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Beautiful Brookline! Lovingly developed by the current owners over the past 40 years, this remarkable property offers a rare opportunity-ideal for a builder, contractor, skier, snowmobiler, or anyone seeking space for equipment storage. Arrive by crossing a charming stream and following a gentle rise to the main home, which includes a one-car attached garage in the basement. Inside, the finished lower level features a comfortable sitting/TV room, laundry area, large storage closet, and utility room. Upstairs, the first floor opens into a warm, open-concept kitchen, dining, and living space centered around a striking wood-burning fireplace with a glass door enclosure. To the south, a spacious three-season sunroom invites relaxation in every season. The primary bedroom, with an en-suite bath, is conveniently located on this level. A great office space is here, too. The upper floor features two spacious bedrooms, each equipped with ample storage space. Outdoors, the property shines: a large trout pond graces the north side of the home, while the land abuts the Windmill Hill Pinnacle Association, offering direct access to miles of scenic hiking trails. Snowmobile enthusiasts will also appreciate nearby trail access. A separate three-car garage expands the possibilities-imagine a future guest house, in-law suite, or artist studio! This unique Brookline property must be experienced in person to be fully appreciated.

More Info

Tax Information

  • Tax Year2025

Location

  • Building Number1382
  • StreetGrassy Brook Road
  • TownBrookline
  • StateVT
  • Zip05345
  • CountyWindham
  • DistrictWindham Southeast
  • Elementary SchoolNewbrook Elementary School
  • Junior HighLeland Gray Union Middle/High
  • High SchoolLeland Gray
  • Flood Zone Y/NNo
  • Address1382 Grassy Brook Road

Interior

  • Interior FeaturesDining Area, Wood Fireplace, Kitchen Island, Kitchen/Dining, Kitchen/Living, Living/Dining, Primary BR w/ BA, Natural Light, Security, Indoor Storage, Surround Sound Wiring, Walk-in Pantry, Common Heating/Cooling, Basement Laundry
  • Room 1 TypeKitchen/Living
  • Room 1 Level1
  • Room 1 Dimensions27X20
  • FloorsCarpet, Hardwood, Softwood
  • Stories1.5
  • Room 6 TypeSunroom
  • Room 6 Level1
  • Room 6 Dimensions14.10X13.3
  • Room 7 TypeOffice/Study
  • Room 7 Level1
  • Room 7 Dimensions10.10X8.5
  • Room 10 TypeBedroom with Bath
  • Room 10 Level1
  • Room 10 Dimensions15X13.3
  • Room 11 TypeBedroom
  • Room 11 Level2
  • Room 11 Dimensions21.3x14.9
  • Room 12 TypeBedroom
  • Room 12 Level2
  • Room 12 Dimensions21.3x13.1
  • Room 16 TypeBathroom Full
  • Room 16 Level1
  • Room 16 Dimensions8X5
  • Room 17 TypeBathroom Three Quarter
  • Room 17 Level1
  • Room 17 Dimensions8.4X6.3
  • Room 18 TypeBathroom Half
  • Room 18 LevelBasement
  • Room 18 Dimensions6x6

Parking

  • Parking Spaces3
  • GarageYes
  • Parking DescriptionAuto Open, Direct Entry, Finished, Heated Garage, Storage Above, Driveway, Garage, Off Street, On-Site, Parking Spaces 11 - 20, Detached

Building

  • Year Built1985
  • Building ConstructionClapboard Exterior
  • ConstructionExisting
  • Property StyleContemporary
  • Bedrooms3
  • Bathroom3
  • Total Baths3
  • 3/4 Baths1
  • Half Bath1
  • Total Rooms6
  • Square Feet3,113
  • BasementClimate Controlled, Concrete, Concrete Floor, Daylight, Finished, Insulated, Interior Stairs, Locked Storage, Walkout, Interior Access, Basement Stairs
  • FoundationPoured Concrete

Exterior

  • Exterior FeaturesDeck, Shed, Window Screens, Double Pane Window(s)
  • Exterior ColorBrown
  • RoofMetal, Asphalt Shingle

Amenities

  • AmenitiesCO Detector, Security System, Smoke Detector, Standby Generator
  • PricePerSqFt205.27

Other

  • Delayed ShowingsYes
  • Date Showings Begin2025-09-27
  • SeasonalNo
  • Foot Print Dim38X37
  • Page241-3
  • Date Listed09/22/2025

Rooms

  • Full Bath1

Basic Information

  • MLS Number5062413
  • MLS StatusActive
  • Virtual TourView Tour
  • StatusACT
  • Property TypeSingle Family
  • List Price$639,000
  • Listing Agent NameThom Dahlin
  • Broker NameBerkley & Veller Greenwood Country

Property

  • Acreage44.3
  • Lot DescriptionCountry Setting, Landscaped, Mountain View, Open, Pond, Pond Site, Rolling, Secluded, Stream, Timber, Walking Trails, Wooded, Abuts Conservation, Mountain, Near Skiing, Near Hospital
  • AreaVT-Windham
  • DrivewayCircular, Crushed Stone
  • RoadsUnpaved, Public Maintained Road
  • Road Frontage355

Utilities

  • Heat SystemOil, Forced Air, Hot Air, In Floor
  • WaterDrilled Well
  • SewerLeach Field at Grade, Leach Field On-Site, On-Site Septic Exists, Private
  • ElectricCircuit Breaker(s), Generator
  • UtilitiesCable at Site, Propane, Telephone at Site

Map Location

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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. Data last updated November 15, 2025 10:23 PM EST

 

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