Shaftsbury Homes for Sale

/46
$895,000
- 5 Beds
- 2 Baths
- 2,424 Sq Ft
2 Cold Spring Rd, North Bennington, VT 05257

Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 810-8434

2 Cold Spring Rd, North Bennington, VT 05257
/60
$1,950,000
- 4 Beds
- 3.5 Baths
- 3,333 Sq Ft
1268 Myers Rd, Shaftsbury, VT 05262

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, a 2 car garage, top notch equestrian facilities, a trout and koi pond, and the list goes on and on. The winding driveway leads to a world away, as it opens to view of the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF

Laura Beckwith

Josiah Allen Real Estate, Inc.

(802) 441-6014

1268 Myers Rd, Shaftsbury, VT 05262
/36
$499,900
- 3 Beds
- 2 Baths
- 1,520 Sq Ft
1061 Granger Hollow Rd, North Bennington, VT 05257

Dreaming of a peaceful Vermont lifestyle? This three bedroom, 2 bath home sits on 11.5 acres of beautiful land with rolling open mountain views, a stream, mature apple trees, and an inground pool all the ingredients for your perfect retreat.Step inside to this home that has had a complete refresh. The home offers a first floor bedroom and full bath with a step in shower, making it great

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 481-3292

1061 Granger Hollow Rd, North Bennington, VT 05257
/59
$1,150,000
- 3 Beds
- 3 Baths
- 2,462 Sq Ft
636 Dexter Rd, Shaftsbury, VT 05262

In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

Kristin Comeau

TPW Real Estate

(802) 520-1220

636 Dexter Rd, Shaftsbury, VT 05262
/13
$199,000
- 3 Beds
- 2 Baths
- 1,200 Sq Ft
2017 East Rd, Shaftsbury, VT 05262

3 bedroom 2 bath, double wide on 1.49 acres in Shaftsbury. Offering good location, large yard, and convenient travel to town. Living room with new pellet stove, kitchen with modern appliances including newer stove and dining area. Outside a 2 car detached garage, storage sheds and front and rear porches. New carpet.

Max Squiers

KW Vermont - Brenda Jones Real Estate Group

(802) 798-5968

2017 East Rd, Shaftsbury, VT 05262
/59
$699,000
- 3 Beds
- 2.5 Baths
- 3,637 Sq Ft
272 Oak Hill Rd, Shaftsbury, VT 05262

Built in 2001, this stunning contemporary home sits on just under 8 peaceful acres and offers a perfect blend of space, light, and comfort. The grand two-story living room features soaring ceilings and a cozy pellet stove, creating an impressive focal point. The first floor offers a spacious primary suite for ultimate convenience, along with a dedicated home office—perfect for remote work or

Faith Rhodes Maple Leaf Realty

272 Oak Hill Rd, Shaftsbury, VT 05262
/48
$685,000
- 3 Beds
- 2.5 Baths
- 1,738 Sq Ft
1516 W Mountain Rd, Shaftsbury, VT 05262

Discover your dream retreat in this immaculate 3-bedroom, 3-bath, single level home, nestled on over 4 acres of breathtaking landscape. Enjoy expansive mountain views of the Taconic range, Bennington Monument, and Mount Graylock. Relax on the spacious deck or in the screened-in porch, soaking in the stunning vistas. This updated one-level home, features hardwood floors throughout and an open

Margretta Fischer Wohler Realty Group

1516 W Mountain Rd, Shaftsbury, VT 05262
/36
$498,000
- 3 Beds
- 2 Baths
- 1,671 Sq Ft
6 Dwyers Camp Rd, Shaftsbury, VT 05262

Discover quintessential Vermont living in this charming home, ideally situated on 6.9 serene acres in scenic Shaftsbury, a picturesque town in Southern Vermont. This meticulously maintained residence offers a blend of rustic charm and modern sophistication, providing a tranquil retreat with convenient access to area amenities and attractions. Thoughtful renovations have elevated its interior,

Lori Hurley Four Corner Properties LLC

6 Dwyers Camp Rd, Shaftsbury, VT 05262
/50
$425,000
- 3 Beds
- 2 Baths
- 1,941 Sq Ft
97 Buck Hill Rd, Shaftsbury, VT 05262

Two homes on 4.67 acres in Shaftsbury, VT! This village home offers a rare opportunity indeed by including a separate 2 bedroom ranch home as well. The main home is a charming New England farmhouse with 3 bedrooms and 2 bathrooms, living room, formal dining room, kitchen, main level laundry and so much more. The accessory dwelling unit offers 2 bedrooms, 1 bathroom, eat-in kitchen and living

