$399,000 $144 per sq.ft. Rupert VT Home »

Price Change! Reduced by $31,000 down 8% on August 20th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2768  |  Acres: 6.79
Tuesday Jul 7, 2026
Description: INTERIOR PHOTOS NOW ADDED. Tucked away on a quiet, town-maintained dead-end dirt road, this inviting Rupert, Vermont property offers the kind of peaceful country setting that's becoming increasingly hard to find. Set on 6.79± acres, it's a place where morning walks, afternoon bike rides, and evenings under the stars can become part of everyday life. At the heart of the property is a circa 1850 Greek Revival home, rich with architectural character and topped by a classic slate roof. A substantial steel barn offers exceptional space for hobbies, equipment, vehicles, a workshop, or the projects you've always wanted room to pursue. Significant improvements have already been completed, including a new septic system, ductless mini-split heating and cooling, all new windows and exterior doors, a whole-house water filtration and softener system, an updated bathroom and a generator hookup. These investments provide a solid foundation while leaving room for the next owner to add their own vision. Offered as-is and priced accordingly, the home presents an opportunity to complete additional improvements while creating a property that reflects your own style and needs. There is great upside potential to further enhance the value. Conveniently located just 20 minutes from Dorset, 30 minutes from Manchester, and about an hour from Rutland, Bennington, and Saratoga Springs, you'll enjoy the tranquility of country living with easy access to shopping, dining, recreation, and cultural attractions. If you're looking for a Vermont property with authentic character, open space, and the opportunity to make it your own, schedule your private showing today and experience all this special property has to offer. See MLS Property & Listing Details & 36 images.

$205,000 $85 per sq.ft. Rutland City VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2398  |  Acres: 0.11
Wednesday Feb 18, 2026
Description: Back on the market! Grab it before it's gone again! Classic charm meets flexible and newly updated living space. Originally built in 1915 and updated in 2024, this spacious single family home offers 5 bedrooms, 3 bathrooms, and lots of flex space. Set on an .11 acre city lot, the property offers convenience access to shopping, transportation, and downtown amenities. Inside the home features a versatile layout with multiple flexible rooms, including one currently serving as a den/formal dining room. The main level includes a kitchen with updated appliances, a living room and a formal dining room/ den, along with two first floor bedrooms for added accessibility. Upstairs, you'll find additional bedrooms and a spacious primary suite with its own bath, creating separation and privacy ideal for multi-generational living or guests. The home retains classic character while offering practical updates. Exterior features include a welcoming enclosed front porch, enclosed storage space around back, and a paved driveway. Whether you're seeking a large primary residence, flexible layout for work from home living, or for an investment opportunity in Rutland City, 91 Franklin St. delivers size, character, and convenience in one well located property. OPEN HOUSE Saturday 3/21 11am-1pm for a first look! See MLS Property & Listing Details & 44 images.

$225,000 $135 per sq.ft. Rutland City VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1668  |  Acres: 0.17
Wednesday Aug 12, 2026
Description: Welcome home! This well-maintained 4-bedroom, 2-bathroom home offers plenty of space and versatility. The first floor features a convenient bedroom and laundry, making single-level living a great option. The property also includes a fenced-in area for dogs, providing a secure space for your four legged friends to enjoy the outdoors. Previously used as a two family home, the property offers exciting potential for buyers looking for additional flexibility. If permitted by the City of Rutland, it could potentially be converted back to a two family configuration, making it an excellent opportunity for an owner-occupant, multi generational living, or investment purposes. While the home could benefit from some updating and personal touches, it has been very well maintained over the years and offers a solid foundation to make it your own. A spacious home with character, flexibility, and plenty of potential--come take a look! See MLS Property & Listing Details & 33 images.

