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Derrike Schmitt
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40 Pleasant Street, Wenham, MA 01984

$2,295,000
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Active Under Contract
BEDS5 BATHS4 full 2 partial SQUARE FEET5,034 MLS#73498310
STATUSActive Under Contract PROPERTY TYPEResidential - Single Family

Property Description

Set on 19 beautiful acres just minutes from Wenham center, this is the kind of property that feels like a world of its own. A 4 bedroom main house, adorable guest cottage, and a 3-car garage, all within a lovely neighborhood setting. The 4319 sq ft single-level ranch is bright, meticulously-maintained, and designed for the way people actually live. The guest cottage is fully equipped and privately situated, functioning as a true second home on the property, ideal for extended family, an au pair, or long-term guests. The land is the heart of it all. Two acres of flat, open lawn offer room for a pool, a garden, or simply the pleasure of open ground around you. Beyond that, seventeen acres of wooded trails provide privacy, a place to explore, and a quality of quiet that is increasingly rare. Walk out your back door and feel miles away, while still being minutes from everything. Top-rated schools, great community, beautiful neighborhood and the best of the North Shore

40 Pleasant Street | MLS# 73498310

This single family home located at 40 Pleasant Street, Wenham, MA 01984 is currently listed for sale with an asking price of $2,295,000. This property was built in 1945 and has 5 bedrooms and 4 full and 2 partial baths with 5034 sq. ft. Search Wenham real estate on derrikeschmitt.masiellogrouprealestate.com today.

Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Radon Remediation System, Concrete
Cooling: Central Air
Fireplaces: 3
Garage: 3
Heating: Baseboard
Home Style: Ranch
Lot Size: 19.00 Acres
Roof Type: Asphalt/Composition Shingles
Taxes: $31,132
Year Built: 1945

Amenities

Bathroom - Half
Bathroom
Foyer
Sitting Room
Play Room
Exercise Room
Internet Available - DSL
Porch - Enclosed
Patio
Covered Patio/Deck
Rain Gutters
Hot Tub/Spa
Professional Landscaping
Decorative Lighting
Guest House

Feature Descriptions

Appliances: Gas Water Heater, Oven, Dishwasher, Microwave, Range, Refrigerator, Freezer, Washer, Dryer, Wine Refrigerator, Range Hood, Water Softener
Beach Rights: Y
Building Area Total: 5034
Community Features: Public Transportation, Shopping, Walk/Jog Trails, Stable(s), Bike Path, Conservation Area, House of Worship, Private School, Public School
Compensation Based On: N/A
Compensation Broker Transaction: N/A
Compensation Buyer Agency: N/A
Compensation Sub Agency: N/A
Compensation Sub Agency Offered: N/A
Days on Site: 9
Dining Room: Flooring - Hardwood, Recessed Lighting
Electric: 200+ Amp Service
Exclusions: Swings On Back Porch
Exterior: Frame
Family Room: Cable Hookup, Exterior Access, High Speed Internet Hookup, Open Floorplan
Fireplace Features: Master Bedroom
Fireplace Y/N: Yes
Flooring: Wood, Tile
GarageY/N: Yes
HeatingY/N: 1
Hot Tub: Yes
Kitchen: Flooring - Wood, Countertops - Stone/Granite/Solid, Cabinets - Upgraded, Country Kitchen, Recessed Lighting, Remodeled
Laundry: First Floor, Electric Dryer Hookup, Washer Hookup
Living Room: Flooring - Hardwood, Recessed Lighting
Lot Features: Wooded
Master Bathroom: Yes
Master Bedroom: Closet/Cabinets - Custom Built, Flooring - Hardwood, Exterior Access, Recessed Lighting
Open Parking Y/N: Yes
Other Structures: Guest House
Parcel Number: 3219049
Parking Features: Detached, Garage Door Opener, Garage Faces Side, Shared Driveway, Off Street, Driveway, Paved
Parking Total: 11
Patio And Porch: Porch - Enclosed, Patio, Covered
Rooms Total: 11
Sewer: Private Sewer
Spa: Yes
Spa Features: Private
Spa Y/N: Yes
Special View Info: Scenic View(s)
Utilities: for Gas Range, for Electric Oven, for Electric Dryer, Washer Hookup
Water: Public
Waterfront Features: Beach Access, Ocean, Beach Ownership(Public)
Window Features: Insulated Windows
Wooded: Yes

Room Sizes

Bathroom 1: 8.42 X 12.00 Level - Main,First
Bathroom 2: 8.17 X 8.67 Level - Main,First
Bathroom 3: 4.00 X 4.42 Level - First
Bedroom 2: 13.75 X 12.00 Level - Main,First
Bedroom 3: 13.92 X 12.75 Level - Main,First
Dining Room: 15.58 X 24.58 Level - Main,First
Family Room: 25.00 X 23.25 Level - Main,First
Kitchen: 16.25 X 13.83 Level - Main,First
Living Room: 14.17 X 15.83 Level - Main,First
Primary Bedroom: 16.17 X 22.17 Level - Main,First

Local Schools

High School: Hamilton Wenham
Middle School: Hamilton Wenham
Elementary School: Hamilton Wenham

Listed By / Shown By

Listed By

Agency Name: Compass
Agency Phone: 617-206-3333
Agent Name: Nest | Syndi Zaiger Group

Shown By

Agent Name: Derrike Schmitt
Agent Phone:
Agency Title: Better Homes and Gardens Real Estate The Masiello Group

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Estimated Payment

$ 8,371.38 per month $5,107.68 Principal & Interest $2,594.33 Property Tax $669.38 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 04/18/2026. The listing information on this page last changed on 04/18/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sat 04/18/2026 12:00:18 AM EST) or MLSPIN MLS (last updated Fri 04/17/2026 11:38:27 PM EST) or Prime MLS (last updated Fri 04/17/2026 11:33:41 PM EST) or MREIS (last updated Fri 04/17/2026 11:55:33 PM EST). Real estate listings held by brokerage firms other than Better Homes and Gardens Real Estate The Masiello Group may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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