Brownsville, VT Homes

/48
$1,689,000
- 3 Beds
- 3.5 Baths
- 3,294 Sq Ft
39 Elm St Unit B, Woodstock, VT 05091

The Richmond House – Unit B | Woodstock Village. An enduring Woodstock landmark, the iconic Richmond House (c.1826) is a distinguished brick Federal with a softly weathered, rose-hued patina and elegant architectural details. Set on over an acre behind a classic white picket fence, this historic property—reimagined under the direction of Laurence Rockefeller—comprises three luxurious residences

Zoe Hathorn Washburn Snyder Donegan Real Estate Group

39 Elm St Unit B, Woodstock, VT 05091
/15
$2,595 per month
- 3 Beds
- 2.5 Baths
- 1,800 Sq Ft
- Townhouse for Rent
2 Townhouse Way, Woodstock, VT 05091

Available November 1 2025 through April 30th 2026Fully Furnished. All utilities plus internet included - you write one check each month.Hello Lovers of Vermont Fall and Winter! Here is your chance to escape the hustle and bustle of your busy life in Vermont's premier village of Woodstock! This Townhouse is peaceful and private, with all the amenities to keep you in comfort AND quick

Matt DePrizio Covered Bridge RE

2 Townhouse Way, Woodstock, VT 05091
/24
$629,500 Sold Sep 12, 2025
- 1,650 Sq Ft
- $382/SF
- 17 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1885
40 Pomfret Rd, Woodstock, VT 05091

Welcome to Kingsley Cottage – A delightful and charming property situated in the pastoral landscape of the Prosper Valley in Woodstock. Meticulous energy efficiency upgrades of the property have been combined with an aesthetically sensitive preservation of the vintage charm. A spacious covered porch details the exterior envelope of the home – the perfect spot to enjoy outdoor dining,

Mary Mayhew Snyder Donegan Real Estate Group

40 Pomfret Rd, Woodstock, VT 05091

/39
Est $1,041,468 Not Listed For Sale
- 4 Beds
- 4 Baths
- 3,507 Sq Ft
433 Cowdrey Path, Woodstock, VT 05091

433 Cowdrey Path, Woodstock, VT 05091

/40
$3,500,000
- 6 Beds
- 6 Baths
- 5,433 Sq Ft
61 Academy Cir, Woodstock, VT 05071

Hyacinth House has been a landmark property in the historic village of South Woodstock from its early settlement in the 1800's. Sited on a knoll overlooking the Kedron Brook this grand residence has been carefully restored by talented craftsmen. Taking care to keep the beautiful original details the owners have brought the systems into the 21st century with the highest quality of materials. The

Carol Wood Williamson Group Sothebys Intl. Realty

61 Academy Cir, Woodstock, VT 05071
/28
$239,000 Sold Sep 11, 2025
- 816 Sq Ft
- $293/SF
- 15 Days On Market
- 1 Bed
- 1 Bath
- Built 1987
42 Heritage Condo Way Unit 16, Woodstock, VT 05091

OPEN HOUSE SAT AUG 2 FROM 10 - 12 Located less than 2 miles from the Woodstock Village Green, this immaculately maintained and move-in-ready condo offers comfort and convenience in a peaceful setting. Just eight steps down from the front foyer, the unit opens into a thoughtfully designed space ideal for single-level living.Inside, you’ll find laminate flooring throughout and a cozy

Franchesca Collins Hall Collins Real Estate Group

42 Heritage Condo Way Unit 16, Woodstock, VT 05091

/34
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
7429 Us Route 4, Bridgewater, VT 05034

7429 Us Route 4, Bridgewater, VT 05034

/43
$2,600,000 Under Contract
- 4 Beds
- 3.5 Baths
- 3,998 Sq Ft
2 Pleasant St, Woodstock, VT 05091

2 PLEASANT STREET- This stately brick Federal is a historic landmark property in the heart of Woodstock Village, home to many storied families in the town and state’s history, notably Julius Converse, Governor of Vermont in 1872, and Laurance Rockefeller. Though it has been well-renovated and maintained over the years, it retains many of its historic features to beautifully blend modern

