Our mobile site is optimized for smaller screens.

TRY IT NO THANKS

and narrow your search. If you have fewer than 200 results, you can save your search.

Windsor County

r=211-220
366 Crimson Hawk Road Plymouth VT 05056

Plymouth, VT366 Crimson Hawk Road, Unit S1-24

Price$475,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5094522

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,308

Tucked within the Hawk community, this charming mountain retreat offers the perfect blend of privacy, recreation, and convenience. Set within a private 1.09-acre wooded lot, owners are also able to enjoy access to Hawk's common land with room to explore, including trails ideal for snowshoeing, hiking, and cross-country skiing. Perfectly positioned between Killington and Okemo Mountain, and just minutes to area lakes and scenic Route 100, this location is ideal for year-round Vermont living and exploring. Inside, the open kitchen, dining, and living area is filled with natural light from large windows that frame the peaceful wooded setting. A beautiful stone fireplace with a wood stove insert creates a warm and inviting focal point, perfect after a day on the slopes or trails. The dining area opens to a spacious deck, offering an easy transition to outdoor living and quiet moments surrounded by nature. The lower level features three bedrooms, including charming built-in storage and built-in bunks that make this a fun and functional escape for younger guests. Whether used as a vacation getaway, ski retreat, or four-season home base, this Hawk property captures the relaxed mountain lifestyle in a setting that feels wonderfully private while remaining close to everything the Okemo Valley and Killington region have to offer. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Sarah Sheehan of William Raveis Real Estate Vermont Properties

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

547 Williams Road Chester VT 05143

Chester, VT547 Williams Road

Price$474,900The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5085214

  • Residential Single Family
  • Full Bath 1
  • Address 547 Williams Road
  • Bedrooms 3
  • Bathroom 2

MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The rooms are nicely sized and in close proximity to bathrooms. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has an en suite with a full bathroom and lots of closet space! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won't want to miss on your home buying adventure! Truly a stunning property with so much to offer!

Listed by Terri Edgerley of Edge Realty Vermont

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

586 Ski Tow Road West Windsor VT 05037

West Windsor, VT586 Ski Tow Road

Price$474,800The price has recently decreased

Est. Mortgage: $/month

MLS Number 5084265

  • Residential Single Family
  • Full Bath 1
  • Address 586 Ski Tow Road
  • Village Brownsville
  • Bedrooms 3

Adorable partially furnished 3 bedroom, 2 bath home on landscaped 1.53 acres corner lot in the heart of Ascutney Mt Resort! Many upgrades including Bosch High Efficiency Propane Boiler, Mitsubishi heat pump/AC, Rinnai on demand hot water heater, new well tank & centrifuge filtration system, new fireplace & chimney with Woodstock soapstone woodstove flanked by custom cabinets on each side. Decks, extensive perennial gardens, pond, vegetable garden area & fruit trees. Outbuildings for various storage needs. Automatic/timed lighting on granite posts line the driveway. At Ascutney Outdoors; walk to hiking & mountain biking, skiing & tubing just outside your door! Selling due to job situation. Ascutney Mountain has protective covenants including rights of 1st refusal.

Listed by Dana Waters and Paula Waters of Dark Horse Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

501 Stoughton Pond Road Weathersfield VT 05151

Weathersfield, VT501 Stoughton Pond Road

Price$472,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5083955

  • Residential Single Family
  • Full Bath 1
  • Village Perkinsville
  • Bedrooms 3
  • Bathroom 3

Tucked into the charming village of Perkinsville on 3.8 acres, this unique residential and commercial property offers the perfect balance of opportunity, lifestyle, and connection. You will be moments away from Stoughton Pond, hiking trails, and within driving distance to some of Vermont's most sought-after ski resorts. For years, this property has been a gathering place-Saturday nights around the kitchen table, laughter filling the home, and a trusted shop where neighbors came not just for service, but for connection. Now, it's ready for its next chapter. One level home of comfortable living, with an open-concept kitchen, dining, and living area designed for both everyday life and easy entertaining. 3 bedrooms and 2.5 baths provide flexibility, including a primary bedroom with an oversized closet. The enclosed, heated front porch offers additional living space and convenience, complete with a washer and dryer. The walk-out basement expands the possibilities. Ample ceiling height, workshop area, second laundry setup, ¾ bath, and a bonus room ideal for an office or creative space is a functional extension of the home. A classic Vermont touch-the built-in dumbwaiter-makes bringing firewood upstairs simple and efficient. The 2 story garage/shop stands ready for its next purpose, featuring multiple bays with car lifts, high ceilings, heat, and a half bath. Whether you continue its legacy, launch a new business, or create the ultimate workshop, this space is ready to support your vision. Additional outbuildings with concrete floors and covered storage areas provide ample room for equipment, tools, recreational vehicles, and more. A property with this kind of flexibility, history, and heart doesn't come along often. Bring your ideas, your business, and your creativity-and make it your own.

