#MDAA2119300, Robert J Chew, Listing office: Samson Properties
357 Overlook Trl Annapolis, MD 21401
Property details
About 357 Overlook Trl
Enchanting Craftsman-Style Waterfront Retreat in Epping Forest Tucked away in the prestigious gated community of Epping Forest, this beautifully renovated Craftsman-style home offers a rare opportunity to enjoy serene waterfront living with a private deep-water pier on Clements Creek, just off the Severn River. Complete with a 12,000 lb boat lift and a private sandy beach, it’s a dream for boating enthusiasts and nature lovers alike. From this peaceful sanctuary, you’ll have direct access to all of Annapolis’s waterways—and beyond. Expertly sited on a perfectly elevated 0.39-acre lot, this 4-bedroom, 4-bath home spans over 3,000 square feet across three levels, offering treetop views, tranquil wooded surroundings, and captivating water glimpses. A graceful stone stairway with cable railing leads to the entrance, where lush landscaping and the sounds of nature welcome you. Inside, the open floor plan and abundant natural light highlight the home’s craftsmanship and thoughtful design. The kitchen, dining area, and living room with fireplace seamlessly connect to a screened-in porch and a spacious deck—ideal for al fresco dining and enjoying the tranquil surroundings. The main level includes a bedroom and full bath, perfect for one-level living. Upstairs, a spacious landing with soaring ceilings leads to two ensuite bedrooms, including the luxurious primary suite with a private balcony, treetop vistas, and a spa-like bath featuring dual vanities and a walk-in tiled shower. The versatile lower level offers a cozy family room with fireplace, an additional bedroom and full bath, a home office or bonus room, generous storage, and a private patio—perfect for guests or multi-generational living. Residents of Epping Forest enjoy an unparalleled lifestyle with access to a waterfront clubhouse and bar, deep-water marina, sandy beach, boat ramp, tennis courts, hiking trails, and a full calendar of community events including fireworks, oyster roasts, holiday festivals, and summer camps. Active social groups like the boat club, volleyball leagues, swim team, and garden club offer something for everyone. Annapolis, known as the "Sailing Capital of America," boasts one of the longest and most vibrant boating seasons on the East Coast—extending well into the fall, when the waterways are framed by dynamic foliage and crisp, golden light. Conveniently located just minutes from Downtown Annapolis, the Bay Bridge, and major routes to Washington, D.C., this home is the perfect blend of relaxation, recreation, and accessibility.
Highlights
(COMING SOON)
Summary
- Full Bathrooms: 4
- Basement: Yes
- Interior: Attic, Breakfast Area, Built-Ins, Ceiling Fan(s), Combination Dining/Living, Combination Kitchen/Dining, Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Kitchen - Gourmet, Kitchen - Island, Pantry, Primary Bath(s), Recessed Lighting, Stain/Lead Glass, Upgraded Countertops, Walk-in Closet(s), Wood Floors
- Fireplace: Brick, Gas/Propane, Fireplace - Glass Doors, Insert, Mantel(s)
- Total Bedroom Count: 4
- Parking: Parking Lot
- Exterior: Extensive Hardscape, Exterior Lighting
- Architectural Style: Craftsman
- Heating: Heat Pump, Other
- Cooling: Central Air, Ceiling Fan(s)
- List Price: $1,398,000
- Price/SqFt: $455
- HOA Amount: $0 Other
- Annual Tax Amount: $3,964
- Tax Year: 2024
- Directions: Take Generals Hwy to Epping Forest Rd. into Epping Forest gated community. Take Epping Way to circle. Exit circle onto Friar Trail. Continue onto Overlook Trail until the end of road. Home is on your right with 3 gravel parking spaces at top of stairs. Welcome Home!
- Year Built: 1962
- Stories: 3
- Living Area: 3,070 SqFt
- Lot Size: 0.36 Acres
- MLS Number: MDAA2121406
- MLS Name: BRIGHT
- Office Name: Corner House Realty
- Office Phone: (443) 499-3839
- Office Email: aj@cornerhouserealty.com
- Listing Agent: Darrel Reel
- Agent Phone: (443) 759-0222
- Agent Email: darrelreel@reelwaterfrontgroup.com
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Price information
Property sales
Date | Event | Price |
---|---|---|
Mar 04, 2024 | Home Sold | $1,200,000 |
Tax history
Year | Assessment | Property Tax |
---|---|---|
2024 | $758,200 | $3,964 |
2023 | $727,300 | $3,964 |
2022 | $696,400 | $7,277 |
2021 | $653,033 | $5,607 |
2020 | $609,667 | $5,404 |
2018 | $552,967 | $4,783 |
2017 | $539,633 | $4,673 |
History based on county public records data.
Nearby schools
8
Arnold Elementary School
Public District KG-5
1.9 mi
•95 Joyce Ln E
6
Rolling Knolls Elementary School
Public District PK-5
1.9 mi
•1985 Valley Rd
2
Monarch Academy Annapolis Elementary School
Public District KG-5
2.3 mi
•2000 Capital Dr
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 $135,539. The most common annual income of people living in Annapolis, MD is between $35k-100k. The most common type of family is married, no kids. Most residents in this area have post secondary degree education.
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Frequently asked questions
About 357 Overlook Trl
The listing price of 357 Overlook Trl property is $1,398,000.
The property 357 Overlook Trl is a house located in Annapolis, Maryland, 21401.
Coming Soon: 357 Overlook Trl is Coming Soon. This listing has not previously been on the market, but will be on the market soon (no showings are allowed yet). A listing contract has been executed.
The nearby schools for 357 Overlook Trl are: Arnold Elementary School (GreatSchools Rating 8/10), Rolling Knolls Elementary School (GreatSchools Rating 6/10), Monarch Academy Annapolis Elementary School (GreatSchools Rating 2/10), Magothy River Middle School (GreatSchools Rating 9/10), Severn River Middle School (GreatSchools Rating 8/10), Wiley H. Bates Middle School (GreatSchools Rating 5/10), Annapolis High School (GreatSchools Rating 3/10), Anne Arundel Evening High School (GreatSchools Rating 1/10), Severna Park High School (GreatSchools Rating 9/10).
According to the records, the last property tax for 2024 is $3,964 (source: MLS/based on county public records data).
The last sale was on March 4, 2024 for $1,200,000 (source: MLS/tax record).
The property at 357 Overlook Trl has 4 bedrooms and 4 bathrooms.
The property 357 Overlook Trl is 3,070 SqFt (source: MLS/tax record).
The year of construction for 357 Overlook Trl is 1962.
This home is located at 357 Overlook Trl in Annapolis, MD and zip code 21401 in the Parole neighborhood. This 3,070 square foot home, which was built in 1962, sits on a 0.36 acre lot. Features: 4 bedrooms, 4 bathrooms. It has been listed on Rocket Homes since July 26, 2025 and is currently priced at $1,398,000.
The number of listings in Annapolis, MD increased by 63.5% between May and June 2025. The median list price of listings available in June 2025 was $699,900, while the average time on the real estate market was 64 days.