Winchester, NH Homes

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  /36

  $725,000

  • 2 Beds
  • 1.5 Baths
  • 1,351 Sq Ft

  27 Headlands Rd, Winchester, NH 03470

  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

  Vincent Dolan RE/MAX Town & Country

  27 Headlands Rd, Winchester, NH 03470
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  /17

  $295,000 Sold Feb 27, 2026

  19 Toofs Dr, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1973

  Last Sold Summary

  • 1% Below List Price
  • $219/SF
  • 19 Days On Market

  Current Estimated Value $296,856

  Last Listing Agent Curtiss Thornbrugh HKS Associates, Inc.

  19 Toofs Dr, Winchester, NH 03470
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  Not Listed For Sale

  217 Warwick Rd, Winchester, NH 03470

  • 3 Beds
  • 946 Sq Ft
  • Built 1987

  217 Warwick Rd, Winchester, NH 03470

  Last Sold Summary

  • $79/SF
  • 12 Days On Market

  Last Sold Price $75,000

  Last Listing Agent Carol Slocum Keller Williams Realty Metro-Keene
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  /57

  $549,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,832 Sq Ft

  159 Ashuelot Main St, Ashuelot, NH 03441

  BRAND NEW, Classic and modern home close to all town services, but located in a rural setting! Colonial with 4 bedrooms, 2 and 1/2 baths and a spacious, heated attached two car garage with EV plug! This energy efficient home is stick built with high quality construction! The expansive gorgeous kitchen has new fully warranted appliances, a large eat at island, beautiful quartz countertops! Living

  Ralph Harvey Listwithfreedom.com

  159 Ashuelot Main St, Ashuelot, NH 03441
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  /53

  $310,000 Sold Aug 15, 2025

  384 Richmond Rd, Winchester, NH 03470

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $239/SF
  • 6 Days On Market

  Current Estimated Value $308,951

  Last Listing Agent Kirsten Perkins BHG Masiello Keene

  384 Richmond Rd, Winchester, NH 03470
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  /14

  Est $219,000 Not Listed For Sale

  9 Mechanic St, Winchester, NH 03470

  • Studio
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1826

  9 Mechanic St, Winchester, NH 03470

  Last Sold Summary

  • 265% Above List Price
  • $30/SF
  • 282 Days On Market

  Last Sold Price $60,000

  Last Listing Agent Bruce Murphy Keller Williams Realty Metro-Keene
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  /34

  $610,000 Under Contract

  • 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
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  /43

  $218,500 Sold Aug 01, 2025

  102 Keene Rd, Winchester, NH 03470

  • 3 Beds
  • 1.5 Baths
  • 3,603 Sq Ft
  • Built 1860

  Last Sold Summary

  • 22% Below List Price
  • $61/SF
  • 101 Days On Market

  Current Estimated Value $226,700

  Last Listing Agent Denise Thomas BHG Masiello Keene

  102 Keene Rd, Winchester, NH 03470
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  Not Listed For Sale

  0 Old Westport Rd, Winchester, NH 03470

  0 Old Westport Rd, Winchester, NH 03470

  Last Sold Summary

  • 15 Days On Market

  Last Sold Price $215,000

  Last Listing Agent Anna Schierioth HKS Associates, Inc.
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  /24

  $450,000 Under Contract

  • 3 Beds
  • 2 Baths
  • 1,668 Sq Ft

  29 Verry Brook Rd, Winchester, NH 03470

  Find yourself at home in this beautiful Winchester, NH property, built in 2008 with a 5 Star Plus energy rating. It offers an ideal mix of comfort, efficiency, and outdoor space. The open-concept kitchen, living, and dining area is filled with natural light and flows directly to the deck, perfect for everyday living and entertaining. The first floor features two bedrooms and two bathrooms,

