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49 Windsor Dr 301Holliston, MA 01746

For Sale

$299,000

Smart Buyer Rebate - Ask

Welcome to Oakridge Condominiums! This spacious top-floor 2-bedroom unit an open floor plan and a gorgeous view in a peaceful setting at the end of a wooded cul-de-sac. Located in a garden-style building, this home offers comfortable, low-maintenance living. The building features on-site laundry, secure storage assigned to each unit, one assigned parking space, and ample guest parking. Enjoy a prime location just minutes from the commuter rail, grocery stores, shopping, parks, and the Charles River Rail Trail. For those seeking convenient, low-maintenance living, this condo is a great choice. With limited options at this price point, it is an excellent opportunity for a homeowner or investor.

Listed by Melissa Kaspern

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REMAX Executive Realty

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5083334670

Last updated October 18, 2026

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Source: MLSPin #73576026

Listing Facts

  • TypeCondo
  • NeighborhoodHolliston
  • Bedrooms2
  • Bathrooms1
  • Days on Prevu50
  • HOA/Maint. Fees$349.34/month
  • Taxes$2,575/year
  • Size883 sqft
  • Price per sqft$339

Amenities

  • Parking

Location

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Listing History

10/02/2026
Price Decreased
$299,000
09/11/2026
Listed by REMAX Executive Realty
$309,000
  1. 10/02/2026$299,000
    Price Decreased
  2. 09/11/2026$309,000
    Listed by REMAX Executive Realty

Property Details for 49 Windsor Dr 301

Association

Amenities

  • Association Amenities: Hot Water
  • Community Features: Tennis Court(s), Park
  • Pets Allowed: No

Fees

  • Association Fee: $349.34 Monthly
  • Association Fee Includes: Water, Sewer, Insurance, Maintenance Structure, Maintenance Grounds, Snow Removal, Trash

Exterior

Construction

  • Number Of Units Total: 30
  • Stories: 1
  • Stories Total: 1
  • Year Built: 1970
  • Year Built Details: Actual
  • Building Name: Oakridge
  • Construction Materials: Brick
  • Entry Level: 3
  • Entry Location: Unit Placement(Upper)

Measurements

  • Building Area Total: 883
  • Building Area Units: Square Feet
  • Lot Size Units: Acres

Financial

Taxes

  • Parcel Number: M:011 B:0006 L:010U,526507
  • Tax Annual Amount: $2,575.00
  • Tax Assessed Value: $175,800.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Range, Refrigerator
  • Flooring: Vinyl, Carpet
  • Interior Features: High Speed Internet, Master Downstairs, Open Floorplan

Measurements

  • Living Area: 883
  • Living Area Source: Public Records

Rooms

  • Bathrooms Full: 1
  • Bathrooms Total Integer: 1
  • Bedrooms Total: 2
  • Rooms Total: 4

Parking

Parking

  • Open Parking Spaces: 1
  • Parking Features: Off Street, Common, Guest
  • Parking Total: 1

Schools

Elementary School

  • Elementary School: Placentino

High School

  • High School: Holliston Hs

Middle or Junior School

  • Middle Or Junior School: Robert Adams Ms

Utilities

Equipment

  • Cooling: Wall Unit(s)
  • Has Cooling: Yes
  • Heating: Electric
  • Has Heating: Yes
  • Laundry Features: Common Area
  • Sewer: Private Sewer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this condo have?

There are 2 bedrooms and 1 bathroom in this condo at 49 Windsor Dr 301.

What schools are nearby to 49 Windsor Dr 301?

Nearby schools include the Placentino Elementary School, Robert Adams Ms Middle School, and Holliston Hs High School.

Does this condo have parking?

Yes, there is 1 parking space available for 49 Windsor Dr 301.

What are the annual taxes for 49 Windsor Dr 301?

Annual taxes for this condo are estimated at $2,575.

How does 49 Windsor Dr 301 compare to other condos in Holliston?

This condo is listed 63% below the average price for condos in Holliston and has been on the market for 41 less days than the typical home in this area.

What building or home owners association is the condo part of?

This condo is in the Oakridge building.

What is the square footage on this condo?

According to the MLS, this listing is 883 sqft.

49 Windsor Dr 301 is a 2-bedroom, 1-bath condo for sale in Holliston MA 01746. Available on Prevu for 50 days at $299,000. This includes a recent price decrease of $10,000. This home features 883 square feet of living space, located in Holliston. The median listing price for condos in this area is $799,900. Nearby schools include Placentino Elementary School, Robert Adams Ms Middle School, and Holliston Hs High School. The home offers parking. Browse more condo listings in Middlesex County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.