265 Windsor Ln, Winchester, VA 22602
Property image
Property image
OFF MARKET

$1,333,500

Trulia Estimate
  • 6 Beds
  • 6 Baths
  • 7,435 sqft (on 5.20 acres)

265 Windsor Ln, Winchester, VA 22602

Est. Refi. Payment $7,355/mo*
Refinance Your Home
Currently Off Market - Sold Apr 15, 2021 for $989,000

Home Value

Trulia Estimate
$1.33M
Since last month
Decreased$12K (-0.9%)
Since last year
Increased$24K (+1.8%)
Since last sale
Increased$347K (+35.1%)
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 +114% in the last 10 years
MonthEstimated value
2026
August 2026$1.34M
August 2026$1.33M
July 2026$1.35M
June 2026$1.38M
May 2026$1.35M
April 2026$1.33M
March 2026$1.33M
February 2026$1.3M
January 2026$1.28M
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
1617 Merrimans Ln, Winchester, VA
0.63
Single-Family Home
$1,100,000
07/14/26
4
5
3,877
162 Janes Way, Winchester, VA
1.24
Single-Family Home
$770,000
02/25/26
4
3.5
4,461
2120 Jones Rd, Winchester, VA
0.49
Single-Family Home
$500,000
08/21/26
3
2
2,904
103 Sharon Dr, Winchester, VA
0.82
Single-Family Home
$550,000
01/09/26
5
3
4,047
478 Brookneil Dr, Winchester, VA
1.33
Single-Family Home
$582,500
12/03/25
4
3.5
3,296
137 Stonebrook Rd, Winchester, VA
1.03
Single-Family Home
$705,000
02/03/26
4
4
3,783
140 Stonebrook Rd, Winchester, VA
0.97
Single-Family Home
$677,500
08/27/26
4
3
3,300
111 Garnett Ct, Winchester, VA
1.04
Single-Family Home
$732,000
11/25/25
3
2
2,350
314 Greenfield Ave, Winchester, VA
1.01
Single-Family Home
$576,000
07/13/26
4
2.5
2,520
2285 Jones Rd, Winchester, VA
0.84
Single-Family Home
$372,500
07/10/26
3
2.5
2,192

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
Plow Run, Winchester, VA 22602
0.15
$633,500
3
2
2,103
Off Market
Genessee Trl, Winchester, VA 22602
0.15
$454,600
3
2
1,500
Off Market
Hiawatha Trl, Winchester, VA 22602
0.15
$411,500
3
2.5
1,660
Off Market
Cochise, Winchester, VA 22602
0.15
$505,300
3
2.5
1,660
Off Market
Covey Ln, Winchester, VA 22602
0.15
$661,800
3
2.5
2,216
Off Market
Fall Run Ln, Winchester, VA 22602
0.15
-
-
-
-
Off Market
Mountain Falls Blvd, Winchester, VA 22602
0.15
$484,300
-
-
-
Off Market
Dogwood, Winchester, VA 22602
0.15
$499,600
3
3
1,850
Off Market
Not On File, Winchester, VA 22602
0.15
$366,400
-
-
-
Off Market
Graywolf Trl, Winchester, VA 22602
0.15
$533,300
3
2
1,500
Off Market
Opossum, Winchester, VA 22602
0.15
-
-
-
-
Off Market
Indiana Trl, Winchester, VA 22602
0.15
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 265 Windsor Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1990
5.2 acre lot
7,435 sqft
$179/sqft
Garage

About this House

Welcome to 265 Windsor Lane located in Long Meadows just outside of historic Winchester, VA! You enter the property through brick columns and follow the circular driveway where you will be delighted by the stunning architecture and appreciate the love and care that went into the beautiful landscaping. This home, with over 7400 square feet of finished space on three levels, is filled with light and custom appointments throughout. The stunning foyer with travertine tile and elegant staircase has soaring ceilings and is ideal when greeting your guests. The main-level floorplan includes all the amenities that you're looking for with an open feel that's perfect for entertaining. The gourmet kitchen with high-end appliances is a cook's delight. A two-story family room with tons of windows and a custom stone fireplace with bluestone hearth is designed to enjoy the views year-round from the comfort of your home. The large, main-level owners' suite includes an electric fireplace, custom bath, and for your morning coffee or evening glass of wine, a coffee/wine station. The upper level has a second owners' suite complete with laundry. Five additional bedrooms, two baths, and a loft overlooking the entry foyer and the family room complete the upper level. The lower level has a game room complete with a wet bar, a large exercise room, and an elegant soundproof theatre/media room with granite countertop bar seating that you'll love, all with the fine touches seen throughout the rest of the home. Situated on a gorgeous five-acre lot that is partially forested and bounding with nature provides a true sense of tranquility and the feel of living on a country estate, while only a short drive to Old Town Winchester, the Winchester Hospital Center, and easy access to I81. You will enjoy easy access to nearby orchards and farm-to-table restaurants; short drives to wineries, hiking trails, including the Appalachian Trail, rafting and kayaking, and ski resorts. This special home is one of a kind that must be seen to fully appreciate!
265 Windsor Ln, Winchester, VA 22602 is a 6 bedroom, 7 bathroom, 7,435 sqft single-family home built in 1990. It last sold for $989,000 on Apr 15, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,333,500, with a rent estimate of $4,453/month.

Home Details for 265 Windsor Ln

Interior Features

Interior Details
BasementNumber of Rooms: 13Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, Heat Pump, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: OtherExterior: BrickFoundation Type: Concrete
Parking & Garage
GarageParking Spaces: 7Parking: Garage Attached

Property Information

Year Built
Year Built: 1990
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 5.20 acres

Price and Tax history

DateEventPrice
Apr 16, 2023
Source: Bright MLS #VAFV157774
ListingRemoved
Apr 15, 2021
Source: N/A
Sold
$989,000
Mar 11, 2021
Source: Bright MLS #VAFV157774
Pending
$1,080,000
Feb 22, 2021
Source: Bright MLS #VAFV157774
Contingent
$1,080,000
Dec 4, 2020
Source: Agent Provided
PendingToActive
$1,080,000

Market trends in Winchester

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$390K
$10KMoM
Sale-to-List Price
100.0%
Price per sq ft
$222
$6MoM
Available listings
307
5MoM

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! "
    5
    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."
    11
    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 265 Windsor Ln

  • What is 265 Windsor Ln estimated to be worth?
    Trulia's estimated value for 265 Windsor Ln in Winchester, VA is $1,333,500.
  • What is the price history for 265 Windsor Ln?
    265 Windsor Ln in Winchester, VA last sold for $989,000 in April 2021.
  • Is Winchester a buyer's or seller's market?
    Winchester is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winchester?
    The median sale price in Winchester is $390K. That is up $10K from the prior month.
  • Does 265 Windsor Ln have air conditioning?
    Yes, 265 Windsor Ln in Winchester, VA has air conditioning.
  • Does 265 Windsor Ln have laundry facilities?
    Yes, 265 Windsor Ln in Winchester, VA has in-unit laundry.

Explore by feature - Pet Friendly

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