  MacKenzie Rokes Keller Williams Realty Metro-Keene

  29 Verry Brook Rd, Winchester, NH 03470
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  /28

  $160,000 Sold Apr 18, 2025

  7 Dubriske Ct, Ashuelot, NH 03441

  • 3 Beds
  • 1 Bath
  • 902 Sq Ft
  • Built 1875

  Last Sold Summary

  • 15% Below List Price
  • $177/SF
  • 15 Days On Market

  Current Estimated Value $165,818

  Last Listing Agent Jerry Chandler R.H. Thackston & Company

  7 Dubriske Ct, Ashuelot, NH 03441
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  Not Listed For Sale

  99 Keene Rd, Winchester, NH 03470

  • 4 Beds
  • 3 Baths
  • 1,881 Sq Ft
  • Built 1890

  99 Keene Rd, Winchester, NH 03470

  Last Sold Summary

  • $142/SF
  • 5 Days On Market

  Last Sold Price $268,000

  Last Listing Agent Emily Lagerberg R.H. Thackston & Company
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  /52

  $694,900 Pending

  • 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
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  /12

  $340,000 Sold May 02, 2025

  372 Forest Lake Rd, Winchester, NH 03470

  • 2 Beds
  • 1 Bath
  • 820 Sq Ft
  • Built 1955

  Last Sold Summary

  • 9% Below List Price
  • $415/SF
  • 118 Days On Market

  Current Estimated Value $328,238

  Last Listing Agent Vincent Dolan RE/MAX Town & Country

  372 Forest Lake Rd, Winchester, NH 03470
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  /14

  Not Listed For Sale

  19 Chapel St, Winchester, NH 03470

  • 4 Beds
  • 2 Baths
  • 2,409 Sq Ft
  • Built 1900

  19 Chapel St, Winchester, NH 03470

  Last Sold Summary

  • $114/SF
  • 44 Days On Market

  Last Sold Price $274,500

  Last Listing Agent Darlene Conca
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  /3

  $2,100,000

  • Land
  • 1,002 Acres
  • $2,096 per Acre

  00 New Hampshire 10 Unit multiple, Winchester, NH 03470

  Located in the town of Winchester in southwestern New Hampshire, this portfolio of two non-contiguous forestland parcels totaling 1,002± acres includes a high-quality timber resource, broad ecological attributes, several mountain peaks, and numerous recreational opportunities. In addition, much of the land abuts or is located near thousands of acres of conservation ownerships, enhancing value and

  Steve Gauthier LandVest, Inc./New Hampshire

  00 New Hampshire 10 Unit multiple, Winchester, NH 03470
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  /60

  $849,000 Sold Oct 16, 2025

  463 Old Spofford Rd, Winchester, NH 03470

  • 3 Beds
  • 3.5 Baths
  • 3,423 Sq Ft
  • Built 2002

  Last Sold Summary

  • $248/SF
  • 5 Days On Market

  Current Estimated Value $841,051

  Last Listing Agent Edith Fifield BHG Masiello Keene

  463 Old Spofford Rd, Winchester, NH 03470
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  Not Listed For Sale

  66 Richmond Rd, Winchester, NH 03470

  • 4 Beds
  • 3 Baths
  • 3,070 Sq Ft
  • Built 1920

  66 Richmond Rd, Winchester, NH 03470

  Last Sold Summary

  • $103/SF
  • 126 Days On Market

  Last Sold Price $315,000

  Last Listing Agent Anna Schierioth HKS Associates, Inc.
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  /12

  $80,000

  • Land
  • 1.21 Acres
  • $66,116 per Acre

  258 Bolton Rd, Winchester, NH 03470

  ***PRICE REDUCTION!*** Cleared 1.21-acre lot that is waiting for you to build your dream home and there are no restrictions on the type of build. The land has been mowed and maintained by the sellers and is located in a highly desirable country setting. Test pit has been completed and is available for viewing. Conveniently located near schools, shopping area, hiking and biking trails and Forest

