$1,749,000 $544 per sq.ft. Rupert VT Home »


Price Change! Reduced by $346,000 down 20% on June 12th 2026
5 Beds | 5 Baths |   Total Sq. Ft. 3218  |  Acres: 5.41
Listed on Thursday Jul 10, 2025
Description: Luxury move in ready fully renovated 1909 Federal home on 5+ peaceful acres, protected mountain views and stream frontage, but just 5 minutes from the activities on the Dorset Green and the Dorset Field Club. A 3 year renovation by the areas most skilled workmen includes a custom walnut kitchen with high end appliances, island bar seating opening to dining room for entertainment and family life. New hickory floors and walnut railings throughout accentuate this light filled home. The new custom stone fireplace and chimney in the living room opens to a spacious private covered porch. The first floor primary bedroom incudes a bathroom with spa like vibe and includes spectacular views to wake up to. Upstairs has 3 bedrooms, including a second primary suite with bathroom, walk in closet and 2 additional bedrooms with bathroom and a bonus television or recreation room. Outdoor space includes an elegant custom stone deck that is perfect for quiet morning coffee, drinks or evening dinners. A fully renovated living cottage with cathedral ceilings provides privacy with its own driveway and address which could be flex space for guests, office or studio, or as a rental. Add a Airstream trailer for additional quiet space down by the stream. Both homes have new or newer septic systems; with every aspect improved including new siding; roofs; IPE decks, Marvin windows, propane tanks, and Generac generators for many years of worry free living. Landscaping improvements are still underway ! See Listing Details & 54 images.

$74,900 $47 per sq.ft. Rutland City VT Home »


Price Change! Reduced by $25,000 down 33% on June 13th 2026
4 Beds | 1 Baths |   Total Sq. Ft. 1585  |  Acres: 0.12
Listed on Sunday Feb 22, 2026
Description: This property is part of a First Look program. It allows owner occupant buyers to have their offers negotiated on day 8 of being listed."ALL offers must have POF for CASH offers and Lender PQ's for Financed offers. Cash offers require 10% EMD. Rehab Offers must have one rehab bid in hand pre-offer, no exceptions. "New RRE Rules for FINCEN. transfers will be subject to reporting when buyers use entities or trusts to take title to residential real estate, when the transaction is all-cash, privately financed or HELOC. See Listing Details & 11 images.

New Listing! Rutland City VT Home for sale $128,000 $74 per sq.ft.

$128,000 $74 per sq.ft. Rutland City VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1738  |  Acres: 0.25
Listed on Monday Jun 8, 2026
Description: Property is HUD owned. FHA CASE#531-039801. Situated in Rutland City with public water and sewer is this 4 bedroom home priced to sell!!!! With a quarter of an acre level lot, 1.5 baths, full basement and an adquate amount of living space, this won't last long!!! See Listing Details & 23 images.

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

5 Beds | 3 Baths |   Total Sq. Ft. 2398  |  Acres: 0.11
Listed on 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 Listing Details & 44 images.

$220,000 $131 per sq.ft. Rutland City VT Home »

4 Beds | 1 Baths |   Total Sq. Ft. 1680  |  Acres: 0.08
Listed on Wednesday Mar 18, 2026
Description: Welcome to 48 Baxter Street, a charming and spacious home located just steps from downtown Rutland's shops, dining, and activities. This inviting property offers four bedrooms upstairs, providing plenty of space for family, guests, or a home office. The main floor features a bright kitchen with stainless steel appliances, a comfortable dining area, and a welcoming living room--perfect for gatherings and everyday living. A large front entry adds character and functionality, while the side porch offers a cozy spot to relax. Convenience is key with first-floor laundry and a one-car detached garage. Blending comfort with walkability, this home is an ideal choice for those who want to enjoy all that Rutland has to offer. See Listing Details & 22 images.

Under Contract Rutland City VT Home for sale $249,000 $84 per sq.ft.

