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Ad #7928192
MLS #5093138
Listing photo

Nestled in the heart of Portsmouth's coveted South End, just

395 Pleasant St, Portsmouth, NH 03801
$1,497,500
3Beds
2Baths
1,904Sqft
0.05Acres

About this property

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.

Property Features

3 Beds
2 Baths
1,904 Sqft
Built in 1795
0.05 Acres
2 Stories
Off Street
Siding: Clapboard Exterior
Shingle Roof
Has Fireplace
Forced Air, Natural Gas
$18,998 / yr property tax
Rockingham County

Additional Photos

Additional listing photo 1
Additional listing photo 2
Additional listing photo 3
Additional listing photo 4

Contact Information

Liz Levey-Pruyn

The Aland Realty Group, LLC

207-251-4762

Location

Map
Listing Agent: Liz Levey-Pruyn 207-251-4762
Broker: The Aland Realty Group, LLC 207-251-4762 Listing Site
Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.
BeachHouse.com
Printed Aug 12, 2026

Photo Gallery

Nestled in the heart of Portsmouth's coveted South End, just - photo 1
Nestled in the heart of Portsmouth's coveted South End, just - photo 2
Nestled in the heart of Portsmouth's coveted South End, just - photo 3
Nestled in the heart of Portsmouth's coveted South End, just - photo 4
Nestled in the heart of Portsmouth's coveted South End, just - photo 5
Nestled in the heart of Portsmouth's coveted South End, just - photo 6
Nestled in the heart of Portsmouth's coveted South End, just - photo 7
Nestled in the heart of Portsmouth's coveted South End, just - photo 8
Nestled in the heart of Portsmouth's coveted South End, just - photo 9
Nestled in the heart of Portsmouth's coveted South End, just - photo 10
Nestled in the heart of Portsmouth's coveted South End, just - photo 11
Nestled in the heart of Portsmouth's coveted South End, just - photo 12
Nestled in the heart of Portsmouth's coveted South End, just - photo 13
Nestled in the heart of Portsmouth's coveted South End, just - photo 14
Nestled in the heart of Portsmouth's coveted South End, just - photo 15
Nestled in the heart of Portsmouth's coveted South End, just - photo 16
Nestled in the heart of Portsmouth's coveted South End, just - photo 17
Nestled in the heart of Portsmouth's coveted South End, just - photo 18
Nestled in the heart of Portsmouth's coveted South End, just - photo 19
Nestled in the heart of Portsmouth's coveted South End, just - photo 20
Nestled in the heart of Portsmouth's coveted South End, just - photo 21
Nestled in the heart of Portsmouth's coveted South End, just - photo 22
Nestled in the heart of Portsmouth's coveted South End, just - photo 23
Nestled in the heart of Portsmouth's coveted South End, just - photo 24
Nestled in the heart of Portsmouth's coveted South End, just - photo 25
Nestled in the heart of Portsmouth's coveted South End, just - photo 26
Nestled in the heart of Portsmouth's coveted South End, just - photo 27
Nestled in the heart of Portsmouth's coveted South End, just - photo 28
Nestled in the heart of Portsmouth's coveted South End, just - photo 29
Nestled in the heart of Portsmouth's coveted South End, just - photo 30
Nestled in the heart of Portsmouth's coveted South End, just - photo 31
Nestled in the heart of Portsmouth's coveted South End, just - photo 32
Nestled in the heart of Portsmouth's coveted South End, just - photo 33
Nestled in the heart of Portsmouth's coveted South End, just - photo 34
Nestled in the heart of Portsmouth's coveted South End, just - photo 35
Nestled in the heart of Portsmouth's coveted South End, just - photo 36
Nestled in the heart of Portsmouth's coveted South End, just - photo 37
Nestled in the heart of Portsmouth's coveted South End, just - photo 38
Nestled in the heart of Portsmouth's coveted South End, just - photo 39
Nestled in the heart of Portsmouth's coveted South End, just - photo 40
Nestled in the heart of Portsmouth's coveted South End, just - photo 41
Nestled in the heart of Portsmouth's coveted South End, just - photo 42
Nestled in the heart of Portsmouth's coveted South End, just - photo 43
Nestled in the heart of Portsmouth's coveted South End, just - photo 44
Nestled in the heart of Portsmouth's coveted South End, just - photo 45
Nestled in the heart of Portsmouth's coveted South End, just - photo 46
Nestled in the heart of Portsmouth's coveted South End, just - photo 47
Nestled in the heart of Portsmouth's coveted South End, just - photo 48
Nestled in the heart of Portsmouth's coveted South End, just - photo 49
Nestled in the heart of Portsmouth's coveted South End, just - photo 50

