Bennington Homes with Shed Exterior Features

**Discover Bennington: A Hidden Gem in Vermont**

Nestled in the picturesque Green Mountains of southwestern Vermont, Bennington is a charming town that seamlessly blends rich history with modern-day amenities. Known for its vibrant arts scene, Bennington boasts a variety of galleries, theaters, and cultural events that draw visitors and locals alike. The town's historical significance is evident in its well-preserved architecture, with landmarks like the Bennington Battle Monument and the Bennington Museum showcasing the area’s storied past. Outdoor enthusiasts will revel in the stunning landscapes that surround Bennington, offering ample opportunities for hiking, skiing, and enjoying the breathtaking fall foliage.

As you explore the real estate opportunities in Bennington, consider homes that feature shed exterior designs. These unique properties often combine rustic charm with modern functionality, creating a warm and inviting atmosphere. Homes with shed exterior features typically showcase sloped roofs and open layouts, providing an appealing aesthetic that harmonizes with the natural surroundings. The versatile design of these homes allows for creative use of space, making them ideal for families, retirees, or anyone seeking a peaceful retreat.

With a growing community and a strong sense of belonging, Bennington is not just a place to live; it’s a lifestyle. Whether you’re drawn to its scenic beauty, rich history, or the distinctive character of shed-style homes, Bennington offers a unique opportunity to create lasting memories in a place you’ll be proud to call home. Explore the possibilities and embrace the charm of this enchanting Vermont town!

Newest Bennington Homes with Shed Exterior Features

$1,695,000

3 Beds ⋅ 3 Baths ⋅ 5105174 MLS

Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom guest cottage. The stunning chef's kitchen is truly the centerpiece of the home, featuring high-end appliances, a dramatic quartz waterfall countertop, and a generous 10-foot island designed for both everyday living and entertaining. Just off the kitchen is a gorgeous screened-in porch, creating a wonderful extension of the living space and the perfect place to enjoy the tranquil setting. Throughout the main level, beautiful white oak floors add warmth and elegance. The home retains the charm and character expected of a historic property while offering the comfort and efficiency of today's modern systems. The thoughtful renovation continues throughout the home, with details such as automated shades in the primary bedroom and library and a convenient second-floor laundry closet. A fireplace adds warmth and character, while expansive views bring the beauty of the surrounding landscape indoors. The separate one-bedroom guest cottage provides even more versatility for guests, extended family, a private office, or potential rental use. Outside, the property is equally impressive, with gorgeous front and side patios designed for outdoor dining and entertaining, a screened-in porch, beautiful grounds, and a storage shed. A rare combination of historic architecture, exceptional renovation, modern technology, expansive acreage, and flexible living spaces, this property offers a level of quality and versatility rarely found in the Bennington market.

1944 Monument Ave, Bennington

$349,000

3 Beds ⋅ 2 Baths ⋅ 5104474 MLS

Tucked into a beautifully maintained neighborhood, 21 Russett Drive is the kind of home that feels welcoming the moment you arrive. Beautiful landscaping, a charming Dutch door, and a thoughtfully cared for yard give this property an almost secret garden feel private, inviting, and full of character. Inside, the versatility of this home truly shines. The main level offers a comfortable living room with striking open wood ceilings that naturally become the focal point of the space, creating a warm setting for relaxing and gathering with family and friends. The kitchen flows easily into the dining area, making everyday meals and entertaining feel effortless. A convenient first floor laundry room adds to the home’s functionality. With three bedrooms and two bathrooms, there is plenty of space for everyone, while the additional den/family room offers endless possibilities. Use it as a family room, playroom, home office, guest space, or even a first floor bedroom the choice is yours. Upstairs, one of the bedrooms could easily be transformed into a dedicated office, reading room, or creative space. Step outside onto the new deck and enjoy a backyard that has been lovingly landscaped and maintained, offering a wonderful extension of the home’s living space. Served by town water and septic, this property has been meticulously cared for and is truly move in ready. Its thoughtful layout, flexible spaces, inviting outdoor areas, and ability to adapt as your needs change make 21 Russett Drive a home you can settle into today and continue to make your own for years to come. A home with character, versatility, and room to grow this is one you’ll want to see.

21 Russett Dr, Bennington

$475,000

3 Beds ⋅ 3 Baths ⋅ 5102749 MLS

Welcome to this beautifully maintained Cape-style home in the desirable Pine Meadows neighborhood of Bennington. At only 6 years young and meticulously maintained, this move-in ready home offers the perfect combination of modern construction, energy efficiency, and comfortable living space. The thoughtfully designed floor plan features a sought-after first-floor primary suite with a walk-in closet and private full bath, providing the convenience of single-level living. The bright, open-concept kitchen, dining, and living areas create an inviting space for everyday living and entertaining. Just off the kitchen, a stunning 10' x 20' sunroom extends your living space and serves as the perfect spot to enjoy morning coffee, unwind with a book, or host guests. With direct access to the backyard, it creates a seamless connection between indoor and outdoor living. Upstairs, you'll find two additional bedrooms both with walk-in closets and a full bath between them, while the finished lower-level bonus room offers excellent flexibility as a family room, home office, fitness area, or hobby space. Year-round comfort is provided by an efficient Buderus boiler and a five-head mini-split system offering heating and cooling throughout the home. Additional highlights include a two-car attached garage, generator-ready electrical setup, paved driveway, first floor laundry, and a beautifully maintained one-acre lot offering space to relax, garden, and enjoy the outdoors. Conveniently located just minutes from downtown Bennington, Antrim, Peterborough, hiking trails, golf, and the many amenities of the Monadnock Region, this exceptional home offers the ideal balance of peaceful neighborhood living and modern convenience. With quality construction, thoughtful upgrades, and meticulous care throughout, this is a home you'll be proud to own.

