Property photo 1
Property photo 2
Property photo 3
Property photo 4
Property photo 5
5 Beds
5 Baths
5,082 sqft

$2,495,000

3733 Thomas Point Road, Annapolis MD, 21403

Price per sqft$490.95
Built in2005
Property size5,082 sqft
Property typeResidential

Overview

Active

Listed Jun 11, 2026

Updated 26h ago

Life takes on a different pace in Oakwood, where the calm waters of Fishing Creek and the South River provide an idyllic backdrop and effortless access to the Chesapeake Bay. With 93 feet of shoreline, a private pier with multiple slips, and a substantial 25,000-pound boat lift, this property is perfectly suited for boating enthusiasts and those who appreciate the beauty and tranquility of the Chesapeake lifestyle. Designed for both everyday comfort and effortless entertaining, the home offers an inviting open floor plan with seamless flow between the gourmet kitchen with center island, sunroom, soaring two-story living room, and adjacent family room. Walls of windows frame picturesque water views and fill the home with natural light. A versatile main-level room with an adjoining full bath provides ideal space for guests, a private office, or flexible living needs. Upstairs, the spacious primary suite serves as a peaceful retreat with abundant windows capturing the ever-changing waterfront scenery, a walk-in closet, and an ensuite bath featuring dual vanities, a large shower, and a relaxing soaking tub. Two additional bedrooms share an ensuite bath and a fourth bedroom provides plenty of space for family and friends. The expansive space above the garage has been transformed into a fun Margaritaville-inspired bar and game room complete with a full bath. This exceptional area offers endless possibilities and could easily become a second primary suite, private guest quarters, or an in-law suite. Outside, multiple entertaining spaces invite gatherings with family and friends while the lush lawn gently transitions to the water's edge. Whether hosting summer celebrations, launching a boat for a day on the Bay, or simply unwinding as the sun reflects across Fishing Creek, this property offers a lifestyle that feels like a vacation every day. A side-entry two-car garage and spacious driveway complete this exceptional waterfront offering in one of Annapolis Neck's most desirable communities. Welcome Home!

$16,599/mo

Est. mortgage payment based on a $2,495,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
MDAA2148158
Available since
June 11, 2026

Interior Features

Bedrooms
5
Bathrooms
5
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.29 Acres

Other Property Details

Taxes
$21,277
Tax Frequency
Annually

 Courtesy of Brad Kappel | TTR Sotheby's International Realty

Based on information from DASH - Sotheby's International Realty (SIR) as of 10/10/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. The display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent. 

©2026 DASH - Sotheby's International Realty (SIR). All rights reserved. 

Data last updated 7:20 AM UTC, 10/10/2026

Powered by Luxury Presence