Shady Side MD Real Estate & Homes for Rent

Interior photos available soon, can be shown. Charming waterfront studio apartment located in a small, peaceful marina. This unique space features a full kitchen and a large, sun-filled main room with a loft-ideal for a cozy sleeping area or storage. Please note: the unit does not have a private bathroom. However, tenants have access to two updated marina bathrooms with showers located just outside the studio door. Currently being renovated, the unit will have a brand-new mini split HVAC. Enjoy serene waterfront living in a truly one-of-a-kind setting. Walk to Skippers Pier and enjoy easy access to other local restaurants, grocery store, hardware/marine shops, and antique boutiques. Landscaping included in rent. Pets case by case. $50/mo pet rent per pet.

Charming 3 bedroom, 2 full bath home located within a quiet marina. Currently undergoing a top-to-bottom renovation, including fresh exterior and interior paint, two brand-new bathrooms, new flooring on the main level, and beautifully refinished hardwood floors upstairs. The kitchen features crisp white cabinetry. Step outside to your own fenced stone patio overlooking the water-perfect for relaxing evenings by the Bay. Enjoy serene waterfront living in a truly one-of-a-kind setting. Walk to Skippers Pier and enjoy easy access to other local restaurants, grocery store, hardware/marine shops, and antique boutiques. Landscaping included in rent. Pets case by case. $50/mo pet rent per pet.

Home was completely rebuilt and updated in 2008. Second story addition adds lots of light and architectural appeal. Home has an in-law suite. Home sits just one block from the Chesapeake Bay; community offers fishing pier and great water views! Over 4,000 sq ft of finished living area. Master bedroom has vaulted ceilings and sauna in master bath! Many of the materials were reclaimed from a historic building in DC including the beautiful hardwood floors on the upper levels. Large level lawn, nearly half an acre and partially fenced. One of two large sheds available for tenants use. Pets case by case. $50 pet rent per pet.

Waterfront home in Oakwood Community w/ unsurpassed views of S. River and Bay. Newly renovated gourmet kitchen w/ island. Main level 2 BR 1 bath. Spacious open living area, F/R with wood-burning F/P. Hard wood FL through out. 2-Car garage w/ lots of workspace and storage. New 100 foot pier. Tranquil location, steps from Thomas Point Park. Pets case.

Amazing waterfront residence on the Chesapeake Bay with almost 360 degree water views of the Chesapeake Bay, Fishing Creek, and South River. Enjoy a quiet and friendly neighborhood with private beaches and a pier for your boat across the street. Never hassle with bay bridge traffic and enjoy a unique location which is 5 miles to downtown Annapolis, 5 minutes to major retail and restaurants, and a 45 minute drive to downtown Baltimore and Washington DC. The open floor plan provides a great room with cathedral ceilings, hardwood floors, an updated gourmet kitchen, a dining area, and a wood burning fireplace all with panoramic bay views of the bay bride and Thomas Point Light House. A deck off the great room provides a perfect spot to enjoy the bay breeze, to watch the water life of the Chesapeake, and to see spectacular sights of the stars and moon over the bay at night. Up a few steps, you will find the large master bedroom with en-suite bath, large walk-in closet, and views of Fishing Creek through large windows. 2 additional bedrooms, a 2nd full bath, and laundry closet complete this level. Ground level foyer, 2-car attached garage, and storage shed complete the property. 2+ year lease preferred. See agent notes for Tenant responsibility.

Views of the Great Chesapeake Bay come with this updated and upgraded Oyster Creek waterfront. Shared pier with a large boat slip, community beach and boat ramp for easy water access to the Bay. No smoking house and no pets allowed.

Move-in ready. Luxurious 3 Level Colonial Town Home with 2600+ sqft. in a Highly Desired South River Colony. This beautiful home features 3 bedrooms, 4 baths, new floors, newer carpet, fresh paint, Open layout with lots of natural light, a beautiful kitchen with a dual-wall oven (self-cleaning), large center island, recessed lighting, crown molding, gas cooktop, 2 gas fireplaces, deck off the family room. Upstairs you have an expansive master suite with two large walk-in closets, a master bath with dual vanities, a shower and a sep. soak in tub, 2 additional bedrooms, and a full bath. On the lower level you have a large finished basement that could be used as a rec room or a man cave, with a full bath, and a walkout to the brick patio, attached 2 car garage provides plenty of space for parking and storage. The home backs to woods, on a quiet street, the community features clubhouse, tennis courts, pool and more. Hurry book a showing appointment today, this one will be available for move in on or after September 1st.