David Donegan Snyder Donegan Real Estate Group

2 Pleasant St, Woodstock, VT 05091
/39
$613,000 Sold Sep 10, 2025
- 1,958 Sq Ft
- $313/SF
- 302 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1920
5851 South Rd, Woodstock, VT 05071

This charming home is an amazing opportunity to own a piece of history in the lovely village of South Woodstock , Vermont. Starting its life as the garage and home of Clyde Wood it has evolved over time with the present owners into a beautiful , meticulous residence. Much attention to detail can be found in every room from wide pine flooring to cathedral ceiling in the great room. The home is

Carol Wood Williamson Group Sothebys Intl. Realty

5851 South Rd, Woodstock, VT 05071

/27
Est $826,531 Not Listed For Sale
- 5 Beds
- 3 Baths
- 3,579 Sq Ft
7 Golf Ave, Woodstock, VT 05091

7 Golf Ave, Woodstock, VT 05091

/22
$645,000 Under Contract
- 3 Beds
- 1.5 Baths
- 1,468 Sq Ft
187 Dana Rd, Woodstock, VT 05091

This delightful gambrel cape offers a wonderful combination of thoughtful and charming updates, energy efficient upgrades, and a coveted and convenient location! An intelligent interior design offers an all-season functional flow for everyday living as well as entertaining. Step inside by way of a spacious entryway/mudroom that also has direct entry from the attached garage. One will find the

Mary Mayhew Snyder Donegan Real Estate Group

187 Dana Rd, Woodstock, VT 05091
/44
$1,900,000 Sold Sep 05, 2025
- 3,227 Sq Ft
- $589/SF
- 0 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2021
51 Watkins Way Unit 2, Woodstock, VT 05091

51 Watkins Way, Unit 2 – Woodstock Village, VermontExperience modern comfort and timeless Vermont vernacular style in this 2021 constructed 2,280 sq. ft. Elevator Barn Home duplex. Designed with Efficiency Vermont guidance, the home achieves exceptional energy performance with an estimated STR rating of 55–56, a true luxury level.Situated on a quiet private road, the property offers

John King Real Broker LLC

51 Watkins Way Unit 2, Woodstock, VT 05091

/30
Est $967,965 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,423 Sq Ft
12 High St, Woodstock, VT 05091

12 High St, Woodstock, VT 05091

/49
$1,595,000
- 5 Beds
- 3.5 Baths
- 3,648 Sq Ft
1522 Barnard Rd, Woodstock, VT 05091

Just 2 miles from Woodstock Village, this gracious brick cape on 6 open acres offers space, comfort, and classic Vermont charm. The expanded chef’s kitchen opens to a gracious gathering room ideal for entertaining, while 3 fireplaces—wood-burning, brick, and gas-ready—provide cozy warmth throughout. Upstairs, find 3–4 bedrooms including one with its own fireplace, plus a private guest room or

Keri Cole Williamson Group Sothebys Intl. Realty

1522 Barnard Rd, Woodstock, VT 05091
/33
$776,000 Sold Aug 25, 2025
- 2,552 Sq Ft
- $304/SF
- 6 Days On Market
- 3 Beds
- 3 Baths
- Built 1984
3 Hathorn Hill St Unit 3, Woodstock, VT 05091

Rare opportunity to own in Hathorn Hill Condos. Private, quiet with lovely fern grove and stonewalls with views to the East. This unit has an de-attached 2 bay garage with easy access to extra parking. Upper level consist of an open floor plan, abundance of natural light with slider doors across the front for nice views off balcony. Living room anchored by a handsome wood burning fireplace

Gretchjen Smith Williamson Group Sothebys Intl. Realty

3 Hathorn Hill St Unit 3, Woodstock, VT 05091

/38
Est $530,900 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,020 Sq Ft
39 South St, Woodstock, VT 05091