Listed by Marie Elena Potter and Kathleen Metcalf of EXP Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

133 Stagecoach Road Norwich VT 05055

Norwich, VT133 Stagecoach Road

Price$470,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5076379

  • Residential Single Family
  • Full Bath 1
  • Address 133 Stagecoach Road
  • Bedrooms 2
  • Bathroom 1

Situated on a private 4.6 acre lot this unfinished home is awaiting your vision to compete it. Currently a 2-bedroom 1 bath in a lower-level walkout, awaiting the second story. You can live in the home and complete it in your own time frame or bring a builder and finish it now to your specifications. The home is a 44 ft x 26 ft base and can be a single or two story above. It has a 4-bedroom septic system, artesian well with Penteck Intellidrive constant pressure controller, underground utilities, radiant heat plumbed under the slab. The home is oriented for maximum solar gain with a south facing front. The lot is a mix of wood and open meadow with room for gardens or a small orchard. Privately located off a dead-end road, the absence of street noise allows one to relax and listen to the birds and wildlife. Owner is a licensed real estate agent.

Listed by Linda White of EXP Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

649 Spencer Hollow Road Springfield VT 05156

Springfield, VT649 Spencer Hollow Road

Price$465,000The price has recently decreased

Est. Mortgage: $/month

Pending

MLS Number 5087456

  • Residential Single Family
  • Full Bath 2
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 3,466

Welcome to your dream retreat! Nestled on 10.10 sprawling acres of peaceful countryside, this beautifully maintained 3-bedroom, 3-bathroom single-family home offers the perfect blend of privacy, charm, and modern comfort. Step inside to discover vaulted ceilings that enhance the spacious, open-concept living area, complemented by warm natural light and serene views. The loft space, ideal as a cozy reading nook or creative corner, overlooks the main living area, adding architectural character and versatility. Enjoy morning coffee or evening sunsets from the large deck, or relax year-round in the enclosed porch, perfect for taking in the tranquil surroundings no matter the season. The partially finished basement offers two additional rooms for additional storage, bedroom or an office. Outdoors, offers your own private pond adds a touch of serenity and natural beauty to the landscape-ideal for quiet reflection or fun with family and friends. With over 10 acres to explore, there's plenty of space for gardening, recreation, or even expanding your dream homestead. Please Do NOT drive up the driveway to look at the house as they have dogs.

Listed by Peggy Winchester of ACORN REAL ESTATE GROUP LLC

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Save FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

191 Route 100 North Ludlow VT 05149

Ludlow, VT191 Route 100 North

Price$455,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5090515

  • Residential Single Family
  • Full Bath 1
  • Address 191 Route 100 North
  • Bedrooms 5
  • Bathroom 2

Nestled between Okemo Mountain and the lakes region, this inviting 5-bedroom home sits on 2 peaceful acres framed by mature trees and an expansive open yard. Filled with warmth and character, the home is a charming reminder of simpler times, offering large sun-filled rooms and generous gathering spaces throughout. At the heart of the home is the open kitchen and family room, where a cozy wood stove creates the perfect setting for relaxing with family and friends. French doors lead to a spacious deck overlooking the beautiful backyard - an ideal spot for morning coffee, summer entertaining, or simply enjoying the peaceful surroundings. The home features five bedrooms, beautiful wood floors rich with history and character, and recent improvements including a newly replaced septic tank by the current owner. With its timeless appeal, spacious layout, and wonderful setting, this property presents an exceptional opportunity to restore and elevate a classic Vermont home to its next chapter.

Listed by Suzanne Garvey of Mary W. Davis Realtor & Assoc., Inc.

