35 days on market
$249,900
88 Aylwin Rd
Portsmouth, Virginia 23702
MLS# 10629825 · CRADOCK · Portsmouth VA
Updated 6 days ago · Source: REIN MLS
Est. payment
$1,634/mo
Edit below
Price / sq ft
$156
1,602 sq ft
Days on market
35
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
88 Aylwin Road is 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. Character, space, and a well-established community come together at this address.
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 classic 1940s build in one of Portsmouth's most architecturally cohesive neighborhoods. Lots this size are genuinely rare inside an established urban neighborhood, giving you room to breathe, garden, or simply enjoy outdoor space that newer developments rarely offer at this scale.
CRADOCK and the Portsmouth real estate market
Cradock is one of the most distinctive neighborhoods in all of Portsmouth — and that's not a casual claim. Developed in the early 1920s as a planned community for World War I shipyard workers, it retains a rare sense of architectural unity, with brick and frame homes lining tree-canopied streets in a grid that feels intentional rather than accidental. The neighborhood sits in the southern reaches of Portsmouth, a city that rewards those who look past the surface. Portsmouth has its own waterfront, its own downtown arts district, and a genuine small-city identity that larger neighbors can't replicate. Residents here tend to stay, and the neighborhood association keeps a watchful eye on the area's character. While you might search online for gloucester county homes for sale or explore other Hampton Roads communities, Cradock has a specific gravitational pull — the kind of place where neighbors know each other and the streets feel lived-in in the best possible way. The 23702 zip code places you well within reach of the broader South Hampton Roads metro.
What's nearby
Daily life is easy from 88 Aylwin Road. Grocery options are within a short drive, and the broader Portsmouth commercial corridor along Frederick Boulevard covers most everyday errands. Elizabeth River Trail access points are close by for cyclists and walkers. The Cradock Branch Library is just minutes away. Portsmouth's Olde Towne Historic District — one of the largest collections of 18th and 19th-century architecture on the East Coast — is a short drive north. Interstate 264 and the Downtown Tunnel put Norfolk, Virginia Beach, and Chesapeake all within practical reach for work or weekend plans.
For different buyers
For military families relocating
Dam Neck Annex is roughly 15 minutes away, and NAS Oceana sits about 21 minutes out — both well within a comfortable commute window. VA loan eligibility can make a home like this especially accessible, and BAH rates for the Hampton Roads area are structured with neighborhoods like Cradock in mind. The lot size gives military families room for a vegetable garden, play space, or simply a yard worth coming home to.
For buyers drawn to character
If you've been searching for a home with genuine bones — not a flipped spec house or a cookie-cutter build — 88 Aylwin Road delivers. The 1940 construction era means real plaster walls, solid framing, and proportions that modern builders rarely replicate. Cradock itself is a living piece of American urban planning history, and owning here means you're part of a neighborhood that has actively preserved its identity for over a century.
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. The route generally runs via I-264 East toward Virginia Beach.
How far is 88 Aylwin Road from NAS Oceana?
NAS Oceana is about 21 minutes away, making it a manageable daily commute for personnel stationed there. Virginia Beach Boulevard and I-264 are the primary route options.
What is the Cradock neighborhood known for?
Cradock is a nationally recognized planned community developed in the early 1920s, known for its architectural consistency, brick-lined streets, and strong neighborhood identity within Portsmouth, Virginia.
Is 88 Aylwin Road in a flood zone?
Flood zone designation for this address should be verified through FEMA's official flood map service or confirmed during the due-diligence period of any transaction — check the FloodRisk tile on this page for current FEMA data.
Does 88 Aylwin Road have an HOA?
Cradock does have an active civic league and neighborhood association, but whether a formal HOA with mandatory dues applies to this specific address should be confirmed through a title search or the seller's disclosure.
Want to walk the lot or talk through what a 1940s Cradock home means structurally and financially? Tom and Dariya Milan at LPT Realty know this neighborhood well — reach out and let's talk.
Summary generated by AI from public records and publicly available information.
Location & Neighborhood
Location & Street View
88 Aylwin RD, Portsmouth
Map and Street View imagery © Google. Imagery may not be current.
Map data ©Google. Click and drag inside the map to explore the surrounding area.
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
Portsmouth combines historic naval heritage with affordable, character-rich neighborhoods. Olde Towne Portsmouth offers tree-lined streets of restored 18th- and 19th-century homes with sweeping Elizabeth River views — one of the largest collections of pre-Revolutionary architecture in the country. Churchland, Cradock, and West Park View provide established family neighborhoods at price points well below comparable Norfolk or Virginia Beach properties. The city is home to Norfolk Naval Shipyard, one of the Navy's oldest and largest, ensuring consistent demand from civilian shipyard workers and active-duty Navy personnel.
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
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