37 Oakland St Wellesley — Photo 1 of 37
Recent Drop: $318,000
$2,280,000
Investment Analysis — 37 Oakland St
Wellesley, MA 02481
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 02481 carries an estimated $5,340/mo in gross rent — about a 1.64% cap rate and $37,301/yr in estimated NOI at the $2,280,000 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
4.5
SqFt
3,600
Style
Single Family
Built
2026
MAJOR $100,000 PRICE IMPROVEMENT—SELLER MOTIVATED! Stunning new-construction-quality renovation offering exceptional value in Wellesley. This completely gut-renovated 5BR/4.5BA home features a sun-filled open floor plan, designer finishes, and a chef's kitchen with premium appliances. Enjoy a bright sunroom, spacious living and entertaining areas, and a fully finished lower level perfect for a family room, gym, or guest suite. A professionally installed perimeter French drain system provides added peace of mind with a dry basement. Relax or entertain on the expansive deck overlooking the fully fenced backyard. Conveniently located near shopping, dining, parks, and the Mass Pike. Move-in ready with luxury finishes, modern systems, and incredible value. With a dramatic $100,000 price reduction, this is one of the best opportunities in today's Wellesley market. Schedule your showing today—this exceptional home is priced to sell and won't last!
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 3,600 sq ft principal dwelling). Lot size: 13,289 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.
Immersive Experience
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
Amenities & Appliances
Gas Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator
Neighborhood
Public Transportation • Shopping • Park • Walk/Jog Trails • Golf • Medical Facility
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,First14.7 x 19.6
Bathroom - Half, Closet, Flooring - Hardwood, Exterior Access, Open Floorplan, Recessed Lighting, Crown Molding
Dining Room
Lvl Main,First13.11 x 14.2
Flooring - Hardwood, Exterior Access, Open Floorplan, Recessed Lighting, Crown Molding
Kitchen
Lvl Main,First10.1 x 29.8
Flooring - Hardwood, Dining Area, Pantry, Countertops - Stone/Granite/Solid, Kitchen Island, Breakfast Bar / Nook, Exterior Access, High Speed Internet Hookup, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Gas Stove, Lighting - Pendant
Family Room
Lvl Main,First11.1 x 14.2
Flooring - Hardwood, Open Floorplan, Recessed Lighting, Crown Molding
Primary Bedroom
Lvl Second9.7 x 12.9
Bathroom - Full, Bathroom - Double Vanity/Sink, Closet - Linen, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Recessed Lighting, Crown Molding
Bedroom 2
Lvl Second12.7 x 13.9
Bedroom 3
Lvl Third12.6 x 13.9
Closet, Flooring - Hardwood, Recessed Lighting
Bedroom 4
Lvl Third13.1 x 17.4
Closet, Flooring - Hardwood, Recessed Lighting
Bedroom 5
Lvl Third12 x 12.1
Walk-In Closet(s), Flooring - Hardwood, Recessed Lighting
Bathroom 1
Lvl Main,First5.7 x 5.1
Bathroom - Half, Flooring - Stone/Ceramic Tile
Bathroom 2
Lvl Second9.7 x 12.9
Bathroom - Tiled With Shower Stall, Closet - Linen, Walk-In Closet(s), Flooring - Stone/Ceramic Tile, Double Vanity
Bathroom 3
Lvl Second8.7 x 8.1
Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Dryer Hookup - Electric, Washer Hookup
Property History
$2,598,000
Aug 31, 2026
MLS® 73518691
$2,280,000
Was $2,380,000
Aug 5, 2026
MLS® 73526041
$2,380,000
Was $2,480,000
Jul 16, 2026
MLS® 73526041
$2,480,000
Was $2,548,000
Jun 10, 2026
MLS® 73526041
$2,548,000
Was $2,598,000
Jun 3, 2026
MLS® 73526041
$2,598,000
May 28, 2026
MLS® 73526041
$2,598,000
May 14, 2026
MLS® 73518691
Listing Agent: John Saleh
Listing Office: Centre Realty Group
MLS® Number: 73526041
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