82 Pine Meadows Cir, Bennington

$739,900

3 Beds ⋅ 3 Baths ⋅ 5102468 MLS

Owner-built and thoughtfully maintained, this spacious home offers room for everyone with three bedrooms, three bathrooms, a three-car direct-entry garage with a walk-up attic, and equestrian amenities including a three-stall stable, fenced pasture, and nearby area trails. Follow the slate walkway to the 16' x 25' storage barn, or enter from the covered porch and enjoy the quiet surroundings. Inside, a bright and welcoming foyer opens to a staircase and balcony hall, a private living room with a rock-faced wood-burning fireplace, and a formal dining room with wainscoting. The kitchen features stainless steel appliances, granite countertops, a pantry closet, desk area, breakfast bar, and a sunny breakfast nook that flows into the family room and out to the 11' 15" x 31' 2" rear deck overlooking an owner’s garden area. Hardwood and tile flooring run throughout the home, and all floors are heated with oil-fired radiant heat. The newly renovated primary bath includes a walk-in shower, double sinks, cabinetry with linen storage, tile flooring, and fresh paint throughout. The basement-level recreation room features new flooring, a built-in entertainment center, and a newly constructed bar area with a sink. The walk-out basement also provides an ideal shop or workspace. A place for everyone, this property is only moments from the center of Bennington, skiing at Crotched Mountain, Crotchet Mountain Golf Club and just 4 miles from NH Route 202.

97 Onset Rd, Bennington

$132,900

2 Beds ⋅ 1 Baths ⋅ 5101539 MLS

Very well kept single-wide mobile home on it's own land. Cozy 2 bedroom, 1 bathroom home with single level living. Living room, kitchen with dining area, main level laundry and more. Has 2 enclosed porches. The smaller one is used as a pantry and the larger one is heated. Outside 2 sheds and the sounds of the nearby babbling brook. Also has RV electric hook up.

60 Tori Ln, Bennington

$259,000

4 Beds ⋅ 2 Baths ⋅ 5098985 MLS

Well maintained and thoughtfully updated, this 4-bedroom, 2-bath home offers the ease of single-level living on a beautiful level one-acre lot in Bennington's desirable west end. Enjoy stunning mountain views from the spacious back deck or sip your morning coffee on the covered front porch. Inside, you'll find an updated kitchen, refreshed bathrooms, a cozy fireplace, central air conditioning, a 2023 roof, an updated heating system, and a spacious primary suite featuring a jetted step-in tub and separate shower. Offering the perfect blend of comfort, convenience, and low-maintenance living, there's also room to add your own personal touches over time. Enjoy a peaceful setting just minutes from downtown Bennington for dining, shopping, cultural attractions, and everyday conveniences, with easy access to multiple ski destinations. Conveniently located approximately one hour from Albany International Airport and about three hours from both New York City and Boston.

549 Houran Rd, Bennington

$249,900

5095558 MLS

Bring this historic gem back to life and unlock its incredible potential! Rich with the timeless character and charm of a late-1800s home, this unique property features spacious rooms and many original architectural details waiting to shine again. The building includes three two-bedroom units, including a generously sized two-story unit with a kitchenette and full bathroom on the upper level. Enjoy a large covered front porch, private off-street parking in the rear, and a storage shed for added convenience. Ideally located near downtown shopping, restaurants, recreation facilities, and public transportation, this property offers both charm and accessibility. Whether you're an investor, renovator, or someone with a vision, this is a rare opportunity to build equity and restore a piece of history. With strong income potential and endless possibilities, this property is ready for its next chapter. Don't miss out!

406-408 Gage St, Bennington

$550,000

5 Beds ⋅ 2 Baths ⋅ 5088350 MLS

Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home. Situated on over 17 acres, this property offers not one but two barns, established fenced pastures, and the kind of setting that feels like a Vermont dream. Listen to the breeze move through the grass, watch the leaves change color in the fall, and enjoy the privacy and beauty that surround you. Inside, you’ll find five bedrooms and two full bathrooms, with space that invites family dinners, holiday gatherings, and everyday moments that make a house feel special. The usable basement offers excellent storage, workshop potential, tool space, or room for tack and farm equipment. Whether you have horses, farm animals, or simply want the charm and comfort of country living, this property offers the Vermont lifestyle so many people dream about. This is more than a house it’s the feeling of finally coming home.

971 S Stream Rd, Bennington

$209,900

2 Beds ⋅ 1 Baths ⋅ 5086144 MLS

Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a large garage with an attached storage shed and ample paved parking.

1083 Main St, Bennington

Start Your Search

board logo Copyright 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 .