185 Whimsy Ln, Winchester, VA 22602
OFF MARKET

$589,300

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,426 sqft (on 5 acres)

185 Whimsy Ln, Winchester, VA 22602

Est. Refi. Payment $3,497/mo*
Refinance Your Home
Currently Off Market - Sold Mar 23, 2005 for $500,000

Home Value

Trulia Estimate
$589K
Since last month
Decreased$6K (-1%)
Since last year
Increased$17K (+3%)
Since last sale
Increased$91K (+18.2%)
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 +75% in the last 10 years
MonthEstimated value
2026
October 2026$591K
September 2026$591K
August 2026$597K
July 2026$606K
June 2026$606K
May 2026$604K
April 2026$600K
March 2026$588K
February 2026$583K
January 2026$577K
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
227 Dutch Apple Dr, Winchester, VA
1.28
Single-Family Home
$650,000
03/02/26
3
2.5
2,436
3721 Cedar Creek Grn, Winchester, VA
0.62
Single-Family Home
$130,000
09/21/26
3
1
1,330
107 Petry Ct, Winchester, VA
0.93
Single-Family Home
$715,000
06/12/26
4
3
3,562
1491 Pitcock Ln, Winchester, VA
1.60
Single-Family Home
$718,300
03/16/26
3
2
2,139
254 Whistlewood Ln, Winchester, VA
1.32
Single-Family Home
$890,000
03/27/26
5
6.5
4,301
115 Germany Rd, Winchester, VA
1.68
Single-Family Home
$611,500
12/19/25
4
2.5
2,520
1019 Gough Rd, Winchester, VA
1.44
Single-Family Home
$211,500
05/20/26
3
2
1,680
278 Rubinette Way, Winchester, VA
1.88
Single-Family Home
$800,000
05/19/26
3
3.5
2,577
4241 Cedar Creek Grn, Winchester, VA
1.60
Single-Family Home
$799,000
09/16/26
4
3.5
3,120
147 Tilden Ct, Winchester, VA
1.42
Single-Family Home
$17,000
02/25/26
3
4
3,232

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
205 Whimsy Ln, Winchester, VA 22602
0.08
$698,700
3
2
2,011
Off Market
170 Whimsy Ln, Winchester, VA 22602
0.09
$839,600
4
3.5
4,740
Off Market
190 Whimsy Ln, Winchester, VA 22602
0.11
$708,800
4
3
3,120
Off Market
3429 Cedar Creek Grn, Winchester, VA 22602
0.12
$649,700
3
4
3,614
Off Market
121 Grange Ln, Winchester, VA 22602
0.13
-
2
2
1,108
Off Market
3443 Cedar Creek Grn, Winchester, VA 22602
0.13
$579,000
4
4
2,764
Off Market
3407 Cedar Creek Grn, Winchester, VA 22602
0.13
$658,500
4
4
3,828
Off Market
195 Grange Ln, Winchester, VA 22602
0.13
$413,500
3
1
2,526
Off Market
3461 Cedar Creek Grn, Winchester, VA 22602
0.15
$492,800
4
3
2,716
Off Market
3391 Cedar Creek Grn, Winchester, VA 22602
0.15
$532,100
3
1
1,108
Off Market
3477 Cedar Creek Grn, Winchester, VA 22602
0.16
$568,400
4
3
2,846
Off Market
256 Grange Ln, Winchester, VA 22602
0.19
$647,700
3
2
1,512
Off Market
3474 Cedar Creek Grn, Winchester, VA 22602
0.22
$500,600
3
3
2,096
Off Market
3527 Cedar Creek Grn, Winchester, VA 22602
0.24
-
-
-
-
Off Market
3309 Cedar Creek Grn, Winchester, VA 22602
0.26
$472,900
3
2
2,712
Off Market
3500 Cedar Creek Grade #B, Winchester, VA 22602
0.26
-
Studio
-
-
Off Market
3500 Cedar Creek Grn, Winchester, VA 22602
0.27
$742,900
4
4
3,069
Off Market
3291 Cedar Creek Grn, Winchester, VA 22602
0.27
$414,400
2
2
1,547
Off Market
0 Cedar Creek Grade, Winchester, VA 22601
0.29
-
-
-
-
Off Market
Cedar Creek Grade, Winchester, VA 22602
0.32
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 185 Whimsy Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2006
5 acre lot
2,426 sqft
$243/sqft

About this House

Do you dream of country life but don't want the distance from town? This home is 3.5 miles from town and sits at the back of 5ACREs. 3 Large bedrooms, 2.5 baths. Master has 2 walk in closets. Main level has large Family room with mountain views. Office/formal living room. Eat-in kitchen with sitting area. Unfinished walk-out basement just waiting for your finishing touches. Patio for entertaining.
185 Whimsy Ln, Winchester, VA 22602 is a 3 bedroom, 3 bathroom, 2,426 sqft single-family home built in 2006. It last sold for $500,000 on Mar 23, 2005. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $589,300, with a rent estimate of $2,655/month.

