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Experience the pinnacle of coastal luxury in this breathtaking top-floor penthouse at K. Hovnanian’s Four Seasons at Kent Island. This highly coveted "Chester" floor plan delivers unparalleled, sun-drenched resort-style living with spectacular water views from nearly every vantage point. The open-concept layout features a gourmet kitchen with stainless steel appliances, a spacious great room anchored by a cozy fireplace, and an elegant dry bar perfect for entertaining. Retreat to the pristine owner's suite, complete with a dramatic tray ceiling, spa-like bath, and direct access to an expansive waterside balcony where you can watch the boats glide by. Living here feels like a permanent vacation. Enjoy world-class community amenities, including a 24,000 sq. ft. clubhouse, indoor and outdoor pools with tiki huts, a state-of-the-art fitness center, tennis and pickleball courts, and a community pier. Complete with a private garage and dedicated storage, this lock-and-leave sanctuary offers the effortless Eastern Shore lifestyle you deserve.

121 Switchgrass Way Unit 42, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

$199,900

Attention Investors, Renovators, and Buyers Looking for Opportunity! Discover the potential of 406 Dominion Road in Chester, Maryland, situated in Queen Anne's County on desirable Kent Island. This property is being sold strictly AS-IS, presenting an opportunity for investors, contractors, and buyers looking to renovate, restore, or customize a home to their vision. Conveniently located near shopping, dining, recreational opportunities, and major commuter routes, including US Route 50/301, providing access to Annapolis. The property is its present AS-IS condition. The seller will make no repairs or improvements. Bring your contractor, your renovation plans, and your imagination to explore the possibilities this Kent Island property has to offer.

Attention Investors, Renovators, and Buyers Looking for Opportunity! Discover the potential of 406 Dominion Road in Chester, Maryland, situated in Queen Anne's County on desirable Kent Island. This property is being sold strictly AS-IS, presenting an opportunity for investors, contractors, and buyers looking to renovate, restore, or customize a home to their vision. Conveniently located near shopping, dining, recreational opportunities, and major commuter routes, including US Route 50/301, providing access to Annapolis. The property is its present AS-IS condition. The seller will make no repairs or improvements. Bring your contractor, your renovation plans, and your imagination to explore the possibilities this Kent Island property has to offer.

406 Dominion Rd, Chester

Listing courtesy of Sell Your Home Services. Contact:

$280,000

Welcome to 411 Merganser Court, a charming 2-bedroom, 2-bath condo in the sought-after Bayside community. This well-maintained home features a cozy gas fireplace, hardwood floors, newer carpet in bedrooms, an updated water heater within the last year and offers the perfect opportunity to enjoy the Eastern Shore lifestyle at an affordable price.Come and check out what this condo has to offer! Enjoy resort-style amenities including a community pool, tennis courts, and more, all just steps from your door. Plus, you're within walking distance to local marinas, waterfront restaurants, shopping, and entertainment. Whether you're looking for a year-round residence, weekend getaway, or low-maintenance living, this Bayside gem is ready for you!

Welcome to 411 Merganser Court, a charming 2-bedroom, 2-bath condo in the sought-after Bayside community. This well-maintained home features a cozy gas fireplace, hardwood floors, newer carpet in bedrooms, an updated water heater within the last year and offers the perfect opportunity to enjoy the Eastern Shore lifestyle at an affordable price.Come and check out what this condo has to offer! Enjoy resort-style amenities including a community pool, tennis courts, and more, all just steps from your door. Plus, you're within walking distance to local marinas, waterfront restaurants, shopping, and entertainment. Whether you're looking for a year-round residence, weekend getaway, or low-maintenance living, this Bayside gem is ready for you!

411 Merganser Ct, Chester

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$396,900

Beautifully and professionally renovated, this charming ranch-style home combines modern updates with the comfort and functionality of a traditional floor plan. Offering 3 bedrooms and 2 full baths, including a private ensuite bath in the primary bedroom, this move-in-ready home has been thoughtfully redesigned . The bright, sunny kitchen features abundant cabinet space, brand-new appliances, and luxury vinyl plank flooring. A sliding glass door opens to a spacious deck overlooking a lovely backyard with mature trees and backs to woods, creating the perfect setting for outdoor entertaining or quiet relaxation.The generous living room showcases beautifully refinished red oak hardwood floors that continue throughout all three bedrooms, adding warmth and timeless appeal. Both bathrooms have been completely renovated with new showers, vanities, sinks, toilets, and luxury vinyl plank flooring.For added peace of mind, major upgrades include a new HVAC system, PEX water lines, recessed lighting throughout, a new hot water heater, water softener, and well pump, all conveniently located in a heated mechanical room. Located in the established Harbor View community, this exceptional home is just minutes from shopping, urgent care, walking trails, and Resturants. Convenient to the Kent Narrows and Bay Bridge. Offering the perfect blend of modern convenience and Eastern Shore charm, 1837 Harbor Drive is truly better than new. Come discover a place you'll be proud to call home and enjoy everything the Eastern Shore lifestyle has to offer. See Floor Plan and Renovations to 1837 Harbor Dr in Documents.

Beautifully and professionally renovated, this charming ranch-style home combines modern updates with the comfort and functionality of a traditional floor plan. Offering 3 bedrooms and 2 full baths, including a private ensuite bath in the primary bedroom, this move-in-ready home has been thoughtfully redesigned . The bright, sunny kitchen features abundant cabinet space, brand-new appliances, and luxury vinyl plank flooring. A sliding glass door opens to a spacious deck overlooking a lovely backyard with mature trees and backs to woods, creating the perfect setting for outdoor entertaining or quiet relaxation.The generous living room showcases beautifully refinished red oak hardwood floors that continue throughout all three bedrooms, adding warmth and timeless appeal. Both bathrooms have been completely renovated with new showers, vanities, sinks, toilets, and luxury vinyl plank flooring.For added peace of mind, major upgrades include a new HVAC system, PEX water lines, recessed lighting throughout, a new hot water heater, water softener, and well pump, all conveniently located in a heated mechanical room. Located in the established Harbor View community, this exceptional home is just minutes from shopping, urgent care, walking trails, and Resturants. Convenient to the Kent Narrows and Bay Bridge. Offering the perfect blend of modern convenience and Eastern Shore charm, 1837 Harbor Drive is truly better than new. Come discover a place you'll be proud to call home and enjoy everything the Eastern Shore lifestyle has to offer. See Floor Plan and Renovations to 1837 Harbor Dr in Documents.

1837 Harbor, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

$559,900

OPEN HOUSE Saturday 10/31/2026 from 11-1pm. COMING SOON in GIBSON'S GRANT!

OPEN HOUSE Saturday 10/31/2026 from 11-1pm. COMING SOON in GIBSON'S GRANT!

227 Gibson Cir, Chester

Listing courtesy of RE/MAX Executive. Contact:

$280,000

This property contains 2-3 lots and has site plans available to make this your dream home! Whether you are considering renovating this rambler home or building a new one; the possibilities are endless! You're seconds away from the local beaches, parks and more that Chester/Stevensville has to offer! Lot size totals .734 of an acre! Private well and public sewer on the property. The house needs a complete renovation so do not go inside the property without owner or listing agent consent.

3 Beds ⋅ 1 Baths

This property contains 2-3 lots and has site plans available to make this your dream home! Whether you are considering renovating this rambler home or building a new one; the possibilities are endless! You're seconds away from the local beaches, parks and more that Chester/Stevensville has to offer! Lot size totals .734 of an acre! Private well and public sewer on the property. The house needs a complete renovation so do not go inside the property without owner or listing agent consent.

1905-1907 Keister Dr, Chester

Listing courtesy of Five Star Real Estate. Contact:

$699,000

Harbor View - This beautiful waterfront home has been completely remodeled in 2026, new siding, new kitchen, new bathrooms, new luxury vinyl flooring. Freshly painted and in move in ready condition.

