Rutland County Homes under $500,000

Welcome to Rutland County, Vermont—a hidden gem nestled in the heart of New England, where charming small towns meet breathtaking natural beauty. Known for its rich history and vibrant community, Rutland County offers a unique blend of outdoor adventures, cultural experiences, and a welcoming atmosphere that makes it an ideal place to call home.

For those seeking affordable living without sacrificing quality, Rutland County has a fantastic selection of homes under $500,000. Whether you're a first-time homebuyer, looking to downsize, or searching for a vacation retreat, you'll find a variety of options that cater to your needs. From cozy single-family homes in quaint neighborhoods to modern condos with stunning views, there’s something for everyone.

The county boasts an array of recreational activities, making it a paradise for nature lovers. Enjoy hiking, skiing, and fishing in the nearby Green Mountains, or explore the picturesque lakes and rivers that dot the landscape. The vibrant downtown area of Rutland offers eclectic shops, delicious dining options, and a lively arts scene, ensuring that residents have access to both leisure and culture.

With a strong sense of community and a commitment to preserving its natural beauty, Rutland County is more than just a place to live—it's a lifestyle. Discover the charm of this picturesque region and explore the affordable homes available under $500,000, where your dream home awaits amidst the stunning backdrop of Vermont's scenic landscapes. Come and experience the warmth of Rutland County, where your new adventure begins!

Newest Rutland County Homes under $500,000

$199,900

3 Beds ⋅ 2 Baths ⋅ 5113064 MLS

Bring Your Vision to Life in This Historic Victorian! Step back in time with this charming 1860 Victorian home, ideally situated on a 1/3 acre village lot and offering a wonderful opportunity for those with the energy and imagination to restore a piece of local history to its former grandeur. Rich in character and period appeal, this classic property is ready for new owners to bring their vision and creativity to life. The property also features a detached barn, offering excellent potential for storage, workshop space, hobbies, or future possibilities. Conveniently served by town water and sewer, this village property combines historic character with everyday convenience. Located close to all village amenities, you'll enjoy easy access to shops, dining, services, schools, recreation, and community activities. Whether you're an enthusiast of historic homes, an investor looking for a rewarding project, or simply someone who appreciates the charm and craftsmanship of a bygone era, this property offers a rare opportunity to create something truly special. Bring your tools, your ideas, and your imagination as this Victorian is ready for its next chapter!

15 Cedar St, Fair Haven

$199,000

2 Beds ⋅ 2 Baths ⋅ 5113023 MLS

Space, convenience, and opportunity come together at this 2-bedroom, 2-bath, two-story condo in Mountain View Condos. Offering a townhouse-style layout, the home provides comfortable separation between the main living areas and bedrooms while delivering the ease of condominium living. The main level features a surprisingly spacious living and dining area with plenty of natural light and flexibility for furniture placement. The kitchen eat-in offers an abundance of cabinetry and counter space, along with a dishwasher, electric range, double-basin sink, and room to update at your own pace. A bathroom and laundry space on the main level adds to the functionality of the floor plan. Upstairs are two generously sized bedrooms, good closet space, and a full bath. Large windows throughout the home provide natural light, while the two-story configuration gives the condo the feel and functionality of a traditional home. Outside, a covered entry, mature landscaping, and established grounds create an attractive residential setting. The interior is ready for a new owner's personal touches, providing an opportunity to update the finishes to suit your own style rather than paying for someone else's renovations. Conveniently located in Rutland with easy access to shopping, dining, recreation, and the services of the greater Rutland area, this unit offers an appealing combination of space, location, low-maintenance condo living, and potential. Bring your ideas and make this one your own. Welcome home!

155 Dorr Dr Unit 7, Rutland City

$350,000

3 Beds ⋅ 3 Baths ⋅ 5113007 MLS

Two homes in one, or one home that works as hard as you do. This classic colonial offers rare flexibility for the buyer who wants to live and work under one roof, or for co-buyers ready to stop renting and start building equity together. The second floor is a complete living space with its own kitchen, in-unit washer and dryer, and a full walk-up attic for generous storage. It's served by three staircases: a private rear exterior entrance, a rear interior stair, and the front foyer staircase, so you can live together or keep things separate. The main level opens with a spacious foyer and offers a living room, dining room, pantry, a 3/4 bath, a convenient half bath off the foyer, and a bedroom with its own private deck and separate pull-down attic storage. A former kitchen is ready to become a studio, office suite, or restored kitchen. A beautiful covered wraparound deck links the front and side entrances, giving clients or guests a welcoming approach. Outside, enjoy a generous, partially fenced backyard and a multi-car garage with room for vehicles, equipment, or inventory. Home business, house hack, shared ownership, or multi-generational living, this property adapts to your plans. Schedule your showing today.

