Rutland County VT Homes for Sale

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  /56

  $725,000

  Open Sun 11AM - 2PM $100K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 4,421 Sq Ft

  269 Hortonia Rd, Fair Haven, VT 05743

  Luxury Designer Home on 5 Scenic acres. Experience the perfect balance of privacy, natural beauty, and modern luxury in this custom-designed George Chandler home. Thoughtfully crafted with exceptional attention to detail, the home offers refined architectural design with Hubbardton Forge lighting, artistic details, This one-of-a-kind property features picturesque views, mature trees and a

  Spa

  Primary Bedroom Suite

  Waterfall on Lot

  5.4 Acre Lot

  269 Hortonia Rd, Fair Haven, VT 05743

  

  Nancy Liberatore

  
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  /60

  $465,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,100 Sq Ft

  224 Holden Rd, Chittenden, VT 05737

  Welcome to your ideal Vermont retreat at 224 Holden Road! Nestled on 3 private, mostly flat wooded acres in popular Chittenden, this beautifully maintained classic Cape offers the perfect blend of peaceful seclusion and convenient accessibility. Step inside to find an inviting open floor plan designed for effortless entertaining and quality time.The main level delivers the convenience of

  

  KC Gandee

  Real Broker LLC

  224 Holden Rd, Chittenden, VT 05737
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  /35

  $499,000

  $51K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft

  26 Park St, Brandon, VT 05733

  Walk to everything from this stately brick beauty! Thoughtfully and completely renovated, this stunning home seamlessly blends timeless character with modern updates. Improvements include a gorgeous new kitchen, updated bathrooms, refinished floors, new windows, spray foam insulation, boiler, water heater, electrical, plumbing, and much more. The flexible floor plan features a first-floor bedroom

  

  Beth Stanway

  IPJ Real Estate

  26 Park St, Brandon, VT 05733
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  /36

  $679,000

  • 3 Beds
  • 2.5 Baths
  • 2,460 Sq Ft

  7 High St, Brandon, VT 05733

  Some know it as the Bow House, others call it the Acorn House, but perhaps it's time to call it home. Rich in charm and character, this distinctive residence draws inspiration from the rare New England bow roof tradition, a style rooted in Maritime craftsmanship and celebrated for its graceful curved roofline. Originally influenced by the techniques of shipwrights and carpenters who built wooden

  

  Amey Ryan

  IPJ Real Estate

  7 High St, Brandon, VT 05733
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  /47

  $399,000

  $50K PRICE DROP

  • 3 Beds
  • 6 Baths
  • 3,323 Sq Ft

  1330 & 1340 Grove St, Brandon, VT 05733

  Well-located investment property along the Route 7 corridor, equidistant between Middlebury and Rutland and just minutes from downtown Brandon. The main building features a street-level commercial space currently operating as a successful yoga/pilates studio (with specialized heating for hot yoga), offering excellent visibility and ample on-site parking. Residential components include a

  

  Amey Ryan

  IPJ Real Estate

  1330 & 1340 Grove St, Brandon, VT 05733
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  /50

  $749,000

  • 3 Beds
  • 3 Baths
  • 3,339 Sq Ft

  353 Schoolhouse Rd, Whiting, VT 05778

  Very few properties offer beautiful views, privacy, acreage and modern conveniences in a way that feels effortless like this property does. At 353 Schoolhouse Road, the first thing you'll notice is the quiet. Set on more than 15 private acres, the property invites you to slow down and enjoy Vermont at its best. Open fields, mature woods, private walking trails, a pond, and a gentle stream create

  

  Sarah Peluso

  IPJ Real Estate

  353 Schoolhouse Rd, Whiting, VT 05778
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  /28

  $577,777

  $120K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft

  10 Old Town Rd, Castleton, VT 05735

  Motivated Sellers!! Bring all offers today!! Welcome to this enchanting lakefront retreat, where rustic charm meets lakeside living. Nestled in a quiet bay with over 200 feet of lakefront this property includes a dock so you can start enjoying Lake Bomoseen today! Get away from the city with your own tranquil escape. Located just a short drive Killington and Pico this home offers a year-round

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  10 Old Town Rd, Castleton, VT 05735
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  /11

  $224,900

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  141 Roberts Ave, Poultney, VT 05764

  Welcome home to this inviting 3-bedroom, 1-bath village residence perfectly situated on a desirable corner lot. Offering a blend of comfort, convenience, and small-town charm, this property provides ample space for everyday living both inside and out. Step inside to find comfortable living spaces, well-sized bedrooms, and plenty of natural light throughout. The corner-lot location enhances curb

