24

Outlying Woodstock Homes for Sale

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  • /40

    $649,900

    • 4 Beds
    • 2.5 Baths
    • 2,682 Sq Ft

    37 Pulpit Rock Rd, Woodstock, CT 06281

    Location, location, location! Tucked away on a quiet scenic road just steps from historic Woodstock Hill and Woodstock Academy, this classic Colonial offers 2,682 sq. ft. of timeless charm on 1.6 acres-one of the most desirable and private settings in Woodstock. Inside, wide-plank oak floors, exposed beams, and two fireplaces create a warm and inviting atmosphere. The open kitchen and dining

    Agent Photo

    Carol Ryniewicz

    CR Premier Properties

    (860) 854-3110

    37 Pulpit Rock Rd, Woodstock, CT 06281
  • /12

    $250,000

    • Land
    • 5 Acres
    • $48,924 per Acre

    00 Joy Rd, Woodstock, CT 06281

    "Life is a Joy on Joy Road" Nestled in the heart of Woodstock, CT, this stunning 5.11-acre building lot offers the perfect balance of peaceful seclusion and easy access to modern conveniences. Surrounded by lush woodlands and gently rolling terrain, this property provides an idyllic setting for your dream home, offering privacy, natural beauty, and a connection to nature. Despite its serene

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    (860) 846-4563

    00 Joy Rd, Woodstock, CT 06281
  • /11

    $925,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 3,500 Sq Ft

    0 Joy Rd, Woodstock, CT 06281

    Luxury Ranch-Style Home To Be Built by DHS Copeland Builders - Woodstock, Ct Offered on a Private 5-Acre Parcel - Bring Your Plans or Use Ours! Discover the perfect blend of elegance and tranquility with this to-be-built luxury ranch-style home by the renowned DHS Copeland Builders. Centrally located in the heart of Woodstock, CT, this rare 5-acre parcel offers the ideal canvas for your dream

    Agent Photo

    Elizabeth Scranton

    Kazantzis Real Estate, LLC

    (860) 813-2921

    0 Joy Rd, Woodstock, CT 06281
  • /16

    $895,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 3,356 Sq Ft

    36 Olde Meadow Rd, Woodstock, CT 06281

    Welcome to Eastwood Estates - Luxury Living in the Heart of Woodstock! Discover the elegance and tranquility of Eastwood Estates, a prestigious enclave of just eight finer homes nestled in one of Woodstock's most desirable settings. This 3,356 sq ft Colonial TO BE BUILT is thoughtfully designed for those seeking timeless sophistication, quality craftsmanship, and a connection to nature. With 18

    Agent Photo

    Tina Lajoie

    William Raveis Real Estate

    (860) 374-2832

    36 Olde Meadow Rd, Woodstock, CT 06281
  • /40

    $715,000

    • 4 Beds
    • 3.5 Baths
    • 4,536 Sq Ft

    101 Center Rd, Woodstock, CT 06281

    This beautiful sprawling custom colonial is set on 9 acres of land at the end of a winding long driveway and surrounded by open area. Grand living spaces with cathedral ceilings and a floor to ceiling fireplace, tons of natural light, 4 bedrooms & 3.5 bathrooms, a 1500 sqft in-law suite with additional bedroom, new appliances, spacious 2 car garage, and an out building with electricity and

    Jeff Valentine William Pitt Sotheby's Int'l

    101 Center Rd, Woodstock, CT 06281
  • /40

    $799,000

    • 3 Beds
    • 4 Baths
    • 2,323 Sq Ft

    223 Barlow Cemetery Rd, Woodstock, CT 06281

    Discover modern luxury living in this stunning 2011-built Colonial. Perfectly situated on a picturesque waterfront lot with privately owned pond frontage, this thoughtfully designed home offers a lifestyle of elegance and comfort. The home offers 3 bedrooms, two full baths, and two half baths. You will love the classic oak flooring, crown molding, and light-filled living spaces. The finished

    John Downs Berkshire Hathaway NE Prop.

    223 Barlow Cemetery Rd, Woodstock, CT 06281
  • /40

    $679,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 2,669 Sq Ft

    402 Perrin Rd, Woodstock, CT 06281

    Welcome to this charming 2.7-acre property, where functionality meets potential. Perfectly suited for horse enthusiasts, this small yet mighty property provides endless possibilities-whether you're looking to house your own horses, run a boarding business, or provide training. The beautifully remodeled antique home exudes warmth and character, featuring a cozy living room with a wood stove, a