Harbor View - This beautiful waterfront home has been completely remodeled in 2026, new siding, new kitchen, new bathrooms, new luxury vinyl flooring. Freshly painted and in move in ready condition.

2627 Cecil Dr, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$450,000

Experience the best of Kent Island waterfront living in the sought-after Bayside community of Chester! This beautifully appointed end-unit townhome offers marina water views from every level, a wraparound porch, multiple outdoor living spaces, and three finished levels above grade—all within a resort-style waterfront community designed for easy, low-maintenance living. Step inside to a bright, open-concept main level featuring a spacious living area with a gas fireplace and direct access to the rear deck—the perfect spot to relax and take in the marina views. The kitchen offers a center island, 42" cabinetry, and plenty of space for everyday living and entertaining. A convenient half bath and under-stair storage complete this level. Upstairs, you'll find two generously sized bedrooms, each with its own private ensuite bath. The primary suite feels like a true retreat with a walk-in closet, skylight, separate soaking tub and shower, and a private balcony overlooking the marina. Laundry is conveniently located on the bedroom level as well. The top-floor loft adds even more flexibility, offering a spacious bonus area with its own full bath and 2 walk-in closets—ideal for a third bedroom, guest suite, home office, or additional living space. Additional highlights include brand NEW carpet throughout, plus a one-car garage with storage shelving and extra parking conveniently located just across the street. Even better, the condo fee covers the roof, siding, grounds, and community amenities, allowing you to spend less time on exterior maintenance and more time enjoying the Eastern Shore lifestyle. Residents of Bayside enjoy an impressive collection of amenities, including a clubhouse, fitness center, swimming pool, tennis courts, & walking trails. Ideally situated near the marina, waterfront dining, shopping, golf courses, and major commuter routes, 609 Blenny Lane offers the perfect blend of Eastern Shore charm, waterfront living, and everyday convenience. Come discover the Bayside lifestyle—where marina views, resort-style amenities, and low-maintenance living come together on Kent Island.

3 Beds ⋅ 4 Baths

Experience the best of Kent Island waterfront living in the sought-after Bayside community of Chester! This beautifully appointed end-unit townhome offers marina water views from every level, a wraparound porch, multiple outdoor living spaces, and three finished levels above grade—all within a resort-style waterfront community designed for easy, low-maintenance living. Step inside to a bright, open-concept main level featuring a spacious living area with a gas fireplace and direct access to the rear deck—the perfect spot to relax and take in the marina views. The kitchen offers a center island, 42" cabinetry, and plenty of space for everyday living and entertaining. A convenient half bath and under-stair storage complete this level. Upstairs, you'll find two generously sized bedrooms, each with its own private ensuite bath. The primary suite feels like a true retreat with a walk-in closet, skylight, separate soaking tub and shower, and a private balcony overlooking the marina. Laundry is conveniently located on the bedroom level as well. The top-floor loft adds even more flexibility, offering a spacious bonus area with its own full bath and 2 walk-in closets—ideal for a third bedroom, guest suite, home office, or additional living space. Additional highlights include brand NEW carpet throughout, plus a one-car garage with storage shelving and extra parking conveniently located just across the street. Even better, the condo fee covers the roof, siding, grounds, and community amenities, allowing you to spend less time on exterior maintenance and more time enjoying the Eastern Shore lifestyle. Residents of Bayside enjoy an impressive collection of amenities, including a clubhouse, fitness center, swimming pool, tennis courts, & walking trails. Ideally situated near the marina, waterfront dining, shopping, golf courses, and major commuter routes, 609 Blenny Lane offers the perfect blend of Eastern Shore charm, waterfront living, and everyday convenience. Come discover the Bayside lifestyle—where marina views, resort-style amenities, and low-maintenance living come together on Kent Island.

609 Blenny Ln, Chester

Listing courtesy of Compass. Contact:

$472,500

Waterfront Living at Its Finest – Premier Marina Basin Location in Queen's Landing! Welcome to one of the most desirable waterfront locations in Queen's Landing! Perfectly positioned directly on the marina basin, this exceptional condominium features the **largest floor plan in the community, offering a true three-bedroom layout PLUS a spacious loft**, two-and-a-half baths, and three levels of comfortable living space. With beautiful, unobstructed marina views and the ability to see your own boat right from your home, this property offers the ultimate Kent Island waterfront lifestyle. Freshly painted and move-in ready, the home features a renovated kitchen, generously sized bedrooms, and luxury vinyl plank flooring installed just two years ago throughout the second and third levels. The HVAC system is less than a year old, providing added peace of mind. The spacious loft offers valuable additional living space, perfect for a home office, guest retreat, or recreation area. The waterfront setting is truly what sets this home apart! Step outside onto your private patio and enjoy expansive, unobstructed views of the marina basin. Unlike patios enclosed by eye-level privacy fencing, this outdoor space allows you to fully appreciate the beautiful waterfront scenery, passing boats, and marina activity without visual barriers. Enjoy the same picturesque setting from your deck and bedroom, where you can look out and see your own boat just steps away. Boating enthusiasts, this is an opportunity you won't want to miss. The seller is offering the option to include TWO boat slips with the purchase at no additional cost—a 25-foot slip equipped with a 10,000-pound boat lift AND an impressive 66-foot slip capable of accommodating a substantial vessel. Imagine waking up, looking out your bedroom window, and seeing your boat waiting in the marina! Whether you own a smaller powerboat, a larger yacht, or both, this rare opportunity offers incredible flexibility and convenience. Not a boater? No problem! Both slips are entirely optional. Queen's Landing offers an impressive collection of resort-style amenities, including a waterfront swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and racquetball courts, community gathering spaces, and grilling areas. Enjoy easy access to the Kent Island Cross Island Trail, nearby marinas, waterfront dining, shopping, and all the recreation that makes Kent Island such a desirable place to call home. Conveniently located just minutes from the Chesapeake Bay Bridge, with easy access to Annapolis, Baltimore, and Washington, D.C., this waterfront retreat is equally suited for a primary residence or weekend escape.

Waterfront Living at Its Finest – Premier Marina Basin Location in Queen's Landing! Welcome to one of the most desirable waterfront locations in Queen's Landing! Perfectly positioned directly on the marina basin, this exceptional condominium features the **largest floor plan in the community, offering a true three-bedroom layout PLUS a spacious loft**, two-and-a-half baths, and three levels of comfortable living space. With beautiful, unobstructed marina views and the ability to see your own boat right from your home, this property offers the ultimate Kent Island waterfront lifestyle. Freshly painted and move-in ready, the home features a renovated kitchen, generously sized bedrooms, and luxury vinyl plank flooring installed just two years ago throughout the second and third levels. The HVAC system is less than a year old, providing added peace of mind. The spacious loft offers valuable additional living space, perfect for a home office, guest retreat, or recreation area. The waterfront setting is truly what sets this home apart! Step outside onto your private patio and enjoy expansive, unobstructed views of the marina basin. Unlike patios enclosed by eye-level privacy fencing, this outdoor space allows you to fully appreciate the beautiful waterfront scenery, passing boats, and marina activity without visual barriers. Enjoy the same picturesque setting from your deck and bedroom, where you can look out and see your own boat just steps away. Boating enthusiasts, this is an opportunity you won't want to miss. The seller is offering the option to include TWO boat slips with the purchase at no additional cost—a 25-foot slip equipped with a 10,000-pound boat lift AND an impressive 66-foot slip capable of accommodating a substantial vessel. Imagine waking up, looking out your bedroom window, and seeing your boat waiting in the marina! Whether you own a smaller powerboat, a larger yacht, or both, this rare opportunity offers incredible flexibility and convenience. Not a boater? No problem! Both slips are entirely optional. Queen's Landing offers an impressive collection of resort-style amenities, including a waterfront swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and racquetball courts, community gathering spaces, and grilling areas. Enjoy easy access to the Kent Island Cross Island Trail, nearby marinas, waterfront dining, shopping, and all the recreation that makes Kent Island such a desirable place to call home. Conveniently located just minutes from the Chesapeake Bay Bridge, with easy access to Annapolis, Baltimore, and Washington, D.C., this waterfront retreat is equally suited for a primary residence or weekend escape.

