PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
---|---|---|---|
219 MILAM DriveWinchester, VAWelcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet nei... |
4 beds | 3 baths | 2,654 sq.ft. |
$468,000 |
Airbnb cash on cash: N/A
|
226 TAGGART DriveWinchester, VAWelcome to 226 Taggart Drive - a sunlit Colonial in the heart of Winchester's sought-after... |
4 beds | 4 baths | 4,411 sq.ft. |
$689,900 |
Airbnb cash on cash: N/A
|
316 VIRGINIA AvenueWinchester, VAWell maintained Colonial offering timeless character and modern potential in the heart of ... |
3 beds | 2 baths | 1,192 sq.ft. |
$338,000 |
Airbnb cash on cash: 6.73%
|
2321 STONERIDGE RoadWinchester, VAMust see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The o... |
4 beds | 3 baths | 3,512 sq.ft. |
$625,900 |
Airbnb cash on cash: N/A
|
109 SHELBY CourtWinchester, VAWelcome to this beautiful colonial home in the sought-after Chapel Hill community. Set on ... |
3 beds | 3 baths | 2,412 sq.ft. |
$489,999 |
Airbnb cash on cash: 4.12%
|
320 LINDEN DRWinchester, VAExperience generational refined living in this stunning luxury home just minutes from Winc... |
4 beds | 3 baths | N/A |
$628,000 |
Airbnb cash on cash: N/A
|
105 BUCKWOOD LaneWinchester, VAEnjoy the ease of one-level living in this spacious 2-bedroom, 2-bath home located in a we... |
2 beds | 2 baths | 1,584 sq.ft. |
$375,000 |
Airbnb cash on cash: 3.1%
|
1332 RAMSEUR LaneWinchester, VAWelcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exte... |
3 beds | 2 baths | 2,648 sq.ft. |
$459,000 |
Airbnb cash on cash: 4.09%
|
127 KINROSS DriveWinchester, VAWelcome to 127 Kinross Dr in Winchester, VA! This spacious 5-bedroom, 3.5-bath home offers... |
5 beds | 4 baths | 3,494 sq.ft. |
$620,000 |
Airbnb cash on cash: N/A
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106 FOXGLOVE DriveWinchester, VAThis 3BD/3.5BA Colonial combines modern upgrades with a versatile layout. The upper level ... |
3 beds | 4 baths | 2,686 sq.ft. |
$459,900 |
Airbnb cash on cash: 4.46%
|
137 STONEBROOK RoadWinchester, VAPerched on an elevated lot, this handsome Colonial provides panoramic views from the spaci... |
4 beds | 4 baths | 3,783 sq.ft. |
$789,900 |
Airbnb cash on cash: N/A
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107 OKEEFE DriveWinchester, VACarpeting has been replaced with rich hardwood flooring on main level. 2020 New HVAC & Roo... |
4 beds | 5 baths | 3,076 sq.ft. |
$569,000 |
Airbnb cash on cash: N/A
|
369 CHARLES StreetWinchester, VAThis two-story home offers classic charm with a covered front porch, fenced backyard, and ... |
3 beds | 2 baths | 1,526 sq.ft. |
$285,000 |
Airbnb cash on cash: 7.81%
|
1950 MELVOR LaneWinchester, VA<html> <head> <title>1950 Melvor Ln</title> <style> body { font-family: sans-serif; margin... |
4 beds | 3 baths | 3,108 sq.ft. |
$685,000 |
Airbnb cash on cash: N/A
|
3980 MIDDLE RoadWinchester, VACustom, all-brick white rambler with a French Country ambience, enjoys boundaries of a lov... |
4 beds | 4 baths | 3,504 sq.ft. |
$765,000 |
Airbnb cash on cash: N/A
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580 N BRADDOCK StreetWinchester, VANow $450,000 - Motivated Sellers + Huge Monthly Savings with 2-1 Rate Buydown! Step inside... |
4 beds | 2 baths | 2,200 sq.ft. |
$475,000 |
Airbnb cash on cash: N/A
|
275 GREENWOOD RoadWinchester, VACharming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access... |
3 beds | 3 baths | 1,732 sq.ft. |
$439,900 |
Airbnb cash on cash: 4.77%
|
1709 REAVES StreetWinchester, VAPlease take off shoes and give feedback. Step into this beautifully cared-for home featuri... |
4 beds | 2 baths | 1,092 sq.ft. |
$435,000 |
Airbnb cash on cash: N/A
|
147 HARVEST RIDGE DriveWinchester, VAWelcome to this meticulously cared for home in the sought-after 55+ community The Village ... |
3 beds | 3 baths | 3,153 sq.ft. |
$655,000 |
Airbnb cash on cash: 2.41%
|
125 CHESHIRE CourtWinchester, VABeautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-s... |
4 beds | 4 baths | 2,261 sq.ft. |
$410,000 |
Airbnb cash on cash: N/A
