105 Bailey Dr, Williamsburg, VA 23188
Property image
Property image
OFF MARKET

105 Bailey Dr
Williamsburg, VA 23188

  • 4 Beds
  • 2.5 Baths
  • 1,376 sqft

$355,800

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $2,065/mo*
Refinance Your Home

$355,800

Trulia Estimate
as of Aug 25, 2026
Est. Refi. Payment $2,065/mo*
Refinance Your Home
4 Beds
2.5 Baths
1,376 sqft

Home Value

Trulia Estimate
$356K
Since last month
Decreased$5K (-1.2%)
Since last year
Increased$8K (+2.3%)
Since last sale
Increased$151K (+73.8%)
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 +78% in the last 10 years
MonthEstimated value
2026
August 2026$356K
July 2026$361K
June 2026$363K
May 2026$360K
April 2026$361K
March 2026$356K
February 2026$352K
January 2026$343K
2025
2024
2023
2022
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
3903 Strawberry Plains Rd, Williamsburg, VA
0.12
Single-Family Home
$250,000
07/28/26
3
1.5
1,200
3885 Strawberry Plains Rd, Williamsburg, VA
0.10
Single-Family Home
$370,000
06/05/26
3
2
1,426
4048 Bradshaw Dr, Williamsburg, VA
0.47
Single-Family Home
$402,000
03/31/26
3
2.5
1,600
130 Sharps Rd, Williamsburg, VA
0.70
Single-Family Home
$379,000
09/15/25
4
2
1,656
4003 Governors Sq #7, Williamsburg, VA
0.27
Single-Family Home
$175,000
09/19/25
3
2
1,071
3004 Ernest Ln, Williamsburg, VA
0.55
Single-Family Home
$420,000
04/15/26
4
3
2,249
126 Stanley Dr, Williamsburg, VA
0.69
Single-Family Home
$330,000
01/16/26
3
3
1,446
4901 Burnley Dr, Williamsburg, VA
0.65
Single-Family Home
$330,000
03/02/26
4
2.5
1,742
3677 Bridgewater Dr, Williamsburg, VA
0.39
Single-Family Home
$615,000
09/04/25
5
3
2,881
102 Tendril Ct, Williamsburg, VA
0.73
Single-Family Home
$450,000
07/01/26
4
2.5
1,927

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
3885 Strawberry Plains Rd, Williamsburg, VA 23188
0.10
$370,000
3
2
1,426
Recently Sold
3899 Strawberry Plains Rd, Williamsburg, VA 23188
0.13
$512,400
3
3
2,935
Off Market
3903 Strawberry Plains Rd, Williamsburg, VA 23188
0.12
$250,000
3
1.5
1,200
Recently Sold
139 Brook Haven Dr, Williamsburg, VA 23188
0.17
$394,000
3
2
1,949
Off Market
4015 Midlands Rd, Williamsburg, VA 23188
0.21
$205,000
2
1.5
1,050
Recently Sold
3872 Staffordshire Ln, Williamsburg, VA 23188
0.21
$219,900
3
1.5
1,130
Recently Sold
3858 Staffordshire Ln, Williamsburg, VA 23188
0.21
$211,000
3
1.5
1,130
Recently Sold
131 Brook Haven Dr, Williamsburg, VA 23188
0.23
$549,900
4
2
2,077
Recently Sold

Local Information

  • Map ViewExplore the area around 105 Bailey Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2005
Living Area
1,376 sqft
Price/Sqft
$259

About this House

Home sweet home! Beautiful home nestled in the city of Williamsburg with low taxes and no HOA dues. This turn key home offers 4 beds, 2.5 bath and first floor master suite. Gorgeous new luxury vinyl plank flooring throughout the first floor, new carpet upstairs, all new window treatment, gas fireplace in the family room and opens to the dining room. Beautiful new stainless-steel appliances and gas stove. Corner lot with beautiful landscaping, newly rebuilt front porch and wonderful deck out back which is perfect for entertaining. This home offers also includes walk-in closets, walk-in storage and gas heating and etc. Close proximity to New Town, William & Mary, urgent care, restaurants, shopping and colonial Williamsburg. Come see this home!
105 Bailey Dr, Williamsburg, VA 23188 is a 4 bedroom, 3 bathroom, 1,376 sqft single-family home built in 2005. It last sold for $205,000 on Sep 30, 2019. It is currently off market. The Trulia Estimate is $355,800, with a rent estimate of $2,372/month.

Home Details for 105 Bailey Dr

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Linoleum Vinyl
Interior Details
Number of Rooms: 7Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: OtherFoundation Type: Masonry

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 8276 sqft

Price and Tax history

DateEventPrice
Sep 30, 2019
Source: WMLS #1903199
Sold
$205,000
Aug 26, 2019
Source: Agent Provided
Pending
$215,000
Aug 15, 2019
Source: Agent Provided
PriceChange
$215,000
Price decreased by 4%
Jul 31, 2019
Source: Agent Provided
Listed For Sale
$225,000
Aug 9, 2017
Source: Agent Provided
ListingRemoved
$205,000

Market trends in Williamsburg

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$506K
$18.33KMoM
Sale-to-List Price
100.0%
0.2%MoM
Price per sq ft
$223
$3MoM
Available listings
503
42MoM

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.
  • 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
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  • 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
  • Jvshelton
    "Its a nice place to bring up children and many places in History to learn about And places to have fun Moderate temps all year great schools "
    0
    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

Frequently asked questions about 105 Bailey Dr

  • What is 105 Bailey Dr estimated to be worth?
    Trulia's estimated value for 105 Bailey Dr in Williamsburg, VA is $355,800.
  • What is the price history for 105 Bailey Dr?
    105 Bailey Dr in Williamsburg, VA last sold for $205,000 in September 2019.
  • 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 $506K. That is up $18.33K from the prior month.
  • Does 105 Bailey Dr have air conditioning?
    Yes, 105 Bailey Dr in Williamsburg, VA has air conditioning.
  • How big is the lot at 105 Bailey Dr?
    The lot at 105 Bailey Dr in Williamsburg, VA is about 0.19 acres (8,276 sq ft).

Explore by feature - Pet Friendly

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Off Market Homes Near 105 Bailey Dr

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