Annapolis Stunning Contemporary - Located in the highly sought-after waterfront community of Anchorage, this stunning 3,000+ square foot contemporary 4-bedroom/3-bathroom home offers the perfect blend of architectural sophistication, modern upgrades, and serene coastal living. Main level living and open layout floor plan at its finest! This elegant home sits on a professionally landscaped corner lot and has a 2-car garage. Enjoy exclusive community amenities, including a private dock, newly raised boat slips, boat ramp, and a waterfront pool overlooking Lake Ogleton and the marina. A rare lifestyle opportunity just minutes from downtown Annapolis. The home boasts impeccable curb appeal, with pristine steps leading to an etched glass front door. Step into the elegant marble foyer, adorned with a compass rose inlay, skylights, and ambient recessed lighting, setting the tone for the refined details throughout. Enjoy main-level living at its finest; highlighted by a Great Room, recessed lighting, and double sliding doors that open to a screened-in porch complete with skylights, a hot tub rough-in, and a block platform ready for hot tub installation. From the porch step out onto a 14 x 16 IPE Brazilian mahogany architect designed deck; featuring a solid hardwood support structure, grilling area, and stair access to a professionally landscaped, meticulously manicured backyard. In addition, there is a climate-controlled dry storage areas below the great room and another storage below the deck (each approx. 20 x 20) which offer abundant space for water toys, tools, and seasonal items. The remodeled, open layout kitchen is a showpiece featuring white Corian countertops, Travertine tile backsplash, bar-height countertop with breakfast bar seating, upgraded white shaker cabinetry, stainless appliances and a sun-filled breakfast nook with ceiling fan. Off the kitchen enjoy a versatile room (family room, dining room or office) with a wood burning fireplace. The expanded owners suite is a true retreat featuring skylights, recessed lighting, walk-in closet, and direct access to the screened-in porch, ideal for morning coffee. The en-suite bath showcases Carrara marble tile flooring, a glass-enclosed shower, Carrara marble vanity and abundant natural light. An additional main-level bedroom and fully remodeled hall bath feature marble tile, a 60-inch custom vanity with marble top, a Mother of Pearl-framed mirror, and a soaking tub. The lower level with mostly ceramic tile flooring; features a cozy family/recreation room with fireplace and built-ins, two bedrooms, a full hallway bathroom and office area, plus a laundry/utility room with direct access to a two-car garage. Additional upgrades include; plantation shutters on most windows, hardwood and bamboo flooring throughout the main level, tray ceilings and crown molding, professionally painted walls and ceilings, Dual HVAC systems (Trane & Carrier) and architectural shingle roof. Set on a beautifully landscaped corner lot with year-round perennials, this remarkable property offers an unmatched lifestyle in a prestigious Annapolis location. Located in the highly sought-after Anchorage Waterfront community, residents enjoy exceptional amenities with an HOA fee of just $118/month, which includes access to a boat slip, marina, boat ramp, community pool, rack for kayaks and paddle boards and a half basketball court. Currently two boat slips available (06/06/25). Home is offered fully furnished. Dont miss your chance to call Anchorage home!

A charming move in ready colonial, ready for you to call home, in a neighborhood where your neighbors are friends you just haven't met yet. Home is also listed for sale (MLS number MDAA2100650) You'll want to experience this beautiful home nestled in SRL's handsome, 24-hr guard gated community. Lovingly maintained with a gourmet kitchen, 3 bdrms each with private baths, cozy fireplaces and more. Enjoy the seasonal beautify of its park-like setting in this nonriparian community. Enjoy walking trails, marina, pool and tennis courts. Easy commute to DC, Annapolis and Baltimore.

