305 E Main St, Middletown, MD 21769
Property image
Property image
SOLD
SEP 25, 2026

$695,000

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 3,000 sqft (on 0.60 acres)

305 E Main St, Middletown, MD 21769

Est. Refi. Payment $4,442/mo*
Refinance Your Home
Currently Off Market - Sold Sep 25, 2026 for $695,000 (7% above list price)

Home Value

Trulia Estimate
$695K
Since last month
Increased$64K (+10.1%)
Since last year
Increased$56K (+8.8%)
Since last sale
$100 (0%)
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 +75% in the last 10 years
MonthEstimated value
2026
October 2026$695K
September 2026$695K
August 2026$631K
July 2026$632K
June 2026$645K
May 2026$666K
April 2026$658K
March 2026$649K
February 2026$628K
January 2026$634K
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
124 E Main St, Middletown, MD
0.21
Single-Family Home
$585,000
07/24/26
3
2
2,474
216 E Main St, Middletown, MD
0.16
Single-Family Home
$810,000
06/29/26
5
5
3,296
106 Prospect St, Middletown, MD
0.32
Single-Family Home
$651,000
08/14/26
3
1.5
1,734
10 Linden Blvd, Middletown, MD
0.23
Single-Family Home
$480,000
04/17/26
3
1.5
2,104
100 Lombardy Dr, Middletown, MD
0.32
Single-Family Home
$545,000
03/31/26
3
2
2,372
101 Linden Blvd, Middletown, MD
0.21
Single-Family Home
$462,000
11/26/25
3
2
1,812
2 Lombardy Dr, Middletown, MD
0.26
Single-Family Home
$499,999
06/24/26
3
2
2,079
215 Broad St, Middletown, MD
0.44
Single-Family Home
$560,000
04/09/26
4
3
2,580
9 Caroline Dr, Middletown, MD
0.36
Single-Family Home
$585,000
10/30/25
4
2.5
2,616

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
101 Green St, Middletown, MD 21769
0.08
$350,500
Studio
1
1,664
Off Market
105 Green St, Middletown, MD 21769
0.08
$307,300
Studio
1
864
Off Market
309 E Main St, Middletown, MD 21769
0.09
$690,300
4
2
3,486
Off Market
313 E Main St, Middletown, MD 21769
0.09
$741,200
5
3.5
3,384
Off Market
221 E Main St, Middletown, MD 21769
0.10
-
-
-
-
Off Market
301 E Main St, Middletown, MD 21769
0.10
$264,600
Studio
1
1,159
Off Market
401 E Main St, Middletown, MD 21769
0.10
$1,056,200
4
4
4,500
Off Market
301 E Main St, Burkittsville, MD 21769
0.10
$478,000
Studio
2
2,160
Off Market
221 E Main St, Middletown, MD 21769
0.11
$388,300
2
-
1,500
Off Market
221 E Main St #2, Middletown, MD 21769
0.11
-
1
2
1,500
Off Market
405 E Main St, Middletown, MD 21769
0.11
$755,300
2
1
2,206
Off Market
219 E Main St, Middletown, MD 21769
0.11
$471,300
Studio
2
2,476
Off Market
217 E Main St, Middletown, MD 21769
0.13
$439,600
5
3.5
1,688
Off Market
217 E Main St, Middletown, MD 21769
0.13
-
-
-
-
Off Market
2 Woodmere Cir, Middletown, MD 21769
0.13
$1,000,600
4
5
5,860
Off Market
409 E Main St, Middletown, MD 21769
0.14
$999,400
Studio
3
3,159
Off Market
3 Woodmere Cir, Middletown, MD 21769
0.14
$899,500
5
4.5
6,144
Off Market
4 Woodmere Cir, Middletown, MD 21769
0.14
$989,300
4
4.5
4,500
Off Market
1 Woodmere Cir, Middletown, MD 21769
0.14
$1,103,400
4
6
5,844
Off Market
304 E Main St, Middletown, MD 21769
0.15
$788,900
4
3
3,262
Off Market

Local Information

  • Map ViewExplore the area around 305 E Main St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1913
0.6 acre lot
3,000 sqft
$232/sqft
Garage