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  141 Roberts Ave, Poultney, VT 05764
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  /58

  $649,000

  $40K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,176 Sq Ft

  2721 Vermont 155, Mount Holly, VT 05742

  The Best of Vermont Living.At the heart of the home, a custom-crafted chef’s kitchen serves as a welcoming gathering place, while warm wood floors and an open living area create an inviting atmosphere for everyday living and effortless entertaining. Throughout the residence, oversized windows frame expansive country views, grounding you in the natural beauty of your

  

  Gail Beardmore

  Engel & Völkers Okemo

  2721 Vermont 155, Mount Holly, VT 05742
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  /8

  $129,900

  • Land
  • 10.09 Acres
  • $12,874 per Acre

  4878 Stage Rd, Benson, VT 05743

  Reduced 10-Acre Wooded Retreat with Primitive Camp – Prime Vermont Hunting Land Discover your own slice of the Green Mountain State with this 10-acre wooded parcel nestled in the heart of Vermont. Perfect for outdoor enthusiasts, this secluded property offers a peaceful setting ideal for hunting, camping, or simply escaping the hustle of everyday life. Tucked away among mature hardwoods and

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  4878 Stage Rd, Benson, VT 05743
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  /13

  $345,000

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

  66 Murphy Dr, Hubbardton, VT 05732

  Welcome to this charming, move-in-ready home nestled on a beautifully landscaped 1.10-acre lot. Meticulously renovated, this inviting property showcases quality upgrades throughout, blending modern comforts with cozy Vermont charm. Surrounded by mature landscaping and vibrant flower beds, this secluded paradise offers the perfect balance of privacy and natural beauty. During the fall and winter

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  66 Murphy Dr, Hubbardton, VT 05732
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  /8

  $224,900

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 696 Sq Ft

  3516 Route 30 N, Castleton, VT 05735

  Charming 2-bedroom, 1-bath cottage offering breathtaking panoramic views of Lake Bomoseen. Nestled in a peaceful setting, this inviting retreat combines classic lake cottage charm with stunning scenery and a relaxing atmosphere. Bright and airy living spaces are filled with natural light, while large windows showcase spectacular water views from sunrise to sunset.The cozy interior

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  3516 Route 30 N, Castleton, VT 05735
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  /58

  $149,500

  $30K PRICE DROP

  • Land
  • 10.7 Acres
  • $13,972 per Acre

  0 Applesauce Hill Rd, Castleton, VT 05735

  Discover the perfect opportunity to own 10.7 acres of scenic Vermont land on Applesauce Hill Road in Castleton. This expansive parcel offers a beautiful mix of rolling terrain, open clearings, and wooded areas, creating an ideal setting for your dream home, private retreat, or recreational getaway. Enjoy stunning mountain views from multiple vantage points, including long-distance views of Pico

  

  Jacob Barnes

  EXP Realty

  0 Applesauce Hill Rd, Castleton, VT 05735
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  $295,000

  • 2,320 Sq Ft

  855 North St, Brandon, VT 05733

  Whether you're looking for your first home with income potential or your next investment property, this versatile Brandon property offers plenty of opportunity to build equity. Live in one apartment while the rental income from the second helps offset your mortgage, or lease both units and add a solid income-producing property to your portfolio. Currently configured as two apartments separated by

  

  Beth Stanway

  IPJ Real Estate

  855 North St, Brandon, VT 05733
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  /4

  $60,000

  $45K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  44 E Main St, Poultney, VT 05764

  Village Home with Restoration PotentialSet in a charming village location, this spacious 4 bedroom, 3 bath home is ready for restoration and offers endless potential. Featuring classic architectural details and a traditional layout, this property awaits your vision to bring it back to life. A detached garage provides convenient storage or workshop space. Located close to local shops, schools,

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  44 E Main St, Poultney, VT 05764
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  /52

  $395,000

  • 3 Beds
  • 2 Baths
  • 2,226 Sq Ft

  5187 Vt Route 103, Cuttingsville, VT 05738

  Discover the perfect blend of comfort and character in this beautifully updated bungalow, nestled in the heart of Cuttingsville. Ideally positioned for convenience, you are just a short drive from the amenities of both Rutland and Ludlow.This home has been thoughtfully renovated and meticulously maintained. Set back from the road, it is framed by enchanting perennial gardens that offer a

  

