Vintage homes for sale & real estate in Woodstock, VT

20 homes

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$795,000

4 beds3 baths3,190 sq ft

598 E Woodstock Rd, Woodstock, VT 05091

2.94 acre lot • Garage • Built 1925

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ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Gilbert’s Hill is one of Vermont’s most celebrated properties and a national landmark for its contribution to the sport of alpine skiing. Spanning 112.88± acres in Woodstock (79.31 acres) and Pomfret (33.57 acres), the farm is recognized as the birthplace of lift-served skiing in America, where the first rope tow was installed in 1934. Today, its open pastures, rolling terrain, and historic ski hill remain wonderfully intact — a living landscape that forever changed the trajectory of winter sport and the development of recreational skiing in the United States. At the heart of the property is a restored circa 1855 Greek Revival brick farmhouse with four bedrooms, two

$2,600,000

4 beds2 baths3,000 sq ft

1362 Barnard Rd, Woodstock, VT 05091

Historic ski hill • 112.88 acre lot • Garage

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
This charming 2-bedroom ranch house offers a nice layout for main floor living. Features include a sunroom entrance, two bedrooms, a full bath, laundry room, and a main living/dining area with a kitchen, all within a rural setting with ample natural light, local views, and a deck. Recent updates include a primary bedroom ensuite featuring a custom walk-in shower and double sinks, new flooring, a brick accent wall in the living room, fresh paint, and a cleared and seeded backyard. A 3-bedroom septic system installed in 2021, a drilled well replacing the spring water source, and generator wiring for power backup. Situated on a quiet country road between Woodstock and South Woodstock, offering

$425,000

2 beds2 baths1,440 sq ft

1079 Fletcher Hill Rd, Woodstock, VT 05071

Double sinks • Brick accent wall • Sunroom entrance

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Just minutes from the heart of Woodstock, this 3-bedroom, 3-bath home with a dedicated office/family room has been transformed from the ground up into a modern, energy-efficient retreat. Taken down to the studs, the renovation was comprehensive—every system replaced, with all new wiring, plumbing, insulation, and mechanicals, along with a new roof, Pella windows, central heating, and air conditioning. A brand-new two-car garage will be completed before closing, adding convenience and value. Inside, light-filled spaces showcase new, wide-plank white oak flooring, a beautifully designed kitchen, and spa-like bathrooms. The thoughtful floor plan includes a private office, perfect for wor

$1,150,000

3 beds2.5 baths2,220 sq ft

958 E Woodstock Rd, Woodstock, VT 05091

Central heating • Air conditioning • Covered porch

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Charming 4 bedroom farmhouse with attached barn/garage with lots of overhead storage is located across the road from the scenic Ottauquechee River. Minutes from Woodstock Village Green with all of its amenities and a short distance from Killington with its world renown Ski Resort. Year round activities abound ! The house has a sunny eat in kitchen, spacious dining room and a living room complete with a wood burning fireplace. A bedroom and full bath on the first floor adds to convenience of living . The charming front porch with views of Killington is a lovely place to enjoy relaxing and entertaining friends . Make an appointment today to view this lovely property .

