55 days on market
$249,900
88 Aylwin Rd
Portsmouth, Virginia 23702
MLS# 10629825 · CRADOCK · Portsmouth VA
Updated yesterday · Source: REIN MLS
Est. payment
$1,634/mo
Edit below
Price / sq ft
$156
1,602 sq ft
Days on market
55
HOA
None
Year built
1940
86 yrs old
Beds
3
Full Baths
1
Half Baths
0
Sq Ft
1,602
Garage
Yes
Schools
- ElementaryCradock Elementary School3/10
- MiddleCradock Middle School3/10
- 2/10
Info provided by GreatSchools
About this home
Change your life with this three-bedroom home in Portsmouth, VA, offering a practical layout and comfortable everyday living. Bright living spaces and a functional kitchen make this home both efficient and easy to enjoy. The bedrooms offer flexibility for guests or a home office. Outside, enjoy a private yard and a location near shopping, dining, interstates, and military bases. A strong option for a primary residenc…
Listed by Jordan Williams · KW Coastal Virginia Chesapeake
VaHome Team property overview
Meet 88 Aylwin Road — a 1940-built, 3-bedroom home in Portsmouth's historic Cradock neighborhood, sitting on a generous 0.39-acre lot. With 1,602 square feet of living space and classic architectural character, this address offers room to breathe in one of Hampton Roads' most storied communities.
Read full property overview ↓Show less ↑
Why this home stands out
What sets 88 Aylwin Road apart is the combination of a nearly half-acre lot and a pre-war home with genuine architectural bones — something increasingly rare in an urban Portsmouth setting. Cradock was purpose-built as a planned community in the early 20th century, and that intentional design still shows in the wide lots, mature trees, and cohesive streetscapes. You're getting real land, real history, and a single-family footprint that gives you options most comparable addresses simply can't match.
CRADOCK and the Portsmouth real estate market
Cradock is one of the most distinctive neighborhoods in all of Hampton Roads. Developed in the early 1920s as a planned community for shipyard workers, it was designed with an uncommon level of care — curving streets, generous setbacks, and a neighborhood layout that still feels purposeful a century later. The homes here reflect that era, and 88 Aylwin Road fits right in with its 1940 construction and traditional form. Portsmouth itself is a city with deep roots in American naval history, positioned along the Southern Branch of the Elizabeth River and bordered by Norfolk, Chesapeake, and Suffolk. The primary keyword for this address is Portsmouth historic home for sale, and it fits naturally here: buyers searching for character-rich properties in Portsmouth consistently find Cradock near the top of the list. The city offers a walkable downtown waterfront, a growing arts scene, and some of the most affordable entry points into homeownership in the entire Hampton Roads metro.
What's nearby
Daily life is well-supported from 88 Aylwin Road. Grocery options, pharmacies, and everyday retail are within a short drive along the High Street and Frederick Boulevard corridors. Cradock's own commercial strip adds neighborhood-scale convenience close to home. For green space, Cavalier Manor Park and the broader Portsmouth park system are accessible without a long commute. The Elizabeth River Trail connects Portsmouth to Norfolk via a waterfront path that's become a regional favorite for cyclists and walkers alike. Downtown Portsmouth's Olde Towne district — with its restaurants, coffee shops, and waterfront boardwalk — is just a few miles north and worth the short drive on any given evening.
For different buyers
For military families relocating
Dam Neck Annex is roughly 15 minutes away, and NAS Oceana sits about 21 minutes out — both very manageable for daily commutes. Portsmouth has long been a practical choice for military households, and a VA loan is a natural fit for this type of single-family purchase. The 0.39-acre lot gives a family real outdoor space, and Cradock's stable, established neighborhood character makes it easy to feel at home between duty stations.
For buyers drawn to character
If you're drawn to homes with a real story, 88 Aylwin Road delivers. Built in 1940 inside a planned community that dates to the 1920s, this address carries the kind of architectural authenticity that newer construction simply can't replicate. Cradock's streetscape is a living piece of American urban planning history, and a nearly half-acre lot gives you the outdoor canvas to complement whatever vision you bring to the interior.
Frequently asked questions
How far is 88 Aylwin Road from Dam Neck Annex?
Dam Neck Annex is approximately 15 minutes from 88 Aylwin Road under typical traffic conditions, making it one of the more convenient addresses in Portsmouth for personnel assigned there. The route primarily runs via I-264 East toward Virginia Beach.
What is the Cradock neighborhood like in Portsmouth?
