99 The Boulevard Edgartown — Photo 1 of 37
$2,455,000
Investment Analysis — 99 The Boulevard
Edgartown, MA 02539
Based on HUD Small Area Fair Market Rent for Dukes County, MA, a 4-bedroom in 02539 carries an estimated $3,430/mo in gross rent — about a 1.05% cap rate and $25,680/yr in estimated NOI at the $2,455,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
4.5
SqFt
3,039
Style
Single Family
Built
1985
Welcome to a beautifully renovated custom contemporary colonial located just 1/3 mile from the Sengekontacket Pond boat landing. Perfect for kayaking, paddle boarding, and coastal living, this builder-owned home seamlessly blends classic Vineyard charm with modern luxury. The bright, open-concept main floor features a wood-burning fireplace, custom kitchen, and direct access to a private backyard oasis with a stone patio, built-in grill, and fire pit. Spanning three finished levels, the home offers and unmatched layout versatility. The second floor features a loft that connects via a balcony to a private studio/office suite above the garage. The third-floor retreat boasts its own full bath and a private balcony with elevated views. Key upgrades include brand-new HVAC, Andersen windows, refinished hardwood floors and a MicroFAST septic system. An exceptional year-round residence or high-yield investment property with a strong rental history!
ADU Potential
Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 3,039 sq ft principal dwelling). Lot size: 12,000 sq ft.
Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Geography
Property History
$2,475,000
Sep 15, 2026
MLS® 73577541
$2,595,000
Dec 3, 2025
MLS® 73321001
$2,595,000
Dec 21, 2024
MLS® 73321001
Listing Agent: Jennifer Dasilva
Listing Office: Compass
MLS® Number: 73577541