Are yards well-kept in New Windsor, MD?

As of early 2026, 100% of users say yards are well-kept

Is New Windsor, MD dog-friendly?

As of early 2026, 95% of users say it's dog friendly

Is a car needed in New Windsor, MD?

As of early 2026, 95% of users say car is needed

Is parking easy in New Windsor, MD?

As of early 2026, 86% of users say parking is easy

Does New Windsor, MD have sidewalks?

As of early 2026, 79% of users say there are sidewalks

Is New Windsor, MD quiet?

As of early 2026, 73% of users say it's quiet

Would people walk alone at night in New Windsor, MD?

As of early 2026, 71% of users say people would walk alone at night

Does New Windsor, MD show holiday spirit?

As of early 2026, 71% of users say there's holiday spirit

Do kids play outside in New Windsor, MD?

As of early 2026, 71% of users say kids play outside

Are the streets well-lit in New Windsor, MD?

As of early 2026, 70% of users say streets are well-lit

Is there wildlife in New Windsor, MD?

As of early 2026, 59% of users say there's wildlife

Are neighbors friendly in New Windsor, MD?

As of early 2026, 58% of users say neighbors are friendly

Is New Windsor, MD walkable to restaurants?

As of early 2026, 44% of users say it's walkable to restaurants

Do residents of New Windsor, MD plan to stay at least 5 years?

As of early 2026, 41% of users say they plan to stay for at least 5 years

Are there community events in New Windsor, MD?

As of early 2026, 26% of users say there are community events

What is 417 Main St estimated to be worth?

Trulia's estimated value for 417 Main St in New Windsor, MD is $418,400 .

What is the price history for 417 Main St?

417 Main St in New Windsor, MD last sold for $220,000 in September 2016.

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 417 Main St?

The lot at 417 Main St in New Windsor, MD is about 0.39 acres (16,988 sq ft).

OFF MARKET

$418,400

Trulia Estimate

5 Beds
2 Baths
3,361 sqft (on 0.39 acres)

417 Main St, New Windsor, MD 21776

Refinance Your Home

Currently Off Market - Sold Sep 12, 2016 for $220,000

Home Value

Trulia Estimate

$418K

Since last month

$600 (+0.1%)

Since last year

$40K (+10.5%)

Since last sale

$198K (+90.2%)

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 +90% in the last 10 years

Month	Estimated value
2026
August 2026	$418K
August 2026	$418K
July 2026	$418K
June 2026	$430K
May 2026	$409K
April 2026	$399K
March 2026	$400K
February 2026	$380K
January 2026	$373K
2025
December 2025	$372K
November 2025	$379K
October 2025	$382K
September 2025	$390K
August 2025	$379K
July 2025	$406K
June 2025	$411K
May 2025	$416K
April 2025	$415K
March 2025	$399K
February 2025	$390K
January 2025	$387K
2024
December 2024	$392K
November 2024	$403K
October 2024	$411K
September 2024	$406K
August 2024	$418K
July 2024	$419K
June 2024	$420K
May 2024	$418K
April 2024	$406K
March 2024	$407K
February 2024	$399K
January 2024	$391K
2023
December 2023	$388K
November 2023	$384K
October 2023	$388K
September 2023	$397K
August 2023	$395K
July 2023	$415K
June 2023	$419K
May 2023	$388K
April 2023	$383K
March 2023	$377K
February 2023	$368K
January 2023	$367K
2022
December 2022	$371K
November 2022	$377K
October 2022	$383K
September 2022	$388K
August 2022	$392K
July 2022	$406K
June 2022	$413K
May 2022	$407K
April 2022	$399K
March 2022	$400K
February 2022	$400K
January 2022	$397K
2021
December 2021	$393K
November 2021	$391K
October 2021	$389K
September 2021	$391K
August 2021	$395K
July 2021	$390K
June 2021	$358K
May 2021	$294K
April 2021	$270K
March 2021	$269K
February 2021	$284K
January 2021	$298K
2020
December 2020	$302K
November 2020	$314K
October 2020	$307K
September 2020	$297K
August 2020	$304K
July 2020	$302K
June 2020	$291K
May 2020	$276K
April 2020	$274K
March 2020	$264K
February 2020	$246K
January 2020	$249K
2019
December 2019	$255K
November 2019	$347K
October 2019	$283K
September 2019	$256K
August 2019	$239K
July 2019	$239K
June 2019	$240K
May 2019	$240K
April 2019	$241K
March 2019	$239K
February 2019	$237K
January 2019	$239K
2018
December 2018	$237K
November 2018	$238K
October 2018	$235K
September 2018	$237K
August 2018	$236K
July 2018	$234K
June 2018	$236K
May 2018	$236K
April 2018	$237K
March 2018	$238K
February 2018	$233K
January 2018	$235K
2017
December 2017	$235K
November 2017	$232K
October 2017	$231K
September 2017	$229K
August 2017	$225K
July 2017	$227K
June 2017	$226K
May 2017	$224K
April 2017	$223K
March 2017	$224K
February 2017	$224K
January 2017	$222K
2016
December 2016	$222K
November 2016	$220K
October 2016	$220K
September 2016	$220K

