306 Hillside Dr, New Windsor, MD 21776
OFF MARKET

306 Hillside Dr
New Windsor, MD 21776

  • 2 Beds
  • 1 Bath
  • 907 sqft (on 0.29 acres)

$291,800

Trulia Estimate
as of Jun 29, 2026

$291,800

Trulia Estimate
as of Jun 29, 2026
2 Beds
1 Bath
907 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 306 Hillside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 306 Hillside Dr, New Windsor, MD. 306 Hillside Dr is in New Windsor, MD and in ZIP code 21776. This property has 2 bedrooms, 1 bathroom and approximately 907 sqft of floor space. This property has a lot size of 0.29 acres and was built in 1958.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 306 Hillside Dr

Interior Features

Interior Details
BasementAtticTypes of Rooms: Dining Room, Family RoomCeiling Fan
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1Floors: Hardwood
Appliances & Utilities
Cable ReadyDryerMicrowaveRefrigeratorWasher

Exterior Features

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

Property Information

Year Built
Year Built: 1958
Property Type / Style
Property Type: Single Family HomeArchitecture: Conventional

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price History for 306 Hillside Dr

DatePriceEventSource
07/29/2019$192,000Sold
N/A
05/31/2019$185,000PendingAgent Provided
05/24/2019$185,000Listed For SaleAgent Provided
10/09/2001$92,000Sold
N/A
08/05/1999$85,000Sold
N/A

Market trends in New Windsor

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
20
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Property Tax and Assessment

Year2025
Tax$2,798
Assessment$201,067
Home facts updated by county records

Comparable Sales for 306 Hillside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.08
Single-Family Home
$205,000
12/16/25
2
1
1,416
0.31
Single-Family Home
$405,000
11/21/25
3
2
1,260
0.38
Single-Family Home
$375,000
04/30/26
3
1.5
936
0.23
Single-Family Home
$137,000
07/23/25
1
1,344
0.55
Single-Family Home
$405,000
08/15/25
3
1
1,384
0.28
Single-Family Home
$395,000
12/19/25
3
2
2,258
0.68
Single-Family Home
$252,000
12/09/25
2
2
1,772
0.27
Single-Family Home
$325,000
05/15/26
3
2
1,800
0.32
Single-Family Home
$351,000
08/29/25
3
1.5
1,733
0.22
Single-Family Home
$440,000
09/08/25
3
3
2,357

Nearby homes

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Assigned Schools

These are the assigned schools for 306 Hillside Dr.
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 16 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 there's holiday spirit

  • 71 % Say kids play outside

  • 70 % Say streets are well-lit

  • 70 % Say people would walk alone at night

  • 59 % Say there's wildlife

  • 58 % Say neighbors are friendly

  • 44 % Say it's walkable to restaurants

  • 38 % 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 "
  • Jgmeerdter
    "Lots of dogs and friendly people around. Dogs are always on leash and people pick up after their dogs."
  • 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."
  • 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."
  • Aokigahara169
    "New windsor has a great heritage and a quiet feel. Miss it everyday. Really hope to move back soon. "
  • Harriet725
    "You see plenty of dogs in this neighborhood. There is plenty of space for walking dogs. Most people are dog friendly."

LGBTQ Local Legal Protections

Apartments for Rent

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Homes for sale near 306 Hillside Dr

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Off Market Homes Near 306 Hillside Dr

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306 Hillside Dr, New Windsor, MD 21776 is a 2 bedroom, 1 bathroom, 907 sqft single-family home built in 1958. This property is not currently available for sale. 306 Hillside Dr was last sold on Jul 29, 2019 for $192,000. The current Trulia Estimate for 306 Hillside Dr is $291,800.