404 High St, New Windsor, MD 21776
OFF MARKET

$515,400

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,218 sqft (on 0.43 acres)

404 High St, New Windsor, MD 21776

Est. Refi. Payment $3,093/mo*
Refinance Your Home
Currently Off Market - Sold Aug 4, 2008 for $399,900

Home Value

Trulia Estimate
$515K
Since last month
Decreased$8K (-1.6%)
Since last year
Decreased$2K (-0.4%)
Since last sale
Increased$116K (+28.9%)
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 +61% in the last 10 years
MonthEstimated value
2026
August 2026$515K
July 2026$524K
June 2026$531K
May 2026$527K
April 2026$510K
March 2026$501K
February 2026$484K
January 2026$494K
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
414 High St, New Windsor, MD
0.07
Single-Family Home
$464,000
06/15/26
3
2.5
2,668
296 Lambert Ave, New Windsor, MD
0.11
Single-Family Home
$440,000
09/08/25
3
3
2,357
205 Church St, New Windsor, MD
0.08
Single-Family Home
$730,000
10/29/25
4
3
4,386
3238 Atlee Ridge Rd, New Windsor, MD
0.46
Single-Family Home
$500,000
06/08/26
4
3
1,959
3190 Vista Ct, New Windsor, MD
0.40
Single-Family Home
$430,000
05/21/26
3
2.5
1,892
3169 Vista Ct, New Windsor, MD
0.29
Single-Family Home
$435,000
10/03/25
4
2
1,268
1205 Jo Apter Pl, New Windsor, MD
0.45
Single-Family Home
$447,500
10/24/25
5
3
2,110
306 College Ave, New Windsor, MD
0.26
Single-Family Home
$395,000
12/19/25
3
2
2,258
2832 Graybill Ct, New Windsor, MD
0.55
Single-Family Home
$590,000
04/30/26
4
2.5
2,548
124 Church St, New Windsor, MD
0.13
Single-Family Home
$350,000
08/20/26
3
3
1,736

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
312 High St, New Windsor, MD 21776
0.02
$612,400
3
2.5
3,119
Off Market
201 Maple Ave, New Windsor, MD 21776
0.02
$464,200
4
3
2,478
Off Market
205 Church St, New Windsor, MD 21776
0.08
$746,100
4
3
4,386
Off Market
414 High St, New Windsor, MD 21776
0.07
$464,000
3
2.5
2,668
Recently Sold
117 Church St, New Windsor, MD 21776
0.11
$359,700
5
-
2,772
Off Market
126 Church St, New Windsor, MD 21776
0.12
$421,700
7
-
3,384
Off Market
211 Church St, New Windsor, MD 21776
0.10
$416,200
5
3
3,063
Off Market
120 Church St, New Windsor, MD 21776
0.13
$505,700
4
2.5
2,523
Off Market
124 Church St, New Windsor, MD 21776
0.13
$350,000
3
3
1,736
Recently Sold
210 High St, New Windsor, MD 21776
0.13
$359,800
3
1.5
1,733
Off Market
296 Lambert Ave, New Windsor, MD 21776
0.11
$450,800
3
3
2,357
Off Market
106 Church St, New Windsor, MD 21776
0.16
$308,900
4
2
1,609
Off Market

Local Information

  • Map ViewExplore the area around 404 High St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1860
0.43 acre lot
3,218 sqft
$160/sqft
Garage

About this House

Ante Bellum treasure in historic community.This lovely lady sits among her sisters in proud historic charm, combining period ambience with modern updates of plumbing, electric, roof, Kitchen, Master Bath and some windows. Magnificant gardens feature flowers, fruit & nut trees, koi pond and shed.Large rooms exhibit the spaciousness of the home;porches abound-open, screened, closed-in.Village Zoning
404 High St, New Windsor, MD 21776 is a 4 bedroom, 3 bathroom, 3,218 sqft single-family home built in 1860. It last sold for $399,900 on Aug 4, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $515,400, with a rent estimate of $1,621/month.

Home Details for 404 High St

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: RadiantHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Brick
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1860
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.43 acres

Price and Tax history

DateEventPrice
Aug 4, 2008
Source: N/A
Sold
$399,900
Apr 16, 2008
Source: Agent Provided
Listed For Sale
$399,900

Market trends in New Windsor

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
23

Around this home

What Locals Say about New Windsor

At least 17 Trulia users voted on each feature.

  • 100 % Say yards are well-kept

  • 95 % Say it's dog friendly

  • 95 % Say car is needed

  • 86 % Say parking is easy

  • 79 % Say there are sidewalks

  • 73 % Say it's quiet

  • 71 % Say people would walk alone at night

  • 71 % Say there's holiday spirit

  • 71 % Say kids play outside

  • 70 % Say streets are well-lit

  • 59 % Say there's wildlife

  • 58 % Say neighbors are friendly

  • 44 % Say it's walkable to restaurants

  • 41 % Say they plan to stay for at least 5 years

  • 26 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Charlene C.
    "New Windsor is a wonderful small town however the water prices are ridiculous and drives many people away "
    0
    Flag
  • Jgmeerdter
    "Lots of dogs and friendly people around. Dogs are always on leash and people pick up after their dogs."
    0
    Flag
  • Jgmeerdter
    "It’s a nice and quiet area. Very safe and friendly. It’s tucked away and located in a close proximity to a bigger city."
    0
    Flag
  • Margaret C.
    "No public transportation. Bedroom community. Rural. Town was founded in the 1790’s. There are a few family-owned restaurants and a 7-Eleven w/ gas station."
    0
    Flag
  • Aokigahara169
    "New windsor has a great heritage and a quiet feel. Miss it everyday. Really hope to move back soon. "
    0
    Flag
  • Harriet725
    "You see plenty of dogs in this neighborhood. There is plenty of space for walking dogs. Most people are dog friendly."
    1
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 404 High St

  • What is 404 High St estimated to be worth?
    Trulia's estimated value for 404 High St in New Windsor, MD is $515,400.
  • What is the price history for 404 High St?
    404 High St in New Windsor, MD last sold for $399,900 in August 2008.
  • Is New Windsor a buyer's or seller's market?
    New Windsor is currently a seller's market, based on recent for-sale activity.
  • What do residents say about New Windsor?
    Residents describe New Windsor, MD as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in New Windsor, MD.
  • How big is the lot at 404 High St?
    The lot at 404 High St in New Windsor, MD is about 0.43 acres (18,719 sq ft).
  • Does 404 High St have a garage?
    Yes, 404 High St in New Windsor, MD has a garage.

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