Our Southern Vermont Residential Listings

If you are looking for Real Estate in Southern Vermont, you’ve come to the right place! We specialize in Residential properties in Southern Vermont’s premier Ski Resorts like Stratton, Bromley, and Magic Mountains as well as the quintessential Vermont towns like Manchester and Dorset. Whether you are looking for a primary residence or a luxurious vacation home, country or mountain setting, close to town or private country setting with acreage, we have the property for you!

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74 High Meadow Road Winhall VT 05340

Winhall, VT74 High Meadow Road

Price$2,395,000

Est. Mortgage: $/month

MLS Number 4826982

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 5,460

Rare opportunity to own one on the finest homes at Stratton Mountain. This masterpiece of architectural and interior design is situated alongside the Stratton golf course with easy access to skiing. Luxurious finishes, family friendly floorplan and an incredible outdoor space defines this 3.6 acre estate at 74 High Meadow Road. The distinctive style is credited to original architect Mark P. Finlay, with extensive renovations by an exemplary firm that left no detail untouched. Eating at home is a delightful experience with the zen like ambiance in the kitchen, dining, and great room, with walls of windows and finishes in warm hues. Well equipped with a Viking 6 burner duel fuel stove, sub-zero fridge, and 2 dishwashers. The main floor master suite is privately sited in the home and includes mountain views. The living room loft has views of the slopes, and a special place to call a home classroom or office. Exercise room, and hot tub on the private stone patio. Three season porch, and destination fire pit. Central air-conditioning, radiant heat, backup generator, high speed internet, Crestron remote access system, 3 fireplaces, 2 sets of laundry, and 2 car garage are just a few of the essentials of this home. Skip the wait list at the private Stratton Mountain Club and be a member this season with this home. The site is 3 contiguous lots, allowing you to build a guest house in the future, or enjoy the level lawns for snowmen or swing-sets. Path to golf course to snowshoe.

Listed by Chrissy Carroccio and Karin Hardy of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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641 Wind Hill Road Manchester VT 05255

Manchester, VT641 Wind Hill Road

Price$1,995,000

Est. Mortgage: $/month

MLS Number 4821435

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 6
  • Square Feet 6,752

In the heart of Southern Vermont is 641 Wind Hill Road in Manchester. Sited on 10 acres, the mature garden and landscape makes for a private setting while enjoying big mountain views and all day sunshine. The open concept living spaces flow, while always keeping the wall of windows and the view of Equinox in sight. The newly renovated hardwood flooring throughout is fresh and tasteful, as is the newly renovated kitchen. The first floor master is a true retreat, with a fireplace, sitting area, custom built in walk in closets and a beautifully appointed en suite bath. The den off the master makes working remotely inspiring. The second level features three en suite bedrooms with more mountain views. An office with built in bookshelves and desk makes for a quiet work or school from home space, and the recreational room round out the second floor. Mirrored wall workout room is in the lower level. The three car attached garage is oversized, leaving plenty of room for skis, paddle boards, golf clubs, fishing rods, and all the gear that brings you out into Vermont's natural environment. This refreshed home is Vermont at its finest. Central air conditioning and backup generator. 2 miles to Manchester's restaurants, amenities, and golf. 10 miles to skiing at Bromley.

Listed by Chrissy Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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54 Red Clover Lane Mendon VT 05701

Mendon, VT54 Red Clover Lane

Price$1,800,000

Est. Mortgage: $/month

MLS Number 4821494

  • Residential Single Family
  • Construction Existing
  • Bedrooms 17
  • Bathroom 22
  • Square Feet 15,486

The Red Clover Inn is ready for its next chapter…a private family compound, group ski club or Airbnb --- traditional farm house, plus two lodging buildings and a barn. This property is ideally situated on 12.8 secluded acres adjacent to Pico, State Forest and near Killington ski mountains and the Long Trail/hiking and mountain biking. Featuring 17 guest bedrooms and 22 bathrooms within three buildings, the property boasts a classic red barn. The 60 + person restaurant and pub in the main house make great gathering spaces. The Mountain Top Inn & Resort, a short 15 minute drive away, offers year- round activity including horseback riding, 60km of XC, lake activity, kayaking/canoeing, clay bird and spa. There are endless options to create a four-season family getaway. Come and stay a night to fully experience the possibilities. There is the opportunity to continue operating the property as an Inn or consider a hybrid approach.

