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165 Highland Street 165Dedham, MA 02026

For Sale

$995,000

Smart Buyer Rebate $4,975

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.

Listed by Whitney Cheever

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Hope McDermott Real Estate

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917-573-7719

Last updated December 02, 2025

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Source: MLSPin #73447152

Listing Facts

  • TypeCondo
  • NeighborhoodDexter
  • Bedrooms2
  • Bathrooms2
  • Days on Prevu50
  • HOA/Maint. Fees$289/month
  • Size1,595 sqft
  • Price per sqft$624

Amenities

  • Dishwasher
  • Private Outdoor Space
  • Washer/Dryer
  • Pets Allowed
  • Air Conditioning
  • Parking

Location

Mortgage Calculator

Listing History

11/13/2025
Price Decreased
$995,000
10/23/2025
Listed by Hope McDermott Real Estate
$1,100,000

Property Details for 165 Highland Street 165

Association

Amenities

  • Community Features: Public Transportation, Shopping, Walk/Jog Trails, Highway Access, Private School, Public School
  • Pets Allowed: Yes w/ Restrictions

Fees

  • Association Fee: $289.00 Monthly
  • Association Fee Includes: Insurance, Maintenance Grounds, Snow Removal

Exterior

Construction

  • Number Of Units Total: 2
  • Roof: Shingle
  • Stories: 2
  • Stories Total: 2
  • Structure Type: 2/3 Family
  • Year Built: 1700
  • Year Built Details: Approximate
  • Construction Materials: Frame
  • Entry Level: 1
  • Entry Location: Unit Placement(Ground)
  • Exterior Features: Deck, Deck - Wood, Barn/Stable, Fenced Yard, Garden

Features

  • Fencing: Security, Fenced
  • Other Structures: Barn/Stable
  • Patio And Porch Features: Deck, Deck - Wood

Measurements

  • Building Area Total: 1,595
  • Building Area Units: Square Feet
  • Lot Size Units: Acres

Financial

Taxes

  • Tax Year: 2025

Interior

Features

  • Appliances: Range, Dishwasher, Microwave, Refrigerator, Freezer, Washer, Dryer
  • Fireplace Features: Dining Room, Living Room
  • Fireplace: Yes
  • Fireplaces Total: 2
  • Flooring: Wood, Tile, Hardwood
  • Interior Features: Home Office

Measurements

  • Living Area: 1,595
  • Living Area Source: Owner

Rooms

  • Basement: Y
  • Bathrooms Full: 1
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 2
  • Rooms Total: 6

Parking

Parking

  • Open Parking Spaces: 2
  • Open Parking: Yes
  • Parking Features: Off Street, Paved
  • Parking Total: 2

Schools

Elementary School

  • Elementary School: Riverdale

High School

  • High School: Dedham

Middle or Junior School

  • Middle Or Junior School: Dedham

Utilities

Equipment

  • Cooling: Central Air
  • Has Cooling: Yes
  • Electric: Circuit Breakers
  • Heating: Central, Forced Air, Natural Gas
  • Has Heating: Yes
  • Laundry Features: In Unit, Gas Dryer Hookup
  • Sewer: Private Sewer
  • Utilities: For Gas Range, For Gas Oven, For Gas Dryer
  • Water Source: Public

Frequently Asked Questions

How many bedrooms and bathrooms does this condo have?

There are 2 bedrooms and 2 bathrooms in this condo at 165 Highland Street 165.

What schools are nearby to 165 Highland Street 165?

Nearby schools include the Riverdale Elementary School, Dedham Middle School, and Dedham High School.

Does this condo have parking?

Yes, there are 2 parking spaces available for 165 Highland Street 165.

Are pets allowed at 165 Highland Street?

Yes, 165 Highland Street allows pets. Check the Property Details for any relevant restrictions.

How does 165 Highland Street 165 compare to other condos in Dexter?

This condo is listed 30% below the average price for condos in Dexter and has been on the market for 26 less days than the typical home in this area.

What is the square footage on this condo?

According to the MLS, this listing is 1,595 sqft.

165 Highland Street 165 is a 2-bedroom, 2-bath condo for sale in Dedham MA 02026. Available on Prevu for 50 days at $995,000. This includes a recent price decrease of $105,000. This residence features 1,595 square feet of living space, located in Dexter. The median listing price for condos in this area is $2,550,000. Nearby schools include Riverdale Elementary School, Dedham Middle School, and Dedham High School. Additional amenities include private outdoor space, dishwasher, pets allowed, air conditioning, parking, and washer/dryer. Browse more condo listings in Norfolk 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.