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2 Heartbreak Hill, Ipswich MA 01938

Ipswich, MA 01938
$3,575,000
Est. $20,575/month
5
Beds
6
Baths
8,943
Sq Ft
$400
Price/Sq Ft
15.50
Acres
1996
Year Built
6 hours 57 minutes
Time on Market
Active Listed Jan 21, 2026 • MLS# 73470367 Copied!

About this home

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.

Property Overview

Property Type
Single Family Residence
Listing Type
For Sale
Year Built
1996
Bedrooms
5
Full Bathrooms
5
Half Bathrooms
2
Living Area
8,943 sq ft
Total Rooms
19
Main Level Bedrooms
1

Facts & Features

6 Car Garage
Central AC

Home Facts

Type Residential
Style Single Family Residence
Year Built 1996
Living Area 8,943 sq ft
Lot Size 15.50 acres
Bedrooms 5
Full Baths 5
Half Baths 2
Total Rooms 19

Interior

Heating Radiant, Oil, Fireplace
Cooling Central Air
Flooring Wood, Tile, Carpet, Marble, Flooring - Stone/ceramic Tile
Appliances Water Heater, Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Water Treatment, Wine Refrigerator, Vacuum System, Range Hood, Plumbed For Ice Maker
Fireplace Family Room, Kitchen, Living Room, Master Bedroom, Bedroom
Fireplaces 5
Basement Full, Partially Finished, Walk-out Access, Interior Entry, Concrete
Laundry Closet/cabinets - Custom Built, Flooring - Stone/ceramic Tile, Window(s) - Picture, Main Level, First Floor, Electric Dryer Hookup, Washer Hookup
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

Exterior

Construction Frame
Architecture Contemporary
Roof Rubber
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
Pool Pool - Inground Heated, Indoor
Spa Private
Fencing None
Patio/Porch Deck - Exterior, Porch, Deck, Deck - Roof, Deck - Wood, Deck - Composite

Parking

Garage Spaces 6
Has Garage Yes
Features Under, Garage Door Opener, Heated Garage, Storage, Garage Faces Side, Insulated, Oversized, Paved Drive, Shared Driveway, Off Street, Driveway, Paved
Total Spaces 14

Utilities

Electric Generator, Generator Connection
Water Private
Sewer Private Sewer
Gas None
Other For Gas Range, For Electric Oven, For Electric Dryer, Washer Hookup, Icemaker Connection, Generator Connection

Financial

Annual Tax $27,580
Assessed Value $2,558,400

Interior Features

Flooring: Wood, Tile, Carpet, Marble, Flooring - Stone/Ceramic Tile
Appliances: Water Heater, Range, Oven, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer, Water Treatment, Wine Refrigerator, Vacuum System, Range Hood, Plumbed For Ice Maker
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
Windows: Window(s) - Picture, Insulated Windows
Basement: Full, Partially Finished, Walk-Out Access, Interior Entry, Concrete
Laundry: Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Window(s) - Picture, Main Level, First Floor, Electric Dryer Hookup, Washer Hookup
Security: Security System

Construction & Materials

Style: Contemporary
Year Built: 1996
Structure Type:
Exterior Materials: Frame
Roof: Rubber
Foundation: Concrete Perimeter

Heating, Cooling & Utilities

Heating: Radiant, Oil, Fireplace
Heating Zones: 21
Cooling: Central Air
Cooling Zones: 7
Hot Water:
Water Source: Private
Sewer: Private Sewer
Energy Features: Thermostat

Exterior & Lot

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
Patio & Porch: Deck - Exterior, Porch, Deck, Deck - Roof, Deck - Wood, Deck - Composite
Fencing:
Other Structures: Greenhouse
Lot Features: Underground Storage Tank, Sloped
Road Surface:

Parking & Garage

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

Special Features

Fireplaces: 5
Fireplace Type: Family Room, Kitchen, Living Room, Master Bedroom, Bedroom
Pool: Private Pool
Pool Features: Pool - Inground Heated, Indoor
Spa/Hot Tub: Yes
Spa Features: Private
View: Yes
View Type: Scenic View(s)
Community Amenities: Public Transportation, Shopping, Park, Walk/Jog Trails, Conservation Area, House of Worship, Public School, T-Station

Location

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Neighborhood

2 Heartbreak Hill, Ipswich MA 01938

Ipswich, MA 01938

Walkability

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Nearby Schools

School District
Ipswich School District local
A-
School Safety 2024-25
0.9% Low
0.9% Suspensions 0.8% In-School
4.6% below state avg
E

Elementary Schools

2 schools
A-
Winthrop School
0.9 mi | #197 of 824 | Score: 55.2
Dropped 158 spots from last year
-3.1 below state avg
373 students Moderate
Strong Attendance
Grades PK-05
A
Paul F Doyon Memorial School
3.1 mi | #90 of 824 | Score: 59.8
Improved 33 spots from last year
+1.6 above state avg
366 students Moderate
Rising School Strong Attendance
Grades PK-05
M

Middle Schools

1 school
A-
Ipswich Middle School
1.8 mi | #93 of 352 | Score: 50.4
Improved 8 spots from last year
-7.8 below state avg
377 students Moderate
Strong Attendance
Grades 06-08
H

High Schools

1 school
A+
Ipswich High School
1.8 mi | #36 of 346 | Score: 69.6
Improved 26 spots from last year
+11.4 above state avg
447 students Moderate
19 sports • 1,184 athletes
Strong AP Program High Graduation Rate Rising School College Ready Curriculum
Grades 09-12
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Monthly Payment Calculator

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Including down payment
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Down: $0
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $2,298
Homeowners Insurance $200
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

Rate Impact

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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

Property History

Market Insights

40.2%
Price Range
1
Previous Sales

Property Timeline

🏠
Listed for Sale
Jan 21, 2026
$3,575,000
Original listing
Agent: Fabyan and Filias Team Office: J. Barrett & Company
Previous Transaction - MLS #73272739
Full transaction history available when tracking began
🏷️
Previously Sold
Jan 30, 2025
$2,137,500
MLS #73272739

Price & Status History

Date Event Price Change
Jan 21, 2026 New Listing Added $3,575,000
Jan 30, 2025 Sold $2,137,500

Market Statistics

Time on Market
6 hours 57 minutes
Price per Sq Ft
$400

Tax History

Year Taxes Assessment
2025 $27,580 $2,558,400

Financial Details

Annual Property Tax
$27,580
Tax Year 2025
Assessed Value
$2,558,400

Listing Information

Listing Agent Fabyan and Filias Team
Listing Office J. Barrett & Company
Agent MLS ID TM352682
Office MLS ID C95245
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.

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