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2144 CHESAPEAKE HARBOUR DRIVE, ANNAPOLIS, MD, 21403

$1,495,000

3 beds
3 full baths
1 half baths
2,016 sq. ft

2144 CHESAPEAKE HARBOUR DRIVE, ANNAPOLIS, MD, 21403
$1,495,000 Active JUST LISTED

Beds 3
Baths 3.5
Sq. ft 2,016

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Active JUST LISTED

Welcome to 2144 Chesapeake Harbour Drive a stunning end-unit townhome in the sought-after community of Chesapeake Harbour. Perfectly positioned to overlook the Chesapeake Harbour Marina and with Chesapeake Bay views, this move-in-ready home combines luxurious updates with an exceptional waterfront lifestyle. The main level features a beautifully updated kitchen with marble countertops, stainless steel appliances, upgraded finishes and even a serene view of the Bay. The kitchen flows seamlessly into the dining area and spacious living room, where an electric fireplace creates a warm and inviting atmosphere. Sliding doors lead to a private deck overlooking the marina, providing the perfect place to enjoy your morning coffee or unwind at sunset. A convenient half bathroom completes this level. Upstairs, the spacious primary suite offers a walk-in closet and a beautifully renovated private bathroom with a walk-in shower. A second bedroom, a fully updated hall bathroom, and an upper-level laundry area complete this floor. The top level features a private third bedroom with separate aircon unit, creating an ideal space for guests, a home office, or whatever best fits your needs. The walkout lower level provides even more flexible living space with a cozy family room featuring a wood-burning fireplace and access to a private patio with marina views. There is also a wet-bar with wine cooler, making this room perfect for entertaining. The attached garage has been enhanced with custom epoxy flooring and built-in storage cabinets, creating a polished and functional space. Nearly every inch of this home has been thoughtfully updated in recent years, including new Marvin windows and sliding doors, custom window coverings, luxury vinyl plank flooring, custom stair railings, marble kitchen countertops, beautifully renovated bathrooms, new lighting fixtures, and a new LG washer and dryer. The roof was replaced in 2025, and the community is completing fresh exterior painting this year, adding even more value and curb appeal. Chesapeake Harbour offers an unmatched amenity package, including an outdoor pool with water views, tennis and pickleball courts, a private beach, and beautifully maintained common grounds. Residents also enjoy plenty of parking for both owners and guests. Just moments away, you'll find local favorites such as Beacon Waterfront Galley & Bar, the Annapolis Maritime Museum, Black Market Bakers, nearby parks, shopping, dining, and easy commuter access. If you've been dreaming of a low-maintenance waterfront lifestyle with breathtaking views, resort-style amenities, and designer finishes throughout, this exceptional home is one you won't want to miss. Schedule your private tour today!

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Property Features

Year Built:
1985

Days on Market:
1

Listing ID:
MDAA2151304

Bathrooms:
3 full , 1 half

List Date:
July 17, 2026

Property Type:
Condominium

Architecture Style:
Contemporary

Subdivision:
CHESAPEAKE HARBOUR

County:
ANNE ARUNDEL

Appliances:
Dishwasher, Built-In Microwave, Cooktop, Oven - Wall, Refrigerator, Stainless Steel Appliances, Washer, Dryer

Total Taxes:
$8,851

Courtesy of One Percent Lists Mid-Atlantic

This content was last updated on July 17, 2026 15:12

Name	Type	Level	Grades	Address
Annapolis High School	Public	High	9-12	2700 Riva Rd, Annapolis, MD 21401
District: Anne Arundel County Public Schools Grade Span: 9 - 12 Admission: Public Address: 2700 Riva Rd, Annapolis, MD 21401 Phone: 410-266-5240 Website: http://www.annapolishigh.org/ Teachers: 140 Students: 2075 Ratio: 15:1 Students/Teacher Gender: 47% Male / 52% Female Lunch: 51% Free / 11% Reduced Student/Teacher ratio Enrollment
Annapolis Middle School	Public	Middle	6-8	1399 Forest Dr, Annapolis, MD 21403
District: Anne Arundel County Public Schools Grade Span: 6 - 8 Admission: Public Address: 1399 Forest Dr, Annapolis, MD 21403 Phone: 410-267-8658 Website: http://www.aacps.org/aacps/anms/index.asp/ Teachers: 74 Students: 790 Ratio: 11:1 Students/Teacher Gender: 48% Male / 52% Female Lunch: 72% Free / 13% Reduced Student/Teacher ratio Enrollment
Georgetown East Elementary School	Public	Primary	EE-5	111 Dogwood Rd, Annapolis, MD 21403
District: Anne Arundel County Public Schools Grade Span: EE - 5 Admission: Public Address: 111 Dogwood Rd, Annapolis, MD 21403 Phone: 410-222-1610 Website: http://www.aacps.org/ Teachers: 32 Students: 330 Ratio: 10:1 Students/Teacher Gender: 55% Male / 45% Female Lunch: 75% Free / 15% Reduced Student/Teacher ratio Enrollment