Home Details for 185 Whimsy Ln

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Number of Rooms: 7Types of Rooms: Breakfast Nook, Dining Room, Family Room
Levels, Entrance, & Accessibility
Floors: Carpet, Linoleum Vinyl

Exterior Features

Exterior Home Features
Roof: OtherExterior: VinylFoundation Type: Concrete
Parking & Garage
Parking: None

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 5.00 acres

Price and Tax history

DateEventPrice
Aug 6, 2016
Source: Agent Provided
ListingRemoved
$345,000
Jun 8, 2016
Source: Agent Provided
Pending
$345,000
May 19, 2016
Source: Agent Provided
Listed For Sale
$345,000
Sep 30, 2015
Source: Agent Provided
ListingRemoved
$335,000
Aug 20, 2015
Source: Agent Provided
PriceChange
$335,000
Price decreased by 3%

Market trends in Winchester

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$393K
$3.33KMoM
Sale-to-List Price
99.9%
0.1%MoM
Price per sq ft
$221
$1MoM
Available listings
346
37MoM

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winchester

At least 465 Trulia users voted on each feature.

  • 84 % Say car is needed

  • 81 % Say it's dog friendly

  • 81 % Say parking is easy

  • 77 % Say yards are well-kept

  • 73 % Say there's holiday spirit

  • 69 % Say kids play outside

  • 64 % Say people would walk alone at night

  • 64 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 55 % Say it's quiet

  • 52 % Say neighbors are friendly

  • 49 % Say it's walkable to restaurants

  • 49 % Say there's wildlife

  • 48 % Say they plan to stay for at least 5 years

  • 36 % Say it's walkable to grocery stores

  • 28 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • 7seymours
    "It’s quiet, owners take care of their homes, and it’s safe! And pretty! "
    9
    Flag
  • Hmrtgptw2c
    "I drive to and from work. The city has public transportation with WinReady I think it’s called. There is ride share in the area as well."
    4
    Flag
  • George
    "I’ve only lived here several weeks but am impressed by the people in our neighborhood. Polite and friendly."
    14
    Flag
  • Jessica J Contreras
    "There are no sidewalks or safe areas to walk with pets. Cars go by fast. It would be unsafe to walk. "
    2
    Flag
  • 7seymours
    "We live in a beautiful, safe area with an excellent county school system. Our neighbors have pride and take care of their properties in the Green Spring area"
    10
    Flag
  • Izzy874
    "Apple blossom every single year I love it! The food is amazing, the games, the carnival, and especially the parades and events to go too!"
    4
    Flag
  • Singsongone
    "Lived in this quiet neighborhood little over ten years. Convenient to major highways and bypasses, hospital, doctors, grocery and retail stores, restaurants. Lovely mature trees throughout, some wildlife and one can easily hear morning/evening birds. Residents take pride in the appearance of their homes and yards and look out for one another. "
    5
    Flag
  • Smlrws
    "I’ve lived here for a year and my street is much quieter than I ever expected since I live with a mile of the downtown area. It’s safe. There are many restaurants, coffe shops, hair salons, etc. within walking distance !"
    6
    Flag
  • Kelrendon83
    "Great community for live , safe and good for raise kids and the family can have a good place to visit , some good festivals "
    12
    Flag
  • 7seymours
    "Lived here for 22 yrs. Beautiful, spacious, quiet and good neighbors! We feel safe here with a lot of privacy. Neighbors look out for each other & help each other "
    11
    Flag
  • Gfbzc98z9n
    "It is Quiet and safe while still being just a short trip to the big city. Beautiful downtown walking mall. Great outdoors all around in the Blue Ridge Mountains."
    9
    Flag
  • 7seymours
    "Apple Blossom Festival which is held annually with parades, celebrities, dances, music & arts & crafts. A beautiful weekend during Apple Blossom time with over 250,000 visitors attending this special event in the Shenandoah Valley "
    10
    Flag
  • Trulia User
    "Everyone I have ran into has been nice. Definitely a very family friendly neighborhood. Feels very cozy "
    8
    Flag
  • Morganva
    "Dog friendly, plenty of green space, and lots of dog bag dispensers for cleaning up after the pooch. "
    8
    Flag
  • Bridgetdefoe
    "It’s easy to get around Winchester. Roads are well maintained. Traffic is minimal. You can get about anywhere in Winchester is less than 20 minutes. Rt 7 has become busy as an exception due to people commuting to Loudoun County "
    9
    Flag
  • Isabelle M.
    "Is a nice ride and no traffic in the area, many shopping centers, great area to visit, one of the great hospital in the nation."
    7
    Flag
  • Alliav11%40gmail.com
    "A lot of people have dogs here and they are always waking them. There are a lot of stray cats so if dogs don’t like them beware"
    0
    Flag
  • Gina A.
