Active Under Contract
15 Days on market
151 Oakland Street Wellesley — Photo 1 of 42

151 Oakland Street Wellesley — Photo 1 of 42

$3,595,000

Investment Analysis — 151 Oakland Street

Wellesley, MA 02481

Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 6-bedroom in 02481 carries an estimated $5,340/mo in gross rent — about a 0.29% cap rate and $10,289/yr in estimated NOI at the $3,595,000 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

6

Baths

5

SqFt

6,525

Style

Single Family

Built

1748

Exquisite renovation of this distinctive property blends historic architectural character with sophisticated luxury living. Set on picturesque grounds with beautiful views of gardens, patios, the historic barn, golf course, and skyline vistas. Gracious, light-filled interiors feature hardwood floors, fireplaces, architectural detail, and beautiful views throughout. The sunny kitchen opens to a family room with gas fireplace, wet bar, and french doors to patio while the adjoining breakfast room/sunroom opens to a deck with sunrise views. A spacious great room with beamed ceilings and fireplace provides exceptional entertaining space. A first-floor office with separate entrance and full bath offers potential for an in-law/nanny suite. A wood paneled library with built-ins and a well-appointed dining room round out the first floor. Upstairs are five bedrooms, a sitting room/nursery, and four renovated baths. The third floor features a game room. The expansive lower level includes a recreation room, exercise room, workshop, mudroom, storage, and access to the two-car garage. A historic barn with electricity and water adds character and offers potential for an ADU. Convenient to Wellesley Hills shops, restaurants, commuter rail, and major routes, this exceptional property combines privacy, character, style, and remarkable views.

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 6,525 sq ft principal dwelling). Lot size: 50,212 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.

Open Houses

Property Details

Financials

Original Price$3,595,000
Annual Taxes$38,412

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms15
Fireplaces6
FlooringFlooring - Wood, Flooring - Wall to Wall Carpet
BasementFinished, Interior Entry, Garage Access

Climate & Utilities

HeatingForced Air, Natural Gas, Fireplace(s)
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

Construction--
Roof--
FoundationConcrete Perimeter, Brick/Mortar
ZoningSR-30

Property & Lot

Acres1.15
SqFt Lot50,212
Lot Features--

Neighborhood

Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Medical Facility

Geography

Floorplan Breakdown

Structural Layout

Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bedroom 5Bathroom 1Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenOfficeFamily Room
Living Room
Lvl First

Beamed Ceilings, Closet/Cabinets - Custom Built, Flooring - Hardwood

Dining Room
Lvl First

Flooring - Hardwood

Kitchen
Lvl First

Flooring - Hardwood, Recessed Lighting, Remodeled

Office
Lvl First

Closet, Recessed Lighting

Family Room
Lvl First

Flooring - Hardwood, Wet Bar, Exterior Access, Recessed Lighting, Remodeled

Master Bedroom
Lvl Second

Bathroom - Full, Walk-In Closet(s), Flooring - Hardwood, Recessed Lighting

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Bathroom - Full, Flooring - Hardwood, Recessed Lighting

Bedroom 4
Lvl Second

Flooring - Wall to Wall Carpet, Recessed Lighting

Bedroom 5
Lvl Second

Flooring - Wall to Wall Carpet, Recessed Lighting

Bathroom 1
Lvl Second

Bathroom - Double Vanity/Sink, Bathroom - With Tub & Shower, Remodeled

Bathroom 2
Lvl Second

Bathroom - Full, Bathroom - With Tub & Shower, Remodeled

Bathroom 3
Lvl Second

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - With Shower Stall, Remodeled

Property History

Listed
$3,595,000

Aug 28, 2026

MLS® 73569459

Terminated
$3,695,000

Aug 21, 2026

MLS® 73469127

Listed
$3,695,000

Jan 15, 2026

MLS® 73469127

Listing Provided By

Listing Agent: The Wilson Group

Listing Office: Compass

MLS® Number: 73569459