39 South St, Woodstock, VT 05091

/42
$8,000,000
- 3 Beds
- 3.5 Baths
- 6,096 Sq Ft
115 Eastman Rd, South Woodstock, VT 05071

Sorgenfrei, or "Carefree," was built by Ennis Construction in 2015, and this extraordinary property truly embodies that sobriquet. A stunning and uncommon confluence of the finest materials and the most energy efficient techniques, this home was carefully constructed to maximize worry-free enjoyment. The most advanced systems and a focused commitment to the highest quality make this home a

Keri Cole

115 Eastman Rd, South Woodstock, VT 05071
/40
$740,000 Sold Aug 18, 2025
- 2,688 Sq Ft
- $275/SF
- 67 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1975
339 Gully Rd, Woodstock, VT 05091

Peaceful Gully Road Retreat. Just minutes from Woodstock Village.Set on 5.1 private acres along quiet and desirable Gully Road, this beautifully updated four-bedroom, two and one-half bath home offers the perfect blend of peaceful country living and convenient proximity to Woodstock shops, restaurants, and schools.The main level features a light-filled, open-concept layout with a dramatic

Derek Cosentino Four Seasons Sotheby's Int'l Realty

339 Gully Rd, Woodstock, VT 05091

/31
Est $1,011,186 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,280 Sq Ft
10 Linden Hill, Woodstock, VT 05091

10 Linden Hill, Woodstock, VT 05091

/33
$1,900,000
- 2 Beds
- 2.5 Baths
- 2,944 Sq Ft
2394 Fletcher Hill Rd, Woodstock, VT 05091

Newly constructed Modern Vermont Farmhouse residence on 14 acres with absolutely amazing river views, 13-foot ceilings, gourmet kitchen, oversized french doors and windows throughout, radiant-heated concrete floors, first rate finishes, appliances and mechanicals located just 6 minutes to the Woodstock village green and 17 minutes to the Killington Skyeship base lodge. The first level is

John Snyder Snyder Donegan Real Estate Group

2394 Fletcher Hill Rd, Woodstock, VT 05091
/40
$2,425,000 Sold Aug 15, 2025
- 5,017 Sq Ft
- $483/SF
- 0 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2003
739 Westerdale Rd, Woodstock, VT 05091

Absolutely stunning, newly renovated residence, privately situated towards the end of a quiet town road in Woodstock, in an area of other substantial homes. Lovely mountain views and 10+ acres of privacy. The present owners have completed over $1 million in documented renovations in the past three years, including a fabulous new gourmet kitchen, powder bath, new bamboo flooring throughout the

John Snyder Snyder Donegan Real Estate Group

739 Westerdale Rd, Woodstock, VT 05091

/40
Est $1,641,034 Not Listed For Sale
- 6 Beds
- 6 Baths
- 3,892 Sq Ft
28 The Green Unit 30, Woodstock, VT 05091

28 The Green Unit 30, Woodstock, VT 05091

/40
$1,295,000
- 4 Beds
- 3 Baths
- 3,089 Sq Ft
16 Church St, Woodstock, VT 05091

16 Church has the most stunning view of the river from any house in the village that we have seen, perched up above a series of river rapids so the sounds of the river during the day or in the evening are incredibly peaceful and relaxing. Plus, 16 Church is privately nestled in, like a secret hideaway, yet steps to the village green (and a level walk to/from). And more unusual for the village,

John Snyder Snyder Donegan Real Estate Group

16 Church St, Woodstock, VT 05091
/55
$1,145,000 Sold Aug 15, 2025
- 2,710 Sq Ft
- $423/SF
- 5 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2020
2 Maple St, Woodstock, VT 05091

Located in the Heart of Woodstock Village- fantastic location at the foot of the Mtn Peg trail system with easy access to Vail field and all of towns amenities. This beautifully renovated home is completely new. Handsome farmhouse vernacular style home with traditional slate floors, sliding barn doors and wood floors throughout first floor with an open concept for entertaining and all new

