Get Natick and Metrowest Listings and Market Information

Work with Robb Enterprises real estate to buy, sell, or lease property that is right for you

  • Properties
    • For Rent
    • For Sale
    • Vacation Rental
    • Commercial
  • Specialty Properties
    • Natick New Construction
    • Natick Waterfront
    • Apartments for Rent in Natick MA 01760
    • Section 8 Advertised Properties
  • Agents
  • Compare
  • Blog
  • Contact Us

Properties

  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
  • 2 Heartbreak Hill, Ipswich, Massachusetts, 5 Bedrooms Bedrooms, 19 Rooms Rooms,6 BathroomsBathrooms,Residential,For Sale,Heartbreak Hill,73470367
Property Description

This striking modern estate rises above 15+ acres of complete privacy, with sweeping overland views and distant ocean vistas. Designed for both drama and livability, the move-in-ready contemporary centers around a breathtaking great room with 25-foot ceilings, walls of glass, and an elevated bridge overlooking the space. The home flows effortlessly into a sleek chef’s kitchen, sophisticated media and billiard rooms, and multiple guest suites ideal for hosting. Five bedrooms, seven baths, and a remarkable home office or studio complete the main residence. A spectacular natatorium—with a 50-foot heated pool and spa, bar, and private guest suite, creates a true year-round resort experience. The second-floor primary suite offers a marble spa bath and custom dressing room, while a lower-level library/office and wine cellar cater to collectors and remote work. Expansive decks extend living outdoors, and the approach—via koi pond, waterfalls, and tranquil landscaping, an unforgettable estate.

Features
Swimming Pool:
Indoor, Pool - Inground Heated
Heating System:
Oil, Radiant, Fireplace
Cooling System:
Central Air
Basement:
Full, Partially Finished, Walk-out Access, Interior Entry, Concrete
Fireplace:
Family Room, Master Bedroom, Living Room, Bedroom, Kitchen
Security:
Security System
Parking:
Under, Garage Door Opener, Heated Garage, Storage, Garage Faces Side, Off Street, Paved, Paved Drive, Oversized, Insulated, Driveway, Shared Driveway
Appliances:
Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer, Freezer, Vacuum System, Water Treatment, Range Hood, Plumbed For Ice Maker, Oven, Water Heater, Wine Refrigerator
Construction:
Frame
Exterior Unit Features:
Professional Landscaping, Deck, Porch, Pool - Inground Heated, Hot Tub/spa, Decorative Lighting, Sprinkler System, Deck - Wood, Deck - Roof, Stone Wall, Deck - Composite, Greenhouse, Rain Gutters, Garden
Flooring:
Tile, Wood, Marble, Carpet, Flooring - Stone/ceramic Tile
Sewer:
Private Sewer
Style:
Contemporary
Water:
Private
Disclosure:
Sellers are owners of Listing Brokerage.
Electric Feature:
Generator, Generator Connection
Garage Parking:
6
Interior Features:
Central Vacuum, Internet Available - Broadband, Closet/cabinets - Custom Built, Wet Bar, Media Room, Game Room, Bathroom - Full, Office, Open Floorplan, Breakfast Bar / Nook, Vaulted Ceiling(s), Accessory Apt., Dining Area, Wine Cellar
Lead Paint:
No
Waterview Features:
Ocean
Laundry Features:
Washer Hookup, First Floor, Flooring - Stone/ceramic Tile, Main Level, Electric Dryer Hookup, Closet/cabinets - Custom Built, Window(s) - Picture
Additional Information
Grade School:
Winthrop / Memorial
High School:
Ipswich High
Middle School:
Ipswich Middle
Market Time:
4
Parking Spaces:
14
Tax Year:
2025
Status:
Active
Price Per Sqft:
$400
Zoning:
RRA
Orig Price:
$3,575,000
Fireplaces:
5
Waterfront:
No
MlsStatus:
Active
Address Map
City:
Ipswich
State:
MA
County:
Essex
Postal Code:
01938
Longitude:
W71° 10' 29.3''
Latitude:
N42° 40' 23.1''
  • Google Map

Residential

2 Heartbreak Hill, Ipswich, Massachusetts

5 Bedrooms
6 Total Bathrooms
8,943 Sqft
$3,575,000
Listing ID #73470367
Basic Details
Property Type :
Residential
Listing Type :
For Sale
Price :
$3,575,000
View :
Scenic View(s)
Bedrooms :
5
Rooms :
19
Total Bathrooms :
6
Full Bathrooms :
5
Half Bathrooms :
2
Square Footage :
8,943 Sqft
Year Built :
1996
Lot Area :
15.50 Acre
Listing ID :
73470367
  • Share on Facebook
  • Share on Twitter
  • Share on Pinterest
  • PDF
  • Send to Friend
  • Request a Visit
Agent info
Robb Enterprises
  • Stephen E. Robb
  • View website
  • 617-212-0251
  • srobb@robbenterprises.com

Contact Agent

The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information are for the personal, non commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.

Similar Properties

Residential

Residential

70 East Street, Ipswich, Massachusetts

More
Residential

Residential

59 South Main St, Ipswich, Massachusetts

More
45 County St, Ipswich, Massachusetts, 1 Bedroom Bedrooms, 3 Rooms Rooms,1 BathroomBathrooms,Residential,For Sale,County St,73467875

Residential

45 County St, Ipswich, Massachusetts

More
500 Colonial Drive, Ipswich, Massachusetts, 1 Bedroom Bedrooms, 4 Rooms Rooms,1 BathroomBathrooms,Residential,For Sale,Colonial Drive,73467142

Residential

500 Colonial Drive, Ipswich, Massachusetts

More
11 Washington Street, Ipswich, Massachusetts, 3 Bedrooms Bedrooms, 7 Rooms Rooms,3.5 BathroomsBathrooms,Residential,For Sale,Washington Street,73462480

Residential

11 Washington Street, Ipswich, Massachusetts

More
57 East Street, Ipswich, Massachusetts, 2 Bedrooms Bedrooms, 8 Rooms Rooms,1.5 BathroomsBathrooms,Residential,For Sale,East Street,73460420

Residential

57 East Street, Ipswich, Massachusetts

More
Residential

Residential

6 Mayfair Ct, Ipswich, Massachusetts

More
15 Eagle Hill Rd, Ipswich, Massachusetts, 3 Bedrooms Bedrooms, 5 Rooms Rooms,1 BathroomBathrooms,Residential,For Sale,Eagle Hill Rd,73451461

Residential

15 Eagle Hill Rd, Ipswich, Massachusetts

More
Realtyna

Copyright © 2026