Roxbury Real Estate

Welcome to Roxbury, a vibrant neighborhood nestled in the heart of Boston, Massachusetts. Known for its rich history and diverse culture, Roxbury offers a unique blend of urban living and community spirit. With roots tracing back to the 17th century, this area is steeped in historical significance, making it a fascinating place to call home.

Roxbury is celebrated for its resilient community and a strong sense of identity. The neighborhood features a variety of architectural styles, from charming Victorian homes to modern developments, catering to a range of tastes and lifestyles. Residents enjoy easy access to beautiful parks, local markets, and a thriving arts scene, with numerous galleries and cultural events that showcase the talents of local artists.

Conveniently located, Roxbury provides seamless connectivity to downtown Boston and beyond, making it an ideal spot for commuters. The area is well-served by public transportation, including the subway and bus routes, ensuring that you’re never far from the city’s bustling amenities.

Education is a priority in Roxbury, with a number of reputable schools and educational institutions nearby, making it an excellent choice for families. The community is also known for its commitment to social justice and empowerment, fostering a welcoming environment for residents from all walks of life.

Whether you’re looking for a cozy apartment or a spacious family home, Roxbury has something to offer everyone. Experience the charm of this historic neighborhood and discover why so many choose to make Roxbury their home. Come explore the possibilities that await you in this dynamic community!

Newest Listings in Roxbury

$996,000

3 Beds ⋅ 3 Baths ⋅ 5110742 MLS

Perfectly positioned for year-round recreation, you'll enjoy hiking, biking, fishing & nearby swimming holes in summer, with Sugarbush just 15+ minutes away and Mad River Glen, Stowe, the Middlebury Snow Bowl & Killington within easy reach. More than a home, this is a carefully curated Vermont sanctuary where woods & gardens invite you to relax, recharge, and experience the very best of Vermont living. Tucked away on 11+ wooded acres in Roxbury and mid-way between I-89 Exits 4 or 5 & Sugarbush, this extraordinary retreat is where craftsmanship, nature, and thoughtful design come together in perfect harmony. The property is packed with functional & luxury appointments lovingly created by its owners these past 20+ years as built by local craftsmen at Ritzer & Associates. Both the home & barn showcase custom maple cabinetry, premium appliances, beautifully finished baths, timeless materials & more throughout. Built in 2005 as a vacation home, the welcoming kitchen opens to a cozy living room anchored by a beautiful stone hearth and wood insert. A main-level bedroom and ¾ bath provide comfortable guest accommodations, while the spectacular screened porch with a stone fireplace grill is destined to become your favorite gathering place. The loft-style primary suite offers a peaceful escape & the dry snug basement is partially finished. The home is complemented by a 2-vehicle barn added in 2015 with a later finished ADU above, beautifully designed gardens, a charming garden shed, a custom chicken coop, a 3-bay equipment shed and inviting woodlands. A 20kW Kohler propane generator with a grid tied 40 panel solar array & 2 Tesla Powerwall 3’s provide electrical resiliency & savings. A Level 2 car charger’s onsite & TDS fiber is available. From the moment you turn off Town maintained West Hill Road, you'll know you've arrived somewhere special as every inch of this retreat reflects a passion for intentionally weaving exceptional quality into a peaceful Vermont lifestyle.

1369 W Hill Rd, Roxbury

$415,000

3 Beds ⋅ 2 Baths ⋅ 5110565 MLS

This is a spacious 3-bedroom 2 bath ranch on 5.79 acres with complete privacy. Livingroom and dining room provide plenty of space for gatherings and the kitchen is large enough to accommodate your table. The bedrooms are spacious with plenty of closet space. The screen porch and deck overlook the backyard with a view to the woods. There is a one car attached garage and brand new oversized two car garage with a room for a workshop in the back as well as a huge space above waiting for your imagination. Storage? Game room? Or perhaps future living space. Hop on the trails right outside your door and enjoy a quiet hike on the abandoned railroad bed. This is a great location, with easy access to Keene with all amenities and services you and your family need and it’s a quiet and peaceful setting that will rejuvenate you.

