Listed by Duston Leddy Real Estate · Eric Brassard · Phone: 323-717-9199

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Condominium · Portsmouth, NH

ActiveFor Sale

108 Pleasant Street, Portsmouth, NH

$1,875,000

Est. $9,481/mo · 20% down, 30-yr, 6.5% (Owl’s Nest Real Estate estimate, not MLS data)

Beds
3
Baths
4
Sq Ft
1,635
Built
1797
MLS®
#5112480

Property Description

Offered at $1,875,000, this Portsmouth condominium at 108 Pleasant Street pairs New Hampshire living with everyday convenience. It counts 3 bedrooms, 4 bathrooms and 1,635 square feet of living space. Condos in this corridor are the low-maintenance way into the market — association-managed exteriors, shared amenities and predictable monthly costs. Beyond the basics, the listing carries a 0.08-acre lot, 1797 construction and roughly $1,147 per square foot. Everything below — photos, details, schools and market data — updates live from the MLS.

Welcome to The Joseph Sherburne Ayers House (built in 1797), set on coveted Pleasant Street in the heart of downtown Portsmouth. Thoughtfully restored from the ground up in 2021, the property showcases exceptional craftsmanship at every turn. Many of the home’s original details have been preserved and the layout, systems, and finishes have been updated to meet with modern taste, luxury, and convenience. Often referred to as the Pumpkin House, the unique, L-shaped building provides for deeded off-street parking and a private backyard patio. Out front, historically-protected sightlines ensure the wash of generations of sunlight into all of the homes living spaces. The 2 unit HOA provides for condominium convenience (landscaping, snow removal) with the privacy of single-family living. Inside, the home’s original beams highlight the modern kitchen and living spaces and each of the 3 generously sized en suite bedrooms across the home’s two upper floors. Carefully selected finishes, elevated design, and meticulous attention to detail define every space. The home’s gracious proportions and historic charm are complemented by a beautifully appointed interior designed for both effortless entertaining and everyday living. The result is a rare balance of authenticity and contemporary luxury; an inviting residence with a sense of permanence, polish, and place.

Location Highlights

108 Pleasant Street is a condominium in Portsmouth, New Hampshire, listed at $1,875,000. That works out to about $1,147 per square foot, for a home built in 1797. It has been on the market for 5 weeks.

At this latitude, Portsmouth averages roughly 8.4 hours of sun a day in June and 3.6 in December.

Zoned schools in the Portsmouth: Little Harbor School (Elementary), Portsmouth Middle School (Middle), Portsmouth (High). Always confirm zoning with the district office.

Source: zoned school names are PrimeMLS listing data; distances, sun exposure and school facts are Owl’s Nest Real Estate additions (school facts from the NCES, U.S. Department of Education) — not PrimeMLS data.

Property Details

Essentials & finishes

Bedrooms
3
Total Baths
4
Full Baths
1
SqFt
1,635
Price / SqFt
$1146.79
Property Type
Condominium
Year Built
1797
County
NH-Rockingham
Town
Portsmouth, NH
Status
Active
Days on Market
15

Primary Features

County
NH-Rockingham
Property Type
Residential
Year Built
1797
Zoning
CD-L1

Interior Features

Appliances
Dishwasher, Dryer, Microwave, Gas Range, Washer, Vented Exhaust Fan, Water Heater
Basement
Yes
Basement Access Type
Interior
Basement Description
Concrete Floor, Full, Interior Entry, Interior Stairs, Storage Space, Unfinished, Basement Stairs
1/4 Baths
0
3/4 Baths
2
Cooling
Central Air
Electric
200+ Amp Service
Flooring
Hardwood
Heating
Hot Air
Interior Features
2 Fireplaces, Kitchen Island, Primary BR w/ BA, Natural Light, Vaulted Ceiling(s), 2nd Floor Laundry
Rooms - Total
9
SqFt-Approximate Finished Above Grade
1,635
SqFt-Approximate Finished Below Grade
0
SqFt Approximate Total Finished
1,635
SqFt Approximate Total
2,180

Location Information

School - District
Portsmouth
School - Elementary
Little Harbor School
School - High
Portsmouth
School - Middle/Jr
Portsmouth Middle School

Financial Details

Association Fee
$400
Fee Frequency
Monthly
Fee Includes
Landscaping, Plowing
Tax - Gross Amount
$14,985
Tax Year
2026
Taxes TBD
No

Additional

Construction Status
Existing
Construction
Wood Frame, Wood Exterior, Wood Siding
Covenants
No
Easements
No
Flood Zone
No
Pre-Construction
No
Property Sub Type
Condominium
Seasonal
No
Total Stories
3
Surveyed
Yes
Timeshare/Fractional Ownership
No

External Features

Color
Orange
Driveway
Common/Shared, Paved
Exterior Features
Patio
Foundation
Fieldstone, Poured Concrete
Garage
No
Lot Features
Corner Lot, Landscaped, Level, In Town, Near Shopping, Near School(s)
Lot - Acres
0.08
Lot - SqFt
3,485
Parking
Driveway, Off Street, On Site, Parking Spaces 1, Paved
Road Frontage Type
Public
Road Frontage
Yes
Road Frontage Length
110
Roof
Architectural Shingle
Sewer
Public
Utilities
Cable, Underground Gas
Water Source
Public

MLS®: PrimeMLS #5112480; Listed by Duston Leddy Real Estate · Eric Brassard · Phone: 323-717-9199

Property History

Estimated annual taxes for this property

2024
$31,875
2023
$31,078
2022
$30,281

Source: Owl’s Nest Real Estate estimate from the list price at New Hampshire’s average effective tax rate — not PrimeMLS or town assessor data. Verify with the town assessor.