21 Queen Victoria Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

$349,900

ASSUME A 2.875% FHA LOAN * $1777 MO PYMT *BAYSIDE IN CHESTER/KENT ISLAND * GARAGE TOWNHOME * PRICED TO SELL EXCELLENT OPPORTUNITY TO ASSUME AN FHA 2.875% FIXED INTEREST RATE * Qualified Owner Occupant Buyers: Take Advantage of this rare opportunity to assume this FHA Loan with approximately 25 years remaining * TOTAL PITI PAYMENT OF $1777.56 PER MONTH* You'll Be Way Ahead of the Interest Rate Game AND Own a Spacious 3 Level Garage Townhome in the Popular Community of Bayside with 3 Bedrooms, 2.5 Baths, Deck off Living Room & Propane Gas Fireplace. The Primary Bedroom has a walk-in closet, vaulted ceilings and an ensuite full bath with shower stall and skylight. The Main Level has a spacious open layout with bright and sunny front Kitchen featuring upgraded counters, stainless steel appliances, ample cabinet space and pass through to bar seating on the Dining Room side. The Living Room faces towards the back with Sliders to a Deck great for grilling. Bayside Offers Great Community Amenities to include outdoor pool, exercise room, tennis and volleyball, on-site management AND walking distance to Castle Harbor Marina.

ASSUME A 2.875% FHA LOAN * $1777 MO PYMT *BAYSIDE IN CHESTER/KENT ISLAND * GARAGE TOWNHOME * PRICED TO SELL EXCELLENT OPPORTUNITY TO ASSUME AN FHA 2.875% FIXED INTEREST RATE * Qualified Owner Occupant Buyers: Take Advantage of this rare opportunity to assume this FHA Loan with approximately 25 years remaining * TOTAL PITI PAYMENT OF $1777.56 PER MONTH* You'll Be Way Ahead of the Interest Rate Game AND Own a Spacious 3 Level Garage Townhome in the Popular Community of Bayside with 3 Bedrooms, 2.5 Baths, Deck off Living Room & Propane Gas Fireplace. The Primary Bedroom has a walk-in closet, vaulted ceilings and an ensuite full bath with shower stall and skylight. The Main Level has a spacious open layout with bright and sunny front Kitchen featuring upgraded counters, stainless steel appliances, ample cabinet space and pass through to bar seating on the Dining Room side. The Living Room faces towards the back with Sliders to a Deck great for grilling. Bayside Offers Great Community Amenities to include outdoor pool, exercise room, tennis and volleyball, on-site management AND walking distance to Castle Harbor Marina.

107 Widgeon Way, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$915,000

Absolutely Stunning Custom Home in Gibson’s Grant! Welcome to this beautifully appointed custom home featuring an open floor plan, wide-plank solid red oak hardwood flooring throughout the main level, and timeless architectural details. The main-level primary suite offers a private office/ possible sitting room, creating the perfect blend of comfort and functionality. The inviting kitchen features custom cabinetry, distinctive hardware, and a spacious pantry. The breakfast room opens to a sun-filled sunroom with custom brick pavers, privacy sheers, sliding doors, and skylights that welcome natural light throughout the day. A welcoming dining area with elegant wainscoting provides the perfect setting for entertainment. Upstairs, you’ll find three generously sized bedrooms and two full baths, along with a beautiful, spacious staircase. Custom plantation shutters throughout the home, a sound system, and soothing coastal-inspired colors create a warm, relaxing atmosphere. Enjoy the privacy of the rear yard with cedar fencing, a two-car garage, and additional parking. Experience the Gibson’s Grant Lifestyle! Residents enjoy wonderful community amenities, including a swimming pool, clubhouse, walking paths, kayak launch areas, and a community pier. Conveniently located near restaurants, shopping, and major highways, Gibson’s Grant offers the perfect combination of accessibility, charm, and a peaceful neighborhood setting. Close setting to walking trails, shopping, route 50 and bridge. A truly special home offering custom craftsmanship, thoughtful design, and an exceptional lifestyle!

4 Beds ⋅ 4 Baths

Absolutely Stunning Custom Home in Gibson’s Grant! Welcome to this beautifully appointed custom home featuring an open floor plan, wide-plank solid red oak hardwood flooring throughout the main level, and timeless architectural details. The main-level primary suite offers a private office/ possible sitting room, creating the perfect blend of comfort and functionality. The inviting kitchen features custom cabinetry, distinctive hardware, and a spacious pantry. The breakfast room opens to a sun-filled sunroom with custom brick pavers, privacy sheers, sliding doors, and skylights that welcome natural light throughout the day. A welcoming dining area with elegant wainscoting provides the perfect setting for entertainment. Upstairs, you’ll find three generously sized bedrooms and two full baths, along with a beautiful, spacious staircase. Custom plantation shutters throughout the home, a sound system, and soothing coastal-inspired colors create a warm, relaxing atmosphere. Enjoy the privacy of the rear yard with cedar fencing, a two-car garage, and additional parking. Experience the Gibson’s Grant Lifestyle! Residents enjoy wonderful community amenities, including a swimming pool, clubhouse, walking paths, kayak launch areas, and a community pier. Conveniently located near restaurants, shopping, and major highways, Gibson’s Grant offers the perfect combination of accessibility, charm, and a peaceful neighborhood setting. Close setting to walking trails, shopping, route 50 and bridge. A truly special home offering custom craftsmanship, thoughtful design, and an exceptional lifestyle!

202 Claiborne St, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$275,000

Welcome to easy, low-maintenance living in the sought-after Bayside community of Chester! This beautifully maintained 2-bedroom, 2-bathroom condo offers the perfect combination of comfort, style, and convenience. Gorgeous hardwood floors flow throughout, while the spacious family room, kitchen, and dining area create an inviting layout perfect for everyday living and entertaining. Both bedrooms offer generous space, with the primary suite featuring a walk-in closet and private full bathroom. Enjoy the fresh air and beautiful weather from your private deck, while convenient in-unit laundry adds to the ease of everyday living. The Bayside community offers fantastic amenities, including a clubhouse, fitness center, and outdoor pool, along with easy access to the Cross Island Trail for walking, running, and biking. Conveniently located just minutes from local dining, shopping, and the Chesapeake Bay Bridge. Don't miss your opportunity to enjoy all that Kent Island living has to offer!

Welcome to easy, low-maintenance living in the sought-after Bayside community of Chester! This beautifully maintained 2-bedroom, 2-bathroom condo offers the perfect combination of comfort, style, and convenience. Gorgeous hardwood floors flow throughout, while the spacious family room, kitchen, and dining area create an inviting layout perfect for everyday living and entertaining. Both bedrooms offer generous space, with the primary suite featuring a walk-in closet and private full bathroom. Enjoy the fresh air and beautiful weather from your private deck, while convenient in-unit laundry adds to the ease of everyday living. The Bayside community offers fantastic amenities, including a clubhouse, fitness center, and outdoor pool, along with easy access to the Cross Island Trail for walking, running, and biking. Conveniently located just minutes from local dining, shopping, and the Chesapeake Bay Bridge. Don't miss your opportunity to enjoy all that Kent Island living has to offer!