$249,000 $84 per sq.ft. Rutland City VT Home »


Price Change! Reduced by $33,500 down 13% on June 8th 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2947  |  Acres: 0.13
Listed on Saturday May 9, 2026
Description: PRICE IMPROVEMENT on this wonderful Rutland home -- where classic charm, space and flexibility come together in this spacious two-and-a-half-story Colonial designed for comfortable multi-generational living. Conveniently located near local hospital, shopping, schools and everyday amenities this home offers versatility and room to grow with flexible living spaces throughout. Inside, you'll find beautiful hardwood floors, two kitchens and multiple living areas that provide room for everyone to spread out while still feeling connected. The thoughtful layout offers endless possibilities for today's evolving lifestyle needs, whether you're looking for additional gathering spaces, work-from-home options or room for extended living arrangements. Extensive electrical updates have already been completed, offering added value and peace of mind. Outside, enjoy a nice backyard perfect for relaxing, gardening or entertaining, along with a detached two-car garage offering ample storage for vehicles, tools, outdoor gear and more. Plenty of parking and a convenient in-town location make everyday living easy. This Rutland City Colonial combines character, functionality, and opportunity -- all in a location close to everything you need. Come take a look! See Listing Details & 43 images.

New Listing! Rutland City VT Home for sale $295,000 $140 per sq.ft.

$295,000 $140 per sq.ft. Rutland City VT Home »

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.

$299,500 $189 per sq.ft. Rutland City VT Home »


Price Change! Reduced by $16,400 down 5% on June 2nd 2026
4 Beds | 2 Baths |   Total Sq. Ft. 1582  |  Acres: 0.23
Listed on Wednesday May 20, 2026
Description: Gorgeous Cape cod on Dead end Street with oversized two-car garage. Beautiful hardwoods, New boiler. New baseboard, new painting. New sheetrock. Complete new electric, beautiful private rear yard, new kithen counters, 5 car driveway, propane fireplace or wood, huge front and rear porches, garage has bathroom and an upstairs for great workshop. Short stroll to town, low taxes, oversized double lot . Don't miss this one. See Listing Details & 17 images.

$305,000 $157 per sq.ft. Rutland City VT Home »


Price Change! Reduced by $45,000 down 15% on June 9th 2026
4 Beds | 1 Baths |   Total Sq. Ft. 1945  |  Acres: 0.17
Listed on Tuesday May 26, 2026
Description: This beautiful four-bedroom, two-story Foursquare home offers a blend of historic charm and peace of mind. Featuring four large bedrooms, a formal dining room with original built-in shelves, a versatile first-floor office, a three-season porch and established perennial gardens. The property is designed for comfortable and practical living with a spacious, classical layout. Upgraded electrical, 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.

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


Price Change! Reduced by $40,000 down 13% on June 15th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 2500  |  Acres: 0.13
Listed on 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 Listing Details & 31 images.

Under Contract Rutland City VT Home for sale $315,000 $210 per sq.ft.

$315,000 $210 per sq.ft. Rutland City VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1498  |  Acres: 0.17
Listed on Monday May 11, 2026
Description: Nestled in a classic 1920s Cape, this inviting 4-bedroom, 2-bath home blends timeless character with thoughtful updates and exceptional flexibility. Rich original woodwork, beautifully maintained hardwood flooring, and charming period finishes create warmth and personality throughout the home. Designed with entertaining in mind, the spacious layout offers comfortable gathering spaces, a cozy working wood-burning fireplace, and a bright sunny 3-season room perfect for relaxing with morning coffee or unwinding at the end of the day. Mini-splits and an oil boiler provide year-round comfort and efficient heating and cooling options. The recently updated lower level adds outstanding versatility, featuring its own bathroom and flexible space ideal for guests, a home office, recreation area, or additional bedroom setup. Generous closet space and abundant storage can be found throughout the home, making everyday living easy and organized. Step outside to enjoy the private fenced yard and expansive deck, offering an excellent setting for outdoor dining, gardening, or entertaining. A large 12 x 20 shed provides even more room for tools, equipment, hobbies, or seasonal storage. Full of charm, functionality, and flexible living space, this beautifully maintained Cape offers a rare combination of historic character and modern convenience. See Listing Details & 32 images.