$249,000 $113 per sq.ft. Rutland City VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2205  |  Acres: 0.34
Tuesday Jun 30, 2026
Description: Calling all investors and big-family dreamers--here's a five-bedroom, two-bathroom home that knows how to multiply its value. Better yet, it arrives as part of a smart investment package alongside the property next door, doubling your opportunity in one tidy transaction. Five generous bedrooms mean there's room for everyone and everything, whether you're housing a growing household or filling rooms with reliable tenants. With two full bathrooms keeping morning routines civilized, this layout balances livability with genuine income-generating muscle. The rental potential here speaks for itself, and the attractive price point makes the math even sweeter for buyers who like their numbers to add up. Beyond the front door, Rutland's lively scene unfolds. The historic downtown district sits just a short stroll away, where local shops, eateries, and that timeless New England character invite you to linger. Outdoor lovers will adore Pine Hill Park nearby, offering miles of wooded trails for hiking and biking. Peace of mind comes courtesy of Rutland Regional Medical Center, a quick drive down the road, while ski fanatics can chase fresh powder at legendary Killington Resort roughly fifteen minutes away. This is the kind of property that wears two hats with ease--comfortable home base or savvy revenue stream, the choice is yours. Pairing solid bones with a location that keeps tenants and families equally happy, the upside is hard to ignore. Opportunities bundled this neatly don't wait around. Schedule your private showing today. 292 West Street is also available for sale and both properties could be purchased together at a discounted price. See MLS Property & Listing Details & 10 images.

$250,000 $143 per sq.ft. Rutland City VT Home »

Price Change! Reduced by $14,000 down 6% on August 21st 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1745  |  Acres: 0.4
Monday Aug 3, 2026
Description: GREAT VALUE..JUST REDUCED! Spacious Rutland City home featuring four bedrooms to include main floor with 1/2 bath. Eat-in Kitchen as well as formal dining room. Large foyer & luminous living room. Upstairs you will find three more bedrooms & a full bathroom. Plus an office/den. Pleasant covered front porch & covered back porch. Relaxing back patio area ... ideal for enjoying the view of your luscious, private & expansive level back yard. Two car detached garage for an abundance of storage space for all your toys & tools. Brand new oil tank. Furnace just cleaned & serviced. Walking distance to all downtown amenities. Move in and start enjoying your new home. See MLS Property & Listing Details & 55 images.

$251,000 $127 per sq.ft. Rutland City VT Home »

Price Change! Reduced by $1,000 down 0% on August 29th 2026
6 Beds | 2 Baths |   Total Sq. Ft. 1974  |  Acres: 0.16
Monday Jul 20, 2026
Description: Six bedrooms. Two bathrooms. One seriously flexible floor plan. This roomy Rutland home currently lives happily as a single-family residence, but its multi-family past means the bones are already there to convert it back into a two-unit income machine whenever the mood strikes. That kind of dual personality is rare, and it puts you firmly in the driver's seat. Spread out and enjoy every generous room as one big household, or reimagine the layout to collect rent while you're at it. Either way, the attractive price point makes the numbers refreshingly friendly, whether you're a growing family craving elbow room or an investor hunting for reliable cash flow. The location does plenty of heavy lifting too. Rutland's historic downtown sits just a short stroll away, where local shops, cafes, and timeless New England character keep the neighborhood buzzing. Depot Park offers a green spot to unwind, while the nearby train station and regional bus service make getting around wonderfully simple--a real bonus for tenants who value connection. Outdoor lovers won't feel shortchanged either. Pine Hill Park delivers miles of wooded trails practically around the corner, and when snow starts falling, Pico Mountain and legendary Killington Resort are both a quick drive east for world-class skiing. Comfortable home base, savvy rental play, or a little of both--this generous property leaves the choice entirely up to you. Come see the potential in person and start imagining the possibilities today. Also listed as Multi-Family MLS 5100840 See MLS Property & Listing Details & 26 images.

