
16 Longmeadow Rd Milton — Photo 1 of 41
Recent Drop: $205,000
$3,295,000
Investment Analysis — 16 Longmeadow Rd
Milton, MA 02186
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 02186 carries an estimated $3,390/mo in gross rent — about a 0.03% cap rate and $909/yr in estimated NOI at the $3,295,000 list price. Adjust every assumption in the calculator below.
Beds
5
Baths
4.5
SqFt
5,700
Style
Single Family
Built
1994
Welcome to 16 Longmeadow Road, a custom-built masterpiece showcasing exceptional architectural detail at every turn. A dramatic two-story foyer with grand staircase and soaring ceilings sets the tone for this five-bedroom, four-and-a-half-bath residence in the highly sought-after Indian Cliffs Estates. The luxurious primary suite spans 500 square feet and features a spa-inspired ensuite with whirlpool tub, steam shower, and dual walk-in closets. The gourmet eat-in kitchen is a chef's dream, with a center island featuring a gas stove, dual sinks, and French doors flooded with natural light—flowing seamlessly into the formal dining room and sophisticated lounge complete with fireplace and wet bar, creating an entertainer's paradise. An additional living room with 11-foot tray ceiling, fireplace, and custom media cabinetry offers the perfect retreat. The home features a guest suite with separate entrance—ideal for an au pair, multi-generational living, or a private office sanctuary. Throughout, five walk-in closets, multiple linen closets, and a cedar closet provide unparalleled storage. The three-car garage and expansive rear patio with private well irrigation complete this exceptional property. Situated on nearly one acre and just 300 yards from Wollaston Golf Club, this residence offers both privacy and prestige.
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 5,700 sq ft principal dwelling). Lot size: 40,036 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
Water Heater • Oven • Dishwasher • Disposal • Trash Compactor • Range • Refrigerator • Freezer • Washer • Dryer
Neighborhood
Pool • Tennis Court(s) • Walk/Jog Trails • Golf • Medical Facility • Conservation Area
Geography
Floorplan Breakdown
Structural Layout
Living Room
Lvl First16 x 21
Flooring - Hardwood, Wet Bar, Pocket Door
Dining Room
Lvl First15 x 15
Flooring - Hardwood, French Doors, Wainscoting, Pocket Door
Kitchen
Lvl First29 x 25
Vaulted Ceiling(s), Closet, Flooring - Stone/Ceramic Tile, Dining Area, Pantry, Countertops - Stone/Granite/Solid, French Doors, Kitchen Island, Breakfast Bar / Nook, Gas Stove
Office
Lvl First9 x 9
Family Room
Lvl First22 x 17
Flooring - Hardwood, Tray Ceiling(s), Window Seat
Master Bedroom
Lvl Second18 x 22
Bathroom - Full, Bathroom - Double Vanity/Sink, Walk-In Closet(s), Flooring - Wall to Wall Carpet, Dressing Room, Closet - Double, Tray Ceiling(s)
Bedroom 2
Lvl Main,First18 x 18
Bedroom 3
Lvl Second16 x 17
Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wall to Wall Carpet
Bedroom 4
Lvl Second15 x 12
Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wall to Wall Carpet
Bedroom 5
Lvl Second15 x 12
Closet/Cabinets - Custom Built, Flooring - Wall to Wall Carpet
Bathroom 1
Lvl Second11 x 7
Bathroom - Double Vanity/Sink, Closet - Linen, Flooring - Marble, Hot Tub / Spa, Steam / Sauna
Bathroom 2
Lvl Second8 x 14
Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Closet - Linen
Bathroom 3
Lvl First10 x 6
Bathroom - Full, Bathroom - Tiled With Tub & Shower
Property History
$3,295,000
Was $3,500,000
Aug 6, 2026
MLS® 73553103
$3,500,000
Jul 22, 2026
MLS® 73553103
Listing Agent: Emily Edwards
Listing Office: Gibson Sotheby's International Realty
MLS® Number: 73553103
