27 Highland St
Gloucester, MA 01930
- 3 Beds
- 3 Baths
- 2,270 sqft
3 Beds
3 Baths
2,270 sqft
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1881
Living Area
2,270 sqft
Price/Sqft
$499
About this House
This award-winning high-style antique w/ Italianate & Second Empire influences has been beautifully renovated in recent years including electric, heat, plumb, fixtures, furnace. Easy access to walking trails & ocean sails, ocean beaches (Good Harbor, Niles), Bass Rocks Golf Club & Harbor's vistas. Stroll to Gloucester Stage Co., North Shore Arts Association, Duckworth's Bistro & Rocky Neck Arts Colony w/ its acclaimed galleries & eateries. Open, gracious interior w/ over-sized windows & full southern exposure the length of the long side of house. Perfect for passive solar or solar panels. Marble fireplace, built-ins, moldings, pantries, medallions, many chandeliers. Master bdrm w/ antechamber & European tiled bath, plus another suite of 2 bedrooms w/ large bath/laundry. Natural gas heat, cooking & hot water is $2200/yr. Sunny organic gardens. Property has frontage on Plum St. where 4-5 additional off-street parking spaces can be easily added. 2 existing off-street front spaces.
27 Highland St, Gloucester, MA 01930 is a 3 bedroom, 3 bathroom, 2,270 sqft single-family home built in 1881. It last sold for $700,000 on Nov 24, 2020. It is currently off market. The Trulia Estimate is $1,131,600, with a rent estimate of $4,354/month.
Home Details for 27 Highland St
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Interior Details Basement |
Heating & Cooling Heating: Forced Air, GasHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2 |
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Exterior Home Features Roof: AsphaltExterior: Wood |
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Year Built Year Built: 1881 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 6969 sqft |
Price History for 27 Highland St
| Date | Price | Event | Source |
|---|---|---|---|
| 11/24/2020 | $700,000 | Sold | N/A |
| 07/23/2015 | $612,000 | Sold | N/A |
| 05/31/2015 | $619,000 | Pending | Agent Provided |
| 04/24/2015 | $619,000 | Listed For Sale | Agent Provided |
| 10/21/2014 | $619,000 | ListingRemoved | Agent Provided |
| 08/07/2014 | $619,000 | Listed For Sale | Agent Provided |
| 10/27/2013 | $619,000 | ListingRemoved | Agent Provided |
| 08/30/2013 | $619,000 | PriceChange | Agent Provided |
| 07/25/2013 | $639,000 | Listed For Sale | Agent Provided |
| 09/28/2000 | $251,355 | Sold | N/A |
| 08/25/1992 | $105,000 | Sold | N/A |
Market trends in Gloucester
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
91
6MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $8,935 |
| Assessment | $918,300 |
Home facts updated by county records
Comparable Sales for 27 Highland St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.08 | Single-Family Home | $990,000 | 06/05/26 | 3 | 1.5 | 2,560 | |
0.14 | Single-Family Home | $626,500 | 11/05/25 | 3 | 1 | 1,574 | |
0.21 | Single-Family Home | $1,250,000 | 09/26/25 | 4 | 2.5 | 2,556 | |
0.24 | Single-Family Home | $790,000 | 06/15/26 | 4 | 2 | 2,700 | |
0.44 | Single-Family Home | $725,000 | 08/28/25 | 4 | 4 | 2,063 | |
0.18 | Single-Family Home | $1,015,000 | 06/01/26 | 2 | 3.5 | 2,678 | |
0.32 | Single-Family Home | $1,125,000 | 01/30/26 | 4 | 3.5 | 2,724 | |
0.39 | Single-Family Home | $810,000 | 01/28/26 | 2 | 2 | 1,548 | |
0.33 | Single-Family Home | $675,000 | 10/17/25 | 4 | 2 | 1,889 | |
0.54 | Single-Family Home | $755,000 | 01/05/26 | 4 | 2 | 2,021 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 27 Highland St.
What Locals Say about Gloucester
At least 179 Trulia users voted on each feature.
88 % Say it's dog friendly
82 % Say people would walk alone at night
72 % Say yards are well-kept
72 % Say there's holiday spirit
71 % Say car is needed
68 % Say there are sidewalks
68 % Say there's wildlife
68 % Say parking is easy
65 % Say neighbors are friendly
64 % Say streets are well-lit
62 % Say it's walkable to restaurants
60 % Say they plan to stay for at least 5 years
60 % Say kids play outside
59 % Say it's walkable to grocery stores
52 % Say it's quiet
46 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Apartments for Rent
Homes for sale near 27 Highland St
Off Market Homes Near 27 Highland St
Frequently asked questions about 27 Highland St
- What is 27 Highland St estimated to be worth?Trulia's estimated value for 27 Highland St in Gloucester, MA is $1,131,600.
- What is the price history for 27 Highland St?27 Highland St in Gloucester, MA last sold for $700,000 in November 2020.
- Is Gloucester a buyer's or seller's market?Gloucester is currently a seller's market, based on recent for-sale activity.
- What do residents say about Gloucester?Residents describe Gloucester, MA as dog-friendly, well-kept, and pedestrian-friendly. See recently sold homes in Gloucester, MA.
- How big is the lot at 27 Highland St?The lot at 27 Highland St in Gloucester, MA is about 0.16 acres (6,969 sq ft).

