Set amongst beautifully landscaped grounds and vibrant gardens, this inviting Chappaquiddick retreat offers a wonderful sense of privacy and tranquility. Stunning hydrangeas frame the property, also complemented by mature trees, colorful blooms, and established gardens, creating a beautiful setting throughout the seasons. Multiple outdoor spaces invite relaxing and entertaining, with a heated saltwater pool, completed in 2025, serving as the centerpiece. Inside, warm and inviting living spaces are filled with natural light, while shiplap details and a relaxed coastal aesthetic give the home a classic island feel. Vaulted ceilings and thoughtful attention to detail enhance the home’s comfortable, refined character, while a thoughtfully designed single-level layout offers the ease and convenience of true first-floor living, with a private primary suite and separate guest wing providing an ideal sense of space and privacy. The detached studio with workshop is a hobbyist’s dream, overlooking the pool and offering a versatile space for creative pursuits, hobbies, or use as a pool cabana.
Single-familyProperty Type
2011Year Built
1.7 acresLot Size
$1,591Price/Sq.Ft.
2 garage spacesParking
Listed by Katie Donahue & Rachel Serwa Group• Sandpiper Realty, Inc.
Listed by Katie Donahue & Rachel Serwa Group• Sandpiper Realty, Inc.
Chappaquiddick, located between Edgartown Harbor and Cape Poge Bay, is a coastal and rural Edgartown neighborhood with barrier beaches and salt marshes. The Chappy Ferry landing on Chappaquiddick Road concentrates the island’s daily rhythm, with bikes lining up, beach gear in tow, and the water crossing setting the pace. The Mytoi Japanese Garden, Cape Poge Wildlife Refuge, and the Chappaquiddick Community Center act as cultural anchors beyond the shoreline. Architecture leans to shingled cottages and low-profile homes tucked behind scrub oak. Dirt lanes, dunes, and quiet ponds shape a outdoors-first routine. Sunrises over Cape Poge and sunsets back toward Edgartown define the geography.
Provided by Walk Score and Local Logic
Offer insights
149 Litchfield Rd · $4,725,000
$4.74M and above
75% chance or better to win
Why $4.74M+ is a strong offer
DAYS ON MARKET
8 days
The average home goes pending in 63 days.
SALE-TO-LIST
98.6%
Most homes are selling 1% below list price.
About offer insights
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
13 total rooms
Partially finished basement
One fireplace
Bathrooms
3 full bathrooms
2 half bathrooms
Heating & cooling
Central heating (forced air)
Central air conditioning
Exterior features
Cleared, level lot
Lot size approximately 1.7 acres
Directions: Chappaquiddick Road to Litchfield Road; 149 is about 0.2 miles down on the right
Home design
Single family residence
Renovated since original construction
Parking
2-car garage (covered)
5 additional open parking spaces
7 total parking spaces
Construction
Concrete perimeter foundation
Year built per public records (renovated since)
Utilities
Private water
Private sewer
HOA & community
Not a senior community
Financial info
Active listing
Electricity and solar
View estimated energy costs and solar savings for this home
Set privately in the heart of Chappaquiddick, this property offers a rare combination of exceptional landscaping with a refined home that exudes quality. While beaches, trails, and even downtown Edgartown are readily available, this property is a standalone oasis. On the exterior the home greets with high-end materials, including cedar shingle roof and siding, copper accent, and Azek trim. Multiple entrances lend naturally to indoor/outdoor living, allowing for enjoyment of bluestone patios, Ipe deck, flower and vegetable gardens, and open lawns. The interior of the home centers on a cathedral-ceiling great room, with fieldstone fireplace and chef’s kitchen at opposite ends. The primary suite is private, yet conveniently located, with a luxurious bathroom and walk-in closets. Two additional bedrooms are set on a separate wing of the house, each with private bathrooms. There is also a two-car garage and studio/workshop that is beautifully finished.
CCIMLS #21508519
Oct 27, 2016
Sold
$1,165,000
$392/sq ft
Aug 19, 2016
Pending
—
Jun 22, 2016
Price Changed
$1,575,000
$530/sq ft
Sep 2, 2015
Listed
$1,700,000
$573/sq ft
+28
Delightful home enjoys close proximity to Edgartown Village and secluded beaches that are some of the Vineyard's best-kept secrets. Custom designed with Chef's kitchen, open floor plan, secluded guest wing, detached garage, energy efficient HVAC system, in-slab radiant, eco friendly spray foam insulation, low-maintenance exterior with fieldstone, granite, and custom outdoor shower. The 4-bedroom septic allows for future expansion, and a pool can be easily added to the property. Partially finished basement is ready to be completed with a rec room, wet bar, bathroom, and flex room, or can be converted into an additional bedroom. Call Bill Rossi at Sotheby's (508.367.2918) to request a detailed specification sheet, and to arrange a showing of this luxe seacoast retreat.
MLS PIN #71027165
Jun 9, 2011
Sold
$360,000
$121/sq ft
Jun 7, 2011
Listing Removed
—
Feb 2, 2010
Listed
$429,900
$145/sq ft
Public Records
Aug 17, 2006
Sold
$345,000
$116/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$6,738 (+11.2%)
$239,800 + $2,433,900
$2,673,700
2022
$6,060 (+7.0%)
$263,700 + $1,736,300
$2,000,000
2020
$5,664 (−6.4%)
$287,700 + $1,403,000
$1,690,700
2019
$6,051 (+37.0%)
$311,700 + $1,251,800
$1,563,500
2018
$4,416 (+12.3%)
$311,700 + $829,400
$1,141,100
2017
$3,934 (−5.5%)
$299,700 + $808,600
$1,108,300
2016
$4,164 (+79.8%)
$239,800 + $910,400
$1,150,200
2015
$2,316
$287,700 + $379,700
$667,400
Public record
Beds
—
Baths
—
Stories
—
Lot width
—
Lot depth
—
Lot size
1.7 Acres
Year renovated
—
Finished Sq. Ft.
—
Unfinished Sq. Ft.
—
Total Sq. Ft.
—
Year built
—
Style
Other
County
Dukes County
APN
3770523
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
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Last updated by owner on Jul 19, 2023.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
3/10 Heat Factor
7 days above 88° expected this year, 21 days in 30 years
8/10 Wind Factor
94% chance of strong winds in next 30 years
2/10 Air Factor
2 unhealthy days expected this year, 2 days in 30 years
Provided by First Street
Historical weather
Edgartown, MA • 02539
Average low and high temperatures (°F)
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63
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54
40
43
30
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Sun exposure
Try the sun simulator tool to see how light moves across the property at different times of day and year.
Provided by Shadowmap
Redfin Estimate for 149 Litchfield Rd
$4,626,708
$98K under list price of $4.73M
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $1.1M to $4.4M.