$439,000

4 beds2 baths1,617 sq ft

5798 W Woodstock Rd, Woodstock, VT 05091

Attached barn • Spacious dining room • Sunny eat in kitchen

Property at 17 Linden Hl, Woodstock, VT 05091, 4 beds, 3 baths

$1,200,000

4 beds3 baths2,736 sq ft

17 Linden Hl, Woodstock, VT 05091

Property at 41 Pleasant St, Woodstock, VT 05091, 9 beds, 11 baths

$2,599,000

9 beds11 baths5,993 sq ft

41 Pleasant St, Woodstock, VT 05091

Property at 37 South St, Woodstock, VT 05091, 3 beds, 2 baths

$785,000

3 beds2 baths1,660 sq ft

37 South St, Woodstock, VT 05091

Property at 16 Church St, Woodstock, VT 05091, 4 beds, 3 baths

$1,295,000

4 beds3 baths3,089 sq ft

16 Church St, Woodstock, VT 05091

Property at 3364 W Woodstock Rd, Woodstock, VT 05091, 4 beds, 3 baths

$549,000

4 beds3 baths2,470 sq ft

3364 W Woodstock Rd, Woodstock, VT 05091

Property at 18 The Grn, Woodstock, VT 05091, 6 beds, 7 baths

$3,500,000

6 beds7 baths5,142 sq ft

18 The Grn, Woodstock, VT 05091

Property at 1782 Randall Rd, Woodstock, VT 05091-0488, 4 beds, 3 baths

$985,000

4 beds3 baths2,785 sq ft

1782 Randall Rd, Woodstock, VT 05091-0488

Property at 37 Atwood Ave, Woodstock, VT 05091, 2 beds, 1 bath

$420,000

2 beds1 bath768 sq ft

37 Atwood Ave, Woodstock, VT 05091

Property at 1522 Barnard Rd, Woodstock, VT 05091, 5 beds, 3.5 baths

$1,595,000

5 beds3.5 baths3,648 sq ft

1522 Barnard Rd, Woodstock, VT 05091

Property at 7 Slayton Ter, Woodstock, VT 05091, 4 beds, 2.5 baths

$1,495,000

4 beds2.5 baths2,532 sq ft

7 Slayton Ter, Woodstock, VT 05091

Property at 39 Elm St Unit B, Woodstock, VT 05091, 3 beds, 3.5 baths

$1,689,000

3 beds3.5 baths3,294 sq ft

39 Elm St Unit B, Woodstock, VT 05091

Property at 509 Church Hl, Woodstock, VT 05091, 3 beds, 3 baths

$915,000

3 beds3 baths2,150 sq ft

509 Church Hl, Woodstock, VT 05091

Property at 15 Central St, Woodstock, VT 05091, 4 beds, 1.5 baths

$1,600,000

4 beds1.5 baths6,014 sq ft

15 Central St, Woodstock, VT 05091

Property at 2706 E Woodstock Rd, Woodstock, VT 05091, 4 beds, 3.5 baths

$1,750,000

4 beds3.5 baths5,000 sq ft

2706 E Woodstock Rd, Woodstock, VT 05091

Property at 234 Randall Rd, Woodstock, VT 05091, 2 beds, 1 bath

$845,000

2 beds1 bath600 sq ft

234 Randall Rd, Woodstock, VT 05091

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ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Welcome to the historic Bridgewater Inn — a rare, turn-key Vermont property perfectly positioned between Woodstock Village, Killington Resort, and Okemo Mountain. This unique offering features a spacious 3-bedroom, 3-bath main home along with four fully equipped guest suites, creating exceptional flexibility for full-time living, multi-generational use, or continued short-term rental success. The main home is inviting and well-appointed, offering two covered porches, a large eat-in kitchen, a cozy living room with a gas fireplace, and two dedicated game rooms for guest entertainment. Recent updates include new furniture, paint, flooring, and mini splits for year-round comfort. Attache

$799,000

7 beds7 baths4,581 sq ft

7137 US Route 4, Bridgewater, VT 05034

Large eat-in kitchen • Cozy living room • Gas fireplace

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Welcome to "Valley Brook Farm", a Historic Cape in the middle of Horse country on 12.92 acres with Barns, rolling & level Pasture, a swimming Pond, and Brook. Located in the heart of the nationally renowned Green Mountain Horse Association trail network. Nestled on scenic & bucolic Jenneville Road, this c. 1820 Cape offers the warmth of wide pine floors, post-and-beam character, and sun-filled spaces. The 1.75-story home (2,212+ sq ft) includes 4 bedrooms and 2 full baths. The charming country kitchen features an expansive Family Room area and breakfast nook with a view of the rear meadows. The adjoining pantry, pellet stove, and coat closet make for practical Vermont

$635,000

4 beds2 baths2,212 sq ft

298 Jenneville Rd, Hartland, VT 05048

Swimming pond • 12.92 acres • Barns

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Two buildings on one parcel in desirable Hartland, Vermont! This flexible and well-maintained property includes a single-family home and a duplex, offering outstanding potential for owner occupancy, multi-generational living, or investment income. Ideally situated just 25 minutes from Hanover, NH, and 10 minutes from Woodstock, VT, this location provides the perfect balance of convenience and rural charm. The single-family home features one bedroom upstairs and two additional rooms downstairs. The duplex offers 2 two-bedroom apartments—perfect for reliable rental income or to offset your living expenses. Both buildings include laundry facilities, and the property benefits from ample p

$452,600

— beds3 baths2,915 sq ft

282 Skunk Hollow Rd, Hartland, VT 05048

Laundry facilities • Ample parking • Single family home

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
US Route 4 in Vermont - the east/west corridor from I-89 and the Killington Ski Area. Highway frontage between Quechee and Woodstock, VT. Minutes from Dartmouth College in Hanover, NH; near the intersection of I-89 and 91 at the Connecticut River; also close to Northern New England’s major DH Medical complex and Cancer Center in Lebanon, NH, as well as the VA Hospital in White River Junction. 1.5 story Cape (3 bedroom/2 bath - 2,334 sq ft) from 1850, with numerous outbuildings. The site of a very successful farmers market for many years, then Fool on the Hill, a gift/crafts/novelties business. In addition to the barn, 3 large sheds (1,440 sf - 810 sf - 500 sf) suitable for outdoor eve

$1,300,000

3 beds2 baths2,334 sq ft

72 Wood Rd, Hartford, VT 05001

Highway frontage • Water views • 9.1 acre lot

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Endless Possibilities Await – Antique Home with Charm & Character. If you have an eye for potential, this charming antique home is your canvas. Bursting with character and nestled in one of the most desirable towns in Vermont's Upper Valley, it offers a rare opportunity to create something truly special. With plenty of space to design not just one, but two master suites—one on the main floor and another upstairs complete with a private balcony overlooking a babbling brook—this home invites creativity and vision. Wake up with your morning coffee surrounded by the lush, vibrant foliage Vermont is famous for. Set in a close-knit community known for its welcoming spirit,

