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12 Days on market
23 Longwood Dr Hopkinton — Photo 1 of 40

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.

View Standard Listing

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.

Open Houses

Property Details

Financials

Original Price$1,499,000
Annual Taxes$16,497

Parking

Garage3
Off-Street9

Interior Specifications

Total Rooms12
Fireplaces3
FlooringTile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Wall to Wall Carpet
BasementFull, Finished, Interior Entry, Bulkhead, Radon Remediation System

Climate & Utilities

HeatingBaseboard, Radiant, Heat Pump, Oil, Fireplace
CoolingCentral Air
WaterPrivate
SewerPrivate Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningA

Property & Lot

Acres1.41
SqFt Lot61,250
Lot FeaturesCorner Lot

Amenities & Appliances

Water Heater • Range • Oven • Dishwasher • Microwave • Refrigerator • Washer • Dryer

Neighborhood

Shopping • Walk/Jog Trails • Medical Facility • Public School • T-Station

Geography

Floorplan Breakdown

Structural Layout

Second
Primary BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
First
Living RoomDining RoomKitchenOfficeBathroom 1
Basement
Family Room
Living Room
Lvl First

Skylight, Cathedral Ceiling(s), Ceiling Fan(s), Flooring - Hardwood, French Doors

Dining Room
Lvl First

Flooring - Hardwood, French Doors, Wainscoting, Crown Molding

Kitchen
Lvl First

Flooring - Stone/Ceramic Tile, Pantry, Countertops - Stone/Granite/Solid, Breakfast Bar / Nook, Recessed Lighting, Lighting - Pendant

Office
Lvl First

Flooring - Hardwood, French Doors, Crown Molding

Family Room
Lvl Basement

Closet, Flooring - Wall to Wall Carpet, Recessed Lighting

Primary Bedroom
Lvl Second

Bathroom - Full, Ceiling Fan(s), Vaulted Ceiling(s), Walk-In Closet(s), Flooring - Hardwood, French Doors, Recessed Lighting, Lighting - Sconce

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Flooring - Hardwood, Attic Access, Recessed Lighting, Wainscoting, Closet - Double

Bedroom 4
Lvl Second

Flooring - Wall to Wall Carpet, Recessed Lighting, Closet - Double

Bathroom 1
Lvl First

Bathroom - Half, Flooring - Stone/Ceramic Tile, Wainscoting, Lighting - Sconce, Pedestal Sink

Bathroom 2
Lvl Second

Bathroom - 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 Second

Bathroom - 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

Listed
$1,499,000

Sep 1, 2026

MLS® 73570356

Expired
$1,499,000

Aug 31, 2026

MLS® 73537135

Listed
$1,499,000

Jun 17, 2026

MLS® 73537135

Listing Provided By

Listing Agent: The Macchi Group

Listing Office: William Raveis R.E. & Home Services

MLS® Number: 73570356