Entire home
Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly
Photo gallery for Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly





Popular amenities
- Onsite parking available
- Pet-friendly
- Kitchen
- Washing machine
- Air-conditioning
- Barbecue
Explore the area

Annapolis, MD
- Maryland Quiet Waters ParkPlace, Maryland Quiet Waters Park4 min drive
- Bay Bridge Market Place Shopping CenterPlace, Bay Bridge Market Place Shopping Center4 min drive
- Bay Ridge BeachPlace, Bay Ridge Beach7 min drive
- Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)46 min drive
Rooms & beds
4 bedrooms (sleeps 12)
Full Bed Guestroom
1 Double Bed
King Suite
1 King Bed
Main Floor Queen Suite
2 Queen Beds
Waterview Queen Bedroom
2 Queen Beds
3 bathrooms
King EnSuite
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Main Floor Full Bath
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Upper Level Hall Bath
Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer
Spaces
Deck or patio
Kitchen
Balcony
Number of living rooms
About this property
Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly
Experience the Difference: Professionally Managed by iTrip Annapolis
Welcome to All Decked Out, your dream escape in the waterfront Oyster Harbor Community of Annapolis, a tranquil retreat on the Annapolis Neck Peninsula. This beautifully renovated 4-bedroom, 3-bath home blends modern elegance with timeless coastal charm. With sweeping water views, a private pier, multiple decks, and seamless Chesapeake Bay access, this home is perfect for boating enthusiasts, families, and anyone craving tranquility by the water.
Spacious Coastal Living
The open concept layout is designed for gathering and relaxation.
Expansive windows framing serene waterfront views
Waterfront dining room with seating for 6
Chef’s Kitchen
A true entertainer’s kitchen featuring:
Large island with breakfast bar seating for 4
New stainless steel appliances
Ample prep space
Fully stocked with cookware and dinnerware for 12 guests
Coffee bar in the kitchen (plus a second coffee bar in the Dining Room and a third in the King Suite)
Sleeps 12
Main Level
Double Queen Suite (sleeps 4) with en-suite bath with dual access to Living room
Second Level
Waterfront King Suite with luxury bath, sitting room, coffee bar & deck access
Waterfront Double Queen Bedroom (sleeps 4) with deck access
Full Bedroom
Full Hall bath with shower
Outdoor Living
Private dock
Covered deck + upper waterfront deck
Waterfront patio with built-in grill & outdoor kitchen
Water views from multiple rooms
Bring your boat, kayak, or simply enjoy sunset views from the dock.
Community Perks
Guests enjoy access to Oyster Harbor’s beach, fishing pier, boat ramp, playgrounds, nature trails, and exercise course.
Dog-Friendly - $150 non-refundable fee per pet (paid prior to check-in).
Ideal Location
10 minutes to Downtown Annapolis
12 minutes to USNA
Easy access to DC & Baltimore (33 miles)
Parking for 2-4 SUVs/cars in the circular driveway
Perfect for family gatherings, Navy visits, or peaceful waterfront retreats.
Location Highlights:
Nestled in the quiet Oyster Harbor community, this property is minutes from downtown Annapolis, shopping, dining, and entertainment.
Welcome to All Decked Out, your dream escape in the waterfront Oyster Harbor Community of Annapolis, a tranquil retreat on the Annapolis Neck Peninsula. This beautifully renovated 4-bedroom, 3-bath home blends modern elegance with timeless coastal charm. With sweeping water views, a private pier, multiple decks, and seamless Chesapeake Bay access, this home is perfect for boating enthusiasts, families, and anyone craving tranquility by the water.
Spacious Coastal Living
The open concept layout is designed for gathering and relaxation.
Expansive windows framing serene waterfront views
Waterfront dining room with seating for 6
Chef’s Kitchen
A true entertainer’s kitchen featuring:
Large island with breakfast bar seating for 4
New stainless steel appliances
Ample prep space
Fully stocked with cookware and dinnerware for 12 guests
Coffee bar in the kitchen (plus a second coffee bar in the Dining Room and a third in the King Suite)
Sleeps 12
Main Level
Double Queen Suite (sleeps 4) with en-suite bath with dual access to Living room
Second Level
Waterfront King Suite with luxury bath, sitting room, coffee bar & deck access
Waterfront Double Queen Bedroom (sleeps 4) with deck access
Full Bedroom
Full Hall bath with shower
Outdoor Living
Private dock
Covered deck + upper waterfront deck
Waterfront patio with built-in grill & outdoor kitchen
Water views from multiple rooms
Bring your boat, kayak, or simply enjoy sunset views from the dock.
Community Perks
Guests enjoy access to Oyster Harbor’s beach, fishing pier, boat ramp, playgrounds, nature trails, and exercise course.
Dog-Friendly - $150 non-refundable fee per pet (paid prior to check-in).
Ideal Location
10 minutes to Downtown Annapolis
12 minutes to USNA
Easy access to DC & Baltimore (33 miles)
Parking for 2-4 SUVs/cars in the circular driveway
Perfect for family gatherings, Navy visits, or peaceful waterfront retreats.
Location Highlights:
Nestled in the quiet Oyster Harbor community, this property is minutes from downtown Annapolis, shopping, dining, and entertainment.
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

