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Windsor Vermont Real Estate

Windsor County
Chartered: July 6, 1761
Area: 12,650 Acres = 19.77 Square Miles
Population (US Census, 2000): 3,756
Population Density (persons per square mile): 190

Schools

Windsor Southeast Supervisory Union 802-674-2144
Windsor High School 802-674-6344
Windsor State Street School 802-674-2310

Windsor Vermont is located on the eastern side of the state, right on the border of New Hampshire. Bromley Mountain Resort is just the next town over in Brownsville, Vermont. This Southern Vermont town enjoys the company of the Connecticut River, which winds through the town and the village area. Windsor is the “Birthplace of Vermont,” and the Old Constitution House, where the constitution of the “Free and Independent Republic of Vermont” was drafted, still stands today. Windsor Vermont real estate has Vermont’s best ski resort recreation just a drive away. In an hour or less one can ski or snowboard Ascutney Mountain Resort, Suicide Six Ski Area, Killington Resort, Pico Ski Resort, Okemo Mountain Resort, Magic Mountain Ski Resort, and Stratton Mountain Ski Resort.

Windsor Regional Chamber of Commerce

3223 County Road Windsor VT 05089

Windsor, VT3223 County Road

Price$879,900

Est. Mortgage: $/month

MLS Number 5001343

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

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: 6.77% last updated on Jul 18, 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.

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1185 Route 5 South Windsor VT 05089

Windsor, VT1185 Route 5 South

Price$625,000

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: 6.77% last updated on Jul 18, 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.

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25 Main Street Windsor VT 05089

Windsor, VT25 Main Street

Price$550,000

Est. Mortgage: $/month

MLS Number 4998054

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 4
  • Bathroom 2

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: 6.77% last updated on Jul 18, 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.

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39 Huntington Drive Windsor VT 05089

Windsor, VT39 Huntington Drive

Price$399,900

Est. Mortgage: $/month

MLS Number 4999516

  • Residential Single Family
  • Full Bath 1
  • Construction Existing
  • Bedrooms 3
  • Bathroom 1

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 23, 10-12noon

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 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.

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2326 Route 5 N Windsor VT 05089

MLS Number 5003219

  • Commercial
  • Year Built 1900
  • Square Feet 3,427
  • Acreage 0.81
  • PricePerSqFt 116.43

This long standing Windsor staple has been the local Vet and Pet Dental for many, many years. Retirement looms for these owners, lending a vast opportunity for someone new. Consider having a wonderful commercial space complete with offices or exam rooms, plenty of parking, waiting areas, several entrances, and updated systems: roof, electrical, siding, heating, etc.. Further, you have 3 tenants paying the majority of the mortgage before even utilizing the main level for further investment or rental. Call today to discuss the endless possibilities.

Listed by Katie Ladue Gilbert of KW Vermont Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 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.

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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: 6.77% last updated on Jul 18, 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.

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69 Morningside Drive Windsor VT 05089

Windsor, VT69 Morningside Drive

Price$310,000

Est. Mortgage: $/month

MLS Number 5005220

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 3
  • Bathroom 2

Now is your opportunity to own this renovated, well-cared-for 3-bedroom, 2-bathroom home on a spacious 1+ acre lot in a desirable cul-de-sac neighborhood. This home provides a split master bedroom from its secondary bedrooms, an open floor plan, and a secluded back patio to enjoy pleasant Vermont evenings outside. Renovations include - new vanities, appliances, toilets, and flooring, as well as fresh paint throughout. It also provides a large, unfinished basement, a blank canvas for your imagination, that can be used for storage or finished for even more square footage. This home is conveniently located minutes from shopping, dining, grocery, John P. Larkin Country Club/Golf Course, and Mt. Ascutney Hospital, to name a few. Don't let this one pass you by. Schedule your private tour today!

Listed by Tara Reeves of Vermont Real Estate Company

$
$
%
$/month over payments
Federal 30-year interest rate: 6.77% last updated on Jul 18, 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.

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12-14 State Street Windsor VT 05089

Windsor, VT12-14 State Street

Price$275,000

Est. Mortgage: $/month

Pending

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: 6.77% last updated on Jul 18, 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.

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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: 6.77% last updated on Jul 18, 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

Pending

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: 6.77% last updated on Jul 18, 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 July 24, 2024 7:38 AM EDT