558 Windermere Dr, Culpeper, VA 22701
OFF MARKET

558 Windermere Dr
Culpeper, VA 22701

  • 4 Beds
  • 3 Baths
  • 2,106 sqft

$469,300

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,680/mo*
Refinance Your Home

$469,300

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,680/mo*
Refinance Your Home
4 Beds
3 Baths
2,106 sqft

Home Value

Trulia Estimate
$469K
Since last month
Decreased$5K (-1%)
Since last year
Increased$12K (+2.6%)
Since last sale
Increased$212K (+83.2%)
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 +77% in the last 10 years
MonthEstimated value
2026
August 2026$467K
July 2026$472K
June 2026$477K
May 2026$476K
April 2026$471K
March 2026$465K
February 2026$461K
January 2026$457K
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
176 Vaughn Ct, Culpeper, VA
0.19
Single-Family Home
$485,000
03/05/26
4
2.5
2,433
566 Windermere Dr, Culpeper, VA
0.03
Single-Family Home
$518,900
11/19/25
4
3.5
3,842
487 Kearns Dr, Culpeper, VA
0.21
Single-Family Home
$435,000
02/10/26
3
2.5
2,197
648 Windermere Dr, Culpeper, VA
0.22
Single-Family Home
$475,000
01/27/26
4
2.5
2,156
421 Wayland Rd, Culpeper, VA
0.32
Single-Family Home
$450,000
04/10/26
4
2.5
1,580
581 Windermere Dr, Culpeper, VA
0.08
Single-Family Home
$583,750
08/06/26
5
4
3,078
219 Lesco Blvd, Culpeper, VA
0.06
Single-Family Home
$387,000
06/11/26
3
2
1,440
1141 Virginia Ave, Culpeper, VA
0.25
Single-Family Home
$400,000
10/31/25
3
2.5
2,800
632 Windermere Dr, Culpeper, VA
0.25
Single-Family Home
$525,000
07/24/26
4
3
3,482
553 Windermere Dr, Culpeper, VA
0.04
Single-Family Home
$602,564
05/22/26
4
3.5
3,915

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
553 Windermere Dr, Culpeper, VA 22701
0.04
$602,564
4
3.5
3,915
Recently Sold
540 Greenbriar Dr, Culpeper, VA 22701
0.06
$601,800
6
3.5
4,539
Off Market
566 Windermere Dr, Culpeper, VA 22701
0.03
$518,900
4
3.5
3,842
Recently Sold
575 Windermere Dr, Culpeper, VA 22701
0.06
$499,100
4
2.5
2,381
Off Market
211 Lesco Blvd, Culpeper, VA 22701
0.03
$426,200
3
2.5
1,566
Off Market
581 Windermere Dr, Culpeper, VA 22701
0.08
$583,750
5
4
3,078
Recently Sold
219 Lesco Blvd, Culpeper, VA 22701
0.06
$387,000
3
2
1,440
Recently Sold
546 Windermere Dr, Culpeper, VA 22701
0.08
$467,300
3
2.5
1,865
Off Market
1116 Virginia Ave, Culpeper, VA 22701
0.14
$465,000
3
2
1,888
Off Market
715 Hawkshead Ct, Culpeper, VA 22701
0.16
$585,300
4
3
3,223
Off Market
487 Kearns Dr, Culpeper, VA 22701
0.21
$435,000
3
2.5
2,197
Recently Sold
648 Windermere Dr, Culpeper, VA 22701
0.22
$475,000
4
2.5
2,156
Recently Sold

Local Information

  • Map ViewExplore the area around 558 Windermere 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
2,106 sqft
Price/Sqft
$223
Parking
Garage

About this House

Very Well Maintained Colonial - 4 Bedrooms 2.5 Bathrooms, Formal Living and Dining Rooms, Family Room off of Kitchen with Gas Fireplace, Large Soaking Tub in Master Bathroom - Home Warranty - Priced to Sell !! Please remove shoes or use booties .
558 Windermere Dr, Culpeper, VA 22701 is a 4 bedroom, 3 bathroom, 2,106 sqft single-family home built in 2005. It last sold for $255,000 on Jun 5, 2015. It is currently off market. The Trulia Estimate is $469,300, with a rent estimate of $2,583/month.

Home Details for 558 Windermere Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Carpet, Hardwood
Interior Details
Number of Rooms: 8Types of Rooms: Walk In Closet
Appliances & Utilities
DishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: VinylFoundation Type: Concrete
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

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

Lot Information

Lot Area: 9583 sqft

Mobile R/V

RV Parking
Rv Parking

Price and Tax history

DateEventPrice
Jun 5, 2015
Source: N/A
Sold
$255,000
May 7, 2015
Source: Agent Provided
Pending
$259,900
Apr 11, 2015
Source: Agent Provided
Listed For Sale
$259,900
Aug 27, 2008
Source: N/A
Sold
$215,000
Jun 27, 2008
Source: Agent Provided
PriceChange
$224,900
Price decreased by 4%

Market trends in Culpeper

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$468K
$9KMoM
Sale-to-List Price
100.0%
Price per sq ft
$219
$12MoM
Available listings
141
2MoM

Around this home

What Locals Say about Culpeper

At least 147 Trulia users voted on each feature.

