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417 CHESAPEAKE AVENUE, ANNAPOLIS, MD, 21403

$1,495,000

3 beds
2 full baths
1 half baths
2,077 sq. ft

417 CHESAPEAKE AVENUE, ANNAPOLIS, MD, 21403
$1,495,000 Active Open House JUST LISTED

Beds 3
Baths 2.5
Sq. ft 2,077

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Active Open House JUST LISTED

Open House: 05/10 1:00pm to 3:00pm

This exceptional 3-bedroom, 2.5-bath sun-drenched contemporary home sits on a spacious Eastport corner lot. Enjoy the vibrant Eastport lifestyle from your newly updated, well-maintained oasis featuring warm hardwood floors and generous living, dining, and kitchen areas. The open layout complements the coastal Eastport vibe, while the inviting wraparound porch is great for morning coffee or an evening cocktail. The living room's focal point is a gas fireplace that reflects off the beautiful wood floors and opens to the gourmet kitchen and newly designed dining area. The second level is dedicated entirely to the spacious primary spa-inspired suite with an oversized walk-in closet, custom built-ins, and an updated sublime bath with walk-in shower and heated floors. A hidden laundry room adds convenience. The private east-facing deck overlooks the rear yard, offering stunning sunrises to start your day. The third level features two bedrooms and an elegant shared bath, with one bedroom enjoying winter water views. The fourth-floor loft can serve as a bedroom, office, or exercise space. The expansive back patio and side yard are ideal for BBQs and soaking in the Eastport atmosphere. Two highly coveted off-street parking spaces are a rare find. Stroll Eastport streets, dine at five-star restaurants, enjoy cozy pubs, or watch boating activity from street-end parks. You're moments from yacht clubs and marinas. Downtown Annapolis and the Naval Academy are close by via the charming Spa Creek drawbridge or the iconic water taxi. The Eastport peninsula is flanked by two creeks with quick access to the Severn River and Chesapeake Bay. Annapolis offers charm and sophistication with colleges, music venues, galleries, street fairs, acclaimed boat shows, and proximity to two major cities. Much of the home was updated to a high standard in 2024-25. Located just 5 miles from Route 50 and 97, you'll have direct access to BWI and Washington, DC. Welcome home to your Eastport dream!

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Open Houses

Date	Start Time	End Time	Type	Url
05/10	1:00 pm	3:00 pm	N/A	N/A

Property Features

Year Built:
1979

Days on Market:
1

Listing ID:
MDAA2144320

Bathrooms:
2 full , 1 half

List Date:
May 09, 2026

Property Type:
Single Family Residential

Architecture Style:
Coastal

Subdivision:
EASTPORT

County:
ANNE ARUNDEL

Appliances:

Total Taxes:
$15,702

Courtesy of Coldwell Banker Realty

This content was last updated on May 09, 2026 16:52

Name	Type	Level	Grades	Address

Address: Enrollment
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
Eastport Elementary School	Public	Primary	PK-5	420 Fifth St, Annapolis, MD 21403
District: Anne Arundel County Public Schools Grade Span: PK - 5 Admission: Public Address: 420 Fifth St, Annapolis, MD 21403 Phone: 410-222-1605 Website: http://eastportelementaryschoolmd.com/ Teachers: 27 Students: 283 Ratio: 10:1 Students/Teacher Gender: 60% Male / 40% Female Lunch: 77% Free / 12% 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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417 CHESAPEAKE AVENUE, ANNAPOLIS, MD, 21403

$1,495,000