Welcome to this freshly painted, move-in ready 2-bedroom, 2-bathroom ground floor condo in the highly desirable Fairwinds community. This home offers warm hardwood floors throughout the main living areas, fresh paint in the dining room, living room, and hallway, and a functional open layout thats ideal for both daily living and entertaining. The Fairwinds community is known for its peaceful setting, well-maintained grounds, and unbeatable location close to shopping, dining, and major commuter routes.

Stunning condo featuring 1 bedroom, 1 bathroom, and a dedicated office space or could be additional bedroom, all conveniently located on the step-free main level. Just 7 minutes from downtown Annapolis and 2 minutes from Quiet Waters Park and the dog beach. Enjoy a relaxing patio in the back-an ideal spot in an unbeatable location! Ground level for convenience. Available august 1st

PRICE REDUCED - Lovely ground-level 2 Br/ 2 Ba unit renovated condo @ Fairwinds Condominiums. Sunken living room and updated vinyl plank floors throughout; Huge master bathroom with master bath and walk-in closet; granite countertops in the kitchen; stainless steel appliances and nice white cabinets. Updated bathrooms with lovely vanities, granite vanity tops, and beautiful ceramic decor. The condo complex offers plenty of parking, a large outdoor pool, tennis courts, and tot lots. Walking distance to Lovely ground-level 2 Br/ 2 Ba unit renovated condo @ Fairwinds Condominiums. Sunken living room and updated vinyl plank floors throughout; Huge master bathroom with master bath and walk-in closet; granite countertops in the kitchen; stainless steel appliances and nice white cabinets. Updated bathrooms with lovely vanities, granite vanity tops, and beautiful ceramic decor. The condo complex offers plenty of parking, a large outdoor pool, tennis courts, and tot lots. Walking distance to grocery stores, shopping, and eateries. Easy access to parks (Quiet Waters and Back Creek), which offer great views, a dog park, lots of hiking trails, and canoeing. Gas and Water utilities are included in the rent; electric is paid by the tenant separately. A PET IS ALLOWED ON A CASE-BY-CASE BASIS. NO SMOKING IS ALLOWED. REQUIREMENTS: THE APPLICATION FEE IS $50.00 PER ADULT 18 YEARS OR OLDER. MIN CREDIT SCORE 600 OR HIGHER, MINIMUM INCOME 3 TIMES THE AMOUNT OF THE MONTHLY RENT & NO MORE THAN A 40% DEBT-TO-INCOME RATIO, BACKGROUND CHECK, VERIFICATION OF EMPLOYMENT, AND VERIFICATION OF RENT. AVAILABLE IMMEDIATELY!

Updated, second floor 2-bedroom 2-full bath condo, conveniently located near local shopping restaurants and Quiet Waters Park. Annapolis Overlook offers an outdoor pool and fitness room. Well maintained and ready for July 01 occupancy! No pets.

Don't miss this opportunity to live in a recently upgraded 3-bedroom, 2.5-bathroom townhouse/duplex in the sought-after Mariners Point community! This home offers the perfect blend of modern comfort and prime location, spanning over 1,900 square feet of well-appointed living space. The heart of the home is the beautifully renovated kitchen, complete with sleek stainless steel appliances. You'll love the warmth of hardwood floors, the convenience of a newer heat pump, and the serenity of a private master bathroom. A bonus is the finished basement, providing ample room for all your needs. Step outside to your private oasis! A large deck and patio are perfect for entertaining, leading to a fully fenced and surprisingly secluded backyard with an extra storage shed. Beyond your doorstep, the Mariners Point community offers a sparkling pool and welcoming clubhouse for residents to enjoy. Living here means unparalleled access to everything you love about Annapolis. You'll be conveniently close to Downtown Annapolis, with a myriad of shopping, dining, parks, and marina options right at your fingertips. Available July 1st, 2025. A 24-month lease term is preferred, and high credit is required. Small dogs may be considered on a case-by-case basis. This property is Agent Owned. Showings are by appointment only. Apply today via RentSpree: https://apply.link/TyVLSDc

Welcome to this beautifully renovated and cozy home, offering modern updates and timeless charm. Enjoy the open-concept kitchen and living area featuring abundant cabinetry, a breakfast bar, granite countertops, and energy-efficient stainless-steel appliances. The spacious bathroom includes stylish tile flooring, an updated vanity, and modern lighting. Nestled in the quiet and established neighborhood of Primrose Acres, this home boasts a fully fenced yard and a covered back patio-perfect for outdoor dining or relaxing. Conveniently located just minutes from downtown Annapolis and Eastport, with easy access to major routes to Washington, D.C. and Baltimore. Turnkey and ready for immediate occupancy-don't miss out on this gem!

