See other homes in:
Primary listing photo
Listing photo 2
Listing photo 3
Listing photo 4
Listing photo 5

258 Chimney Cir, Middletown, VA, 22645

5beds
4baths
3,588sqft
$725,000
$202price/sqft
$4,525/moest. monthly cost
$181,000/yrincome needed

About This Home

Welcome to your dream home in highly sought-after Middletown! Nestled on 2.6 private acres, this stunning colonial offers the perfect blend of space, comfort, and modern upgrades, with 5 bedrooms, 3.5 bathrooms, and over 3,500 finished square feet. From the moment you arrive, the charming full front porch invites you to relax and take in the peaceful surroundings. Step inside to a welcoming foyer that flows effortlessly into a spacious and functional layout, ideal for both everyday living and entertaining. The heart of the home is a beautifully designed country kitchen featuring modern appliances, abundant cabinetry, and generous counter space, perfect for cooking, gathering, and hosting. Just off the kitchen, the cozy family room with fireplace creates a warm and inviting space to unwind. The main level also features a dedicated home office, plus a versatile bonus room that can easily serve as a second office, gym, playroom, craft space, or guest area. Upstairs, the expansive primary suite offers a private retreat with an en-suite bath and ample closet space. Four additional oversized bedrooms, including one with its own en-suite, provide flexibility and comfort for family and guests, along with an additional full bathroom. The unfinished lower level (1,656 sq ft) offers endless potential—create your dream home theater, gym, workshop, or additional living space. Step outside to enjoy your brand new deck, perfect for entertaining, relaxing, or taking in the scenic surroundings. With no HOA and plenty of room to roam, this property offers true freedom for outdoor living. ✨ Major upgrades already done for you: * New HVAC (January 2026) * Brand new deck * New 80-gallon hot water heater * New dog wash station * Newer water treatment system Located just minutes from schools, parks, and commuter routes, this home combines the peace of country living with everyday convenience. This is the one you’ve been waiting for, schedule your private showing today!

Getting Around

0
WalkingCar-Dependent
0
TransitVery Limited Transit
11
BikeSomewhat Bikeable

Schools

4/10
4/10
4/10
Sherando High SchoolGrades 9-126.9 mi

Construction

Condition

  • Property condition: Excellent
  • Year built: 2007

Materials

  • Foundation: Block
  • Roof: Architectural Shingle
  • Construction materials: Vinyl Siding

Type & Style

  • Home type: SingleFamily
  • Architectural style: Colonial
  • Property subType: Single Family Residence

Interior

Appliances

  • Appliances included: Cooktop,Dishwasher,Microwave,Double Oven,Oven,Refrigerator,Stainless Steel Appliance(s),Electric Water Heater
  • Laundry features: Washer/Dryer Hookups Only,Laundry Room

Basement

  • Has basement: Yes
  • Basement: Unfinished

Bedrooms & Bathrooms

  • Bedrooms: 5
  • Bathrooms: 4
  • Full bathrooms: 3
  • 1/2 bathrooms: 1
  • Main level bathrooms: 1

Dining Room

  • Level: Main

Exercise Room

  • Level: Main

Family Room

  • Level: Main

Features

  • Additional Stairway,Soaking Tub,Bathroom - Walk-In Shower,Ceiling Fan(s),Combination Kitchen/Living,Dining Area,Family Room Off Kitchen,Open Floorplan,Kitchen Island,9'+ Ceilings
  • Flooring: Carpet,Engineered Wood,Hardwood
  • Number of fireplaces: 1
  • Fireplace: Yes
  • Finished area below ground: 0
  • Finished area above ground: 3,588

Heating & Cooling

  • Heating features: Central,Forced Air,Electric
  • Cooling features: Central Air,Electric

Interior Area

  • Total structure area: 5,244
  • Total interior livable area: 3,588 sqft

Kitchen

  • Level: Main

Laundry

  • Level: Main

Office

  • Level: Main

Property

Accessibility

  • Accessibility features: None

Details

  • Parcel number: 83 3 2 7
  • Zoning: RA
  • Special condition: Standard
  • Other equipment: None
  • Exclusions: Washer And Dryer,Porch Swing,Refrigerator In Garage

Features

  • Levels: Three
  • Stories: 3
  • Pool features: None
  • Patio & porch: Deck,Porch
  • Exterior features: Extensive Hardscape
  • Fencing: Board

Lot

  • Lot size: 2.60 Acres
  • Features: Cleared,Wooded

Parking

  • Total spaces: 2
  • Parking features: Garage Faces Front,Garage Door Opener,Asphalt,Attached,Driveway
  • Has garage: Yes
  • Attached garage spaces: 2
  • Covered spaces: 2
  • Has uncovered spaces: Yes

Climate Risk is Financial Risk

Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.

Biggest Threats for This Home

  • Strong Wind
    Strong WindModerate
  • Winter Weather
    Winter WeatherModerate

How This Home’s Risks Compare

Strong Wind
Winter Weather

FEMA Declared Disasters Across Virginia Counties

Severe Storm
Winter Storm

Understanding the Costs

Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.

Estimated Costs Today

MonthlyAnnual
Mortgage $3,665$43,980
Home Insurance *$212$2,544
Property Taxes $303$3,636
Electricity $345$4,147
Total$4,525$54,300
*Does not include cost of any FAIR Plan premiums

Income You'd Need if You Spent...

35% on housing$155,142/yr
40% on housing$135,750/yr
45% on housing$120,666/yr

Virginia FAIR Plan Programs

Virginia Property Insurance Association

Covered
WildfireWildfire
Visit Website →
Current Policies
Residential: 22,622Commercial: 503
Total Premiums$20.86M
Total Exposure$4.29B

How Costs Could Change Over Time

Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.

Insurance Growth Rate5-year average: 8.6%
8.6%
0%30.0%
Electricity Growth Rate10-year average: 7.8%
7.8%
0%15.0%
Property Taxes Growth Rate2-year average: -0.9%
-0.9%
0%15.0%
Income Spent on Housing
30%
30%45%

Comparing Against the Market

Price Per Sq Ft

$202This listing

vs Other Active Listings

Avg $/sqft

ZIP 22645$451
Frederick County$200

vs Homes Sold Last Month

Median $/sqft

ZIP 22645$242
Frederick County$208

Current Market Trends

Median Price Per Square Foot

The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.

Historicals for This Listing

Zestimate History ($/sqft)

Price History

DateEventPrice
2026-08-05Contingent$725,000
2026-07-30Listed for sale$725,000
2025-08-19Listing removed$695,000
2025-08-05Listed for sale$695,000
2025-07-31Contingent$695,000
2025-07-03Listed for sale$695,000
2021-09-02Sold$549,900
2021-08-18Pending sale$549,900
2021-07-30Contingent$549,900
2021-07-23Price change$549,900
2021-07-07Price change$559,900
2021-06-15Listed for sale$564,900
2014-12-12Sold$315,000
2014-11-11Pending sale$315,000
2014-10-13Listed for sale$315,000
2014-09-19Pending sale$315,000
2014-09-09Price change$315,000
2014-08-24Listed for sale$335,000
2014-08-01Sold$330,360
2007-01-31Sold$469,000

For Sale by Agent

AgentKristi Cooper
BrokerageRealty ONE Group Old Towne

Similar Homes