Active
52 Days on market
16 Longmeadow Rd Milton — Photo 1 of 41

16 Longmeadow Rd Milton — Photo 1 of 41

Recent Drop: $205,000

$3,500,000
$3,295,000

$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.

View Standard Listing

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

Original Price$3,500,000
Annual Taxes$30,008

Parking

Garage3
Off-Street9

Interior Specifications

Total Rooms12
Fireplaces2
FlooringWood, Tile, Carpet, Hardwood, Flooring - Wall to Wall Carpet, Flooring - Hardwood
BasementFull, Interior Entry, Bulkhead, Concrete, Unfinished

Climate & Utilities

HeatingBaseboard, Oil
CoolingCentral Air
WaterPublic, Private
SewerPublic Sewer

Building & Exterior

ConstructionFrame, Brick
RoofShingle
FoundationConcrete Perimeter
ZoningRA

Property & Lot

Acres0.92
SqFt Lot40,036
Lot Features--

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

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

16 x 21

Flooring - Hardwood, Wet Bar, Pocket Door

Dining Room
Lvl First

15 x 15

Flooring - Hardwood, French Doors, Wainscoting, Pocket Door

Kitchen
Lvl First

29 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 First

9 x 9

Family Room
Lvl First

22 x 17

Flooring - Hardwood, Tray Ceiling(s), Window Seat

Master Bedroom
Lvl Second

18 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,First

18 x 18

Bedroom 3
Lvl Second

16 x 17

Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wall to Wall Carpet

Bedroom 4
Lvl Second

15 x 12

Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Wall to Wall Carpet

Bedroom 5
Lvl Second

15 x 12

Closet/Cabinets - Custom Built, Flooring - Wall to Wall Carpet

Bathroom 1
Lvl Second

11 x 7

Bathroom - Double Vanity/Sink, Closet - Linen, Flooring - Marble, Hot Tub / Spa, Steam / Sauna

Bathroom 2
Lvl Second

8 x 14

Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Closet - Linen

Bathroom 3
Lvl First

10 x 6

Bathroom - Full, Bathroom - Tiled With Tub & Shower

Property History

Price Drop
$3,295,000

Was $3,500,000

Aug 6, 2026

MLS® 73553103

Listed
$3,500,000

Jul 22, 2026

MLS® 73553103

Listing Provided By

Listing Agent: Emily Edwards

Listing Office: Gibson Sotheby's International Realty

MLS® Number: 73553103