Windsor Vermont Real Estate

Are you thinking of buying a home in Windsor Vermont?  Scroll down to view listings that are currently on the market and contact me if you would like more details on specific properties.  You can also create an account with my site to save your favorite Vermont real estate listings.

3223 County Road Windsor VT 05089

Windsor, VT3223 County Road

Price$879,900

Est. Mortgage: $/month

MLS Number 5001343

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,238

Welcome to this exquisite four-bedroom, two-bathroom Colonial home, built in 1801, nestled on a sprawling 10.4-acre lot in Windsor, Vermont. This charming residence boasts maple and bamboo floors as well as original wide pine flooring, spacious bedrooms, and tiled bathrooms. The property includes a two-bedroom, one-bathroom ADU, perfect for generating rental income or accommodating guests. Enjoy the serene rural setting with level land ideal for animals, fenced pastures, and extensive perennial gardens. Outdoor amenities include a glamping site over the barn, RV hookups, an in-ground pool, and a tranquil majestic pond surround by natural iris that bloom every spring. Recent updates blend historic charm with modern appointments, maintaining the home beautifully for 30 years under the same owner. Located close to local amenities, this home offers both seclusion and convenience. Additional features include outbuildings and an animal barn, providing ample storage and versatile use. Don't miss this unique opportunity to own a piece of Vermont history with endless potential.

Listed by Kate Cassidy of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

1185 Route 5 South Windsor VT 05089

Windsor, VT1185 Route 5 South

Price$675,000

Est. Mortgage: $/month

MLS Number 4990468

  • Multifamily
  • Units 8
  • Acreage 1.44
  • Square Feet 2,768
  • Utilities None

Introducing a prime investment opportunity nestled on 1.44 acres of picturesque countryside just moments away from the convenience of town living. Whether you're a seasoned investor seeking a lucrative addition to your portfolio or a newcomer to the world of real estate investment, this 8-unit property presents an attractive proposition. With its idyllic location, modern updates, and reliable tenant base, it offers the perfect combination of rural charm and urban convenience-a truly rare find in today's market. Don't miss your chance to own a piece of country paradise with endless potential for growth and prosperity.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

25 Main Street Windsor VT 05089

Windsor, VT25 Main Street

Price$550,000

Est. Mortgage: $/month

MLS Number 4998054

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 3,146

Built in 1796, the historic Trask House is located on beautiful Main St. in the heart of downtown Windsor. The center hall Federal sits on just under 1/2 acre and has an attached barn/garage in the back with plenty of storage. There is a private brick patio surrounded by a white picket fence and lovely landscaping. Inside, you are greeted by large open rooms with hardwood floors, high ceilings, and multiple fireplaces. The updated kitchen is open to the dining room with a wood burning stove centered between the two rooms. The dining room leads to the stunning living room with picturesque alcoves and original Federal style millwork and mantels. Across the hall are the family room and a quaint library which ultimately connects back to the kitchen. A grand center hall stair case leads upstairs to 4 good sized bedrooms, a full bath and the laundry room. The Trask House is in an ideal location just minutes from Lake Runnemede, restaurants and stores, and Mt. Ascutney Hospital. Woodstock, Hanover, and the Upper Valley are approximately 25 minutes away. The Trask House is in the National Registry of Historic Homes and has been featured in numerous books on historic homes of New England. Come take a look!

Listed by Dan Noble of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

4 Old Mill Pond Road Windsor VT 05089

MLS Number 5000223

  • Condo
  • Square Feet 2,052
  • Bedrooms 3
  • New Contruction Existing
  • Complex Old Mill Pond

Old Mill Pond Condominiums offer an idyllic haven in the heart of Windsor. Imagine enjoying mountain views, pond access, and amenities such as an in-ground pool and tennis courts. This unit features vaulted ceilings and unique architectural elements often missing in typical condominiums. Guests can relax by the cozy fireplace or on the spacious deck with mountain views, depending on the season. Year-round convenience is assured with an attached garage, ample storage, and a functional layout. The unit includes three bedrooms, each with an ensuite bath-one of which includes a delightful jacuzzi tub. Includes an additional inviting 4th sleeping space to accommodate your guests. For those seeking easy living, this move-in ready unit within an impeccably maintained condo association is hard to beat! **delayed showings until Open House Sunday June 16th, 2024**

