Bennington Homes with Garden Exterior Features

Welcome to Bennington, Vermont—a charming town nestled in the heart of the Green Mountain State. With its rich history, vibrant arts scene, and stunning natural landscapes, Bennington is the perfect blend of small-town charm and modern convenience. Known for its picturesque downtown area, complete with quaint shops, delightful eateries, and historic landmarks, Bennington offers a welcoming atmosphere that makes it a wonderful place to call home.

One of the standout features of homes in this idyllic town is their beautiful garden exterior. Imagine stepping out of your front door into a lush, vibrant garden, where the air is filled with the sweet scent of blooming flowers and the soothing sounds of nature. Homes with garden exteriors not only enhance the aesthetic appeal of the property but also provide a serene escape right at your doorstep. Whether you’re a seasoned gardener or simply someone who appreciates the beauty of nature, these homes offer an enchanting outdoor space that invites you to relax, unwind, and enjoy the tranquility of your surroundings.

In addition to the stunning gardens, Bennington's properties often boast spacious layouts, modern amenities, and a sense of community that is hard to find elsewhere. With nearby parks, hiking trails, and cultural attractions, residents can embrace an active lifestyle while enjoying the breathtaking views that Vermont is famous for.

Discover the charm of Bennington and explore the homes that feature beautiful garden exteriors—your dream home awaits in this picturesque corner of Vermont!

Newest Bennington Homes with Garden Exterior Features

$695,000

4 Beds ⋅ 4 Baths ⋅ 5111572 MLS

Welcome to a home that truly has room for it all! Set in a desirable neighborhood on a beautifully landscaped lot, this impressive property offers an incredible amount of living space inside and out. A paved driveway leads to the attached two-car garage, while the backyard feels like your own private retreat with a gorgeous inground pool, spacious patio and beautiful yard perfect for entertaining or simply enjoying summer at home. Inside, you’ll find generously sized rooms and a layout designed for both everyday living and gathering. The kitchen features granite countertops, plenty of cabinetry and a pantry, while the huge family room is made for entertaining with its own bar area and a cozy pellet stove set into the fireplace. A bright sunroom opens directly to the backyard patio and pool, creating wonderful indoor-outdoor flow. The first-floor primary suite offers the convenience of one-level living, complemented by first-floor laundry, a full bath and a handsome office with built-ins. Upstairs, there are plenty of bedrooms plus additional unfinished space above the garage offering even more possibilities: although with this much space, you may never need it! And there’s still more downstairs. The beautifully finished basement adds an entire additional level of living and recreation space, including a game room, home gym, fireplace and plenty of room to spread out. From the expansive interior to the pool, patio and gorgeous grounds, this is a home designed for living big, entertaining well and enjoying every season.

370 Southshire Dr, Bennington

$219,000

2 Beds ⋅ 1 Baths ⋅ 5111442 MLS

As the old saying goes... LOCATION, LOCATION, LOCATION! Situated on a large corner lot in the desirable village of North Bennington, this one level home is brimming with potential. There is plenty of space inside and several rooms that can be configured to fit your needs. The great room has a vaulted ceiling and a slider to an enclosed porch that overlooks a private backyard. The kitchen with island has brand new flooring. The spacious primary bedroom has a big closet and connects to a room that could be an office or study with a walk-in closet. A metal roof and vinyl siding are both a plus. The property itself extends right to the banks of Paran Creek with direct access to the water. It's the perfect spot for a picnic table as you listen to the soothing sounds of nature. Set just 0.6 miles from Lake Paran, this location puts swimming, kayaking, fishing, walking trails, and events right at your fingertips. The village itself is part of the appeal. Stroll to local shops, eateries, and community gathering places. Whether you're looking for an incredible investment or a wonderful place to call home, this property is truly a catch.

2 North St, Bennington

$450,000

3 Beds ⋅ 2 Baths ⋅ 5111024 MLS

Location! Welcome to this charming and very well maintained home on desirable Elm Street. Featuring three bedrooms and two bathrooms, this sweet property offers plenty of space, character, and versatility. One of the bedrooms has been thoughtfully transformed into a spacious walk-in closet/dressing room, but it can easily be converted back into a bedroom to restore the home's full three bedroom layout. For added convenience, there are two sets of washers and dryers; one located in the basement and another on the second floor in the converted bedroom/closet. The chefs kitchen has a perfect layout for cooking at home and easily flows to the dining room for family meals, or entertaining friends. Beautiful wood floors add warmth and character throughout the home, while the fireplace in the living room creates a cozy spot to gather on cool evenings. The covered front porch is perfect for enjoying your morning coffee or unwinding at the end of the day. Outside, the property boasts an impressive 1.50-acre double lot, providing plenty of room for gardens, entertaining, outdoor activities, and family fun. Easy drive to Albany, Amtrak train station and Albany Airport in 45 minutes. A two minute drive to the hospital, close to town for walking to restaurants, library and close to the country club for golfing. Monument Elementary School is close by and easily accessed. The best skiing on the east coast and plenty of recreation is not far. Come see all that this lovely home has to offer. I'd love to show you around!

