106 Doolin Ave, Winchester, VA 22602
Property image
Property image
SOLD
JUN 5, 2026

$685,900

Trulia Estimate
  • 4 Beds
  • 4 Baths
  • 3,616 sqft (on 0.28 acres)

106 Doolin Ave, Winchester, VA 22602

Est. Refi. Payment $3,995/mo*
Refinance Your Home
Currently Off Market - Sold Jun 5, 2026 for $675,500 (1% below list price)

Home Value

Trulia Estimate
$686K
Since last month
Increased$1K (+0.2%)
Since last year
Decreased$16K (-2.3%)
Since last sale
Increased$10K (+1.4%)
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 +53% in the last 10 years
MonthEstimated value
2026
September 2026$685K
August 2026$684K
July 2026$679K
June 2026$677K
May 2026$676K
April 2026$710K
March 2026$712K
February 2026$699K
January 2026$693K
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
132 Cahille Dr, Winchester, VA
0.06
Single-Family Home
$679,900
11/24/25
4
3.5
4,167
219 Taggart Dr, Winchester, VA
0.05
Single-Family Home
$905,264
11/20/25
4
3
3,675
229 Taggart Dr, Winchester, VA
0.12
Single-Family Home
$817,252
09/02/26
4
3
3,250
140 Cahille Dr, Winchester, VA
0.12
Single-Family Home
$640,000
08/03/26
4
3
3,005
210 Darby Dr, Winchester, VA
0.36
Single-Family Home
$675,000
10/24/25
4
3.5
2,954
135 Kinross Dr, Winchester, VA
0.28
Single-Family Home
$785,000
08/27/26
4
3
3,366
140 Kinross Dr, Winchester, VA
0.25
Single-Family Home
$601,000
09/30/25
4
2.5
2,926
128 Poe Dr, Winchester, VA
0.35
Single-Family Home
$640,000
05/12/26
4
3.5
3,490
103 Derrynan Ct, Winchester, VA
0.24
Single-Family Home
$740,000
11/07/25
4
3
2,731

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
207 Taggart Dr, Winchester, VA 22602
0.03
$704,500
4
3.5
3,511
Off Market
304 Summerfield Dr, Winchester, VA 22602
0.09
$821,900
5
3.5
3,894
Off Market
302 Summerfield Dr, Winchester, VA 22602
0.10
$797,300
5
3.5
4,058
Off Market
234 Summerfield Dr, Winchester, VA 22602
0.07
$665,200
4
3
2,732
Off Market
219 Taggart Dr, Winchester, VA 22602
0.05
$942,400
4
3
3,675
Off Market
132 Cahille Dr, Winchester, VA 22602
0.06
$679,900
4
3.5
4,167
Recently Sold
134 Cahille Dr, Winchester, VA 22602
0.07
$688,400
4
2.5
2,686
Off Market
222 Summerfield Dr, Winchester, VA 22602
0.07
$629,900
3
2
2,077
For Sale
303 Summerfield Dr, Winchester, VA 22602
0.12
$852,900
4
3.5
3,200
Off Market
131 Cahille Dr, Winchester, VA 22602
0.09
$764,100
6
6
5,045
Off Market
136 Cahille Dr, Winchester, VA 22602
0.08
$739,900
5
4.5
4,731
For Sale

Local Information

  • Map ViewExplore the area around 106 Doolin Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2006
0.28 acre lot
3,616 sqft
$187/sqft
2 Car Garage
HOA $8/mo

About this House

Awarded “Home of the Year” in the prestigious Top of Virginia Homebuilders Association Parade of Homes, this extraordinary sun-drenched estate offers over 3,600 square feet of refined living space on a premier corner lot, with additional unfinished areas ready to be transformed into even more luxury living. Enhanced with fully insulated vinyl siding, the home combines timeless elegance with exceptional energy efficiency and low-maintenance luxury........................................................................................................................................ The upper level features four spacious bedrooms and three beautifully renovated full baths, highlighted by an exceptional owner’s retreat with gleaming hardwood floors, an oversized custom walk-in closet, and a lavish spa-inspired bath. Enjoy dual vanities, a jetted soaking tub, an expansive walk-in shower, a separate water closet, and a dramatic double-sided fireplace shared between the bedroom and bath, creating the perfect private sanctuary. A private princess suite includes brand-new carpeting and its own en-suite bath, while two additional generously sized bedrooms, an updated full bath, and a thoughtfully designed upper-level laundry room with utility sink complete the level........................................................................................................... Designed for both elegant entertaining and everyday comfort, the main level showcases rich hardwood flooring throughout the study, formal dining room, and expansive great room. At the heart of the home is a chef-inspired gourmet kitchen featuring high-end stainless steel appliances, a large center island, double wall ovens, gas cooktop, custom finishes, and seamless flow into the inviting family space anchored by a stunning stone fireplace. Step outside to the covered porch accessible from both the great room and dining room, or unwind in the beautifully landscaped backyard with an elegant patio setting....................................... The walk-up lower level offers an expansive recreation room with bar area, an additional half bath, and abundant unfinished space ideal for a future home theater, fitness studio, wine cellar, or guest suite — allowing you to further customize this spectacular residence to your lifestyle.
106 Doolin Ave, Winchester, VA 22602 is a 4 bedroom, 5 bathroom, 3,616 sqft single-family home built in 2006. It last sold for $675,500 on Jun 5, 2026 (1% below the $679,950 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $685,900, with a rent estimate of $3,177/month.
Last check for updates: about 19 hours ago
Listed by Christine Oberhelman, (703) 216-3005
RE/MAX Allegiance
Bought with: Kaylynn Semple, (540) 422-5328, Pearson Smith Realty LLC
Source: Bright MLS, MLS#VAFV2041470