    Kelly Ryan William Raveis Real Estate

    402 Perrin Rd, Woodstock, CT 06281
  • /15

    $299,999

    • 3 Beds
    • 1.5 Baths
    • 1,440 Sq Ft

    566 Route 197, Woodstock, CT 06281

    Welcome to this charming home! This recently renovated home is move in ready! Sitting on a small, but usable, 0.2 acre fenced-in lot, this 3 bedroom, 1.5 bathroom home is ready for immediate occupancy. The home is approximately 1,400 sq. ft. with spacious rooms & bedrooms. On the first floor, you'll find kitchen has been tastefully updated with updated cabinets, countertops, backsplash &

    Skyla Gagnon RE/MAX Bell Park Realty

    566 Route 197, Woodstock, CT 06281
  • /40

    $449,900

    • 3 Beds
    • 1.5 Baths
    • 1,632 Sq Ft

    31 Pond Factory Rd, Woodstock, CT 06281

    Nestled in the beautiful and desirable town of Woodstock, CT-just minutes from the Massachusetts border-this charming 1,600+ sq ft home offers the perfect blend of comfort, convenience, and location. Set on a private 2-acre lot on a non-through road within walking distance to the town beach, this 3-bedroom, 1.1-bath home is filled with thoughtful features. The main level boasts an open and

    Jared Meehan RE/MAX Bell Park Realty

    31 Pond Factory Rd, Woodstock, CT 06281
  • /34

    $550,000

    • 3 Beds
    • 2.5 Baths
    • 2,362 Sq Ft

    359 Barlow Cemetery Rd, Woodstock, CT 06281

    Welcome to 359 Barlow Cemetery Rd - a truly one-of-a-kind property set on 3.2 scenic acres that lead to the peaceful waters of Bungee Brook. This spacious home offers a versatile layout, featuring a large primary bedroom suite, two additional bedrooms, and a generous supplemental room on the upper level-perfect for a home office, gym, or guest space. The fully finished basement is an

    Adam Gumula Kazantzis Real Estate, LLC

    359 Barlow Cemetery Rd, Woodstock, CT 06281
  • /5

    $299,000

    • 2 Beds
    • 1.5 Baths
    • 1,196 Sq Ft

    10 Laurel Hill Dr, Woodstock Valley, CT 06282

    LOCATION, LOCATION, LOCATION!!!! This cozy 2-3 bedroom ranch is nestled on .40 of an acre lot with views of Lake Bunggee. Lake Bunggee is a private lake association for residents only. Access to the beach and boat launch is across the street. The roof is only 10 years old, electrical was updated and new wood decks on each side of the home. One floor living including a woodburning fireplace for

    Simonne Corriveau KW Legacy Partners

    10 Laurel Hill Dr, Woodstock Valley, CT 06282
  • /40

    $599,900

    • 5 Beds
    • 3.5 Baths
    • 4,172 Sq Ft

    4 Perrin Rd, Woodstock, CT 06281

    Welcome to the exquisite Ebenezer Stoddard house built in 1800 once an inn for travelers on an early state route. This 4100 sq ft home is filled with character, history and updates for modern convenience, while saving the historic charm! The home resides on an 1.2 acre lot, mostly cleared with plenty of room for family gatherings of any size! Entering the home into an official mudroom - leave

    Kerri Mullen CR Premier Properties

    4 Perrin Rd, Woodstock, CT 06281
  • /31

    $1,250,000

    • 3 Beds
    • 2.5 Baths
    • 3,983 Sq Ft

    584 Prospect St, Woodstock, CT 06281

    For those who belong to the land. Over 100 acres of private, usable terrain at the CT/MA line, Bear Hill Estate is a fully realized lifestyle retreat for the discerning equestrian or outdoor enthusiast, with effortless access to I-395, I-84, and the Mass Pike. At its heart sits a 3 bed, 2.5 bath custom log home-crafted from white pine logs hand-felled in Nova Scotia, where the bespoke cabinetry

    Jennie Kesselman Berkshire Hathaway NE Prop.

    584 Prospect St, Woodstock, CT 06281
  • /39

    $1,250,000

    • 2 Beds
    • 2 Baths
    • 2,340 Sq Ft

    1669 Route 169, Woodstock, CT 06281

    Welcome to Hilltop Meadows-a one-of-a-kind, 60-acre luxury hay farm nestled in Connecticut's scenic "Quiet Corner." Set high above Route 169 in North Woodstock, this breathtaking property offers rolling meadows, mature forests, and serene privacy just 60 miles from Boston and 150 from Manhattan. The heart of the property is a newly updated 2-bed, 2-bath, 2,340 sq ft farmhouse blending historic

    Ryan De Lello William Pitt Sotheby's Int'l

    1669 Route 169, Woodstock, CT 06281
  • /30

    $64,900

    • 2 Beds
    • 1 Bath
    • 450 Sq Ft

    91 Meadowside Rd, Woodstock, CT 06281

    Welcome to Beautiful Meadowside of Woodstock Campground, your home away from home! This is a rare opportunity to own your very own campsite along with the 1991 Mallard 38' x 140" x 12' Model with a Custom built sunroom attached located in the back of the campground. Enjoy the peace and serenity of nature. The camper is made up of 2 full/queen beds, the full bathroom is spacious with a tub, toilet