Brenda Jones KW Vermont - Brenda Jones Real Estate Group

97 Buck Hill Rd, Shaftsbury, VT 05262
/54
$1,995,000
- 3 Beds
- 3 Baths
- 5,228 Sq Ft
2167 Myers Rd, Shaftsbury, VT 05262

Welcome to Hidden Ponds Farm!!! Nestled amidst 40 sprawling acres, this historic early 1800's post and beam converted barn is a rare gem combining rustic charm with modern comforts. The property is highlighted by a stunning 1,000-foot hand-placed stone wall, two picturesque ponds, and two orchards offering seasonal beauty and fresh fruit. The expansive outdoor space also features a hot tub,

Kelley Mccarthy Mahar McCarthy Real Estate

2167 Myers Rd, Shaftsbury, VT 05262
/2
$199,500
- Land
- 47 Acres
- $4,245 per Acre
TBD Myers Rd, Shaftsbury, VT 05262

47+/- magical acres of rolling meadows, mountain views, hard woods and wildlife. The acreage affords you the opportunity to build your dream home/mini farm. The expansive acreage invites you to explore the surrounding nature, whether it's a morning walk on the bucolic rural road, greeting the early birds or sitting high on the hillside staring at the stars. Few parcels of this size remain

Carol O`Connor Four Seasons Sotheby's Int'l Realty

TBD Myers Rd, Shaftsbury, VT 05262
/52
$429,000
- 4 Beds
- 2 Baths
- 2,368 Sq Ft
263 Elm St, North Bennington, VT 05257

Fabulous Four Bedroom Farmhouse. Updated kitchen with new stainless steel appliances. Take in the mountain view through your newer windows over the new stainless steel sink and subway tile backsplash. Natural light floods this spacious home. The first-floor primary bedroom has a private walk-out deck overlooking the large level backyard. The generous living room opens up to a dining area just off

Margretta Fischer Wohler Realty Group

263 Elm St, North Bennington, VT 05257
/2
$49,000
- Land
- 8 Acres
- $5,904 per Acre
0 Glastenbury Rd Unit 5019171, Shaftsbury, VT 05262

Wooded lot on Shaftsbury / Glastenbury line.

Christiane Carroccio TPW Real Estate

0 Glastenbury Rd Unit 5019171, Shaftsbury, VT 05262

Vermont Shaftsbury Shaftsbury

Frequently Asked Questions Why Live in Shaftsbury

Is Shaftsbury a good place to live?

Shaftsbury is a good place to live. Shaftsbury is considered very car-dependent and somewhat bikeable. Shaftsbury is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Shaftsbury has 2 parks for recreational activities. It has a median age of 49. The average household income is $117,967 which is above the national average. College graduates make up 37.2% of residents. A majority of residents in Shaftsbury are home owners, with 15.4% of residents renting and 84.6% of residents owning their home. A local real estate agent serving Shaftsbury can help you decide if this neighborhood is the right one for you. Learn more on our Shaftsbury neighborhood guide.

Is Shaftsbury, VT a safe neighborhood?

Shaftsbury, VT 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 Shaftsbury?

The median home price in Shaftsbury is $498,950. If you put a 20% down payment of $99,800 and had a 30-year fixed mortgage with an interest rate of 6.75%, your estimated principal and interest payment would be $2,590 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $111K a year to afford the median home price in Shaftsbury. The average household income in Shaftsbury is $118K.

What are the best public schools in Shaftsbury?

The best public schools that serve Shaftsbury are:

Mt. Anthony Union High School has a C+ Niche grade, a student teacher ratio of 16:1 and an average review score of 3.3.
Mt. Anthony Union Middle School has a C Niche grade and a student teacher ratio of 14:1.
Shaftsbury Elementary School has a C- Niche grade and a student teacher ratio of 13:1.

What are the best private schools in Shaftsbury?

The best private schools that serve Shaftsbury are:

Green Mt. Mennonite School has a student teacher ratio of 7:1.
Village School of No.Bennington has a student teacher ratio of 8:1.

What are the most popular zip codes in Shaftsbury, Shaftsbury, VT?

The most popular zip codes in Shaftsbury, Shaftsbury, VT include 05262, 05257, 12057, 05201 and 05250.

Learn more about living in Shaftsbury

Home Trends in Shaftsbury, VT

On average, homes in Shaftsbury, VT sell after 49 days on the market compared to the national average of 51 days. The median sale price for homes in Shaftsbury, VT over the last 12 months is $455,000, up 21% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$455,000

Median Single Family Sale Price

$495,000

Average Price Per Sq Ft

$280

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

5.00

Median List Price

$498,950

Median Change From 1st List Price

Median Home Sale Price YoY Change

21%

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Copyright 2025 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is 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.