view of the Still River-ideal for outdoor entertaining or quiet, serene living. Inside, gleaming maple floors lead to a first-floor bedroom with attached pass-through bath, a modern eat-in kitchen with double wall ovens and a propane stovetop, a large dining room, and a spacious living room with a functional fireplace. Upstairs, a hallway full bath serves three additional bedrooms, including the primary suite with its own attached full bath. The walk-up attic's excellent ceiling height and volume create a strong opportunity to add livable square footage. The basement's layout and ceiling height are equally well suited to finishing and expanding the home further. An attached two-car garage and paved driveway provide ample parking. If you want modern comfort, privacy, and room to grow in a peaceful woodsy setting, this is the home for you!

47 Sherman Rd, Woodstock

$549,000

2 Beds ⋅ 2 Baths ⋅ 24201418 MLS

There's something special about seeing the lake from home and being at the water in just a short walk. Welcome to 4 Oak Drive, a thoughtfully cared-for 2-bedroom, 2-full-bath home with a spacious loft in the Lake Bungee community. Offering deeded lake & beach rights and water views, simply walk across the street to the boat launch and enjoy easy access to the lake. This newer home sits on an inviting corner lot surrounded by colorful flowers and raised vegetable gardens, plus an oversized shed less than a year old for additional storage. Traditional stone walls along the adjoining historic cemetery add to the peaceful New England setting. Inside, the open-concept kitchen with granite countertops and center island flows comfortably into the dining and living areas, with plenty of natural light and views toward the lake. Step onto the deck to unwind and enjoy the glowing sunsets. Both bedrooms are on the main level, including the primary with a large walk-in closet, private full bath and sliders to its own deck. Upstairs, the spacious loft offers flexible additional living space, two closets and attic storage. The full walk-out basement with sliders provides excellent storage and potential for future finished space. Generator hookup ready. Lovingly maintained and move-in ready, this welcoming home offers a wonderful place to enjoy the lake, the seasons and the simple pleasures of home, conveniently located near the MA line and area amenities.

4 Oak Dr, 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

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