55 Parkwood Drive Milton — Photo 1 of 41
$5,995,000
Investment Analysis — 55 Parkwood Drive
Milton, MA 02186
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 7-bedroom in 02186 carries an estimated $3,390/mo in gross rent — about a -0.12% cap rate and $-7,311/yr in estimated NOI at the $5,995,000 list price. Adjust every assumption in the calculator below.
Beds
7
Baths
8.5
SqFt
9,320
Style
Single Family
Built
1915
Experience the pinnacle of Milton living at this 1915 French Colonial masterpiece. Set on nearly three acres at the foot of the Blue Hills Reservation, this legacy estate offers a rare blend of privacy and prestige. The grounds are an entertainer’s dream, featuring an in-ground pool, pool house, and a two-story, five-bay garage with an attached vintage greenhouse. Spanning 9,000+ sq. ft., the residence boasts seven bedrooms, ten bathrooms, and nine fireplaces. The main level offers grand formal spaces, including a mahogany-paneled library and a sophisticated office. The chef’s culinary suite is a masterwork of marble and high-end gas ranges. Retreat to the palatial primary wing—a four-room haven with dual baths and expansive views. The finished lower level adds versatility with twin fitness studios and a private lounge and office. Located eight miles from Boston and Logan, enjoy a country-manor lifestyle near world-class Milton Academy. A rare architectural gem. Welcome home!
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 9,320 sq ft principal dwelling). Lot size: 120,661 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
Gas Water Heater • Range • Oven • Dishwasher • Disposal • Trash Compactor • Microwave • Indoor Grill • Refrigerator • Washer • Dryer • Range Hood
Neighborhood
Pool • Medical Facility • Bike Path • Conservation Area • Highway Access • House of Worship
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl Main,First17 x 15
Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting
Dining Room
Lvl Main,First20 x 17
Flooring - Hardwood, French Doors, Recessed Lighting
Kitchen
Lvl Main,First38 x 22
Bathroom - Half, Flooring - Stone/Ceramic Tile, Dining Area, Countertops - Stone/Granite/Solid, Deck - Exterior, Recessed Lighting, Stainless Steel Appliances
Office
Lvl First15 x 15
Fireplace, Flooring - Hardwood, Recessed Lighting
Family Room
Lvl Main,First23 x 20
Flooring - Stone/Ceramic Tile, Cable Hookup, Recessed Lighting
Primary Bedroom
Lvl Second20 x 16
Bathroom - Full, Flooring - Hardwood, Deck - Exterior, Recessed Lighting
Bedroom 2
Lvl Second18 x 15
Bedroom 3
Lvl Third13 x 10
Closet, Flooring - Wall to Wall Carpet, Recessed Lighting
Bedroom 4
Lvl Third23 x 17
Closet, Flooring - Hardwood
Bedroom 5
Lvl Third20 x 15
Fireplace, Closet, Flooring - Hardwood
Bathroom 1
Lvl SecondBathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub
Bathroom 2
Lvl SecondBathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub
Bathroom 3
Lvl ThirdBathroom - Full, Bathroom - Tiled With Tub & Shower, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub, Recessed Lighting
Property History
$5,995,000
May 15, 2026
MLS® 73519804
$5,995,000
Nov 29, 2025
MLS® 73397591
$5,995,000
Jun 27, 2025
MLS® 73397591
Listing Agent: Kevin G. Keating
Listing Office: Keating Brokerage
MLS® Number: 73519804
