List Price: $749,900 | $281 per sq.ft. | 3 Bedroom | 2 Bathroom | 1.5 Story Single Family Home
Listed Friday May 15, 2026 | MLS# 5089279
295 Manning Hill Road Winchester NH
Listed by Paul Rodenhauser BHG Masiello Keene
Own your piece of paradise! Rarely does a property offering this much land and a beautifully maintained home become available in Cheshire County, NH. This single-owner Cape-style home features 3 bedrooms, 2 bathrooms, and a finished walk-out lower-level in-law suite, all set on approximately 37± acres with peaceful privacy and stunning natural surroundings. Inside, you'll find a warm and functional layout with custom cherry wood kitchen cabinets, natural wood finishes, a breakfast bar, and formal dining room. The living room is filled with abundant natural light, while mini-split heating and cooling provide year-round comfort. A standing seam metal roof offers added durability and peace of mind, while the 2-flue chimney provides the option for wood or pellet stove hook-up. One of the home's standout features is the 16x16 enclosed sitting porch complete with custom windows, beautiful woodwork, insulation, and a gas stove, creating a perfect year-round retreat. The first-floor primary bedroom offers slider access to a private deck and is conveniently located near a full bath with jacuzzi tub. Upstairs are two additional bedrooms with oversized skylights and windows bringing in exceptional natural light. The finished walk-out lower level includes a full in-law suite with kitchen, bath, washer and dryer, and slider access, ideal for multi-generational living or rental potential. The land is equally impressive, featuring approximately 20± acres of fenced pasture used for horses since 1987, plus additional acreage with trails, timber, streams, a pond, and beautiful views. Outdoor amenities include an above-ground pool, gazebo, koi pond, fruit trees including peach and apple, perennial gardens, garage space, hardscaping, and a versatile barn/shed perfect for animals, hobbies, storage, or workshop use. Enjoy peaceful country living while remaining close to town amenities. A truly special property offering space, functionality, and endless possibilities.
Flooring: Carpet | Hardwood
Total Rooms: 7
Total Baths: 2
Full Baths: 2
Total Bedrooms: 3
Basement: Finished
Year Built: 1987
Type: Wood Frame | Cedar Exterior

Building Info
Finished Sq.Ft.: 2671
Above Grade Sq.Ft.: 1512
Below Grade Sq.Ft.: 1159
Apx Below Grade Unfinished Sq.Ft.: 0

Exterior Info
Style: Cape
Roof: Metal | Standing Seam

Utilities
Electric: Circuit Breaker(s)
Water: Drilled Well | Private
Sewer: Private

Land Description:
Country Setting | Field/Pasture | Hilly | Landscaped | Mountain View | Open | Pond | Secluded | Timber | Trail/Near Trail | View | Wooded | Near Paths | Rural | Near ATV Trail | Private
Lot size: 37 acres
Zoned: RURAL
Surveyed: Yes
Flood Zone: No
Seasonal: No
Driveway: Crushed Stone | Gravel



Block - 0000
Taxes $7,417
Assesed Value Not Reported
Schools
School District: Winchester School District
Elementary School: Winchester School
Middle School: Winchester School
High School: Hinsdale Sr. High School

© 2000-2026 Clerkin Agency Real Estate
NEREN Logo
565 Maple Street, White River Junction, Vermont. 05001 802-295-1355
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. Data last updated June 2nd, 2026

PLEASE NOTE: Both New Hampshire and Vermont law require brokers and agents to disclose at the “time of first business meeting, prior to any discussion of confidential information”, in New Hampshire’s case, and “first reasonable opportunity”, in Vermont’s case, the nature of the relationships brokers have or may have with customers and clients. Each state requires that a disclosure form be presented to consumers for their review and acknowledgment at the appropriate time. These forms can be accessed here:
VT: VERMONT REAL ESTATE COMMISSION MANDATORY CONSUMER DISCLOSURE FORM
NH: NEW HAMPSHIRE REAL ESTATE COMMISSION BROKERAGE RELATIONSHIP DISCLOSURE FORM