$319,000 $131 per sq.ft. Rutland City VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2428  |  Acres: 0.17
Listed on Tuesday Jun 2, 2026
Description: Spacious & Character-Rich 5BR/2.5BA in Rutland City, Move-In Ready with Thoughtful Updates and In-law Suite. Charming 5-bedroom, 2.5-bath home in Rutland City beautifully blends historic character with modern upgrades, and it shows throughout. Whether you're hosting a backyard barbecue, carving out a home office, or simply enjoying the views of Killington from the back deck, this well-cared-for property delivers on both space and lifestyle. The renovated family room (2019) featuring new hardwood floors, ceiling, and sheetrock adds a second fully functional living space that's perfect for movie nights, a playroom, or a quiet retreat. The main level also offers a formal dining room, living room, laundry room, and a flexible bedroom with bath, ideal for a home office or guest room. Additionally, a private in-law suite with its own kitchen, living area, bedroom, and bathroom is perfect for extended family or potential rental income with peek-a-boo views of Killington to boot. Step outside and you'll find one of Rutland City's more generous lots, complete with raised stone garden beds, a stone patio, and a privacy fence (2025), an ideal setup for entertaining or letting kids and pets roam freely. A large barn/garage rounds out the property with serious storage potential. Recent updates give you added peace of mind: new driveway (2024), brand new water heater (2026), oil tank (2019), and updated light fixtures throughout. Located on a quiet street within walking distance to downtown shopping, dining, and parks, and just a short drive to Killington Resorts for skiing, biking and hiking. A rare find in the city. See Listing Details & 50 images.

New Listing! Rutland City VT Home for sale $325,000 $232 per sq.ft.

$325,000 $232 per sq.ft. Rutland City VT Home »

4 Beds | 3 Baths |   Total Sq. Ft. 2410  |  Acres: 0.69
Listed on Monday Jun 15, 2026
Description: Welcome to this Rutland City home located on a spacious 0.69-acre lot with views and a fenced backyard that's great for pets, children, gardening, or simply enjoying the outdoors. The property also includes a storage shed and a large back deck overlooking the yard, providing a nice space for barbecues, relaxing, and entertaining. The main level features a kitchen, dining room, and living room with a fireplace. The dining room is open to the living room, creating a comfortable gathering space. There are also three bedrooms and a full bathroom on this floor. The walkout basement offers plenty of natural light and additional living space, including a bonus room, a fourth bedroom or office, and a 3/4 bathroom. The basement also contains what was once an indoor pool. Buyers may choose to explore restoring the pool or repurposing the space for storage or other uses. An attached two-car garage with extra storage space adds to the home's functionality. With its convenient Rutland City location, generous lot size, fenced yard, views, and flexible living spaces, this property offers plenty of opportunity for its next owner. See Listing Details & 30 images.

New Listing! Rutland City VT Home for sale $335,000 $305 per sq.ft.

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

4 Beds | 2 Baths |   Total Sq. Ft. 1994  |  Acres: 0.24
Listed on 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 Listing Details & 28 images.

$349,900 $131 per sq.ft. Rutland City VT Home »

5 Beds | 2 Baths |   Total Sq. Ft. 2679  |  Acres: 0.25
Listed on Friday Mar 20, 2026
Description: Discover space, character, and modern convenience in this beautifully renovated and meticulously maintained Victorian farmhouse-style home. Offering 2,679 square feet of living space, this expansive two-story residence features five generously sized bedrooms and two full bathrooms, ideal for a variety of living arrangements. A welcoming entry foyer showcases the home's original staircase and timeless charm. The spacious living and dining rooms are filled with natural light, creating a warm and inviting setting for everyday living and entertaining. At the center of the home is a thoughtfully updated kitchen (2022) featuring white cabinetry, solid-surface countertops, and stainless steel appliances. The main level also includes a bedroom, full bath, office, and an oversized mudroom with convenient rear entry. Upstairs, you'll find four additional bedrooms, a full bath, a centrally located family room, and a second office, along with a separate second-floor entrance accessed by a covered exterior stairway--offering added flexibility. Recent improvements completed in 2022 include updated bathrooms, fresh interior paint, new carpeting, luxury vinyl plank flooring, and a new furnace with upgraded mechanicals. With low-maintenance vinyl siding, replacement windows, a dedicated Generac backup generator, and pride of ownership throughout, this home is truly move-in ready. Set on a pleasant, tree-lined street with ample off-street parking, the property offers easy access to local schools, shopping, dining, and community amenities, as well as year-round recreational opportunities just a short drive away, including the world-class Killington-Pico Resort. Combining generous space, thoughtful updates, and convenient Rutland City location, this home is a standout opportunity. Enjoy the virtual property tour with floor plan and photographs. See Listing Details & 37 images. Includes a Virtual Tour

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