About this House

Step into timeless charm without leaving behind today's comforts. This distinctive Painted Lady captures the character, craftsmanship, and gracious proportions that make a home truly memorable, right in the heart of Middletown. Set well back from historic Main Street behind an expansive front lawn, the home has an impressive presence, with a wide wraparound porch inviting you to sit awhile and enjoy the rhythm of small-town living. Located within the sought-after Middletown school district, this is a home that feels a part of the town’s story. Offering over 3,000 finished square feet above grade, the home has been lovingly cared for by the same owners since 1997. Natural light and tall ceilings on every level create a remarkably open and airy feel, while fresh paint complements the beautiful architectural details throughout. An impressive entry foyer sets the tone with original millwork and wood floors, fireplace mantels, pocket doors, a built-in bookcase, and a distinctive split staircase. Stacked bay windows on separate levels feature diamond-pattern divided-light upper sashes and clear glass below—one of the many details that makes this home so special. The spacious front living room features custom built-ins, a fireplace, and pocket doors connecting both the foyer and dining room. The large dining room is ready for holidays, celebrations, and everyday dinners, with a side door opening directly onto the wraparound porch. The updated kitchen blends classic character with modern function, featuring a large center island, wall oven, cooktop, built-in cabinetry, and a charming original pass-through cupboard. A mudroom provides a practical everyday entrance and access to the covered rear porch, while a main-level half bath adds convenience. Upstairs are three generously sized bedrooms, including a spacious primary suite with a private full bath, plus an additional hall bath. An open loft area provides flexible space for an office, study, reading nook, or sitting area. The completely remodeled finished third floor adds another exceptional level of living space, with tall ceilings, abundant natural light, a large recreation room, separate den, and laundry area. Use it as an office, studio, exercise space, media room, hobby room, or private retreat. A unique glass-floor feature allows light to pass through and adds an unexpected architectural element. Outside, there is room to breathe—something increasingly difficult to find right in the heart of town. The large, level property stretches from Main Street to Green Street with access from both streets, offering an expansive front lawn and spacious backyard. A detached one-car garage adds convenience, while eligibility for future subdivision through the Town of Middletown adds another unique dimension. Additional features include air conditioning, radiator heat, updated electrical, a clean unfinished basement for utility and storage, and eligibility for a one-year home warranty. Perhaps what makes this home most memorable is simply the feeling of it—the sunlight, tall ceilings, warmth of the wood floors, beautiful architectural details, and the ability to step onto that wonderful wraparound porch and watch Main Street go by. Filled with charm and personality, yet offering the light, space, and functionality for the way we live today, this gracious Painted Lady is ready for its next chapter.
305 E Main St, Middletown, MD 21769 is a 3 bedroom, 3 bathroom, 3,000 sqft single-family home built in 1913. It last sold for $695,000 on Sep 25, 2026 (7% above the $650,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $695,000, with a rent estimate of $4,240/month.
Last check for updates: about 3 hours ago
Listed by Bobbi Prescott, (301) 514-6163
RE/MAX Results
Listing Team: Bobbi Prescott & Associates
Bought with: Leslie Wheatley, (240) 934-0101, RE/MAX Results
Source: Bright MLS, MLS#MDFR2088606

Home Details for 305 E Main St

Interior Features

Interior Details
Basement: Partial
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 3000 Square Feet
Appliances & Utilities
Appliances: Stainless Steel Appliance(s), Refrigerator, Cooktop, Oven, Dishwasher, Disposal, Washer, Dryer, Electric Water HeaterDishwasherDisposalDryerLaundry: Upper LevelRefrigeratorWasher
Heating & Cooling
Heating: Radiator,OilHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Radiator
Fireplace & Spa
Number of Fireplaces: 1Fireplace: CornerHas a Fireplace
Windows, Doors, Floors & Walls
Window: Bay/BowFlooring: Hardwood, Wood
Levels, Entrance, & Accessibility
Stories: 4Levels: FourAccessibility: NoneFloors: Hardwood, Wood
View
No View

Exterior Features

Exterior Home Features
Roof: SlatePatio / Porch: PorchOther Structures: Above GradeExterior: SidewalksFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1Open Parking Spaces: 6No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 7Parking: Garage Faces Front,Driveway,Detached
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 3000 Square Feet

Property Information

Year Built
Year Built: 1913
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Colonial
Building
Construction Materials: Wood SidingNot a New Construction
Property Information
Condition: ExcellentParcel Number: 1103130002Additional Parcels Description: Property is eligible for further subdivision with the town.

Price & Status

Price
List Price: $650,000Price Per Sqft: $232/sqft
Status Change & Dates
Off Market Date: Fri Sep 25 2026Possession Timing: Seller Rent Back

Active Status

MLS Status: CLOSED

Media

Location

Direction & Address
City: MIDDLETOWNCommunity: Middletown
School Information
Elementary School: MiddletownElementary School District: Frederick County Public SchoolsJr High / Middle School: MiddletownJr High / Middle School District: Frederick County Public SchoolsHigh School: MiddletownHigh School District: Frederick County Public Schools

Building

Building Area
Building Area: 3000 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.60 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To Sell

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDFR2088606Municipality: MiddletownAbove Grade Unfinished Area: 3000

Additional Information

Source Internet Automated Valuation Display: YSource Internet Consumer Comment: YSource Internet Entire Listing Display: YSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Sep 25, 2026
Source: Bright MLS #MDFR2088606
Sold
$695,000
Nov 24, 1997
Source: N/A
Sold
$232,900

Market trends in Middletown

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
6MoM

Around this home

What Locals Say about Middletown

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 82% say there's holiday spirit
  • 70% say neighbors are friendly
  • 58% say there are sidewalks
Trulia Trick or TreatStart Ghost Hunt
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!"
    0
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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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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 305 E Main St

  • What is 305 E Main St estimated to be worth?
    Trulia's estimated value for 305 E Main St in Middletown, MD is $695,000.
  • What is the price history for 305 E Main St?
    305 E Main St in Middletown, MD last sold for $695,000 in September 2026.
  • Is Middletown a buyer's or seller's market?
    Middletown is currently a buyer'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 305 E Main St have air conditioning?
    Yes, 305 E Main St in Middletown, MD has air conditioning.
  • Does 305 E Main St have laundry facilities?
    Yes, 305 E Main St in Middletown, MD has in-unit laundry.

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