27 Winchester St, Frederick, MD 21701
OFF MARKET

27 Winchester St
Frederick, MD 21701

  • 2 Beds
  • 2 Baths
  • 875 sqft

$404,200

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,444/mo*
Refinance Your Home

$404,200

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $2,444/mo*
Refinance Your Home
2 Beds
2 Baths
875 sqft

Home Value

Trulia Estimate
$404K
Since last month
Increased$13K (+3.3%)
Since last year
Increased$55K (+15.9%)
Since last sale
Increased$213K (+112.2%)
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 +110% in the last 10 years
MonthEstimated value
2026
August 2026$403K
July 2026$390K
June 2026$388K
May 2026$382K
April 2026$425K
March 2026$424K
February 2026$441K
January 2026$394K
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
70 E South St, Frederick, MD
0.10
Single-Family Home
$415,000
04/06/26
2
1.5
1,108
138 E South St, Frederick, MD
0.06
Single-Family Home
$285,000
07/16/26
2
1
672
226 S Carroll St, Frederick, MD
0.04
Single-Family Home
$355,000
08/28/25
2
1
1,060
313 S Market St, Frederick, MD
0.23
Single-Family Home
$450,000
01/23/26
2
2
1,590
115 Water St, Frederick, MD
0.16
Single-Family Home
$355,000
08/27/25
2
1
900
108 Water St, Frederick, MD
0.18
Single-Family Home
$260,000
05/08/26
1
1
739
7 N Wisner St, Frederick, MD
0.39
Single-Family Home
$345,000
07/15/26
2
1
1,034
210 E 3rd St, Frederick, MD
0.53
Single-Family Home
$335,000
11/04/25
3
1.5
1,200
101 Pennsylvania Ave, Frederick, MD
0.51
Single-Family Home
$310,000
04/24/26
2
2
864
338 E Church St, Frederick, MD
0.48
Single-Family Home
$520,000
04/30/26
2
1.5
1,244

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
29 Winchester St, Frederick, MD 21701
0.00
$385,000
2
1.5
1,064
For Sale
Urner St, Frederick, MD 21701
0.01
-
-
-
-
Off Market
151 Urner St, Frederick, MD 21701
0.01
$723,400
4
3.5
2,113
Off Market
10 Winchester St, Frederick, MD 21701
0.04
$353,200
2
1
1,154
Off Market
246 S Carroll St, Frederick, MD 21701
0.04
$389,700
3
2
2,016
Off Market
248 S Carroll St, Frederick, MD 21701
0.05
$381,200
-
-
-
Off Market
252 S Carroll A St, Frederick, MD 21701
0.06
$755,000
3
4.5
-
Recently Sold
252 S Carroll B St, Frederick, MD 21701
0.06
$800,100
3
4.5
-
Off Market
226 S Carroll St, Frederick, MD 21701
0.04
$354,600
2
1
1,060
Off Market
368 Tiller St, Frederick, MD 21701
0.07
$575,400
4
3.5
1,962
Off Market
364 Tiller St, Frederick, MD 21701
0.07
$548,200
4
3.5
1,962
Off Market
127 Water St, Frederick, MD 21701
0.14
$398,300
2
1.5
1,092
Off Market

Local Information

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

Home Highlights

Property Type
Single-Family Home
Year Built
1910
Living Area
875 sqft
Price/Sqft
$462

About this House

Back on the market! Full baths in both bedrms. Stone walls in landscaped & fenced back yard. 2BR, 2BA detached brick home within walking distance of downtown shops & restaurants, all for under $200k! New dishwasher, HVAC ten yrs old, replacement windows. Walk to MARC shuttle & city park. One way street means less traffic. Private patio great for cookouts.
27 Winchester St, Frederick, MD 21701 is a 2 bedroom, 2 bathroom, 875 sqft single-family home built in 1910. It last sold for $190,000 on Nov 24, 2015. It is currently off market. The Trulia Estimate is $404,200, with a rent estimate of $2,390/month.

