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You are here:
Home Massachusetts Dedham Condos for Sale

165 Highland Street Dedham, MA 02026

65 Days on Boston Pads
Price Reduced $105,000
40 Photos
$995,000
2 Beds
2 Baths
1595 SQFT
Acres: N/A
$289 HOA
165 Highland Street
Dedham, MA 02026

Property Description

Recently converted into two condominiums, this historic property offers the convenience of condo living with the feel of a single-family home—perfect for downsizers, a single buyer seeking low-maintenance living, or a couple looking for their first home in desirable Precinct 1. Set on a private, landscaped lot, the home blends historic charm with modern updates and features seven rooms, including two bedrooms and one-and-a-half baths. The renovated kitchen includes marble countertops, stainless steel appliances, and a commercial-grade range, while a new primary bath and upgraded HVAC system provide year-round comfort. Enjoy a private yard framed by stone walls and lush greenery, offering a rare level of outdoor space and privacy for a condo. The unit also includes exclusive use of a large red barn with two bays—ideal for storage, a workshop, or a potential office or garage.

Property Overview

Kitchen, Dining, and Appliances

  • Kitchen Dimensions: 13'6"X29'10"
  • Kitchen Level: First Floor
  • Dishwasher, Dryer, Freezer, Microwave, Range, Refrigerator, Washer
  • Dining Room Dimensions: 11'11"X15'6"
  • Dining Room Level: First Floor
  • Dining Room Features: Fireplace, Flooring - Hardwood

Bedrooms

  • Bedrooms: 2
  • Master Bedroom Dimensions: 10'11"X13'1"
  • Master Bedroom Level: Second Floor
  • Bedroom 2 Dimensions: 9'1"X13'1"
  • Bedroom 2 Level: Second Floor

Other Rooms

  • Total Rooms: 6
  • Living Room Dimensions: 10'11"X15'6"
  • Living Room Level: First Floor
  • Living Room Features: Closet, Fireplace, Flooring - Hardwood
  • Family Room Dimensions: 11'8"X12'10"
  • Family Room Level: First Floor

Bathrooms

  • Full Baths: 1
  • Half Baths 1

Amenities

  • Amenities: Highway Access, Private School, Public School, Public Transportation, Shopping, Walk/Jog Trails
  • Association Fee Includes: Landscaping, Master Insurance, Snow Removal

Utilities

  • Heating: Central Heat, Forced Air, Gas
  • Heat Zones: 1
  • Cooling: Central Air
  • Electric Info: Circuit Breakers
  • Utility Connections: for Gas Dryer, for Gas Oven, for Gas Range
  • Water: City/Town Water
  • Sewer: Private Sewerage

Unit Features

  • Square Feet: 1595
  • Unit Building: 165
  • Unit Level: 1
  • Unit Placement: Ground
  • Interior Features: Security System
  • Security: Fenced
  • Floors: 2
  • Pets Allowed: No
  • Fireplaces: 2
  • Laundry Features: In Unit
  • Accessability Features: Unknown

Condo Complex Information

  • Condo Type: Condo
  • Complex Complete: U
  • Year Converted: 2025
  • Number of Units: 2
  • Elevator: No
  • Condo Association: U
  • HOA Fee: $289
  • Fee Interval: Monthly
  • Management: No Management

Construction

  • Year Built: 1700
  • Style: 2/3 Family
  • Construction Type: Frame
  • Roof Material: Asphalt/Fiberglass Shingles
  • Flooring Type: Hardwood, Tile, Wood
  • Lead Paint: Unknown
  • Warranty: No

Garage & Parking

  • Parking Features: Off-Street, Paved Driveway
  • Parking Spaces: 2

Exterior & Grounds

  • Exterior Features: Barn/Stable, Deck, Deck - Wood, Fenced Yard, Garden Area
  • Pool: No

Other Information

  • MLS ID# 73447152
  • Last Updated: 12/02/25
  • Documents on File: Master Deed, Other (See Remarks)

Date Event Price Price/Sq Ft Source
11/17/2025Active$995,000$624MLSPIN
11/13/2025Price Change$995,000$624MLSPIN
10/27/2025Active$1,100,000$690MLSPIN
10/23/2025New$1,100,000$690MLSPIN

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Map & Resources

Ursuline Academy

Private School, Grades: 7-12

0.1mi

Dedham Country Day School

Private School, Grades: PK-8

0.3mi

TGI Fridays

American Restaurant

0.44mi

Dedham Square Fire Station

Fire Station

0.53mi

Dedham Police Dept

Local Police

0.61mi

Planet Fitness

Fitness Centre

0.3mi

Town Of Dedham

Municipal Park

0.11mi

Star Market

Supermarket

0.37mi

Washington St opp Dedham Plaza

34E

0.25mi

Washington St @ Dedham Plaza

34E

0.26mi

Washington St @ Sylvia Ln

34E

0.31mi

Washington St @ Richards St

34E

0.32mi

Washington St @ Montague Rd

34E

0.32mi

Washington St @ Metcalf St

34E

0.33mi

525 Washington St opp Marion St

34E

0.35mi

Real Estate Resources

BayCoast Mortgage As a full-service lender providing industry-best solutions, BayCoast Mortgage can help make homeownership a reality for you. Want to get preapproved? Start today!
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Seller's Representative: Whitney Cheever, Hope McDermott Real Estate
MLS ID#: 73447152

© 2025 MLS Property Information Network, Inc.. All rights reserved.

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.

MLS PIN data last updated at 2025-12-02 11:33:00