
23 Longwood Dr Hopkinton — Photo 1 of 40
$1,499,000
Investment Analysis — 23 Longwood Dr
Hopkinton, MA 01748
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 4-bedroom in 01748 carries an estimated $4,260/mo in gross rent — about a 1.49% cap rate and $22,354/yr in estimated NOI at the $1,499,000 list price. Adjust every assumption in the calculator below.
Beds
4
Baths
2.5
SqFt
4,836
Style
Single Family
Built
1993
On the shores of Lake Whitehall, in one of Hopkinton's most coveted and picturesque neighborhoods, this exceptional property offers an enviable lifestyle surrounded by miles of scenic trails, kayaking, fishing, boating, cross-country skiing, and winter ice skating, making outdoor recreation part of everyday life. Thoughtfully expanded and beautifully renovated for both entertaining and comfortable daily living, the heart of the home is a stunning chef's kitchen appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and generous gathering space. It flows effortlessly into what may become your favorite room in the house—a spectacular four-season sunroom featuring radiant heated floors, walls of windows, and a cozy gas fireplace. Whether you're savoring your morning coffee as the sun rises, admiring vibrant autumn foliage, or relaxing by the fire as snow falls outside, this space is magical in every season. The dramatic cathedral family room with a wood-burning fireplace creates a warm and inviting place to gather, while the formal dining room and private study offer timeless elegance and flexibility for today's lifestyle. The luxurious primary suite is a true retreat, featuring soaring ceilings, abundant natural light, a two-sided gas fireplace, and a spa-inspired bath with radiant heated floors and a soaking tub you'll never want to leave. Four additional generously sized bedrooms provide ample space for family, guests, or a second home office, while the finished lower level offers a spacious recreation room and dedicated fitness area. Designed for making memories, the outdoor living spaces are equally impressive. An expansive deck, beautiful stone patio, and inviting firepit overlook professionally landscaped grounds, creating the perfect setting for summer barbecues, evenings under the stars, and unforgettable gatherings with family and friends. Located just minutes from Hopkinton's highly rated schools, charming downtown, restaurants, shopping, the commuter rail, and major commuting routes, this home offers the perfect balance of luxury, convenience, and connection to nature. With both intimate, cozy spaces and an open floor plan designed for entertaining, you truly enjoy the best of both worlds. More than simply a beautiful home, 23 Longwood Drive is a place where every season brings something to enjoy, every room welcomes you to slow down, and every gathering becomes a cherished memory. This is a home that must be experienced in person.
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 4,836 sq ft principal dwelling). Lot size: 61,250 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.
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Water Heater • Range • Oven • Dishwasher • Microwave • Refrigerator • Washer • Dryer
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Floorplan Breakdown
Structural Layout
Living Room
Lvl FirstSkylight, Cathedral Ceiling(s), Ceiling Fan(s), Flooring - Hardwood, French Doors
Dining Room
Lvl FirstFlooring - Hardwood, French Doors, Wainscoting, Crown Molding
Kitchen
Lvl FirstFlooring - Stone/Ceramic Tile, Pantry, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Recessed Lighting, Lighting - Pendant
Office
Lvl FirstFlooring - Hardwood, French Doors, Crown Molding
Family Room
Lvl BasementCloset, Flooring - Wall to Wall Carpet, Recessed Lighting
Primary Bedroom
Lvl SecondBathroom - Full, Ceiling Fan(s), Vaulted Ceiling(s), Walk-In Closet(s), Flooring - Hardwood, French Doors, Recessed Lighting, Lighting - Sconce
Bedroom 2
Lvl SecondBedroom 3
Lvl SecondFlooring - Hardwood, Attic Access, Recessed Lighting, Wainscoting, Closet - Double
Bedroom 4
Lvl SecondFlooring - Wall to Wall Carpet, Recessed Lighting, Closet - Double
Bathroom 1
Lvl FirstBathroom - Half, Flooring - Stone/Ceramic Tile, Wainscoting, Lighting - Sconce, Pedestal Sink
Bathroom 2
Lvl SecondBathroom - Full, Bathroom - Tiled With Shower Stall, Fireplace, Skylight, Cathedral Ceiling(s), Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Jacuzzi / Whirlpool Soaking Tub, Double Vanity
Bathroom 3
Lvl SecondBathroom - Full, Bathroom - Tiled With Tub & Shower, Skylight, Cathedral Ceiling(s), Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Double Vanity, Lighting - Sconce, Lighting - Overhead
Property History
$1,499,000
Sep 1, 2026
MLS® 73570356
$1,499,000
Aug 31, 2026
MLS® 73537135
$1,499,000
Jun 17, 2026
MLS® 73537135
Listing Agent: The Macchi Group
Listing Office: William Raveis R.E. & Home Services
MLS® Number: 73570356