    "It's just a nice neighborhood to walk. People are always waving and stopping to chat. And they clean up after their dogs"
    4
    Flag
  • Cooda K.
    "It’s a lot It’s a lot I can say I honestly feel like it’s a beautiful place I mean the cabs suck But other than that I feel like it’s a nice expensive place to live 😁 "
    3
    Flag
  • Topeye
    "Very good schools, low crime rate, good jobs. Civic pride. Great long-running annual community festival. Many churches and civic organizations are active. Historic preservation. "
    5
    Flag
  • Rob R.
    "My commute to downtown is usually fairly quick, not too much traffic. Public transportation is not very popular."
    3
    Flag
  • Nickruiz270
    "The commute into Winchester is fairly light but around 5pm it’s when it gets heavy. I would try to avoid all small roads as much as possible and use the highway as much as possible. "
    2
    Flag
  • Careliza81
    "We are just walking distance to the walking mall which has tons of activities throughout the year. There are festivals for most major holidays and apple blossom. "
    3
    Flag
  • Nick A.
    "There is a great community of people here and it’s very welcoming. Living here is home for me and I would recommend moving here if you want to be close to major metropolis and still be near countryside"
    3
    Flag
  • Chels J.
    "Great safe place for kids no strange people more of a older group of people live here. It’s out of the way of the city but seconds from town"
    51
    Flag
  • Brock M.
    "Great area to live and raise a family. Good earnings potential. Great university. Awesome private and public school system."
    2
    Flag
  • Coach_ramos
    "You must drive or carpool. There is a local bus/trolley, but only locally within the city. No rail or subway."
    2
    Flag
  • Leslie H.
    "I commute to Northern Va and Loudoun Co. it’s more brutal each year, especially the return commute. "
    0
    Flag
  • Brad M.
    "Old town feel and downtown is lively. We enjoy being able to walk in a safe environment and walk to restaurants and shops. A great place to live in a historic town. "
    2
    Flag
  • Yesenia R.
    "The community center provides events for all. From all the holidays to special events for fundraisers along with also assisting the community with school supplies. There’s also playgrounds and pools."
    2
    Flag
  • Danielle M.
    "There are no community events in my neighborhood...everyone mostly keeps to themselves with the exception of those of us who have lived here for over thirty years. "
    0
    Flag
  • Erin G. .
    "Nothing special, just a nice neighborhood. Nice and quiet. Friendly folks. Safe for kids to play. Convenient to shopping."
    1
    Flag
  • Samantha F.
    "There is a large park just a few blocks away. Enough room to let a we trained dog off the leash. Walking distance to downtown dog friendly restaurants. "
    0
    Flag
  • Topeye
    "The public library across the street and the pedestrian mall 2 blocks away frequently hold community events."
    1
    Flag
  • Juanita e
    "dog owners would love this area great place to live great county sitting quite schools stores dr.s hospital close malls shopping casinos horse racing car raises movies drive in s close tons restaurants parks city county parks swimming snow skiing within hour"
    0
    Flag
  • Andrea
    "Nothing. Nice area not much for kid s to do no playgrounds or nearby parks but nice for adults "
    0
    Flag
  • Destiny W.
    "There's a big Park perfect for taking your dog. Plus you'll see all kinds of dogs being walked downtown on the waking mall. A few businesses even put a water bowl out for the dogs that walk by"
    2
    Flag
  • Debra T.
    "There is a bus stop only a few minutes from my front door. I know you can take the bus down town! I am not sure about long distance travel!"
    1
    Flag
  • Island4tj
    "The city is relatively safe and the schools are very good. Nice, clean town to live in that’s family-oriented. "
    1
    Flag
  • Ruizy8329
    "The neighborhood provides many sidewalks and grassy areas for peaceful and well lit dog walking. People in the area mostly have pets and those who don’t are usually very good about it. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 185 Whimsy Ln

  • What is 185 Whimsy Ln estimated to be worth?
    Trulia's estimated value for 185 Whimsy Ln in Winchester, VA is $589,300.
  • What is the price history for 185 Whimsy Ln?
    185 Whimsy Ln in Winchester, VA last sold for $500,000 in March 2005.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $393K. That is up $3.33K from the prior month.
  • Does 185 Whimsy Ln have air conditioning?
    Yes, 185 Whimsy Ln in Winchester, VA has air conditioning.
  • How big is the lot at 185 Whimsy Ln?
    The lot at 185 Whimsy Ln in Winchester, VA is about 5 acres.

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