Listed by Steven Bryant of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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414 - 416 Dorset Hollow Road Dorset VT 05251

Dorset, VT414 - 416 Dorset Hollow Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 4830516

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,672

Incredible privacy with access to all village amenities, this estate with sweeping mountain views on 19 secluded acres in Dorset Hollow, is just 1/3 mile to the village. Stone pillars greet as one gently climbs a meandering drive to this historic 1930's "Enfield” house moved to this site where it received renewed foundation and life. A private sanctuary, this exceptional location offers a unique lifestyle opportunity supporting the sporting land lover, pets, or agricultural interest over a mix of open fields and hardwood forest. A 2004 restoration opened up the circular floor plan offering gathering spaces centered around a well-appointed country kitchen featuring a large marble island and great room with vaulted ceilings, enhanced architectural interests with natural light and fireplace. The dining room extends to the outside deck and leads to an additional living room. All gathering spaces boast wood burning fireplaces! The main level master suite features a private wood paneled study with fireplace, marble tile bath and views. The center hall staircase leads to 2 additional bedrooms and baths. The lower level offers a private bedroom suite with its own entry, as well as, the garage, laundry room and ample storage. In addition to all of this, a charming one bedroom guest cottage with fieldstone fireplace offers ideal guest lodgings or an income opportunity. The possibilities are endless with space to expand with additional buildings and other land improvements.

Listed by Steven Bryant of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1532 Morse Hill Road Dorset VT 05251

Dorset, VT1532 Morse Hill Road

Price$1,299,000

Est. Mortgage: $/month

MLS Number 4681331

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,400

Fabulous property located at the top of Overlook and Wind Hill Roads on Morse Hill Road in Dorset, Vermont. With 58 acres, open meadow, forest, brook, and views to the south, this property is ready for your imagination! The farmhouse is a classic style and has been in the family for over 50 years. This property is available in its entirely - house with 58 acres.

Listed by Paul W. Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1702 North Puckerbrush Road Reading VT 05062

Reading, VT1702 North Puckerbrush Road

Price$1,250,000

Est. Mortgage: $/month

MLS Number 4819286

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 5
  • Square Feet 7,374

A magical property located in the hills of Reading surrounded by large country properties in the heart of horse country. State Forest land abuts this property. This home is a perfect retreat for those seeking solitude. The sweeping drive carries you through the woods to the home-site which is centered in an open area totally hidden from the town gravel road. Pleasant view are here now, with dramatic views if you chose to thin the woodland below. Walking the grounds you will find a natural landscape with added fruit trees, a new barn with storage for 2 or 4 cars and a loft, a hidden back field and even an ancient "lime kiln'. Inside there are so many quality features that you may have only dreamed about...the top of the line kitchen with Sub-Zero freezer and fridge, Wolf range, refrigerator drawers, cookbook library, and a separate prep room known as the 'gadget room'. There is an office, den, living, dining room on the first floor along with screen porch to the rear. There are two wings to the second floor..giant master suite with abundant storage and a stunning bath along with two guest rooms and a laundry room that will make you want to do your laundry. The other wing would be a perfect in-law suite or nanny's quarters with two sleeping rooms, sitting room, full bath and washer/dryer. The lower level has a large family room, gallery, exercise room and 2 storage areas. This property is second to none with Okemo and Woodstock just miles away. Be sure to check out the video!

Listed by Betty McEnaney of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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3378 30 Route Dorset VT 05251

Dorset, VT3378 30 Route

Price$875,000

Est. Mortgage: $/month

MLS Number 4784534

  • Residential Single Family
  • Construction Existing
  • Bedrooms 15
  • Bathroom 14
  • Square Feet 6,589

This time-honored Vermont bed and breakfast has been a reputable place to find peace and comfort in downtown Dorset for many years now. Boasting eleven guest rooms, each with their own private bath, this inn is one of the quintessential places to stay when visiting the area. With several fine dining experiences within a 1/2 mile distance and both Bromley and Stratton merely a short drive away, new owners could settle down effortlessly knowing the location can't be beat.

Listed by Paul W. Carroccio and Marek Kovac of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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300 Fairway Meadows Road Windham VT 05359

Windham, VT300 Fairway Meadows Road

Price$840,000

Est. Mortgage: $/month

MLS Number 4816573

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 4,036

Paradise for the Sportsman and Outdoors Woman - Live in Year Round Luxury! If you ever wanted to leave the "rat race" behind and find your own paradise and peace and quiet in Vermont... this idyllic spot is for you. It's like having your own resort and special hideaway! Total privacy on 28+ acres with 270 degree views, including the peaks and trails of Okemo in the distance. This fabulously unique timber frame, designed by Pete Newton and built by Scott Wilkins Custom Home Builders will captivate your imagination. What it is and what it could be! Literally 100's of thousand of $$$'s of gorgeous Windham Dark Green Ledge Slate from this very property, makes up the massive and dramatic wood burning fireplaces inside and the slate also lines the huge Vt. country pool/pond and huge patio area. Pool area also with a Vt. timber beam Cabana for serious outdoor entertaining. The home enjoys Southern sunny exposure in all the living areas. Incredible living room, master bedroom and kitchen all flowing out to poolside summer living and splendid mature gardens in bloom. Entertaining is world class with pool table and state of art golf simulator with over 200 courses to test your skills. Just a short direct access to the VAST snowmobile trails. Enjoy ALL that Vermont has to offer in EVERY season. Magic, Stratton and Okemo all within 25 minutes. Come see this magnificent home.