Gretchjen Smith Williamson Group Sothebys Intl. Realty

2 Maple St, Woodstock, VT 05091

/40
Est $1,941,117 Not Listed For Sale
- 4 Beds
- 6 Baths
- 3,997 Sq Ft
2 Border Ln, Woodstock, VT 05091

2 Border Ln, Woodstock, VT 05091

/37
$1,185,000
- 4 Beds
- 3 Baths
- 2,785 Sq Ft
1782 Randall Rd, Woodstock, VT 05091

This early Woodstock residence was built in 1792 by Joseph Wood on a parcel of land he purchased in 1786 from Ebenezer Kingsley, one of Woodstock early settlers. A classic New England Cape of the period with the notable features of a central chimney with multiple fireplaces and a second story overhang on the gables. The house retains a great deal of original features and fabric including wide

Wade Treadway Wade I Treadway Real Estate

1782 Randall Rd, Woodstock, VT 05091
/26
$480,000 Sold Aug 15, 2025
- 930 Sq Ft
- $516/SF
- 98 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1860
11A Prospect St, Woodstock, VT 05091

Walk to everything Woodstock village has to offer from this sunny condo! Within an easy stroll of the Woodstock Inn, downtown restaurants, farmer's markets, and the Marsh Billings Rockefeller National Park, 11A Prospect is ideal for enjoying the charms of village living. Elevated above the Route 4 on a bucolic neighborhood side street, this well-kept home offers historic details with modern

Keri Cole Williamson Group Sothebys Intl. Realty

11A Prospect St, Woodstock, VT 05091

/40
Est $580,640 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,368 Sq Ft
1 Border Ln, Woodstock, VT 05091

1 Border Ln, Woodstock, VT 05091

/41
$1,495,000
- 4 Beds
- 2.5 Baths
- 2,532 Sq Ft
7 Slayton Terrace, Woodstock, VT 05091

A rare in-village offering, 7 Slayton Terrace combines walkability, views, and beautifully renovated interiors—just steps from the heart of Woodstock. Sited on an oversized .79-acre lot overlooking Billings Farm, this 4-bedroom home offers the space and flexibility rarely found so close to the village center. The main house features a stunning new kitchen with high-end finishes and beautifully

Keri Cole Williamson Group Sothebys Intl. Realty

7 Slayton Terrace, Woodstock, VT 05091
/44
$1,700,000 Sold Aug 15, 2025
- 2,423 Sq Ft
- $702/SF
- 177 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2007
2090 Randall Rd, Woodstock, VT 05091

Constructed in 2007 with a nod to the Gothic Style Vermont Farmhouse vernacular, this beautifully composed country home creatively integrates curated period detail with modern conveniences and systems. Conveniently located at the end of a picturesque tree lined dirt road just minutes from the Villages of both Woodstock and South Woodstock offering privacy and tranquility. The interior spaces of

Danny Kogut Williamson Group Sothebys Intl. Realty

2090 Randall Rd, Woodstock, VT 05091

/40
Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,733 Sq Ft
11 College Hill Rd, Woodstock, VT 05091

11 College Hill Rd, Woodstock, VT 05091

/59
$1,745,000
- 2 Beds
- 3 Baths
- 2,106 Sq Ft
7 North St, Woodstock, VT 05091

Stunning Renovated Antique Cape in the Heart of Woodstock Village!Tucked away on over an acre of beautifully landscaped land directly abutting the Marsh-Billings-Rockefeller National Park, this fully renovated antique Cape offers the rare combination of historic charm, modern efficiency, and unbeatable walkability. Located in the heart of Woodstock Village, you can stroll to the village

Keri Cole Williamson Group Sothebys Intl. Realty

7 North St, Woodstock, VT 05091
/36
$860,000 Sold Aug 11, 2025
- 2,330 Sq Ft
- $369/SF
- 367 Days On Market
- 4 Beds
- 1 Bath
- Built 1865
61 Putnam Rd, Bridgewater Corners, VT 05035

Enjoy a peaceful, park-like setting in the Broad Brook valley at one of Bridgewater’s most iconic farmhouses. Both floors of the home feature large rooms, high ceilings, and beautiful wide-board flooring. The main floor has a large eat-in kitchen with connected butler’s pantry/ mudroom, spacious formal dining room with views, living room, parlor, and a bedroom with a bath just outside the door.

