5544 Pennington Pl, Williamsburg, VA 23188
OFF MARKET

$585,500

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,124 sqft (on 0.45 acres)

5544 Pennington Pl, Williamsburg, VA 23188

Est. Refi. Payment $3,527/mo*
Refinance Your Home
Currently Off Market - Sold Jun 10, 2025 for $579,900

Home Value

Trulia Estimate
$586K
Since last month
Increased$4K (+0.7%)
Since last year
Increased$6K (+1%)
Since last sale
Increased$5K (+0.9%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +46% in the last 10 years
MonthEstimated value
2026
September 2026$585K
August 2026$581K
July 2026$582K
June 2026$580K
May 2026$581K
April 2026$578K
March 2026$582K
February 2026$578K
January 2026$581K
2025
2024
2023
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5531 Westmoreland Dr, Williamsburg, VA
0.11
Single-Family Home
$580,000
12/09/25
4
2.5
2,637
4996 Westmoreland Dr, Williamsburg, VA
0.19
Single-Family Home
$500,000
12/12/25
4
2.5
2,438
4984 Westmoreland Dr, Williamsburg, VA
0.29
Single-Family Home
$644,000
10/24/25
4
2.5
2,930
4997 Westmoreland Dr, Williamsburg, VA
0.23
Single-Family Home
$600,000
06/05/26
3
3
2,705
5129 Thomas Ct, Williamsburg, VA
0.24
Single-Family Home
$502,000
06/17/26
4
2.5
2,755
5347 Rockingham Dr, Williamsburg, VA
0.31
Single-Family Home
$525,000
07/02/26
4
2.5
3,200
105 Heron Ct, Williamsburg, VA
0.15
Single-Family Home
$516,000
04/30/26
4
2.5
2,328
104 Heron Ct, Williamsburg, VA
0.14
Single-Family Home
$440,000
12/03/25
4
2.5
2,435
5385 Olde Towne Rd, Williamsburg, VA
0.40
Single-Family Home
$540,000
10/15/25
5
2.5
3,000
5545 Scotts Pond Dr, Williamsburg, VA
0.35
Single-Family Home
$525,000
06/30/26
4
2.5
2,858

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5527 Pennington Pl, Williamsburg, VA 23188
0.07
$630,400
4
3.5
3,220
Off Market
5523 Pennington Pl, Williamsburg, VA 23188
0.09
$710,800
4
3.5
3,424
Off Market
91 Kestrel Ct, Williamsburg, VA 23188
0.13
$469,800
5
3
2,540
Off Market
5531 Westmoreland Dr, Williamsburg, VA 23188
0.11
$580,000
4
2.5
2,637
Recently Sold
104 Heron Ct, Williamsburg, VA 23188
0.14
$440,000
4
2.5
2,435
Recently Sold
88 Kestrel Ct, Williamsburg, VA 23188
0.15
$493,000
4
2.5
2,199
Off Market
105 Heron Ct, Williamsburg, VA 23188
0.15
$516,000
4
2.5
2,328
Recently Sold
112 Teal Way, Williamsburg, VA 23188
0.17
$415,200
3
2
1,593
Off Market
112 Puffin Ln, Williamsburg, VA 23188
0.18
$525,000
4
2.5
2,274
For Sale
4996 Westmoreland Dr, Williamsburg, VA 23188
0.19
$500,000
4
2.5
2,438
Recently Sold
122 Tracy Ct, Williamsburg, VA 23185
0.25
$478,300
3
2
2,095
Off Market

Local Information

  • Map ViewExplore the area around 5544 Pennington Pl.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2005
0.45 acre lot
3,124 sqft
$187/sqft
2 Car Garage
HOA $33/mo

