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27 Headlands Road, Winchester, NH

Single Family Residence

For SaleActive
2 Beds|2 Baths|973 ft²|Built 1992|Winchester

Listed by RE/MAX Town & Country · Vincent Dolan

Property Description

Stunning Waterfront! Like new Cape style post and beam beauty with direct waterfront on Forest Lake. Gorgeous views from every window. Modern Kitchen with stainless appliances and center island. Cozy Living Room with gas Fireplace. The downstairs living area contains a Family Room, Kitchen, Bedroom and Bathroom. This is a perfect year-round retreat or possible short term rental. Also being offered as part of a portfolio of short-term rental properties.

Property Details

Essentials & finishes

  • Bedrooms:2
  • Total Baths:2
  • Full Baths:1
  • SqFt:973
  • Price / SqFt:$739.98
  • Property Type:Single Family Residence
  • Year Built:1992
  • County:NH-Cheshire
  • Town:Winchester, NH
  • Status:Active
  • Days on Market:398

Primary Features

CountyNH-Cheshire
Property TypeResidential
Year Built1992
ZoningForest Lake District

Interior Features

AppliancesDishwasher, Microwave, Mini Fridge, Gas Range, Refrigerator
BasementYes
Basement Access TypeInterior
Basement DescriptionFinished, Interior Stairs, Walkout
1/4 Baths0
3/4 Baths0
CoolingMini Split
Electric100 Amp Service, Circuit Breakers
FlooringCarpet, Softwood, Vinyl
HeatingBaseboard
Interior FeaturesCathedral Ceiling(s), Gas Fireplace, Kitchen Island
Rooms - Total7
SqFt-Approximate Finished Above Grade973
SqFt-Approximate Finished Below Grade378
SqFt Approximate Total Finished1,351
SqFt Approximate Total1,471

Location Information

School - DistrictWinchester
School - ElementaryWinchester School

Financial Details

Foreclosed / Bank-Owned / REONo
Tax - Gross Amount$9,340
Tax Year2023
Taxes TBDNo

Additional

Construction StatusExisting
ConstructionPost and Beam, Wood Frame
CovenantsUnknown
Flood ZoneNo
Pre-ConstructionNo
Property Sub TypeSingle Family Residence
SeasonalNo
Total StoriesOne and One Half
SurveyedUnknown
Timeshare/Fractional OwnershipNo

External Features

DrivewayGravel
Exterior FeaturesBoat Mooring, Dock, Deck, Shed
FoundationConcrete, Poured Concrete
GarageNo
Lot FeaturesLake Frontage, Lake View, Sloping, Waterfront
Lot - Acres0.16
Lot - SqFt6,970
ParkingParking Spaces 4
Road Frontage TypePublic Maintained Road
Road FrontageYes
Road Frontage Length71
RoofArchitectural Shingle
SewerLeach Field On-Site, Private Sewer, Septic Tank
UtilitiesCable Available, Propane, Underground Gas
Water SourcePublic
Water Body TypeLake
MLS®: PrimeMLS #5045812; Listed by RE/MAX Town & Country · Vincent Dolan

Property History

Annual taxes for this property

YearAssessed Tax
2024$12,240
2023$11,934
2022$11,628

Estimated from list price; verify with the town assessor.

Market Data

Live snapshot computed from active listings in this town

  • Active listings in Winchester26
  • Average list price$282,825
  • Price range$19,500 – $675,000
  • Market sentimentBuyer's Market

Mortgage Calculator

Estimate your monthly payment for this home

20%
Loan Term
6.5%
Estimated monthly payment$4,811 / mo
  • Principal & Interest$3,641
  • Property Tax$1,020
  • Home Insurance$150

Estimates use typical New Hampshire costs — a 1.7% effective property-tax rate, insurance at 0.25% of home value/yr, and PMI below 20% down. Actual town tax rates vary; verify with your lender and the town assessor.

$720,000/ Asking Price
For SaleActive
Est. $3,641 / mo20% down · 30yr · 6.5%
Tom DeMatteo

Tom DeMatteo

Owl’s Nest Real Estate · Questions?

401-648-5308

Market Sentiment

Buyer's Market
Buyer’s MarketBalancedSeller’s Market

Based on 26 active · 0 sold in Winchester (last 90 days)

PrimeMLS

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Owl's Nest Real Estate

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site 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. This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information. The listing broker's offer of compensation is made only to other real estate licensees who are participant members of the PrimeMLS.

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