Rutland County VT Homes for Sale

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  /39

  $929,000

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  325 Dean Hill Rd, Killington, VT 05751

  This exceptional 3-bedroom, 2-bath home located on Dean Hill Road in Killington offers the perfect blend of comfortable mountain living, investment opportunity and year-round adventure access. Ideally positioned within walking distance of public transportation and just off The Killington Road, this fully furnished and equipped residence offers easy access to everything the region offers—skiing,

  Bret Williamson Killington Valley Real Estate

  325 Dean Hill Rd, Killington, VT 05751
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  /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
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  /32

  $279,000

  • 2 Beds
  • 1.5 Baths
  • 1,395 Sq Ft

  24 S Main St Unit 2, Rutland, VT 05701

  The Sycamore Inn — A Piece of Vermont History, Reimagined for Modern Living Rich in history and timeless appeal, The Sycamore Inn occupies part of the stately mid-1800s residence once known as the Governor's Mansion. Thoughtfully restored into a limited collection of condominium homes in the early 1980s, it preserves the craftsmanship and architectural character of its era while offering the

  Mark Triller Real Broker LLC

  24 S Main St Unit 2, Rutland, VT 05701
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  /37

  $114,900

  • 3 Beds
  • 2 Baths
  • 2,396 Sq Ft

  2990 US Route 7, Pittsford, VT 05763

  Opportunity awaits at 2990 US Route 7 in Pittsford! This approximately 1,904 sq. ft. two-story home offers a flexible canvas for the right buyer. Originally configured as a 3-bedroom, 2-bath residence, the property is ready for a full renovation and presents excellent potential to create a spacious single-family home or explore conversion to a duplex, subject to local approvals. With a full

  

  Hughes Group Team

  Casella Real Estate

  2990 US Route 7, Pittsford, VT 05763
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  /24

  $175,000

  • 1 Bed
  • 1 Bath
  • 696 Sq Ft

  2358 Route 100 Unit 102, Pittsfield, VT 05762

  Enjoy Vermont living and four-season recreation from this spacious first-floor, one-bedroom condo in the Wintergreen complex. Whether you're looking for a weekend retreat, investment opportunity, or affordable home base near the mountains, this unit offers comfort, convenience, and flexibility. The open-concept floor plan creates a bright and inviting living space, with the kitchen, dining, and

  Betsy Adamovich Real Broker LLC

  2358 Route 100 Unit 102, Pittsfield, VT 05762
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  /58

  $979,000

  • 4 Beds
  • 3.5 Baths
  • 3,380 Sq Ft

  243 Cricket Hill Rd, Killington, VT 05751

  Nestled in a picturesque and private Killington setting, this inviting 4-bedroom, 3.5-bathroom home offers the perfect combination of comfort, functionality, and timeless appeal. Set on a beautiful 5 acre lot with a scenic pond and charming gazebo, the property provides a peaceful backdrop for year-round enjoyment, whether you're sipping your morning coffee by the water or taking in the beauty of

  Kaitlyn Hummel Prestige Real Estate of Killington

  243 Cricket Hill Rd, Killington, VT 05751
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  /59

  $2,675,000

  • 3 Beds
  • 5 Baths
  • 4,321 Sq Ft

  426 Roaring Brook Rd, Killington, VT 05751

  This Stunning home has an amazing location on the 4th hole of Killington Golf Course in the heart of Killington Resort! It has an extraordinary combination of golf course frontage and unobstructed vistas of the Killington Mountain range. Enjoy total privacy while being less than a half a mile to the downtown restaurants, and less than 2 miles to the Killington Base lodges. The recent renovations

  Gretchjen Smith Williamson Group Sothebys Intl. Realty

  426 Roaring Brook Rd, Killington, VT 05751
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  /8

  $619,000

  • 3 Beds
  • 1 Bath
  • 984 Sq Ft

  361 Johnson Spooner Rd, Castleton, VT 05735

  Lakefront Opportunity on Lake Bomoseen! With 100 feet of pristine shoreline and sparkling water views, this property offers endless possibilities. The existing three-bedroom, one-bath cottage was updated in 2019 and features a charming living room, an updated kitchen, and a welcoming screened porch and deck overlooking the glistening waters of the lake. Whether you're looking for an affordable

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

  361 Johnson Spooner Rd, Castleton, VT 05735
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  /12

  $499,000

  • 3,951 Sq Ft

  36 S Main St, Rutland, VT 05701

  Solid 1900 multi-family boasting nearly 4,000 sq. feet of living space. Currently set up as a 4-unit, may be a possibility to convert an office space into a fifth apartment. Clean updated Three 2-bedrooms and an efficiency adding 4 much needed apartments in Rutland City's repertoire. The house features spacious bedrooms with large closets, impressive living areas and tall ceilings. A large