349 Elm St, Bennington

$579,000

3 Beds ⋅ 2 Baths ⋅ 5110554 MLS

Escape to your own private Vermont retreat with this beautiful log home, tucked away in a peaceful, secluded setting surrounded by several acres of thoughtfully landscaped grounds, yet minutes from shopping and dining. From the stamped concrete patio and charming fish pond with waterfall to your very own putting green, this property was designed for enjoying life both indoors and out. Step inside to soaring vaulted ceilings and the warmth and character only a true log home can offer. The open-concept kitchen and dining area creates a wonderful gathering space, complete with a cozy breakfast nook and easy flow into the main living area:perfect for entertaining or simply relaxing at home. The first floor offers two bedrooms, a full bath and convenient laundry area, while the loft-style upper level creates a private primary retreat with bedroom and bath overlooking the surrounding mountain scenery. Outside, enjoy the spacious back deck, recently stained and ready for summer evenings, morning coffee or gatherings with friends. The home’s entire exterior was also professionally sanded and stained this summer, giving the log construction a beautifully refreshed finish. An attached two-car garage adds everyday convenience, while the full basement offers even more usable space with a partially finished office and an expansive workshop perfect for hobbies, projects or storage. Private, beautifully maintained and full of character, this is more than a home: it’s a property meant to be enjoyed. With mountain views, gorgeous grounds and inviting spaces inside and out, there is so much to love and appreciate here.

856 Matteson Rd, Bennington

$175,000

2 Beds ⋅ 1 Baths ⋅ 5109415 MLS

Tired of renting? Discover the charm, convenience, and value of this adorable two-bedroom bungalow - an ideal opportunity for first-time buyers, downsizers, investors, or anyone looking for a cozy second home in town. Tucked away from the hustle and bustle, this historic home is just a short walk from downtown shopping, restaurants, transportation, and everyday conveniences. Inside, you'll find a move-in-ready space with a welcoming dining area just off the kitchen, a spacious primary bedroom, and warm natural light. Step outside and enjoy the covered wraparound porch - always a Vermont favorite. Off-street parking adds an extra layer of convenience. If you're looking to simplify, this charming little jewel is ready to welcome you home!

220 Gage St, Bennington

$385,000

3 Beds ⋅ 2 Baths ⋅ 5109164 MLS

Set on 1.84 acres in Bennington, this 3-bedroom ranch pairs a warm, character-filled interior with established gardens, a wooded backdrop, and one of the home's best surprises: an oversized screened porch made for summer living. The bright kitchen has been updated with granite counters, an apron-front sink, white cabinetry and a gas range, and opens to a cozy living/dining area with wide-plank pine floors, an exposed beam, wood stove, and a broad bank of windows overlooking the front yard. Just off the kitchen, the screened porch adds a substantial amount of usable space, complete with its own sink and a dedicated propane line for the grill. All three bedrooms and the full bath are on the main level. Downstairs, 592 square feet of finished space and a 3/4 bath create a flexible second living area well suited to guests, a media room, hobbies, or a home office. The unfinished portion of the basement offers plenty of room for storage, utilities, and workshop space. Outside, years of gardening show in the mature plantings and colorful beds surrounding the home, with open lawn around the house and woods behind. Enjoy a country setting with recreation close by at Crotched Mountain Ski & Ride and Powder Mill Pond, while downtown Peterborough is about 18 minutes away. Fiber optic internet is available. A warm and inviting home with flexible living space, established gardens, and a peaceful country setting.

224 S Bennington Rd, Bennington

$325,000

3 Beds ⋅ 2 Baths ⋅ 5106631 MLS

Welcome to this inviting Cape-style home offering 3 bedrooms, 2 baths and a comfortable layout designed for both everyday living and entertaining. The main level features an open-concept kitchen and dining area that flows directly onto a huge back deck—an ideal spot for summer dinners, gatherings or simply relaxing while overlooking the secluded, wooded backyard. With both a living room and separate family room, there is plenty of space to spread out, while first-floor laundry adds everyday convenience. The partially finished basement offers additional flexible space for a home office, recreation room, gym or hobbies. Outside, enjoy a peaceful Vermont setting with mountain views, nearby trails and a creek just a short walk away that’s a favorite local spot for cooling off on warm summer days. Tucked away in a private setting yet conveniently close to downtown Bennington, this home offers the best of both worlds: room to relax, space to entertain and easy access to everything the area has to offer.

