Historic & Antique Homes

This search features single-family homes built before 1945. Properties are listed by price in order from high to low. You may change your sort order below, and you can refine your search by checking or unchecking the search criteria (or sliding the criteria bar) along the right side of this page.

414 - 416 Dorset Hollow Road Dorset VT 05251

Dorset, VT414 - 416 Dorset Hollow Road

Price$1,595,000

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 income opportunity. The possibilities are endless with space to expand and enhance.

Listed by Steven Bryant of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

816 Popple Dungeon Road Chester VT 05143

Chester, VT816 Popple Dungeon Road

Price$850,000

Est. Mortgage: $/month

MLS Number 4848206

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,676

Welcome to Deer Valley Farm also known as the Williams Homestead. This is the first time the property has been offered for sale in over 60 years! The home has been lovingly cared for with lots of improvements over the decades of ownership. Outside: The barn has undergone major work which insures its stability for years to come and includes a wine cellar. It measures 45x105 with plenty of room for cars, toys or animals. Other improvements include stonework, tennis court and pool with pool house and gardens. The walking bridge over the Williams River includes 4 staircases to the river and built in lights. The home is styled with Italian tile throughout and offers cozy antique charm with 3 fireplaces. The home does need updating but will be well worth the effort. The structure itself has been well maintained. The large acreage easily lends itself to a few other incredible homesites. Located just outside the town of Chester less than 4 hours to NYC and 2.5 hours to Boston. Minutes to all of Southern Vermont amenities including Okemo, Stratton, Killington, Vermont Country Store, Weston Playhouse, world-class golf and the shops in Manchester. This property will not disappoint.

Listed by Lisa Kelley of Cummings & Co

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

722 Route 100 Londonderry VT 05155

Londonderry, VT722 Route 100

Price$799,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4855153

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,760

Nestled against the backdrop of forests and Magic Mountain's ridgeline, this quintessential vintage home with multiple barns, summer stables, a pond and meadow is the pristine Vermont setting you look for in a property steeped in history. Meticulously maintained, this property exudes character and historical features with modern day comfort and care. The main house features wide pine floors, multiple working fireplaces, comfortable gathering spaces and an abundance of light with orientation to the meadow, pond and beautiful grounds. The inviting ambiance will welcome you, your family and friends and the formal dining room with fireplace will be a focal point of many evening meals. A magnificent sunroom with eastern orientation brings the outdoors in during each season and opens to lovely stone terraced patios for a front row seat to outdoor activities and the peaceful observance of Mother Nature. The main house offers 2760 SF with country kitchen, living room, dining room, sun room all with great attention to detail. The en-suite second floor master features vaulted ceilings with beams, a wood burning fireplace, large walk in closet and lovely views overlooking the pond and mountain ridgeline. A hall guest bedroom, bath and sleeping loft complete the second floor. A main floor lodge room with beams and wonderful fieldstone fireplace and en-suite bath also serves as the fourth bedroom. A garage barn with a game room and barn with 1bedroom guesthome + 6000SF Barn

Listed by Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

Historic Weston Village Home

41 Lawrence Hill Road Weston VT 05161

Weston, VT41 Lawrence Hill Road

Price$744,900

Est. Mortgage: $/month

MLS Number 4825595

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 6
  • Square Feet 4,492

This gorgeous historic/vintage house has been very well cared for and updated as appropriate --the wide pine wood floors and weathered beams immediately give a warm and classic feel. With approximately 4500 square feet of finished living space spread out over 2 and half stories, this is a very special and comfortable property. The sixteen rooms are amazing. A huge master bedroom/master bedroom suite on the second floor is impressive. With a great number bedrooms and a loft area this home provides opportunities for large families and friends to gather. It is only a few hundred yards from the village green, the specialty shops in Weston, and the Weston Playhouse. This is a special Weston property and a must see spectacular home. A new furnace and new oil tank were installed in March 2021.

