395 Pleasant Street, Portsmouth, NH, 03801 | $1,497,500

Nestled in the heart of Portsmouth’s coveted South End, just moments from Prescott Park, Strawbery Banke, downtown Portsmouth, and the waterfront, this lovingly restored c. 1795 center-chimney Colonial blends timeless character with thoughtful updates. Rich in historic charm, this exceptional home has been maintained and thoughtfully updated while preserving its original woodwork, floor plan, and architectural integrity. Built by Benjamin Holmes, a joiner whose craftsmanship likely included the lovely moldings, the home showcases wide pine floors, fireplaces, and period details that have been carefully preserved to maintain its historic character while accommodating modern living. An inviting pocket garden creates a private outdoor retreat while providing efficient off-street parking and exceptional curb appeal. At the heart of the home, the chef’s kitchen features an exposed chimney with intricate brickwork & beehive oven, creating a striking architectural focal point. Modern amenities include a gas range, wall oven, custom cabinetry, & soapstone sink. The formal living room is richly detailed with double crown moldings, a chair rail, elegant ceiling medallion, & one of four working fireplaces, with a carved mantel and marble hearth. The dining room continues the home’s architectural story with dentil molding, an original mantelpiece, and distinctive gunstock corners. A 1st office with custom built-ins provides an ideal space for remote work or study. The first-floor half bath with laundry includes a stainless-steel utility sink, blending practicality with period charm. The 2nd floor offers three bedrooms & a full bath, while both front & rear staircases enhance functionality and historic character. The unfinished third floor provides generous storage & potential for future expansion. A rare opportunity to own a beautifully maintained piece of Portsmouth history in one of the city’s most sought-after neighborhoods.

Features

  • Rooms: 7
  • Bedrooms: 3
  • Baths: 1 full / 1 half
  • Style: Antique,Colonial
  • Year Built: 1795
  • Heating: Natural Gas,Forced Air
  • Cooling: None
  • Basement: Unfinished,Basement Stairs
  • Approx Sq. Feet: 1,904
  • Acreage: 0.05
  • Est. Taxes: $18,998
  • Lot Desc: City Lot,Corner,Landscaped,Level,Sidewalks,In Town
  • Elem. School: Little Harbor School
  • Middle School: Portsmouth Middle School
  • High School: Portsmouth High School
  • School District: Portsmouth School District
  • MLS#: 5093138
  • Website: https://www.raveis.com
    /eprop/5093138/395pleasantstreet_portsmouth_nh?source=qrflyer
©2026 New England Real Estate Network, Inc. All rights reserved.This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimMLS. The information being provided is 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 7/28/2026
Listing courtesy of The Aland Realty Group   Phone: 603-501-0463
Listing Agent: Liz Levey-Pruyn

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Frank KolbSenior Vice President - Coaching & Strategic, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 81725

203.980.8025

Frank.Kolb@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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Our Insurance Division:

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395 Pleasant Street, Portsmouth, NH, 03801

$1,497,500

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Frank Kolb

Senior Vice President - Coaching & Strategic

William Raveis Mortgage, LLC

Phone: 203.980.8025

Frank.Kolb@raveis.com

NMLS Mortgage Loan Originator ID 81725

5/6 (30 Yr)
Adjustable Rate Jumbo*
30 Year
Fixed-Rate Jumbo
15 Year
Fixed-Rate Jumbo
Loan Amount $1,198,000 $1,198,000 $1,198,000
Term 360 months 360 months 180 months
Initial Interest Rate** 5.500% 6.250% 6.000%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.165% 6.361% 6.183%
Monthly Tax Payment $1,583 $1,583 $1,583
H/O Insurance Payment $125 $125 $125
Initial Principal & Interest Pmt $6,802 $7,376 $10,109
Total Monthly Payment $8,510 $9,084 $11,817

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.