Incredible waterfront apartment available for rent. This unit has been fully renovated and features a gourmet kitchen with granite countertops, custom cabinetry and high end stainless appliances. Directly off the kitchen there is a large area for a dining room table. There is a huge Living room with walls of glass to take in the breathtaking views of Crab Creek. Additionally, there is a wood burning fire place for those cold winter nights. Primary bedroom features screened in porch with unparalleled views. Guest bedroom features new flooring and ceiling fan. Both baths have been fully renovated. Rear bath features double vanity with granite top and incredible shower with custom tile work and multiple nozzles . Laundry area with storage. Incredible huge patio is perfect for entertaining and you won't believe the views. Storage is available for tenant above the garage. The tenant will have access to the patio, backyard and pier upon signature of liability waiver. Perfect spot to drop a kayak in. The tenant will have the opportunity to store a SUP board kayak on the kayak rack. The tenant also has two designated gravel parking spots in front of the home. PLEASE NOTE THIS IS A MAIN LEVEL APARTMENT IN THE REAR OF THE PROPERTY. The owners retain use of the upper two levels and use this residence as a second home. Tenant to be responsible for 1/3 of the utilities (electric, oil) tenant responsbile for 1/2 of internet/cable.

Sunny Luxury 2 Bedrooms 2 Baths Condo with Water Views in Desired Annapolis Community - Available NOW! This stunning bright condo unit home has an open floor with a fireplace, two balconies and a wall of windows along with recessed lighting. The kitchen is modern and fabulous with white granite countertops, tile backsplash, cooktop range and stainless-steel appliances. The common areas have hardwood plank floors and unit has a stackable washer and dryer. Unit provides lots of storage closet space and 2 Bedrooms located in the rear of the unit with a Primary Suite which includes a private rear deck overlooking woods and water. The condo is set in a secluded peaceful community with woods and water views along Chesapeake Bay and Lake Heron with a community pool. Within a 4-minute drive allows access to several water taxi stops to take you over to Ego Alley to enjoy the vibrant waterfront scene. The area offers a rich history of Annapolis by visiting the nearby historic sites and landmarks, breathtaking views and charming atmosphere. The rent includes water/sewer/trash and condo fees. Small pets will be considered case by case for additional monthly fee. This is a non-smoking unit.

Available NOW- excellent credit a must and pets are case by case. Stunning single family home in the private enclave of highly sought after Primrose Hill. This six year old custom Craftmark Home checks all the boxes for the discriminating buyer: elevator serving all three floors; spacious kitchen with oversized island; quartz countertops; custom cabinetry; open plan main level with gas fireplace; large first floor office or den; four large bedrooms on second floor, two with ensuite bathrooms; massive private primary suite (19.5 x 21.5) with cathedral ceiling plus room-sized primary closet; wonderful primary bath with two vanities, large walk in shower and free standing tub; nine foot ceilings throughout, including basement; full basement with unlimited possibilities: legal fifth bedroom and full bath roughed in; room for large family room, shop, and storage; oversized two car garage and two parking pad spots; energy efficient Certified Green Building; spacious outdoor community spaces, with all grounds maintained by HOA. All of this within walking distance to Pip Moyer Recreation Center, Eastport, downtown Annapolis, shopping, dining, public boat ramp, tennis and pickleball courts.

