Woodstock Homes under $500,000

Welcome to Woodstock, Connecticut, a charming town nestled in Windham County that perfectly blends rich history with modern living. Known for its picturesque landscapes and vibrant community spirit, Woodstock offers a serene escape with its rolling hills, lush greenery, and tranquil lakes. This quaint New England town is not just a haven for nature lovers; it also boasts a thriving arts scene, with local galleries and cultural events that reflect the creativity of its residents.

For those seeking a place to call home, Woodstock presents an enticing real estate market with homes available under $500,000. Here, you'll find a variety of properties that cater to diverse tastes and lifestyles. Whether you’re drawn to historic colonial-style houses, charming cottages, or contemporary designs, Woodstock has something for everyone. The affordability of these homes makes it an excellent option for first-time buyers, families, or anyone looking to enjoy the benefits of small-town living without breaking the bank.

In addition to its beautiful homes, Woodstock offers a wealth of amenities. Enjoy leisurely walks along scenic trails, explore local farms, or indulge in the delightful dining options that showcase farm-to-table cuisine. The strong sense of community is palpable here, with seasonal festivals and farmers' markets bringing residents together to celebrate the town’s unique character.

Discover the charm of Woodstock, CT, where affordable living meets a vibrant lifestyle. Your dream home awaits in this idyllic setting, where every day feels like a retreat!

Newest Woodstock Homes under $500,000

$374,900

4 Beds ⋅ 2 Baths ⋅ 24209768 MLS

Really does a two-family home ever come on the market in Woodstock, never mind one on 3.5 acres. Even more rare is finding a two-family home you can live in with a large commercial/industrial garage for all of your toys, projects, and potential business use. Property consists of two, 2 bedroom-1-bathroom apartments. Each unit paying their own electric/heat. The lower garage has its own electric panel, heat and even a half bathroom. Oversized 10-foot brand new garage door along with steel I-beam construction. Proper property has a newer septic system, and a modern drilled well.

616 Rte 197, 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.

8-2 Tayler Trl, 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

$74,899

2 Beds ⋅ 1 Baths ⋅ 73552757 MLS

Call Today Motivated seller.. Book your tour today easy to show.. 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 197 Unit 70, Woodstock

$479,900

3 Beds ⋅ 2 Baths ⋅ 24187904 MLS

Welcome home to this charming colonial tucked away on a peaceful cul-de-sac, offering privacy and picturesque views on a full acre of land. As you step in through the fresh new mudroom, you will find a spacious, bright living room, a separate dining room, and a beautiful kitchen with stainless steel appliances, a breakfast bar, abundant cabinet space, and access to a private back deck overlooking a scenic backyard and surrounding nature. Just off the kitchen, you will find a versatile bonus room currently used as a bedroom offering endless possibilities as a family room, home office, playroom or guest space. This area also features a wood stove, and a convenient laundry room complete with a bonus shower and sink. Upstairs the spacious primary bedroom includes a walk in closet, accompanied by two additional bedrooms and a full bath with a brand new double vanity. Major improvements provide added peace of mind, including a brand new roof and siding, water filtration system, new hot water heater, new washer and dryer, and leased solar panels for improved energy efficiency. A two car garage and beautiful natural surroundings complete this move in ready home in a highly desirable location.

21 Fairfield Dr, 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

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