27 E Main St, Middletown, MD 21769
OFF MARKET

27 E Main St
Middletown, MD 21769

  • 3 Beds
  • 1.5 Baths
  • 2,448 sqft (on 0.38 acres)

$537,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,223/mo*
Refinance Your Home

$537,100

Trulia Estimate
as of Aug 11, 2026
Est. Refi. Payment $3,223/mo*
Refinance Your Home
3 Beds
1.5 Baths
2,448 sqft
(on 0.38 acres)

Local Information

  • Map ViewExplore the area around 27 E Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1910
Lot Size
0.38 acres
Living Area
2,448 sqft
Price/Sqft
$219

About this House

Victorian home with upgraded kitchen and new but period fireplace. The wood was never painted so the entire house is warm heart pine and oak. There are three large gardens on the lot and a grape pergola that makes a fine frame for a movie screen.
27 E Main St, Middletown, MD 21769 is a 3 bedroom, 2 bathroom, 2,448 sqft single-family home built in 1910. It last sold for $215,000 on Dec 8, 1998. It is currently off market. The Trulia Estimate is $537,100, with a rent estimate of $3,769/month.

Home Details for 27 E Main St

Interior Features

Interior Details
BasementAtticNumber of Rooms: 7Types of Rooms: Walk In Closet, Dining Room, Office
Heating & Cooling
Heating: Radiant, OilHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: SlateExterior: VinylGardenLawnPatioPorch
Parking & Garage
Parking: Off Street

Property Information

Year Built
Year Built: 1910
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.38 acres

Price History for 27 E Main St

DatePriceEventSource
12/08/1998$215,000Sold
N/A
06/08/1995$214,500Sold
N/A

Market trends in Middletown

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
28
7MoM
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Property Tax and Assessment

Year2025
Tax$7,105
Assessment$482,567
Home facts updated by county records

Comparable Sales for 27 E Main St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
124 E Main St, Middletown, MD
0.16
Single-Family Home
$585,000
07/24/26
3
2
2,474
107 Broad St, Middletown, MD
0.20
Single-Family Home
$350,000
09/05/25
3
2.5
2,484
207 Broad St, Middletown, MD
0.25
Single-Family Home
$500,000
03/13/26
4
2
2,210
10 Linden Blvd, Middletown, MD
0.33
Single-Family Home
$480,000
04/17/26
3
1.5
2,104
301 S Jefferson St, Middletown, MD
0.33
Single-Family Home
$445,000
06/23/26
3
2
2,000
206 Prospect St, Middletown, MD
0.21
Single-Family Home
$425,000
10/07/25
4
2
1,954
107 S Jefferson St, Middletown, MD
0.25
Single-Family Home
$435,000
04/21/26
3
2
1,584
16 Linden Blvd, Middletown, MD
0.38
Single-Family Home
$410,900
06/18/26
3
2
1,684
101 Linden Blvd, Middletown, MD
0.42
Single-Family Home
$462,000
11/26/25
3
2
1,812
112 Locust Ct, Middletown, MD
0.48
Single-Family Home
$411,000
06/22/26
3
1.5
1,680

Nearby homes

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Assigned Schools

These are the assigned schools for 27 E Main St.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Middletown

At least 39 Trulia users voted on each feature.