$1,497,500

3
Beds
2
Baths
1,904
Sqft

395 Pleasant St, Portsmouth, NH 03801

By contacting this agent you agree to these Terms and Conditions.
Home New Hampshire Portsmouth
Nestled in the heart of Portsmouth's coveted South End, just - photo 1
Nestled in the heart of Portsmouth's coveted South End, just - photo 2
Nestled in the heart of Portsmouth's coveted South End, just - photo 3
Nestled in the heart of Portsmouth's coveted South End, just - photo 4
Nestled in the heart of Portsmouth's coveted South End, just - photo 5
MLS# 5093138
Home Active Under Contract

Nestled in the heart of Portsmouth's coveted South End, just

$1,497,500

395 Pleasant St, Portsmouth, NH 03801

3
Beds
2
Baths
1,904
Sqft
0.05
Acres
$1,497,500
395 Pleasant St, Portsmouth, NH 03801
3 Beds
2 Baths
1,904 Sqft
0.05 Acres
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.
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Property Details

HOME DETAILS

3 Beds
2 Baths
1,904 Sqft
Built in 1795
0.05 Acres
2 Stories

EXTERIOR

Off Street
Siding: Clapboard Exterior
Shingle Roof

INTERIOR

Has Fireplace
Forced Air, Natural Gas

FINANCIAL & COMMUNITY

$18,998 / yr property tax
Rockingham County
See More Details

Location

Map
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Ad Statistics

Ad Number
7928192
Viewed
0 time
Listing Status
Active Under Contract
Added
Jul 02, 2026
Last Refreshed
Jul 03, 2026 06:17:28 PM

Listing Information

Data Source
PrimeMLS
Source Property ID
5093138
Listing Agent: Liz Levey-Pruyn 207-251-4762
Broker: The Aland Realty Group, LLC 207-251-4762 Listing Site
Copyright © 2026 PrimeMLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Request Information

By proceeding, you authorize Dream Home Network Inc., its service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners), its affiliates, and other real estate professionals that may not be associated with Dream Home Network, to contact you using the contact details you provided, via email, phone call, and text (SMS), including using automated dialing technology and prerecorded and artificial voice, for marketing or advertising purposes, including contacting you about your inquiry and other home-related matters. You understand that your consent to the foregoing is not a condition of any purchase. Message and data rates may apply. This consent applies even if you are on a corporate, state or national Do Not Call list. Dream Home Network Inc. may share information about your recent and future site activity with its affiliates and service providers (including real estate professionals such as Brokers, Listing Agents, Buyers Agents, and local referral partners) to help them better understand what you are looking for in a property. To opt-out at any time you can reply "STOP" or contact Dream Home Network Inc. at csv@dreamhomenetwork.com.

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Dream Home Network Inc.

is committed to ensuring digital accessibility and property listings for individuals with disabilities. All information provided is deemed reliable but is not guaranteed and should be independently verified. We are continuously working to improve the accessibility of our web experience for everyone, and we welcome feedback and accommodation requests. If you wish to report an issue or seek an accommodation, please let us know.

Dream Home Network Inc. Sells leads to DHN Realty Inc. who holds real estate brokerage licenses in Alabama. Listing agents will be sent notification copy of leads on their listings where Dream Home Network Inc. is provided listings via our Feed Provider as required.

© 1997 - 2026 BeachHouse.com
Part of Dream Home Network, Inc.
Last updated on 2026.08.11
Terms & Policy