10

Winchester, NH Homes for Sale with Acreage

Section Image
  • 259 Bolton Rd, Winchester, NH 03470
    259 Bolton Rd, Winchester, NH 03470
    259 Bolton Rd, Winchester, NH 03470
    /60

    $899,000

    • 3 Beds
    • 2 Baths
    • 3,472 Sq Ft

    259 Bolton Rd, Winchester, NH 03470

    Stunning & modern unique True Timber Frame home has it all with incredible CT River views an easy commute to MA, VT or Keene. The property welcomes you with well-lit custom retaining walls, expansive perennial gardens, two-car garage, and barn on just under 2 acres. Enjoy outdoor life under the covered patio, relax on one of the many private decks or fire pits. Dual RV hook up with water disposal

    Don Goudreau EXP Realty

    259 Bolton Rd, Winchester, NH 03470
  • 525 Richmond Rd, Winchester, NH 03470
    525 Richmond Rd, Winchester, NH 03470
    525 Richmond Rd, Winchester, NH 03470
    /26

    $145,000

    • Land
    • 21.2 Acres
    • $6,840 per Acre

    525 Richmond Rd, Winchester, NH 03470

    Discover a rare opportunity to own 21.2+/- acres of pristine New Hampshire wilderness in the heart of Winchester. This expansive parcel is defined by its stunning frontage along the tranquil Roaring Brook, offering a picturesque and peaceful setting for your future dream home or private getaway. A standout feature of this property is its significant standing timber value; the land has remained

    Bob Barnard Monadnock Realty Group LLC

    525 Richmond Rd, Winchester, NH 03470
  • 90 Old Swanzey Rd, Winchester, NH 03470
    90 Old Swanzey Rd, Winchester, NH 03470
    90 Old Swanzey Rd, Winchester, NH 03470
    /8

    $100,000

    • Land
    • 4.98 Acres
    • $20,080 per Acre

    90 Old Swanzey Rd, Winchester, NH 03470

    What a place and opportunity to build your new home!!! Just under 5 acres of land, situated on a country road yet minutes to amenities is where you can settle down and be home!!! Multiple spots on the lot that could work for a home. Options are endless!!!

    Emily Lagerberg R.H. Thackston & Company

    90 Old Swanzey Rd, Winchester, NH 03470
  • 9 Scotland Rd, Winchester, NH 03470
    9 Scotland Rd, Winchester, NH 03470
    9 Scotland Rd, Winchester, NH 03470
    /23

    $159,000

    • Land
    • 33.35 Acres
    • $4,768 per Acre

    9 Scotland Rd, Winchester, NH 03470

    Welcome to Winchester, NH. This property is only 5 minutes from downtown Winchester, making it a wonderful place to build your next home. Incorporated in 1753 this town is abundant in history. In the 1830s, Graves & Company, established in Winchester, was among the nation's first manufacturers of musical instruments. Be part of this historical town on 33.35 acres with stunning views to the west

    Jonathan Bafundi Realty One Group Next Level

    9 Scotland Rd, Winchester, NH 03470
  • 0 Ashuelot Main St Unit 4978464, Winchester, NH 03441
    0 Ashuelot Main St Unit 4978464, Winchester, NH 03441
    0 Ashuelot Main St Unit 4978464, Winchester, NH 03441
    /6

    $33,750

    • Land
    • 5.34 Acres
    • $6,320 per Acre

    0 Ashuelot Main St Unit 4978464, Winchester, NH 03441

    This vacant, wooded lot is located off the busy Ashuelot Main St (Route 119) on the west side of Winchester, NH, offering high visibility with a 2024 traffic count of 3,138 vehicles/day per the NH DOT. Buyers should contact the town for more information about use. That said, it is zoned agricultural, this property presents potential for a variety of uses, including but not limited to single

    Karissa Moore K&G Realty Services, Inc.

    0 Ashuelot Main St Unit 4978464, Winchester, NH 03441
  • 240 Forest Lake Rd, Winchester, NH 03470
    240 Forest Lake Rd, Winchester, NH 03470
    240 Forest Lake Rd, Winchester, NH 03470
    /34

    $610,000

    • 4 Beds
    • 2.5 Baths
    • 2,200 Sq Ft

    240 Forest Lake Rd, Winchester, NH 03470

    Real Country Living in an antique post & beam farmhouse on 11+ acres, COMPLETELY remodeled for efficient modern life. The 2,200 sf home (town tax card not updated) completely reimagined over 7 years. On rolling pastureland, the home was stripped to its beams, insulated, and white cedar log sided on the exterior. Pine tongue & groove on the inside; Standing-seam metal roof will last indefinitely.

