luxury seaside houses for sale Maryland, United States

Experience Coastal Living in this Beautiful Townhome in the sought after Dune House in North Ocean City. LOW CONDO FEES OF $234 MONTHLY. This spacious 3 Level residence features 3 Bedrooms and 2 Full Bathrooms offering the perfect blend of comfort and sea side charm. Designed for both relaxation and entertaining, the home boasts 3 private decks-ideal for enjoying ocean breezes, morning coffee and gorgeous morning sunrises. The multi level layout provides ample space for family and guests, while large windows invite in natural light and showcase stunning Ocean Views. Located directly along the dunes, this property offers access to a private beach area, creating a peaceful and exclusive coastal retreat. Whether you are looking for a vacation property, investment property or a year round residence, this ocean front townhome delivers the ultimate beach lifestyle. This home has private parking for up to 3 vehicles, including one covered parking space, a private outdoor shower and Low Condo fees of $234 a month. Located within walking distance to Restaurants, Parks and Shops. HVAC and Water Heater were replaced 5 years ago. Brand New Carpet throughout and LVP are being installed the week of 6/1/2026. No Special Assessments. Unit is sold furnished as shown and includes an Ocean Rated Kayak.

NEW PRICE Steps from the Beach – Renovated 3BR Condo with Balcony in North Ocean City! Wake up to the sound of the ocean and enjoy coastal breezes from your private balcony in this beautifully updated 3-bedroom, 2-bath condominium just steps from the beach in sought-after North Ocean City. Located in the Windward Condominiums on 138th Street, this coastal retreat offers the perfect place for personal enjoyment. The renovated kitchen features granite countertops, stainless steel appliances, upgraded cabinetry, stylish pendant lighting, and convenient counter seating—ideal for gathering after a day at the beach. The spacious layout includes three bright bedrooms with generous closet space, including a primary suite with an en-suite bath. A separate laundry room with a full-size washer and dryer adds everyday convenience for owners and guests alike. Additional highlights include plank flooring throughout, abundant natural light, two entrances, and a secure beach locker for storing chairs and gear. The building exterior has been fully renovated with durable HardiePlank siding, upgraded railings, balconies, roof, and steps, offering peace of mind for years to come. Enjoy coastal breezes from the large private balcony and the convenience of off-street parking for two vehicles. Located just a short walk from restaurants, grocery stores, and Northside Park—one of Ocean City's most beloved waterfront parks featuring kayaking, paddle boarding, fishing piers, jogging trails, and the popular 'Sundays in the Park' summer concerts. If you've been waiting for that special North O.C. condo, you've just found it!

**Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

Step into the serenity of this captivating waterfront retreat and elevate your lifestyle to new heights of luxury. Boasting 1,704 square feet of immaculate living space, this three-bedroom, two-bathroom residence presents an unrivaled combination of comfort, elegance, and natural beauty. As you enter, bask in the welcoming ambiance that seamlessly blends with the picturesque surroundings. Engage in an open-air flow between the living, dining, and kitchen areas with the home's carefully designed layout. The heavenly abode is complemented by soaring cathedral ceilings and abundant natural light, creating the ultimate sanctuary for tranquility and warmth. Stunning waterfront views greet you from the four-season room, offering a perfect space to unwind and forget the hustle and bustle of life. Continue feeling cozy throughout the abode- snuggle up by the gas fireplace for ultimate relaxation on cooler evenings. Embrace the true essence of waterfront living with the outdoor waterfront deck which is an idyllic spot for entertainment and allows you to have convenient access to the Saint Martin's River for all of your water activities. Benefit from its elevated position on the lot, ensuring peace of mind as flood insurance is not required. The sellers have previously utilized the shared dock access to house their 18-foot boat, exemplifying the exceptional convenience of this home. And that's not all- it offers you superior access to the renowned Ocean City with its myriad of dining, entertaining, and recreational options. Experience the unparalleled joys of coastal living with this remarkable waterfront home. Don't miss the rare opportunity to make this exquisite property your own. Contact us today to arrange a private viewing and embark on your journey to owning this ultimate waterfront lifestyle.

WATERFRONT NEW CONSTRUCTION - The Ellington” by Greenspring Homes at Water's Edge on Sue Creek This adorable To-Be-Built home is waiting for you to make it your own - pick your favorite colors, finishes, and little details to create your dream space. The layout features 3 bedrooms, 2.5 baths and a bright, open floor plan perfect for relaxing or entertaining. The best part≠ Use your own private dock located in your backyard or walk through the private community gate directly into the marina with waterfront dining and boat slips. ***$25,000 Closing Cost Incentive when you use Greenspring Homes' preferred lender & title company***