171 Garbrooke Dr, Bennington

$315,000

3 Beds ⋅ 1 Baths ⋅ 5105313 MLS

There is something special about a home with character, and this charming 3BR property has it in abundance! Set in an established neighborhood within sight of the Mt. Anthony Country Club, this inviting home offers the warmth and craftsmanship of an earlier era combined with the comforts buyers are looking for. From the moment you arrive, the covered front porch welcomes you home. With generous space for rocking chairs or outdoor seating, it's the perfect place to enjoy your morning coffee, unwind after a long day, or simply take in the peaceful surroundings. Step inside and you'll immediately notice the beautiful hardwood floors and natural wood trim that carry throughout the main living spaces. The spacious living room flows seamlessly into the dining room, creating a comfortable layout for both everyday living and entertaining. The kitchen is bright, cheerful, and functional, with white cabinetry, granite countertops, stainless steel appliances, glass-front cabinetry, and excellent natural light. A distinctive painted wood floor adds personality and charm while providing a fun contrast to the traditional finishes throughout the rest of the home. Upstairs, you'll find three bedrooms, each with hardwood flooring and generous windows. In addition to the covered front porch, the property features an enclosed back porch which leads to a beautiful stamped concrete patio, creating a wonderful space for outdoor dining, entertaining, or simply enjoying a summer afternoon. The property also offers a 1 car garage, providing convenient parking and additional storage. The setting is particularly appealing, with the golf course just across the way, while the established neighborhood offers a sense of community and timeless New England charm. If you're looking for a home with genuine character, a wonderful setting, and spaces that feel both gracious and livable, you'll want to see this one soon!

51 Pageant St, Bennington

$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

$179,000

3 Beds ⋅ 2 Baths ⋅ 5104457 MLS

200 feet of Walloomsac River front .There is a second kitchen for a possible in-law or AB&B. RV parking for those visitors who travel listing to the sounds of the stream for the nomadic visitors. New replacement windows were just done. Bring your imagination and see the possibilities. Showings start 8/18/2026

130 Morgan St, Bennington

$375,000

3 Beds ⋅ 2 Baths ⋅ 5104363 MLS

Tucked into Bennington's established Spring Hill neighborhood, this inviting 3 bedroom, 2 bath home offers nearly 2,000 square feet of comfortable living space with a setting that makes it easy to enjoy the outdoors. From the backyard, follow the grass walking trail to the community owned pond, a wonderful extension of your outdoor space and a beautiful spot to enjoy the changing Vermont Seasons. Inside, the living room opens naturally to the kitchen and dining area, creating a connected space for everyday living and entertaining. A separate family room provides plenty of room to spread out and features a woodstove hookup, ready to add warmth and ambiance on chilly evenings. The four season sunroom is a standout, offering a cozy year round spot for morning coffee, reading, relaxing or simply enjoying the backyard views. The home is ready for some cosmetic updating, offering the perfect opportunity to bring your own style and vision while building on an already comfortable and functional layout. Three bedrooms, a deck overlooking the backyard, attached garage and paved driveway, there's plenty here to work with. Add your personal touches and make this Spring Hill home your own.

291 Spring Hill Rd, Bennington

$250,000

4 Beds ⋅ 2 Baths ⋅ 5101031 MLS

Set on a 0.25-acre corner lot, this classic 4-bedroom home offers the space, character, and friendly atmosphere that make Elm Street so appealing. Sidewalks invite evening strolls and dog walks, neighbors gather on their porches, and it's a favorite destination for trick-or-treaters each Halloween. Next to the Elm Street Market, one block from Southwestern Vermont Medical Center, and close to downtown restaurants, theater, and parks, the location is exceptionally convenient while still feeling like a true residential neighborhood. Inside, generous rooms, abundant natural light, hardwood floors, wide moldings, and original architectural details give the home warmth and personality. The spacious living room offers flexibility for gathering, relaxing, or creating multiple seating areas, while the adjoining dining room provides an inviting setting for everyday meals and entertaining. The bright kitchen features abundant wood cabinetry, generous counter space, a farmhouse-style sink, gas range, and direct access to the rear deck. Upstairs are four bedrooms and a full bath, offering ample flexibility for household needs, guests, a home office, or creative space. The primary bedroom includes two closets, and each bedroom has a ceiling fan and overhead light. The full basement houses the laundry and utilities, provides useful storage, and includes an additional toilet. There's a hot air furnace, Rinnai water heater, 100-amp panel, and town water/sewer. Outside, the rear deck overlooks the lawn, established garden beds, and a partially fenced area. A detached one-car garage adds convenient parking, storage, or workshop potential. The home is comfortable and offers a strong foundation. Exterior painting and porch restoration will be up to the next owner, creating an opportunity to refresh the property, make it their own, and build equity over time. With its gracious proportions, original charm, outdoor space, and exceptional location, 301 Elm St is ready for its next chapter.

301 Elm 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 .