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 307 Hillside Dr estimated to be worth?

Trulia's estimated value for 307 Hillside Dr in New Windsor, MD is $303,700 .

What is the price history for 307 Hillside Dr?

307 Hillside Dr in New Windsor, MD last sold for $135,000 in January 2004.

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 307 Hillside Dr?

The lot at 307 Hillside Dr in New Windsor, MD is about 0.35 acres (15,336 sq ft).

Does 307 Hillside Dr have a garage?

Yes, 307 Hillside Dr in New Windsor, MD has a garage.

OFF MARKET

$303,700

Trulia Estimate

Studio
1 Bath
1,394 sqft (on 0.35 acres)

307 Hillside Dr, New Windsor, MD 21776

Refinance Your Home

Currently Off Market - Sold Jan 30, 2004 for $135,000

Home Value

Trulia Estimate

$304K

Since last month

$4K (+1.2%)

Since last year

$24K (+8.6%)

Since last sale

$170K (+125.6%)

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 +55% in the last 10 years

Month	Estimated value
2026
August 2026	$305K
August 2026	$304K
July 2026	$301K
June 2026	$309K
May 2026	$299K
April 2026	$291K
March 2026	$292K
February 2026	$280K
January 2026	$276K
2025
December 2025	$277K
November 2025	$284K
October 2025	$280K
September 2025	$285K
August 2025	$280K
July 2025	$299K
June 2025	$301K
May 2025	$300K
April 2025	$304K
March 2025	$288K
February 2025	$278K
January 2025	$277K
2024
December 2024	$282K
November 2024	$287K
October 2024	$296K
September 2024	$293K
August 2024	$298K
July 2024	$297K
June 2024	$297K
May 2024	$296K
April 2024	$289K
March 2024	$287K
February 2024	$282K
January 2024	$277K
2023
December 2023	$276K
November 2023	$276K
October 2023	$277K
September 2023	$279K
August 2023	$281K
July 2023	$286K
June 2023	$291K
May 2023	$252K
April 2023	$245K
March 2023	$238K
February 2023	$218K
January 2023	$209K
2022
December 2022	$217K
November 2022	$220K
October 2022	$223K
September 2022	$225K
August 2022	$228K
July 2022	$237K
June 2022	$238K
May 2022	$234K
April 2022	$229K
March 2022	$229K
February 2022	$230K
January 2022	$243K
2021
December 2021	$232K
November 2021	$237K
October 2021	$238K
September 2021	$240K
August 2021	$244K
July 2021	$252K
June 2021	$267K
May 2021	$296K
April 2021	$289K
March 2021	$271K
February 2021	$261K
January 2021	$254K
2020
December 2020	$256K
November 2020	$249K
October 2020	$246K
September 2020	$241K
August 2020	$249K
July 2020	$243K
June 2020	$244K
May 2020	$245K
April 2020	$242K
March 2020	$240K
February 2020	$242K
January 2020	$242K
2019
December 2019	$244K
November 2019	$241K
October 2019	$239K
September 2019	$242K
August 2019	$245K
July 2019	$240K
June 2019	$238K
May 2019	$228K
April 2019	$215K
March 2019	$208K
February 2019	$219K
January 2019	$221K
2018
December 2018	$218K
November 2018	$222K
October 2018	$230K
September 2018	$231K
August 2018	$229K
July 2018	$226K
June 2018	$228K
May 2018	$224K
April 2018	$231K
March 2018	$235K
February 2018	$237K
January 2018	$236K
2017
December 2017	$233K
November 2017	$221K
October 2017	$221K
September 2017	$223K
August 2017	$217K
July 2017	$204K
June 2017	$210K
May 2017	$213K
April 2017	$204K
March 2017	$203K
February 2017	$208K
January 2017	$200K
2016
December 2016	$187K
November 2016	$192K
October 2016	$197K
September 2016	$196K