Imagine having your next cup of coffee, absorbing the breathtaking sunrise and warm breeze on your private wrapped balcony/porch. Welcome to 1121 Tyler Ave- Unit 1A, offering 1 bedroom, 1 full bathroom with a separate living room with custom floor to ceiling built-ins, vaulted ceilings, private entrance and designated off-street parking. This bright, airy and rare opportunity is located less than 5mins away from the United States Naval Academy, and a short walk/bike ride to the heart of downtown Annapolis. Great location within walking distance to local restaurants and shops. ****************************** The rare opportunity to live in Eastport is within your reach. Known for maritime living, Eastport offers exceptionally breathtaking views. Enjoy the Chesapeake, touch the water at a street-end park, be sure to bring your kayak (or rent one). Tenants also enjoy a parking pad, in-home laundry and a kitchenette. This fully furnished rental truly has it all! Fully stocked with linens, pots pans, coffee machine, in-unit laundry, vacuum, the list goes on! *******************ALL UTILITIES INCLUDED************************NO PETS****************************

Welcome home to Gemini Drive! Located in the sought after community of North Green and close to everything DTA, this 1 bedroom 1 bath condo offers an open layout and is just steps away from the community pool for Summer fun, and extra privacy off season. Inside you'll find a kitchen with ceramic tile floors, stainless steel appliances, and granite countertops that opens to a sunny breakfast nook with a built-in storage bench, that is just perfect for morning coffee or tea. Continuing through you'll find a dining room with hardwood floors, custom moulding and chair rail, a living room with a large storage closet, hardwood floors, and sliding door entry to the back patio. A generously sized primary suite with dual closets and a full bath completes the unit. The minimum credit score for all adult occupants/applicants is 650 - no exceptions. Pets will be considered on a case by case base with additional pet rent added at a minimum of $50 per month. This is a non smoking unit and liability and renter's insurance are required prior to move in.

Welcome to 1318 Bay Ridge Avenue - a beautifully updated home located in the heart of Annapolis' vibrant Eastport neighborhood. This 3-bedroom, 2.5-bath rental offers the perfect blend of historic charm and modern convenience, just minutes from downtown, marinas, and all the waterfront dining Annapolis is known for. Step inside to find beautiful floors, an open-concept living and dining area, and a stylishly remodeled kitchen with stainless steel appliances and granite countertops. A convenient half bath is located on the main level, perfect for guests. Upstairs, youll find three spacious bedrooms and two full bathrooms, including a primary suite with a private en-suite bath and generous closet space. The fully finished basement adds a versatile rec room - ideal for a home office, gym, or media room. Outside, enjoy your morning coffee or evening unwind on the covered front porch or entertain guests on the back deck overlooking a fenced yard - perfect for pets or summer barbecues. Garage parking and in-home laundry complete the package. Whether you're commuting to D.C. or just want to be close to the water and Annapolis events, this home is a rare Eastport gem you wont want to miss!

Bike to downtown Annapolis from this freshly painted and updated gem. Ground level 2 BR, 1 Full Bath apartment with an enclosed porch, in-unit laundry . Main floor Apartment of 2-Unit building in Eastport. New kitchen including appliances, LVP flooring, large yard (grass cutting included in rent), cute front porch. Sq. ft. is approximately 1156. Qualifying criteria include minimum 600 credit score and $69,825 annual income. W/S included in rent. The off-street parking is the driveway on the right of the unit.

