40 Orchard Rd, Tisbury, MA 02568
Property image
Property image
OFF MARKET

40 Orchard Rd
Tisbury, MA 02568

  • 6 Beds
  • 5 Baths
  • 3,730 sqft (on 4.50 acres)
6 Beds
5 Baths
3,730 sqft
(on 4.50 acres)

Local Information

  • Map ViewExplore the area around 40 Orchard Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

CURRENTLY UNDER CONTRACT - Enchanted Gentleman's Farm set on an idyllic 4.5 acres in West Tisbury. As you make your way on the winding driveway, you are led up the hill to the main house where you are greeted by stone walls, gardens, fruit trees and grape vines. Just walking through the front door, you will begin to realize the attention to detail the owners had when creating this home and the entire property. The antique timbers were used to frame the main area of the house and elegantly define the spaces within. The owners truly captured the essence of open living while creating cozy spaces to retreat to when needed. The 3,730 of sq. ft. and bedroom count are divided as follows: Main house has 2,590 sq. ft. of living space and features 3 bedrooms and 2.5 baths. Guest house 800 sq. ft. of living space and has 2 bedrooms with 1 bath. Cottage is 240 sq. ft. and has a sleeping loft and 1 bathroom. Each building has a private outdoor shower. You must visit this unique property to appreciate the architectural details, fine craftsmanship and tremendous energy efficiency of every structure. The property has a rural feel but is only 4 miles to downtown and the ferry. The charming guest house, cottage and barn complete this one of a kind Vineyard treasure. If you need more space, the main house septic will accommodate up to 5 bedrooms. Also, plenty of land for to build a garage and pool. For additional information or to tour this property, please contact Michele Moore/Island Real Estate 508-693-4800 ext. 103.
Main House: Timber frame allows for an open living, dining and kitchen area. The gourmet kitchen has stainless steel appliances, honed soapstone countertops and a large center island with cooktop, ash counters and eating bar. All appliances are high-end and Energy Star rated. Beyond the great room is a den. The exquisite details continue in the open staircase going either upstairs or to the lower level. Enter through the double barn-style doors into the master bedroom suite. Walk-in, marble shower. Marble top vanity with double sinks. Large walk-in closet. A set of French doors lead to a private patio with hot tub. Decorative concrete floors throughout with radiant heat. No details were forgotten in this energy efficient home. The unique details continue throughout the second floor. The "hallways" are open to the lower level so the beams can be further enjoyed. Second level includes two roomy bedrooms. A second set of barns doors frame the entrance to the upstairs bathroom. Relax in the soaking tub. A bridge over the great room takes you to the upstairs loft space. Ceiling fans and air conditioning.
Guest house:
The enchanting feel continues as you come upon this charming guest house. With 2 bedrooms, 1 bath and an open living area, the 800 sq. ft. home feels spacious and airy. Two private decks and porch. Full basement. Outdoor shower. Very energy efficient.
Cottage: A private guest cottage almost finishes off this property. With a open studio space, full bathroom with washer/dryer, a sleeping loft, covered porch and outdoor shower, this cottage adds an additional 240 of living space to this property and is the perfect getaway from the main house for your special guests. Outdoor shower. A horse barn does finish off this property. Keep it "as is" or convert to a pool house or recreational area. Its your choice and only limited by your imagination.
40 Orchard Rd, Tisbury, MA 02568 is a 6 bedroom, 5 bathroom, 3,730 sqft multi-family built in 2007. It last sold for $1,750,000 on Apr 14, 2014. It is currently off market. The Trulia Estimate rent is $7,227/month.

Home Highlights

Parking
No Info
Outdoor
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 40 Orchard Rd

Interior Features

Interior Details
BasementTypes of Rooms: Walk In Closet, Dining Room, Laundry Room, Master Bath, Mud Room, Recreation Room, WorkshopCeiling Fan
Heating & Cooling
Heating: Other, Radiant, Propane ButaneCooling System: OtherHeating Fuel: Other
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Windows, Doors, Floors & Walls
Double Paned Windows
Levels, Entrance, & Accessibility
Floors: Concrete, Hardwood

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: ShingleGardenLawnPatio
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 2007
Property Type / Style
Property Type: Multi FamilyArchitecture: Other

Community

Units in Building: 3

Lot Information

Lot Area: 4.50 acres

Price History for 40 Orchard Rd

DatePriceEventSource
04/14/2014$1,750,000Sold
N/A
07/21/2003$670,000Sold
N/A

Market trends in West Tisbury

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
22
3
MoM
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Property Tax and Assessment

Year2025
Tax$13,602
Assessment$3,002,700
Home facts updated by county records

Comparable Sales for 40 Orchard Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1.42
Multi-Family Home
$1,700,000
10/08/25
7
4.5
3,213
1.83
Multi-Family Home
$1,650,000
04/28/26
5
5.5
4,334
1.56
Multi-Family Home
$3,500,000
09/12/25
8
3
3,656
2.07
Multi-Family Home
$1,000,000
05/13/26
4
4
1,999
4.20
Multi-Family Home
$3,050,000
04/15/26
7
5
3,880
4.55
Multi-Family Home
$1,900,000
05/01/26
5
2.5
2,836
5.95
Multi-Family Home
$1,595,000
10/01/25
5
3
2,020

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Assigned Schools

These are the assigned schools for 40 Orchard Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about West Tisbury

At least 4 Trulia users voted on each feature.
  • 86 % Say it's dog friendly

  • 83 % Say car is needed

  • 80 % Say there's holiday spirit

  • 75 % Say it's quiet

  • 62 % Say neighbors are friendly

  • 60 % Say it's walkable to restaurants

  • 60 % Say there's wildlife

  • 60 % Say there are community events

  • 50 % Say yards are well-kept

  • 50 % Say people would walk alone at night

  • 43 % Say parking is easy

  • 38 % Say it's walkable to grocery stores

  • 25 % Say kids play outside

  • 22 % Say there are sidewalks

  • 20 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Dick M.
    "This is a great up-Island area just quietly off a main road and withing walking distance of a grocery store, pharmacy, bakery and the post office - very safe and comfortable and friendly"

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Apartments for Rent

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Homes for sale near 40 Orchard Rd

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Off Market Homes Near 40 Orchard Rd

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