Marlboro Real Estate

Marlboro Real Estate

Welcome to Marlboro, Vermont—a hidden gem nestled in the picturesque Windham County. This charming town, known for its stunning landscapes and tight-knit community, offers a unique blend of rural tranquility and vibrant culture. With a population that values both nature and neighborly connections, Marlboro is the perfect place for those seeking a serene lifestyle away from the hustle and bustle of city life.

Marlboro is renowned for its breathtaking views, with rolling hills and lush forests that change beautifully with the seasons. Outdoor enthusiasts will find an abundance of activities to enjoy, from hiking and biking in the warmer months to skiing and snowshoeing in the winter. The nearby Marlboro College, with its rich history and commitment to liberal arts education, adds a youthful spirit to the town, hosting various cultural events and community gatherings throughout the year.

For those who appreciate the arts, Marlboro boasts a lively arts scene, featuring local galleries, music festivals, and theater performances. The annual Marlboro Music Festival draws visitors from far and wide, showcasing world-class talent in a picturesque setting.

Moreover, the town’s commitment to sustainability and community living is evident in its local farmers' markets and cooperative initiatives, allowing residents to enjoy fresh produce and handmade goods. Whether you’re looking to settle down in a cozy cottage or a spacious family home, Marlboro offers a range of real estate options that cater to diverse lifestyles.

Discover the charm and warmth of Marlboro, Vermont—a place where nature meets community spirit, making it an ideal destination for your next home.

Newest Listings in Marlboro

$2,290,000
5 Beds 9 Baths 5097953 MLS
Discover a once-in-a-generation opportunity to own an extraordinary 745± acre estate in the heart of Southern Vermont. Steeped in centuries of history yet thoughtfully updated for modern living, this remarkable property combines unmatched natural beauty, recreational opportunities, and agricultural potential. The diverse landscape features expansive open fields, mature woodlands, pristine streams, scenic mountains. Miles of historic carriage roads have been transformed into an extensive trail network ideal for mountain biking, hiking, trail running, horseback riding, cross-country skiing, and snowshoeing. Abundant wildlife, a productive sugarbush, and managed timber resources make this an exceptional property for conservation, recreation, or income-producing land management. The 4,400+/1 square foot main residence offers five bedrooms and comfortable, updated living spaces that blend timeless Vermont character with today's conveniences. A charming carriage house includes a private two-bedroom apartment, providing ideal accommodations for guests, family, caretakers, or rental opportunities. An extensive collection of outbuildings offers outstanding flexibility for equestrian pursuits, livestock, woodworking, equipment storage, workshops, or a variety of agricultural and recreational uses. Modern infrastructure includes drilled wells, updated septic systems, a whole-house generator, and high-speed internet, allowing for year-round comfort without sacrificing the property's peaceful rural setting. Conveniently located near renowned ski resorts, shopping, dining, and four-season recreation. Metropolitan areas are easily accessible making this an ideal full-time residence, sporting estate, family compound, working farm, or legacy investment. Properties of this size, quality, and versatility rarely become available. This is a truly exceptional Southern Vermont offering.

634 Lower Dover Rd, Marlboro

$149,000
5095488 MLS
24 improved acres in the hills of Marlboro offering a combination of privacy, accessibility, residential, and recreational potential. Recent driveway improvements have created excellent access into the property, leading to a cleared landing and potential building site set back from the road. Existing recreational and old logging trails meander throughout the acreage and are well-suited for snowmobiling, ATV riding, snowshoeing, hiking, and cross-country skiing, allowing you to enjoy expansive outdoor recreation without ever leaving your own property. The land features rolling and sloping terrain, old stone walls, and the potential for distant ridgeline views with selective clearing. Power is available at the road, and the property has been perk tested for a single-family homesite already with favorable results. Prior selective timber harvesting was completed to encourage the continued health and growth of the woodland. Whitaker Farm Road is a town-maintained road, yet the setting feels removed from it all while being located just moments from Route 9, offering convenient access to Interstate 91, Brattleboro, Massachusetts, New Hampshire, and destinations throughout Southern Vermont. Marlboro is known for its rural character, scenic landscapes, and convenient location between the Green Mountains and the Connecticut River Valley. Should you choose to venture beyond the property, an eclectic array of restaurants, shopping, arts, four-season recreation, ski resorts, and community events can be found throughout nearby towns, offering a wide variety of experiences in every direction. Whether your plans include a year-round residence, vacation getaway, recreational basecamp, or long-term land investment, this property offers already in place improvements and room to create your vision.

381 Whitaker Farm Rd, Marlboro

$675,000
3 Beds 3 Baths 5091535 MLS
Experience the perfect blend of contemporary design and natural warmth in this stunning 2-story hybrid post & beam set on 5 landscaped acres. Thoughtfully designed with soaring ceilings, exposed beams and lots of glass, this light filled retreat brings the outdoors in while offering comfort and style in every season. Inside rich hardwood floors flow throughout the open concept living spaces, anchored by a lovely fireplace and complemented by radiant heat for year-round comfort. The chef's kitchen is designed for both entertaining and everyday living, featuring a beautiful cherry island with sink, soapstone counters and a commercial range with stainless steel hood with heat lamps. Offering 3 bedrooms, 3 baths along with a versatile loft ideal for a home office or studio. Skylights fill the interior with natural light, while screened porches and decks create inviting spaces to relax, dine and enjoy the surrounding landscape. The incredible 2002 addition encompasses and seamlessly elevates the original home. The property backs up to conserved land owned by the Ames Hill-Marlboro Community Center, an entity that has conserved much of the land surrounding South Pond. Take time to enjoy the Marlboro Music Festival and all that Marlboro offers while being accessible to the artsy town of Brattleboro or 4-season recreation options in the resort areas of Wilmington and Dover. This is a rare opportunity to own a distinctive modern country retreat that combines craftsmanship, comfort & serene outdoor living.

2079 Ames Hill Rd, Marlboro

Start Your Search

board logoCopyright 2026 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, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .