Windham County (Southeastern Vermont) has 23 towns ranging in population from a few hundred to 12,000. The larger population centers of Brattleboro and Bellows Falls have more jobs and housing options, but many people live in smaller towns and commute for both work and play. Putney, Guilford, and Vernon are all close to Bratt, and the picturesque West River Valley towns of Dummerston, Newfane, and Townshend also offer an easy drive or cycle along VT-30. Mountainous areas like Dover, Wilmington and Marlboro are more insulated by hilly terrain, making daily commutes more adventurous.

The local housing market is tight, so you’ll want to team up with a knowledgeable realtor who can (1) explain the ins and outs of SoVermont real estate, (2) view and send you digital tours of potential properties, and (3) help you craft winning offers (be prepared to make a few of these). You can peruse Zillow and sign up for alerts, but not all available properties are listed. Check out the Berkley & Veller site for more options, and even tune into town Facebook groups.
Try to get to know the different towns so you can hone in on your preferred locations and meet a realtor working there. Your agent should make you feel comfortable and confident, so don’t be afraid to speak with a few until it’s a good fit. You can find realtors on Chamber of Commerce websites (i.e. Brattleboro, Bellows Falls, Wilmington), or reach out to us and we’ll send some recommendations.

Since Southern Vermont doesn’t have many apartment complexes, finding a rental may require some legwork. Facebook Marketplace is a good place to start, but many rentals go unadvertised. You can try reaching out to these local property managers about openings: Southern VT Property Management, Heim Properties, Green Mountain Rentals.
A great resource for those looking for affordable housing solutions is Windham & Windsor Housing Trust. It may also be worth joining town Facebook groups (i.e. Brattleboro, Dover/Wilmington, and Newfane) and posting a little about yourself and what you're looking for.

Because it can sometimes take a while to find the right long-term place, consider lining up something short-term so you can get here faster and get to know the area. Many vacation rentals are willing to offer a monthly rate–try AirBnB, VRBO, and Furnished Finder.
If life circumstances and personality allow for it, renting a room in someone’s house could be an affordable way to go. Room-lets are typically listed on Facebook Marketplace and Craigslist, or you might look into the HomeShare Vermont program. If you already have friends in Vermont, ask them to post what you’re looking for on Front Porch Forum, along with a bit about you.

Southern Vermont has a variety of options when it comes to childcare, including many nature-based & specialty preschools. And unlike many other places, enrolling your child doesn’t usually involve a lengthy waitlist. Winston Prouty offers a childcare referral service that can help you discover what’s available locally. After a quick call where you tell them what you’re looking for, they’ll send you a list of licensed childcare centers and preschools that fit your criteria. You can request they pull the list as many times as you need, so feel free to request it even if you’re not serious yet.
Vermont is leading the way in supporting parents with young children. There is a statewide childcare subsidy that helps individuals pay for childcare from birth through age 12. You must have an accepted service need (including employment or education) and meet the income guidelines, but even moderately high-income families qualify. Vermont also has a Universal Pre-K Program, which subsidizes 10 hours a week of preschool once your child is three. Enroll with a prequalified preschool and they will help you sign up. For help understanding these subsidies, it may be worth asking the kind folks at Winston Prouty.

Public schooling in Vermont is marked by small class sizes and some of the highest spending per student, which helps ensure equal education outcomes. In Windham County (Southeast Vermont) there are four school districts: Windham Southeast, Windham Northeast, Windham Southwest, and Windham Central. This map breaks down each district in the state by town.
Many towns have a dedicated K-5 school, but families can elect to send children to other schools within the district. At the middle and high school levels, one school per district is more common. High School in Vermont has open enrollment, meaning students can choose to attend any public high school (with some limitations). If you live in a town without a dedicated school, the state will provide a tuition stipend to send students to a public or approved independent school of their choice.
Enrichment activities vary by individual school and district, but area schools tend to emphasize arts, nature and project-based learning, and most offer traditional extracurricular activities and afterschool programs. Some schools have winter sports programs– blocks of time dedicated to enjoying winter activities like skiing, snowboarding and ice skating, or other activities. To learn more about what a school offers, reach out to the administrator, who can answer questions and possibly provide you with a tour of the school.
Southern Vermont has a number of private and independent schools– from specialty elementary schools to respected private boarding schools, and everything in between. There are options for faith-based, nature, arts and experiential education, as well as Montessori and Waldorf schools. Some of the more well-known private schools include the Putney School, Vermont Academy, the Greenwood School, and Burr & Burton Academy.
Those interested in homeschooling will find a well-established community and support network in SoVermont. Check out the Southern Vermont Homeschoolers website and join local homeschooling Facebook groups to get to know more about what’s available. Local libraries, and the Putney Library in particular, are great places to look for resources.

Brattleboro Memorial Hospital and smaller Grace Cottage Hospital in Townshend are the medical centers located in Windham County. Each offers primary care plus emergency and specialty care. Brattleboro Retreat offers outpatient and inpatient comprehensive mental healthcare. There are many other local options, from independent practices to alternative medicine. Beyond Windham County, Cheshire Medical Center in Keene, NH and Dartmouth Hitchcock Medical Center in Lebanon, NH both provide excellent care. Baystate Franklin Medical Center is another option just 30 minutes from Brattleboro in Greenfield, MA.
Your health insurer’s directory is a good place to look for healthcare providers who are in-network and accepting new patients. For more specialized care, you might ask for recommendations from neighbors, or look on Front Porch Forum and town Facebook groups. It’s not a bad idea to get on new patient waiting lists before your move date since it may take some time to move up the list.
Check if your current health insurance plan covers services in Southern Vermont. Blue Cross Blue Shield of Vermont and MVP Health Care are the qualified insurance providers through the state’s marketplace. Other major insurance companies with a presence in Vermont include UnitedHealthcare and Aetna.
Vermont Health Connect, the state’s health insurance marketplace, is a great place to compare insurance plans and see if you qualify for tax credits or programs like Medicaid and Dr. Dynasaur (for children and pregnant people). Moving to Vermont opens up a special period of enrollment for insurance through the marketplace– more information can be found here.

Finding employment in Southern Vermont may not be quite as straightforward as it is in major markets. But if you are open to it, moving here may lead to unexpected opportunities like entrepreneurship or changing your career path.
What we do know is that there is a better work-life balance here. Plus, we are here to help, whether you need to find a job in the area, are bringing your job with you, or you want to start your own business.

Brattleboro Development Credit Corporation
76 Cotton Mill Hill, Brattleboro, VT 05301 | 802.257.7731 x 218 | info@brattleborodevelopment.com
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