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399 Hilltop Ln, 
Annapolis, MD 21403

$595,000


4

Beds


4

Baths


3,668

Sq Ft


Single Family

Active

Listed by

Jimmy Ellis

Last updated:

October 5, 2025, 01:38 PM

MLS#

MDAA2118498

Source:

BRIGHTMLS

Company Logo

About This Home

399 Hilltop Ln

Huge Price adjustment!!!!! Discover your slice of paradise in the heart of Annapolis! This exceptional property combines two complete homes with productive fruit trees, creating the ultimate in flexible living. It is Opened up to be one home but with little work you can close off to make this two separate living areas. Main Home (3BR/2BA): Beautiful hardwood floors flow through the large living room and bedrooms, while the spacious kitchen with Island connects to a separate dining area - perfect fro daily living and entertaining. Three comfortable bedrooms and two full baths complete this well designed space. You can close off addition very easily and make it a true In-Law suite or a nice rental apartment for extra income. In-Law suite Addition (1BR/2BA - 1200 sq ft): This isn't just and addition - It's a complete second home! Features include a large living room, Full eat-in kitchen, bedroom, two full baths, and generous laundry room. The crown jewel? An incredible 8x28 Sunroom with natural gas fireplace - your year round sanctuary with garden views. Separate entrance ensures complete privacy. Step outside to your personal orchard featuring mature pear, apple, cherry, plum and chestnut trees, plus established grapevines. Imagine morning coffee in the sunroom or out the back patio surrounded by blooming fruit trees and harvesting your own fresh produce each season. Entertaining made effortless with a sprawling 650 sq ft deck - perfect for everything from intimate dinners to large gatherings. The outdoor space flows seamlessly with nature's bounty at your fingertips. Two separate driveways ensure privacy and convenience, with circular drive serving the main house (multiple car capacity) and a dedicated 4 - car driveway for the In-law suite. Storage and workspace solved with a generous 12x24 detached garage and 8x14 shed - plenty of room for vehicles, tools, hobbies and seasonal storage. Prime Annapolis location puts you in the heart of Maryland's historic capital where waterfront charm continues to fuel demand and properties remain strong. Just a mile from downtown Annapolis for all your dining and shopping needs. Walk to Truxtun park and the Pip Moyer center that houses a gym, basketball courts, and an indoor track. You can also walk to the newly renovated tennis court and Pickleball courts with lights. Around the corner is the Truxtun park pool, Public Boat ramp and fishing pier.

Home Facts

Single Family

4 Baths

4 Bedrooms

Built in 1966

Price Summary

595,000

$162 per Sq. Ft.

MLS #:

MDAA2118498

Last Updated:

October 5, 2025, 01:38 PM

Added:

3 month(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

4

Bathrooms

Total Bathrooms:

4

Full Bathrooms:

4

Interior

Living Area:

3,668 Sq. Ft.


Structure

Structure

Architectural Style:

Split Level

Building Area:

3,668 Sq. Ft.

Year Built:

1966


Lot

Lot Size (Sq. Ft):

11,325


Finances & Disclosures

Finances

Price:

$595,000

Price per Sq. Ft:

$162 per Sq. Ft.

399 Hilltop Ln
Source:BRIGHTMLS
The information being provided by Bright MLS is for the consumer’s personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information is deemed reliable but not guaranteed and should therefore be independently verified. © 2025 Bright MLS All rights reserved.

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