  Nancy Greenwood Watson Realty & Associates

  36 S Main St, Rutland, VT 05701
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  /41

  $489,000

  • 5 Beds
  • 1 Bath
  • 1,472 Sq Ft

  1044 Point of Pines Rd, Castleton, VT 05735

  Step into timeless Adirondack charm with this beautifully updated turn-of-the-century cottage located in the sought-after Point of Pines Cottage Colony Association. Rich in character and classic lake-style appeal, this inviting home blends historic craftsmanship with thoughtful modern upgrades. Recent improvements include updated electrical throughout, a renovated kitchen and bath, and tasteful

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  1044 Point of Pines Rd, Castleton, VT 05735
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  /50

  $995,000

  • 3 Beds
  • 1 Bath
  • 1,298 Sq Ft

  48 Acorn Lodge Rd, Castleton, VT 05735

  OPEN HOUSE JUNE 30TH 11 AM - 3PM! A once-in-a-generation opportunity to own one of the most extraordinary and iconic properties on Lake Bomoseen. Tucked away on the private point of Acorn Lodge, behind Rabbit Island, this storybook lakefront retreat occupies one of the most coveted settings on the entire lake. Surrounded by water on multiple sides, the property offers unmatched panoramic views

  

  Hughes Group Team

  Casella Real Estate

  48 Acorn Lodge Rd, Castleton, VT 05735
• 

  

  /41

  $1,429,000

  • 4 Beds
  • 3 Baths
  • 3,092 Sq Ft

  2643 Sugar Hill Rd, Wallingford, VT 05773

  A Private Vermont Sanctuary on 135 Spectacular Acres Set on an extraordinary 135-acre parcel of rolling hills, open meadows, and peaceful woodlands, this lovely and stylish country retreat offers exceptional privacy and timeless Vermont beauty. Built in 1985, the contemporary home is enhanced by underground utilities that preserve the natural landscape and create a true sense of sanctuary. The

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

  2643 Sugar Hill Rd, Wallingford, VT 05773
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  /26

  $215,000

  $20K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  40 East St, Middletown Springs, VT 05757

  This newly renovated home in the charming village of Middletown Springs is just a short walk to the town green and country store. Cook up a storm in the modern eat-in kitchen with plenty of cabinet space, then unwind in the spacious living room with its cozy brick fireplace. The first floor features a primary bedroom, a freshly updated 3/4 bath, and a laundry room. Upstairs offers another nicely

  Suanne Ohl Northland Real Estate

  40 East St, Middletown Springs, VT 05757
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  /39

  $420,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,401 Sq Ft

  55 Fox Hollow Village Unit 1, Mendon, VT 05701

  Enjoy comfort and convenience in this spacious, light-filled condominium at Fox Hollow Village. Ideally located directly across from Pico Mountain and on the shuttle route to Killington Resort, this property offers easy access to year-round outdoor recreation and excellent rental potential. The open-concept living area features cathedral ceilings, a floor-to-ceiling brick fireplace, and access to

  Kerry Dismuke RE/MAX North Professionals

  55 Fox Hollow Village Unit 1, Mendon, VT 05701
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  /32

  $515,000

  Open Fri 4PM - 6PM

  • 3 Beds
  • 2.5 Baths
  • 3,012 Sq Ft

  125 Maplewood Dr, Rutland Town, VT 05701

  **Rutland Town Executive Ranch!** Beautifully positioned at the end of a quiet dead-end road on 1.5 level acres, this impeccable home offers the perfect combination of privacy, quality, and exceptional outdoor living. Bordering Rutland Town watershed land, the setting is peaceful and secluded while remaining just minutes from shopping, dining, medical facilities, and recreation. The backyard is

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

  125 Maplewood Dr, Rutland Town, VT 05701
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  /47

  $429,000

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  168 & 170 Brenda Rd, Clarendon, VT 05759

  Set on 2.13 private acres in North Clarendon, this unique “as is” property offers a rare opportunity for buyers seeking space, versatility, and potential.The property includes a ranch style single family home, and a two-stall barn with two one-bedroom apartments, along with two outbuildings, creating a variety of possibilities for owner-occupants, investors, hobby farmers, or those looking

  Mark Triller Real Broker LLC

  168 & 170 Brenda Rd, Clarendon, VT 05759
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  /15

  $65,000

  • Land
  • 32,670 Sq Ft
  • $86,667 per Acre

  00 Sharon Dr Unit 12, Rutland, VT 05701

  RUTLAND CITY: Building lot located in desireable residential area, in city outskirts, bordering Combination Pond with water views. Public water and sewer available at street and buyer will need State of Vermont waste water permit to build and hook-up. Close to Pico and Killington ski areas, Rutland Hospital, shopping, restaurants and Rutland Airport.