    Kerri Mullen CR Premier Properties

    91 Meadowside Rd, Woodstock, CT 06281
  • /27

    $325,000

    • 2 Beds
    • 1 Bath
    • 1,125 Sq Ft

    28 Oak Dr, Woodstock Valley, CT 06282

    LAKE LIFE IN WOODSTOCK. This charming year-round home in Woodstock, CT, offers a unique opportunity to embrace a peaceful lake lifestyle. Built in 1955, the residence sits on a generous 1.1-acre multi-tiered lot, providing ample privacy and seasonal lake views. KEY FEATURES: Deeded Beach Rights: Enjoy direct access to Bungee Lake with deeded beach rights, including access to association beaches

    Donna Copeland William Raveis Real Estate

    28 Oak Dr, Woodstock Valley, CT 06282
  • /37

    $559,000

    • 4 Beds
    • 2.5 Baths
    • 2,150 Sq Ft

    101 Child Hill Rd, Woodstock, CT 06281

    Welcome to this beautiful & idyllic colonial, sitting off of Woodstock Hill! The views are outstanding! This home is known as the " White House" by the locals and in walking distance to the Academy!Drive up the long paved driveway and walk up the stairs to an expansive NEW TREX decking overlooking the countryside. Step inside the remodeled kitchen where you have an inset window seat, with higher

    Skyla Gagnon RE/MAX Bell Park Realty

    101 Child Hill Rd, Woodstock, CT 06281
  • /36

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 2,016 Sq Ft

    104 Pulpit Rock Rd, Woodstock, CT 06281

    This 4 Bedroom 2.5 bath meticulously maintained Colonial style home offers a seamless blend of classic charm and modern comfort creating an inviting and functional living environment. High ceilings and abundant natural light illuminate the rich engineered wood floors and detailed crown molding throughout. Enjoy this beautiful kitchen featuring custom Brunarhans cabinetry and granite countertops,

    Belinda Culp Berkshire Hathaway NE Prop.

    104 Pulpit Rock Rd, Woodstock, CT 06281
  • /39

    $1,986,000

    • 4 Beds
    • 3.5 Baths
    • 5,104 Sq Ft

    175 Pulpit Rock Rd, Woodstock, CT 06281

    A once-in-a-generation opportunity. Please visit this stunning Georgian estate situated on 55 hilltop acres in desirable Woodstock, CT. Enjoy breathtaking long views all the way to Rhode Island! A few of the exceptional assets offered include an elegant in-law apartment, a large 6 stall horse barn with office, an inviting in-ground pool, and 25 acres of fenced open pasture. As you approach the

    John Downs Berkshire Hathaway NE Prop.

    175 Pulpit Rock Rd, Woodstock, CT 06281
  • /23

    $29,900

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft

    25 Route 197 Unit Lot 40, Woodstock, CT 06281

    Price Improvement! Welcome to your home away from home! This is your opportunity to own your very own campsite located in in the beautiful Meadowside of Woodstock community! Included is a 1995 33' Corsica Cobra 30BH trailer that has been well cared for. The trailer has a queen bed and a bunk room with two additional sleeping bunks, a full bath with a standup shower and an eat-in kitchen. There is

    Keri Roy Kazantzis Real Estate, LLC

    25 Route 197 Unit Lot 40, Woodstock, CT 06281
  • /14

    $85,000

    • Land
    • 0.88 Acre
    • $96,591 per Acre

    Lot 4 Aplin Hill Ln, Woodstock, CT 06282

    Discover the perfect canvas for the home you have been dreaming of on this .88-acre lot, nestled in an approved subdivision in Woodstock Valley. Lot 4 is set back from the road and is bordered by conservation land on the northern and eastern sides providing a private setting in a cul-de-sac community. This subdivision maintains architectural guidelines to preserve the aesthetic and value of the

    Kristen Kaskela Berkshire Hathaway NE Prop.

    Lot 4 Aplin Hill Ln, Woodstock, CT 06282
  • /2

    $99,900

    • Land
    • 12 Acres
    • $8,325 per Acre

    00 Prospect St, Woodstock, CT 06281

    Discover the perfect canvas for your dream home or private retreat on this stunning 12-acre parcel located in scenic Woodstock, Connecticut. This unique piece of land offers a peaceful setting with a blend of rolling topography, mature trees, and a beautiful pond-ideal for nature lovers, homesteaders, or anyone seeking privacy and serenity. The land features varied elevations, providing

    Mateusz Chojnicki CR Premier Properties

    00 Prospect St, Woodstock, CT 06281
  • /2

    $99,000

    • Land
    • 10 Acres
    • $10,270 per Acre

    0 Rt 198, Woodstock, CT 06281

    This beautiful laurel-rich hard and soft wood land has wide frontage on CT 198 and on town road Pole Bridge Road, making this an easily accessible home sites. Property is sold AS-IS, contingent on clear title. There is a special permit for a commercial Building. Septic plan and building design are at the Town Hall. Please note: there is not yet driveway access to this property.