101 Bufflehead Ct, Chester

Listing courtesy of The KW Collective. Contact:

$545,000

Beautiful 3BR/2.5BA Townhome nestled in the desirable waterfront community of Bayside Marina. Pull into your private driveway in front of the attached one-car garage, which offers convenient direct access into your home. Make your way to the covered front porch, open the door, and step inside a beautifully maintained, move-in-ready home. The main level welcomes you with an open-concept design, featuring beautiful wood-tone flooring, recessed lighting, elegant crown molding, abundant natural light, and a neutral color palette throughout. The spacious living room offers a cozy fireplace feature, creating a warm and inviting atmosphere while flowing seamlessly into the dining area and kitchen, making this an ideal space for everyday living and entertaining. The kitchen features abundant cabinetry accented with crown molding, a separate pantry closet, granite countertops, a complementary tiled backsplash, and stainless steel appliances. A center island with breakfast seating provides the perfect spot for casual dining or morning coffee. A conveniently located half bath completes the main level. Upstairs on the second floor, you'll find a spacious secondary bedroom featuring double closets, convenient access to a shared full bathroom, and second-floor laundry. Make your way upstairs to the second floor, where you'll find a spacious secondary bedroom featuring double closets and convenient access to a shared full bathroom. The grand-sized primary suite offers a relaxing retreat, complete with sliding glass doors that open to a private balcony overlooking the community, a large walk-in closet, and a private en suite featuring a jetted soaking tub and a separate walk-in shower. Continue to the third floor, where a generously sized bedroom provides flexible living space to suit your needs. Whether you envision a private home office, a child's playroom, or a comfortable guest bedroom, this versatile space offers endless possibilities. From the sliding glass doors on the main level, step outside onto a spacious covered deck, perfect for outdoor dining, entertaining, or simply relaxing while taking in the beautiful surrounding landscape and peaceful water sounds. The deck leads down to a green space, offering an inviting connection to the outdoors and the charm of waterfront community living. Beautifully maintained and move-in ready, this home offers comfort, versatility, and an inviting setting, all conveniently located near shopping, restaurants, and commuter routes.

Beautiful 3BR/2.5BA Townhome nestled in the desirable waterfront community of Bayside Marina. Pull into your private driveway in front of the attached one-car garage, which offers convenient direct access into your home. Make your way to the covered front porch, open the door, and step inside a beautifully maintained, move-in-ready home. The main level welcomes you with an open-concept design, featuring beautiful wood-tone flooring, recessed lighting, elegant crown molding, abundant natural light, and a neutral color palette throughout. The spacious living room offers a cozy fireplace feature, creating a warm and inviting atmosphere while flowing seamlessly into the dining area and kitchen, making this an ideal space for everyday living and entertaining. The kitchen features abundant cabinetry accented with crown molding, a separate pantry closet, granite countertops, a complementary tiled backsplash, and stainless steel appliances. A center island with breakfast seating provides the perfect spot for casual dining or morning coffee. A conveniently located half bath completes the main level. Upstairs on the second floor, you'll find a spacious secondary bedroom featuring double closets, convenient access to a shared full bathroom, and second-floor laundry. Make your way upstairs to the second floor, where you'll find a spacious secondary bedroom featuring double closets and convenient access to a shared full bathroom. The grand-sized primary suite offers a relaxing retreat, complete with sliding glass doors that open to a private balcony overlooking the community, a large walk-in closet, and a private en suite featuring a jetted soaking tub and a separate walk-in shower. Continue to the third floor, where a generously sized bedroom provides flexible living space to suit your needs. Whether you envision a private home office, a child's playroom, or a comfortable guest bedroom, this versatile space offers endless possibilities. From the sliding glass doors on the main level, step outside onto a spacious covered deck, perfect for outdoor dining, entertaining, or simply relaxing while taking in the beautiful surrounding landscape and peaceful water sounds. The deck leads down to a green space, offering an inviting connection to the outdoors and the charm of waterfront community living. Beautifully maintained and move-in ready, this home offers comfort, versatility, and an inviting setting, all conveniently located near shopping, restaurants, and commuter routes.

100 Schooner Way, Chester

Listing courtesy of LPT Realty, LLC. Contact:

$699,000

Nestled in the serene Harbor View subdivision, this Colonial-style home offers a perfect blend of luxury and comfort. The interior features elegant bamboo and ceramic tile flooring, enhancing the warm ambiance throughout. The gourmet kitchen is equipped with stainless steel appliances, including a dishwasher, electric oven/range, and refrigerator, making culinary adventures a delight. A charming wood-burning stove adds a touch of warmth to the living space, creating an inviting atmosphere for relaxation. Set on a generous 1.14-acre lot in a peaceful cul-de-sac, the landscaped grounds provide a tranquil retreat. Enjoy stunning water views of Cox Creek, just a short stroll away, where you can indulge in boating and fishing activities. The property includes a private dock with multiple slips, perfect for water enthusiasts. Additional features include an attached garage, off-street parking, and a spacious deck that invites outdoor living. This home is not just a residence; it's a lifestyle, offering the perfect balance of luxury, nature, and community. Experience the exclusive charm of waterfront living in this property.

Nestled in the serene Harbor View subdivision, this Colonial-style home offers a perfect blend of luxury and comfort. The interior features elegant bamboo and ceramic tile flooring, enhancing the warm ambiance throughout. The gourmet kitchen is equipped with stainless steel appliances, including a dishwasher, electric oven/range, and refrigerator, making culinary adventures a delight. A charming wood-burning stove adds a touch of warmth to the living space, creating an inviting atmosphere for relaxation. Set on a generous 1.14-acre lot in a peaceful cul-de-sac, the landscaped grounds provide a tranquil retreat. Enjoy stunning water views of Cox Creek, just a short stroll away, where you can indulge in boating and fishing activities. The property includes a private dock with multiple slips, perfect for water enthusiasts. Additional features include an attached garage, off-street parking, and a spacious deck that invites outdoor living. This home is not just a residence; it's a lifestyle, offering the perfect balance of luxury, nature, and community. Experience the exclusive charm of waterfront living in this property.

2703 Sherman Dr, Chester

Listing courtesy of Rosendale Realty. Contact:

$400,000

Shore living doesn’t get much better than this! Wake up in this waterfront community perfectly tucked along the Chester River in the vibrant community of Queens Landing. Enjoy the easy, breezy coastal lifestyle with open living spaces, a sunlit kitchen, and a spacious primary suite with a private balcony and cozy fireplace. Private balcony offers the perfect spot for your morning coffee or evening cocktails—all with peaceful pond views you’ll never get tired of and two patios for your own private peaceful time outdoors. This two bedroom two bath end unit has been fully updated with a beautiful kitchen. Located just minutes from Route 50, this home is a commuter’s dream while still feeling like a vacation every day. Plus, you’ll have access to incredible amenities like a waterfront pool, marina, clubhouse, fitness center, walking trails, and tennis and pickleball courts—all part of the Queens Landing lifestyle. Easy walkable access to the Cross Island Trail that offers beautiful scenic views. Start living the Shore life you’ve always dreamed of—endless opportunities for boating, fishing, kayaking and crabbing. It's a perfect blend of small town charm, outdoor living, waterfront restaurants, marinas and easy access to Route 50 for a quick trip to Annapolis or DC or the beach! 100% Financing Options For Qualified Buyers!