About this House

What's unique:Gas fireplaceSitting areaAccess to the deckQuiet cul-de-sacJack and jill bathroomWalk-in pantry
This home is tucked in a quiet cul-de-sac 2 miles from the Outlets. It’s full of unique features & upgrades, including a new fridge, washer/dryer, and a layout that’s both functional & fun.
The 1st floor has wood floors, cathedral ceilings, and a gas fireplace in the living room. A cutout opens to the loft-style second floor, adding character and creating a natural flow between levels. The kitchen features a breakfast area, walk-in pantry, coffee bar, access to the deck as well as a private office just off the kitchen.
The backyard is fully fenced and impressively sized—with 4 garden beds, mature trees for privacy, blueberry bushes, a peach tree, and a peaceful setting backed by a conservation area.
The oversized primary suite includes two walk-in closets, a sitting area, walk-in shower and bench. Two more big bedrooms—each with walk-in closets—share a Jack and Jill bathroom. The laundry room is located on the same floor.
The third floor offers a bonus space with skylights, a full bathroom, window nook perfect for guestroom, playroom or gym. This home is turn key, packed with storage and full of thoughtful details throughout.
Come look it keeps getting better the more you explore!
5544 Pennington Pl, Williamsburg, VA 23188 is a 4 bedroom, 4 bathroom, 3,124 sqft single-family home built in 2005. It last sold for the $579,900 asking price on Jun 10, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $585,500, with a rent estimate of $3,332/month.
Last check for updates: about 11 hours ago
Listed by Maggie Paige, (561) 818-3883
Kingsmill Realty, Inc.
Bought with: John Womeldorf, (757) 254-8136, Liz Moore & Associates-2
Originating MLS: Williamsburg MLS
Source: WMLS, MLS#2501571

Home Details for 5544 Pennington Pl

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Family Room, Kitchen, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3124 Square Feet
Appliances & Utilities
Appliances: Dryer, Dishwasher, Disposal, Gas Water Heater, Microwave, Range, Refrigerator, WasherDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural Gas,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Fireplace: GasHas a Fireplace
Windows, Doors, Floors & Walls
Flooring: Carpet, Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Tile, Wood

Exterior Features

Exterior Home Features
Patio / Porch: Deck, Front PorchFencing: Back Yard, PicketExterior: Deck
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Direct Access,Garage,Garage Door Opener,Two Spaces
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Transitional
Building
Construction Materials: Drywall, Frame, Vinyl SidingNot a New ConstructionNot Attached Property
Property Information
Parcel Number: 3221300010

Price & Status

Price
List Price: $579,900
Status Change & Dates
Off Market Date: Mon May 19 2025Possession Timing: Close Of Escrow

Active Status

MLS Status: Closed

Location

Direction & Address
City: WilliamsburgCommunity: Westmoreland
School Information
Elementary School: J Blaine BlaytonJr High / Middle School: Lois S HornsbyHigh School: LafayetteWalk Score: 7

Community

Community Features: Common Grounds/Area, Playground, Park
Other
Playground

HOA

HOA Name: Mystreet Community ManagementHOA Phone: 804-359-2895Association for this Listing: Williamsburg MLSHas an HOAHOA Fee: $33/Monthly

Lot Information

Lot Area: 0.45 acres

Business

Business Information
Ownership: Fee Simple, Individuals

Miscellaneous

Mls Number: 2501571Living Area Range Units: Square Feet

Additional Information

Common Grounds/AreaPlaygroundPark

Price and Tax history

DateEventPrice
Jun 10, 2025
Source: WMLS #2501571
Sold
$579,900
May 19, 2025
Source: WMLS #2501571
Pending
$579,900
May 13, 2025
Source: WMLS #2501571
Contingent
$579,900
May 10, 2025
Source: WMLS #2501571
Listed For Sale
$579,900
Nov 1, 2023
Source: WMLS #2302983
Sold
$535,000

Market trends in Williamsburg

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$498K
$3.33KMoM
Sale-to-List Price
100.0%
Price per sq ft
$221
$2MoM
Available listings
519
15MoM

Around this home

What Locals Say about Williamsburg

At least 506 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 87 % Say car is needed