Welcome to an extraordinary Southern Living-inspired waterfront bungalow offering a rare blend of tranquility, luxury, and charm in pristine condition. Tucked away on a quiet, secluded road with only three homes, this exceptional property is surrounded by water and bordered by 25 acres of protected, unbuildable land, ensuring lasting privacy and breathtaking natural beauty. Ideally located less than an hour from Annapolis, Baltimore, Washington, D.C., and Northern Virginia-including Alexandria and Arlington-this home provides the perfect balance of peaceful waterfront living with easy access to major metropolitan conveniences. The 4-bedroom residence features 2 full baths and 2 half baths, with an open, airy design that captures stunning water views from virtually every window. The main level includes two bedrooms and showcases soaring cathedral ceilings, solid wood doors, and exceptional craftsmanship, while thoughtfully preserved elements from the original cottage add warmth, character, and a sense of nostalgia. The spacious kitchen is both elegant and functional, offering Silestone countertops, stainless steel appliances, white cabinetry, abundant counter space, a breakfast nook, and radiant heated flooring, with propane gas fueling both cooking and the home's heating system. The inviting family room centers around a striking fireplace and flows effortlessly onto a generous wraparound waterfront porch-perfect for relaxing or entertaining while taking in serene views. Built with quality and durability in mind, the home features a metal roof, Hardiplank exterior, and a warm, welcoming ambiance throughout. This is a true waterfront lifestyle property, where fishing, kayaking, boating, and crabbing are part of everyday life, and where comfort, craftsmanship, and natural beauty come together in perfect harmony.

Welcome to this beautiful five-bedroom, two-and-a-half-bath single-family home in the sought-after Caine Keys II community of Ocean City, Maryland. Perfect for boaters and beach lovers alike, this home features a private boat slip right outside your back door, providing easy access to the water. Enjoy the coastal lifestyle with a large balcony offering scenic views, a cozy gas fireplace, and plenty of parking, Located just minutes from Ocean City's stunning beaches, this home is ideal for year-round living or a relaxing vacation retreat. Don't miss this rare opportunity to own a spacious waterfront home in one of Ocean City's most desirable neighborhoods! Home Extras: Central Vac, Gas stove, 2 large waterfront decks, gas fireplace, and in home stereo speakers ***NEW ROOF April 2026***

Set along a coveted stretch of the Chesapeake Bay, this exceptional waterfront residence offers a rare combination of sweeping panoramic views, a sandy, private community beach, and beautifully curated indoor-outdoor living. From the moment you enter, the home is defined by its connection to the water. Sunlight pours into the main living spaces, where expansive Bay views take center stage and create a serene, ever-changing backdrop. The flow from interior to exterior is seamless. Step directly from the living room onto an expansive deck, ideal for elegant entertaining or quiet mornings by the water. Beyond, a striking dual-level deck extends toward the shoreline, thoughtfully designed to maximize both perspective and privacy. Overlooking the sandy beach below, it offers an elevated setting for gatherings, sunset cocktails, or simply taking in the rhythm of the bay. Inside, the home has been refined with new flooring and lighting, creating a clean, sophisticated aesthetic that complements its natural surroundings. Meaningful upgrades, including a new deep well and a high-efficiency Mitsubishi climate control system, ensure both comfort and peace of mind. An EV charger adds a modern, forward-thinking touch. Whether enjoyed as a full-time residence or a weekend getaway, this home offers a unique opportunity to own a piece of the Bay with exceptional views, direct beach access, and seamless indoor-outdoor living.

Experience waterfront living at its finest in this remarkable St. Michaels retreat, where breathtaking water views define every moment. The beautifully remodeled main level was designed to maximize the scenery, seamlessly blending indoor comfort with the natural beauty beyond. A chef-inspired kitchen with Monogram stainless steel appliances anchors the open-concept living space, perfect for entertaining. Gleaming hardwood floors enhance the home's inviting ambiance. The primary suite is a serene escape with a stunning bath, while the upper level offers generous space ready to be transformed to match your vision. Outside, the property unfolds into a private waterfront playground, complete with a charming cottage ideal for guests or extended family, and a detached two-car garage with a one-bedroom apartment awaiting restoration. Bring your imagination! An exceptional opportunity for boating, entertaining, and relaxed coastal living. Just minutes from fabulous restaurants, boutique shopping, and the quaint charm of St. Michaels.

Seller financing available with favorable terms of 5%. . Located in the heart of downtown Ocean City, Maryland, this spacious 5-bedroom, 3.5-bath single-family home offers the perfect blend of beachside living, commercial potential, and investment opportunity. Just a short walk to the beach, famous Ocean City Boardwalk, Trimper Rides, Jolly Roger Amusement Park, Thrasher's Fries, and countless other attractions, you'll always be in the center of the action. Zoned DMX, this property allows for both residential and commercial use-opening the door to endless possibilities such as a retail space, office, or mixed-use development. Inside, you'll find generous living spaces perfect for family gatherings or hosting guests. The property also offers plenty of parking-a rare find in downtown-and an unfinished lower level that can be transformed into additional living space, a rental unit, or a recreational area, boosting both comfort and value. Whether you're searching for a lucrative investment, a business location, or your full-time coastal residence, this home delivers location, versatility, and potential.