260 Windy Pine Dr, Winchester, VA 22603
Property image
Property image
OFF MARKET

$801,400

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,678 sqft (on 5.60 acres)

260 Windy Pine Dr, Winchester, VA 22603

Est. Refi. Payment $4,450/mo*
Refinance Your Home
Currently Off Market - Sold Jul 18, 2024 for $734,825

Home Value

Trulia Estimate
$801K
Since last month
Decreased$12K (-1.5%)
Since last year
Increased$50K (+6.6%)
Since last sale
Increased$68K (+9.2%)
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 +61% in the last 10 years
MonthEstimated value
2026
August 2026$803K
August 2026$801K
July 2026$815K
June 2026$818K
May 2026$815K
April 2026$811K
March 2026$798K
February 2026$786K
January 2026$768K
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
139 Panarama Dr, Winchester, VA
0.83
Single-Family Home
$810,700
08/17/26
4
2.5
3,685
1039 Hiatt Rd, Winchester, VA
1.15
Single-Family Home
$580,000
11/21/25
3
2
3,516
341 Warm Springs Rd, Winchester, VA
0.80
Single-Family Home
$478,000
12/13/25
4
2.5
1,958
2561 Apple Pie Ridge Rd, Winchester, VA
0.43
Single-Family Home
$340,000
08/26/26
3
2
1,412
170 Green Spring Rd, Winchester, VA
1.36
Single-Family Home
$740,000
10/29/25
4
3
2,740
292 Green Spring Rd, Winchester, VA
1.45
Single-Family Home
$700,000
10/29/25
4
4.5
4,320
189 Babbs Mountain Rd, Winchester, VA
1.28
Single-Family Home
$900,000
03/27/26
4
3.5
6,339
891 Payne Rd, Winchester, VA
1.49
Single-Family Home
$618,000
06/08/26
4
3.5
2,849

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
225 Cotton Ridge Rd, Winchester, VA 22603
0.16
$677,300
4
2.5
2,813
Off Market
100 Cotton Ridge Rd, Winchester, VA 22603
0.24
$846,800
4
2.5
3,194
Off Market
2561 Apple Pie Ridge Rd, Winchester, VA 22603
0.43
$340,000
3
2
1,412
Recently Sold
141 Old Baltimore Rd, Winchester, VA 22603
0.48
$870,100
6
3.5
4,682
Off Market
2182 Apple Pie Ridge Rd, Winchester, VA 22603
0.57
-
-
-
-
Off Market
191 Old Baltimore Rd, Winchester, VA 22603
0.59
$1,279,800
6
5.5
6,414
Off Market
111 Dolan Ct, Winchester, VA 22603
0.70
$723,600
4
2.5
3,782
Off Market
420 Tyler Dr, Clear Brook, VA 22624
0.81
$862,600
4
2.5
4,163
Off Market
341 Warm Springs Rd, Winchester, VA 22603
0.80
$478,000
4
2.5
1,958
Recently Sold
185 Panarama Dr, Winchester, VA 22603
0.79
$761,700
5
3.5
3,414
Off Market
139 Panarama Dr, Winchester, VA 22603
0.83
$810,700
4
2.5
3,685
Recently Sold

Local Information

  • Map ViewExplore the area around 260 Windy Pine Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1990
5.6 acre lot
3,678 sqft
$218/sqft
2 Car Garage
HOA $42/mo

About this House

***PUBLIC OPEN HOUSE - SATURDAY JUNE 15 FROM 11 AM - 1 PM - COME OUT AND VISIT THIS LOVELY PROPERTY!*** Location, Location, LOCATION plus a PRICE MODIFICATION! If you are looking for extensive living space THIS IS IT! You will be amazed at the size of the interior rooms which are perfect for the comfort of daily life and all your gatherings - this is a MUST see! You do not want to miss this wonderfully spacious home nestled on 5.6 partially wooded acres in highly desired Cottonwood Subdivision off of Apple Pie Ridge Road! You will definitely enjoy the beautiful scenery of rolling hills of orchards, open fields, and mountain views as you drive to and from Cottonwood. If you're looking to get away from the hustle and bustle of city life, yet you need high speed internet, Wave2Net has installed a fiber optics line that goes up to the property! The open floor plan & ample square footage (3,600+ sq.ft!) will satisfy your entertaining needs, along with the fenced above-ground pool for great summer gatherings! The wrap-around front porch welcomes you as you enter the Foyer with hardwood flooring. The freshly painted formal Living Room has bay windows and glass doors to access the porch and enjoy the views, plus a nice brick fireplace for the chilly days. The spacious Dining Room features formal crown molding, a bay window, and this room can accommodate quite a crowd! The eat-in Kitchen has luxury laminate flooring, some stainless steel appliances, granite countertops, plus a center island providing a good bit of extra cabinets and countertop space. Oh, and let's not forget about the fabulous Family Room that brings in tons of natural light with its many windows and majestic cathedral ceilings, plus the gorgeous floor-to-ceiling stone fireplace and wet bar - this room was made for entertainment! The upper level includes the Primary Bedroom - a wonderful space to relax with cathedral ceilings and hardwood floors (with a decorative inlay) and a huge walk-in closet. The gorgeously updated Primary Bathroom has an extra large tiled shower, luxury vinyl plank flooring, and a double sink vanity with custom built-ins. Three additional bedrooms, a full hall bathroom, and attic access complete the upper level. Now...bring your imagination and finishing touches to the unfinished basement! With 11-foot ceilings, a wood stove, and a rough-in for a future bathroom - imagine the possibilities here! Plus the 2-car garage includes cabinetry for a great workshop area. You will truly love this setting - partially wooded, a back deck that connects to the 25-foot above-ground pool, RING security system, invisible dog fence and a swing set that convey, and so much yard to enjoy! You just can't beat this picturesque and convenient location - just about 10 minutes to Valley Health & medical offices, shopping & restaurants, downtown Winchester, Shenandoah University, Rt 37 and I-81!
260 Windy Pine Dr, Winchester, VA 22603 is a 4 bedroom, 3 bathroom, 3,678 sqft single-family home built in 1990. It last sold for $734,825 on Jul 18, 2024 (2% below the $749,500 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $801,400, with a rent estimate of $3,363/month.
Last check for updates: about 24 hours ago
Listed by Bridget Aikens, (540) 450-3341
Colony Realty
Bought with: Gene Sampson, (703) 217-5716, RE/MAX Real Estate Connections
Source: Bright MLS, MLS#VAFV2018500