Listed by Julie Davis of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

39 Huntington Drive Windsor VT 05089

Windsor, VT39 Huntington Drive

Price$399,900

Est. Mortgage: $/month

MLS Number 4999516

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1
  • Square Feet 2,160

Welcome to this well-maintained ranch located in the highly sought-after Juniper Terrace neighborhood. This delightful home features 3 cozy bedrooms and 1 full bath, perfect for comfortable living. The inviting living area is complemented by a pellet stove, providing warmth and ambiance during the cooler months. The highlight of this home is the finished basement, offering additional living space that can be customized to suit your needs-be it a family room, home office, or recreation area. The exterior is equally impressive with a well-manicured lawn and charming curb appeal. Don't miss the opportunity to make this lovely home yours. Schedule a showing today and experience the best of Juniper Terrace living! Open House Sunday June 9, 10-12noon

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

12-14 State Street Windsor VT 05089

Windsor, VT12-14 State Street

Price$275,000

Est. Mortgage: $/month

MLS Number 4999035

  • Multifamily
  • Units 4
  • Acreage 0.03
  • Square Feet 2,430
  • PricePerSqFt 113.17

Rare Opportunity in the heart of Windsor, Vermont. This building contains 3 residential rental units and 1 additional unit that has been used as office space but can be converted into an additional residential unit with a permit. This originally balloon built property has had its foundation restabilized, new insulation, and almost 100% siding replaced. The first floor contains the office rental, Unit 1, Unit 2 access, and a common area/mailroom. Unit 1 contains a mudroom, kitchen/living room, bedroom, and bathroom. Unit 2, on the second floor, contains a kitchen, living room, bathroom, and two bedrooms. Unit 2 has high ceilings making the space feel open and spacious, with upgraded electrical throughout most of the building. Unit 3 is accessed by covered outdoor stairs to the third floor. This unit contains a small mudroom, kitchen/dining room, bathroom, and two bedrooms. Office space is currently an open office room with a private bathroom. Basement is dry and spacious, plenty of space for storage and/or laundry room. Seller has Lead Paint Certification. The location is right downtown! Café across the street and walking distance to shops, parking, laundry mat, school, and public transportation. Delayed showings until Thursday June 13th!

Listed by Cheryl Herrmann and Kelsey Herrmann-Satnzel of RE/MAX Group One Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

119 Ascutney Street Windsor VT 05089

Windsor, VT119 Ascutney Street

Price$275,000

Est. Mortgage: $/month

MLS Number 5000569

  • Residential Single Family
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,554

OPEN HOUSE Saturday, June 15th 10-12 PM! Nestled on the edge of Windsor Village, this charming cape-style home has a well-maintained allure and picturesque appeal, inviting new homeowners to make it their own. A cobblestone chimney accents the exterior and a welcoming split rail fence adds to its quaint charm. Many new upgrades and features include a circular driveway, all new vinyl siding, new windows, and a private back patio deck. The driveway offers easy access to pull in & out, and ample parking space as well. The mudroom seamlessly connects to the kitchen, convenient for unloading your groceries, and unwind in the spacious and open concept living/dining room filled with natural light through large bay windows. Enjoy hardwood floors throughout and a classic stone fireplace could be revived for cozy evenings by the fire. The functional eat-in kitchen offers extra counter space, while a bonus room provides versatility as a den or office area. A front and back staircase ascend to four large bedrooms on the second floor, ensuring plenty of space for everyone. Outside, a large flat yard invites creativity, perfect for creating your ideal outdoor oasis, whether it's building a firepit for gatherings, playing or gardening. Walk to school, the Windsor Swim Area at Mill Pond, or explore the Windsor Fairgrounds and Paradise Park. With a short commute to Hanover, Lebanon, DHMC, and Dartmouth College, this move-in ready home offers great accessibility in one desirable package.

Listed by Tyler Hall of BHHS Verani Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

141 Ascutney Street Windsor VT 05089

Windsor, VT141 Ascutney Street

Price$224,900

Est. Mortgage: $/month

Pending

MLS Number 4999012

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 1
  • Square Feet 696

Recent updates include new wiring, standing seam roof, plumbing, hot water heater, kitchen cabinets & countertops and flooring, landscaped grounds with a huge array of flowers plus blueberries, raspberries and plum tree. Walk to town, tennis, basketball courts and kennedy's pond.

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

9 Durkee Street Windsor VT 05089

Windsor, VT9 Durkee Street

Price$199,900

Est. Mortgage: $/month

MLS Number 4995534

  • Multifamily
  • Units 11
  • Acreage 0.09
  • Square Feet 3,500
  • Utilities Other

Let this rooming house be your next great investment. 10 rooms, and a 2 bedroom apartment. Some long term renters. Rooms still available, and new boiler just installed.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

9 Durkee Street Windsor VT 05089

Windsor, VT9 Durkee Street

Price$199,900

Est. Mortgage: $/month

MLS Number 4995187

  • Residential Single Family
  • Construction Existing
  • Bedrooms 12
  • Bathroom 3
  • Square Feet 3,500