  • 89 % Say car is needed

  • 86 % Say it's dog friendly

  • 81 % Say yards are well-kept

  • 81 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 67 % Say there are sidewalks

  • 66 % Say kids play outside

  • 57 % Say people would walk alone at night

  • 56 % Say streets are well-lit

  • 54 % Say neighbors are friendly

  • 53 % Say it's quiet

  • 51 % Say there's wildlife

  • 48 % Say it's walkable to grocery stores

  • 44 % Say it's walkable to restaurants

  • 41 % Say they plan to stay for at least 5 years

  • 41 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Rita Marie Fernandez
    "A lot going on on main steeet. Farmers market, coffee shop & little shops. Charming little town to explore"
    0
    Flag
  • Unspecified
    "People walking their dogs. Kids playing with dogs. It's a very pet friendly neighborhood. Wildlife such as squirrels, rabbits, skunks snakes along with a slew of other animals."
    8
    Flag
  • Pbijole
    "There’s plenty of space to walk dogs in the neighborhood. There are a few hills and people walk their dogs all the time. There are only sidewalks on one side of the street."
    1
    Flag
  • Lucy M. T.
    "We all look out for each other and we respect our neighbors. It is a very quiet, nice place to live. Been living here for fifty years. "
    2
    Flag
  • Heather J. .
    "I love where I live… I teach here, my kids go to school here, and I feel very safe in this area. My rent has increased and I just want to move to a better place with the yard for my children"
    0
    Flag
  • Elizabeth M.
    "I’ve personally lived here for the past decade or so, but my family goes back generations in this area. With a delightful downtown, great walk-ability, and amazing character this is the perfect community for families and more. "
    1
    Flag
  • Patrick P.
    "Halloween is a very fun time with lots of families participating. Each year we take our two kids and go with 3 other families. "
    0
    Flag
  • Dackota M.
    "Everyone knows just about everyone. Most people are friendly. I lived here for 17 years and after moving I come and visit. I still see people from high school. "
    1
    Flag
  • Nina K.
    "This area has a wonderful park district. The downtown area has some great restaurants and shops and people are very friendly. Unlike some parts of the country, this area is growing quickly and the town is vibrant. "
    1
    Flag
  • Sarah B.
    "It’s not bad if you live in Culpeper but if you have to go into the city then it starts to get rough. "
    0
    Flag
  • Kim Smith
    "Great small town with family roots and wonderful people. Nice place to raise a family. Great schools in the area too. "
    0
    Flag
  • Anonymous
    "I work in Manassas which takes an hour in the morning due to heavy traffic. The ride home at night sometimes takes longer. "
    0
    Flag
  • Trulia User
    "We have quarterly neighborhood garage sales. National night out event. Also we are a huge Halloween neighborhood with lots of houses putting on shows"
    3
    Flag
  • Tammy
    "I commute 25 miles each way everyday to work. My commute to downtown Culpeper is within walking distance. "
    0
    Flag
  • Frank P.
    "Pro: plenty of dog owners;recently installed pet waste stations Con: no dog park in Redwood Lakes subdivision "
    0
    Flag
  • Tammy
    "We live in town and enjoy all the options for shopping and dining. We have also lived in more rural locations and found that very relaxing as well."
    0
    Flag
  • Elder M. N. M.
    "Dog owners like that there are a lot of places to walk Dogs. What they don’t like is that some Streets are not well lit. Plus they must clean up after their Dogs. "
    0
    Flag
  • Aceofstars
    "We have regular community yard sales, HOA meetings, and other neighborhood events. Lived here for 13 years now and love the area. "
    0
    Flag
  • Tammy
    "I have lived here for 2 years and it is very convenient to live in town. I love the shops and restaurants in town as well."
    0
    Flag
  • Sjhall13
    "All my neighbors have dogs and there is a friendly dog park close by. We walk our dog to the close field so he can run and get plenty of exercise"
    0
    Flag
  • Sjsnoderly
    "I don't commute for work. if you do, you need a car. There is no public transportation available. There are minimal delays when working local."
    1
    Flag
  • Elpelon1985
    "I live in this area for 17 years an I love the neighborhood and the people who live here are very kind and there’s a lot of job opportunities for most of the people here"
    0
    Flag
  • Spradlind88
    "Quiet, newer neighborhood, close to amenities. Lived here for 3 years and am very happy with the neighborhood. "
    0
    Flag
  • Meachus
    "I moved to Culpeper from Northern Virginia back in 2001 when Culpeper was still considered a small town, and the I was visited by the welcome wagon when I moved in to my house. After living in Culpeper for 10 years, I moved to Rappahannock county for 7&1/2 yrs, now due to life changes that are out of my control I am moving back to Culpeper and it's definitely grown up from the small town it once was, and I won't be excepting the welcome wagon this time around but it's certainly not Fairfax or Gainesville. Not yet anyway."
    1
    Flag
  • Heathermichelle D.
    "great place to live if like community living. Lots of kids. Family and pet friendly. Ryan homes is currently expanding the neighborhood and things are looking to get better."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 558 Windermere Dr

  • What is 558 Windermere Dr estimated to be worth?
    Trulia's estimated value for 558 Windermere Dr in Culpeper, VA is $469,300.
  • What is the price history for 558 Windermere Dr?
    558 Windermere Dr in Culpeper, VA last sold for $255,000 in June 2015.
  • Is Culpeper a buyer's or seller's market?
    Culpeper is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Culpeper?
    The median sale price in Culpeper is $468K. That is up $9K from the prior month.
  • Does 558 Windermere Dr have air conditioning?
    Yes, 558 Windermere Dr in Culpeper, VA has air conditioning.
  • Does 558 Windermere Dr have laundry facilities?
    Yes, 558 Windermere Dr in Culpeper, VA has in-unit laundry.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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