    Michael Breshears BHG Masiello Peterborough

    240 Forest Lake Rd, Winchester, NH 03470
  • 130 Watson Rd, Winchester, NH 03470
    130 Watson Rd, Winchester, NH 03470
    130 Watson Rd, Winchester, NH 03470
    /52

    $694,900

    • 3 Beds
    • 2 Baths
    • 2,145 Sq Ft

    130 Watson Rd, Winchester, NH 03470

    This beautiful 3-bedroom home is set on 12 acres of designated wildlife habitat overlooking a small pond, just off of a winding lovely rural road. If you are dreaming of the country life with amenities within a 15-minute drive to Keene, this home may be for you. It features cedar siding, radiant heat, solar electric a gourmet spacious kitchen, post and beam, open concept family/dining room, field

    Penelope Seaver Coldwell Banker Realty Nashua

    130 Watson Rd, Winchester, NH 03470
  • 406 Back Ashuelot Rd, Winchester, NH 03441
    406 Back Ashuelot Rd, Winchester, NH 03441
    406 Back Ashuelot Rd, Winchester, NH 03441
    /39

    $600,000

    • 7 Beds
    • 5 Baths
    • 5,607 Sq Ft

    406 Back Ashuelot Rd, Winchester, NH 03441

    Become a part of history! This amazing building was the center for education for generations of local children, and retains the character they will remember. Sitting high on a knoll with a commanding view of the Ashuelot river and historic red roofed covered bridge, this brick beauty stands a historic sentinel. The Current owner is occupying the lower level with 3 bedrooms, wonderful dining room,

    Christine Lewis Brattleboro Area Realty

    406 Back Ashuelot Rd, Winchester, NH 03441
  • 0 Old Hinsdale Rd Unit 1 5052965, Winchester, NH 03470
    0 Old Hinsdale Rd Unit 1 5052965, Winchester, NH 03470
    0 Old Hinsdale Rd Unit 1 5052965, Winchester, NH 03470
    /16

    $169,900

    • Land
    • 18 Acres
    • $9,439 per Acre

    0 Old Hinsdale Rd Unit 1 5052965, Winchester, NH 03470

    Located at the very end of the town maintained road is where you will findthis private 18 acre lot building lot. This lot has been selectively cut opening up many nice walking trails including a cleared building site. Town must approve driveway permit to issue building permit as well as improving a portion of the class VI road where driveway would lead to building site. Electricity is at

    Jerry Chandler R.H. Thackston & Company

    0 Old Hinsdale Rd Unit 1 5052965, Winchester, NH 03470
  • 583 Burt Hill Rd, Winchester, NH 03470
    583 Burt Hill Rd, Winchester, NH 03470
    583 Burt Hill Rd, Winchester, NH 03470
    /55

    $549,900

    • 4 Beds
    • 3 Baths
    • 3,114 Sq Ft

    583 Burt Hill Rd, Winchester, NH 03470

    Welcome to your move-in-ready sanctuary! This beautifully updated home perfectly blends modern comfort with a tranquil natural setting, featuring a peaceful brook running alongside the property for ultimate privacy. Recent high-value upgrades offer total peace of mind, including a brand-new roof, a new 2,500-gallon septic system, fresh paint, and stylish new laminate flooring throughout. The

    Munise Ulker HomeSmart Success Realty LLC

    583 Burt Hill Rd, Winchester, NH 03470
New Hampshire Cheshire County Winchester

Homes for Sale with Acreage in Winchester, NH

Home Trends in Winchester, NH

On average, homes in Winchester, NH sell after 57 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester, NH over the last 12 months is $305,000, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$305,000
Median Single Family Sale Price
$310,000
Average Price Per Sq Ft
$249
Number of Homes for Sale
9
Last 12 months Home Sales
41
Months of Supply
2.60
Median List Price
$302,500
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-2%
How to Buy a Home How to Finance a Home How to Sell a Home

In Winchester, there are currently 10 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Winchester, NH offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Winchester and discover the potential and freedom that comes with owning your own piece of property.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Copyright 2026 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group