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242 FOOTSTONE LaneWinchester, VAPeaceful Country Retreat on 4.7 Acres - Minutes from Winchester This private country home ... |
1 beds | 1 baths | 1,348 sq.ft. |
$329,900 |
Airbnb cash on cash: 3.67%
|
510 N LOUDOUN StreetWinchester, VAAll brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD... |
N/A beds | N/A baths | 2,376 sq.ft. |
$450,000 |
Airbnb cash on cash: 1.52%
|
107 LACOSTA CourtWinchester, VA107 Lacosta - Private Retreat in Sought-After Ross Common Nestled on over 2 acres. This st... |
4 beds | 4 baths | 3,888 sq.ft. |
$1,175,000 |
Airbnb cash on cash: N/A
|
2623 MIDDLE RoadWinchester, VAWelcome home to 2623 Middle Rd! Now with a Virtual Tour of this beautiful home! Located ne... |
3 beds | 3 baths | 1,984 sq.ft. |
$515,000 |
Airbnb cash on cash: 3.54%
|
608 GREEN StreetWinchester, VAWelcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 renovated full ba... |
3 beds | 1 baths | 1,040 sq.ft. |
$289,999 |
Airbnb cash on cash: 7.7%
|
2225 HARRISON StreetWinchester, VA2225 Harrison Street located in Winchester, VA. One level living in a home remodeled in th... |
3 beds | 2 baths | 1,300 sq.ft. |
$334,900 |
Airbnb cash on cash: 6.46%
|
201 PARKWAY StreetWinchester, VAFreshly Renovated Charmer in Winchester! Welcome to 201 Parkway Street, a freshly updated ... |
4 beds | 4 baths | 1,627 sq.ft. |
$475,000 |
Airbnb cash on cash: N/A
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511 GROUSE DriveWinchester, VAThis is a fantastic opportunity to purchase a new construction home and have the ability t... |
3 beds | 2 baths | 1,333 sq.ft. |
$319,000 |
Airbnb cash on cash: 6.51%
|
939 WOODLAND AVEWinchester, VAPrice Reduced!!! Need your Own Space? or you're looking to Downsize or Just Starting Out, ... |
2 beds | 2 baths | N/A |
$287,500 |
Airbnb cash on cash: 5.05%
|
100 MAURY WayWinchester, VAWelcome to this Former Model Home for the Grand Nassau Cove model by Ryan Homes - once the... |
3 beds | 3 baths | 1,678 sq.ft. |
$399,990 |
Airbnb cash on cash: 5%
|
513 VAN FOSSEN StreetWinchester, VAWelcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch co... |
4 beds | 3 baths | 2,804 sq.ft. |
$360,000 |
Airbnb cash on cash: N/A
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101 DELAWARE TrailWinchester, VAHuge Price Reduction! Motivated Seller. Fabulous remodel featuring the finest materials fr... |
3 beds | 2 baths | 2,302 sq.ft. |
$489,000 |
Airbnb cash on cash: 4.32%
|
110 CARTER PLWinchester, VAContract fell through! Interest rates have gone down! Extensive Renovations: The home ha... |
5 beds | 3 baths | N/A |
$494,970 |
Airbnb cash on cash: N/A
|
3336 HUNTING RIDGE RoadWinchester, VAIMPROVED PRICE! Come home to this beautifully designed POOL HOUSE featuring 4-bedrooms, 3-... |
4 beds | 3 baths | 3,036 sq.ft. |
$574,900 |
Airbnb cash on cash: N/A
|
1460 PITCOCK LaneWinchester, VAEscape to Your Private Retreat - Just 10 Minutes from Winchester! Don't miss the 3D tour a... |
4 beds | 4 baths | 4,949 sq.ft. |
$1,095,000 |
Airbnb cash on cash: N/A
|
129 INDIANAWinchester, VAI am done! Large lot on private street with valley views and private. HW floors entire mai... |
3 beds | 3 baths | 1,660 sq.ft. |
$389,900 |
Airbnb cash on cash: 5.17%
|
221 CRESTWOOD LaneWinchester, VACharming well maintained corner lot unit in desirable Woodbrook Village 55 and over commun... |
2 beds | 2 baths | 1,384 sq.ft. |
$389,900 |
Airbnb cash on cash: 2.88%
|
126 ARMSTRONG PlaceWinchester, VAAll brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Ma... |
4 beds | 3 baths | 1,617 sq.ft. |
$399,000 |
Airbnb cash on cash: N/A
|
540 MONTICELLO StreetWinchester, VAWelcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Dow... |
N/A beds | N/A baths | 4,396 sq.ft. |
$615,000 |
Airbnb cash on cash: 0.68%
|
121 SWEETBRIAR LaneWinchester, VA"Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors... |
4 beds | 3 baths | 3,442 sq.ft. |
$644,999 |
Airbnb cash on cash: N/A
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There are 141 properties for sale in the city of Winchester . The median list price in Winchester is $449,950 and the average price per square foot is $187. In October 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,528.