65 Leonard St, Gloucester, MA 01930
Property image
Property image
PENDING

$995,000

  • 2 Beds
  • 2 Baths
  • 1,902 sqft

65 Leonard St, Gloucester, MA 01930

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Home Highlights

Parking
2 Open Spaces
Outdoor
Porch, Patio
Price/Sqft
$523
Listed
97 days ago
Climate Control
Natural Gas, Baseboard Heating

Local Information

  • Map ViewExplore the area around 65 Leonard St.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

One of the oldest surviving homes in Annisquam, this historic First Period Colonial (circa 1717) is part of the property known as "The Old Castle." On Lobster Cove, this waterfront residence showcases a seasonal dock providing direct access. Located on the North Shore in Gloucester, the historic village of Annisquam offers a distinct coastal experience, distinguished by its narrow winding lanes, historic architecture, and a community atmosphere. Exceptional views are enjoyed both inside and out. Original craftsmanship has been preserved, including wide pine floors, woodwork, and two fireplaces. A sunroom along the water side was added and designed with three walls of full-length windows to watch the cove, with ample space for dining and multiple seating areas. The layout offers a bathroom on each floor, second-floor laundry, a back stairway, and third-floor bonus space. Practical updates include an updated heating system, replaced sunroom windows, basement work, and a repaired seawall.
Last check for updates: about 1 hour ago
Listing courtesy of John Farrell, (978) 578-5203
Coldwell Banker Realty - Beverly, (978) 927-1111
Source: MLS PIN, MLS#73521436
Also Listed on MLS PIN.

Home Details for 65 Leonard St

Interior Features

Interior Details
Basement: Interior Entry,Sump Pump,Concrete,UnfinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom 2, Master Bathroom, Bathroom 1, Bathroom 2, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 1902 Square FeetFoundation Area: 588
Appliances & Utilities
Utilities: for Electric RangeAppliances: Gas Water Heater, Water Heater, Range, Dishwasher, Refrigerator, Washer, DryerDishwasherDryerLaundry: Second FloorRefrigeratorWasher
Heating & Cooling
Heating: Baseboard,Natural GasNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Living Room, Master BedroomHas a FireplaceNo Spa
Gas & Electric
Electric: Circuit Breakers
Windows, Doors, Floors & Walls
Window: Skylight, Insulated WindowsFlooring: Wood, Tile, Carpet, Pine, Flooring - Wall to Wall Carpet, Flooring - Wood
Levels, Entrance, & Accessibility
Accessibility: NoFloors: Wood, Tile, Carpet, Pine, Flooring Wall To Wall Carpet, Flooring Wood
View
Has a ViewView: Scenic View(s), Water, Dock/Mooring, Harbor

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Porch, PatioExterior: Porch, Patio, Rain Gutters, Storage, GardenFoundation: Block, Stone, IrregularGarden
Parking & Garage
Open Parking Spaces: 2No GarageHas Open ParkingParking Spaces: 2Parking: Paved Drive,Off Street,Paved
Frontage
WaterfrontWaterfront: Waterfront, Navigable Water, Harbor, Dock/Mooring, Frontage, Walk to, Direct Access, Ocean, Beach Ownership(Private, Public)Road Frontage: PublicResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedOn Waterfront
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: 16.00
Finished Area
Finished Area (above surface): 1902

Days on Market

Days on Market: 97

Property Information

Year Built
Year Built: 1717
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Frame, Post & BeamAttached To Another StructureDoes Not Include Home Warranty
Property Information
Parcel Number: M:0121 B:0049 L:0000, 1899812

Price & Status

Price
List Price: $995,000Price Per Sqft: $523
Status Change & Dates
Off Market Date: Fri Aug 14 2026

Active Status

MLS Status: Under Agreement

Location

Direction & Address
City: Gloucester
School Information
Elementary School: Plum CoveJr High / Middle School: O'maley MsHigh School: Gloucester Hs

Agent Information

Listing Agent
Listing ID: 73521436

Building

Building Area
Building Area: 1902 Square Feet

Community

Community Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Stable(s), Golf, Medical Facility, Bike Path, Conservation Area, Marina, Private School, Public School, T-StationNot Senior Community

HOA

No HOA

Lot Information

Lot Area: 4500 sqft

Offer

Contingencies: Financing

Miscellaneous

BasementMls Number: 73521436Water ViewWater View: Dock/Mooring, Harbor, WaterAbove Grade Unfinished Area: 1902

Additional Information

Public TransportationShoppingPoolTennis Court(s)ParkWalk/Jog TrailsStable(s)GolfMedical FacilityBike PathConservation AreaMarinaPrivate SchoolPublic SchoolT-Station