245 Branch Rd, Roxbury

$699,000

3 Beds ⋅ 2 Baths ⋅ 5110475 MLS

Some Vermont properties just hit differently. Set on 87 private acres with southern exposure, mountain views, rolling meadow, streams, woods, and direct access to outdoor adventure, this Roxbury cottage is equal parts peaceful retreat and practical escape. Tucked off a town-maintained dead-end road, the setting feels wonderfully removed, yet Warren, Waitsfield, skiing, dining, and the Mad River Valley are all within easy reach. Spend slow mornings on the wraparound porch, afternoons exploring trails, and evenings watching the light move across the mountains. Inside, the home is warm, simple, and full of character, with 2 bedrooms, 1 bath, a loft, a charming country kitchen, Andersen windows, Hardie Plank siding, a standing seam roof, updated plumbing, and high-speed internet. Water supplied by it's own natural spring fed water. The lower level has been converted into additional living space with its own bedroom, bath, kitchen, and laundry, offering flexibility for guests. With direct access to hiking, VAST snowmobile trails, quad trails, and 87 acres to roam, this is a rare Vermont real estate opportunity for anyone seeking privacy, beauty, recreation, and room to breathe. Full-time residence, weekend retreat, homestead, or vacation rental potential, this one has the kind of setting people search for and almost never find.

121 Fisher Rd, Roxbury

$725,000

3 Beds ⋅ 2 Baths ⋅ 5106759 MLS

Set on 44.8 acres of quintessential Vermont landscape and within easy reach of Sugarbush Resort, 1641 West Hill Road offers a rare combination of acreage, privacy, and year-round recreation. Whether you are drawn to skiing, hiking, hunting, snowshoeing, gardening, or simply having room to explore, this property delivers the space and freedom of a true Vermont retreat. The approximately 2,772-square-foot log home blends rustic character with flexible everyday living. A hand-built stone fireplace anchors the main living area, complemented by natural wood tones, generous gathering spaces, and views of the surrounding landscape. The main level offers a spacious kitchen and dining area, comfortable living space, a bedroom, and a bath. Upstairs are additional bedrooms, another bath, and a small landing or loft area ideal for a reading nook, office, or sitting space. The partially finished basement adds versatility for a home gym, game room, hobby space, media room, workshop, or additional relaxation area. Outside, the nearly 45 acres are the defining feature, offering room to create trails, keep animals, enjoy the woods, or simply preserve the privacy and natural setting. A detached barn provides useful space for equipment, storage, recreational gear, or projects, while the attached garage adds year-round convenience. Privately situated yet within reach of Sugarbush, Norwich University, I-89, and Central Vermont amenities, this is an opportunity to own a substantial piece of Vermont with the land, character, and flexibility to make it your own.

1641 W Hill Rd, Roxbury

$425,000

5103451 MLS

Discover the possibilities on 85 acres of elevated Vermont land in Roxbury. Set high on the hillside, this expansive property offers privacy, natural beauty and exciting development potential. Preliminary engineering has been completed, indicating the potential for up to eight homesites, subject to all required permits and approvals. Access would likely be established from Warren Mountain Road. Conveniently located near the renowned Windridge Tennis & Sports Camp, Northfield Country Club and within reach of Norwich University, this unique parcel presents an opportunity for development, a private estate or a long-term investment. Buyers are responsible for conducting their own due diligence regarding access, permitting, subdivision and intended use.

Lot 0 Roxbury, Roxbury

$315,000

3 Beds ⋅ 2 Baths ⋅ 5101779 MLS

Welcome to this charming three-bedroom, one-and-a-half-bath home nestled on 2.57 picturesque acres in the heart of Roxbury, Vermont. Offering the perfect blend of country charm and everyday comfort, this property provides a peaceful setting with plenty of room to enjoy the outdoors. A welcoming covered porch leads into a functional layout featuring an open kitchen and dining area, ideal for gathering with family and friends. The spacious living room is filled with natural light and offers easy access to the backyard, while the first-floor primary bedroom adds convenience and flexibility. Upstairs, you'll find two additional bedrooms and a full bath, providing ample space for family, guests, or a home office. Outside, the beautifully landscaped grounds offer room for gardens, recreation, or simply relaxing while taking in the quiet Vermont surroundings. Located just minutes from Northfield and an easy drive to Montpelier, Sugarbush Resort, Mad River Glen, hiking trails, and VAST trail access, this home is perfectly situated for year-round outdoor enthusiasts. Whether you're looking for a full-time residence or a peaceful Vermont getaway, 711 Northfield Road offers country living with convenient access to everything Central Vermont has to offer.