11 E Washington St, Rutland City

$450,000

5112962 MLS

A rare blend of investment potential, modern living, and Vermont charm — this fully remodeled mixed-use property in the heart of Mendon delivers exceptional visibility on a high-traffic corner lot framed by sweeping mountain views. Designed for flexibility and opportunity, the property features thriving commercial spaces below and a beautifully updated 2-bedroom apartment above — ideal for an owner-occupant, entrepreneur, or investor seeking strong income potential. Live where you work, lease all the units for passive cash flow, or create a custom business destination in one of Vermont’s most traveled corridors. Thoughtfully renovated from top to bottom, every space has been refreshed with modern updates while preserving the versatility needed for a wide range of commercial uses. Perfectly positioned just minutes from Rutland, Killington Resort, and Pico Mountain, this property benefits from year-round tourism, steady traffic exposure, and convenient accessibility. Turnkey properties with this level of visibility, flexibility, and character are increasingly hard to find. Whether you're expanding your portfolio or launching your next venture, this is a standout opportunity in a prime Vermont location. Schedule your private showing today and experience the possibilities firsthand.

1360 Rte 4 E, Mendon

$235,000

3 Beds ⋅ 2 Baths ⋅ 5112773 MLS

Escape to your own piece of Vermont with nearly 3 private acres offering space, flexibility, and the opportunity to bring your personal touches to a quieter way of life. Whether you’re looking for a year-round home, a place to spread out, or simply a property where you can enjoy the outdoors, this home offers plenty of possibilities. The main level provides easy single-floor living with the kitchen, bathroom, and bedrooms conveniently located together. Head downstairs to the finished basement, where additional living space, a second bathroom, and an extra bedroom create even more room for guests, a home office, recreation, or many other possibilities. Outside, the property continues to deliver. A detached garage provides valuable protection for your vehicles during Vermont’s winters, while the additional shed offers plenty of storage for tools, landscaping equipment, outdoor gear, and hobbies. With nearly 3 acres to enjoy, there’s room for gardening, recreation, pets, or simply taking in the peace and privacy that comes with this property. A property with the space, storage, and flexibility to make it truly your own. Come see what Vermont living could look like here.

3707 Whipple Hollow Rd, West Rutland

$160,000

5112693 MLS

Bring your vision to this distinctive Greek Revival-style property in the heart of Wallingford Village. Currently configured as a two-family home, with each unit offering three bedrooms and one bath, this property presents an opportunity for an investor, cash buyer, or purchaser utilizing a renovation loan. The first-floor unit offers more than 1,500 square feet and features an impressive collection of original architectural details, including handsome columns, raised-panel wainscoting, built-ins, and beautiful wood floors with decorative inlay. A classic walk-in pantry provides additional storage, while the rear entry offers space for a potential mudroom, and storage area. Laundry hookups are also available. The covered side porch adds to the home's village appeal. The approximately 0.4-acre lot provides plenty of off-street parking and includes an 18' x 22' single-bay garage building with workshop space and updated electrical. A separate post-and-beam barn includes a single overhead door along with an original carriage-style entry door, creating even more possibilities for storage, workspace, hobbies, or future use. Located within Wallingford Village's Neighborhood Commercial zoning, this property offers flexibility and opportunity, subject to town regulations. The existing two-family configuration provides a solid starting point for someone looking to renovate and prepare the property for rental income, owner occupancy, or another investment strategy. The home does require renovation and is being sold in as-is condition. This an opportunity for someone ready to take on a project and put their own plans into action. With generous living space, period features, useful outbuildings, ample parking, and a convenient village location, there is plenty here to work with. Bring your ideas, your plans, and your vision to Wallingford and see what you can make of this unique property.

60 Depot St, Wallingford

$239,000

3 Beds ⋅ 1 Baths ⋅ 5112689 MLS

Welcome to 100 New Street, a beautifully updated, move-in-ready home sitting on a generously-sized lot in the heart of the village of West Pawlet. Originally built in 1900, this charming residence blends classic character with modern upgrades. First floor laundry in the mudroom is convenient, and the open floor plan is light and airy. There are three bedrooms, including one on the first level. The kitchen includes plenty of storage and room to cook. The lovely living room has a toasty pellet stove to keep you warm on chilly days. Recent updates include a new roof, sliding door off of primary bedroom, complete weatherization, redone driveway, and more. A flat yard with plenty of garden space and two sheds rounds out this great property. Schedule a showing and see all this lovely gem has to offer!

100 New St, Pawlet

$290,000

5112688 MLS

Great investment opportunity or owner-occupied property in the heart of Rutland City! This very well-maintained duplex offers a 3-bedroom unit on the first floor and a spacious 1-bedroom unit upstairs. Both units offer functional layouts with plenty of living space and the convenience of being located close to downtown, shopping, dining, schools, parks, and other Rutland City amenities. The property has been thoughtfully cared for and provides an excellent opportunity for an investor looking to add a solid income-producing property to their portfolio or an owner-occupant looking to offset their mortgage with rental income. The spacious first-floor unit provides three bedrooms, while the upstairs unit offers large manageable one-bedroom layout. A convenient central location, versatile unit sizes, and well-maintained condition make this duplex a property worth exploring.