Let this rooming house be your next great investment. 10 rooms, and a 2 bedroom apartment. Some long term renters. Rooms still available, and new boiler just installed.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

70-74 State Street Windsor VT 05089

Windsor, VT70-74 State Street

Price$195,000

Est. Mortgage: $/month

MLS Number 4953869

  • Residential Single Family
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4
  • Square Feet 4,011

The Stephen Jacob House is an extremely important historic residence in a town known for its historic architecture. Built in 1784 in the Georgian/Federal style, the residence was sited on the rise of State Street from the Village of Windsor. It's commanding presence was embellished with cornice dentil detailing and possibly a Palladian window. Having been used for many purposes over the years, the house was purchased by Historic Windsor, Inc. in 2008. Recognizing its historic significance along with much original fabric intact, Historic Windsor, Inc. engaged in a massive cleanup, extensive documentation and a complete paint job with some sections reroofed with standing seam. The residence is now ready for the next phase of its life as a single family residence, up to 4 residential apartments, owner occupied business or a cultural center. All of the necessary as built architectural plans, documentation of existing materials and fabric and proposed Feasibility Plans are available. The project will require all new systems and rehab working with the extensive original fabric including interior shutters, period flooring and window and door detailing. Many original doors. The residences rich history with Stephen Jacob and its architectural significance will regain its prominence in Historic Windsor upon completion.

Listed by Wade Treadway of Wade I Treadway Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

149 Main Street Windsor VT 05089

Windsor, VT149 Main Street

Price$157,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4986683

  • Residential Single Family
  • Construction Existing
  • Bedrooms 2
  • Bathroom 3
  • Square Feet 2,009

Behind the gated picket fence, is a 1795 dwelling waiting to be restored to its former beauty. Beautiful wooden beams and wood floors. Upon entering the dwelling, there is a good sized living room on the left, and bedroom to the right. There are rooms in the back of the first floor [including a ½ bath] which potentially could be converted a den or into a large kitchen with a dining area which would overlook the back deck, lawn and plantings. The second floor includes a kitchen, one bedroom, and a full bath with a tub. The lower level includes closet/storage space, two large rooms which could be completely finished for a family room, a playroom, or for additional storage. Walking out of the lower level, takes you onto a good-sized deck for relaxing, and outdoor dining. At the far back of the lawn, which also has plantings, is the garage which has room for a small workshop. The property is walking distance to restaurants, shops and banks and a short distance to a shopping center. License To Sell in place. If you are thinking of home ownership, appreciate older homes, with character and charm, consider this opportunity.

Listed by Amy Messina of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

338 Us Route 5 South Windsor VT 05089

Windsor, VT338 Us Route 5 South

Price$125,000

Est. Mortgage: $/month

MLS Number 4992919

  • Residential Single Family
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,504

Spacious and affordable 3-story dwelling in desirable Windsor. Buy it as a starter home, or take the opportunity for renovation and rental or resale. Pleasant stone landscaping in the yard. A kitchenette is found in the 3rd floor apartment (perhaps a rental unit or an in-law suite?) There's proximity to shopping (including a fine glass store, brewery, distillery, and jam shop), Amtrak, Mount Ascutney Hospital, and across the street from the Connecticut River!

Listed by Zachary Zupan of EXP Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

153 Main Street Windsor VT 05089

Windsor, VT153 Main Street

Price$99,900

Est. Mortgage: $/month

MLS Number 4998415

  • Multifamily
  • Units 3
  • Bathroom 3
  • Acreage 0.14
  • Square Feet 1,800

As-Is Sale Only. Updated interior pics added.

Listed by Robert Balewicz of Evergreen Realty of Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

2781 Us Route 5 N Windsor VT 05089

MLS Number 4985204

  • CommercialLease
  • Lease 3500
  • Square Feet 2,450
  • Year Built 1997
  • Acreage 0.48

This Former McDonald's Restaurant is a Great Property for your Business. Situated Adjacent to a Plaza with Price Chopper, Aubuchon Hardware and Dollar General and Sited on Busy US Rte 5 only Minutes from Historic Windsor Means You Have Many Free Benefits. Being Well Maintained and with a Drive Thru Window, 14 Ft Ansul System Range Hood, Open Concept, and 2 ADA Rest Rooms Equates to an "Easy to Start Your Operations Property". Close to I-91 Access, Ski Areas, Golf Course, and Local Hospital and 20 Minutes to Hanover/Lebanon and Extra Benefits So Don't Wait on thie Unique Opportunity.

Listed by Brian Whipple of Coldwell Banker Homes Unlimited

$
$
%
$/month over payments
Federal 30-year interest rate: 6.95% last updated on Jun 13, 2024
* 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

Broker Reciprocity 

Copyright 2024 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 19, 2024 9:40 PM EDT