Around this home

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.
  • Trulia User
    "There are a lot of dog and dog owners who live in the neighbor of lanesville Gloucester and seem very friendly "
    0
    Flag
  • Georgeanne H.
    "It's quite far from boston or shopping the winter travel is not easy and requires the utmost attention susceptible to morning fog on roads make for caution "
    13
    Flag
  • Megmcdnld
    "Have lived here on and off over many years. Sense of community is strong, lots of farmers markets and more sustainable living projects, kid friendly"
    4
    Flag
  • Lisa C.
    "Safe neighborhood to live in. We enjoy walks and the beach is near by. The school are great. It is a very quiet area."
    0
    Flag
  • Janellesousa
    "Gloucester has a great network of affordable daycare.there are many parks and beaches that my kids enjoy. There are also some great trails and quarries. There is a dog park up at stage fort park."
    2
    Flag
  • William M.
    "Pay attention to the random people in your neighborhood as it’s a close family environment so outsiders are easy to spot"
    4
    Flag
  • Charlotte T.
    "Dogs if all breeds are welcome in this town. There is a very accommodating dog park in town and the beaches are open to dogs in the off season "
    3
    Flag
  • Jennifer L.
    "I am visiting from Albany NY and it is absolutely beautiful here. The views are breathtaking & the air is so clean & fresh. The sound of the ocean is soothing & relaxing. I would love to call this place my home."
    1
    Flag
  • Geanoulis91297
    "Commute is very easy and accessible, there are many buses, taxis and a train near downtown. There’s a beach near where i live and i can walk to it too."
    1
    Flag
  • Gordonmichael3
    "This is a good area to have kids but currently very few living here(east Main Street) East Gloucester. A playground real close by with parents bringing children daily. "
    0
    Flag
  • Elizabeth G.
    "We have fiesta every summer, a carnival basically and a parade for the fellow Italians to rejoice, and those not Italian. We have concerts at the Fitz Hugh Lane house Thursday nights in the summer, and a lot of live entertainment. Beautiful seaside spot for good food, shops, historical landmarks, parks, beaches, etc. Much love for this town and the beauty behind it. "
    2
    Flag
  • Michael B.
    "if you live in gloucester, there is no reason to leave gloucester unless you need to travel for work, fortunately i work and live here. the island life is for me :)"
    0
    Flag
  • Jennifer S. W.
    "I live between long beach and Good harbor there are many fun events i enjoy almost all events i like biking hiking and just enjoying sunsets"
    1
    Flag
  • kim02128
    "I love this area, I am born/bred returned to live in Gloucester. This area is fantastic, great for walking and easy to get around without a car."
    0
    Flag
  • Jrharpy2
    "Nice neighbors, within minutes of everything and 1&1/2 blocks from the ocean. Kids have a paradise in the summer on Good Harbor beach. "
    0
    Flag
  • Kimberly V.
    "short and Easy, a short drive across town. it is typically 10 min without traffic, 20-30 during traffic hours."
    0
    Flag
  • Jrharpy2
    "Good Harbor beach is just around the corner, which is a paradise for kids in the summer and the back shore is spectacular at all times of the year."
    0
    Flag
  • Stefani H.
    "It is clean, quiet, free from traffic and near the beach bank post office hair salon dentist acupuncturist and convenient store"
    0
    Flag
  • Holly A.
    "this beautiful location has the oldest sea port in America with the oldest art colony in America. lots of history and lots of things to do and see"
    1
    Flag
  • Steffani L.
    "While I may have just moved to the neighborhood, many people there have been residents for quite some time. They are well known to each other, and I have watched and spoken to neighbors who verify this to be true."
    0
    Flag
  • Ms m.
    "quiet and friendly, lived here for 25 years. Good schools and coastal community with many good places to eat and picnic"
    0
    Flag

Market trends in Gloucester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$726K
Sale-to-List Price
99.9%
Price per sq ft
$449
Available listings
89
2MoM