  Christine Houston Greenwald Realty Group

  258 Bolton Rd, Winchester, NH 03470
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  /15

  $472,550 Sold Dec 01, 2025

  63 Prospect Hill Rd, Richmond, NH 03470

  • 3 Beds
  • 1 Bath
  • 1,470 Sq Ft
  • Built 1960

  Last Sold Summary

  • 5% Below List Price
  • $321/SF
  • 70 Days On Market

  Last Listing Agent Heather Peterson Four Seasons Sotheby's International Realty

  63 Prospect Hill Rd, Richmond, NH 03470
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  /40

  Not Listed For Sale

  21 Richmond Rd, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 2,624 Sq Ft
  • Built 1840

  21 Richmond Rd, Winchester, NH 03470

  Last Sold Summary

  • $90/SF
  • 8 Days On Market

  Last Sold Price $235,000

  Last Listing Agent Deborah Lucey RE/MAX
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  /24

  $259,900 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,424 Sq Ft

  886 Keene Rd, Winchester, NH 03470

  Welcome to 886 Keene Rd, a lovingly maintained home where timeless 1875 charm meets thoughtful modern updates. Set on a generous 0.47-acre lot, this property offers space, privacy, and a sense of calm that’s increasingly hard to find.From the moment you arrive, the home makes a warm first impression with classic appeal. A fenced-in front yard creates a welcoming buffer from the road—perfect

  Rosemarie Ledogar RD Ledogar Real Estate

  886 Keene Rd, Winchester, NH 03470
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  /41

  $450,000 Sold Aug 11, 2025

  72 Watson Rd, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 2,234 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $201/SF
  • 29 Days On Market

  Current Estimated Value $454,218

  Last Listing Agent Kristin Reyes REAL Broker NH, LLC

  72 Watson Rd, Winchester, NH 03470
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  Not Listed For Sale

  42 Parker St, Winchester, NH 03470

  • 5 Beds
  • 2 Baths
  • 3,967 Sq Ft
  • Built 1900

  42 Parker St, Winchester, NH 03470

  Last Sold Summary

  • $95/SF
  • 10 Days On Market

  Last Sold Price $377,000

  Last Listing Agent Dick Thackston R.H. Thackston & Company
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  /60

  $849,900

  • 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
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  /50

  $400,000 Sold Aug 28, 2025

  110 Bolton Rd, Winchester, NH 03470

  • 2 Beds
  • 2 Baths
  • 1,748 Sq Ft
  • Built 1977

  Last Sold Summary

  • 17% Below List Price
  • $229/SF
  • 7 Days On Market

  Current Estimated Value $405,139

  Last Listing Agent Greg Carter Four Seasons Sotheby's International Realty

  110 Bolton Rd, Winchester, NH 03470
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  /40

  Not Listed For Sale

  23 Ashuelot St, Winchester, NH 03470

  • 4 Beds
  • 4 Baths
  • 2,484 Sq Ft
  • Built 1800

  23 Ashuelot St, Winchester, NH 03470

  Last Sold Summary

  • $161/SF
  • 35 Days On Market

  Last Sold Price $400,000

  Last Listing Agent Dick Thackston R.H. Thackston & Company
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  /15

  $275,000

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft

  290 Scotland Rd, Winchester, NH 03470

  Drive up the driveway to a private homesite with old garden beds, privacy, perhaps a place for a horse. This one level home will work for almost anyone! Enter this 2 bath home through an enclosed porch which could be part mudroom and partially an area to relax on in good weather. The kitchen has a good working area with a double sink, refrigerator, electric stove and the washer and dryer behind

  Susan Doyle BHG Masiello Keene

  290 Scotland Rd, Winchester, NH 03470
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  $309,250 Sold Oct 03, 2025

  224 Morgan Rd, Winchester, NH 03470

  • 3 Beds
  • 2 Baths
  • 1,280 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $242/SF
  • 5 Days On Market

  Current Estimated Value $324,293

  Last Listing Agent Anna Schierioth HKS Associates, Inc.

