$2,400,000
7 Beds
4 Baths
2,232 sqft (on 3 acres)
220 North Rd, Chilmark, MA 02535
Est. Mortgage $13,249/mo*
Get Pre-QualifiedWe estimate this home will sell faster than 81% nearby.
Home Highlights
Single-Family Home
Built in 1976
3 acre lot
$1,075/sqft
Local Information
- Map ViewExplore the area around 220 North Rd.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
About this House
Welcome to 220 North Road, Chilmark, an idyllic, up-island retreat featuring a 4-BR, post-and-beam, main house and 3-BR guest cottage. Set on three private acres, this verdant oasis is surrounded by preserves, walking trails and even an ancient way that leads directly from the property to Middle Line Woods Preserve, and then all the way to Tea Lane Farm. A two-thirds of an acre conservation buffer runs along the length of the back of the property for further privacy. Just across North Road from the ancient way is the walking entrance to Great Rock Bight. If you enjoy the splendid rural nature of upisland Chilmark, then this is your place. MAIN HOUSE: The rich wooden interior radiates warmth and relaxation and is enhanced by the living room's floor-to-cathedral-ceiling natural stone fireplace. A large deck wraps around nearly half the house, giving you treehouse-like views and a magical setting for outdoor entertaining. GUEST COTTAGE: This intimate log-home is a separate getaway, hidden by a clutch of tall trees nearly 100 yards away from the main house which creates highly protected privacy. Flowers and herb gardens surround its sunny deck, creating a peaceful nook for reading and relaxation. A detached bedroom is like a honeymoon retreat that summer guests will love. A new, 3BR septic system was just installed (July 2026). EACH HOUSE HAS its own septic system and well, making them truly separate and independent. There's room for a swimming pool near the Main House. Leave the congestion of down-island comfortably behind, while enjoying easy recreation access to public lands and beaches (Lucy Vincent, Squibnocket), sailing on Quitsa & Menemsha ponds, and proximity to Menemsha and the Chilmark Store, community center and famed Chilmark Tavern. ASK ABOUT partial Seller financing. Also, ASK ABOUT about Seller lease-back of the Guest Cottage which could significantly reduce the purchase price. Note: Lease-back is an option, not a contingency for a sale to happen.
Last check for updates: about 4 hours ago
Listing courtesy of David Lott
Vineyard Open House Real Estate
We estimate this home will sell faster than 81% nearby.
Home Details for 220 North Rd
|
|---|
Interior Details Basement: The lower level is partially finished with a living room, bedroom and full bath. There is also significant storage space for sailfish/sunfish and other equipment. Washer/dryer is located on this level.Number of Rooms: 11 |
Beds & Baths Number of Bedrooms: 7Main Level Bedrooms: 2Number of Bathrooms: 4Number of Bathrooms (full): 4 |
Dimensions and Layout Living Area: 2232 Square Feet |
Appliances & Utilities Utilities: CblAppliances: Stove: Yes, Washer: Yes |
Heating & Cooling Heating: OFHANo CoolingHas HeatingHeating Fuel: OFHA |
Fireplace & Spa Fireplace: 1 |
Windows, Doors, Floors & Walls Flooring: 2 |
Levels, Entrance, & Accessibility Floors: 2 |
View Has a ViewView: None, Trees/Woods |
|
|---|
Exterior Home Features Other Structures: Boat Shed w/ Main House; Shed w/ Guest CottageExterior: Deck, Patio, C/Tennis, PubBch, H/Tub, Porch, GardenGarden |
Parking & Garage No CarportNo GarageNo Attached GarageParking: On-site |
Frontage Frontage Type: NoneNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
|
|---|
Days on Market: 28 |
|
|---|
Year Built Year Built: 1976Year Renovated: 2019 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
Property Information Parcel Number: 47 |
|
|---|
Price List Price: $2,400,000Price Per Sqft: $1,075 |
|
|---|
MLS Status: A |
|
|---|
Direction & Address City: Chilmark |
|
|---|
Listing Agent Listing ID: 44663 |
|
|---|
Building Area Building Area: 2232 Square Feet |
|
|---|
Lot Area: 3 Acres |
|
|---|
Listing Agreement Type: Co-Ex |
|
|---|
Partially Furnished |
|
|---|
BasementMls Number: 44663 |
Around this home
What Locals Say about Chilmark
At least 2 Trulia users voted on each feature.
100 % Say there's wildlife
100 % Say there are community events
100 % Say car is needed
100 % Say yards are well-kept
78 % Say neighbors are friendly
75 % Say it's dog friendly
75 % Say people would walk alone at night
67 % Say parking is easy
67 % Say it's quiet
60 % Say they plan to stay for at least 5 years
43 % Say there's holiday spirit
33 % Say it's walkable to restaurants
Sourced by Trulia users. Learn more about our methodology.
