#MDAA2119980, Elizabeth C Dooner, Listing office: Coldwell Banker Realty
399 Hilltop Ln Annapolis, MD 21403
Property details
About 399 Hilltop Ln
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. Main Home (3BR/2BA): Beautiful hardwood floors flows 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. 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.
Highlights
(ACTIVE)
Summary
- Full Bathrooms: 4
- Basement: Yes
- Total Bedroom Count: 4
- Garage Space: 1 space
- Parking: Other, Detached Garage,Off Street,Driveway
- Architectural Style: Split Level
- Heating: Forced Air
- Cooling: Ceiling Fan(s), Central Air, Heat Pump
- List Price: $650,000
- Price/SqFt: $177
- Annual Tax Amount: $4,475
- Tax Year: 2024
- Directions: Hilltop Lane to 399 Hilltop corner of Hilltop and Primrose. You can park in the driveway on Hilltop or Driveway in back of house off Primrose.
- Year Built: 1966
- Living Area: 3,668 SqFt
- Municipality: Annapolis
- Lot Size: 0.26 Acres
- MLS Number: MDAA2118498
- MLS Name: BRIGHT
- Office Name: Coldwell Banker Realty
- Office Phone: (410) 224-2200
- Office Email: cedric.lewis@cbmove.com
- Listing Agent: James J Ellis
- Agent Phone: (410) 320-7718
- Agent Email: jellis@cbmove.com
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Price information
Property sales
We're sorry, we currently don't have property sales data for this listing.
Tax history
Year | Assessment | Property Tax |
---|---|---|
2024 | $406,100 | $4,475 |
2023 | $375,200 | $4,475 |
2022 | $365,167 | $5,145 |
2021 | $355,133 | $4,309 |
2020 | $345,100 | $4,091 |
2018 | $309,833 | $3,709 |
2017 | $292,200 | $3,283 |
History based on county public records data.
Nearby schools
3
Tyler Heights Elementary School
Public District PK-5
0.4 mi
•200 Janwall St
3
Georgetown East Elementary School
Public District PK-5
0.8 mi
•111 Dogwood Rd
3
Eastport Elementary School
Public District PK-5
1.0 mi
•420 Fifth St
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $64,440. The majority of Annapolis, MD residents have income between $35k-100k annually. The majority of families are single, no kids. Residents of this area typically have high school diploma education.
Similar homes for sale
Frequently asked questions
Living in Annapolis, MD
Transportation in Annapolis includes a variety of options for residents and visitors. The city's public transit system provides connections to key areas, and the presence of ride-sharing services offers additional flexibility. Annapolis is known for its walkable downtown, while other areas are more car-dependent. Major roads and highways facilitate travel in and out of the city, and ongoing infrastructure projects aim to improve traffic flow and accessibility.
The community benefits from a robust educational system, with a number of public and private schools serving the area, as well as higher education institutions like St. John's College. Annapolis is equipped with several healthcare facilities, offering a range of services from routine care to specialized medical treatments. The city also hosts a public library system that serves as a resource for residents. Retail and dining options are plentiful, with establishments ranging from boutique shops to nationally recognized chains, many of which reflect the local seafood cuisine.
Annapolis is celebrated for its historic charm and maritime heritage. The city prides itself on being the state capital and the home of the United States Naval Academy. Community events such as the Annapolis Boat Shows and the Maryland Seafood Festival showcase the city's connection to the Chesapeake Bay. The area's character is further defined by its walkable downtown area, which features a blend of antique shops, art galleries, and waterfront dining.
Annapolis offers a diverse array of housing options, with single-family homes being a significant part of the market. Architectural styles range from colonial to contemporary, reflecting the city's rich history and modern growth. The housing market is dynamic, with a mix of historic homes and newer developments. While the majority of residents own their homes, a substantial portion of the population opts for rental properties, including apartments and townhouses.
About 399 Hilltop Ln
The listing price of 399 Hilltop Ln property is $650,000.
The property 399 Hilltop Ln is a house located in Annapolis, Maryland, 21403.
Active Listing: 399 Hilltop Ln is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 399 Hilltop Ln are: Tyler Heights Elementary School (GreatSchools Rating 3/10), Georgetown East Elementary School (GreatSchools Rating 3/10), Eastport Elementary School (GreatSchools Rating 3/10), Annapolis Middle School (GreatSchools Rating 2/10), Wiley H. Bates Middle School (GreatSchools Rating 5/10), Central Middle School (GreatSchools Rating 8/10), Annapolis High School (GreatSchools Rating 3/10), South River High School (GreatSchools Rating 9/10), Broadneck High School (GreatSchools Rating 8/10).
According to the records, the last property tax for 2024 is $4,475 (source: MLS/based on county public records data).
The property at 399 Hilltop Ln has 4 bedrooms and 4 bathrooms.
The property 399 Hilltop Ln is 3,668 SqFt (source: MLS/tax record).
The year of construction for 399 Hilltop Ln is 1966.
This home is located at 399 Hilltop Ln in Annapolis, MD and zip code 21403. This 3,668 square foot home, which was built in 1966, sits on a 0.26 acre lot. Features: 4 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since June 17, 2025 and is currently priced at $650,000.
In June 2025 in Annapolis, MD there were 63.5% more homes for sale than in May. While the average time on the market in June 2025 was 64 days, the median list price was $699,900.