711 Northfield Rd, Roxbury

$399,900

6 Beds ⋅ 3 Baths ⋅ 5097966 MLS

Competitively priced and packed with potential, this rare 24-acre off-grid Vermont property offers the perfect blend of privacy, space, character, and versatility. The main home features a spacious layout with a dramatic great room centered around a brick hearth and wood stove, an open kitchen, updated bathrooms, a generous primary suite, and multiple additional bedrooms. A detached gambrel-style barn adds exceptional value with an oversized two-car garage/workshop and a beautifully finished upper-level living space complete with a full kitchen, open living area, and private deck overlooking the surrounding woods. Designed for independent living, the property operates off-grid and includes approximately $80,000 in newly installed solar panels and $30,000 worth of wood stoves, providing exceptional energy efficiency and reliable year-round comfort. Whether you're looking for a private retreat, space for an extended household, or room for hobbies and recreation, this is a property that stands apart. It won't last!!

1081 Beaver Meadow Rd, Roxbury

$99,000

5091664 MLS

Secluded 68-acre wooded lot surrounded by Roxbury State Forest, and accessible only by the VAST snowmobile trail or on foot. The land is mostly hardwoods, last logged about 10 years ago, and supports abundant wildlife. Currently enrolled in Vermont's Current Use Program, offering tax benefits for conservation; buyers should do their due diligence regarding the process and penalties for withdrawing land from the program if planning to build a cabin or other structures. Ideal for a remote getaway, hunting, or investment in wilderness land.

00 Beaver Meadow Rd, Roxbury

$139,900

5079568 MLS

ATTENTION Nature Enthusiasts! Unfinished log dwelling with wood frame addition on an especially pleasant square-ish shaped, surveyed 18.06 acre, lightly-wooded rural parcel that fronts on a town-maintained road. Rural mail delivery through Northfield PO. Roxbury town plow's turnaround is only 100'+/- before subject property's driveway, so very short section of roadway is privately maintained by users. Sizeable covered porch. Somewhat level spread of land in the vicinity of the structure. WEC power pole across road. No water service to, nor sewage disposal systems in place. Well aged Elm wood stove has provided heat, included "as is" with no warranty. Roughly half of the parcel has a conservation easement, a copy of which, along with the subdivision and deed are all attachments to this listing, and should be reviewed. Being sold in "as is" condition with remaining building materials included in the sale. Call your REALTOR to let them know when you'd like a tour of the property so that they can accompany you.

397 Winch Hill Ext, Roxbury

$139,900

5079438 MLS

ATTENTION Nature Enthusiasts! Unfinished log dwelling with wood frame addition on an especially pleasant square-ish shaped, surveyed 18.06 acre lightly-wooded rural parcel the fronts on a town-maintained road at the far end of Winch Hill (Rural mail delivery thru Northfield PO, and Roxbury town plow's turnaround is only 100'+/- before driveway, so very short Class 4 road to maintain). Sizeable covered porch (12'4x24'6+13'9x19'3). Somewhat level spread of land in the vicinity of the structure. Washington Electric Power pole across road. No water service to, nor sewage disposal system in place. Well-aged Elm wood stove has provided heat, included "as is; no warranty". Roughly half of the parcel is part of a Conservation Easement, a copy of which is attached to this listing, along with the land use permit and deeds. House is being offered in "as is" condition with remaining building materials included in the sale. Take special care during showings and please let your REALTOR know when you'd like to take a look so they can accompany you.

397 Winch Hill Ext, Roxbury

$125,000

5079350 MLS

Your Vermont dream starts here. This stunning 10.66-acre parcel offers the perfect canvas for building your mountain retreat, with power already at the road and a septic design ready to go. Rolling terrain and endless outdoor space invite you to imagine boundless possibilities beneath towering green canopies. Nestled just south of charming Roxbury village, you're a scenic drive from Sugarbush Resort and Mad River Glen for world-class skiing, while Roxbury State Forest provides year-round adventure right in your backyard. Norwich University sits nearby for cultural enrichment. Few opportunities remain to claim this much unspoiled Vermont acreage with infrastructure already in place. Seize your slice of the Green Mountains today.

Lot 3 Thurston Hill, Roxbury

$125,000

5079257 MLS

Your Vermont dream starts here. This stunning 10.21-acre parcel offers the perfect canvas for building your mountain retreat, with power already at the road and a septic design ready to go. Rolling terrain and endless outdoor space invite you to imagine boundless possibilities beneath towering green canopies. Nestled just south of charming Roxbury village, you're a scenic drive from Sugarbush Resort and Mad River Glen for world-class skiing, while Roxbury State Forest provides year-round adventure right in your backyard. Norwich University sits nearby for cultural enrichment. Few opportunities remain to claim this much unspoiled Vermont acreage with infrastructure already in place. Seize your slice of the Green Mountains today.

Lot 1 Thurston Hill, Roxbury

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