39 Pleasant Street Provincetown — Photo 1 of 34
Recent Drop: $50,000
$1,849,000
Investment Analysis — 39 Pleasant Street
Provincetown, MA 02657
Based on HUD Small Area Fair Market Rent for Barnstable Town, MA MSA, a 3-bedroom in 02657 carries an estimated $2,600/mo in gross rent — about a 0.79% cap rate and $14,523/yr in estimated NOI at the $1,849,000 list price. Adjust every assumption in the calculator below.
Beds
3
Baths
2
SqFt
1,368
Style
Single Family
Built
1850
Quintessential Provincetown Living in the West End Charming, sun-filled and perfectly situated in Provincetown’s highly desirable West End, this 3-bedroom, 2-bath single-family home offers the ideal blend of comfort, character and location. Natural light fills the home, creating bright, inviting spaces throughout. Outside, a beautifully landscaped yard and patio provide a private setting for summer dinners, morning coffee or relaxing after the beach. The primary bedroom opens to its own covered deck—a wonderful retreat for enjoying the Cape air in every season. Just moments from Provincetown’s beaches, restaurants, galleries and the energy of Commercial Street, yet tucked away enough to feel like a true escape. Whether you’re looking for a year-round residence, a weekend getaway or a Provincetown investment, this incredibly charming West End home captures everything there is to love about life at the tip of the Cape. Three bedrooms. Two baths. Private outdoor space. Coveted West End location. Pure Provincetown charm.
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: 684 sq ft (the lesser of 900 sq ft or half the 1,368 sq ft principal dwelling). Lot size: 2,490 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
Amenities & Appliances
Electric Water Heater • Range • Microwave • Refrigerator • Washer • Dryer
Neighborhood
Shopping • Other
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First22 x 13
Dining Room
Lvl First8 x 13
Kitchen
Lvl First7 x 8
Master Bedroom
Lvl Second15 x 13
Bedroom 2
Lvl Second9 x 12
Bedroom 3
Lvl Second12 x 8
Bathroom 1
Lvl First5 x 7
Bathroom 2
Lvl Second9 x 5
Property History
$1,849,000
Was $1,899,000
Sep 9, 2026
MLS® 73565795
$1,899,000
Aug 19, 2026
MLS® 73565795
Listing Agent: Lisa G. Loveland
Listing Office: Keller Williams Realty Boston-Metro | South End
MLS® Number: 73565795