Shore living doesn’t get much better than this! Wake up in this waterfront community perfectly tucked along the Chester River in the vibrant community of Queens Landing. Enjoy the easy, breezy coastal lifestyle with open living spaces, a sunlit kitchen, and a spacious primary suite with a private balcony and cozy fireplace. Private balcony offers the perfect spot for your morning coffee or evening cocktails—all with peaceful pond views you’ll never get tired of and two patios for your own private peaceful time outdoors. This two bedroom two bath end unit has been fully updated with a beautiful kitchen. Located just minutes from Route 50, this home is a commuter’s dream while still feeling like a vacation every day. Plus, you’ll have access to incredible amenities like a waterfront pool, marina, clubhouse, fitness center, walking trails, and tennis and pickleball courts—all part of the Queens Landing lifestyle. Easy walkable access to the Cross Island Trail that offers beautiful scenic views. Start living the Shore life you’ve always dreamed of—endless opportunities for boating, fishing, kayaking and crabbing. It's a perfect blend of small town charm, outdoor living, waterfront restaurants, marinas and easy access to Route 50 for a quick trip to Annapolis or DC or the beach! 100% Financing Options For Qualified Buyers!

1 Queen Victoria Ct, Chester

Listing courtesy of Douglas Realty LLC. Contact:

$489,900

Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

Welcome to 2011 Stevens Drive — a completely renovated home offering exceptional one-level living with a spacious, open floor plan and a long list of thoughtful upgrades throughout. From top to bottom, this home has been transformed with modern finishes, new flooring, fresh paint, updated lighting, renovated bathrooms, and a beautifully redesigned kitchen. The oversized kitchen features quartz countertops, updated appliances, abundant cabinetry, and plenty of workspace, with a large laundry room conveniently located just off the kitchen. Just off the kitchen, a beautifully appointed private dining room provides an elegant space for entertaining and hosting gatherings. With its versatility, this room could also serve as a sophisticated home office, library, or additional flex space to suit your lifestyle. The expansive living room is truly a showstopper, featuring dramatic 30-foot ceilings, recessed lighting, a fireplace, and an open, airy feel that makes the space perfect for both everyday living and entertaining. New LVP flooring flows throughout the entire home, complemented by all-new lighting fixtures and fresh paint throughout. The spacious primary suite offers a private retreat with a walk-in closet, a beautifully updated bathroom with a double quartz vanity, and a rare feature — direct access to the rear deck. Step outside from the primary suite and enjoy views overlooking the peaceful, wooded rear yard. Two additional bedrooms provide plenty of flexibility, including an oversized bedroom with its own walk-in closet. Both bathrooms have been completely updated with new vanities and quartz countertops. Additional improvements include a brand-new roof with a 30-year warranty, an oversized two-car attached garage, abundant storage, and thoughtful updates throughout. With its expansive living spaces, impressive ceiling height, renovated kitchen and baths, private wooded setting, and exceptional primary suite, 2011 Stevens Drive delivers refined, turnkey one-level living at its finest.

2011 Stevens Dr, Chester

Listing courtesy of Samson Properties. Contact:

$789,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

830 Warbler Way Unit 2843, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$749,990

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in March 2027, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in March 2027, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

830 Warbler Way Unit 2824, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$744,900

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, electric fireplace, and dry bar cabinets with top shelf glass doors. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing. Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and outdoor pools, scenic Chester River walking trails just steps from the property, and a vibrant Clubhouse featuring fitness and exercise classes, pickleball, tennis and bocce courts. wellness lectures, mahjong and other board games, numerous social gatherings, and an array of activities designed to bring neighbors together. With the ease of low-maintenance condo living, beautiful waterfront surroundings, convenient access to local marinas, and easy connectivity to the Bay Bridge and points beyond, this penthouse captures the very best of the Eastern Shore lifestyle—elevated, effortless, and truly exceptional

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, electric fireplace, and dry bar cabinets with top shelf glass doors. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing. Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and outdoor pools, scenic Chester River walking trails just steps from the property, and a vibrant Clubhouse featuring fitness and exercise classes, pickleball, tennis and bocce courts. wellness lectures, mahjong and other board games, numerous social gatherings, and an array of activities designed to bring neighbors together. With the ease of low-maintenance condo living, beautiful waterfront surroundings, convenient access to local marinas, and easy connectivity to the Bay Bridge and points beyond, this penthouse captures the very best of the Eastern Shore lifestyle—elevated, effortless, and truly exceptional

111 Marshgrass Way Unit 43, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$308,000

107 Lee Rd is a one-story Chester home with a streamlined layout and a fully fenced backyard. The kitchen provides ample counter space, white cabinetry, a refrigerator, a range, and a nearby utility nook. The main living area has windows and an open connection to the kitchen, creating flexible space for dining and everyday use. The primary bedroom includes two windows and closet storage, while the bathroom has a vanity and a tub-shower combination. A dedicated laundry area includes a washer and dryer. The broad backyard contains a storage shed, completing this residence with practical interior organization and useful outdoor storage.

3 Beds ⋅ 1 Baths

107 Lee Rd is a one-story Chester home with a streamlined layout and a fully fenced backyard. The kitchen provides ample counter space, white cabinetry, a refrigerator, a range, and a nearby utility nook. The main living area has windows and an open connection to the kitchen, creating flexible space for dining and everyday use. The primary bedroom includes two windows and closet storage, while the bathroom has a vanity and a tub-shower combination. A dedicated laundry area includes a washer and dryer. The broad backyard contains a storage shed, completing this residence with practical interior organization and useful outdoor storage.

107 Lee Rd, Chester

Listing courtesy of Open Door Brokerage, LLC. Contact:

$590,000

Direct Marina Views of Castle Harbor Marina * Watch the Boats and Sunsets from your Deck & Balcony * One-of-a-Kind View * END-UNIT with Garage * Nestled in the prestigious Bayside community, this exquisite end-of-row townhouse offers a harmonious blend of contemporary coastal design and luxurious living. With three spacious bedrooms and three and a half elegantly appointed bathrooms, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The heart of the home features upgraded countertops, a generous kitchen island, and an eat-in space, perfect for casual gatherings. The family room, adorned with a cozy gas fireplace framed by glass doors, creates an intimate atmosphere for relaxation. Recessed lighting and ceiling fans enhance the ambiance, while large windows drench the space in natural light, showcasing the beautiful luxury vinyl plank and ceramic tile flooring. Retreat to the primary suite, where a walk-in closet and a spa-like bathroom with a walk-in shower await, offering a private oasis for unwinding after a long day. Additional bedrooms are equally spacious, ensuring comfort for all. The exterior of the property is equally impressive, featuring a wrap-around porch and a balcony that invite you to enjoy the serene surroundings. The community amenities are unparalleled, including a sparkling outdoor pool, tennis and volleyball courts, and a clubhouse that serves as a hub for social gatherings. With meticulously maintained common areas and professional management, the association fee covers everything from lawn care to snow removal, allowing you to enjoy a carefree lifestyle. Situated on a corner lot, this home offers easy access to the Chester River, perfect for those who appreciate water-oriented living. The nearby recreational facilities and common grounds provide ample opportunities for outdoor activities and relaxation. With an attached garage and secure parking, convenience is at your fingertips. Located just minutes from the airport and local attractions, this property embodies the essence of luxury living in a vibrant community. Experience the perfect blend of comfort, style, and convenience in this stunning Bayside townhouse, where every detail has been thoughtfully curated for an exclusive lifestyle.

