$2,685,000
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3733 Thomas Point RD, Annapolis, MD 21403

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5 Beds
5 Baths
5,082 Sq Ft

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!

Listing By: Bradley R Kappel - TTR Sotheby's International Realty mdbmls-r Realty.com
  • MLS# MDAA2148158
  • Date Listed06/11/2026
  • Days on Realty 79 Days
  • Bedrooms 5
  • Bathrooms 4 Full baths, 1 Half baths
  • Lot Size 0.29 acres (12,540 sq. ft)
  • Subdivision OAKWOOD
  • County Anne Arundel
  • Year Built 2005
  • Square Feet 5,082 sq. ft
  • Price Per Sq. Ft $528.34

Interior Features

  • Cooling Ceiling Fan(s), Central A/C, Programmable Thermostat
  • Heating Forced Air, Heat Pump - Gas BackUp, Programmable Thermostat

Exterior / Lot Features

  • Roof -
  • Lot Size Acres 0.29
  • Lot Size SQFT 12,540.00
  • Lot Features -

Financial Considerations

  • Tax Amount $21,277
  • Terms Cash, Conventional, FHA, VA Loan

Schools near 21403

Explore the local neighborhood highlights and top-rated schools near 21403 in Annapolis, MD.

Nearby Schools

Source: School Digger

West Meade Elementary

Public • PK - KG • Serves this home

28.93 mi

Distance

Crofton Middle School

Public • 6 - 8 • Serves this home

16.78 mi

Distance

Arundel Middle School

Public • 6 - 8

22.56 mi

Distance

Macarthur Middle School

Public • 6 - 8

28.39 mi

Distance

Annapolis High School

Public • 9 - 12 • Serves this home

8.85 mi

Distance

Southern High School

Public • 9 - 12

12.4 mi

Distance

Crofton High School

Public • 9 - 11

16.78 mi

Distance

Arundel High School

Public • 9 - 12

21.37 mi

Distance

Meade High School

Public • 9 - 12

27.86 mi

Distance

Sales & Tax History

Source: Public Records

Local Neighborhood Highlights for 21403

Discover key demographics, population statistics, and environmental insights for the Annapolis, MD area.

Population & Environment

Source: Sperling's Best Places

Walkability in MD / 21403

Source: Walk Score

3/100

Car-Dependent

Walk Score ®

0/100

Minimal Transit

Transit Score ®

26/100

Bikable

Bike Score ®

Overview

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

Walkability averages in the surrounding area

The average walkability score in the surrounding area is Walk Score: 13/100, Transit Score: 4/100, Bike Score: 35/100.

Property Change History

Property Heating updated
List Price decreased from $2,980,000 to $2,685,000
Price Per Square Foot decreased from $586.38 to $528.34
Property description updated with new details
Property description updated with new details
Property Interior Features updated

Points of Interest near 3733 Thomas Point Rd, Annapolis, MD 21403

Frequently Asked Questions for 3733 Thomas Point Rd

Source: Realty.com

3733 Thomas Point Rd, Annapolis, MD 21403 in OAKWOOD, Annapolis, MD 21403 is a single family listed at $2,685,000. Highlights include 5 bedrooms, 5 bathrooms, 5,082 sq. ft., built in 2005, 0.29 acre lot, $528 per sq. ft.. Realty.com has 46 photos, sales history, school insights, and mortgage tools for this listing.

Realty.com has 46 photos of 3733 Thomas Point Rd.

Our records indicate that 3733 Thomas Point Rd was built in 2005.

The full address for this home is 3733 Thomas Point Rd, Annapolis, MD 21403.

3733 Thomas Point Rd has been listed on Realty.com since Thu June 11, 2026

Almost all errands require a car. It is possible to get on a bus. Minimal bike infrastructure.

The average walkability score in the surrounding area is Walk Score: 13/100, Transit Score: 4/100, Bike Score: 35/100.

There are 3 schools assigned to this home. Check out the schools near 3733 Thomas Point Rd. West Meade Elementary (Grades: PK - KG), Crofton Middle School (Grades: 6 - 8), Annapolis High School (Grades: 9 - 12)

Listing provided courtesy of: Ttr Sotheby's International Realty (tel: 410-280-5600)
Listing agent: Bradley Kappel (#3022116)

This content last refreshed on 2026-08-29 21:40:49. Some properties which appear for sale on this web site may subsequently have sold or may no longer be available.