Listed by Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

698 Vermont RT 11 Chester VT 05143

Chester, VT698 Vermont RT 11

Price$650,000

Est. Mortgage: $/month

MLS Number 4820671

  • Residential Single Family
  • Construction Existing
  • Bedrooms 10
  • Bathroom 12
  • Square Feet 6,848

An Amazing opportunity to own a 1810 Brick federal style home that is rich in local history and one of the most historic homes in Chester. It's had many reincarnations over the 2 century's of its existence. Starting as an old farmhouse it was converted to an Inn in 1942 and has been run as one ever since. It's been known as the Stone Hearth Inn and Tavern since 1982. It has been beautifully cared for by its current owners who have updated and maintained its elegance and down home charm. The Inn features 8 bedrooms mostly en-suite, a large formal dining room, Formal living room with a classic stone fireplace, office and a commercial kitchen. The home also features a separate 700 sq ft apt for additional income possibilities. Upstairs is a 2 bedroom owners quarters with full bath and living room. Attached to the Inn/Home is the 80 seat Tavern with refinished wood floors, gorgeous wood bar and wood stove. The property is special. Nearly 6 acres of open space, perennial gardens, back patio and direct groomed access to the VAST snowmobile trails. The possibilities here are endless. Large family home to live and work with great income potential with rentals, restaurant, tavern and even weddings. Run it or lease the spaces out. Ski clubs are another great possibility. Located just 2 miles from the Chester Green and only a short distance to major ski resorts, Okemo, Stratton, Bromley and Magic. Live the Vermont dream at this fantastic property.

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

38 Vt Rte 11 West Chester VT 05143

Chester, VT38 Vt Rte 11 West

Price$550,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4850599

  • Residential Single Family
  • Construction Existing
  • Bedrooms 12
  • Bathroom 5
  • Square Feet 5,976

Welcome to the Wylie House, a historic 12 bedroom, 5 bath home on .87 acres with many original details such as Victorian gingerbread, stained glass, an elegant period stairway and a rustic, original 2 story barn. The updated kitchen has attractive tile flooring, crown moldings, center island and a lovely eat-in area with a nook to enjoy morning coffee/tea. The living room has a brick hearth for a wood or pellet stove and built-ins for a great study/home office. The main bedroom features a lovely picture window overlooking the garden & a full bath w/clawfoot tub. An additional front bedroom could also serve as living area. Upstairs there are 2 baths, 5 bedrooms and a finished 3rd floor w/full bath, common area and two additional bedrooms. A 2004 addition adds a spacious gathering room that opens to the large rear deck. A huge, light and bright bonus space w/cathedral ceilings on the 2nd floor is perfect for yoga, a home theater, craft room or professional space. The attached rustic 2-story barn is an amazing space w/an efficiency kitchen, woodstove, full bath, laundry area and large picture window. A custom detailed stairway leads to 3 bedrooms on the 2nd floor. The yard has been lovingly cultivated with perennial gardens and features a garden cottage shed, outdoor sauna, workshop, studio/office wood storage and gazebo. An auto generator keeps things running smoothly and an outdoor wood boiler is a great alternative for heat! Next to town rec area & walkable to town.

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

174 Elm Street Manchester VT 05255

Manchester, VT174 Elm Street

Price$439,000

Est. Mortgage: $/month

MLS Number 4870872

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,800

This delightful American vernacular home in the heart of Historic Depot District combines in-town chic with farmhouse charm. Lovingly renovated with comfort in mind, its features include a stylish new kitchen, classically revamped baths, warm living spaces, cozy bedrooms, a peaceful back porch, landscaped urban farm grounds, an oversized two-car garage with office/storage, and close proximity to all that Manchester has to offer while only 10 minutes to the closest ski resorts! With something for everyone in every season, this is the one home you don't want to miss!