Listed by Wilkie Bushby of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19 Mtn View Road Chittenden VT 05737

Chittenden, VT19 Mtn View Road

Price$675,000

Est. Mortgage: $/month

MLS Number 4816951

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,916

Sweeping VIEWS of Vermont's Green Mountain National Forest and the Chittenden Reservoir, this house can be an investment opportunity as part of the Mountain Top Inn & Resort rental program ($50K plus potential, plus personal use) and/or the ideal retreat in a four season resort community offering year round activities. Offered fully furnished (turnkey), this light-filled home offers sweeping views from the expansive deck and large picture windows. Move in condition, every room has new mountain rustic furnishings, carpet and paint. Ample master features king bed, gas fireplace, built-ins with desk, walk-in closet, large bath with jetted tub and private balcony. The other three bedrooms have queen beds. Spacious living room offers multiple gathering areas anchored by a large brick wood burning fireplace and hard wood flooring. Eat-in kitchen enjoys the views with island and cozy breakfast nook that opens to the deck. Adjacent dining room accommodates overflow guests. First floor laundry room, full basement for storage and games, oversized two car garage with additional storage. Walking distance to the resort, lake and trails. Within minutes of Killington and Pico downhill skiing. The best location and ever changing views in town! Move right in and start taking advantage of all this home and resort have to offer.

Listed by Steven Bryant of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1532 Morse Hill Road Dorset VT 05251

Dorset, VT1532 Morse Hill Road

Price$499,000

Est. Mortgage: $/month

MLS Number 4707295

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 2
  • Square Feet 2,400

Fabulous property located at the top of Overlook and Wind Hill Roads on Morse Hill Road in Dorset, Vermont. Seller is offering this property to be subdivided at Buyer's option for 10+/- open meadow acres, and views to the south, this property is ready for your imagination! The farmhouse is a classic style and has been in the family for over 50 years. This property is available in this part as house with 10 acres or in its entirely as house with 58 acres under MLS Listing # 4681331.

Listed by Paul W. Carroccio of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6225 Main Street Manchester VT 05255

Manchester, VT6225 Main Street

Price$475,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4817677

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,356

Amazing income producing property with Main House, Cottage and Apartment above the detached garage! Excellent rental history for both the cottage and the apartment! The Antique Colonial Main House built in 1804 is up to date with 3 bedrooms and 3 baths. Master suite with attached bath, large dining room with massive hearth, living room, and study both with fireplaces. The detached cottage has a front porch, one bedroom, kitchen/living and dining area with loft. Over the detached 3 bay garage with room for 2 cars and workshop, there's an apartment with rear entrance to the second floor and includes one bedroom, bath, and kitchen / living and dining area. There's also a small deck off the living room. An extraordinary property just outside of downtown Manchester, Hunter Park and Riley Rink. The Golf Range is just across the yard and you're just off the new rail to trail path connecting downtown to North Rd. Property includes several sheds and 1.22 landscaped acres.

Listed by Greg Cutler of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule TourAsk A QuestionMore Details

472 Main Street Chester VT 05143

Chester, VT472 Main Street

Price$450,000

Est. Mortgage: $/month

MLS Number 4822226

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 7
  • Square Feet 5,546

This is one of a kind! Whether you are looking for a home for your family and guests, or something that you can use for a home business, this one is for you. It isn't often that you find a house in this condition-just look at that porch. Located just a short distance to the village green, shops and eateries. In the other direction you will find the Chester recreation area for pool, tennis, and hiking. You have your choice of ski mountains with Okemo, Magic, Bromley and Stratton all a short drive away...golf, fishing, hiking, biking and so much more that Vermont has to offer. The home is lovely. There is a large kitchen, dining room and living room for formal relaxation. An office and first floor bedroom and full bath, too. Upstairs are 4 more bedrooms and 3 more baths. There is a back staircase off the kitchen. The back end of the house is where fun can happen. There is a bar and sitting area along with two rec rooms, currently with ping-pong, air hockey, billiards and poker tables! In addition, there is a large multipurpose room...exercise, shop, studio, rental space....you decide! The fiber optic internet means you can stay in touch with work or take in your favorite movies. The landscaping is very attractive. Off the back of the house, there is a private deck that overlooks the huge, flat back yard. Every inch of it is usable for play or gardens! There is much to love here and in Chester. Offered mostly furnished. Be sure to take in the video to see all there is to offer.

Listed by Betty McEnaney of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2020 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 November 29, 2020.