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Homes for Sale in Rutland County VT with 5-Bedrooms

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  • /45

    $550,000

    • 5 Beds
    • 3 Baths
    • 3,876 Sq Ft

    5 Pearl St, Brandon, VT 05733

    Timeless Colonial with Modern Updates & Rustic Charm * Welcome to this beautifully maintained Colonial-style home offering 4 spacious bedrooms and 3 baths, perfectly blending classic character with thoughtful updates. Step inside to discover brand-new flooring throughout and an abundance of natural light streaming in through 17 newly installed windows. The heart of the home is the rustic family

    Agent Photo

    Amey Ryan

    IPJ Real Estate

    (802) 821-8209

    5 Pearl St, Brandon, VT 05733
  • /32

    $389,000

    • 10 Beds
    • 4 Baths
    • 4,230 Sq Ft

    25 Killington Ave, Rutland, VT 05701

    Two buildings on one lot, with this exceptional investment opportunity featuring two duplex buildings being sold together in a highly desirable location. Offering a total of four income-producing units and a strong rental history, this property presents a turnkey addition to any investor’s portfolio.The first building consists of two comfortable two-bedroom units, each equipped with the

    Agent Photo

    Hughes Group Team

    Casella Real Estate

    (802) 397-5903

    25 Killington Ave, Rutland, VT 05701
  • /60

    $2,225,000

    • 5 Beds
    • 5 Baths
    • 5,691 Sq Ft

    1926 W Lake Rd, Wells, VT 05774

    Everything you could want in a lake house is right here. Perfectly positioned on its own point on Lake St. Catherine, this exceptional residence offers commanding views of both the open lake and the quiet cove. Crafted with stone fireplaces, exposed beams, and bespoke details—including hidden bookcase doors—this home blends timeless character with refined comfort. The main level showcases a

    Christiane Carroccio TPW Real Estate

    1926 W Lake Rd, Wells, VT 05774
  • /40

    $1,250,000

    • 6 Beds
    • 3 Baths
    • 3,584 Sq Ft

    96 Tabor Rd, Cuttingsville, VT 05738

    Set amid sweeping mountain views, open meadows, and forested trails at the peaceful end of Tabor Road, this 93.4 acre Shrewsbury retreat captures the essence of Vermont living: private, expansive, and deeply restorative. The landscape is the defining feature - open fields, wooded paths, and three ponds, including a hidden gem tucked awaydown a wooded trail that suddenly opens into a wide

    Kim Prins Four Seasons Sotheby's Int'l Realty

    96 Tabor Rd, Cuttingsville, VT 05738
  • /60

    $1,800,000

    • 6 Beds
    • 5 Baths
    • 4,719 Sq Ft

    1204 Bailey Rd, Cuttingsville, VT 05738

    Welcome to Salt Ash Farm, a treasured retreat in the hills of Vermont on 97 +/- acres. This incredible 6 bedroom, 5 bath home has been thoughtfully expanded and updated over the years and offers a unique blend of classic, rustic and contemporary features. Peace and tranquility resonate throughout. The spacious well-appointed kitchen has floor to ceiling windows with a majestic view. Just off the

    Geralyn Donohue Engel & Völkers Okemo

    1204 Bailey Rd, Cuttingsville, VT 05738
  • /16

    $235,000

    • 5 Beds
    • 2 Baths
    • 1,864 Sq Ft

    138 Maple St, Rutland, VT 05701

    Step into a piece of history with this well-maintained turn-of-the-century duplex, perfectly situated for comfortable living or smart investment. Built in 1900, this two-family home blends classic architectural details with practical, move-in-ready spaces that are ideal for owner-occupants, house-hackers, or investors seeking steady rental income. The first-floor apartment offers a spacious

    Joshua Lemieux Remax Summit

    138 Maple St, Rutland, VT 05701
  • /51

    $595,000

    • 6 Beds
    • 3 Baths
    • 3,146 Sq Ft

    348 Bentley Ave, Poultney, VT 05764

    This Queen Anne-Colonial Revival home blends old-world charm with modern comfort. Known historically as the C. W. Humphrey House and later “The Meeting House,” it was built in the early 1900s by Charles W. Humphrey for his new bride, featuring ornate wood trim, intricate inlaid parquet floors, and colorful stained-glass windows. In 2013 the home was lovingly restored through the efforts of Green

    Suanne Ohl Northland Real Estate

    348 Bentley Ave, Poultney, VT 05764
  • /37

    $349,900

    • 5 Beds
    • 2 Baths
    • 2,679 Sq Ft

    7 Royce St, Rutland, VT 05701

    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

    Wendy Pallotta Four Seasons Sotheby's Int'l Realty

    7 Royce St, Rutland, VT 05701
  • /51

    $529,000

    • 5 Beds
    • 2.5 Baths
    • 3,234 Sq Ft

    209 State St, Rutland, VT 05701

    Discover this meticulously renovated 3,200+ sq ft duplex, offering a rare blend of historic charm and modern efficiency. This property has a completed condo conversion, providing the unique opportunity to sell the units individually in the future. The interior features freshly painted spaces and mostly original wood flooring. The first-floor unit boasts an upgraded kitchen and a new primary