  Gail Beardmore

  Engel & Völkers Okemo

  5187 Vt Route 103, Cuttingsville, VT 05738
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  /29

  $539,000

  • 6,557 Sq Ft

  53-55 Vt Route 30 N, Castleton, VT 05735

  Motivated Seller!! Prime Location at Castleton Four Corners !! Three buildings offering multiple uses including 3 residential rental units, 1 commercial space and 1 large 32 x 80 storage barn. All units upgraded as rentals changed. Only 1 unit left to renovate with long term tenant. This property offers an excellent investment opportunity with a great return on investment!! Financial statement's

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  53-55 Vt Route 30 N, Castleton, VT 05735
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  /60

  $1,650,000

  $300K PRICE DROP

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

  1204 Bailey Rd, Cuttingsville, VT 05738

  Exceptional Shrewsbury Estate: 97-Acre Legacy PropertyOffered for the discerning buyer, 1204 Bailey Road presents a unique opportunity to acquire a substantial 97-acre parcel in the heart of Shrewsbury. This 5-bedroom, 4-bath, 2-story colonial boasts 4,719 sq. ft. of well-maintained living space, characterized by quality craftsmanship and timeless design.The property distinguishes

  

  Gail Beardmore

  Engel & Völkers Okemo

  1204 Bailey Rd, Cuttingsville, VT 05738
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  /46

  $1,100,000

  $199K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,110 Sq Ft

  2734 Healdville Rd, Mount Holly, VT 05758

  With winter just around the corner, one of the most important features in a ski house is a great MUDROOM! You need plenty of cubbies, hooks and room for gear. Here is the perfect mountain retreat near Okemo. Perched at over 2,100 feet, this exceptional contemporary home offers the ideal balance of luxury, privacy, and year-round adventure ...all just 15 minutes from Okemo Mountain

  

  Gail Beardmore

  Engel & Völkers Okemo

  2734 Healdville Rd, Mount Holly, VT 05758
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  /36

  $599,900

  $54K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,692 Sq Ft

  221 Fiddlehead Ln, Pittsfield, VT 05762

  A distinctive Vermont log home with space, privacy, and year-round versatility just 15 minutes from Killington. Set on 1.3 wooded acres in Pittsfield, this 3 bedroom, 1-bath home centers around a dramatic great room with cathedral ceilings, exposed beams, warm wood interiors, and a wood stove. A natural gathering space after a day on the mountain or simply at the end of the

  

  Sue Walsh

  BHHS Vermont Realty Group/Middlebury

  221 Fiddlehead Ln, Pittsfield, VT 05762
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  /20

  $260,000

  • 2,060 Sq Ft

  84 Crescent St, Rutland, VT 05701

  **Turn Key Buy and Hold Investment in Rutland City!**Looking for a solid buy-and-hold in Rutland City? This is it. This meticulously maintained multi-family has been extensively updated since 2020 and is ready for its next owner, including:- New electrical panel (2022)- Plumbing and electrical updates (2020)- New oil tank (2024)- New chimney (2021)- Complete

  

  KC Gandee

  Real Broker LLC

  84 Crescent St, Rutland, VT 05701
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  /52

  $439,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,642 Sq Ft

  50 Rosewood Ln, Bomoseen, VT 05732

  NEW PRICE $439,000! Tucked Away. Lake Access Included. This 4-bedroom, 2-bath home is located on a quiet dead-end road in the sought-after Crystal Beach community, offering the warmth and character of Vermont living with the added bonus of deeded access to Lake Bomoseen. An uplifting vaulted great room with rich knotty pine ceilings and walls, a cozy gas fireplace, Vermont slate flooring, and

  

  Sue Walsh

  BHHS Vermont Realty Group/Middlebury

  50 Rosewood Ln, Bomoseen, VT 05732
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  /3

  $224,900

  • 1 Bed
  • 1 Bath
  • 932 Sq Ft

  163 Murphy Dr, Hubbardton, VT 05735

  35-Acre Country Property with Well & SepticDiscover the possibilities on this beautiful 35-acre parcel of land! Offering a rare combination of privacy, space, and existing infrastructure, this property features a drilled well and septic system already in place, providing an excellent foundation for your future plans.Whether you're looking to build your dream home, create a private

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  163 Murphy Dr, Hubbardton, VT 05735
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  /60

  $379,000

  $48K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,440 Sq Ft

  769 Straight Rd, Belmont, VT 05730

  Perched above the Green Mountain National Forest on 12 private acres, this unique 3-bedroom, 2-bath Vermont homestead offers exceptional privacy, breathtaking long-range views, and the opportunity for a more sustainable lifestyle. Large windows capture ever-changing mountain and forest vistas, while natural light fills the living spaces throughout the day.The property features solar power

  