Name	Type	Level	Grades	Address
Book of Life Academy	Private	Elementary	PK-5	913 Cedar Park Rd, Annapolis, MD 21401
Grade Span: PK - 5 Admission: Private Address: 913 Cedar Park Rd, Annapolis, MD 21401 Phone: 410-263-2600 Website: http://www.bookoflifeacademy.com/ Teachers: 10 Students: 58 Ratio: 6:1 Students/Teacher Gender: 47% Male / 53% Female Student/Teacher ratio Enrollment
Chesapeake Montessori School	Private	Elementary	PK-8	30 Old Mill Bottom Rd N, Annapolis, MD 21409
Grade Span: PK - 8 Admission: Private Address: 30 Old Mill Bottom Rd N, Annapolis, MD 21409 Phone: 410-757-4740 Teachers: 8 Students: 78 Ratio: 10:1 Students/Teacher Gender: 37% Male / 63% Female Student/Teacher ratio Enrollment
Key School	Private	Combined Elementary/Secondary	PK-12	534 Hillsmere Dr, Annapolis, MD 21403
Grade Span: PK - 12 Admission: Private Address: 534 Hillsmere Dr, Annapolis, MD 21403 Phone: 443-321-7833 Website: http://www.keyschool.org Teachers: 64 Students: 598 Ratio: 9:1 Students/Teacher Gender: 53% Male / 47% Female Student/Teacher ratio Enrollment
Montessori International Childrens House	Private	Elementary	PK-6	1641 Winchester Rd, Annapolis, MD 21409
Grade Span: PK - 6 Admission: Private Address: 1641 Winchester Rd, Annapolis, MD 21409 Phone: 410-757-7789 Website: http://www.montessoriinternational.org/ Teachers: 10 Students: 75 Ratio: 8:1 Students/Teacher Gender: 47% Male / 53% Female Student/Teacher ratio Enrollment
Naval Academy Primary School	Private	Elementary	PK-5	74 Greenbury Point Rd, Annapolis, MD 21402
Grade Span: PK - 5 Admission: Private Address: 74 Greenbury Point Rd, Annapolis, MD 21402 Phone: 410-757-3090 Website: http://www.napschool.com/ Teachers: 24 Students: 195 Ratio: 8:1 Students/Teacher Gender: 51% Male / 49% Female Student/Teacher ratio Enrollment
Pathways School--Anne Arundel	Private	Secondary	7-12	1819 Bay Ridge Ave Ste 340, Annapolis, MD 21403
Grade Span: 7 - 12 Admission: Private Address: 1819 Bay Ridge Ave Ste 340, Annapolis, MD 21403 Phone: 301-649-0778 Teachers: 4 Students: 30 Ratio: 7:1 Students/Teacher Gender: 53% Male / 47% Female Student/Teacher ratio Enrollment
St Annes School of Annapolis	Private	Elementary	PK-8	3112 Arundel on the Bay Rd, Annapolis, MD 21403
Grade Span: PK - 8 Admission: Private Address: 3112 Arundel on the Bay Rd, Annapolis, MD 21403 Phone: 410-263-8650 Website: http://st.annesschool.org/ Teachers: 20 Students: 234 Ratio: 12:1 Students/Teacher Gender: 66% Male / 34% Female Student/Teacher ratio Enrollment
St Margaret's Day School	Private	Elementary	PK-KG	1605 Pleasant Plains Rd, Annapolis, MD 21409
Grade Span: PK - KG Admission: Private Address: 1605 Pleasant Plains Rd, Annapolis, MD 21409 Phone: 410-757-2333 Website: http://www.st-margarets.org/ Teachers: 2 Students: 33 Ratio: 17:1 Students/Teacher Gender: 48% Male / 52% Female Student/Teacher ratio Enrollment
St Martins Lutheran Church School	Private	Elementary	PK-8	1120 Spa Rd, Annapolis, MD 21403
Grade Span: PK - 8 Admission: Private Address: 1120 Spa Rd, Annapolis, MD 21403 Phone: 410-269-1955 Teachers: 16 Students: 118 Ratio: 7:1 Students/Teacher Gender: 55% Male / 45% Female Student/Teacher ratio Enrollment
St Marys High School	Private	Secondary	9-12	113 Duke of Gloucester St, Annapolis, MD 21401
Grade Span: 9 - 12 Admission: Private Address: 113 Duke of Gloucester St, Annapolis, MD 21401 Phone: 410-263-3294 Website: http://www.stmarysannapolis.org/ Teachers: 34 Students: 496 Ratio: 15:1 Students/Teacher Gender: 54% Male / 46% Female Student/Teacher ratio Enrollment
The Harbour School at Annapolis	Private	Combined Elementary/Secondary	1-12	1277 Green Holly Dr, Annapolis, MD 21409
Grade Span: 1 - 12 Admission: Private Address: 1277 Green Holly Dr, Annapolis, MD 21409 Phone: 410-974-4248 Website: http://harbourschool.org Teachers: 26 Students: 184 Ratio: 7:1 Students/Teacher Gender: 57% Male / 43% Female Student/Teacher ratio Enrollment
Weems Creek Nursery School & Kindergarten	Private	Combined Elementary/Secondary	PK-PK	238 Kirkley Rd, Annapolis, MD 21401
Grade Span: PK - PK Admission: Private Address: 238 Kirkley Rd, Annapolis, MD 21401 Phone: 410-266-5522 Teachers: 1 Students: 16 Ratio: 16:1 Students/Teacher Gender: 44% Male / 56% Female Student/Teacher ratio Enrollment

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2144 CHESAPEAKE HARBOUR DRIVE, ANNAPOLIS, MD, 21403

$1,495,000

2144 CHESAPEAKE HARBOUR DRIVE, ANNAPOLIS, MD, 21403$1,495,000 Active JUST LISTED

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2144 CHESAPEAKE HARBOUR DRIVE, ANNAPOLIS, MD, 21403
$1,495,000 Active JUST LISTED