Cradock is a historic planned community developed in the early 1920s, featuring curving streets, mature trees, and homes built largely between 1920 and 1950. It has a strong neighborhood identity, active civic associations, and a character that distinguishes it from most other Portsmouth neighborhoods.
How far is 88 Aylwin Road from NAS Oceana?
NAS Oceana is about 21 minutes from this address, accessible via I-264 East into Virginia Beach. That commute is well within the range most military households in the Hampton Roads area consider reasonable.
Is 88 Aylwin Road in a flood zone?
Flood zone information for this address is displayed in the dedicated FloodRisk tile on this page, which pulls current FEMA map data. We recommend reviewing that section and consulting with your lender or insurance agent for specifics.
What can you tell me about the lot size at 88 Aylwin Road?
The lot measures 0.39 acres — just under a half acre — which is notably large for an in-city Portsmouth address. That kind of outdoor space gives you real flexibility for gardening, entertaining, or simply having a backyard that doesn't feel cramped.
Curious about 88 Aylwin Road or other homes in Cradock? Tom and Dariya Milan at LPT Realty know this market well — reach out and let's talk through what fits your situation.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Places within ~1 mile, ordered by distance from this property. Powered by Google Places.
Flood Risk
Property Details
Bedrooms
3
Full Baths
1
Half Baths
0
Approx Sq Ft
1,602
Stories
2
Fireplaces
0
Flooring
Carpet, Wood
Heating
Radiator
Cooling
Window/Wall
Laundry
Interior Features
Pull Down Attic Stairs, Walk-In Closet
Appliances
Dishwasher, Dryer, Gas Range, Refrigerator, Washer
Sale & Tax History
List Price
$249,900
Price / Sq Ft
$156
Annual Taxes
$3,172
Monthly Tax
$264
HOA
None
Tax Rate (effective)
1.27%
Sale Timeline (this listing)
| Event | Date | Price | Detail |
|---|---|---|---|
| Listed | Apr 14, 2026 | $249,900 | — |
| Currently listed | — | $249,900 | — |
Looking for multi-year tax assessments or prior sales? REIN MLS only ships data for the current listing. For full property history, check the city assessor record:
Tax data above from REIN public-records sync. Sale timeline tracked from this listing's first appearance in our feed forward; prior owner sales are not included.
Comparable Properties
Comps are selected by city, bed count, square footage and price proximity. Composite similarity score weights bed match, sqft variance, price variance, and straight-line distance.
About buying in Portsmouth
Homes for sale in Portsmouth, VA combine historic charm with the most affordable entry prices in Hampton Roads. Olde Towne Portsmouth (23704) features cobblestone streets and Federalist-era row houses overlooking the Elizabeth River, with active listings typically ranging $250K-$500K. Western Portsmouth's Churchland neighborhood (23703) offers larger suburban homes, top schools, and direct commutes to Norfolk Naval Shipyard. Park View (23707) and Cradock (23702) provide some of the most affordable single-family inventory in the region, often under $200K. Portsmouth's biggest employers are Norfolk Naval Shipyard (one of the largest ship-repair facilities in the country) and Naval Medical Center Portsmouth — Hampton Roads' largest military hospital. Active-duty military and shipyard families make up a significant share of buyers, and VA loan financing is common. Portsmouth Public Schools includes Churchland High, Manor High, and I.C. Norcom High; Churchland is consistently among the city's top-performing high schools. Buyers looking for waterfront views without Virginia Beach prices often find Portsmouth's Olde Towne and Hodges Ferry areas particularly attractive. Browse every active Portsmouth listing below, refreshed every 5 minutes from the REIN MLS.
Military Commute
Drive times to nearest basesDrive times via Google Maps with current traffic patterns. Times are typical and may vary by time of day. Use the "Analyze" button up top to see live drive time to your saved base.
Estimate your monthly payment
$1,634/moPrincipal & interest
$1,297
Property tax
$264
Home insurance
$73
PMI
None
HOA
None
Estimate only. Insurance assumed at 0.35% of home value annually. Actual taxes, insurance, and rate will vary by lender, credit, and property. Contact a lender for a personalized quote.
Listed by KW Coastal Virginia Chesapeake · MLS# 10629825
Data provided by REIN MLS. Information deemed reliable but not guaranteed.
$249,900
88 Aylwin RD, PORTSMOUTH VA 23702
Portsmouth, Virginia 23702
Request InfoQuick Facts
Schedule a tour
In-person or videoClick a day to pick a time