Home Details for 260 Windy Pine Dr

Interior Features

Interior Details
Basement: Full,Garage Access,Interior Entry,Exterior Entry,Rough Bath Plumb,Space For Rooms,Unfinished,Walk-Out AccessNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 3678 Square Feet
Appliances & Utilities
Utilities: Satellite Internet Service, Fiber OpticAppliances: Microwave, Dishwasher, Dryer, Oven/Range - Gas, Refrigerator, Stainless Steel Appliance(s), Washer, Water Conditioner - Owned, Water Treat System, Water HeaterDishwasherDryerLaundry: Main Level,Dryer In Unit,Washer In Unit,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Wood Stove,PropaneHas CoolingAir Conditioning: Central Air,Ceiling Fan(s),Attic Fan,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Fireplace: Brick, Flue for Stove, Stone, Wood Burning StoveHas a Fireplace
Windows, Doors, Floors & Walls
Window: Bay/Bow, Window TreatmentsFlooring: Luxury Vinyl, Hardwood, Carpet, Ceramic Tile, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Luxury Vinyl, Hardwood, Carpet, Ceramic Tile, Wood
View
Has a ViewView: Trees/Woods
Security
Security: Security System

Exterior Features

Exterior Home Features
Other Structures: Above Grade, Below GradeFoundation: Active Radon MitigationHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Open Parking Spaces: 6No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 8Parking: Basement,Garage Faces Side,Garage Door Opener,Asphalt,Attached,Driveway
Pool
Pool: Above Ground, PrivatePool
Frontage
Not on Waterfront
Water & Sewer
Sewer: On Site Septic
Finished Area
Finished Area (above surface): 3678 Square Feet

Property Information

Year Built
Year Built: 1990
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Parcel Number: 32 18 5 6

Price & Status

Price
List Price: $749,500
Status Change & Dates
Off Market Date: Fri Jul 19 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: WINCHESTERCommunity: Cottonwood
School Information
Elementary School District: Frederick County Public SchoolsJr High / Middle School District: Frederick County Public SchoolsHigh School District: Frederick County Public Schools

Building

Building Area
Building Area: 5886 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Snow Removal, Road MaintenanceHas an HOAHOA Fee: $500/Annually

Lot Information

Lot Area: 5.6 Acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAFV2018500Above Grade Unfinished Area: 3678

Price and Tax history

DateEventPrice
Jul 18, 2024
Source: Bright MLS #VAFV2018500
Sold
$734,825
Jul 11, 2024
Source: Bright MLS #VAFV2018500
Pending
$749,500
Jun 17, 2024
Source: Bright MLS #VAFV2018500
Contingent
$749,500
May 31, 2024
Source: Bright MLS #VAFV2018500
PriceChange
$749,500
Price decreased by 4%
Apr 29, 2024
Source: Bright MLS #VAFV2018500
Listed For Sale
$780,000

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

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 !"
    5
    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

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Frequently asked questions about 260 Windy Pine Dr

  • What is 260 Windy Pine Dr estimated to be worth?
    Trulia's estimated value for 260 Windy Pine Dr in Winchester, VA is $801,400.
  • What is the price history for 260 Windy Pine Dr?
    260 Windy Pine Dr in Winchester, VA last sold for $734,825 in July 2024.
  • 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 260 Windy Pine Dr have air conditioning?
    Yes, 260 Windy Pine Dr in Winchester, VA has air conditioning.
  • Does 260 Windy Pine Dr have a pool?
    Yes, 260 Windy Pine Dr in Winchester, VA has a pool.

Explore by feature - Pet Friendly

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