Home Value

Trulia Estimate
$945K
Since last month
Decreased$119K (-11.2%)
Since last year
Decreased$550K (-36.8%)
Since last sale
Increased$631K (+202%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +5% in the last 10 years
MonthEstimated value
2026
August 2026$944K
July 2026$1.06M
June 2026$1.64M
April 2026$1.52M
March 2026$1.53M
February 2026$1.47M
January 2026$1.49M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
12 Hutchins Ct, Gloucester, MA
0.66
Single-Family Home
$535,000
10/06/25
2
2
1,074
6 River Rd, Gloucester, MA
0.29
Single-Family Home
$1,900,000
12/09/25
3
3.5
2,418
134-134R Leonard St, Gloucester, MA
0.39
Single-Family Home
$1,107,750
09/05/25
3
1.5
1,860
32 Holly St, Gloucester, MA
0.84
Single-Family Home
$895,900
09/30/25
3
2
1,920
27 Gee Ave, Gloucester, MA
1.20
Single-Family Home
$607,500
06/30/26
2
1
1,152
4 Lane Rd, Gloucester, MA
0.36
Single-Family Home
$1,700,000
10/15/25
3
3.5
3,882
49 Thurston Point Rd, Gloucester, MA
1.36
Single-Family Home
$1,150,000
12/17/25
2
2
1,518
188 Atlantic St, Gloucester, MA
1.19
Single-Family Home
$970,000
01/20/26
3
2
2,438
962 Washington St, Gloucester, MA
1.04
Single-Family Home
$815,000
12/01/25
3
2
2,036

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
53 Leonard St, Gloucester, MA 01930
0.04
$3,542,800
4
3.5
2,368
Off Market
37 Walnut St, Gloucester, MA 01930
0.10
$1,769,500
4
3
2,368
Off Market
1 Barberry Heights Rd, Gloucester, MA 01930
0.12
$821,400
3
2
1,790
Off Market
33 Leonard St, Gloucester, MA 01930
0.15
-
3
1
1,116
Off Market
25 Adams Hill Rd, Gloucester, MA 01930
0.19
$2,405,500
3
2.5
2,499
Off Market
121 Leonard St, Gloucester, MA 01930
0.28
$1,288,400
4
2
2,576
Off Market
19 Youngs Rd, Gloucester, MA 01930
0.31
$785,500
3
2
1,888
Off Market
6 River Rd, Gloucester, MA 01930
0.29
$1,900,000
3
3.5
2,418
Recently Sold
50 Norwood Hts, Gloucester, MA 01930
0.31
$3,626,100
4
3.5
3,246
Off Market
5 River Rd, Gloucester, MA 01930
0.30
$1,522,600
3
1.5
1,050
Off Market
15 Youngs Rd, Gloucester, MA 01930
0.35
$1,004,300
3
2
2,818
Off Market
4 Lane Rd, Gloucester, MA 01930
0.36
-
3
3.5
3,882
Off Market

Price and Tax history

DateEventPrice
Aug 15, 2026
Source: MLS PIN #73521436
Pending
$995,000
Aug 2, 2026
Source: MLS PIN #73521436
Contingent
$995,000
Aug 1, 2026
Source: MLS PIN #73521436
PriceChange
$995,000
Price decreased by 10%
Jul 24, 2026
Source: MLS PIN #73521436
PriceChange
$1,100,000
Price decreased by 4%
Jun 13, 2026
Source: MLS PIN #73521436
PriceChange
$1,150,000
Price decreased by 8%

LGBTQ Local Legal Protections

John Farrell, Coldwell Banker Realty - Beverly, (978) 927-1111
Agent Phone: (978) 578-5203
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.
The MLS listing information displayed is deemed reliable, but is not guaranteed accurate by the MLS.

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Frequently asked questions about 65 Leonard St

  • What is the estimated monthly payment for 65 Leonard St?
    Based on a $995,000 list price with 20% down at today's rates, the estimated monthly payment for 65 Leonard St in Gloucester, MA is approximately $6,090 (about $5,202 principal & interest, $813 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 65 Leonard St compare to homes in Gloucester?
    65 Leonard St in Gloucester, MA is listed at $995,000, about 37% above the $726K median sale price in Gloucester.
  • What do residents say about Gloucester?
    Residents describe Gloucester, MA as dog-friendly, well-kept, and pedestrian-friendly. See homes for sale in Gloucester, MA.
  • What are the closest schools to 65 Leonard St?
    The closest schools to 65 Leonard St in Gloucester, MA are Gloucester High School (rated 4/10), Plum Cove School (Elementary, rated 7/10), Ralph B O'Maley Innovation Middle School (rated 5/10).
  • Does 65 Leonard St have a pool?
    Yes, 65 Leonard St in Gloucester, MA has a pool.
  • Does 65 Leonard St have laundry facilities?
    Yes, 65 Leonard St in Gloucester, MA has in-unit laundry.
65 Leonard St, Gloucester, MA 01930 is a 2 bedroom, 2 bathroom, 1,902 sqft single-family home built in 1717. This property is currently available for sale and was listed by MLS PIN on May 19, 2026. The MLS # for this home is MLS# 73521436.