Single Family Residence at 301 Tiffany Hill Road, Weare
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 2 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 3 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 4 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 5 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 6 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 7 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 8 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 9 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 10 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 11 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 12 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 13 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 14 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 15 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 16 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 17 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 18 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 19 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 20 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 21 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 22 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 23 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 24 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 25 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 26 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 27 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 28 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 29 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 30 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 31 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 32 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 33 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 34 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 35 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 36 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 37 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 38 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 39 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 40 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 41 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 42 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 43 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 44 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 45 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 46 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 47 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 48 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 49 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 50 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 51 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 52 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 53 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 54 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 55 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 56 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 57 of 58
Single Family Residence at 301 Tiffany Hill Road, Weare, photo 58 of 58
58 photos

$575,000

301 Tiffany Hill Road
Weare, NH 03281-5203
Listed by Anna Kerr · Re/Max Innovative Properties - Windham
Bedrooms
4
Bathrooms
2
Living area
N/A
Year built
1780

About this home

MASSIVE PRICE REDUCTION OF $25K Step back in time and own a remarkable piece of New Hampshire history! Believed to date back to circa 1794, the historic Old Osborne House offers approximately 2,896 square feet of living space on 7.58 picturesque acres, blending timeless character with endless possibilities. Rich in original architectural details, this antique Colonial features 4 bedrooms, 2 bathrooms, six fireplaces, two separate staircases, original wide-plank pine floors, and hand-hewn post-and-beam construction that showcases the craftsmanship of a bygone era. Adding to its intrigue are two hidden rooms beneath the home, believed by local historians to have been connected to the Underground Railroad, making this property as fascinating as it is beautiful. A standout feature is the impressive barn complex, including an attached 40' x 26' two-story workshop and a magnificent 56' x 40' two-story bank barn with classic timber-frame construction, hand-hewn mortise-and-tenon joinery, and a drive-under lower level. Whether your vision includes horses, farming, workshops, antiques, or preserving a historic estate, the possibilities are endless. Privately tucked away on a quiet dirt road, this secluded property is surrounded by peaceful, wooded landscapes that stretch all the way toward Horace Lake. The grounds feature open fields, mature fruit and hickory trees, perennial gardens, and a peaceful setting that perfectly complements the property's rural charm. Approximately 5 acres have electric fencing ready for your animals! Several major updates have already been completed, including a new roof, on-demand heating system, newer furnace, 12 Andersen windows, blown-in insulation in the exterior walls, and a freshly painted exterior. Additional TLC offers an incredible opportunity to restore and personalize this iconic homestead while preserving its rich history and architectural charm.

Property details

MLS
Prime MLS
MLS #
5100275
Property type
Single Family Residence
Subdivision
N/A
Status
Active
Days on market
27
On market date
N/A
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
N/A
Lot size
7.58 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Center Woods School
1.77 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
545
Student:teacher ratio
11.4:1
District
Weare School District
Middle
Weare Middle School
2.09 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
337
Student:teacher ratio
12.0:1
District
Weare School District
High
John Stark Regional High School
2.01 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
580
Student:teacher ratio
9.5:1
District
John Stark Regional School District

Walkability

Blended score for Weare's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

21
Car-dependent
out of 100
EPA National Walkability Index
6.2 / 20 -- Below average walkable
Google Places amenity density
5 / 100
Restaurants & cafes0
Grocery stores0
Parks1
Schools0
Transit stops0
Pharmacies0

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$3,613/mo
$115,000 down
$460,000 loan
Principal & interest$2,984
Property tax (est.)$479
Home insurance (est.)$150

Similar homes you might like

Prime MLS logo

Copyright 2026 PrimeMLS. 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. Data last updated 08/13/26.