Chester MD Real Estate & Homes for Rent

The "Gibson's Grant" Waterfront Community has a new Rental Home available! They don't come on the market that often in this desired neighborhood... so don't delay! This Stunning 3 BR, 2.5BA, single family home is ready for you to move right in! Full of upgrades to include a Custom Stone Fireplace Surround and Mantel, Hardwood floors, Granite Countertops, SS Appliances, Beautiful Tiled Backsplash, Extensive Crown Moldings and more! Enjoy lazy afternoons on the covered front porch or delight in the fenced in backyard with custom paver patio for BBQ and party time! Garage floor is upgraded and houses a built-in Desks for the work at home folks! Enjoy the plethora of community amenities to include the Swimming pool, Clubhouse, Playground, Walking Trail, Kayak Launch, Fishing & Crabbing Pier, Fitness Room, Bonfire and Grilling area overlooking the Chester River! *Pets are considered on a case by case basis*

Awesome water front living on Cox Creek! This wonderful, spacious Home is a must see on Kent Islands in popular Bentons Pleasure Neighborhood! HUGE GREAT ROOM AND PRIMARY BEDROOM/BATH ADDITION! Wonderful open concept kitchen/ dining room & great room combo w/stone fireplace, handsome built-in book cases, Brazilian cherry hardwood floors, recessed lighting, custom wet bar, wine cooler and water views with gorgeous sunsets! The home has 3 decks, unspoiled water views and pier access to Cox Creek, Eastern Bay and The Chesapeake!! Fully equipped gourmet kitchen featuring granite and stainless steel appliances plus huge island breakfast bar! Master bedroom w/water views, spa bathroom, laundry and large walk-in closet! Perfect extended family/In-Law or home office opportunity with level private entrance including bedroom & bath. Recent well( one year) and associated pump and plumbing! Current Mortgage holder does not require flood insurance; buyer/buyer's to determine any future need. Excellent protected water with ample depth 3-4 feet mean low water at the recently constructed pier! Bring the boat and jet skiis!

Welcome to this charming home located in the quiet, established community of Harbor View in Chester. This well-maintained property features a bright and open floor plan with a cozy fireplace-perfect for relaxing evenings. The kitchen comes fully equipped with modern appliances. Enjoy the convenience of an attached garage and a spacious 0.34-acre lot with plenty of outdoor space. Situated just minutes from the Bay Bridge, this home offers an easy commute to Annapolis, Baltimore, and DC while providing a peaceful retreat on Kent Island.

Welcome to this charming home located in the quiet, established community of Harbor View in Chester. This well-maintained property features a bright and open floor plan with a cozy fireplace - perfect for relaxing evenings. The kitchen comes fully equipped with modern appliances. Enjoy the convenience of an attached garage and a spacious 0.34-acre lot with plenty of outdoor space. Situated just minutes from the Bay Bridge, this home offers an easy commute to Annapolis, Baltimore, and DC while providing a peaceful retreat on Kent Island.

Beautiful, four-bedroom, ranch-style home on level lot with spacious, fenced backyard. Kitchen has stainless steel appliances and granite counters/island. Hardwood floors. Energy efficiency improvements include a fully encapsulated, insulated crawlspace and R49 attic insulation. Quiet street. One small dog considered on case-by-case-basis, additional fee and deposit will apply. PROPERTY AVAILABLE JUNE 1, 2026. NO SHOWINGS BEFORE APRIL 2, 2026. 24-HR NOTICE REQUIRED STARTING APRIL 2. Rental application available online at https://apply.link/1oabTq4

Beautiful, four-bedroom, ranch-style home on level lot with spacious, fenced backyard. Kitchen has stainless steel appliances and granite counters/island. Hardwood floors. Energy efficiency improvements include a fully encapsulated, insulated crawlspace and R49 attic insulation. Quiet street. One small dog considered on case-by-case-basis, additional fee and deposit will apply. PROPERTY AVAILABLE JUNE 1, 2026. NO SHOWINGS BEFORE APRIL 2, 2026. 24-HR NOTICE REQUIRED STARTING APRIL 2. Rental application available online at https://apply.link/1oabTq4

Check the disclosures for application procedures. Discover the charm of this delightful penthouse unit in the serene Queens Landing community. This inviting 2-bedroom, 1.5-bathroom apartment offers a perfect blend of comfort and convenience, making it an ideal place to call home. Step inside to find a spacious layout adorned with Mediterranean architectural style, featuring warm stucco finishes that create a cozy atmosphere. The unit boasts convenient in-unit laundry hookups, ensuring that chores are a breeze. Enjoy the luxury of community amenities that enhance your lifestyle. Take a refreshing dip in the outdoor pool on warm days, or stay active with access to the exercise room and jogging/walking paths. The clubhouse is perfect for social gatherings, while the tennis courts offer a great way to unwind and stay fit. With on-street parking available, youll have easy access to your home. The well-maintained common areas reflect the care and attention of the community management, providing a welcoming environment for all residents. This property, built in 1983, combines classic charm with modern conveniences, making it a wonderful opportunity for anyone seeking a comfortable living space in a vibrant community. Embrace the lifestyle youve been dreaming of in this lovely garden-style apartment, where every day feels like a retreat.