  224 Morgan Rd, Winchester, NH 03470
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  Not Listed For Sale

  27 Ashuelot St, Winchester, NH 03470

  • 6 Beds
  • 2 Baths
  • 3,300 Sq Ft
  • Built 1800

  27 Ashuelot St, Winchester, NH 03470

  Last Sold Summary

  • $112/SF
  • 24 Days On Market

  Last Sold Price $370,000

  Last Listing Agent Dick Thackston R.H. Thackston & Company
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  /26

  $135,000

  • Land
  • 21.2 Acres
  • $6,368 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
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  /60

  $310,000 Sold Jan 28, 2026

  153 Back Ashuelot Rd, Winchester, NH 03470

  • 3 Beds
  • 3.5 Baths
  • 2,688 Sq Ft
  • Built 1785

  Last Sold Summary

  • 17% Below List Price
  • $115/SF
  • 199 Days On Market

  Current Estimated Value $329,443

  Last Listing Agent Aimpoint Realty Group Keller Williams Realty-Metropolitan

  153 Back Ashuelot Rd, Winchester, NH 03470
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  /13

  Est $104,248 Not Listed For Sale

  57 Ashuelot St, Winchester, NH 03470

  • 3 Beds
  • 1.5 Baths
  • 1,165 Sq Ft
  • Built 1915

  57 Ashuelot St, Winchester, NH 03470

  Last Sold Summary

  • 16% Above List Price
  • $77/SF
  • 36 Days On Market

  Last Sold Price $90,000

  Last Listing Agent Dick Thackston R.H. Thackston & Company
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  /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
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  /14

  $100,000 Sold Nov 21, 2025

  28 Staddle Hill Rd, Winchester, NH 03470

  • 2 Beds
  • 1 Bath
  • 552 Sq Ft
  • Built 1982

  Last Sold Summary

  • 15% Below List Price
  • $181/SF
  • 29 Days On Market

  Current Estimated Value $105,909

  Last Listing Agent Anna Schierioth HKS Associates, Inc.

  28 Staddle Hill Rd, Winchester, NH 03470
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  /22

  Not Listed For Sale

  19 Ashuelot Main St, Ashuelot, NH 03441

  • 4 Beds
  • 2 Baths
  • 2,414 Sq Ft
  • Built 1900

  19 Ashuelot Main St, Ashuelot, NH 03441

  Last Sold Summary

  • $85/SF
  • 5 Days On Market

  Last Sold Price $205,000

  Last Listing Agent Emily Lagerberg R.H. Thackston & Company
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  /25

  $350,000

  • 2 Beds
  • 1 Bath
  • 937 Sq Ft

  49 Forest Lake Cir, Winchester, NH 03470

  Kick back and relax at this stylish year-round lake area country cottage. Includes deed access to beautiful Forest Lake. This vibrant gem was recently renovated with updated appliances, butcher block countertops and hardwood flooring. This home features vaulted ceilings, laundry hook-ups, patio and deck. Currently operated as a thriving and profitable year-round vacation rental. Home can be

  Vincent Dolan RE/MAX Town & Country

  49 Forest Lake Cir, Winchester, NH 03470
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  /11

  $55,000 Sold Jul 31, 2025

  0 Old Swanzey Rd, Winchester, NH 03470

  • Land
  • 2.64 Acres
  • $20,833 per Acre

  Last Sold Summary

  • 5% Below List Price
  • 91 Days On Market

  Last Listing Agent Emily Lagerberg R.H. Thackston & Company

  0 Old Swanzey Rd, Winchester, NH 03470
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  /14

  Est $178,791 Not Listed For Sale

  862 Keene Rd, Winchester, NH 03470

  • 1 Bed
  • 1 Bath
  • 576 Sq Ft
  • Built 1952

  862 Keene Rd, Winchester, NH 03470

  Last Sold Summary

  • 156% Above List Price
  • $121/SF
  • 143 Days On Market

  Last Sold Price $69,900

  Last Listing Agent Anna Schierioth HKS Associates, Inc.
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  /20

  $299,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft

  21 Kapper Dr, Winchester, NH 03470

  Makeover Magic! This beautifully renovated 3-bedroom, 1-bath ranch has been completely gutted to the studs and thoughtfully rebuilt by a local builder. Upgraded electrical panel and lines, and here’s what’s NEW - an energy-efficient furnace, all plumbing, drywall, windows, doors, flooring, kitchen, bathroom, and appliances!The upgrades continue outside with a brand-new roof and vinyl siding for

  Ralph Harvey Listwithfreedom.com

  21 Kapper Dr, Winchester, NH 03470

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