$259,000 $108 per sq.ft. Rutland City VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2397  |  Acres: 0.37
Tuesday Jun 30, 2026
Description: Versatility is the name of the game with this turnkey four-bedroom, two-and-three-quarter-bath property that wears many hats beautifully. Whether you're dreaming of a spacious single-family residence, a multi-family income generator, or a thriving short-term rental venture, the flexibility here is genuinely rare--and the heavy lifting has already been done for you. Move right in without lifting a paintbrush. Everything is ready to go, which means you can start living, hosting, or earning from day one. The proven vacation-rental potential makes this an especially smart play for buyers who appreciate a property that pays its own way while you enjoy the perks of Vermont ownership. Step outside and the appeal only deepens. A generous lot offers room to garden, gather, or simply breathe, while convenient parking keeps everyday comings and goings refreshingly hassle-free. At a price point designed to turn heads, this is the kind of value that makes savvy shoppers do a double take. Location seals the deal. Pine Hill Park sits practically around the corner, rewarding hikers and bikers with miles of wooded trails. Golfers can tee off at the nearby Rutland Country Club, and peace of mind comes easy with Rutland Regional Medical Center close by. When winter arrives, the legendary slopes of Killington Resort are roughly twenty minutes away, and the local train station keeps regional travel simple. Opportunity, comfort, and income potential rarely arrive in one tidy package. Time to seize the moment and schedule your showing today. *294 West Street is also available for sale and both properties could be purchased together at a discounted price. See MLS Property & Listing Details & 21 images.

$265,000 $69 per sq.ft. Rutland City VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 3821  |  Acres: 0.2
Wednesday Aug 26, 2026
Description: Now is your opportunity to bring your vision to this versatile Rutland property. Once configured as a multi-family residence and now utilized as a single-family home, this property offers a unique opportunity for those looking to create a home that fits their needs, or explore a variety of potential uses. Conveniently located close to all of Rutland's city amenities, the property sits directly across from Northwest Primary School and is just a quick bike ride from the renowned Pine Hill Trail system. The Rutland Country Club is right around the corner, while Pico Mountain is less than 20 minutes away, making it easy to enjoy both everyday conveniences and Vermont's outdoor recreation. Whether you're looking for a primary residence, investment opportunity, or a property with the potential to be reimagined, this is a chance to bring your ideas and make the space your own. With its flexible layout and prime location, the possibilities are ready for your vision. See MLS Property & Listing Details & 27 images.

$285,000 $135 per sq.ft. Rutland City VT Home »

Price Change! Reduced by $10,000 down 4% on July 6th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2112  |  Acres: 0.31
Thursday Jun 11, 2026
Description: Welcome to this spacious four-bedroom, two-bathroom home in Rutland City, offering plenty of room to spread out and enjoy both indoor and outdoor living. The heart of the home is the oversized kitchen, providing abundant space for cooking, gathering, and entertaining. Multiple living and entertaining areas, along with a bright and inviting sun porch, create the perfect setting for hosting family and friends year-round. Step outside and discover your own private retreat. The beautifully landscaped, park-like yard is accented by mature perennials and features an in-ground pool, making summer days unforgettable. Whether you're relaxing poolside, gardening, or enjoying a backyard barbecue, this property offers endless opportunities to enjoy the outdoors. Additional highlights include a two-car garage, generous living space throughout, and a layout that offers flexibility for today's lifestyle. Conveniently located close to shopping, restaurants, schools, and everyday amenities, the home also provides easy access to both Pico and Killington ski resorts for year-round recreation. With great bones, abundant space, and timeless appeal, this home is ready for its next owner to add personal touches and make it truly their own. Don't miss this opportunity to own a wonderful property in Rutland City, with space to entertain, relax, and enjoy all that Vermont living has to offer. Welcome Home! See MLS Property & Listing Details & 35 images.

