186 Cooley Dr, Middletown, VA 22645
OFF MARKET

186 Cooley Dr
Middletown, VA 22645

  • 4 Beds
  • 3.5 Baths
  • 2,331 sqft (on 5.10 acres)

$739,500

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $4,112/mo*
Refinance Your Home

$739,500

Trulia Estimate
as of Aug 15, 2026
Est. Refi. Payment $4,112/mo*
Refinance Your Home
4 Beds
3.5 Baths
2,331 sqft
(on 5.10 acres)

Home Value

Trulia Estimate
$740K
Since last month
Decreased$8K (-1.1%)
Since last year
Increased$7K (+0.9%)
Since last sale
Increased$297K (+66.8%)
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 +73% in the last 10 years
MonthEstimated value
2026
August 2026$742K
July 2026$748K
June 2026$751K
May 2026$759K
April 2026$751K
March 2026$744K
February 2026$716K
January 2026$710K
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
215 Thomas Dr, Middletown, VA
0.41
Single-Family Home
$515,000
09/26/25
3
2.5
2,410
1149 Cooley Dr, Middletown, VA
0.88
Single-Family Home
$620,000
05/05/26
5
3
3,076
515 River Ridge Dr, Middletown, VA
1.01
Single-Family Home
$750,000
02/23/26
4
4
4,144
43 Little Sorrel Dr, Middletown, VA
0.85
Single-Family Home
$677,000
07/16/26
6
4
4,164
111 Jackson Pl, Middletown, VA
1.02
Single-Family Home
$645,000
08/29/25
3
2
2,401
646 Guard Hill Rd, Middletown, VA
1.57
Single-Family Home
$549,000
05/29/26
4
3.5
2,768
2180 Strasburg Rd, Front Royal, VA
1.95
Single-Family Home
$575,000
09/30/25
4
3
2,236
20 Katie Ln, Middletown, VA
1.71
Single-Family Home
$584,933
03/05/26
4
3
2,312
1064 Strasburg Rd, Front Royal, VA
1.94
Single-Family Home
$460,000
07/17/26
4
2
2,088
3812 Guard Hill Rd, Front Royal, VA
1.39
Single-Family Home
$750,000
11/05/25
3
2
5,468

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
2383 Guard Hill Rd, Middletown, VA 22645
0.20
$241,700
3
2
1,296
Off Market
168 Thomas Dr, Middletown, VA 22645
0.32
$599,600
4
2.5
2,416
Off Market
68 Pine Hills Rd, Front Royal, VA 22630
0.33
-
-
-
-
Off Market
215 Thomas Dr, Middletown, VA 22645
0.41
$541,500
3
2.5
2,410
Off Market
322 Thomas Dr, Middletown, VA 22645
0.49
$822,300
3
3.5
4,604
Off Market
23 Guard Rd, Middletown, VA 22645
0.53
$230,300
1
1
910
Off Market
551 Jacksons Chase Dr, Middletown, VA 22645
0.63
$808,100
4
3
2,382
Off Market
140 Guard Rd, Middletown, VA 22645
0.64
$471,500
3
2.5
1,680
Off Market
228 Mercys Dr, Middletown, VA 22645
0.70
$925,000
5
5.5
5,672
For Sale
1064 Cooley Ln, Middletown, VA 22645
0.80
$785,700
5
3.5
4,842
Off Market
289 Reliance Woods Dr, Middletown, VA 22645
0.80
$730,000
3
2.5
2,642
For Sale
43 Little Sorrel Dr, Middletown, VA 22645
0.85
$677,000
6
4
4,164
Recently Sold

Local Information

  • Map ViewExplore the area around 186 Cooley 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
2004
Lot Size
5.1 acres
Living Area
2,331 sqft
Price/Sqft
$317
Parking
Garage

About this House

Custom built home on 5+acres, main level master suite is amazing w/columns, luxury master bath - his/her closets! great room w/wood burning fireplace, hardwood, custom kitchen, relax in the sunroom, formal dining! Bonus room is finished for 4th bedroom. Lower level is set up for in law suite, full bath & ktichen, Large deck, patio, sidewalks, landscaped. Add'l 3rd garage is in the back
186 Cooley Dr, Middletown, VA 22645 is a 4 bedroom, 4 bathroom, 2,331 sqft single-family home built in 2004. It last sold for $445,000 on Jun 1, 2018. It is currently off market. The Trulia Estimate is $739,500, with a rent estimate of $3,206/month.

Home Details for 186 Cooley Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Interior Details
Number of Rooms: 6
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Other, BrickFoundation Type: Stone
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 5.10 acres

Price and Tax history

DateEventPrice
Jun 1, 2018
Source: N/A
Sold
$445,000
Mar 27, 2018
Source: Agent Provided
Listed For Sale
$449,900

Market trends in Middletown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
23
7MoM
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Around this home

What Locals Say about Middletown

At least 18 Trulia users voted on each feature.

  • 90 % Say yards are well-kept

  • 89 % Say parking is easy

  • 86 % Say there's holiday spirit

  • 78 % Say car is needed

  • 67 % Say it's quiet

  • 67 % Say they plan to stay for at least 5 years

  • 65 % Say kids play outside

  • 61 % Say it's dog friendly

  • 60 % Say there are sidewalks

  • 55 % Say people would walk alone at night

  • 50 % Say streets are well-lit

  • 48 % Say it's walkable to restaurants

  • 43 % Say there's wildlife

  • 38 % Say neighbors are friendly

  • 35 % Say there are community events

  • 26 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Pgd26kdm7j
    "Limited yard area for some houses. However I do see lots of people walking their dogs on the sidewalk or even down at the park. "
    0
    Flag
  • Gsneff58
    "Really good neighborhood to live close to front Royal and Winchester really good schools shopping and rural area"
    0
    Flag
  • Barbi121770
    "The commute into town is easy and not busy at all. The neighborhood I live in is wonderful I couldn’t ask for better neighbors. "
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Apartments for Rent

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Homes for sale near 186 Cooley Dr

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Off Market Homes Near 186 Cooley Dr

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Frequently asked questions about 186 Cooley Dr

  • What is 186 Cooley Dr estimated to be worth?
    Trulia's estimated value for 186 Cooley Dr in Middletown, VA is $739,500.
  • What is the price history for 186 Cooley Dr?
    186 Cooley Dr in Middletown, VA last sold for $445,000 in June 2018.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a balanced market, based on recent for-sale activity.
  • What do residents say about Middletown?
    Residents describe Middletown, VA as well-kept, easy to park in, and quiet. Most residents say you need a car. See recently sold homes in Middletown, VA.
  • Does 186 Cooley Dr have air conditioning?
    Yes, 186 Cooley Dr in Middletown, VA has air conditioning.
  • Does 186 Cooley Dr have laundry facilities?
    Yes, 186 Cooley Dr in Middletown, VA has in-unit laundry.