  • 83 % Say parking is easy

  • 80 % Say there's holiday spirit

  • 78 % Say it's quiet

  • 74 % Say people would walk alone at night

  • 73 % Say yards are well-kept

  • 69 % Say kids play outside

  • 60 % Say there's wildlife

  • 56 % Say neighbors are friendly

  • 55 % Say there are sidewalks

  • 52 % Say they plan to stay for at least 5 years

  • 49 % Say streets are well-lit

  • 36 % Say there are community events

  • 35 % Say it's walkable to restaurants

  • 34 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Kimchamblin
    "We’ve lived around the world and chose Williamsburg as our “forever home” after living here years ago. It’s wonderful!"
    0
    Flag
  • Trulia User
    "My area is very dog friendly "
    0
    Flag
  • Mspeek35
    "We just moved here 4 years ago the schools are good there’s a lot of things to as a family "
    0
    Flag
  • Yfz4k7khrd
    "great access, good people, nice place to live"
    0
    Flag
  • Smancilla10
    "Many families with dogs in my neighborhood. It feels safe to walk during the day and at night. All owners pick up after their dogs. "
    0
    Flag
  • Amy Guerin
    "There is a local concert series in spring and summer seasons. Many locals attend, and it’s amazing. "
    0
    Flag
  • Patsy7
    "Ability to walk your dog safely, 99% of the time. Minimum traffic to be concerned about, and it is clean in the streets mostly."
    0
    Flag
  • Laila Richard
    "Colonial Williamsburg is nearby and has community events every holiday. William & Mary College also has many activities and events. "
    0
    Flag
  • R6hqhw7b4c
    "No dogs larger than minis allowed, it is very sad. "
    0
    Flag
  • Carter25102000
    "Easy commute. I’m right by major highways and streets. My drive to work isn’t that bad and drive to Richmond isn’t too bad either"
    0
    Flag
  • Betticushing
    "There are many people walking their dogs on leashes and they seem to enjoy the neighborhood. Most people pick up after their dogs, though I’ve seen an occasional pile of doggie poop on the edge of the road. "
    0
    Flag
  • Mrs. Alicia D. roberts
    "Nice walking trails, a lot of bark parks, there is nothing they would t like as long as they are taken care of."
    0
    Flag
  • Romamer
    "We have Veteran’s Park a mile away that has play area for kids, free pickleball courts, and beautiful gardens with a picnic area. "
    0
    Flag
  • Aiden Mills
    "Unless your work is in Williamsburg a car is always needed. Traffic is not bad and only really gets congested around the tourist areas and even then it’s not too bad."
    0
    Flag
  • Casheeish
    "The historic area of Colonial Williamsburg is located conveniently nearby and provides an excellent venue for dog walking"
    0
    Flag
  • Aiden Mills
    "Dog owners would love the grass and dog park in my area. Owners would not like the amount of cars going through my neighborhood."
    0
    Flag
  • Casheeish
    "The Grand Illumination and Independence Day festivities in the historic area of Colonial Williamsburg are celebrations unique to our community. "
    0
    Flag
  • Ashlee C
    "My commute can range anywhere from seven to eleven minutes depending on traffic. It’s a very easy ride to work and I’m greatful for that!"
    0
    Flag
  • Jygz8p77tx
    "Wonderful town to call home. Safe and friendly community. Good schools and hospitals. Many community businesses as well as churches. "
    0
    Flag
  • Trulia User
    "It’s a very nice family friendly neighborhood, very quiet. Well maintained, and centrally located to lots of stores and highway"
    0
    Flag
  • Trulia User
    "The area has a great holiday spirit, nobody is too neighborly per se, but people do check on each other. During the holidays ie. Christmas time a lot of the people here decorate their houses and people drive around and look at the holiday lights. Also, during Halloween a lot of the kids go and trick-or-treat together."
    4
    Flag
  • Trulia User
    "Quiet, safe close to schools and stores. Lots of pet owners who watch out for neighbors pets and houses"
    4
    Flag
  • Trulia User
    "pretty good neighborhood. we have a store and 3 churches all within a vert short walking distance. There is also a school with a park for kids."
    2
    Flag
  • Trulia User
    "Small, can be busy with kids in the summer of course, but clean, small trail along the front, community pool and playground, nice neighbors in my experience. Management? Eh. "