Listed by Adrienne Sherwood of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

3111 Dorset West Road Dorset VT 05251

Dorset, VT3111 Dorset West Road

Price$365,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4864676

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,738

OWN A PIECE OF DORSET HISTORY On the National Register of Historic Buildings this 1850 Colonial is a timeless classic.At the crossroads of scenic West Road and historic Church Street, 2 stately maples stand at the foot of a short marble walkway to the front entrance of this 3 bedroom, 2 ½ bath home. Simplicity and serenity distinguish the ambiance of the living room which spans the width of the house and includes a dining area off the central kitchen.The kitchen is a design opportunity to create and meet your own needs and tastes. Off the kitchen is a sun room, tv, reading room with French doors onto a marble patio and garden area. Another marble patio is at the back of the house and leads to an attached shed and mudroom entry with new tile flooring and renovated half bath, small den or computer room, laundry room with storage and direct access back into the kitchen. Upstairs are 3 corner bedrooms. The master suite has its own bathroom with shower and walk in closet. The 2 guest bedrooms share a hallway bath with soaking tub and shower. Lightness and brightness are enhanced by tall windows throughout. Flooring is both hardwood and softwood. A short walk Dorset Village, an historic gem, offers dining, charming inns, cafes, shopping, Dorset Theatre Festival. Outdoor activities abound with hiking, biking, riding, swimming, skiing at near by ski areas, more shopping and dining in Manchester plus theatre music and art. A haven from the world yet a world of lifestyle choices.

Listed by Diana Stugger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

17 Capen Road Winhall VT 05340

Winhall, VT17 Capen Road

Price$299,000

Est. Mortgage: $/month

MLS Number 4871026

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,609

This historic bright and cheery, 1860 c. Slade School House, sits upon .75 acres. Post and beams frame the living/kitchen area with vaulted ceilings, pellet stove and open dining alcove. Master bedroom w/ walk in closet, guest room and 2 bathrooms located on the 1st floor. Partial 2nd floor room offers office space, gym or potential 3rd bedroom. Hallway addition to the single car garage with plenty of storage space/attic with room to spare. Purchaser needs to understand there is a foundation issue that we have had a consult on. The price reflects the current conditions of the foundation and structure. Property is being offered "As Is". Call to get further documentation.

Listed by Elizabeth Romano of Josiah Allen Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

374 North Street Chester VT 05143

Chester, VT374 North Street

Price$279,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4867999

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,117

Located in the historic Chester stone village you will find this gem of property ready and waiting for its owner. This 3- bedroom 3- bath home offers everything you want in a village property. You will be greeted by full-length covered porch ideal for relaxing outside in a surprisingly private setting. The first floor features an entryway with 1/2 bath, the front room is formal dining room with hardwood floors with direct entry to the open updated kitchen which is located in the middle of house with views into the large living room that features a pellet stove fireplace insert that heats the room on those winter days and nights. The first floor also boasts a breeze way/sunroom that is currently being used as an office with access to a nice backyard deck. The second floor features 3- large bedrooms including the Master Bedroom with private bath. Another full bath is also on the second floor. Other highlights include first floor A/C, Replacement windows throughout and a 2-car attached garage. New roof over the porch section as well as the garage. The 1/2-acre property is lovely with perennial gardens, side yard and it borders a year-round stream. Just a mile to the Town Green and a short drive to Okemo Mountain this special home is affordably priced and well worth a look. Showing to begin 7-2-2021

Listed by Gary Coger of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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

Main Street Londonderry

2000 North Main Street Londonderry VT 05148

MLS Number 4871602

  • Residential Single Family
  • Construction Existing
  • Bedrooms 7
  • Bathroom 4
  • Square Feet 3,070

Are you looking for a home or investment property in the Londonderry area? Look no further, this affordable historic village house might just be the key to your next adventure. Located in the center of town, the main house offers 5BR/2.5BA on three levels and there is an accessory 2BR/1BA in-law apartment with kitchenette and living room over the garage. This well-maintained property is full of charm and potential, with newly refinished wood floors throughout, fireplace with pellet insert, spacious kitchen, high-speed internet and more. An energy audit in 2020 resulted in the installation of lots of new windows and foam insulation in the basement. Other recent improvements include new oil furnace 2015 and hot water heater in 2019. A breezeway leads from the attached two-car garage to the house and the private backyard area overlooks the West River as it meanders through town. Walk to the store for groceries, the farmers market on summer Saturdays and multiple restaurants are just a stone's throw away.

Listed by Mary Mitchell Miller Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 2021
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

Broker Reciprocity

Copyright 2021 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 July 31, 2021.