Rent pulse
Typical asking rent$1,707a month in Winchester city
1-year change+2.5%
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed, Winchester city figure. Data through September 2026.
9 property managers in Winchester
Tick Compare on up to 3 companies to see them side by side and request quotes from all of them at once.
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MAP Property Solutions
123 S Loudoun St Ste C, Winchester, VA 22601
MAP Property Solutions is a Winchester company managing residential homes in Northern Virginia, Winchester and the West Virginia Eastern Panhandle, with marketing, resident screening, rent collection, maintenance, inspections, financial reporting, evictions and sales.
In their words: “We provide full-service solutions for rental owners in Virginia & West Virginia.”
Review summary: Reviewers often mention a reliable, knowledgeable manager who keeps up with rental needs and cares for owners' homes.
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OakCrest Properties
126 N Kent St, Winchester, VA 22601
OakCrest Properties is a Winchester company offering rental properties, including townhouses, and property management for residents in the Winchester area.
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Coldwell Banker Premier Property Management
1682 S Pleasant Valley Rd, Winchester, VA 22601
Coldwell Banker Premier Property Management is a Winchester office managing residential and vacation rentals, with leasing, marketing, tenant screening, maintenance coordination, inspections and rent collection for owners and investors.
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Property Management 101
9 N Loudoun St, Winchester, VA 22601
Property Management 101 is a Winchester company managing residential rentals, including apartments, in Winchester, the Shenandoah Valley and Northern Virginia, with leasing, maintenance requests and an owner portal.
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ERA OakCrest Realty Rental Management Division
126 N Kent St, Winchester, VA 22601
ERA OakCrest Realty Rental Management Division is the Winchester rental division of ERA OakCrest Realty, handling leasing, tenant services, owner statements and online rent payment for rental homes.
In their words: “We know what to do, and what not to do, to accomplish your rental investment goals.”
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J. Carlin Management
1803 Henry Ave Ste B, Winchester, VA 22601
J. Carlin Management is a Winchester company managing rental homes, handling rent collection, maintenance and repairs, tenant screening and day-to-day tenant issues for owners.
In their words: “As your property management company, we deal with tenant issues, collect rent, handle maintenance and repairs, and qualify new tenants.”
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Covenant Real Estate Management
1822 Roberts St, Winchester, VA 22601
Covenant Real Estate Management is a full-service property management company based in Winchester serving the Shenandoah Valley, handling leasing, maintenance requests and rent payment for residential rentals.
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The Pifer Companies
1 W Gerrard St, Winchester, VA 22601
The Pifer Companies is a Winchester firm managing residential, multifamily, office, retail and light commercial property across the Shenandoah Valley and Northern Virginia, with leasing, tenant placement, maintenance, renovations and financial reporting.
In their words: “Based in Winchester, we serve property owners and investors throughout the Shenandoah Valley and surrounding Northern Virginia markets.”
Review summary: Reviewers often mention friendly, responsive managers and timely repairs, for both residents and landlords with several properties.
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Olive Tree Property Group
2019 S Loudoun St, Winchester, VA 22601
Olive Tree Property Group is a Winchester real estate company offering sales and third-party rental management for property owners in Winchester and the surrounding area.
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Pins show office addresses; numbers match the Best match order. Companies that don't publish an address are listed as "Serves the Winchester area" and get no pin.
Winchester rental market
Get the latest rental and real estate data on the Winchester market. We update these charts with the latest data on the 22nd of each month. Zillow has no figure for Winchester itself, so these are Winchester city figures.
12-month momentum
Rent rose in 7 of the last 12 months: +$41 in all since Oct 2025.
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Green: rent went up that month. Grey: it went down.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed, Winchester city figure. Data through September 2026.
Rent over time
Winchester city
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed, Winchester city figure. Data through September 2026.
Best months to list
Rents here usually rise most in January, March and May, so those are good months to list your rental.
- Jan+1.11%
- Feb+0.50%
- Mar+1.43%
- Apr+0.93%
- May+1.47%
- Jun+0.90%
- Jul+0.73%
- Aug+0.19%
- Sep−0.40%
- Oct−0.84%
- Nov−0.55%
- Dec−0.62%
Average change from the month before, 4 years of data.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed, Winchester city figure. Data through September 2026.
Rental income growth calculator
Past growth, not a forecast. Rents can go down as well as up. Your own rent depends on the home, its condition and the lease.
Source: Zillow Observed Rent Index (ZORI), typical asking rent, all homes + multifamily, smoothed, Winchester city figure. Data through September 2026.
Rent in nearby cities
| City | Typical rent | 1 year | Managers |
|---|---|---|---|
| Front Royal | $1,944 | +1.6% | 4 |
| Leesburg | $2,431 | +3.7% | 6 |
| Warrenton | $2,237 | 15 | |
| Ashburn | $2,934 | +0.3% | 5 |
| Chantilly | $3,108 | +3.1% | 5 |
| Herndon | $2,382 | +1.0% | 4 |
Source: Zillow Observed Rent Index (ZORI), typical asking rent, data through September 2026. Managers listed: our directory, October 2026.
More local facts for owners
Renters and vacancy
56.4%of homes in Winchester are rented (6,481 households)
- Rental vacancy rate
- 4.1%
- County vacancy rate
- 4.1%
- Median rent paid
- $1,315
- Median home value
- $343,000
Source: U.S. Census Bureau, American Community Survey 5-year estimates, 2020-2024.
HUD Fair Market Rents
Source: U.S. Department of Housing and Urban Development, Fair Market Rents for fiscal year 2027, Winchester, VA-WV MSA. Used to set Housing Choice Voucher (Section 8) limits.
Where Winchester managers also work
Areas the companies on this page list on their own websites. Linked places have their own page.
- Northern Virginia 3
- Shenandoah Valley 2
Questions to ask before you hire
Ask every manager the same questions and get the answers in writing, so you can compare quotes fairly.
Tick them off as you go. Nothing here is saved or sent.
Property management in Winchester
Compare the 9 property management companies in Winchester, Winchester city. Tick up to 3 to see them side by side, then request free quotes from all of them in one step.
Zillow has no rent figure for Winchester itself. Zillow's typical asking rent in Winchester city as a whole is $1,707 (September 2026); +2.5% over the past year. About 56.4% of homes in Winchester are rented, and the rental vacancy rate is 4.1% (Census, 2020-2024).
Winchester property management FAQ
How many property management companies are in Winchester?
We list 9 property management companies in Winchester, VA.
What is the typical rent in Winchester?
Zillow's typical asking rent in Winchester city (Zillow has no figure for Winchester itself) was $1,707 a month in September 2026, +2.5% on a year earlier.
When is the best time to list a rental in Winchester?
Over the 4 years Zillow has tracked, asking rents here have risen most in January, March and May. Listing in those months can help, but every property is different.
How much do property managers charge in Winchester?
Fees depend on the company, the property and the services you need, and few companies publish them. Ask for a written quote that lists the monthly fee, leasing fee and any other charges. You can request quotes from up to 3 managers at once on this page.
How do you rank the companies?
The default order, Best match, uses each company's Google rating adjusted for how many reviews it has, so a 4.8 rating from 100 reviews ranks above a 5.0 from 2. No company can pay for its position.
Is it free to request quotes?
Yes. Requesting quotes is free for property owners and there is no obligation to hire anyone.