Home Details for 106 Doolin Ave

Interior Features

Interior Details
Basement: Full,Connecting Stairway,Walk-Out Access,Sump Pump,Windows,Partially Finished,Space For RoomsNumber of Rooms: 13Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Dining Room, Foyer, Great Room, Kitchen, Laundry, Other, Recreation Room, Storage Room, Study
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 3616 Square Feet
Appliances & Utilities
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Energy Efficient Appliances, Ice Maker, Microwave, Double Oven, Self Cleaning Oven, Oven, Refrigerator, Washer, Water Dispenser, Water Heater, Gas Water HeaterDishwasherDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,Natural GasHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,ElectricHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Spa: BathHas a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Low Emissivity Windows, Screens, Window TreatmentsDoor: Atrium, InsulatedFlooring: Ceramic Tile, Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 3Levels: ThreeAccessibility: NoneFloors: Ceramic Tile, Hardwood, Wood
View
No View
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Patio, PorchOther Structures: Above Grade, Below GradeExterior: Sidewalks, Street LightsFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Garage Door Opener,Garage Faces Side,Driveway,Concrete,On Street,Attached
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3216 Square FeetFinished Area (below surface): 400 Square Feet

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Condition: ExcellentNot Included in Sale: Garage ItemsIncluded in Sale: Grandfather Clock, Dining Table, Chairs And HutchParcel Number: 64G3684

Price & Status

Price
List Price: $679,950Price Per Sqft: $187/sqft
Status Change & Dates
Off Market Date: Wed Jun 10 2026Possession Timing: Close Of Escrow, Negotiable

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: WINCHESTERCommunity: Raven Pointe
School Information
Elementary School: EvendaleElementary School District: Frederick County Public SchoolsJr High / Middle School: Admiral Richard E. ByrdJr High / Middle School District: Frederick County Public SchoolsHigh School: MillbrookHigh School District: Frederick County Public Schools

Building

Building Details
Builder Name: TRM CONSTRUCTION, INC.
Building Area
Building Area: 4676 Square Feet

Community

Not Senior Community

HOA

HOA Fee Includes: Common Area MaintenanceHOA Name: RAVEN POINTEHas an HOAHOA Fee: $100/Annually

Lot Information

Lot Area: 0.28 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, FHA, Conventional, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: VAFV2041470Above Grade Unfinished Area: 3216

Additional Information

Source Internet Entire Listing Display: Y

Price and Tax history

DateEventPrice
Jun 5, 2026
Source: Bright MLS #VAFV2041470
Sold
$675,500
May 26, 2026
Source: Bright MLS #VAFV2041470
Pending
$679,950
May 7, 2026
Source: Bright MLS #VAFV2041470
Listed For Sale
$679,950
Jan 5, 2012
Source: Agent Provided
ListingRemoved
$480,000
Dec 31, 2011
Source: Agent Provided
PriceChange
$480,000
Price increased by 300%

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

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! "
    7
    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."
    13
    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

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 106 Doolin Ave

  • What is 106 Doolin Ave estimated to be worth?
    Trulia's estimated value for 106 Doolin Ave in Winchester, VA is $685,900.
  • What is the price history for 106 Doolin Ave?
    106 Doolin Ave in Winchester, VA last sold for $675,500 in June 2026.
  • 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 106 Doolin Ave have air conditioning?
    Yes, 106 Doolin Ave in Winchester, VA has air conditioning.
  • Does 106 Doolin Ave have laundry facilities?
    Yes, 106 Doolin Ave in Winchester, VA has in-unit laundry.

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