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
306 College Ave, New Windsor, MD	0.18	Single-Family Home	$395,000	12/19/25	3	2	2,258
2832 Graybill Ct, New Windsor, MD	0.28	Single-Family Home	$590,000	04/30/26	4	2.5	2,548
205 Church St, New Windsor, MD	0.23	Single-Family Home	$730,000	10/29/25	4	3	4,386
418 Church St, New Windsor, MD	0.03	Single-Family Home	$205,000	12/16/25	2	1	1,416
414 High St, New Windsor, MD	0.31	Single-Family Home	$464,000	06/15/26	3	2.5	2,668
1038 Green Valley Rd, New Windsor, MD	0.27	Single-Family Home	$375,000	04/30/26	3	1.5	936
2802 Town View Cir, New Windsor, MD	0.34	Single-Family Home	$599,900	11/19/25	6	3	2,604
107 S Springdale Ave, New Windsor, MD	0.24	Single-Family Home	$474,900	03/13/26	3	3	2,232
2823 Graybill Ct, New Windsor, MD	0.36	Single-Family Home	$550,000	03/05/26	4	3	3,037
2824 Graybill Ct, New Windsor, MD	0.34	Single-Family Home	$405,000	11/21/25	3	2	1,260

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
419 Main St, New Windsor, MD 21776	0.01	$449,000	4	2	2,640	Off Market
101 Blue Ridge Ave, New Windsor, MD 21776	0.08	$458,700	4	2.5	3,231	Off Market
418 Church St, New Windsor, MD 21776	0.03	$205,000	2	1	1,416	Recently Sold
420 Church St, New Windsor, MD 21776	0.04	$399,200	4	1.5	1,845	Off Market
310 College Ave, New Windsor, MD 21776	0.15	$419,400	4	2	1,950	Off Market
401 Church St, New Windsor, MD 21776	0.11	$357,000	3	2	1,302	Off Market
307 Main St, New Windsor, MD 21776	0.15	$269,400	3	1	1,236	Off Market
306 College Ave, New Windsor, MD 21776	0.18	$395,000	3	2	2,258	Recently Sold
302 College Ave, New Windsor, MD 21776	0.20	$486,700	5	3.5	3,430	Off Market
227-229 Main St, New Windsor, MD 21776	0.20	$325,000	3	2	1,800	Recently Sold
211 Church St, New Windsor, MD 21776	0.19	$416,200	5	3	3,063	Off Market
221 Main St, New Windsor, MD 21776	0.22	$309,000	4	1.5	1,936	For Sale

Local Information

Map ViewExplore the area around 417 Main St.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1920

0.39 acre lot

3,361 sqft

$124/sqft

About this House

VERY CHARMING VICTORIAN LOCATED AMONGST MANY STATELY HOMES IN OLD TOWN NEW WINDSOR. THIS HOME HAS SO MUCH TO OFFER WITH 10 FOOT CEILINGS, POCKET DOORS,CUSTOM MOLDING THROUGHOUT,INLAY FLOORS, SO MANY POSSIBILITIES.PERFECT FOR IN LAW OR HOME OFFICE ARRANGEMENT CURRENTLY HOME HAS COMPLETE KITCHENS AND BATHS ON BOTH LEVELS. WELCOME HOME! GOOD BONES IN NEED OF UPDATES.CARRIAGE HOUSE ROOM TO TINKER.

417 Main St, New Windsor, MD 21776 is a 5 bedroom, 2 bathroom, 3,361 sqft single-family home built in 1920. It last sold for $220,000 on Sep 12, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $418,400, with a rent estimate of $2,674/month.

Home Details for 417 Main St

Interior Features
Interior Details BasementTypes of Rooms: Breakfast NookCeiling Fan
Heating & Cooling Heating: BaseboardHeating Fuel: Baseboard
Levels, Entrance, & Accessibility Stories: 3
Appliances & Utilities DishwasherRefrigerator
Fireplace & Spa Fireplace

Exterior Features
Exterior Home Features Roof: SlateExterior: Vinyl

Property Information
Year Built Year Built: 1920
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.39 acres

Price and Tax history

Date	Event	Price
Sep 12, 2016 Source: N/A	Sold	$220,000
Jun 6, 2016 Source: Agent Provided	PriceChange	$225,000 Price decreased by 18%
Apr 5, 2016 Source: Agent Provided	PriceChange	$275,000 Price decreased by 8%
Nov 1, 2015 Source: Agent Provided	PriceChange	$299,900 Price decreased by 6%
Aug 4, 2015 Source: Agent Provided	PriceChange	$319,000 Price decreased by 6%
Jun 15, 2015 Source: Agent Provided	Listed For Sale	$339,000

Year	Property tax	Tax assessment
2025	$4,199	$304,000

Additional Cost

Market trends in New Windsor

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

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Available listings

Around this home

Elmer A. Wolfe Elementary School
PK-5
Public
505 Students
Carroll County Public Schools
6/10
GreatSchools Rating
Parent Rating Average
Let's say as a parent I'm just not too happy with the school
Parent Review
8y ago
4 Reviews

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 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.
Prev. Resident
1y ago
"New Windsor is a wonderful small town however the water prices are ridiculous and drives many people away "
0
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Jgmeerdter
Resident
2y ago
"Lots of dogs and friendly people around. Dogs are always on leash and people pick up after their dogs."
0
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Jgmeerdter
Resident
2y ago
"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
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Margaret C.
Resident
5y ago
"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
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Aokigahara169
Prev. Resident
7y ago
"New windsor has a great heritage and a quiet feel. Miss it everyday. Really hope to move back soon. "
0
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Harriet725
Resident
7y ago
"You see plenty of dogs in this neighborhood. There is plenty of space for walking dogs. Most people are dog friendly."
1
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LGBTQ Local Legal Protections

Frequently asked questions about 417 Main St

What is 417 Main St estimated to be worth?
Trulia's estimated value for 417 Main St in New Windsor, MD is $418,400.
What is the price history for 417 Main St?
417 Main St in New Windsor, MD last sold for $220,000 in September 2016.
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 417 Main St?
The lot at 417 Main St in New Windsor, MD is about 0.39 acres (16,988 sq ft).