Alyssa Halisky Real Estate Agent - Wallace & Co. Sotheby's International Realty

21 & 25 Fulling Mill Rd, Chilmark, MA For Sale $2,250,000 - co-listed by Alyssa Halisky — For Sale $2,250,000 • Co-Listing Agent

Alyssa Halisky listing and buyer's agent for 52 S Summer St, Edgartown, MA - sold for $9,250,000 — Sold $9,250,000

5 Pine Tree Ln, Vineyard Haven, MA For Sale $1,999,000 - listed by Alyssa Halisky — For Sale $1,999,000

49 High St, Edgartown, MA Pending $3,995,000 - listed by Alyssa Halisky — Pending $3,995,000

312 E Chop Dr, Oak Bluffs, MA For Sale $2,295,000 - listed by Alyssa Halisky — For Sale $2,295,000

Alyssa Halisky

Edgartown MA

Wallace & Co. Sotheby's International Realty

66 Closed Sales

$217M Total Value

$275K - $25M Price Range

$3.3M Average Price

Prior 5 years

About Alyssa

Alyssa's extensive knowledge of the Martha's Vineyard real estate market began in 2004. This tenure ensures that her clients have a seamless home buying and selling experience. A licensed REALTOR®, Alyssa has personally been involved in many of the record-breaking estate transactions on the Island. Before joining the Wallace & Co. Sotheby's International Realty team, Alyssa spent six years in the field of Cancer Research. She received her Bachelor of Science Degree in Biochemistry from Bucknell University and her Master of Science Degree in Biotechnology from Johns Hopkins University. The critical thinking skills and intricate processes of biotech have served her well in guiding her clients through what can be complicated Island transactions. Alyssa loves calling the Vineyard her home and lives in West Tisbury with her husband Michael and her three children, Caleb, Laina and Sam.

Home Types: House, Lot/Land

Years of Experience: 22

Education: Bucknell University, John Hopkins University

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	8
Total Value	$30,897,500
Average Sale Price	$3,862,188
Price Range	$970K - $9.3M

Buyer Deals
Total Deals	3
Total Value	$11,900,000
Average Sale Price	$3,966,667
Price Range	$1.4M - $5.8M

Seller Deals
Total Deals	19
Total Value	$60,148,000
Average Sale Price	$3,165,684
Price Range	$550K - $15M

Buyer Deals
Total Deals	9
Total Value	$29,805,000
Average Sale Price	$3,311,667
Price Range	$275K - $9M

Seller Deals
Total Deals	48
Total Value	$177,835,210
Average Sale Price	$3,704,900
Price Range	$409K - $25M

Buyer Deals
Total Deals	18
Total Value	$39,156,755
Average Sale Price	$2,175,375
Price Range	$275K - $9M

5 Year View

Neighborhoods Alyssa is Experienced In

Alyssa's Recent Active Listings

$1,999,000
- 4 Beds
- 3 Baths
- 2,730 Sq Ft
5 Pine Tree Ln

Vineyard Haven, MA
Blending 1920s charm with modern luxury, this beautifully renovated home is tucked away in the sought-after West Chop area of Vineyard Haven. Just steps from the neighborhood beach on the pristine shores of Vineyard Sound, this elegant seaside retreat offers the perfect mix of historic character and contemporary comfort. Inside, a thoughtfully designed floor plan welcomes you with generous living

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$2,295,000
- 3 Beds
- 4 Baths
- 1,425 Sq Ft
312 E Chop Dr

Oak Bluffs, MA
“The Doll House” is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$2,295,000
- 3 Beds
- 2 Baths
- 1,425 Sq Ft
312 E Chop Dr

Vineyard Haven, MA
''The Doll House'' is a landmark East Chop waterfront retreat overlooking Crystal Lake with sweeping views of Vineyard Sound. Originally a charming fishing cottage, this iconic property has been thoughtfully renovated and meticulously maintained, blending timeless Vineyard character with modern comfort. Surrounded by lush hydrangea and perennial gardens, the property boasts nearly 150 feet of