101 S Main St, Rutland City

$269,000

3 Beds ⋅ 2 Baths ⋅ 5112609 MLS

Country Home with acreage located in the Town of Sudbury. Property is a Commodore Double wide Mobile home that is well cared for and ready to move right in. It has 3 large bedroom with closets and two full baths. Plenty of storage space and windows for natural light and viewing the abundant wildlife. The kitchen has plenty of cupboard space and a handy bar for entertaining. The kitchen opens in to the large living room that is complete with fireplace and nice carpeting. There is a separate dining room and separate utility/Laundry room. This is a great home that also comes with a small barn/shed ideal for storage or livestock. The home sits atop a long driveway and offers beautiful mountain views. The 10 acres is a combo of open and wooded with plenty of room for horses , pets and gardens. Fall foliage is underway and a great time to purchase your new home! .. located between Rutland and Middlebury and just under an hour to Killington.. Several Lakes nearby offer great swimming, fishing and boating. Come take a look!

3242 Young Rd, Sudbury

$375,000

3 Beds ⋅ 2 Baths ⋅ 5112532 MLS

Welcome home to this unique three bedroom, two bath home tucked away in the desirable town of West Rutland, VT. Set on over five acres of beautiful wooded land, this property offers privacy, space, and a peaceful Vermont setting while still being conveniently located to Rutland area amenities. Step inside and discover a distinctive floor plan that gives this home character and personality all its own. The unique layout offers comfortable spaces for everyday living, gathering, and entertaining, with plenty of opportunity to make each space your own. Outside is where this property truly shines. Surrounded by more than five wooded acres, you’ll enjoy a beautiful yard, mature trees, and plenty of room to explore, garden, entertain, or simply relax and enjoy the privacy of your surroundings. If you’re looking for a home that stands apart from the ordinary, this Rutland County property could be exactly you what you've been looking for! It's time to let West Rutland Welcome you Home!

852 Boardman Hl, West Rutland

$385,000

4 Beds ⋅ 2 Baths ⋅ 5112477 MLS

Where the Taconic Mountains meet Vermont’s historic Champlain Valley, the picturesque village of Fair Haven offers small-town charm, beautiful architecture, and a welcoming community. At the heart of the village is a lovely central park hosting year-round events, including summer concerts, the farmers market, and Apple Fest. Quaint shops, local eateries, and a craft brewery add to the appeal of downtown. Set within a desirable subdivision on nearly an acre, this inviting 1988 Contemporary Saltbox style home offers attractive curb appeal, a level and usable yard, and thoughtful updates throughout. The home features 4 bedrooms, 2 baths, an attached garage, and a full basement with excellent storage and future expansion potential. Enter from the garage into a practical mudroom—an especially welcome feature during Vermont winters. The functional kitchen includes a center island with a beautiful locally quarried slate countertop and pantry closet, opening to the adjacent dining area with its striking vaulted ceiling. Freshly painted throughout, the home features durable, eco-friendly bamboo flooring, Andersen windows, and generously sized bedroom closets. Enjoy efficient year-round comfort with five heat pumps, complemented by a newer Buderus boiler. Recent improvements include a brand-new electrical panel, basement support work, and a water filtration system. The basement offers abundant storage, a workbench, and room to potentially expand the finished living space. Outside, enjoy the peaceful setting, attractive landscaping, slate patio, and creative privacy screen—perfect for relaxing or entertaining. A wonderful opportunity to enjoy the best of Vermont village living with space, updates, and room to grow. Come take a look—it just may turn into a lifetime.

10 Muscovey Dr, Fair Haven

$345,000

3 Beds ⋅ 2 Baths ⋅ 5112408 MLS

Thoughtful updates and pride of ownership shine throughout this raised ranch style home! The main level offers a bright, sunny living room and a modern, updated kitchen. Down the hall you’ll find three comfortable bedrooms and a full bathroom, providing a practical layout with plenty of room to make it your own. The lower level adds even more versatility with a one car garage, laundry room with a ¾ bathroom, and a large bonus room that could easily serve as a home gym, office, game room, guest space, or whatever best fits your needs. Step outside onto the back deck and enjoy overlooking the spacious lot an ideal spot to relax or entertain. The seller has taken great pride in this home and have completed numerous updates, making it a wonderful opportunity for anyone looking for a move-in-ready home in Rutland City. With its flexible living space, modern updates, and inviting outdoor area, this one is ready to welcome its next owners!

15 Victor Pl, Rutland City

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