  Gail Beardmore

  Engel & Völkers Okemo

  769 Straight Rd, Belmont, VT 05730
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  /43

  $475,000

  • 2 Beds
  • 2.5 Baths
  • 2,734 Sq Ft

  1871 Rte 103, Mount Holly, VT 05758

  Historic Train Stationhouse! Unique design and character in a prime ski location on 4 acres with a private pond. This efficient historic gem was relocated to the current more convenient location with added acreage and a commercial outbuilding. The owned solar power offers low cost of living and years of energy benefits for new owners. This property features 2 bedrooms & 2 baths with beautiful

  

  Margretta Fischer

  Wohler Realty Group

  1871 Rte 103, Mount Holly, VT 05758
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  /27

  $280,000

  • 2,336 Sq Ft

  75 North St, Rutland, VT 05701

  Prime Income Property: 3-Unit Asset in Rutland City!Looking for a lucrative 3-unit multi-family property in Rutland City? This well-maintained investment at 75 North St has featured consistent capital improvements since 2022 and is fully ready for its next owner.Unit Breakdown & Property HighlightsUnit 1 (Ground Floor): Spacious 2-bedroom, 1-bath layout featuring generous

  

  KC Gandee

  Real Broker LLC

  75 North St, Rutland, VT 05701
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  /32

  $369,000

  • 2,400 Sq Ft

  6098 Route 140, Wallingford, VT 05742

  Investors and owner-occupants: take note! This well-maintained three-unit property in East Wallingford offers flexibility, income potential, and a convenient location. Whether you're looking to expand your rental portfolio, offset your mortgage with rental income, or create a multi-generational living arrangement, this property offers various possibilities.The upper-level apartment features

  

  Gail Beardmore

  Engel & Völkers Okemo

  6098 Route 140, Wallingford, VT 05742
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  /5

  $219,900

  $5K PRICE DROP

  • Land
  • 27,442 Sq Ft
  • $349,048 per Acre

  380 Columbia Dr, Hubbardton, VT 05732

  Permit for a 2 bedroom septic system is in process!! Here is your opportunity to own a lakefront lot. The prior cottage has been removed and there is a clean slate ready for lakefront dream! Featuring a secluded lot with private lake frontage and a 0.63 acre lot. Lake Beebe features a quaint community with no gasoline motors allowed, providing quiet water activities in a tranquil Vermont setting.

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  380 Columbia Dr, Hubbardton, VT 05732
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  /13

  $699,000

  $26K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,916 Sq Ft

  146 Lake Hortonia Rd, Sudbury, VT 05733

  Exceptional 8.5-Acre Lakefront Retreat on Lake HortoniaDiscover the perfect blend of privacy, versatility, and waterfront living with this remarkable 8.5-acre property on beautiful Lake Hortonia. Offering expansive lake frontage and peaceful natural surroundings, this unique estate is ideal as a year-round residence, vacation getaway, or investment opportunity.The main home

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  146 Lake Hortonia Rd, Sudbury, VT 05733
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  /60

  $262,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  5190 Whipple Hollow Rd, Pittsford, VT 05744

  Come see 5190 Whipple Hollow Road and discover your opportunity to own a beautiful Vermont country retreat at an attractive price. If you’ve been waiting for the right home, the time to see this one is now!Open House: Saturday, September 5th, 2026 from 12pm-1pm.Set on a picturesque country lot, this inviting, move-in-ready property offers the perfect blend of comfort, privacy, and

  Kathryn Zambon Real Broker LLC

  5190 Whipple Hollow Rd, Pittsford, VT 05744
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  /60

  $959,000

  $336K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 4,809 Sq Ft

  341 Turkey Farm Rd, Benson, VT 05743

  Motivated sellers offer major price reduction!Experience the ultimate in country living on this expansive property! This nearly 5,000 sq. ft. home, nestled on over 90 acres, features 500' waterfront on Lake Champlain, two large pastures and a paddock. The home has undergone numerous upgrades along with expanded finished square footage. The open floor plan is a chef's dream, showcasing a gourmet

  Stephanie Corey Adirmont Real Estate, LLC

  341 Turkey Farm Rd, Benson, VT 05743
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  /39

  $310,000

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,617 Sq Ft

  15 Stone Ridge Dr, Rutland, VT 05701

  Welcome home to this well-maintained 3-bedroom, 1-bath ranch located in one of Rutland City's most sought-after neighborhoods. Set on a level 0.34-acre lot, this bright and airy home offers comfortable one-level living with the added bonus of a partially finished lower level that provides plenty of extra space to fit your lifestyle. The main level features an inviting layout with abundant natural