$287,000 $228 per sq.ft. Rutland City VT Home »

Price Change! Reduced by $12,000 down 4% on July 24th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1260  |  Acres: 0.25
Sunday Jun 21, 2026
Description: Why Rent? Stop paying high rent and utilities for an outdated apartment. Say goodbye to unpredictable, skyrocketing annual rent hikes and lock in stable monthly payments. All the hard work has been done. Nothing to do here. Just move in and start building equity. This 4 bedroom 2 Bath City home has been completely remodeled right down to the studs and subfloors and is ready for its next owner. New electrical, lighting, plumbing and heating were done also. Owner added Foam Insulation in the new sheetrocked walls and basement which will be a huge Energy Savings along with the Buderus Furnace and Boilermate Hot Water storage for great efficiency. Roof is in excellent shape and the Vinyl Windows and Siding means limited maintenance needed, saving you time and money! Both bathrooms in the home are equipped with washlet and bidet options. Nice New flooring throughout. Open concept Kitchen and Living area. New kitchen equipped with a Granite topped Eat at Island and luxury Bosch Dishwasher and Dacor Propane Stove. Garbage Disposal also. Dining area and flex space and a Full bath along with 1st floor laundry complete the main level. A Friendship Staircase leads up to 4 bedrooms all with new carpet and a Full bath. Neutral paint colors make this home move in ready. Choice of 2 driveways to use for entry into a mud room and plenty of yard space for adding on a deck or patio. North end of Church St location means you are only three blocks away from Rutland Country Club as well as easy access to all the Rutland area has to offer. Come check out this nicely done remodel and call it home where you can enjoy your own space and freedom to live, decorate and start building your own wealth. Schedule your appointment now for viewing. See MLS Property & Listing Details & 45 images.

$289,000 $149 per sq.ft. Rutland City VT Home »

Price Change! Reduced by $61,000 down 21% on July 22nd 2026
4 Beds | 1 Baths |   Total Sq. Ft. 1945  |  Acres: 0.17
Tuesday May 26, 2026
Description: NEW PRICE! Take a look at this 4-bedroom foursquare home that offers a blend of historic charm and spacious living. The covered front porch leads into a classic foyer and grand staircase followed by a formal dining room with original built-in shelves and the cozy, open living room. The first floor remains versatile with office space, an excellent 3-season porch, a small bathroom and kitchen and then out to a large deck and established perennial gardens. You'll appreciate the size of the second floor bedrooms, a full bathroom, closets and an attic with even more potential. An oversized shed and full basement with tall ceilings will give you all the storage you need and then some! The house has been rewired, a rebuilt chimney with liner and mini-splits help to make this precious home safe, quietly modern and ready for your arrival. See MLS Property & Listing Details & 27 images.

$300,000 $111 per sq.ft. Rutland City VT Home »

Price Change! Reduced by $50,000 down 17% on July 21st 2026
6 Beds | 2 Baths |   Total Sq. Ft. 2702  |  Acres: 4.48
Wednesday Jul 1, 2026
Description: NEW PRICE $300K A rare opportunity to own a historic 157-year-old property situated on 4.48 acres in Rutland City. Rich in character and history, this spacious residence offers the charm and architectural appeal of a bygone era while benefiting from valuable Industrial zoning, creating unique possibilities for investment, redevelopment, or business use (subject to City approvals and permitted uses). The home, constructed in 1869, features a total of fourteen rooms. The first level includes two bedrooms, one bath, a kitchen, living room, and dining room. The second level offers four bedrooms, one bath, a kitchenette, dining room, and two other rooms. Enclosed porches on both levels. A detached classic carriage barn with workshop space and a second floor adds versatility for storage, or future use. The expansive 4.48-acre parcel provides open space, and room for future planning, all while enjoying a convenient city location with easy access to downtown, major roadways, and employment centers. The property retains much of its original character but will require a complete remodel and updating. Interior components are dated, and buyers should be aware of known conditions affecting the property, including knob-and-tube wiring, insulated piping in the basement, and evidence of prior ceiling leaks. Buyers are encouraged to conduct their own inspections and due diligence regarding the property's condition. Located within an Industrial zoning district, the property offers substantial potential beyond its current residential use. Buyers are strongly encouraged to consult with the City of Rutland Planning & Zoning Department regarding permitted and conditional uses.This property is being conveyed in as-is condition, including all remaining contents. Whether you're seeking a distinctive historic home, a live/work opportunity, or a property with outstanding long-term redevelopment potential, this offering presents a rare combination of history, acreage and future possibilities. See MLS Property & Listing Details & 31 images.