Check the disclosures for application procedures. Discover the charm of this delightful penthouse unit in the serene Queens Landing community. This inviting 2-bedroom, 1.5-bathroom apartment offers a perfect blend of comfort and convenience, making it an ideal place to call home. Step inside to find a spacious layout adorned with Mediterranean architectural style, featuring warm stucco finishes that create a cozy atmosphere. The unit boasts convenient in-unit laundry hookups, ensuring that chores are a breeze. Enjoy the luxury of community amenities that enhance your lifestyle. Take a refreshing dip in the outdoor pool on warm days, or stay active with access to the exercise room and jogging/walking paths. The clubhouse is perfect for social gatherings, while the tennis courts offer a great way to unwind and stay fit. With on-street parking available, you'll have easy access to your home. The well-maintained common areas reflect the care and attention of the community management, providing a welcoming environment for all residents. This property, built in 1983, combines classic charm with modern conveniences, making it a wonderful opportunity for anyone seeking a comfortable living space in a vibrant community. Embrace the lifestyle you've been dreaming of in this lovely garden-style apartment, where every day feels like a retreat.

Showings begin Sunday! Rare waterview end-unit townhouse for rent on Kent Island. Located in Bayside, a sought-after waterfront community on Marylands Eastern Shore, this tucked-away property offers true Chesapeake Bay resort-style living. Residents enjoy a community pool with hot tub, tennis courts, lawn volleyball, scenic walking trails, and a renovated clubhouse with fitness center, kitchen, and activity room. Just a short walk to Castle Harbor Marina, a full-service marina with 347 slips and easy boating access to Annapolis, Baltimore, and St. Michaels. This beautifully renovated 3-bedroom, 3.5-bath home offers over 2,100 square feet and stunning Chester River views from all three levels. Features include bi-level Trex decks, updated kitchen with quartz countertops and stainless steel appliances, and a remodeled primary bath with spa-style shower and double marble vanity. The open main level offers LVP flooring, gas fireplace, custom built-ins, vaulted foyer ceiling, and access to a spacious rear deck overlooking the water. Upstairs, both bedrooms include en-suite baths, and the primary suite features private deck access with unobstructed water views. The top-level loft provides flexible space for a guest room, office, or bonus area with full bath and walk-in closet. End-unit privacy plus parking for three vehicles, including an attached garage. Lawn care, snow removal, trash service, and exterior maintenance included. Convenient to waterfront dining and routes- to Annapolis, DC, and Baltimore. Offered partially furnished.

Showings begin Sunday! Rare waterview end-unit townhouse for rent on Kent Island. Located in Bayside, a sought-after waterfront community on Maryland's Eastern Shore, this tucked-away property offers true Chesapeake Bay resort-style living. Residents enjoy a community pool with hot tub, tennis courts, lawn volleyball, scenic walking trails, and a renovated clubhouse with fitness center, kitchen, and activity room. Just a short walk to Castle Harbor Marina, a full-service marina with 347 slips and easy boating access to Annapolis, Baltimore, and St. Michaels. This beautifully renovated 3-bedroom, 3.5-bath home offers over 2,100 square feet and stunning Chester River views from all three levels. Features include bi-level Trex decks, updated kitchen with quartz countertops and stainless steel appliances, and a remodeled primary bath with spa-style shower and double marble vanity. The open main level offers LVP flooring, gas fireplace, custom built-ins, vaulted foyer ceiling, and access to a spacious rear deck overlooking the water. Upstairs, both bedrooms include en-suite baths, and the primary suite features private deck access with unobstructed water views. The top-level loft provides flexible space for a guest room, office, or bonus area with full bath and walk-in closet. End-unit privacy plus parking for three vehicles, including an attached garage. Lawn care, snow removal, trash service, and exterior maintenance included. Convenient to waterfront dining and routes - to Annapolis, DC, and Baltimore. Offered partially furnished.

Awesome water front living on Cox Creek! This wonderful, spacious Home is a must see on Kent Islands in popular Bentons Pleasure Neighborhood! HUGE GREAT ROOM AND PRIMARY BEDROOM/BATH ADDITION! Wonderful open concept kitchen/ dining room & great room combo w/stone fireplace, handsome built-in book cases, Brazilian cherry hardwood floors, recessed lighting, custom wet bar, wine cooler and water views with gorgeous sunsets! The home has 3 decks, unspoiled water views and pier access to Cox Creek, Eastern Bay and The Chesapeake!! Fully equipped gourmet kitchen featuring granite and stainless steel appliances plus huge island breakfast bar! Master bedroom w/water views, spa bathroom, laundry and large walk-in closet! Perfect extended family/In-Law or home office opportunity with level private entrance including bedroom & bath. Recent well( one year) and associated pump and plumbing! Current Mortgage holder does not require flood insurance; buyer/buyer's to determine any future need. Excellent protected water with ample depth 3-4 feet mean low water at the recently constructed pier! Bring the boat and jet skiis!

1 bedroom 1 bath apartment in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING building. Pets under 35lbs welcome with pet rent of $50 per month. Closet on balcony is mechanical room and not storage.

1 bedroom 1 bath apartment in Chester. Close to everything Kent Island. Secure building, keyless entry, 1 parking space per unit with plenty of overflow for one additional per unit. Large kitchens, full size washer & dryers in each unit. Water & sewer included. This is a NO SMOKING building. Pets under 35lbs welcome with pet rent of $50 per month. Closet on balcony is mechanical room and not storage.