  Betsy Adamovich Real Broker LLC

  15 Stone Ridge Dr, Rutland, VT 05701
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  /60

  $629,000

  $30K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,744 Sq Ft

  2091 N Lake Rd, Fair Haven, VT 05743

  Seventeen acres. Lake Champlain down the road. A setup that actually delivers on the Vermont lifestyle without the usual compromises. Set along North Lake Road in Benson, just moments from the Benson boat launch, this fully renovated farmhouse sits on a highly usable mix of open pasture and productive land. About five acres are mostly fenced for animals, with the balance level, hayed, and

  Betsy Adamovich Real Broker LLC

  2091 N Lake Rd, Fair Haven, VT 05743
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  /22

  $2,450,000

  • 4 Beds
  • 4 Baths
  • 5,707 Sq Ft

  324 Fellows Rd, Pittsfield, VT 05762

  Set within 210 acres of unspoiled forestland spanning Killington and Pittsfield, Vermont, The Tweed River Estate is a truly one-of-a-kind property, a private sanctuary where nature and craftsmanship meet. Designed by a renowned architect, the bespoke home is a masterwork in its own right, with exposed beams, high-end custom woodwork, and windows throughout that fill every room with light. Every

  Thom Milke Fountains Land Inc.

  324 Fellows Rd, Pittsfield, VT 05762
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  /42

  $377,000

  • Land
  • 256.3 Acres
  • $1,471 per Acre

  Marshall Phillips Forest, Sudbury, VT 05733

  Marshall Phillips Forest offers a variety of terrain and habitats suitable for residential development, with hiking, nature viewing, and hunting all found within its 256 acres. Most of the forest showcases different tree species, and the value is detailed in the timber section below. There are sections of wetlands in the forest associated with small brooks that flow through the property. These

  Thom Milke Fountains Land

  Marshall Phillips Forest, Sudbury, VT 05733
• 

  

  /60

  $1,750,000

  $499K PRICE DROP

  • 12 Beds
  • 5.5 Baths
  • 6,491 Sq Ft

  957 Pleasant Valley Rd, Benson, VT 05743

  A once-in-a-lifetime opportunity to own an extraordinary 460-acre estate where timeless character, modern functionality, and breathtaking natural beauty converge. Located in the Champlain Valley Wine Varietal area, a pristine valley of rolling pastures, mature forests, and pastoral views, this remarkable property offers limitless possibilities from a thriving agricultural enterprise to an

  Alex Pintair Four Seasons Sotheby's Int'l Realty

  957 Pleasant Valley Rd, Benson, VT 05743
• 

  /2

  $44,900

  • Land
  • 2.6 Acres
  • $17,269 per Acre

  39 U S 4, Mendon, VT 05701

  Lot near Ski area 2.6 acres

  K4K LLC K4K LLC

  39 U S 4, Mendon, VT 05701
• 

  

  /29

  $399,000

  • 2,368 Sq Ft

  80 Brown St, Rutland, VT 05701

  Two beautifully renovated residences, one compelling opportunity: this newly listed Rutland City multifamily property combines modern comfort with the flexibility of two separate apartments. Each apartment offers a refreshed setting with contemporary appeal, giving residents spaces that feel current, inviting, and easy to enjoy. The upper level apartment features an electric fireplace in the

  Nancy Greenwood Watson Realty & Associates

  80 Brown St, Rutland, VT 05701
• 

  

  /35

  $499,000

  • 3,800 Sq Ft

  40 S Main St, Rutland, VT 05701

  Investors, take note: here's a four unit multi-family property that pairs steady rental income with a prime uptown Rutland location—a combination savvy buyers rarely stumble upon. Built for performance, this well-maintained solid building features separate utilities across its units, meaning tenants cover their own usage and you sidestep the headache of dividing bills every month. The first floor

  Nancy Greenwood Watson Realty & Associates

  40 S Main St, Rutland, VT 05701
• 

  

  /15

  $79,900

  • 3 Beds
  • 1 Bath
  • 962 Sq Ft

  18 Prospect St, Fair Haven, VT 05743

  Single-level ranch on a level 0.35-acre lot in Fair Haven with 962 square feet of finished living area, three bedrooms, one full bathroom, and five total rooms. The property is near downtown Fair Haven, local shops, dining, the Fair Haven Free Library, and the Fair Haven Town Green. The Town Green hosts community activities including a farmers market, summer concerts, movies, Spring Fling, and

  Chris Lawrence Trillionaire Realty

  18 Prospect St, Fair Haven, VT 05743

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