    Nicole Gleason CR Premier Properties

    0 Rt 198, Woodstock, CT 06281
  • /2

    $144,000

    • Land
    • 9 Acres
    • $16,590 per Acre

    0 English Neighborhood Rd, Woodstock, CT 06281

    WOODSTOCK LAND - Discover your dream property on 8.68 acres of picturesque countryside in Woodstock. This land features endless possibilities, whether you're looking to build your custom home or create your private retreat. Nestled in a rural area with minimal traffic, this serene setting provides the perfect escape from the hustle and bustle of city life. Surrounded by natural beauty, the

    Doug Taber Taber Realty, LLC

    0 English Neighborhood Rd, Woodstock, CT 06281

Why Live in Outlying Woodstock

Outlying Woodstock in Woodstock is a rural New England retreat known for its natural beauty and seclusion. The area features sprawling estates, dairy farms, and wineries, attracting visitors and transplants from across the Northeast. Homes are spread out, with many properties occupying large lots, some even boasting their own airfields or medieval moats. Waterfront homes are common along the town's lakes and ponds. The Woodstock Academy, a highly rated private school, offers top-notch education with numerous Advanced Placement courses and international travel opportunities. Local attractions include Crystal Pond Park and Roseland Park, which offer year-round recreational activities such as boating, swimming, ice skating, and cross-country skiing. Woodstock is also a destination for antique shopping, with boutiques like The Rusty Relic and The Olde Pineapple, and fresh food marketplaces like Elm Farm’s Farm to Table Market. The town hosts events at Taylor Brooke Winery and the historic Roseland Cottage, which features an annual fine arts and craft festival. While Woodstock is secluded, it is accessible via Connecticut Routes 169 and 171, and Interstate 395, with Worcester 30 miles away, Boston 70 miles away, and Hartford 45 miles away. The nearest full-service hospital is UMass Memorial-Harrington Hospital, 10 miles away.

Frequently Asked Questions

Is Outlying Woodstock a good place to live?
Outlying Woodstock is a good place to live. Outlying Woodstock is considered very car-dependent and somewhat bikeable. Outlying Woodstock is a rural neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Outlying Woodstock has 6 parks for recreational activities. It is sparse in population with 0.1 people per acre and a median age of 46. The average household income is $128,656 which is above the national average. College graduates make up 46% of residents. A majority of residents in Outlying Woodstock are home owners, with 11.5% of residents renting and 88.5% of residents owning their home. A local real estate agent serving Outlying Woodstock can help you decide if this neighborhood is the right one for you. Learn more on our Outlying Woodstock neighborhood guide.
Is Outlying Woodstock, CT a safe neighborhood?
Outlying Woodstock, CT is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Outlying Woodstock?
The median home price in Outlying Woodstock is $399,990. If you put a 20% down payment of $80,000 and had a 30-year fixed mortgage with an interest rate of 6.74%, your estimated principal and interest payment would be $2,070 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $89K a year to afford the median home price in Outlying Woodstock. The average household income in Outlying Woodstock is $129K.
What are the best public schools in Outlying Woodstock?
The best public schools that serve Outlying Woodstock are:
What are the best private schools in Outlying Woodstock?
The best private schools that serve Outlying Woodstock are:
  • Putnam Science Academy has an A Niche grade, a student teacher ratio of 5:1 and an average review score of 4.6.
What are the most popular zip codes in Outlying Woodstock, Woodstock, CT?
The most popular zip codes in Outlying Woodstock, Woodstock, CT include 06281, 06282, 01550, 06255 and 01571.
What are the most popular neighborhoods near Outlying Woodstock, Woodstock, CT?
The most popular neighborhood near Outlying Woodstock, Woodstock, CT is Wales.
Are home prices dropping in Outlying Woodstock?
Yes, home prices in Outlying Woodstock are down 16% in the last 12 months.

Home Trends in Outlying Woodstock, CT

Housing Trends

Median Sale Price
$407,500
Median Single Family Sale Price
$400,000
Median Townhouse Sale Price
$240,000
Median 2 Bedroom Sale Price
$369,950
Average Price Per Sq Ft
$193
Number of Homes for Sale
7
Last 12 months Home Sales
42
Months of Supply
2.00
Median List Price
$399,990
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-1%
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