Market trends in Chilmark
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
39
8MoM
Home Value
Trulia Estimate
$2.25MSince last month
Decreased$47K (-2.1%)Since last year
Decreased$47K (-2.1%)Since last sale
Increased$2M (+259.5%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +106% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $2.25M |
| August 2026 | $2.29M |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.23 | Single-Family Home | $2,225,000 | 10/24/25 | 4 | 3 | 2,968 | |
0.71 | Single-Family Home | $2,800,000 | 08/27/26 | 4 | 3.5 | 2,515 | |
1.14 | Single-Family Home | $2,100,000 | 11/25/25 | 4 | 3 | 2,544 | |
1.18 | Single-Family Home | $3,710,000 | 03/12/26 | 3 | 5 | 3,171 | |
1.10 | Single-Family Home | $4,850,000 | 12/05/25 | 5 | 3.5 | 4,044 | |
1.32 | Single-Family Home | $4,325,000 | 12/05/25 | 5 | 2.5 | 3,885 | |
1.46 | Single-Family Home | $3,700,000 | 05/28/26 | 5 | 4 | 3,413 | |
1.48 | Single-Family Home | $1,775,000 | 11/07/25 | 3 | 2 | 1,728 | |
1.75 | Single-Family Home | $8,178,500 | 10/27/25 | 6 | 4.5 | 4,104 | |
1.73 | Single-Family Home | $6,100,000 | 03/24/26 | 6 | 7 | 5,660 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.14 | $3,900,000 | 3 | 4 | 2,960 | For Sale | |
0.19 | - | - | - | - | Off Market | |
0.23 | $2,504,300 | 4 | 3 | 2,968 | Off Market | |
0.31 | $16,250,000 | 6 | 7 | 8,648 | For Sale | |
0.37 | $3,811,800 | 6 | 3 | 2,297 | Off Market | |
0.47 | $2,516,400 | 6 | 3.5 | 2,229 | Off Market | |
0.60 | $3,795,000 | 4 | 3.5 | 3,426 | For Sale | |
0.61 | $2,243,400 | 4 | 5.5 | 2,405 | Off Market | |
0.66 | $5,202,100 | 4 | 2 | 2,686 | Off Market | |
0.63 | $6,750,000 | 5 | 3.5 | 4,050 | For Sale | |
0.71 | $2,800,000 | 4 | 3.5 | 2,515 | Recently Sold |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Aug 12, 2026 Source: LINK #44663 | Listed For Sale | $2,400,000 |
Jan 11, 2000 Source: N/A | Sold | $625,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $4,369 | $1,941,600 |
Home facts updated by county records
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
David Lott, Vineyard Open House Real Estate
© 2026 LINK, All Rights Reserved. Data last updated: 2026-09-08 15:59:22 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.
Similar Homes You May Like
OPEN WED, 11-1PM1.4 ACRESWallace & Co. Sotheby's International Realty
0.88 ACRESWallace & Co. Sotheby's International Realty
5.45 ACRESTea Lane Associates
3.3 ACRESJessica Holtham, Wallace & Co. Sotheby's International Realty
1.6 ACRESThe Agency
0.93 ACRESSotheby's International Realty
2.88 ACRESSotheby's International Realty
OPEN WED, 11-1PM1.4 ACRESIdalyn Macchia Gilstad, Wallace & Co. Sotheby's International Realty
2.2 ACRESKaren M. Overtoom R.E.
0.34 ACRESWallace & Co. Sotheby's International Realty
0.34 ACRESWallace & Co. Sotheby's International Realty
0.73 ACRESSotheby's International Realty
0.57 ACRESWallace & Co. Sotheby's International Realty
See more homes for sale inChilmark
New Listings near 220 North Rd
- 2.2 ACRESKaren M. Overtoom R.E.
- 5.45 ACRESTea Lane Associates
NEW - 4 HRS AGO3.5 ACRESNorth Star Real Estate, LLC- See more homes for sale inChilmark
Frequently asked questions about 220 North Rd
- What is the estimated monthly payment for 220 North Rd?Based on a $2,400,000 list price with 20% down at today's rates, the estimated monthly payment for 220 North Rd in Chilmark, MA is approximately $13,800 (about $12,725 principal & interest, $1,000 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
- What are the closest schools to 220 North Rd?The closest schools to 220 North Rd in Chilmark, MA are Chilmark Elementary School (rated 8/10), Martha's Vineyard Regional High School (rated 6/10), West Tisbury Elementary School (Pre-K/Middle, rated 7/10).
- What is 220 North Rd estimated to be worth?Trulia's estimated value for 220 North Rd in Chilmark, MA is $2,247,000.
- Does 220 North Rd have laundry facilities?Yes, 220 North Rd in Chilmark, MA has laundry facilities.
- How big is the lot at 220 North Rd?The lot at 220 North Rd in Chilmark, MA is about 3 acres.
- Does 220 North Rd have parking?Yes, 220 North Rd in Chilmark, MA has on-site parking.
220 North Rd, Chilmark, MA 02535 is a 7 bedroom, 4 bathroom, 2,232 sqft single-family home built in 1976. This property is currently available for sale and was listed by LINK on Aug 12, 2026. The MLS # for this home is MLS# 44663.