Home Details for 27 Winchester St

Interior Features

Interior Details
BasementCeiling Fan
Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3Floors: Other
Appliances & Utilities
DishwasherDryerRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: MetalExterior: Vinyl, BrickPatio

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: 2265 sqft

Price and Tax history

DateEventPrice
Nov 24, 2015
Source: N/A
Sold
$190,000
Oct 10, 2015
Source: Agent Provided
PendingToActive
$189,900
Sep 4, 2015
Source: Agent Provided
Pending
$189,900
Aug 21, 2015
Source: Agent Provided
Listed For Sale
$189,900
Oct 1, 2008
Source: N/A
Sold
$157,500

Market trends in Frederick

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$441K
$7.33KMoM
Sale-to-List Price
100.0%
Price per sq ft
$224
$2MoM
Available listings
547
14MoM

Around this home

What Locals Say about Frederick

At least 861 Trulia users voted on each feature.

  • 90 % Say it's dog friendly

  • 87 % Say there are sidewalks

  • 79 % Say car is needed

  • 77 % Say parking is easy

  • 75 % Say there's holiday spirit

  • 74 % Say streets are well-lit

  • 72 % Say yards are well-kept

  • 71 % Say kids play outside

  • 68 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say it's quiet

  • 62 % Say it's walkable to grocery stores

  • 53 % Say neighbors are friendly

  • 49 % Say they plan to stay for at least 5 years

  • 46 % Say there's wildlife

  • 33 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Jennifer mens
    "Beautiful place nice people nice houses can’t go wrong just watch out for crazy drivers !!!!!!!!!!!!!!!!"
    0
    Flag
  • Jennifer mens
    "Dog owners would like that there’s a lot of other dog walkers and everyone is nice and mostly cleans up after themselves "
    0
    Flag
  • Daniel_davis25
    "They would like that we have dog appointment areas for them to use the restroom. Also they have doggy bags for pickup and disposal receptacles. "
    0
    Flag
  • Libragirl70
    "There are many dog owners here, dog parks and waste receptacles everywhere. Frederick is very dog friendly. "
    1
    Flag
  • Jeffrey A Leon
    "No longer commute as I am retired. But commute to DC is awful as traffic is terrible and horrible all times."
    0
    Flag
  • Angela Alvarez
    "I’ve lived in Urbana for a year and I love it, the swimming pools and gyms are amazing and the trash collection comes twice a week"
    0
    Flag
  • Angela Alvarez
    "Urbana is the best area of Frederick and the best schools too. It has some restaurants and shops too and an international population"
    0
    Flag
  • Angela Alvarez
    "I’ve lived here 2 years and it’s very safe although extremely diverse. It’s got a lot of nationalities "
    0
    Flag
  • amezy
    "I’ve lived here for over 10 years it’s pretty quiet most of the time and most people keep to themselves. Down side is that there’s nothing to do here so it gets pretty boring."
    0
    Flag
  • Jessica Croxall
    "Lots of dog owners in the neighborhood. Dog parks in the neighborhood that have water, room to run free. "
    0
    Flag
  • Abryle Haynes
    "I don’t know. Just make sure your dog is on a leash. Not all dogs are friendly. And you don’t know what your dog is really capable of around strangers and other dogs. "
    0
    Flag
  • Abryle Haynes
    "30 mins to and from Hagerstown and Montgomery county is not bad. But a lot of accidents on 70 and 270, daily. "
    0
    Flag
  • Lgarber626
    "My current neighborhood is nice and the families are friendly. It’s unique because there is more land separating the houses than in other areas of the county. "
    0
    Flag
  • Nadinewilsonsmith
    "The community event that’s makes the neighborhood special are Community Outreach, community events, clubs and church activities. "
    0
    Flag
  • Robin Wilcox
    "We have lived locally for 12 years and love it. I grew up in Montgomery County and love living here in Frederick!"
    0
    Flag
  • Noellauryn2
    "It’s a very safe neighborhood, there’s lots of parks I just find it can be hard to find a lot of kid and teen spaces. I’d recommend making sure your teen has a license I see this as a place to live with young kids!"
    0
    Flag
  • Terrywilson20115
    "Neighborhood is very dog friendly. People are constantly walking dogs of all sizes and breeds. We have a 100 pound Rottweiler and have no issues walking her in the neighborhood. Everyone is good about adhering to the leash laws. For the most part, people are good about cleaning up after their dog."
    4
    Flag
  • Csn45bxxp2
    "There are a lot of dogs and plenty of places to walk dogs in the area. Multiple parks, dog walking stations. Great place for a great dog life."
    1
    Flag
  • Trulia User
    "That people respect each other spaces on the sidewalks, but there is a problem with picking up at the pets. Even though there are receptacles with bags and then hang on waste area for them to put them in, so no need to be lazy."