3 Beds ⋅ 4 Baths

Direct Marina Views of Castle Harbor Marina * Watch the Boats and Sunsets from your Deck & Balcony * One-of-a-Kind View * END-UNIT with Garage * Nestled in the prestigious Bayside community, this exquisite end-of-row townhouse offers a harmonious blend of contemporary coastal design and luxurious living. With three spacious bedrooms and three and a half elegantly appointed bathrooms, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The heart of the home features upgraded countertops, a generous kitchen island, and an eat-in space, perfect for casual gatherings. The family room, adorned with a cozy gas fireplace framed by glass doors, creates an intimate atmosphere for relaxation. Recessed lighting and ceiling fans enhance the ambiance, while large windows drench the space in natural light, showcasing the beautiful luxury vinyl plank and ceramic tile flooring. Retreat to the primary suite, where a walk-in closet and a spa-like bathroom with a walk-in shower await, offering a private oasis for unwinding after a long day. Additional bedrooms are equally spacious, ensuring comfort for all. The exterior of the property is equally impressive, featuring a wrap-around porch and a balcony that invite you to enjoy the serene surroundings. The community amenities are unparalleled, including a sparkling outdoor pool, tennis and volleyball courts, and a clubhouse that serves as a hub for social gatherings. With meticulously maintained common areas and professional management, the association fee covers everything from lawn care to snow removal, allowing you to enjoy a carefree lifestyle. Situated on a corner lot, this home offers easy access to the Chester River, perfect for those who appreciate water-oriented living. The nearby recreational facilities and common grounds provide ample opportunities for outdoor activities and relaxation. With an attached garage and secure parking, convenience is at your fingertips. Located just minutes from the airport and local attractions, this property embodies the essence of luxury living in a vibrant community. Experience the perfect blend of comfort, style, and convenience in this stunning Bayside townhouse, where every detail has been thoughtfully curated for an exclusive lifestyle.

208 Widgeon Way, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$600,000

Let your home business dreams become a reality! Zoned mixed use residential/commercial! This charming traditional home, offers a perfect blend of comfort and functionality. With 2,818 square feet of thoughtfully designed living space, this residence features five spacious bedrooms and two and a half bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover a cozy family room with wood burning fireplace that seamlessly connects to the kitchen, creating an inviting space for gatherings and everyday living. The kitchen boasts a gorgeous quartz island, perfect for casual meals or entertaining guests as well as a tastefully designed formal dining room. As you move upstairs, you'll find four spacious bedrooms and 2 full bathrooms including a primary suite. Enjoy the luxury of a soaking tub in the primary bathroom, providing a serene escape after a long day. The 3rd floor features an oversized bedroom or recreation room. The possibilities are endless, create a home gym, theatre or gaming room or office space. Outside, the property features a side-entry garage with additional storage space, ensuring convenience and organization. The 0.27-acre lot provides a lovely fenced in outdoor area for gardening or simply enjoying the fresh air. This home is not just a place to live; it's a place to create lasting memories. Experience the perfect blend of style, comfort, and functionality in this delightful residence. Multi-use zoning allows your home business dreams to come true. Zoned residential and commercial.

1616 Postal Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$300,000

Opportunity on Kent Island! Welcome to 205 Dominion Lane in Chester, a detached home situated on a 0.27-acre lot with plenty of potential for the right buyer. Currently used as a rental, this property offers an opportunity for homeowners, investors, or buyers looking to make a home their own. While the property could benefit from some updates and TLC, it provides a chance to add value through improvements and personal touches. Whether you're looking for a primary residence, an investment property, or your next renovation project, this home offers flexibility in a desirable Kent Island location. Enjoy convenient access to shopping, dining, local amenities, and Route 50 for commuting. Bring your vision, explore the possibilities, and schedule your showing today!

Opportunity on Kent Island! Welcome to 205 Dominion Lane in Chester, a detached home situated on a 0.27-acre lot with plenty of potential for the right buyer. Currently used as a rental, this property offers an opportunity for homeowners, investors, or buyers looking to make a home their own. While the property could benefit from some updates and TLC, it provides a chance to add value through improvements and personal touches. Whether you're looking for a primary residence, an investment property, or your next renovation project, this home offers flexibility in a desirable Kent Island location. Enjoy convenient access to shopping, dining, local amenities, and Route 50 for commuting. Bring your vision, explore the possibilities, and schedule your showing today!

205 Dominion Ln, Chester

Listing courtesy of EXP Realty, LLC. Contact:

$1,350,000

Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

4 Beds ⋅ 3 Baths

Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

1509 Calvert Rd, Chester

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$40,000

Looking to own your boat slip instead of paying a hefty lease that could increase year after year? Slip 8-E at Piney Narrows Yacht Haven offers an ownership opportunity in a convenient, community-oriented marina condominium. Measuring 50' x 18' with power, the slip is set beyond a large turnaround area that makes maneuvering easier for larger vessels, including sailboats and sportfish. Located in the heart of Kent Narrows, Piney Narrows Yacht Haven offers a community pool, picnic area with BBQ grill, Yachtsman’s Club lounge, fuel dock with gas and diesel, and complimentary pump-out with fuel purchase. Water, electricity, and Wi-Fi are included. Marina amenities also include winter bubbling at all dock facilities, climate-controlled heads and showers, two laundromats, parking for slip holders and guests, and an on-site canvas shop for new work and repairs. Enjoy convenient access to Kent Narrows restaurants, nearby trails, and popular cruising destinations. Whether you’re seeking a weekend getaway or a home port for the boating season, Slip 8-E offers a comfortable place to enjoy all that Kent Island and the Chesapeake Bay have to offer.

8-E Piney Narrows Rd, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

$570,000

The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly along the Chester River, this end unit delivers huge, panoramic water views that immediately set it apart. The windows are perfectly positioned to take full advantage of the setting, giving you a front-row seat to passing boats, changing skies, and some of the most beautiful views on Kent Island. Inside, the home offers a bright, open floor plan with **dual primary suites**, including one conveniently located on the main level—no steps needed for everyday living. The layout ideal for guests, multigenerational living, or simply having a private retreat on each floor. The main level features luxury vinyl plank flooring, an updated kitchen with stainless steel appliances and granite countertops, and a separate bar area with a wine refrigerator. Shiplap accents bring in just the right amount of coastal character while keeping the space comfortable and inviting. Upstairs, the expanded loft has been thoughtfully enclosed, adding approximately 120 square feet of additional living space. There is plenty of room for a family room or media space along with a separate office, reading nook, or flex area. And even from the upper level, those incredible Chester River views remain front and center. Queens Landing offers a true waterfront lifestyle with a clubhouse, heated outdoor pool overlooking the marina and Chester River, fitness center, tennis and pickleball courts, and easy access to the Cross Island Trail. Restaurants, marinas, shopping, and everyday conveniences are nearby, with Route 50 providing easy access to Annapolis, Baltimore, Washington, D.C., and the beaches.

The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly along the Chester River, this end unit delivers huge, panoramic water views that immediately set it apart. The windows are perfectly positioned to take full advantage of the setting, giving you a front-row seat to passing boats, changing skies, and some of the most beautiful views on Kent Island. Inside, the home offers a bright, open floor plan with **dual primary suites**, including one conveniently located on the main level—no steps needed for everyday living. The layout ideal for guests, multigenerational living, or simply having a private retreat on each floor. The main level features luxury vinyl plank flooring, an updated kitchen with stainless steel appliances and granite countertops, and a separate bar area with a wine refrigerator. Shiplap accents bring in just the right amount of coastal character while keeping the space comfortable and inviting. Upstairs, the expanded loft has been thoughtfully enclosed, adding approximately 120 square feet of additional living space. There is plenty of room for a family room or media space along with a separate office, reading nook, or flex area. And even from the upper level, those incredible Chester River views remain front and center. Queens Landing offers a true waterfront lifestyle with a clubhouse, heated outdoor pool overlooking the marina and Chester River, fitness center, tennis and pickleball courts, and easy access to the Cross Island Trail. Restaurants, marinas, shopping, and everyday conveniences are nearby, with Route 50 providing easy access to Annapolis, Baltimore, Washington, D.C., and the beaches.