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

2140 Brandon Mountain Road Rochester VT 05767

Rochester, VT2140 Brandon Mountain Road

Price$450,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5064748

  • Residential Single Family
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,656
  • Acreage 2.61

Tucked away on a picturesque 3-acre lot, this classic three-bedroom expanded Cape offers privacy, seclusion, and wonderful views in a beautiful Rochester valley setting. Set nearly 700 feet back from the road and bordering the Green Mountain National Forest, the property enjoys a tranquil natural backdrop where a scenic pond at the edge of the land attracts birds and wildlife. The main level features a comfortable living room with a woodstove, an open kitchen and dining area, a cozy keeping room connecting to the attached two-car garage, a half bath, and a screened porch for enjoying summer evenings. Upstairs, you'll find three bedrooms and a full bath, including a spacious primary bedroom with vaulted ceilings, exposed beams, and a private balcony overlooking the landscape. With a fresh interior paint job just completed, this property has all the makings of a truly special retreat - ideal as a quiet primary home or peaceful mountain getaway. Price reduced - call today!

Listed by Kyle Kershner of Killington Pico Realty

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

20 Edwin's Pond Road Rochester VT 05767

Rochester, VT20 Edwin's Pond Road

Price$450,000The price has recently decreased

Est. Mortgage: $/month

MLS Number 5082087

  • Residential Single Family
  • Full Bath 2
  • Address 20 Edwin's Pond Road
  • Bedrooms 3
  • Bathroom 3

Set on a quiet, rural corner lot just off Middle Hollow Road, this contemporary Vermont home offers a compelling blend of efficiency, flexibility, and long-term upside. Built in 1989 with a durable standing seam metal roof and solid wood-frame construction, the home provides 3+ bedrooms and 2.5 baths across a thoughtfully scaled footprint, with additional finished space in the walkout lower level. A drilled well, septic system, and 200+ amp electrical service support comfortable year-round living, while fiber optic internet makes remote work a realistic option in this peaceful setting. The standout feature-and where this property truly separates itself-is the oversized two-car garage with a large, flexible space above. The current ½ bath was designed with an eye for expansion into a ¾ bath plus a galley kitchen. Whether you envision an in-law apartment, guest suite, home office, or studio, the infrastructure is in place to unlock significant added value. With the ongoing demand for flexible living arrangements in the Rochester market, this is a rare chance to complete a high-impact improvement without starting from scratch. The lot itself offers a classic Vermont feel: just over an acre, wooded, and private, while still maintaining easy access to a publicly maintained road. The walkout basement and multi-level layout create opportunities for separation of space, storage, or expansion depending on your needs. Rochester continues to be one of the most sought-after towns in the Upper White River Valley, known for its strong sense of community, access to outdoor recreation, and proximity to destinations like the Green Mountain National Forest, hiking and biking networks (check out the Ridgeline Outdoor Collective), and multiple ski areas. The village center offers a charming mix of local amenities, while still feeling tucked away from the busier corridors of the state.

Listed by William Brokhof of Vermont Backcountry Real Estate

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

127 Trombley Road Andover VT 05143

Andover, VT127 Trombley Road

Price$449,000The price has recently decreased

Est. Mortgage: $/month

Active With Contract

MLS Number 5064459

  • Residential Single Family
  • Full Bath 1
  • Address 127 Trombley Road
  • Bedrooms 5
  • Bathroom 1

Set on 119 acres that stretch across Andover and Chester, this property combines 114 acres in Andover with 5 in Chester. The setting includes over 20 acres of flat, open meadows along the Williams River, framed by wooded hills and distant ridgelines. The forest is mixed with possible timber value as well as a nice sugarbush waiting to be tapped. The original farmhouse, approached by a town-maintained road and plowed right to your door, is ready for a complete restoration. Its form and orientation make it an ideal candidate for renovation, preserving the rural character that defines this part of Vermont. Several original outbuildings remain, including a tall silo, classic barns, and a sugarhouse-all reminders of the land's agricultural roots. Power and utilities are in place, and the road frontage provides easy access in all seasons. This is a solid opportunity for someone looking to rebuild, reimagine, or create a homestead with scale and history. Located between Chester, Weston, Londonderry, and the Okemo Valley, it offers both privacy and proximity to year-round recreation.

Listed by Daire Gibney of Barrett and Valley Associates Inc.

{$office->Name}

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

Do not fill in this field:

Do not fill in this field:

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Price Down Payment Interest Rate Years
%

Est. Mortgage: $/month

Federal 30-year interest rate: 6.48% last updated on 2026-06-04

This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Broker Reciprocity 

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated June 13, 2026 10:23 AM EDT

 

You Can Edit This Text

Custom Search

Luxury Home Guide