    5
    Flag
  • Trulia User
    "Close to the interstate and there are lots of alternate routes using side streets, if you don't want to use the interstate. Roads are typically not congested. "
    5
    Flag
  • Trulia User
    "it is amazing great place to raise a family . schools are good and community is very good. all festivals are celebrated in a good way and people are friendly"
    1
    Flag
  • Trulia User
    "This is a diverse area of mostly well maintained homes. Nice families. I love walking the nature trails with my kids and dogs. Fox, owl, heron, deer are common sights. "
    3
    Flag
  • Trulia User
    "Friendly Neighbors and very diverse. Near downtown frederick and great restaurants and shopping centers "
    2
    Flag
  • Trulia User
    "There are events up at the community center and the pole throughout the summer. And then they do a Christmas decoration contest"
    1
    Flag
  • Trulia User
    "neighborhood is very safe, quiet and clean. it is a great place to live and raise kids. it is a family oriented community with nearby parks and trails. "
    2
    Flag
  • Trulia User
    "It has a rural feel but is close to amenities. Wide shoulders allow for nice walking areas. The community center used to be a one room school house and holds many neighborhoods events like pancake breakfasts, craft fairs, barbecues, etc."
    1
    Flag
  • Prince H.
    "Great peaceful environment and atmosphere. Family setting games and sporting events. Great to raise kids and family "
    1
    Flag
  • Fidel V.
    "Good place to live and friendly many communities in this area to help you out and parks are amazing "
    0
    Flag
  • Dmoore202000
    "I have lived here for 2 years., and the Frederick area is a great place to live and raise kids. Frederick for the most part is extremely safe, and the neighbors tend to look out for one another."
    0
    Flag
  • Herrodje
    "Area is extremely safe with plenty of open spaces to play. There is access to a lot of parks and great schools"
    16
    Flag
  • Colleen F.
    "There are many families and fun activities and the parks and recreation facilities are excellent. The library system is also top shelf."
    1
    Flag
  • Tamy W.
    "There can be a lot of traffic in this area so be wary when letting kids run around the neighborhood. "
    0
    Flag
  • Bella M.
    " Frederick has some of the most diverse schools and some of the highest rated academically he would be really smart to put your kids in a school in Frederick"
    1
    Flag
  • Trulia User
    "Difficult no public transportation, have to get ride from work partners. Or Uber which is an unnecessary expense."
    3
    Flag
  • Tiana M.
    "We love the community and family focus. Peaceful, beautiful, and lots to do. Not the best public transportation but the services are expanding. "
    5
    Flag
  • Marcelaweedon
    "I don’t know if any right now, but I wish I did. I would like to be a part of them or start one. I feel like this would be a good way for old and new neighbors to meet each other. My neighbors are friendly to each other. Just don’t see community events happening."
    8
    Flag
  • Eloy G. C.
    "I’ve been just 3 months in so don’t know well the area or the neighbors. It is a very peaceful neighborhood to live in though."
    1
    Flag
  • Keith.kiddy
    "Neighbors get together and drink wine and occasionally have barbecues. Everyone is always looking out for each other "
    6
    Flag
  • Kathy M. M.
    "just moved. not too aware of Community events that they have. I moved from Miami FL to Frederick Maryland for it having a good mixture of city life a quietness, however I yet have much of it to explore "
    1
    Flag
  • Tia B. .
    "Frederick is a lovely historic and diverse community. The people are friendly and helpful. I do old recommend Frederick to anyone looking for a safe and tight knit community. "
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 27 Winchester St

  • What is 27 Winchester St estimated to be worth?
    Trulia's estimated value for 27 Winchester St in Frederick, MD is $404,200.
  • What is the price history for 27 Winchester St?
    27 Winchester St in Frederick, MD last sold for $190,000 in November 2015.
  • Is Frederick a buyer's or seller's market?
    Frederick is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Frederick?
    The median sale price in Frederick is $441K. That is up $7.33K from the prior month.
  • Does 27 Winchester St have air conditioning?
    Yes, 27 Winchester St in Frederick, MD has air conditioning.
  • Does 27 Winchester St have laundry facilities?
    Yes, 27 Winchester St in Frederick, MD has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 27 Winchester St

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