399 Hilltop Ln, Annapolis, MD 21403
Local realty services provided by:Better Homes and Gardens Real Estate Reserve
399 Hilltop Ln,Annapolis, MD 21403
$595,000
- 4 Beds
- 4 Baths
- 3,668 sq. ft.
- Single family
- Active
Listed by:james j ellis
Office:coldwell banker realty
MLS#:MDAA2118498
Source:BRIGHTMLS
Price summary
- Price:$595,000
- Price per sq. ft.:$162.21
About this home
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.
Contact an agent
Home facts
- Year built:1966
- Listing ID #:MDAA2118498
- Added:104 day(s) ago
- Updated:September 30, 2025 at 01:47 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:4
- Full bathrooms:4
- Living area:3,668 sq. ft.
Heating and cooling
- Cooling:Ceiling Fan(s), Central A/C, Heat Pump(s)
- Heating:90% Forced Air, Natural Gas
Structure and exterior
- Roof:Asphalt
- Year built:1966
- Building area:3,668 sq. ft.
- Lot area:0.26 Acres
Schools
- High school:ANNAPOLIS
- Middle school:ANNAPOLIS
- Elementary school:TYLER HEIGHTS
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$595,000
- Price per sq. ft.:$162.21
- Tax amount:$5,836 (2024)
New listings near 399 Hilltop Ln
- Coming Soon
$445,000Coming Soon2 beds 2 baths944 Yachtsman Way, ANNAPOLIS, MD 21403
MLS# MDAA2127418Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - Coming Soon
$699,000Coming Soon4 beds 3 baths228 Dubois Rd, ANNAPOLIS, MD 21401
MLS# MDAA2127442Listed by: LONG & FOSTER REAL ESTATE, INC. - New
$415,000Active2 beds 2 baths1,272 sq. ft.940 Astern Way #604, ANNAPOLIS, MD 21401
MLS# MDAA2127410Listed by: SYNERGY REALTY - New
$1,649,000Active3 beds 3 baths2,876 sq. ft.214 Wardour Dr, ANNAPOLIS, MD 21401
MLS# MDAA2127246Listed by: COLDWELL BANKER REALTY - Coming SoonOpen Sat, 11am to 1pm
$624,900Coming Soon3 beds 2 baths101 Lake View Dr, ANNAPOLIS, MD 21403
MLS# MDAA2127260Listed by: NEXT STEP REALTY, LLC. - New
$1,050,000Active0.34 Acres10 Annapolis St, ANNAPOLIS, MD 21401
MLS# MDAA2127370Listed by: COLDWELL BANKER REALTY - Coming Soon
$699,000Coming Soon4 beds 2 baths742 Warren Dr, ANNAPOLIS, MD 21403
MLS# MDAA2127324Listed by: COLDWELL BANKER REALTY - Coming Soon
$675,000Coming Soon2 beds 3 baths1915 Towne Centre Blvd #306, ANNAPOLIS, MD 21401
MLS# MDAA2127358Listed by: LONG & FOSTER REAL ESTATE, INC. 
$675,070Pending2 beds 2 baths1,621 sq. ft.76 Old Mill Bottom Rd N #312, ANNAPOLIS, MD 21409
MLS# MDAA2127252Listed by: MCWILLIAMS/BALLARD, INC.
$435,000Pending1 beds 2 baths1,002 sq. ft.5 Spa Creek Lndg #a2, ANNAPOLIS, MD 21403
MLS# MDAA2124136Listed by: COLDWELL BANKER REALTY
Protect your home and budget with an American Home Shield© home warranty. Learn more© 2025 Better Homes and Gardens Real Estate LLC. An Anywhere Real Estate company. All rights reserved. Better Homes and Gardens® Real Estate is a registered trademark owned by Meredith Operations Corporation, licensed to Better Homes and Gardens Real Estate LLC and used with permission. Better Homes and Gardens Real Estate LLC fully supports the principles of the Fair Housing Act and the Equal Opportunity Act. Listing information is deemed reliable but is not guaranteed accurate.
Each office is independently owned and operated.
Any services or products provided by third parties are not provided by, affiliated with or related to Better Homes and Gardens Real Estate LLC, or its affiliated companies.