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
418 Church St, New Windsor, MD	0.07	Single-Family Home	$205,000	12/16/25	2	1	1,416
1324 Old New Windsor Rd, New Windsor, MD	0.64	Single-Family Home	$125,000	01/09/26		1	1,296
3180 Vista Ct, New Windsor, MD	0.63	Single-Family Home	$272,500	06/25/26		1	1,188
2824 Graybill Ct, New Windsor, MD	0.35	Single-Family Home	$405,000	11/21/25	3	2	1,260
315 College Ave, New Windsor, MD	0.19	Single-Family Home	$390,000	09/11/26	3	2	2,291
1038 Green Valley Rd, New Windsor, MD	0.35	Single-Family Home	$375,000	04/30/26	3	1.5	936
115 Main St, New Windsor, MD	0.38	Single-Family Home	$150,000	02/24/26		2	1,664
306 College Ave, New Windsor, MD	0.25	Single-Family Home	$395,000	12/19/25	3	2	2,258
227 Main St, Westminster, MD	0.23	Single-Family Home	$325,000	06/12/26		2	1,800
227-229 Main St, New Windsor, MD	0.23	Single-Family Home	$325,000	05/15/26	3	2	1,800

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
401 Church St, New Windsor, MD 21776	0.09	$357,000	3	2	1,302	Off Market
418 Church St, New Windsor, MD 21776	0.07	$205,000	2	1	1,416	Recently Sold
420 Church St, New Windsor, MD 21776	0.07	$399,200	4	1.5	1,845	Off Market
419 Main St, New Windsor, MD 21776	0.10	$449,000	4	2	2,640	Off Market
296 Lambert Ave, New Windsor, MD 21776	0.17	$450,800	3	3	2,357	Off Market
211 Church St, New Windsor, MD 21776	0.19	$416,200	5	3	3,063	Off Market
2788 Town View Cir, New Windsor, MD 21776	0.18	$625,000	5	3.5	2,770	Recently Sold
307 Main St, New Windsor, MD 21776	0.19	$269,400	3	1	1,236	Off Market
101 Blue Ridge Ave, New Windsor, MD 21776	0.18	$458,700	4	2.5	3,231	Off Market
2728 Town View Cir, New Windsor, MD 21776	0.17	$649,900	4	2.5	2,794	For Sale
315 College Ave, New Windsor, MD 21776	0.19	$390,000	3	2	2,291	Recently Sold
2793 Town View Cir, New Windsor, MD 21776	0.20	$435,400	3	2.5	2,320	Off Market

Local Information

Map ViewExplore the area around 307 Hillside Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Single-Family Home

Built in 1949

0.35 acre lot

1,394 sqft

$218/sqft

Garage

About this House

This single-family home is located at 307 Hillside Dr, New Windsor, MD. 307 Hillside Dr is in New Windsor, MD and in ZIP code 21776. This property has 1 bathroom and approximately 1,394 sqft of floor space. This property has a lot size of 0.35 acres and was built in 1949.

307 Hillside Dr, New Windsor, MD 21776 is a studio, 1 bathroom, 1,394 sqft single-family home built in 1949. It last sold for $135,000 on Jan 30, 2004. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $303,700, with a rent estimate of $1,962/month.

Home Details for 307 Hillside Dr

Interior Features
Interior Details Basement
Heating & Cooling Heating: RadiantAir ConditioningHeating Fuel: Radiant
Levels, Entrance, & Accessibility Stories: 1.5

Exterior Features
Exterior Home Features Roof: MetalExterior: Other
Parking & Garage GarageParking: Garage Attached

Property Information
Year Built Year Built: 1949
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional

Community
Units in Building: 1

Lot Information
Lot Area: 0.35 acres

Price and Tax history

Date	Event	Price
Jan 30, 2004 Source: N/A	Sold	$135,000

Year	Property tax	Tax assessment
2025	$3,091	$222,100

Additional Cost

Market trends in New Windsor

Last updated August 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

1MoM

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
Flag
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
Flag
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
Flag
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
Flag
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
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 307 Hillside Dr

What is 307 Hillside Dr estimated to be worth?
Trulia's estimated value for 307 Hillside Dr in New Windsor, MD is $303,700.
What is the price history for 307 Hillside Dr?
307 Hillside Dr in New Windsor, MD last sold for $135,000 in January 2004.
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 307 Hillside Dr?
The lot at 307 Hillside Dr in New Windsor, MD is about 0.35 acres (15,336 sq ft).
Does 307 Hillside Dr have a garage?
Yes, 307 Hillside Dr in New Windsor, MD has a garage.