  Melissa Loughan Westside Real Estate

  00 Sharon Dr Unit 12, Rutland, VT 05701
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  /41

  $387,500

  • 3 Beds
  • 2 Baths
  • 3,485 Sq Ft

  48 Church St, Rutland, VT 05701

  Join us for an Open House this Saturday 11-1 and discover The Black Pearl, the jewel of the neighborhood. This stunning 3-bedroom, 2-bathroom home was taken down to the studs and meticulously rebuilt for modern, effortless living. New plumbing, 200-amp electrical service, updated insulation, and a new hot water heater give you the confidence of a home that is essentially brand new from the inside

  Leo Pond Four Seasons Sotheby's Int'l Realty

  48 Church St, Rutland, VT 05701
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  /60

  $799,000

  $40K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 5,975 Sq Ft

  89 Sherri Ln, North Clarendon, VT 05759

  Sweeping Mountain Views provides a stunning backdrop for this spacious 6,000+ square foot home, offering 4 bedrooms, 4.5 baths, a flexible floor plan, and a private one-bedroom in-law apartment on 3.7 picturesque acres.Designed for both everyday living and entertainment, the main level features soaring cathedral ceilings, expansive windows, and an open-concept layout that fills the home with

  Mark Triller Real Broker LLC

  89 Sherri Ln, North Clarendon, VT 05759
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  /9

  $200,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft

  118 Park Ave, Rutland, VT 05701

  New Price! Roll up your sleeves and let your imagination run wild this three-bedroom, one-bathroom house is bursting with potential and waiting for someone ready to bring their vision to life. Calling all dreamers, do-it-yourself enthusiasts, and savvy investors: this fixer upper offers a genuine opportunity to build sweat equity and create something truly your own. The bones are here, the layout

  Nancy Greenwood Watson Realty & Associates

  118 Park Ave, Rutland, VT 05701
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  /40

  $455,000

  • 4 Beds
  • 2.5 Baths
  • 2,853 Sq Ft

  6 Moonbrook Dr, Rutland, VT 05701

  Welcome to this beautifully appointed 4-bedroom, 3-bath contemporary home located at 6 Moon Brook Drive in Rutland City. Designed with both comfort and entertaining in mind, this spacious residence offers an inviting blend of quality finishes including Hubbardton Forge light fixtures, thoughtful updates, and a desirable location. The main level features an impressive eat-in kitchen with rich

  Leona Minard Four Seasons Sotheby's Int'l Realty

  6 Moonbrook Dr, Rutland, VT 05701
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  /7

  $65,000

  • Land
  • 1.15 Acres
  • $56,522 per Acre

  13s Mountain View Dr, Pittsford, VT 05763

  Picture the home you've always sketched in your mind, then imagine the perfect blank canvas to bring it to life. This vacant parcel in Pittsford offers exactly that—an opportunity to build your Vermont vision from the ground up, with mountain views thrown in as a daily bonus. Tucked along a quiet dead-end street shared by just three neighboring homes, this lot delivers the kind of peace that's

  Brian Hill Remax Summit

  13s Mountain View Dr, Pittsford, VT 05763
• 

  

  /45

  $299,000

  • 4 Beds
  • 2 Baths
  • 1,260 Sq Ft

  207 Church St, Rutland, VT 05701

  Nothing to do here. Just move in. This 4 bedroom 2 Bath City home has been completely remodeled right down to the studs and subfloors. 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

  Rick Ouellette Rutland Realty

  207 Church St, Rutland, VT 05701
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  /20

  $130,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft

  155 Dorr Dr Unit S5, Rutland, VT 05701

  RUTLAND CITY: Recently renovated modern 1-bedroom second floor condominium with lovely mountain views. Spacious kitchen remodeled with new cabinets, laminate flooring, and granite counters with breakfast bar. Appliances new in 2019. Some personal furniture will be included. Located in the outskirts of Rutland City, close to Killington and Pico Ski areas, Lake Bomoseen, shopping, restaurants and

  Melissa Loughan Westside Real Estate

  155 Dorr Dr Unit S5, Rutland, VT 05701
• 

  