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$1,349,000
- 3 Beds
- 2 Baths
- 1,863 Sq Ft
3 Troy St

Oak Bluffs, MA
Set on a generous 0.3-acre lot in desirable Oak Bluffs, this property offers exceptional potential just moments from Vineyard Sound. A newly installed 6-bedroom septic system opens the door to a variety of expansion opportunities. The home is thoughtfully designed with two separate living areas, ideal for guests or rental possibilities. The main living space features hardwood floors throughout, a

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$45,000,000
- 7 Beds
- 13 Baths
- 11,200 Sq Ft
18 Point Inner Way

Chilmark, MA
A rare offering on the shores of Nashaquitsa Pond, this extraordinary contemporary waterfront estate redefines luxury living in Chilmark. Set on 4.9 acres with a private 115-foot deep-water dock, this one-of-a-kind compound features striking modern architecture, walls of glass, and panoramic water views throughout. The main residence offers six ensuite bedrooms, including a spectacular

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$5,100,000
- Land
- 2.34 Acres
- $2,179,487 per Acre
7 Overview Ln

Oak Bluffs, MA
A rare opportunity to own a 2.4-acre buildable lot within the prestigious Farm Neck Association. Perfectly situated overlooking the lush greens of Farm Neck Golf Club, this remarkable property also offers picturesque water views of Sengekontacket Pond and the distant Vineyard Sound. Design and build your dream home in this sought-after location. As a homeowner in Farm Neck, you'll enjoy exclusive

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$21,500,000
- 10 Beds
- 14 Baths
- 7,598 Sq Ft
56 N Summer St

Edgartown, MA
A rare legacy offering in the heart of Edgartown Village, this extraordinary in-town compound is among the largest on Martha’s Vineyard. Originally built in 1835 and masterfully renovated, it blends historic character with refined modern luxury just moments from Edgartown Harbor, dining, and shopping. Spanning two lots, the property features 10 bedrooms and 14 baths, designed for elegant

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$12,500,000
- 5 Beds
- 3.5 Baths
- 3,700 Sq Ft
18 Spruce Gate Rd

Chilmark, MA
Welcome to an extraordinary coastal retreat within the exclusive gates of Squibnocket Farm, a 450+ acre private community offering access to over two miles of oceanfront, pond frontage, and conservation land. Designed and built by Soikkeli & Company, this elegant home blends timeless New England farmhouse architecture with refined modern luxury. The chef’s kitchen features soapstone countertops,

Alyssa Halisky Wallace & Co. Sotheby's International Realty

$439,500
- Land
- 0.56 Acre
- $784,821 per Acre
5 Candle Maker Cir

Edgartown, MA
Located on a quiet cul-de-sac in a private Edgartown neighborhood, this half-acre parcel offers the perfect setting for your Martha's Vineyard home. Centrally located, the property provides easy access to the bike path and State Forest walking trails. With the recent Massachusetts Affordable Homes Act, this lot is now buildable and will include an approved 3-bedroom septic plan. The site allows

Alyssa Halisky Wallace & Co. Sotheby's International Realty

Recently Sold

$9,250,000

Sold Jul 31, 2026
- 6 Beds
- 7 Baths
- 6,135 Sq Ft
52 S Summer St

Edgartown, MA
- 2% Below List
- $1,508/SF
- 106 Days On Market
- Current Est. Value $9M
Alyssa Halisky Wallace & Co. Sotheby's International Realty

Awards and Designations

NAR - National Association of Realtors
ABR - Accredited Buyer Representative

Other Experience

First Time Homebuyers, Luxury Homes, New Construction

Agent License: Massachusetts #448007129

Alyssa Halisky

(774) 713-9430

Homes for Sale by City

Alyssa Halisky

About Alyssa

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Alyssa is Experienced In

Alyssa's Listings and Deals

Alyssa's Recent Active Listings

Recently Sold

Awards and Designations

Other Experience