  • 96 % Say yards are well-kept

  • 93 % Say car is needed

  • 89 % Say people would walk alone at night

  • 85 % Say it's dog friendly

  • 83 % Say parking is easy

  • 82 % Say it's quiet

  • 82 % Say there's holiday spirit

  • 73 % Say kids play outside

  • 71 % Say streets are well-lit

  • 70 % Say neighbors are friendly

  • 64 % Say it's walkable to restaurants

  • 58 % Say there are sidewalks

  • 51 % Say they plan to stay for at least 5 years

  • 51 % Say there are community events

  • 47 % Say there's wildlife

  • 44 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Chloe Bishop
    "It’s a nice small-town feel with friendly neighborhoods. Great schools. People are friendly. Close to major highways with minimal traffic compared to Frederick. "
    0
    Flag
  • Trulia User
    "Very quiet, nice neighbors, many of whom grew up in the neighborhood. Siuth Mountain Creamery is a great destination for families, and even delivers. Schools are terrific--the main reason families move and stay here."
    1
    Flag
  • Trulia User
    "Owners are responsible for making sure their dogs are leashed up and under control. Also they pick up after their pets. "
    0
    Flag
  • Trulia User
    "we've lived here for 17 years. neighbors are pleasant and respectful of each otbers privacy. many of them are related, grew up in this neighborhood,(Bolivar). No complaints, except for the cars that speed on the road during rush hour. "
    1
    Flag
  • Trulia User
    "Movie night, Fourth of July celebration, golf course, ice cream parlor, mostly single-family homes, pretty rural,farmers market, good roads, great schools "
    0
    Flag
  • Haileyrockwell
    "Quiet, well kept. everyone is neighborly, small town vibe. Local farmers, schools are close together. "
    0
    Flag
  • Ctauscher10@gmail.com
    "Yes you see dog owners walking their dogs all the time. People are friendly and enjoy being in a rural area. There is also a lot of wildlife here you see deer skunks possums and foxes and I saw a bear once Ion Braddock Heights. You have quick access to interstate 70 east and west."
    0
    Flag
  • Michele M.
    "I often see plenty of dog owners walking their dogs throughout the neighborhood. Many times, you will even find families taking a walk with their pooch. It's a nice little scene. The only problem I think a dog owner might have is if his/her dog has socialization issues. Because they will run into other dogs constantly."
    0
    Flag
  • Graysonramsburg
    "20 minute drive to Frederick... about 12 miles distance. Traffic usually moving but can be heavy during school year."
    0
    Flag
  • Michele M.
    "well kept yards, safe to walk day and night, kid's community sports, award winning schools, quiet community"
    0
    Flag
  • Regis g.
    "amazing schools, great place to raise kids. great family free events all the time, such as movies at the park"
    0
    Flag
  • Gogenevago
    "I just moved here and the neighbors look out for one another. super nice area and I'm glad I own a home in this area. "
    0
    Flag
  • Robynrmason
    "Great school system and safe area. Beautiful views and great community. Very convenient to interstate and to stores. Have lived here 10 years and love it. "
    1
    Flag
  • Dotty D.
    "House is located in Brookridge neighborhood, surrounded by beautiful Wiles Branch Park. Middletown is a wonderful small town community with best schools in the area. "
    1
    Flag
  • mcbee
    "My friends live there on Tobias Run and it's a great street with a hidden open/park like area the size of 2 football fields with a spotless play area, sitting benches, and walking paths all with in 1-2 blocks of the Hollow Creek golf course, club house and Valley Grill restaurant & Sports Bar. There are beautiful views of the golf course and surrounding mountains. Plus, it is serviced by FCPS school buses that bring children to all of Middletown's schools (elementary, middle, high school) ... all of this for a fantastic home and a mere $50 HOA fee!"
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  • Guillermo A. J.
    "WHY IS ANYWHERE IN MIDDLETOWN MD A POOR NEIGHBORHOOD IS BECAUSE THERE NOT ENOUGH PLACES TO WORK @ IN MIDDLETOWN MD BECAUSE YOU DON'T SEE THAT MUCH BUILDING'S IN MIDDLETOWN MD TO WORK @ AS A JOB AND BECAUSE NOBODY IN MIDDLETOWN MD MAKE'S TOO MUCH MONEY AND THERE'S NOT ENOUGH PLACE'S TO EAT @ AND WHOEVER YOU ARE NEVER EVER EVER EVER MOVE TO MIDDLETOWN MD"
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Middletown, MD

Explore by feature - Air Conditioning

8 rentals with air conditioning in Middletown, MD

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Homes for sale near 27 E Main St

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Off Market Homes Near 27 E Main St

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Frequently asked questions about 27 E Main St

  • What is 27 E Main St estimated to be worth?
    Trulia's estimated value for 27 E Main St in Middletown, MD is $537,100.
  • What is the price history for 27 E Main St?
    27 E Main St in Middletown, MD last sold for $215,000 in December 1998.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Middletown?
    Residents describe Middletown, MD as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Middletown, MD.
  • Does 27 E Main St have laundry facilities?
    Yes, 27 E Main St in Middletown, MD has in-unit laundry.
  • How big is the lot at 27 E Main St?
    The lot at 27 E Main St in Middletown, MD is about 0.38 acres (16,606 sq ft).