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$1,275,000

  • For Sale
  • Under Contract
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 3,070 Sq. Ft.
  • Updated 4 days ago
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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 positioned on a perfectly elevated 0.39-acre lot, this elegant 4-bedroom, 4-bath residence offers over 3,000 square feet of refined living space spread across three thoughtfully designed levels. Embraced by tranquil wooded surroundings, the home reveals seasonal vistas-lush, leafy treetops in summer, transitioning to sweeping water views in winter, with captivating glimpses throughout the year. A graceful stone stairway with sleek cable railing ascends to the front entrance, framed by lush landscaping and the soothing sounds of nature. This harmonious blend of architecture and setting creates a serene, private retreat-yet it remains just moments from the conveniences of modern living. 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 and heated floor for those winter days. 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. See virtual tour for the walk to the pier. 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.

Full Property Details for 357 Overlook Trail

General

  • Price: $1,275,000
  • Taxes: $8,682 (2024)
  • Status: Under Contract
  • Type: Single Family
  • Source: BrightMLSMidAtlantic
  • MLS ID: MDAA2132580
  • Updated: 1/12/2026
  • Added to Site: 18 day(s) ago

Interior

  • Interior Features: 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: Yes
  • Number of Fireplaces: 2
  • Fireplace(s): Brick, Fireplace - Glass Doors, Gas/Propane, Insert, Mantel(s)

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4
  • Upper Floor Baths: 2
  • Upper - Full Baths: 2
  • Main Floor Baths: 1
  • Main - Full Baths: 1
  • Lower Floor Baths: 1
  • Lower - Full Baths: 1

Bedrooms

  • Total Bedrooms: 4
  • Bedrooms Upper: 2
  • Bedrooms Lower: 1
  • Bedrooms Main & Up: 1

Other Rooms

  • Laundry: Upper Floor

Additional Information

  • Shared Amenities: Bar/Lounge, Basketball Courts, Beach, Billiard Room, Boat Ramp, Club House, Common Grounds, Fitness Center, Gated Community, Marina/Marina Club, Party Room, Picnic Area, Pier/Dock, Tennis Courts, Water/Lake Privileges

Exterior

  • Exterior Features: Extensive Hardscape, Exterior Lighting
  • Porch/Patio/Deck: Enclosed, Patio(s), Porch(es), Screened

Parking

  • Parking Type: Parking Lot

Location

  • County: ANNE ARUNDEL
  • Subdivision: EPPING FOREST
  • Driving 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!

School Information

  • School District: Anne Arundel County Public Schools
  • Elementary School: Rolling Knolls
  • Middle School: Annapolis
  • High School: Annapolis

Community

  • Association: Yes

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Ceiling Fan(s), Central A/C, Programmable Thermostat
  • Cooling Fuel: Electric
  • Heating Type: Heat Pump(s), Programmable Thermostat
  • Heating Fuel: Propane - Owned
  • Water Heater: Electric

Utilities

  • Sewer: Private Septic Tank
  • Water: Private/Community Water

Structural Information

  • Architectural Style: Craftsman
  • Structure Type: Detached
  • Construction: Combination
  • Basement: Yes
  • Basement Entrance: Yes
  • Basement Desc.: Full, Fully Finished, Heated, Improved, Outside Entrance, Walkout Level, Windows
  • Foundation: Other
  • Stories Description: Lower 1, Main, Upper 1
  • Square Feet: 3,070
  • Sq. Ft. Source: Assessor
  • Living Area: 3,070 Sq. Ft.
  • Finished Above Grnd: 3,070 Sq. Ft.
  • Year Built: 1962
  • Year Built Source: Estimated

Unit Information

Unit 1

  • Bathrooms-Lower: 1
  • Bedrooms-Lower: 1

Lot Features

  • Lot Size (Acres): 0.36
  • Lot Size (Sq. Ft.): 15,783
  • Lot Size Source: Estimated
  • Zoning: R1

Water Features

  • Water Front: Yes
  • Navigable Water: Yes
  • Water Access: Yes
  • Water Access Desc: Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC), Private Access, Sail, Swimming Allowed, Waterski/Wakeboard
  • Water Front Type: River
  • Water Front Name: Severn River/Clements Creek
  • Dock/Slip Conveys: Yes
  • Docks: 1

Financial Considerations

  • Price Per Sq. Ft.: $415.31
  • Assessment Year: 2025
  • County Tax: $8,302
  • County Tax Freq: Annually
  • Tax w/Assessment: $789,100
  • Tax Amount: $8,682
  • Tax Year: 2024
  • Tax Total Finished Sq. Ft.: 2539

Disclosures and Reports

  • Ownership: Fee Simple
  • Section: A
  • Lot Number: 7R

Listed by TTR Sotheby's International Realty, Darrel Reel

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Listing agent

— 357 Overlook Trail —

  • Darrel Reel

    TTR Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 357 Overlook Trail

School District:Anne Arundel County Public Schools
NameGradesDistance
Rolling Knolls Elementary School
1985 Valley Road, Annapolis, MD 21401
PK-51.9 mi
Wiley H. Bates Middle School
701 Chase Street, Annapolis, MD 21401
6-83.4 mi
Annapolis High School
2700 Riva Road, Annapolis, MD 21401
9-123.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 357 Overlook Trail Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/29/2025
Listed
$1,275,000
6.25%
MLS
2/29/2024
Sold
$1,200,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 357 Overlook Trail

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,929
176%
$789,100
4%
2023
$3,964
—
$758,200
4%
2023
$3,964
-46%
$727,300
4%
2022
$7,277
30%
$696,400
7%
2018
$5,607
4%
$653,033
7%
2021
$5,405
3%
$609,667
8%
2020
$5,253
10%
$566,300
2%
2019
$4,783
2%
$552,967
2%
2018
$4,673
2%
$539,633
3%
2017
$4,580
11%
$526,300
6%
2016
$4,139
-3%
$497,433
6%
2015
$4,284
3%
$468,567
7%
2014
$4,151
—
$439,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by TTR Sotheby's International Realty, Darrel Reel

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357 Overlook Trail, Annapolis, MD 21401 (MLS# MDAA2132580) is a Single Family property with 4 bedrooms and 4 full bathrooms. 357 Overlook Trail is currently listed for $1,275,000 and was received on December 29, 2025. Want to learn more about 357 Overlook Trail? Do you have questions about finding other Single Family real estate for sale in Annapolis? You can browse all Annapolis real estate or contact a Coldwell Banker agent to request more information.

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