$305,000 $105 per sq.ft. Rutland City VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2913  |  Acres: 0.13
Monday Jul 6, 2026
Description: On a beautiful corner lot in Rutland City, this bold blue Victorian home pairs historic character with thoughtful modern updates throughout. From the moment you step inside, the interior makes a statement. Bold color palettes pair with striking modern lighting fixtures. Hardwood floors run throughout, grounding the space in nature. Large windows throughout the home light up every corner of every space. The multiple living areas on the main floor allow conversations to flow, as life fills the space. A stunning built in bookshelf & fireplace insert anchor the living room. From here, the space opens into a dining and sunroom combination, where natural light pours in from every angle. The kitchen sits at the heart of daily life, spacious enough for the whole family to cook, gather, and move freely between rooms. A full bathroom just off the kitchen offers everyday convenience. A formal office or library rounds out the main floor, warmed by its own mini split and offering flexible space for work or quiet time. A mini split in each the kitchen & living room keeps comfort consistent throughout the home. Downstairs, the unfinished concrete basement includes a dedicated woodshop, ready for a craftsman or hobbyist to make it their own. Upstairs, hardwood floors continue through bright, well-proportioned bedrooms. The primary suite includes its own en suite bathroom. Two large, bright bedrooms, one currently used as a nursery complete the sleeping quarters, along with a generous guest suite featuring a large walk-in closet and full bathroom plus enough space to serve as a den, office, or second living area. This suite could easily function as an alternate primary suite. Outside, established gardens welcome you home. A studio apartment with a separate entrance in the back adds flexibility, whether used for rental income or private guest space, all while preserving true single-family living. This is a home built for real life ~ spacious, bright, and full of character. See MLS Property & Listing Details & 45 images.

$310,000 $124 per sq.ft. Rutland City VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2500  |  Acres: 0.13
Friday Nov 21, 2025
Description: This home features , 4 or 5 bedrooms, 3 bathrooms , formal dining room, living on the main level and a great family room upstairs which could be used as a master bedroom, nice woodwork throughout, great floor plan has a nice flow to it, very well kept up and so many updates , including fully weatherized top to bottom this past summer, Windows are new, upstairs has been painted 4 years ago and the carpet is also only 4 years old upstairs.Attic has been insulated and electrical outlets available, pretty much usable space if needed, Back porch has new railings. And there is even a partial treehouse in the back yard. and a newer shed. Fenced for your little ones and pets so they are safe, a nice porch in the front and another big porch in the back for outdoor relaxation, also there is an electric car charger in the driveway Garden has peach trees, elderberries, hazelnuts, raspberries, blackberries, blueberries, raspberries, blackberries, grape, grape kiwi, etc . It's a wonderful house for a family, who wants to walk to the school, to downtown, and who want to harvest the Vermont summers' fruits right from their back yard. See MLS Property & Listing Details & 31 images.

$335,000 $305 per sq.ft. Rutland City VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1994  |  Acres: 0.24
Friday Jun 12, 2026
Description: Tucked away on a dead-end street, this raised ranch offers the perfect blend of comfort, updates, and outdoor enjoyment. Relax on the expansive Trex decking while listening to the peaceful sounds of the nearby babbling brook, creating a truly serene setting right in your own backyard. The main level offers two comfortable bedrooms and a full bathroom, while the lower level includes two additional bedrooms and a 3/4 bath. The larger lower-level bedroom provides excellent flexibility and could serve as a family room, home office, playroom, guest space, workout area, or whatever best suits your needs! Outside, you'll find an inviting pool perfect for summer gatherings, along with a basketball court providing endless opportunities for recreation and fun. Inside, the home features a beautifully updated kitchen, hardwood floors, and plenty of living space to accommodate a variety of lifestyles. See MLS Property & Listing Details & 28 images.