    1
    Flag
  • Trulia User
    "we love this neighborhood! it is great for raising a family! we are close to lots of cool places and a wonderful church!"
    1
    Flag
  • Sharon H.
    "My neighborhood is in a great location and has a very diverse population. The public transportation is at the entrance of my neighborhood.The lawns are well manicured. The busses are clean and social distancing is practiced. It is a comfortable ride and the people are nice. There are stores and eateries are right on the line."
    3
    Flag
  • Jessica W.
    "Very warming, clean sides roads and lots of deers!!. "
    21
    Flag
  • Tara B.
    "Obly has a 20 minute drive to Fort Eustis military installation every day. Newly paved highway lanes make it even more accessible."
    1
    Flag
  • Betsyedwards11
    "Great school district and neighborhood- one way in one way out - never farther than 20 min from anywhere in Williamsburg "
    0
    Flag
  • Joy B.
    "There’s a lot of families here, activities for the children is abundant, then you have the historical side which is great for learning. "
    8
    Flag
  • Julie C.
    "Williamsburg is a safe community with great schools. I especially like to different cultural event available. "
    0
    Flag
  • Adam D.
    "Williamsburg is exciting not because of what it *is*, but because of what it is *going to* be, or what it *could* be. Lots of southern passive aggression, but also lots of truly friendly, laid back people. Look for the city to get younger and younger as the "college town" infrastructure continues to expand."
    23
    Flag
  • Trulia User
    "Great for families. Plenty of places to eat and shop. As well as loads of history to see and visit. "
    3
    Flag
  • Caroline C.
    "The Williamsburg farmers market is my favorite community event. Everyone brings their families and pets, and it feels good to support small farmers. "
    0
    Flag
  • Latrelle J.
    "I was born and raised here and if I could afford to live here I’d stay! The chills are ok if you stay in touch with the teachers and up to date with your child’s progress yourself. It’s clean too."
    2
    Flag
  • Peter L.
    "People are nice and it feels safe to walk around at night. I never had a problem with anyone. It's great gor kids and family to visit."
    0
    Flag
  • Ruca60
    "It’s friendly, cultured, good values, easy to get around in your car, lots restaurants, lots to do. And the beach is only an hour and a half away."
    0
    Flag
  • Kelly
    "I’ve lived in this neighborhood for 3 years... lots of long time residents and houses do not come up for sale often. Kid and dog friendly. Close to the York river State Park"
    4
    Flag
  • Laura W.
    "Colonial Williamsburg is wonderful for company and for every day adventures. There are a good mix of people and a large dog community. "
    0
    Flag
  • Gonzalez
    "It’s a great neighborhood because is very quiet. There is nothing more complacent then coming home from a long day of work and being able to relax and enjoy the calming and peaceful atmosphere of your home and neighborhood "
    0
    Flag

LGBTQ Local Legal Protections

The data relating to real estate for sale on this website comes in part from the Internet Data Exchange Program of the WMLS. Real estate listings held by brokerage firms other than Zillow, Inc. are marked with the Internet Data Exchange logo or the Internet Data Exchange brief/thumbnail logo and detailed information about them includes the name of the listing firms.
© 2026 WMLS. All rights reserved.

Frequently asked questions about 5544 Pennington Pl

  • What is 5544 Pennington Pl estimated to be worth?
    Trulia's estimated value for 5544 Pennington Pl in Williamsburg, VA is $585,500.
  • What is the price history for 5544 Pennington Pl?
    5544 Pennington Pl in Williamsburg, VA last sold for $579,900 in June 2025.
  • Is Williamsburg a buyer's or seller's market?
    Williamsburg is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Williamsburg?
    The median sale price in Williamsburg is $498K. That is down $3.33K from the prior month.
  • Does 5544 Pennington Pl have air conditioning?
    Yes, 5544 Pennington Pl in Williamsburg, VA has air conditioning.
  • Does 5544 Pennington Pl have laundry facilities?
    Yes, 5544 Pennington Pl in Williamsburg, VA has in-unit laundry.

Explore by feature - Pet Friendly

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