34 Queen Anne Way Unit A, Chester

Listing courtesy of RE/MAX Executive. Contact:

$790,000

Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, offering true one-level living with no steps, three spacious bedrooms, and the largest garage offered in the community. Unlike many Killarney models featuring two bedrooms and a loft, this home offers three true bedrooms, a dedicated laundry room, and an additional bump-out ideal for a home office or den. The open-concept interior features an Ultra Gourmet Kitchen with quartz countertops, upgraded cabinetry and appliances, double wall ovens, a French-door refrigerator, and a large center island perfect for entertaining. The spacious primary suite includes an Ultra Luxury Spa Bath with a walk-in shower and dual vanities. Tray ceilings, a fireplace, and custom window treatments add to the home's appeal. The oversized garage provides exceptional space for vehicles, a golf cart, and additional storage. Situated on a $55,000 premium homesite, the property enjoys a spacious backyard with generous separation from neighboring homes, offering a wonderful sense of privacy. An expansive custom hardscaped patio creates the perfect setting for outdoor dining, entertaining, and relaxation. Four Seasons at Kent Island offers resort-style 55+ living along the Chester River, featuring a 24,000-square-foot waterfront clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a dog park, fishing pier, transient boat slips, waterfront Tiki Bar, and an active social calendar. With its desirable floor plan, premium homesite, exceptional garage space, and extensive upgrades, this Killarney presents a rare opportunity to enjoy the best of Four Seasons living.

Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, offering true one-level living with no steps, three spacious bedrooms, and the largest garage offered in the community. Unlike many Killarney models featuring two bedrooms and a loft, this home offers three true bedrooms, a dedicated laundry room, and an additional bump-out ideal for a home office or den. The open-concept interior features an Ultra Gourmet Kitchen with quartz countertops, upgraded cabinetry and appliances, double wall ovens, a French-door refrigerator, and a large center island perfect for entertaining. The spacious primary suite includes an Ultra Luxury Spa Bath with a walk-in shower and dual vanities. Tray ceilings, a fireplace, and custom window treatments add to the home's appeal. The oversized garage provides exceptional space for vehicles, a golf cart, and additional storage. Situated on a $55,000 premium homesite, the property enjoys a spacious backyard with generous separation from neighboring homes, offering a wonderful sense of privacy. An expansive custom hardscaped patio creates the perfect setting for outdoor dining, entertaining, and relaxation. Four Seasons at Kent Island offers resort-style 55+ living along the Chester River, featuring a 24,000-square-foot waterfront clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a dog park, fishing pier, transient boat slips, waterfront Tiki Bar, and an active social calendar. With its desirable floor plan, premium homesite, exceptional garage space, and extensive upgrades, this Killarney presents a rare opportunity to enjoy the best of Four Seasons living.

117 Harrier Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

$399,999

Nestled up to vast farm land, this exquisite ranch-style home offers a perfect blend of comfort and sophistication.This residence boasts a well-maintained exterior with charming vinyl siding, inviting you into a space that feels both warm and welcoming. Step inside to discover an open floor plan that seamlessly integrates the kitchen and living areas, creating an ideal setting for both relaxation and entertaining. The luxury vinyl plank flooring flows gracefully throughout, providing a stylish yet durable foundation for your daily life. Natural light pours in, accentuating the spaciousness and warmth of the home. The heart of this residence is undoubtedly the modern kitchen, equipped with SS Appliances that cater to your culinary aspirations. Featuring an electric oven/range, a sleek microwave, and a dishwasher, this kitchen is designed for both functionality and elegance. The refrigerator offers ample storage for all your gourmet ingredients, making meal preparation a delight. With 3 bedrooms and 2 full bathrooms, this home provides plenty of space for comfort and privacy. Updated Ceiling Fans and Lights throughout the home ensure a refreshing atmosphere year-round. Brand New Roof and Water Heater Installed 2024. Step outside to enjoy the inviting patio, new fence, perfect for morning coffee or evening gatherings under the stars. The expansive 0.26-acre lot offers plenty of room for outdoor activities, gardening, or simply enjoying the tranquility of your surroundings. Parking is a breeze with an attached garage and additional driveway space for guests. The gravel driveway adds a rustic charm while ensuring easy access. This property is not just a house; it's a lifestyle. Experience the joy of living in a well-appointed home that combines modern conveniences with a cozy atmosphere. Whether you're hosting friends or enjoying a quiet evening, this residence is designed to meet your every need. Embrace the opportunity to make this beautiful home your own and enjoy the exclusive lifestyle it offers. Sale of this Home is Contingent upon Sellers finding their home of choice.

Nestled up to vast farm land, this exquisite ranch-style home offers a perfect blend of comfort and sophistication.This residence boasts a well-maintained exterior with charming vinyl siding, inviting you into a space that feels both warm and welcoming. Step inside to discover an open floor plan that seamlessly integrates the kitchen and living areas, creating an ideal setting for both relaxation and entertaining. The luxury vinyl plank flooring flows gracefully throughout, providing a stylish yet durable foundation for your daily life. Natural light pours in, accentuating the spaciousness and warmth of the home. The heart of this residence is undoubtedly the modern kitchen, equipped with SS Appliances that cater to your culinary aspirations. Featuring an electric oven/range, a sleek microwave, and a dishwasher, this kitchen is designed for both functionality and elegance. The refrigerator offers ample storage for all your gourmet ingredients, making meal preparation a delight. With 3 bedrooms and 2 full bathrooms, this home provides plenty of space for comfort and privacy. Updated Ceiling Fans and Lights throughout the home ensure a refreshing atmosphere year-round. Brand New Roof and Water Heater Installed 2024. Step outside to enjoy the inviting patio, new fence, perfect for morning coffee or evening gatherings under the stars. The expansive 0.26-acre lot offers plenty of room for outdoor activities, gardening, or simply enjoying the tranquility of your surroundings. Parking is a breeze with an attached garage and additional driveway space for guests. The gravel driveway adds a rustic charm while ensuring easy access. This property is not just a house; it's a lifestyle. Experience the joy of living in a well-appointed home that combines modern conveniences with a cozy atmosphere. Whether you're hosting friends or enjoying a quiet evening, this residence is designed to meet your every need. Embrace the opportunity to make this beautiful home your own and enjoy the exclusive lifestyle it offers. Sale of this Home is Contingent upon Sellers finding their home of choice.

117 Wright Rd, Chester

Listing courtesy of Douglas Realty LLC. Contact:

$1,160,000

Price Adjustment + Open House Sun Nov 1st 1-3PM!!! Completely reimagined in 2026, this professionally designed Kent Island retreat combines extensively renovated interior with 1.4 private flat acre lot, a saltwater pool, and a 90-foot pier with direct access to Kirwan Creek. Just five minutes from the Bay Bridge, this 5 bedroom, 3 bath home offer the best of Eastern Shore lifestyle. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle boarding, fishing, crabbing, wildlife and sunset watching. Moving inside the 3,000 square foot home, the original intent of the owner was to create coastal inspired retreat for anyone who walked through the front doors. Each space has been re-imagined with professional interior designer style throughout with coastal wallpaper, nautical colors, custom curtains, trim work, updated light fixtures and more. The main level heart of the home you'll find an updated kitchen with new light countertops, ceramic tile backsplash, and fresh hardware with a sweet breakfast table nook. Off the kitchen is a dedicated dining room space with gorgeous wallpaper and updated lighting overlooking the backyard. Step down to the airy main living room centered by electric fireplace and opening to a stunning all window sunroom overlooking your backyard paradise. The main level front room has been converted to functional main level bedroom and the bathroom was updated to a full main level bathroom. Upstairs, the oversized primary suite is designed as a true private retreat, complete with a dedicated lounge area and dreamy spa inspired bathroom. The stunning bath features a freestanding soaking tub, double vanity, large-format tile, and a beautiful tiled shower with dual shower heads. Three additional bedrooms including a custom-designed bunk room with a beautifully renovated hall full bathroom, while a dedicated laundry space off the upstairs hallway adds everyday convenience. The garage was converted into a recreational space (2026) similar to what could be offered by a "finished basement" with versatility to be additional living room, game room, playroom, gym, or easily converted back to the 2 car garage for covered parking. Notable system updates: insulated and added vapor barrier to crawlspace (2026), installed HVAC in garage (2026), main house HVAC (2020), added mini split in sunroom (2022), hot water heater (2022), full primary bathroom renovation (2026), kitchen updated (2026), main level bathroom (2026), hallway renovation bathroom (2026), refinished/stained hardwood floors (2026), newer pool equipment, painted brick on exterior with special masonry paint (2026), and much more (see full list). Nestled within in close-knit community of Kirwans Landing on Kent Island, you are surrounded by homes on large, manicured lots with a strong sense of pride to the overall appearance of the neighborhood. You are walking distance to the community marina with access to private boat slip in deep water - only $400 a year for a slip! A truly turnkey opportunity. Professionally designed and furnished throughout, the home is ready to enjoy immediately. The seller is willing to negotiate a separate package, including furniture, décor, and housewares, allowing buyers to move in without the time or expense of decorating a home. Living on Kent Island offers a waterfront, relaxed lifestyle with a little more space than other waterfront areas in Maryland.