Market Data

Live snapshot computed by Owl’s Nest Real Estate from PrimeMLS IDX active listings in this town

Active listings in Portsmouth
124
Average list price
$1,181,117
Price range
$425,000 – $2,775,000

Mortgage Calculator

Estimate your monthly payment for this home

Loan Term

Estimated Monthly Payment

$12,528/ mo

Principal & Interest
$9,481
Property Tax
$2,656
Home Insurance
$391

Source: Owl’s Nest Real Estate estimate, not PrimeMLS data. Estimates use typical New Hampshire costs — a 1.7% effective property-tax rate, insurance at 0.25% of home value/yr, and PMI below 20% down. Actual town tax rates vary; verify with your lender and the town assessor.

Around This Property

Schools, everyday places and nearby destinations near 108 Pleasant Street, Portsmouth, NH

Assigned Schools

Elementary
Little Harbor School
Middle
Portsmouth Middle School
High School
Portsmouth
District
Portsmouth

Source: Google Maps Platform (Places) and Owl’s Nest Real Estate — not PrimeMLS data.

Questions About This Listing

How much does 108 Pleasant Street cost?

108 Pleasant Street in Portsmouth, NH is listed for $1,875,000 on PrimeMLS.

That is about $1,147 per square foot of finished living space.

It came on the market on October 1, 2026.

How many bedrooms and bathrooms does 108 Pleasant Street have?

108 Pleasant Street in Portsmouth, NH has 3 bedrooms and 4 bathrooms (1 full, 2 three-quarter and 1 half) in 1,635 square feet of finished living space.

What type of home is 108 Pleasant Street?

108 Pleasant Street in Portsmouth, NH is a condominium built in 1797.

The MLS lists its style as Colonial, with three stories.

What town is 108 Pleasant Street in?

108 Pleasant Street is in Portsmouth, New Hampshire 03801, in Rockingham County.

Location notes from the MLS: in town, near shopping and near school(s).

What is the lot size of 108 Pleasant Street?

108 Pleasant Street in Portsmouth, NH sits on 0.08 acres, per the MLS.

The lot is described as corner lot, landscaped and level.

It has 110 feet of road frontage (public).

Zoning: CD-L1.

The MLS says the lot has been surveyed.

The MLS lists it as outside a flood zone.

What are the annual property taxes for 108 Pleasant Street?

Annual property taxes on 108 Pleasant Street in Portsmouth, NH are $14,985 for the 2026 tax year, per the MLS.

New Hampshire towns set their own tax rates and revalue periodically, so confirm the current bill with the Portsmouth assessing office.

What are the association fees for 108 Pleasant Street?

The association fee for 108 Pleasant Street in Portsmouth, NH is $400 (monthly), per the MLS.

The MLS lists the fee as covering landscaping and plowing.

Ask for the association documents and budget to see exactly what the fee covers.

What heating and cooling does 108 Pleasant Street have?

108 Pleasant Street in Portsmouth, NH is heated by hot air, per the MLS.

Cooling: central air.

What are the water and sewer systems at 108 Pleasant Street?

108 Pleasant Street in Portsmouth, NH has public water and public sewer, per the MLS.

MLS details — water: public; sewer: public.

Electric: 200+ amp service.

Other utilities: cable and underground gas.

Does 108 Pleasant Street have a basement?

Yes. 108 Pleasant Street in Portsmouth, NH has a basement with interior access.

The MLS describes it as concrete floor, full, interior entry, interior stairs, storage space, unfinished and basement stairs.

What are the key features of 108 Pleasant Street?

Inside, the MLS lists these features at 108 Pleasant Street in Portsmouth, NH: 2 fireplaces, kitchen island, primary BR w/ BA, natural light, vaulted ceiling(s) and 2nd floor laundry.

Outside: patio.

Flooring: hardwood.

Listed appliances: dishwasher, dryer, microwave, gas range, washer, vented exhaust fan and water heater; confirm which ones convey in the purchase agreement.

What parking does 108 Pleasant Street have?

The MLS lists no garage at 108 Pleasant Street in Portsmouth, NH; parking is off a common/shared and paved driveway.

Parking details: driveway, off street, on site, parking spaces 1 and paved.

What school district is 108 Pleasant Street in?

The MLS places 108 Pleasant Street in Portsmouth, NH in the Portsmouth school district.

Listed schools: Little Harbor School (elementary), Portsmouth Middle School (middle) and Portsmouth (high).

School assignments can change; confirm with the district.

Is 108 Pleasant Street still for sale?

Yes. 108 Pleasant Street in Portsmouth, NH is listed as Active on PrimeMLS (MLS #5112480).

Status can change quickly; contact us to confirm availability before you visit.

Which brokerage has 108 Pleasant Street listed?

108 Pleasant Street in Portsmouth, NH is listed by Eric Brassard of Duston Leddy Real Estate (603-610-8285).

Owl's Nest Real Estate shows it through the PrimeMLS IDX feed; we are not the listing brokerage.

How does the price of 108 Pleasant Street compare with other Portsmouth listings?

At $1,875,000, 108 Pleasant Street in Portsmouth, NH is priced above the $659,900 median asking price of the 69 condos for sale in Portsmouth on PrimeMLS as of November 3, 2026 (this listing included).

That figure is Owl's Nest Real Estate's analysis of active listings, and asking prices are not sale prices — ask us for recent comparable sales before you make an offer.

How can I see 108 Pleasant Street in person?

To see 108 Pleasant Street in Portsmouth, NH, use Request a Showing on this page or call Owl's Nest Real Estate at 401-648-5308.

We can show any MLS-listed home and represent you as your buyer's agent; the listing brokerage represents the seller.

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This listing data is intended for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 11/03/26.