You are viewing all listings Homes between $250000 and $500000 dollars.
$430,000 $155 per sq.ft. Rupert VT Home »
4 Beds | 2 Baths | Total Sq. Ft. 2768 | Acres: 6.79Listed on 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 Listing Details & 36 images.
Under Contract
$250,000 $209 per sq.ft. Rutland City VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1197 | Acres: 0.11Listed on Thursday Jul 16, 2026
Description: Historic Charm. Modern Upgrades. Easy Living. This beautifully maintained 3-bedroom, 1.5-bath home perfectly balances classic detail with smart, modern updates. It starts with the welcoming wraparound front porch, which is a spacious, inviting spot for enjoying morning coffee, evening cocktails with friends, or simply curling up with a good book. Upon entering, you'll find the inside of this home as appealing as the outside, highlighted by original woodwork and hardwood floors. The living and dining rooms flow openly into one another, making the main level perfect for everything from easy, everyday living to hosting holiday gatherings. At the center of the home is the kitchen, featuring stainless steel appliances, plenty of storage, and a handy mudroom that leads out to the side porch and the backyard. A flexible first-floor bedroom (currently used as a den) sits near the half bath, making it the perfect setup for guests, first-floor living, or a home office. Upstairs, an open bonus room offers extra hangout space, alongside a full bath and two comfortable bedrooms, one of which has a classic transom window and a private balcony. Behind this home's vintage charm are impressive energy-efficient infrastructure upgrades, including a new boiler, a heat pump water heater, and a mini-split for efficient heating and cooling. There is also an exterior EV charger and a state-of-the-art smart SPAN® electrical panel that lets you manage the whole home's energy right from your phone. Located in the heart of Rutland, this lovely home is just moments from downtown restaurants, shopping, parks, RRMC, and a plethora of recreational opportunities, including Pine Hill Park for mountain biking and Killington-Pico Ski Resort. See Listing Details & 32 images.
$252,000 $128 per sq.ft. Rutland City VT Home »
6 Beds | 2 Baths | Total Sq. Ft. 1974 | Acres: 0.16Listed on 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 Listing Details & 26 images.
$259,000 $108 per sq.ft. Rutland City VT Home »
4 Beds | 4 Baths | Total Sq. Ft. 2397 | Acres: 0.37Listed on 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 Listing Details & 21 images.
New Listing!
$275,000 $153 per sq.ft. Rutland City VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 2448 | Acres: 0.2Listed on Thursday Jul 30, 2026
Description: Tucked just off North Street Extension, this spacious 3-bedroom home offers the flexibility to grow, gather, and spread out, all with the privacy of a generous backyard setting. Whether you're hosting friends around the fireplace, enjoying a quiet morning coffee overlooking the lawn, or taking advantage of the home's versatile layout, there's room here for every season of life. The main level is cozy and welcoming, featuring an open flow between the eat-in kitchen and living room. A striking fireplace creates a warm focal point in the large living room while updated countertops, appliances and cabinets in the kitchen create everyday convenience. Three spacious bedrooms, a functional full bath, and attached garage complete the upper level. Downstairs expands your living options with a large and comfortable family room centered around a nice hearth, an office or flex-room, oversized utility and laundry room with a working toilet and sink that could become a second full bathroom. Sliding outside is easy with the walkout access to the backyard through the large 3-season room, creating a natural connection between indoor and outdoor living. Thoughtful updates, including: replacement windows, fresh paint, wood and tile flooring, newer roof, recently lined and capped chimney mean you can spend less time on projects and more time enjoying your new home. If you've been searching for a home with generous living space, flexible rooms, and a peaceful setting that's still close to local amenities, this one is ready to welcome you home. See Listing Details & 32 images.
New Listing!
