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2 Heartbreak HillIpswich, MA 01938

For Sale

$3,575,000

Smart Buyer Rebate $17,875

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.

Listed by Paula Polo-Filias

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J. Barrett & Company

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978-479-0157

Listed by Lucy Pear

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J. Barrett & Company

Listed by Fabyan and Filias Team

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J. Barrett & Company

Last updated January 25, 2026

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Source: MLSPin #73470367

Listing Facts

  • TypeSingle-family
  • NeighborhoodIpswich
  • Bedrooms5
  • Bathrooms7
  • Days on Prevu10
  • Taxes$27,579.55/year
  • Size8,943 sqft
  • Price per sqft$400

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Air Conditioning
  • Parking
  • Swimming Pool

Location

Mortgage Calculator

Listing History

01/21/2026
Listed by J. Barrett & Company
$3,575,000

Property Details for 2 Heartbreak Hill

Association

Amenities

  • Community Features: Public Transportation, Shopping, Park, Walk/Jog Trails, Conservation Area, House Of Worship, Public School, T-Station

Exterior

Construction

  • Roof: Rubber
  • Window Features: Window(s) - Picture, Insulated Windows
  • Year Built: 1996
  • Year Built Details: Actual
  • Architectural Style: Contemporary
  • Construction Materials: Frame
  • Exterior Features: Porch, Deck, Deck - Roof, Deck - Wood, Deck - Composite, Pool - Inground Heated, Rain Gutters, Hot Tub/Spa, Greenhouse, Professional Landscaping, Sprinkler System, Decorative Lighting, Garden, Stone Wall

Features

  • Other Structures: Greenhouse
  • Patio And Porch Features: Deck - Exterior, Porch, Deck, Deck - Roof, Deck - Wood, Deck - Composite
  • Pool Features: Pool - Inground Heated, Indoor
  • Pool Private: Yes
  • Road Frontage Type: Private Road, Dead End
  • View: Scenic View(s)
  • Waterfront Features: Ocean, 1 To 2 Mile To Beach, Beach Ownership(Public)

Measurements

  • Building Area Total: 8,943
  • Building Area Units: Square Feet
  • Lot Features: Underground Storage Tank, Sloped
  • Lot Size Acres: 15.50
  • Lot Size Area: 15
  • Lot Size Square Feet: 675,180
  • Lot Size Units: Acres

Financial

Taxes

  • Tax Annual Amount: $27,579.55
  • Tax Assessed Value: $2,558,400.00
  • Tax Year: 2025

Interior

Features

  • Appliances: Water Heater, Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Water Treatment, Wine Refrigerator, Vacuum System, Range Hood, Plumbed For Ice Maker
  • Fireplace Features: Family Room, Kitchen, Living Room, Master Bedroom, Bedroom
  • Fireplace: Yes
  • Fireplaces Total: 5
  • Flooring: Wood, Tile, Carpet, Marble, Flooring - Stone/Ceramic Tile
  • Interior Features: Closet/Cabinets - Custom Built, Wet Bar, Bathroom - Full, Dining Area, Breakfast Bar / Nook, Open Floorplan, Vaulted Ceiling(s), Game Room, Office, Accessory Apt., Wine Cellar, Media Room, Central Vacuum, Wet Bar, Internet Available - Broadband
  • Spa Features: Private
  • Spa: Yes

Measurements

  • Living Area: 8,943
  • Living Area Source: Measured

Rooms

  • Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete
  • Bathrooms Full: 5
  • Bathrooms Half: 2
  • Bathrooms Total Integer: 7
  • Bedrooms Total: 5
  • Main Level Bedrooms: 1
  • Rooms Total: 19

Other

Environmental

  • Green Energy Efficient: Thermostat

Features

  • Accessibility Features: No

Location

  • Tax Block: 018C

Parking

Parking

  • Attached Garage: Yes
  • Covered Spaces: 6
  • Garage Spaces: 6
  • Garage: Yes
  • Open Parking Spaces: 8
  • Open Parking: Yes
  • Parking Features: Under, Garage Door Opener, Heated Garage, Storage, Garage Faces Side, Insulated, Oversized, Paved Drive, Shared Driveway, Off Street, Driveway, Paved
  • Parking Total: 14

Schools

Elementary School

  • Elementary School: Winthrop / Memorial

High School

  • High School: Ipswich High

Middle or Junior School

  • Middle Or Junior School: Ipswich Middle

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Electric: Generator, Generator Connection
  • Heating: Radiant, Oil, Fireplace
  • Has Heating: Yes
  • Laundry Features: Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Main Level, First Floor, Electric Dryer Hookup, Washer Hookup
  • Sewer: Private Sewer
  • Utilities: For Gas Range, For Electric Oven, For Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection
  • Water Source: Private

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 7 bathrooms in this single-family home at 2 Heartbreak Hill.

What schools are nearby to 2 Heartbreak Hill?

Nearby schools include the Winthrop / Memorial Elementary School, Ipswich Middle, and Ipswich High.

Does this single-family home have parking?

Yes, there are 6 parking spaces available for 2 Heartbreak Hill.

What are the annual taxes for 2 Heartbreak Hill?

Annual taxes for this single-family home are estimated at $27,579.

How does 2 Heartbreak Hill compare to other single-family homes in Ipswich?

This single-family home is listed 118% above the average price for single-family homes in Ipswich and has been on the market for 31 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 8,943 sqft.

2 Heartbreak Hill is a 5-bedroom, 7-bath single-family home for sale in Ipswich MA 01938. On Prevu for 10 days at $3,575,000. This residence features 8,943 square feet of living space, located in Ipswich. The median listing price for single-family homes in this area is $1,262,450. Nearby schools include Winthrop / Memorial Elementary School, Ipswich Middle, and Ipswich High. The home offers private outdoor space, dishwasher, air conditioning, parking, swimming pool, and washer/dryer. View other single-family home listings in Essex County.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.