One-of-a-kind Waterfront Luxury in Annapolis, Maryland! Secluded on 2.59 lush, park-like acres along the shores of one of the Chesapeake Bays most serene and protected tributaries, this exceptional estate offers an unparalleled blend of privacy, elegance, and premier waterfront living rarely found in Annapolis. From the moment you arrive down the tree-lined drive, a sense of calm and sophistication sets in. With 185 feet of pristine shoreline, deep water, and a private pier with boat lift, this is more than a home, its a relaxing destination where every day feels like a retreat. Spanning over 12,000 square feet, this custom-built estate (main floor finished in 2014 by Pyramid Builders, lower level in 2019 by Bayview Builders) is crafted with the highest-quality materials and top-of-the-line features. Every detail has been curated with uncompromising quality to deliver a life of luxury, comfort, and effortless entertaining. This resort-like home is built to host-from elegant galas with ample onsite parking to relaxed family weekends. Inside, sunlit spaces and radiant-heated floors create a warm, welcoming atmosphere throughout the year. The grand two-story foyer with custom millwork ceiling opens to formal living and dining rooms, while the heart of the home-a soaring great room with fireplace-anchors the space with timeless beauty and comfort. A chefs dream kitchen is equipped for both daily living and high-end entertaining, featuring Sub Zero refrigerators and wine cooler, Wolf stove/griddle and double ovens, dual dishwashers, warming drawers, catering entrance, ample custom cabinetry, and expansive granite countertops. Whether preparing an intimate dinner or a large event, this space delivers excellence. For gathering and unwinding, the custom mahogany bar with private balcony overlooking the waterfront and pool is located on the main floor and connects to the kitchen by the great room-perfect for serving pre-dinner cocktails or spreading out larger gatherings. A comfortable family room and sunroom off the kitchen overlook the waterfront and pool providing relaxing sunset views. A main-level guest suite with private balcony ensures both comfort and privacy for visitors while a sun-filled custom wood paneled office with fireplace provides an impressive and inspiring executive workspace at home. Ascend the stunning curved staircase to the primary suite for a serene escape with water views and attention to all your needs with sitting room, fireplace, dual dressing rooms, a private balcony, and a spa-like en-suite bath. Three additional en-suite bedrooms, a laundry room and an upper-level library offer generous, luxurious accommodations for family and guests. The newly finished walkout lower level feels like its own private coastal escape: game room, kitchenette, home gym, a 2nd laundry room, pool bath, sauna, and guest quarters with private entry-perfect for an au pair, in-laws, or long-term visitors. Step outside and discover a resort caliber setting: a heated saltwater pool and hot tub surrounded by travertine patios, Ipe decks, and outdoor dining areas that invite celebration and quiet reflection alike. Cruise effortlessly from your backyard to the Chesapeake Bay, South River, Annapolis Harbor and St. Michaels for waterfront dining or explore the many nearby creeks and coves. Whether you're boating, catching crabs off the dock, taking in the bald eagles during sunset, or paddling into calm morning waters, the connection to nature and the water here is effortless. Conveniently located just minutes from downtown Annapolis and within easy reach of commuter routes to Washington, D.C. and Baltimore, this extraordinary estate defines luxury living. This is more than a home-its an estate that offers a luxurious lifestyle immersed in nature, rooted in comfort, and ready to be shared. Embrace this rare opportunity to own an exclusive piece of Annapolis where luxury meets tranquility!

BEAUTIFUL HOME JUST 150' FROM CHESAPEAKE BAY!! GRANITE & STAINLESS KITCHEN IS OPEN TO FAMILY ROOM WITH FIREPLACE. HARDWOOD ENTIRE 1ST FLOOR,. SUPER BATH OFF MASTER BEDROOM PLUS 2 WALK IN CLOSETS . BALCONY OFF MASTER BEDROOM WITH WATER VIEW OF CHESAPEAKE BAY. DECK OFF FAMILY ROOM. FENCED REAR YARD. NEW CARPET INSTALLED JUNE 2024. 1.5 MILES OF WATER FRONT IN THIS COMMUNITY THAT IS AVAILABLE TO RESIDENTS TO WALK AND ENJOY.

At last, a private and peaceful home with minimal maintenance perfect for the Commuter or those wishing to downsize. Located just 10 minutes from North Beach and Chesapeake Beach, 35 minutes from Annapolis, 30 minutes from JBAA and within 45 minutes of Washington, DC. This charming home has a timeless floorplan with plenty of natural light. Perfect for someone who works from home! Once you enter the property you'll see a parking pad around the back of the home with space for 4+ vehicles, and more down the driveway. There is a back patio and entrance to the Kitchen, with updated appliances and cabinetry. One side of the house contains a Kitchen and Dining area, with a separate living space in the front of the home. Upon entering the front door and Living Room a left turn will lead you to the Primary Bedroom closet and Dressing Room, leading to the Primary Bedroom. Beyond that is the 2nd Bedroom with closet. At the back of the house is a spacious Laundry Room with stacking HE Samsung Washer & Dryer and additional storage shelves. Your Full Bath is spacious and private. This is a perfect property for rest and rejuvenation, privacy and convenience. Outside is a large gently sloping side and front lawn that meets the wooded property backing to farmland. NO pets allowed. Showings start 6/20 with move-in date by 7/1.