Spacious home with an outdoor pool, screened porch, washer/dryer & central AC
Annapolis
Spacious home with an outdoor pool, screened porch, washer/dryer & central AC
Annapolis
- Pool
- Kitchen
- Washing machine
- Dryer

Zen Sunset Retreat on Waterfront at West River, MD
West River
Zen Sunset Retreat on Waterfront at West River, MD
West River
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (6 reviews)
10/10
Exceptional
(6 reviews)

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
- Washing machine
- Dryer
- Air-conditioning

3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
Bay Ridge
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
Bay Ridge
- Kitchen
- Washing machine
- Dryer
- Pet-friendly

New Luxury Townhome Near Downtown Annapolis with Multiple EnSuite Bedrooms and Parking
Annapolis
New Luxury Townhome Near Downtown Annapolis with Multiple EnSuite Bedrooms and Parking
Annapolis
- Kitchen
- Washing machine
- Dryer
- Pet-friendly

Stay Mins from Annapolis in Luxury Waterfront Home on Deep Water w Private Pier & Gourmet Kitchen
Crownsville
Stay Mins from Annapolis in Luxury Waterfront Home on Deep Water w Private Pier & Gourmet Kitchen
Crownsville
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.0 out of 10, Wonderful, (11 reviews)
9.0/10
Wonderful
(11 reviews)

Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.8 out of 10, Exceptional, (40 reviews)
9.8/10
Exceptional
(40 reviews)

Bayfront Escape in Edgewater with Deck, Balcony, and Walk to Beach
Edgewater
Bayfront Escape in Edgewater with Deck, Balcony, and Walk to Beach
Edgewater
- Kitchen
- Washing machine
- Dryer
- Pet-friendly

Waterview Retreat with Beach Volleyball near Marina and Local Wedding Venues
Stevensville
Waterview Retreat with Beach Volleyball near Marina and Local Wedding Venues
Stevensville
- Ocean view
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (76 reviews)
10/10
Exceptional
(76 reviews)

Serene Sunsets at Historic Waterfront Home
Hillsmere
Serene Sunsets at Historic Waterfront Home
Hillsmere
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.6 out of 10, Exceptional, (33 reviews)
9.6/10
Exceptional
(33 reviews)

Kent Island Luxary Home W/ Pool and walking distance from the beach
Stevensville
Kent Island Luxary Home W/ Pool and walking distance from the beach
Stevensville
- Pool
- Spa pool
- Kitchen
- Washing machine
8.0 out of 10, Very good, (3 reviews)
8.0/10
Very good
(3 reviews)

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
9.6 out of 10, Exceptional, (8 reviews)
9.6/10
Exceptional
(8 reviews)

All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
Eastport
All Newly-Designed Water Views, Expansive Yard, Steps to Restaurants and Downtown Annapolis
Eastport
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (5 reviews)
10/10
Exceptional
(5 reviews)

Oasis by the Bay - Waterfront Heated Pool Hot Tub!
Bay Ridge
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
Bay Ridge
- Pool
- Spa pool
- Kitchen
- Washing machine
8.8 out of 10, Excellent, (6 reviews)
8.8/10
Excellent
(6 reviews)

Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Stevensville
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Stevensville
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
9.8 out of 10, Exceptional, (44 reviews)
9.8/10
Exceptional
(44 reviews)

USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR
Annapolis
USNA Stay w indoor Soft Hot Tub, Private Pool, King Beds & CHILD FRIENDLY GEAR
Annapolis
- Pool
- Spa pool
- Kitchen
- Washing machine
8.0 out of 10, Very good, (5 reviews)
8.0/10
Very good
(5 reviews)