![Rutland City VT Home for sale $279,000 $257 per sq.ft.]()
$279,000 $257 per sq.ft. Rutland City VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1084 | Acres: 0.2Listed on Tuesday Jul 28, 2026
Description: Open House 8/1 11am-1pm! This charming single-family home in Rutland City is bound to sell quickly! Imagine yourself relaxing, sipping coffee, and watching the sun rise from your large, private deck, the perfect place to start your day or unwind in the evening. Inside, you'll find warm wood finishes throughout that add character and charm, while the spacious layout offers flexibility to fit a variety of lifestyles. Step inside to a welcoming dining area that flows seamlessly into the large kitchen, offering space for either bar-style seating or a full dining table, making it ideal for everyday meals or gathering with family and friends. The first floor also includes a private office or bonus room, providing additional space for working from home, hobbies, or other needs. Continue past the kitchen and dining area into the expansive, sun-filled living room, where natural light creates a bright and inviting atmosphere. Just off the living room is a generously sized first-floor bathroom with the convenience of laundry. Upstairs, you'll find two charming bedrooms, each featuring large dormer windows that bring in plenty of natural light, closet space, and built-in beds that add to the home's unique character. A spacious second bathroom completes the upper level, offering added convenience and functionality. With its versatile floor plan, inviting living spaces, and distinctive charm, this home is ready for its next owner to make it their own. See Listing Details & 48 images.
Under Contract
$280,000 $243 per sq.ft. Rutland City VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1152 | Acres: 0.3Listed on Thursday Jun 25, 2026
Description: Welcome home to this adorable three-bedroom, one-bathroom ranch offering the ease and convenience of one-level living. Perfect for first-time buyers, those looking to downsize, or anyone seeking a move-in-ready home, this charming property is ready for its next owners. Step outside and enjoy the spacious, level backyard featuring a deck that's perfect for summer barbecues, entertaining guests, or simply relaxing with family and friends. With plenty of room for gardening, outdoor games, or creating your own backyard oasis, this property offers endless possibilities for enjoying Vermont's beautiful seasons. Adding to the home's appeal are 20 leased solar panels, providing an energy-efficient way to help reduce monthly electrical costs while lowering your carbon footprint. It's a great opportunity to enjoy the benefits of renewable energy and long-term savings. Conveniently located close to shopping, restaurants, schools, parks, and all the amenities Rutland City has to offer, this inviting home combines comfort, convenience, and outdoor enjoyment. Don't miss your opportunity to make this charming ranch your next home! See Listing Details & 37 images.
$285,000 $138 per sq.ft. Village of Rutland in Town of Rutland City VT Home »
Price Change! Reduced by $5,000 down 2% on July 6th 2026
3 Beds | 2 Baths | Total Sq. Ft. 2064 | Acres: 0.16
Listed on Friday May 1, 2026
Description: A beautifully maintained 3-bedroom, 2-bathroom home that offers comfort, charm, and a fantastic location. This well-cared-for property features a warm and inviting interior with spacious living areas perfect for everyday living and entertaining. The home includes a partially finished attic, offering flexible space for a home office, playroom, or additional storage. Step outside to enjoy a beautiful backyard -- ideal for relaxing, gardening, or hosting gatherings. Conveniently located close to downtown and just minutes from Pine Hill Park, you'll enjoy easy access to shopping, dining, outdoor recreation, and all the amenities the area has to offer. This move-in-ready home is a wonderful opportunity you won't want to miss! Open House 6/20/2026 11-2pm! See Listing Details & 27 images.
Under Contract
$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
Listed on 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 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
Listed on 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 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
Listed on 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 Listing Details & 27 images.
$289,000 $318 per sq.ft. Rutland City VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 910 | Acres: 0.24Listed on Wednesday Jul 8, 2026
Description: Three bedroom ranch on a spacious city lot in the outskirts of Rutland City with impeccable mountain views. Close to restaurants and parks, but central to skiing and lake regions. The house has been well maintained and is ready for its new owners to make it their own. See Listing Details & 24 images.
