# 27 Headlands Road, Winchester, NH 03470

> **TL;DR:** 2bd/2ba single family, $725,000 ($537/sqft), built 1992, 1,351 sqft.
> Basement. Est. $3,142/mo. Listed 304 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $725,000 |
| Price/sqft | $537 |
| Bedrooms | 2 |
| Bathrooms | 1 full, 1 half |
| Square Feet | 1,351 |
| Year Built | 1992 |
| Lot Size | 6,970 sqft (0.16 acres) |
| Stories | 2 |
| Property Type | Single Family (Single Family Residence) |
| Status | For Sale |
| Days on Market | 304 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $3,142 |
| **Total** | **$3,142** |

## Nearby Schools

- **Elementary:** Winchester School

## Key Amenities

- Basement

## Property Highlights

- Built in 1992
- 0.16 acre lot
- 1.5 stories

## Description

### Agent 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.

## Location

- **Address:** 27 Headlands Road, Winchester, NH 03470
- **County:** Cheshire
- **Coordinates:** 42.788609, -72.362355
- **Google Maps:** https://www.google.com/maps?q=42.788609,-72.362355

## Listing Agent

- **Name:** Vincent Dolan
- **Brokerage:** RE/MAX Town & Country
- **Phone:** 6033574100
- **Email:** vince@vincedolan.com

## Primary Photo

![27 Headlands Road - Primary Photo](http://lh.rdcpix.com/aa97c15d927abf7a0b24d00565a5ed7al-f2872556282r.jpg)

*36 total photos available on [listing page](https://www.propertysimple.com/listing/27-headlands-road-winchester-nh-03470-5045812)*

---

**MLS#:** 5045812 | **Updated:** 2026-04-24
**Source:** listhub

*Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.com/listing/27-headlands-road-winchester-nh-03470-5045812)

---

## Structured Data

```json
{
  "@context": "https://schema.org",
  "@type": "RealEstateListing",
  "name": "27 Headlands Road, Winchester, NH 03470",
  "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.",
  "url": "https://www.propertysimple.com/listing/27-headlands-road-winchester-nh-03470-5045812",
  "image": "http://lh.rdcpix.com/aa97c15d927abf7a0b24d00565a5ed7al-f2872556282r.jpg",
  "datePosted": "2026-04-24",
  "price": 725000,
  "priceCurrency": "USD",
  "address": {
    "@type": "PostalAddress",
    "streetAddress": "27 Headlands Road",
    "addressLocality": "Winchester",
    "addressRegion": "NH",
    "postalCode": "03470",
    "addressCountry": "US"
  },
  "geo": {
    "@type": "GeoCoordinates",
    "latitude": 42.788609,
    "longitude": -72.362355
  },
  "numberOfRooms": 2,
  "numberOfBathroomsTotal": 2,
  "floorSize": {
    "@type": "QuantitativeValue",
    "value": 1351,
    "unitCode": "FTK"
  },
  "yearBuilt": 1992
}
```