$165,000

3 beds1 bath1,554 sq ft

89 route 12, Hartland, VT 05048

Two master suites • Private balcony • Babbling brook

ABOUT THIS HOME
Vintage Home for sale in Woodstock, VT:
Charming New Englander in the Heart of Quechee! Owned by the same family for more than 30 years, this classic New Englander is set on a spacious double lot in Quechee’s Historic Mill District. The home offers practical living spaces inside, while outside you’ll find ample room for gardening, play, or simply relaxing by the shade trees and small water feature. Being sold “As Is, ” this is a wonderful opportunity to own a piece of Quechee’s history in a truly desirable location. Agent related to Sellers. This is a non-QLLA property, giving new owners the flexibility of no HOA while still being just moments from all that Quechee has to offer—the Ottauquechee

$550,000

3 beds1.5 baths1,755 sq ft

2295 Quechee Main St, Hartford, VT 05059

Shade trees • Double lot • Small water feature

Property at 7868 Pomfret Rd, North Pomfret, VT 05053, 4 beds, 3 baths

$495,000

4 beds3 baths3,350 sq ft

7868 Pomfret Rd, North Pomfret, VT 05053

Property at 6077 VT Route 12, Barnard, VT 05031, 4 beds, 3 baths

$795,000

4 beds3 baths2,099 sq ft

6077 VT Route 12, Barnard, VT 05031

Property at 10 Bischoff Ln, Hartland, VT 05048, 4 beds, 5.5 baths

$1,600,000

4 beds5.5 baths3,680 sq ft

10 Bischoff Ln, Hartland, VT 05048

Property at 505 Deweys Mills Rd, Hartford, VT 05047, 6 beds, 5 baths

$1,400,000

6 beds5 baths4,571 sq ft

505 Deweys Mills Rd, Hartford, VT 05047

Property at 6852 US Route 4, Bridgewater, VT 05034, 3 beds, 2 baths

$449,000

3 beds2 baths1,489 sq ft

6852 US Route 4, Bridgewater, VT 05034

Property at 5518 VT Route 12, Barnard, VT 05031, 6 beds, 4.5 baths

$1,999,000

6 beds4.5 baths7,619 sq ft

5518 VT Route 12, Barnard, VT 05031

Property at 7873 Pomfret Rd, North Pomfret, VT 05053, 3 beds, 1.5 baths

$434,500

3 beds1.5 baths1,582 sq ft

7873 Pomfret Rd, North Pomfret, VT 05053

Property at 1279 Old Bridgewater Hill Rd, Bridgewater Corners, VT 05035, 4 beds, 4 baths

$3,300,000

4 beds4 baths5,000 sq ft

1279 Old Bridgewater Hill Rd, Bridgewater Corners, VT 05035

Property at 3147 Mount Hunger Rd, Barnard, VT 05031, 5 beds, 8.5 baths

$15,000,000

5 beds8.5 baths9,679 sq ft

3147 Mount Hunger Rd, Barnard, VT 05031

Property at 5100 Route 100, Plymouth, VT 05056, 4 beds, 2.5 baths

$599,000

4 beds2.5 baths2,520 sq ft

5100 Route 100, Plymouth, VT 05056

Property at 3 Mace Hill Rd, Hartland, VT 05048, 6 beds, 3 baths

$425,000

6 beds3 baths2,243 sq ft

3 Mace Hill Rd, Hartland, VT 05048

Property at 18 Oak Chapel Rd, Bridgewater Corners, VT 05035, 3 beds

$239,000

3 beds— baths1,984 sq ft

18 Oak Chapel Rd, Bridgewater Corners, VT 05035

Property at 61 Academy Cir, South Woodstock, VT 05071, 6 beds, 5 baths

$3,500,000

6 beds5 baths5,433 sq ft

61 Academy Cir, South Woodstock, VT 05071

Property at 52 Upper Rd, Bridgewater, VT 05035, 7 beds, 6 baths

$799,000

7 beds6 baths5,028 sq ft

52 Upper Rd, Bridgewater, VT 05035

Vintage Homes for Sale in Woodstock

There are currently 20 vintage homes for sale in Woodstock at a median listing price of $1.09M. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Woodstock stay on the market for 56 days. Popular neighborhoods include Village of Woodstock. This map is refreshed with the newest listings in Woodstock every 15 minutes.

In the past month, 5 homes have been sold in Woodstock. In addition to houses in Woodstock, there were also 9 condos, 0 townhouses, and 0 multi-family units for sale in Woodstock last month. Find your dream home in Woodstock using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Woodstock are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Woodstock. Our Woodstock real estate stats and trends will give you more information about home buying and selling trends in Woodstock. If you're looking to sell your home in the Woodstock area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Woodstock with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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Copyright 2025 PrimeMLS All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this website comes in part from the VOW Program of PrimeMLS. Data last updated Wed Dec 03 2025 on the search page

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