5 Beds ⋅ 3 Baths

Price Adjustment + Open House Sun Nov 1st 1-3PM!!! Completely reimagined in 2026, this professionally designed Kent Island retreat combines extensively renovated interior with 1.4 private flat acre lot, a saltwater pool, and a 90-foot pier with direct access to Kirwan Creek. Just five minutes from the Bay Bridge, this 5 bedroom, 3 bath home offer the best of Eastern Shore lifestyle. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle boarding, fishing, crabbing, wildlife and sunset watching. Moving inside the 3,000 square foot home, the original intent of the owner was to create coastal inspired retreat for anyone who walked through the front doors. Each space has been re-imagined with professional interior designer style throughout with coastal wallpaper, nautical colors, custom curtains, trim work, updated light fixtures and more. The main level heart of the home you'll find an updated kitchen with new light countertops, ceramic tile backsplash, and fresh hardware with a sweet breakfast table nook. Off the kitchen is a dedicated dining room space with gorgeous wallpaper and updated lighting overlooking the backyard. Step down to the airy main living room centered by electric fireplace and opening to a stunning all window sunroom overlooking your backyard paradise. The main level front room has been converted to functional main level bedroom and the bathroom was updated to a full main level bathroom. Upstairs, the oversized primary suite is designed as a true private retreat, complete with a dedicated lounge area and dreamy spa inspired bathroom. The stunning bath features a freestanding soaking tub, double vanity, large-format tile, and a beautiful tiled shower with dual shower heads. Three additional bedrooms including a custom-designed bunk room with a beautifully renovated hall full bathroom, while a dedicated laundry space off the upstairs hallway adds everyday convenience. The garage was converted into a recreational space (2026) similar to what could be offered by a "finished basement" with versatility to be additional living room, game room, playroom, gym, or easily converted back to the 2 car garage for covered parking. Notable system updates: insulated and added vapor barrier to crawlspace (2026), installed HVAC in garage (2026), main house HVAC (2020), added mini split in sunroom (2022), hot water heater (2022), full primary bathroom renovation (2026), kitchen updated (2026), main level bathroom (2026), hallway renovation bathroom (2026), refinished/stained hardwood floors (2026), newer pool equipment, painted brick on exterior with special masonry paint (2026), and much more (see full list). Nestled within in close-knit community of Kirwans Landing on Kent Island, you are surrounded by homes on large, manicured lots with a strong sense of pride to the overall appearance of the neighborhood. You are walking distance to the community marina with access to private boat slip in deep water - only $400 a year for a slip! A truly turnkey opportunity. Professionally designed and furnished throughout, the home is ready to enjoy immediately. The seller is willing to negotiate a separate package, including furniture, décor, and housewares, allowing buyers to move in without the time or expense of decorating a home. Living on Kent Island offers a waterfront, relaxed lifestyle with a little more space than other waterfront areas in Maryland.

162 Kirwans Landing Ln, Chester

Listing courtesy of Next Step Realty. Contact:

$749,900

NEW PRICE! Reduced! Gorgeous All On One Level Home in Premiere 55+ Community of Four Seasons @ Kent Island * Offering This Lovely Taylor Model w 2/3 Bedrooms + 2.5 Baths and 3rd Car Tandem Garage * Walkable to Clubhouse * Gorgeous Light-Colored Laminated Wood Flooring * Impressive Island w Bar Overhang/Counter Seating + Added Optional Bank of Cabinets w Bonus Counter Space * Pantry * Gas Cooking * Tile Backsplash * Under Cabinet Lighting. This Turn-Key Taylor Model Offers a Comfortable 2014 sf of Living Space with Large Volume Ceilings and Flowing Ever Popular Kitchen-to-Dining-to-Family Room Floor Plan at the Center of the Home. The Bedrooms are Flanked with the 2nd Bedroom with En Suite Full Bath + Walk-In Closet at the Front of the Home and a Rear Facing Primary Bedroom with Tray Ceiling, Triple Windows + Walk-In Closet and En Suite Full Bath with Substantial His 'n Her Vanities and Easy Walk-In Shower. Off the Foyer there is a Versatile Flex Room Accented with Sliding Barn Doors Which Serves Nicely as a Den/Office/Additional Sleeping Area for the Grandkids and Serviced by the Foyer Powder Room Across the Hall. Around the Corner is a Built-In Coat Drop Station and Separate Laundry Room with New Full-Sized Front-Loading Washer and Dryer. The Garage is Spectacular Offering Coveted Additional Parking for a 3rd Car/Golf Cart OR Use it as Additional Storage/Workshop Area. This Home is Propane Gas Heat, Central A/C, Rinnai Tankless Gas Water Heater and Public Water, Public Sewer. At a Mere 1 Year Old, This Home Feels Brand New and Has Been Lightly Lived In and Lovingly Maintained. It Offers an Immediate Move-In Scenario for the Lucky Buyer. Don't Wait for the Builder and Be in by the Holidays! AGENTS: We Are Agent Friendly and We Split Transfer Taxes and Recordation Fees with the Buyer and Offer a Re-Issue Rate on the Title Insurance + Survey to Pass On. The Community of Four Seasons Offers Unparalleled Amenities and a Friendly, Neighborly Environment That All Enjoy and Gather at a 24,000 sf Club House Situated on the Chester River and is Home to a Community Space Where Vibrant Activities are Available to its Vibrant Neighbors and Provides Resort Style Gym, Yoga, Billard's Room, Library, Ballroom and Indoor Pool w Hot Tub + Infinity Outdoor Pool, Cabana, Lounge Areas, Amphitheatre, Fishing Pier, Dog Park, Pickle Ball, Tennis, Bocce Ball + Tot Lot. Homeowners Get Included Grass Cutting, Fertilization + Pesticide Spraying and Lawn Irrigation as a Part of the $315 Monthly HOA Fee Allowing You to Spend More Time Enjoying and Less Time Maintaining! Located 20 Minutes to Historic Downtown Annapolis and to the Regional Anne Arundel Medical Center with an Outpatient Pavilion in Kent Island. It is 30 minutes to Baltimore/Washington International Airport and there are numerous local airport shuttle services offering door to door service making travel easy and stress free for you and your visiting guests. Kent Island Offers a Variety of Wonderful Restaurants Featuring Local Seafood Cuisine + Numerous Marinas and a Freedom Boat Club Location. Four Seasons @ Kent Island is a Wonderful Year-Round or 2nd Home Location for Those Envisioning a Nautically Inspired Lifestyle Combined with a Beautiful, Maintenance Free Home. 168 Redstart Dr is Waiting For You! Call Helpful Lister for More Info.