    Evan Russell Real Broker LLC

    209 State St, Rutland, VT 05701
  • /56

    $990,000

    • 5 Beds
    • 5 Baths
    • 4,300 Sq Ft

    49 Sherri Ln, North Clarendon, VT 05759

    Welcome to your own private sanctuary nestled in a small, peaceful community with spectacular mountain views in every season. This fully renovated home blends comfort, craftsmanship, and thoughtful design throughout. Step inside to discover a bright and airy living space featuring beautiful hardwood and softwood flooring, radiant heat for year-round comfort, and central air conditioning for those

    Joshua Lemieux Remax Summit

    49 Sherri Ln, North Clarendon, VT 05759
  • /28

    $589,000

    • 11 Beds
    • 6 Baths
    • 4,959 Sq Ft

    1 Nickwackett St, Rutland, VT 05701

    Located in the heart of Historic Rutland City, this fully renovated and income-producing triplex offers a rare turnkey investment opportunity. Featuring 11 bedrooms and 6 full bathrooms, the property is configured for high-efficiency, dormitory-style living and comfortably accommodates up to 20 occupants.The building has been thoughtfully updated and styled for function, durability, and

    Erin Shimp Engel & Völkers Okemo

    1 Nickwackett St, Rutland, VT 05701
  • /27

    $99,000

    • 6 Beds
    • 3 Baths
    • 3,414 Sq Ft

    304 Main St, Poultney, VT 05764

    Attention investors and DIYers! This multi-family colonial on Main Street in historic downtown Poultney might be just what you need. Unit "A" features new downstairs flooring, fresh paint, and a brand-new bathroom. The bedroom floors have been refinished, and the galley kitchen is ready for your personal touch. Unit "B" is a first-floor apartment with a partially remodeled full bath, plus plenty

    Suanne Ohl Northland Real Estate

    304 Main St, Poultney, VT 05764
  • /26

    $749,000

    • 7 Beds
    • 7 Baths
    • 4,231 Sq Ft

    1295 & 1297 Route 149, Pawlet, VT 05761

    West Pawlet: Significant rental income, Annual Net Income is $66,200. Higher rental income potential in 3 years. Heat included in all apartments. 1295 Route 149: 3 Unit building. 2- 1-bedroom apartments and 1- 2-bedroom apartment. Each apartment has own forced hot air furnace and electric hot water heaters. 1297 Route 149 is in a 5-year low income program, with approx. 3 years remaining. 4- 1

    Melissa Loughan Westside Real Estate

    1295 & 1297 Route 149, Pawlet, VT 05761
  • /22

    $265,000

    • 8 Beds
    • 5 Baths
    • 3,220 Sq Ft

    9 River St, Fair Haven, VT 05743

    This well-maintained five-unit multifamily asset offers a strong investment profile, anchored by a solid 10% cap rate and consistent rental performance. The property features a diversified unit mix consisting of three two-bedroom apartments, one one-bedroom unit, and one efficiency, supporting broad tenant appeal and reliable occupancy. Operating efficiency is enhanced by landlord-provided heat,

    Joshua Lemieux Remax Summit

    9 River St, Fair Haven, VT 05743
  • /11

    $574,000

    • 5 Beds
    • 1.5 Baths
    • 2,900 Sq Ft

    5465 U S 4, Killington, VT 05751

    Live or work 2 minutes to Killington Resort's Skyeship Gondola! This unique property along the Route 4 flats is zoned mixed use for residential and/or commercial — it is currently split into 4 offices but permitting allows for up to 5 bedrooms (sleeps 10). The upstairs has a separate entrance in the back, so could be easily split into a duplex as well. So many opportunities! The flat driveway

    David White OwnerEntry.com

    5465 U S 4, Killington, VT 05751
  • /45

    $1,199,000

    • 10 Beds
    • 11 Baths
    • 5,970 Sq Ft

    70 N Main St, Rutland, VT 05701

    ONE HUNDRED THOUSAND PRICE ADJUSTMENT. CALLING ALL INNKEEPERS! RUTLAND IS IN NEED OF A CLASSY INN!This distinguished property has been the recipient of “Best of the Best” nine years running. With the expansion of the Killington Ski Area, this is the time! Previously operated as a successful Bed and Breakfast for 21 years, this magnificent home, with extensive renovations, still holds active

    Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

    70 N Main St, Rutland, VT 05701
  • /43

    $1,450,000

    • 5 Beds
    • 3.5 Baths
    • 4,262 Sq Ft

    960 E Pittsford Rd, Rutland, VT 05701

    HALF MILLION DOLLAR PRICE ADJUSTMENT. A working equestrian estate that lives like a luxury country retreat. Exceptional curb appeal begins with a paved driveway lined by handsome wood posts and lanterns. Set on 28 acres with breathtaking views of the Green Mountains and Killington and Pico peaks, this 1850s farmhouse was taken down to the studs and exquisitely renovated with exceptional

    Freddie Ann Bohlig Four Seasons Sotheby's Int'l Realty

    960 E Pittsford Rd, Rutland, VT 05701
  • /55

    $1,350,000

    • 5 Beds
    • 4 Baths
    • 3,640 Sq Ft

    96 Old Coach Rd, Killington, VT 05751

    This stunning Coventry Log Home, situated on 2.11 acres, is a true gem for outdoor enthusiasts and those seeking a peaceful mountain escape year-round. An added bonus is the ancillary unit with a separate entrance located over the garage.Savor breathtaking views of both Pico and Deer's Leap mountains. The elevated balcony deck is the perfect spot to enjoy a winter evening watching the snow

    James Hurley Four Corner Properties LLC

    96 Old Coach Rd, Killington, VT 05751
  • /36

    $598,000

    • 5 Beds
    • 3 Baths
    • 3,040 Sq Ft

    77 Belmont Rd, Mount Holly, VT 05758

    Discover this exceptional multi-family property offering three updated units, just 7.2 miles from the world-renowned Okemo Mountain Resort. Featuring two spacious 2-bedroom units and one charming 1-bedroom unit, this property is perfect for an owner-occupant seeking supplemental income or an investor looking for strong rental potential in a highly desirable location. Each unit has been

    Matthew Bellantoni Mary W. Davis Realtor & Assoc., Inc.

    77 Belmont Rd, Mount Holly, VT 05758
  • /40

    $499,900

    • 5 Beds
    • 2.5 Baths
    • 3,808 Sq Ft

    1186 Route 133, West Rutland, VT 05777

    IRA: Stately Spacious Colonial with 5 bedrooms, including a 1-bedroom in-law suite/apartment (separate propane furnace), which isn't being rented currently as family uses entire house as a single family. Also, there's an attached heated 3-car garage with 11' ceiling and 10' doors, an entry mudroom and utility room. Low maintenance as exterior has vinyl siding and roof is slate and standing seem.

    Melissa Loughan Westside Real Estate

    1186 Route 133, West Rutland, VT 05777
  • /34

    $399,000

    • 5 Beds
    • 4 Baths
    • 2,501 Sq Ft

    328 Main St, Poultney, VT 05764

    Back on the open market at a reduced price, this elegant Greek Revival home sits at the edge of Poultney, Vermont's Historic Main Street. Known as The Two Editors Inn, it honors two of Poultney's notable citizens, Horace Greeley and George Jones, who honed their printing skills locally before founding The New York Tribune and The New York Times. This home showcases the elegance and romance of the

    Suanne Ohl Northland Real Estate

    328 Main St, Poultney, VT 05764
  • /60

    $1,499,000

    • 5 Beds
    • 4 Baths
    • 5,006 Sq Ft

    2427 Monument Hill Rd, Castleton, VT 05735

    Discover your Vermont sanctuary just 2 miles from stunning Lake Bomoseen and a short drive to the scenic Half Moon State Park! This exceptional home offers a perfect blend of natural beauty and luxurious comfort nestled within over 80 acres of lush land. Imagine waking up to breathtaking water features - a deep spring-fed pond, a majestic fifty-foot waterfall, and a tranquil year-round brook

    Michael Johnston Coldwell Banker Hickok and Boardman

    2427 Monument Hill Rd, Castleton, VT 05735
  • /39

    $970,000

    • 6 Beds
    • 5 Baths
    • 3,817 Sq Ft

    3261 Route 30 N, Castleton, VT 05735

    LAKE BOMOSEEN DUPLEX - TWO HOUSES WITH INCOME: 1930 Southern house has original frame, but house was totally renovated in 1989 and Northern house was built. Southern house has 4-bedrooms, 2 1/2 baths and Northern house has two 1-bedroom apartments. New electrical, plumbing, insulation, etc. In 2024, houses were stained. Also, includes storage room between the houses and a storage shed near the

    Owen Loughan Westside Real Estate

    3261 Route 30 N, Castleton, VT 05735
  • /52

    $574,900

    • 5 Beds
    • 2 Baths
    • 2,940 Sq Ft

    6614 Main Rd, West Haven, VT 05743

    Finally removed from the auction and ready for your offers. Don't miss out on this opportunity! The Seller has had an inspection completed. Please see the Inspection report under the documents tab. A Breathtaking 105-Acre Estate with Endless Possibilities Welcome to a one-of-a-kind property offering exceptional versatility and timeless beauty. Set on 105.11 acres of land, this historic Greek

    Linda Benoit Highland Realty

    6614 Main Rd, West Haven, VT 05743
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