  /45

  $450,000

  • 2 Beds
  • 1 Bath
  • 963 Sq Ft

  653 Saw Mill Hill Rd, Wells, VT 05774

  LOG HOME, 10 ACRES, HORSE BARN. Is your love for riding horses, hunting, hiking or soaking in the great outdoors; if so, let the adventure begin right here with this story book setting. Hidden on 10 acres of complete privacy with a 24'x30' two story horse barn with heated artist studio ( this space would also make a great office space with lots of natural light), paddock, stonewalls, the sweetest

  Lori Andrus-Winn New England Lakeside Realty

  653 Saw Mill Hill Rd, Wells, VT 05774
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  /47

  $449,000

  $31K PRICE DROP

  • 6 Beds
  • 3.5 Baths
  • 3,108 Sq Ft

  153 Eagle Rock Rd, Pittsfield, VT 05762

  Hidden away on a quiet dirt road in the heart of Pittsfield, this charming 6-bedroom chalet offers privacy, character, and endless potential. Surrounded by Vermont's natural beauty, you'll enjoy easy access to nearby hiking, biking, and snowmobile trails, while being just 20 minutes from Killington Resort. The home features three levels of living space, two cozy fireplaces/woodstoves, and an

  Tucker Adirondack Lange Lange & Lange

  153 Eagle Rock Rd, Pittsfield, VT 05762
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  /43

  $625,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,844 Sq Ft

  457 Brooklyn Rd, Danby, VT 05739

  Tucked into the heart of Vermont’s mountain landscape, this lovingly restored 1850 farmhouse offers the rare combination of historic charm, modern comfort, and an exceptional natural setting. Surrounded by sweeping valley views and located beside the Big Branch Wilderness and Otter Creek, 457 Brooklyn Road captures the peaceful beauty that makes Vermont so special.This spacious 4-bedroom,

  David Shehadi Josiah Allen Real Estate, Inc.

  457 Brooklyn Rd, Danby, VT 05739
• 

  

  /51

  $639,000

  $56K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,272 Sq Ft

  1174 N Main St, Danby, VT 05739

  Set on 13.6 picturesque acres with sweeping mountain views and gently rolling fields, this beautifully updated farmhouse captures the essence of Vermont living. Offering 4 bedrooms and 3 bathrooms, the home seamlessly blends timeless character with modern updates, including a renovated kitchen and bathrooms, new flooring, fresh interior paint, a new boiler, water softener, a weatherized basement

  David Shehadi Josiah Allen Real Estate, Inc.

  1174 N Main St, Danby, VT 05739
• 

  

  /8

  $995,000

  $100K PRICE DROP

  • Land
  • 2.17 Acres
  • $458,525 per Acre

  1678 Killington Rd, Killington, VT 05751

  This 2+ acre commercial parcel offers approximately 362 feet of frontage on Killington Road, presenting a rare opportunity in the heart of Killington’s Commercial Zone. Ideally located near the ski area and the planned Ski Village, the property sits within one of Vermont’s most established and highly visible resort commercial corridors. The mostly level site offers excellent potential for

  Bret Williamson Killington Valley Real Estate

  1678 Killington Rd, Killington, VT 05751
• 

  

  /45

  $949,000

  $36K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,338 Sq Ft

  289 Ledgemere Point, Hubbardton, VT 05732

  One-of-a-kind yet quintessential year-around lake cottage. Every detail and furnishing has been curated to evoke the timeless Northern Lake House. And this property is being sold fully furnished and outfitted, so it’s ready to enjoy now. Driving into the circular driveway you notice at once the connection of house with the land. From the cedar log framed shed to the main beams of the house, it

  Dave Carlson Lake Homes Realty, LLC

  289 Ledgemere Point, Hubbardton, VT 05732
• 

  

  /5

  $74,900

  • Land
  • 1.3 Acres
  • $57,615 per Acre

  4 Prospect St, Fair Haven, VT 05743

  1.3 acres of flat blacktopped property with major state road frontage. Such a great opportunity with so many options of things that can be done with the property. A corner of the parcel sits in a flood plain, but much of the land does not. All you need is your imagination to make it so many different things.