Under Contract
$289,000 $204 per sq.ft. Rutland City VT Home »
3 Beds | 1 Baths | Total Sq. Ft. 1414 | Acres: 1Listed on Tuesday Jul 14, 2026
Description: Set on an oversize private estimated 1-acre lot in Rutland City, this charming Cape-style home offers a combination of character, comfort, and outdoor space that's increasingly hard to find. Rich natural woodwork throughout the home creates a warm, inviting atmosphere from the moment you step inside. The main level features two generously sized bedrooms, a full bathroom, and the convenience of one-level living if desired. The living room is centered around a beautiful wood-burning fireplace, creating the perfect gathering space for family and friends or a cozy evening at home. Upstairs, you'll find a third bedroom and a versatile loft that's ideal for a home office, reading area, hobby room, play space, or guest accommodations, offering flexibility to meet your changing needs. Outside, the private estimated 1 acre lot provides room to garden, entertain, play, or simply relax and enjoy the peaceful surroundings. A detached two-car garage offers excellent storage and parking, while the spacious driveway provides additional off-street parking for guests and multiple vehicles. Conveniently located near downtown Rutland, schools, shopping, restaurants, Rutland Regional Medical Center, White's Pool, and Pine Hill Park, you'll also enjoy easy access to hiking, biking, golf, lakes, and world-class skiing at Killington and Pico. If you've been searching for a home with classic Cape-style charm, a private setting, and room to enjoy both indoors and out, this property is ready to welcome you. Property video available upon request. Public Open House this Saturday, July 18, from 10:30 a.m. to 12:00 p.m. See Listing Details & 30 images.
Under Contract
$290,000 $196 per sq.ft. Rutland City VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 2436 | Acres: 0.28Listed on Wednesday Jul 15, 2026
Description: Welcome to this well-maintained 1960 ranch offering the perfect blend of comfort, space, and convenience. With 1,478 square feet of above-grade living space plus an additional 958 square feet of finished lower-level living area, this home provides exceptional flexibility for today's lifestyle. The main level features three comfortable bedrooms, a full bath, a bright and inviting living room, and a functional kitchen with adjoining dining area, creating a welcoming space for everyday living and entertaining. The (mostly) finished lower level expands your options with generous recreation and gathering space, a half bath, and room for a home office, fitness area, hobbies, or overnight guests. An attached garage offers added convenience, while the property's established setting provides the perfect backdrop for outdoor enjoyment. Whether you're hosting family and friends or simply looking for extra room to spread out, this home offers the versatility buyers are searching for. Ideally located in a desirable Rutland City neighborhood, you'll enjoy easy access to schools, shopping, restaurants, parks, healthcare, and everyday amenities. Offering outstanding value, comfortable living spaces, and room to grow, 224 Pearl Street is ready to welcome its next owner. Schedule your private showing today! See Listing Details & 39 images.
New Listing!
$295,000 $239 per sq.ft. Rutland City VT Home »
3 Beds | 2 Baths | Total Sq. Ft. 1830 | Acres: 0.21Listed on Friday Jul 31, 2026
Description: Welcome to this inviting three-bedroom, two-bath raised ranch, ideally located in a quiet residential neighborhood of Rutland City. The home offers a comfortable and practical layout, with a finished lower level that provides additional living space for a family room, home office, recreation area, or guest accommodations. Just off the kitchen, a spacious rear deck creates the perfect setting for outdoor dining, entertaining, or simply relaxing while enjoying the privacy of the backyard. A picturesque stream borders the rear of the property, adding a peaceful natural backdrop and a sense of tranquility that is rarely found within the city. Conveniently located near Rutland High School, the Rutland Regional Medical Center, shopping, dining, and other local amenities. This home offers a wonderful combination of neighborhood living, flexible interior space, and a private outdoor setting so this one should be on your short list. Welcome Home! See Listing Details & 20 images.