The General's House-Spacious Home w/Pool & Hot Tub
Annapolis
The General's House-Spacious Home w/Pool & Hot Tub
Annapolis
- Pool
- Spa pool
- Kitchen
- Washing machine
10.0 out of 10, Exceptional, (12 reviews)
10/10
Exceptional
(12 reviews)

Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Shady Side
Spacious 6-bedroom country house on the water in beautiful Shady Side with WiFi
Shady Side
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (11 reviews)
10/10
Exceptional
(11 reviews)

Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D
Bay Ridge
Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D
Bay Ridge
- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi

Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
Annapolis
Unique Listing! Entire Downtown Triplex w/Private Parking! Sleeps 12-18. Pets ok
Annapolis
- Spa pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (9 reviews)
10/10
Exceptional
(9 reviews)

Chesapeake Bay Waterfront ARTectural Home
Stevensville
Chesapeake Bay Waterfront ARTectural Home
Stevensville
- Pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (33 reviews)
10/10
Exceptional
(33 reviews)

Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville
Circa 1700 Chesapeake Colonial home on the National Register.
Stevensville
- Pool
- Kitchen
- Washing machine
- Dryer
9.8 out of 10, Exceptional, (57 reviews)
9.8/10
Exceptional
(57 reviews)

Freshly-Renovated Riverfront Retreat with Private Dock, Deck & Yard for the Whole Family - Dogs Too
Edgewater
Freshly-Renovated Riverfront Retreat with Private Dock, Deck & Yard for the Whole Family - Dogs Too
Edgewater
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
5.4 out of 10, (3 reviews)
5.4/10
(3 reviews)

Lots free parking, hot tub, outdoor oasis - NOT party house
Annapolis
Lots free parking, hot tub, outdoor oasis - NOT party house
Annapolis
- Spa pool
- Kitchen
- Washing machine
- Dryer
9.6 out of 10, Exceptional, (30 reviews)
9.6/10
Exceptional
(30 reviews)

Stay by the Chesapeake on Kent Island this Mother Day! < 20 mi from Annapolis.
Stevensville
Stay by the Chesapeake on Kent Island this Mother Day! < 20 mi from Annapolis.
Stevensville
- Spa pool
- Kitchen
- Washing machine
- Dryer
10.0 out of 10, Exceptional, (41 reviews)
10/10
Exceptional
(41 reviews)

Hidden Wine Cellar | Eastport Retreat
Eastport
Hidden Wine Cellar | Eastport Retreat
Eastport
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)

Chessie Cottage-Chesapeake Bay
Great views from easy single floor living!
Stevensville
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Stevensville
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (10 reviews)
10/10
Exceptional
(10 reviews)

Water privileged oasis in the heart of Bayberry- minutes from downtown!
Arnold
Water privileged oasis in the heart of Bayberry- minutes from downtown!
Arnold
- Kitchen
- Pet-friendly
- Free Wi-Fi
- Air-conditioning
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)

Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach
Arundel on the Bay
Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach
Arundel on the Bay
- Kitchen
- Washing machine
- Dryer
- Air-conditioning
10.0 out of 10, Exceptional, (13 reviews)
10/10
Exceptional
(13 reviews)

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
- Kitchen
- Washing machine
- Dryer
- Pet-friendly
10.0 out of 10, Exceptional, (3 reviews)
10/10
Exceptional
(3 reviews)
About the area
Annapolis
Located on the waterfront, this holiday home is in Oyster Harbor, a neighbourhood in Annapolis. The area's natural beauty can be seen at Jonas Green State Park and Smithsonian Environmental Research Center, while Annapolis Maritime Museum and The Colonial Players are cultural highlights. Wild Bird Center and French Soldiers Monument are also worth visiting.

Annapolis, MD
What's nearby
- Maryland Quiet Waters Park - 4 min drive - 3.5 km
- Bay Bridge Market Place Shopping Center - 4 min drive - 3.5 km
- Historical Society of Talbot County - 6 min drive - 4.1 km
- Bay Ridge Beach - 7 min drive - 6.2 km
- Carrs Beach - 9 min drive - 6.2 km
Getting around
- Odenton Station - 29 min drive
- Fort Meade, MD (FME-Tipton) - 31 min drive
Restaurants
- McDonald's - 5 min drive
- Sammy's Italian Pizza Kitchen - 7 min drive
- Royal Farms - 8 min drive
- Starbucks - 5 min drive
- Oscar’s Coffee - 10 min drive
Tell us how we can improve our siteShare feedback