  Cynthia Hollister NY and VT Real Estate Company

  4 Prospect St, Fair Haven, VT 05743
• 

  

  /60

  $875,000

  • 3 Beds
  • 1 Bath
  • 1,592 Sq Ft

  709 Little Sherburne Rd, Killington, VT 05751

  Escape to the privacy and tranquility of this unique off-grid property nestled on approximately 98 acres in Killington. Surrounded by nature and offering direct access to an extensive network of snowmobile trails, this three-bedroom home is ideal for outdoor enthusiasts or anyone seeking a peaceful retreat. A standout feature of the property is its abundance of established fruit plantings. More

  Laura Derderian Killington Valley Real Estate

  709 Little Sherburne Rd, Killington, VT 05751
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  /34

  $589,000

  $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,300 Sq Ft

  5876 US Route 7, Pittsford, VT 05763

  Stately Colonial with 10 Private Acres and Spectacular Western Mountain Views. Perched atop a beautiful knoll and privately situated on 10 acres, this exceptional four-bedroom, three-bath home offers timeless charm, warmth, and breathtaking western sunsets. A winding driveway leads to the residence, creating a wonderful sense of arrival and complete privacy. Offering approximately 2,700 square

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

  5876 US Route 7, Pittsford, VT 05763
• 

  

  /60

  $649,000

  $10K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,532 Sq Ft

  275 Chittenden Rd, Chittenden, VT 05737

  New Price! Must see! Welcome to 275 Chittenden Road, a classic Vermont Farmhouse fully refinished set on 1.2 level acres with frontage along East Creek. Offering 4 bedrooms, 2 full baths, and 2,532 finished square feet, this 1850 home blends historic charm with warm, updated living spaces and flexible options for today’s lifestyle. This fully remodeled home from the studs must be seen in person

  Christopher Williams Flex Realty

  275 Chittenden Rd, Chittenden, VT 05737
• 

  

  /8

  $250,000

  • 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 features an

  

  Nancy Liberatore

  Lakes & Homes Real Estate

  3516 Route 30 N, Castleton, VT 05735
• 

  

  /3

  $40,000

  • Land
  • 30,492 Sq Ft
  • $57,143 per Acre

  64 Sangamon Rd, Pittsford, VT 05763

  Priced to sell! Affordable wooded lot in Pittsford. Conveniently located just off a main road, this property offers a private setting while remaining close to local amenities and an easy commute to nearby towns. Wastewater/septic design plans are available, helping streamline the development process. An older mobile home currently exists on the property and is being conveyed as-is with no value

  Brooke Woodard Watson Realty & Associates

  64 Sangamon Rd, Pittsford, VT 05763
• 

  

  /26

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,352 Sq Ft

  45 Eden Ave, Proctor, VT 05765

  Tucked into a peaceful hillside setting in the heart of Proctor, 45 Eden Avenue offers the charm of a classic Vermont home with thoughtful modern updates throughout. This 3-bedroom, 2-bath home features an updated kitchen with modern appliances, refreshed first-level flooring, bathroom improvements and mini-splits for added comfort. Set on approximately 1.1 acres, the property offers a private

  Joshua Lemieux Remax Summit

  45 Eden Ave, Proctor, VT 05765
• 

  

  /44

  $59,000

  • 1 Bath
  • 413 Sq Ft

  228 E Mountain Rd Unit 137, Killington, VT 05751

  Aggressively priced sleep four studio unit for sale at the Killington Grand Resort Hotel, Killington's premeire slope-side fractional ownership property! Unit 137 Interval Use Period IV is a studio unit that sleeps 4 guests on a queen sized murphy-bed plus a sofa bed. Ownership entitles the owner to 13 weeks of use per year. Studio units are in very high demand! A full kitchen with fridge, stove,

  Doug Quatchak Killington Valley Real Estate

  228 E Mountain Rd Unit 137, Killington, VT 05751
• 

  

  /42

  $524,600

  $24K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,148 Sq Ft

  608 Orchard Hill, Pittsford, VT 05763

  Set along desirable Orchard Hill in Pittsford, this distinctive Tudor-inspired home offers timeless curb appeal, comfortable living space, and a beautiful 1.3-acre setting. The exterior blends brick, stucco-style accents, dark trim, mature landscaping, and a welcoming front entry, creating a property with warmth and character from the moment you arrive. Inside, the home features an inviting

  Joshua Lemieux Remax Summit

  608 Orchard Hill, Pittsford, VT 05763
• 

  

  /58

  $699,999

  • 5 Beds
  • 3.5 Baths
  • 2,523 Sq Ft

  97 Stewart Ln, Cuttingsville, VT 05738

  Set on more than 8 acres in the village of Cuttingsville, this versatile property combines a spacious open-plan home, established evergreen plantings, extensive outbuildings, and a unique Vermont lifestyle opportunity. A standout feature is the substantial solar array paired with Tesla Powerwall battery storage, helping support much of the property's electrical needs while providing backup power

  Daire Gibney Barrett and Valley Associates Inc.

  97 Stewart Ln, Cuttingsville, VT 05738

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