Geoff Eckler Real Broker LLC

61 Putnam Rd, Bridgewater Corners, VT 05035

/39
Est $3,547,068 Not Listed For Sale
- 10 Beds
- 15 Baths
- 10,206 Sq Ft
3 Church St, Woodstock, VT 05091

3 Church St, Woodstock, VT 05091

/35
$1,895,000
- 5 Beds
- 4.5 Baths
- 4,214 Sq Ft
10 College Hill Rd, Woodstock, VT 05091

10 College Hill is the perfect in-village residence, off the main road yet walk-to-everything. The original, historic residence was designed in 1916 by renowned architect John Russell Pope whose accomplishments include the Jefferson Memorial, and master plans for Dartmouth and Yale. It also enjoys modern additions and updates including a stunning first-level primary bedroom suite designed in

John Snyder Snyder Donegan Real Estate Group

10 College Hill Rd, Woodstock, VT 05091
/52
$545,000 Sold Aug 06, 2025
- 2,240 Sq Ft
- $243/SF
- 53 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1944
1613 W Woodstock Rd, Woodstock, VT 05091

OPEN HOUSE SUNDAY JUNE 15 FROM 12-3! Welcome to this turn-key, thoughtfully renovated home featuring a fully updated kitchen with granite countertops, stainless steel appliances, a gas stove, and a sliding glass door that opens to a covered porch—perfect for overlooking the spacious backyard. The main level offers a comfortable bedroom and a nearby full bath, while upstairs you'll find two

Holly Hall Hall Collins Real Estate Group

1613 W Woodstock Rd, Woodstock, VT 05091

/40
Est $1,406,164 Not Listed For Sale
- 6 Beds
- 4 Baths
- 3,719 Sq Ft
26 River St, Woodstock, VT 05091

26 River St, Woodstock, VT 05091

/49
$810,000
- 3 Beds
- 2 Baths
- 1,660 Sq Ft
37 South St, Woodstock, VT 05091

Welcome to this beautifully renovated residence in the vibrant heart of Woodstock Village. Enjoy unparalleled convenience with a short stroll to the Elementary School, Woodstock Inn, the picturesque Green, and an array of charming shops, restaurants, and bakeries that define village living. Nestled directly across from Vail Field, this home offers easy access to playgrounds, ball fields, and

Mark Roden KW Coastal and Lakes & Mountains Realty/Hanover

37 South St, Woodstock, VT 05091
/34
$679,000 Sold Aug 04, 2025
- 2,128 Sq Ft
- $319/SF
- 49 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1968
294 Barberry Hill Rd, Woodstock, VT 05091

Discover this delightful 3-bedroom, 2.5-bath home nestled on 1.8 acres at the end of a peaceful dead-end road. Conveniently located near Woodstock Middle/High School, the Thompson Senior Center, and the popular Woodstock Farmers’ Market.This home offers a spacious and functional layout, the welcoming mudroom features generous storage space and a laundry area cleverly tucked behind sliding

Bonnie Bergeron Snyder Donegan Real Estate Group

294 Barberry Hill Rd, Woodstock, VT 05091

/29
Est $658,927 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,280 Sq Ft
42 River St, Woodstock, VT 05091

42 River St, Woodstock, VT 05091

Showing Results 1 - 40, Page 1 of 18

Vermont Windsor County Brownsville

How to Buy a Home How to Finance a Home How to Sell a Home

Find More Real Estate & Homes for Sale by State

Top Cities with Homes For Sale

Top Counties with Homes For Sale

More Real Estate For Sale Near Me

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2025 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage