163 houses for sale in Holiday Harbor, District 6 Northern Worcester County Maryland

Welcome to this wellmaintained contemporary home tucked away in the heart of Sherwood Forest in Ocean Pines. This 3BR, 2BA home with a loft comes partially furnished and features numerous upgrades, including a new heat pump, electric hot water heater, newer roof, new siding, and a front deck with an electric awning. Inside, enjoy Corian countertops, new cabinets, tile backsplash, SS apps, plus a beautifully updated bathroom with a walkin shower, vanity & LVP flooring. Outside, youll find an enclosed outdoor shower, paved driveway, and a shed with electricperfect for storage or projects. Make this your next home in Ocean Pines!

Located in the highly sought after community of Montego Bay in North OC, this 3 Bedroom 1-1/2 Bathroom home is being sold fully furnished and ready for you to move right in. Whether you're looking for a full-time residence, a vacation retreat, or an investment property, this one checks all the boxes. Recent upgrades include an insulated metal roof, laminate flooring and shower inserts. Conveniently located within walking distance to the beach, community amenities, shopping, dining, mini-golf, the bus stop, and Ocean City's 58-acre Northside Park. Home of the 4th of July Fireworks! Community amenities include 2 inground swimming pools, 1 kiddie pool, 2 tennis courts, pickle ball courts, a shuffleboard court, a 9 hole mini-golf course, a bayfront boardwalk with 3 fishing/crabbing piers, and an 8 acre wildlife sanctuary that has a pond with a blacktop walking/jogging path. All for a low hoa fee of $415.00 a year!

Waterfront living at its best in ocean pines! Located in desirable Wood Duck Isle I, this impressive waterfront residence offers over 4,000 sq. Ft. of living space, 6 bedrooms, 3 full baths, and over 100 feet of bulkhead with direct access to the Bay. Boaters will appreciate the 55' x 3' dock and 8,000-lb. Boat lift with remote, installed in 2021. With multiple outdoor living spaces, a 3-season room, expansive decks, and a Crows Nest boasting panoramic water views, there is no shortage of places to relax or entertain. Inside, the spacious floor plan offers generous gathering areas, a Gourmet Kitchen, hardwood floors, upgraded carpeting, and abundant storage. The upstairs bonus area features a full wet bar, creating the perfect space for entertaining, game nights, or additional living space. The encapsulated crawlspace with dehumidifier provides added peace of mind. Major updates include the roof (2018), 8,000-lb. Boat lift with remote (2021), EV charger (2024), and downstairs HVAC (202

You wont find anything quite like this in Ocean City. This incredible three story townhome in the highly sought after Bayside Keys community offers an extraordinary combination of space, views, luxury and convenience and NO CONDO FEES! From the moment you enter you will appreciate the private elevator providing effortless access to all three levels. The first level features a three car tandem garage with kitchen cabinets and countertop and refrigerator eliminating the need for the second floor kitchen if you are grilling or entertaining out back. The second floor living area features a wood burning fireplace and opens to an additional glass enclosed sunroom with access to the back by way of outdoor stairs. The updated kitchen features upgraded cabinetry with soft close drawers and custom storage including a pull out shelf designd specifically for your mixer. The home offers three spacious bedrooms and three bathrooms including an extraordinary primary suite with its own fireplace, mult

Waterfront luxury | 73' bulkhead | boat lift | bay access | 2.5-car garage | ocean pines! Experience the best of Eastern Shore waterfront living at 14 Goldeneye Court, an exceptional 4-bedroom, 2.5-bath residence in the desirable Wood Duck I community of Ocean Pines. Set on a generous waterfront lot with 73 feet of bulkhead, a private boat lift, and direct access to the bay, this property is designed for those who appreciate boating, beautiful water views, and an elevated coastal lifestyle. From sunrise over the water to evening gatherings on the expansive outdoor spaces, the setting is truly the centerpiece of this home. Multiple decks, balconies, and gathering areas provide exceptional opportunities to relax, entertain, and enjoy the waterfront. The second-level sun deck offers sweeping water views and an impressive vantage point for taking in the surrounding coastal landscape. Inside, soaring ceilings, abundant natural light, and an open-concept floor plan create a spacious and invi

Nows your time to be part of life in Ocean Pines! Youll love the convenience of one-level living in this updated 3 bedroom 1.5 bath rancher in Sherwood Forest. Relax or entertain in your spacious sun-drenched family room that leads into an eat-in kitchen with updated appliances and enclosed laundry room. From the kitchen, step into the spacious screened-in porch and large partially fenced back yard overlooking trees. Ocean Pines offers an exceptional array of amenities including multiple pools, boat ramps, playgrounds, walking trails, a community center, and much more. All of this is only a few miles from Ocean City where youll find the Ocean Pines beach club with a pool, restaurant, locker rooms and other activities. Ocean Pines isnt just a neighborhood its a vibrant community with something for everyone. If youre looking for an investment, this property has been partially rented generating a steady income

Unique opportunity to complete a permitted Ocean Block two-unit townhouse project! Property is currently at the foundation and partial framing stage, offering a head start for a builder, investor, or owner looking to finish the project. Plans call for two spacious townhouse-style units, each featuring 3 bedrooms and 4 full baths. Unit A: Approximately 1,750 sq. Ft. with 3 bedrooms and 4 full baths. Unit B: Approximately 2,125 sq. Ft. plus an additional approximately 875 sq. Ft. of garage and unfinished area, with 3 bedrooms and 4 full baths. Building permits have already been issued, and water and sewer impact fees have been paid along with 2 electric meters and a 25% down payment on fire sprinkler system, saving valuable time and upfront development costs. Windows and doors are ready for delivery and will convey with the property. An excellent opportunity to take over an existing project and complete two generously sized residences. NO HOA and NO condo fees! Property is being sold in

Nestled under a majestic shady tree, this cozy one-bedroom with great outdoor space is waiting for you. The deck is so inviting you may never go inside. Lounge chairs, gas grill, and room for the Saturday afternoon cookout with friends. Step inside and everything is updated and in its place; gas stove, tiled backsplash, tiled bathroom updated countertops, washer/dryer, and a quiet bedroom with ample closet space. This cozy home has lots of built in nooks and crannies to hold what you need. Come winter, the pellet stove keeps you warm while the NFL plays on the mounted flat-screen tv. A weekend getaway, ready for you to enjoy. White Horse Park has strict rules on occupancy. Primary Residents are not allowed

Nestled in a serene setting, this exquisite traditional home offers a perfect blend of comfort and coastal living, ideal for those seeking a full time home or a perfect beach getaway. With 1,536 square feet of meticulously maintained living space, this residence features three bedrooms and two full bathrooms, designed to accommodate both relaxation and entertaining. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The beautiful and cozy fully insulated four season sunroom is perfect for entertaining and adds extra living space. The combination kitchen and dining space is perfect for gatherings, while the entry-level bedroom provides convenience and accessibility. Elegant flooring choices including, luxurious vinyl plank, ceramic tile and carpet, enhance the warmth and sophistication of the interiors. New Ceiling fans throughout ensure a comfortable atmosphere year-round. The newly replaced roof in 2024, along with a new

Welcome to 25 Royal Oaks Drive, a beautifully updated Ocean Pines home offering the perfect blend of comfort, flexibility, and coastal living. This spacious 4-bedroom, 3-full-bath residence offers 1,728 square feet of thoughtfully designed living space and is situated on a 7,500-square-foot lot. Step inside to find a bright and inviting interior with a versatile layout designed for everyday living and entertaining. The main level features a comfortable living area, well-appointed kitchen and dining space, and a sliding door leading to the rear deckan ideal spot for morning coffee, outdoor dining, or relaxing with friends and family. The upper level offers private bedroom accommodations, including a spacious primary suite, while the lower level provides exceptional flexibility with a large bonus room, full bath, laundry area, and walk-out access to the backyard. Use the lower-level space as a fourth bedroom, guest suite, home office, recreation room, or second living areathe possibiliti

White Horse Park boasts and ideal waterfront location just minutes from Ocean City, with the resort areas most affordable vacation and investment properties! This hard-to-find 3 bedroom double loft home comes fully furnished with new LVP flooring, vaulted ceilings, eat-in kitchen with newer appliances, concrete patio, and brand new HVAC. The sleep sofa adds even more space for overnight guests! A skylight brightens the bathroom that features a full sized tub shower and large linen closet. Youll find lots of storage in the spacious shed, and parking for three vehicles. The convenient location allows for privacy in the rear, and just a short walk to the well kept amenities of White Horse Park, where you own the land, and never pay ground rent! Includes a secured gate entry, large swimming pool, marina, boat ramp, crabbing pier, fenced boat storage, picnic area, playground, bath houses and laundry areas. The low HOA fee includes water/sewer, lawn maintenance, trash removal, and much more.

Bring your boat, your beach chairs, and start enjoying the Ocean City lifestyle! Welcome to 103 Channel Buoy Road in Caine Keys II, a very clean and well-maintained four-bedroom, three-bath waterfront home offering the perfect combination of boating convenience and easy access to the beach. Enjoy your own private dock, updated fiberglass bulkheading, and beautiful waterfront settingideal for relaxing, fishing, or heading out on the water. The home also features an updated roof and has been lovingly maintained, making it easy to move in and start enjoying. Located close to Ocean Citys beautiful beaches and the Atlantic Ocean, this property gives you the opportunity to enjoy waterfront living without giving up the convenience of being near everything Ocean City has to offer

Enjoy waterfront living in this inviting 3-bedroom, 3-bath canal-front home located just a short distance from the open bay. Designed to make the most of its waterfront setting, the home features a spacious screened porch, upper-level deck, and patio with built-in seating, providing multiple places to relax, entertain, and enjoy the views. Inside, the kitchen offers tile flooring and pantry storage and opens to the dining area for easy everyday living. The upper level features a bedroom, full bath, and versatile loft space. Additional highlights include a newer roof installed in 2017, HVAC system replaced in 2018, water heater installed in 2024, and partial furnishings included. Whether you are searching for a primary residence or waterfront getaway, this home offers comfort, flexibility, and an ideal coastal lifestyle

This well maintained home on a quiet cul de sac in the south gate of Ocean Pines features an open floor plan. The main level is bright with cathedral ceilings in the living room, a dining area off of the large kitchen with updated appliances and a 2nd sitting area, a first floor primary suite with high ceilings and walk in closet. You will also find on the first floor a laundry room with utility sink, a half bath, access to the attached garage with bonus storage area and a large 4 seasons room with a gas fireplace that leads to the back deck. The second level features 2 additional bedrooms, a full bathroom and a small bonus room along with storage area. Roof and skylight were replaced in 2022

Your beach retreat awaits. Few of this cottage type come available. Move in ready, getaway for family & friends. Come own your piece of the Eastern Shore beach retreat w/in approx. 10 miles to Ocean City beach, boardwalk, shopping, restaurants, casino, horse races, Assateague Natl. Park & beach & see the ponies, all that OC & west O. C. offer & much more. Own deeded lot & home, no ground rent. 24 hr. Security gated, 465 private homes, waterfront amenity rich beach resort environment, located on St. Martin's River leading to open bay. Bay & large windows brighten. Check out the beautiful window shades. Comfortable, soothing feeling as you enter this elegantly fully furnished turn key, 1 story-2 BR cottage style, open living area w/cathedral ceiling ranch home. Bath w/tub & shower. Deep linen closet. New toilet 2025. Full size washer/dryer, 6-2021. Kit. has lg. breakfast island, built in micro, gas range, oven & fridge. Stainless sink w/new Moen faucet 7-2026, elec. 40 gal. W/htr. 2015.

Welcome to this beautifully updated 3-bedroom, 2-bath home in desirable Ocean Pines, Marylandapproximately 9.2 miles from Ocean City! The inviting floor plan features a convenient main-level bedroom and numerous recent improvements, including new kitchen cabinets and countertops, seven new windows, nine new doors, and 9 trees removal that created a more open and spacious setting. The crawl space has also been improved with select joist replacements and the installation of a new vapor barrier. Enjoy the many amenities Ocean Pines has to offer, including indoor and outdoor pools, the Yacht Club, parks, recreational facilities, and moreall just a short drive from Ocean Citys beaches, dining, and entertainment. Dont miss this opportunityschedule your private showing today!

This charming property in Ocean Pines, MD features 3 bedrooms and 2 bathrooms, offering comfortable living in a peaceful setting

Discover the perfect Eastern Shore retreat just minutes from Ocean City. Located in the gated community of White Horse Park I, this beautifully renovated home offers 2 bedrooms, 2 updated baths, and a versatile bonus room ideal for guests or a home office. Inside, enjoy a stunning new kitchen featuring quartz countertops, white shaker cabinetry, and stainless steel appliances. Stylish upgrades continue throughout with new flooring, custom tile baths, generous storage, and a private shed. Recent roof repairs provide added peace of mind. The low $185/month HOA fee includes water, sewer, trash, security, and access to resort-style amenities including a clubhouse, pavilion, boat ramp, basketball court, playground, kayak storage, picnic areas, and bath houses. Marina boat slips and storage are also available. Open year-round, this property offers excellent flexibility for personal use or short-term rental potential. Conveniently located near the Ocean City Boardwalk, Assateague Island Natio

Set on a premier golf course lot overlooking the 8th fairway, this exceptional, nearly 3,900-square-foot home offers 4 bedrooms, 3 full baths of quality construction, thoughtful design, and extensive upgrades. Nine-foot ceilings, four skylights, cathedral ceilings in both the living room and the sunroom, numerous pocket doors, and abundant natural light create an inviting feel throughout. The main level features a spacious primary suite with en-suite bath, bamboo hardwood flooring, and a living room highlighted by a dramatic two-story natural stone fireplace matching the home's exterior stonework. The fireplace features an old-wood mantel reclaimed from a Pennsylvania barn, gas insert with heat blower, remote operation, and annual maintenance. Plantation shutters adorn the upper-level windows in the living room. Most lighting throughout the home is on dimmers, and all TVs are wall-mounted with wiring concealed. The beautifully appointed kitchen features tall-to-ceiling Omega cabinetry

This new construction property is a customized version of the popular Wahoo model, with groundbreaking scheduled to start in approximately 30 days. Buyers who secure this home early have a rare window of opportunity to select the custom interior finishes and make this home uniquely theirs. Core Property Overview, Floor Plan: Customized Wahoo/3 Model, Bedrooms: 3 spacious bedrooms, Bathrooms: 2 full bathrooms, Garage: Attached 2-car garage, Premium Interior & Gourmet Kitchen Custom Upscale Kitchen: Outfitted with high-end stainless steel appliances. Gas Cooking: Features a premium gas range for culinary precision. Gas Fireplace: Serves as a cozy, ambient centerpiece in the main living area. Primary Suite: Features an expansive, large primary bath with detailed custom showers. Outdoor Living Spaces Screened Porch: Built for bug-free relaxation and comfortable outdoor lounging. Outside Deck: Perfect for grilling, entertaining, and enjoying the backyard views. High-Efficiency & Structural

Buyers failed to sell their home. Tucked along the canal in the sought after community of Ocean Pines, this charming A-frame retreat blends rustic cottage character with the laid back waterfront lifestyle youve been dreaming of. With soaring vaulted ceilings, oversized windows, and an open layout designed to capture natural light and tranquil water views, this home is ready for relaxing weekends, family gatherings and entertaining after a day on the water. Step outside to enjoy the expansive wraparound deck overlooking the canal, the perfect place for morning coffee or evening sunsets. Boaters will appreciate the shared dock with a dedicated private slip for the home, offering easy access to the water. A cozy fireplace adds warmth and charm to the inviting living space, while the garage provides additional storage for all your beach and boating essentials. The main level features two bedrooms, a full bathroom, and a convenient laundry closet. Upstairs, the loft overlooks both the water

We're going to call this canal-front because technically, that's what it is. Just don't expect it to look like most canal-front homes in Ocean Pines! Walk out back and you'll understand the difference. Instead of staring across a narrow canal at another row of homes, the water (and views) open up considerably. With no homes blocking your view, you're given a stunning view of the Ocean Pines Golf Course, and beyond. Plus, you get the boating access you're looking for in a waterfront home. Let's move on to the house itself. At approximately 2,500 square feet, this 3-bedroom, 3-full-bath home gives you something else that's surprisingly difficult to find on the waterfront in Ocean Pines: SPACE. There's a true two-car garage, generous living areas, a three-season room overlooking the water, and a large first-floor deck that turns the backyard into a pretty compelling reason to spend more time outside. Plus, the interior has been extensively renovated with a new kitchen, new bathrooms, new

Just like new! And a price reduction. Adorable and affordable! Built by American Homes, this charming, well-maintained 3-bedroom, 2-bath rancher is ideally located near the Swim & Racquet Club pool and White Horse Park. The bright, open floor plan features cathedral ceilings, a combined Living, kitchen and dining area, and a separate laundry room off the kitchen. Relax on the inviting front porch or enjoy the spacious rear deck. Recent updates include fresh paint, roof replacement with warranty (2019), newer HVAC, newer washer and dryer, and refrigerator, new microwave stove and dishwasher. Newly LVP flooring in the living room, dining room, and kitchen, new carpet in bedrooms. New bathroom flooring and raised toilets. Encapsulated crawlspace. Enjoy this low-maintenance home near the White Horse park, pool and recreation center

Quality Craftsmanship meets exceptional care in this beautifully maintained home, built by Piney Island Builders. Neatly nestled on a large private lot backing to peaceful woods in the heart of Ocean Pines, this home offers the perfect blend of comfort, privacy, and timeless appeal. Designed for easy living, the home features a spacious first-floor primary suite, providing convenience and flexibility for everyday life. Recent updates include a newer roof, composite decking, and updated kitchen appliances, allowing you to move in with confidence. Step outside and enjoy the beautifully landscaped Backyard, where you'll find a charming treehouse and plenty of space to relax, entertain, or simply take in the serene wooded setting. Recently updated crawl space encapsulation and dehumidifier ensure peace of mind. A large garage offers ample room for vehicles, storage, and hobbies. Two more outbuildings, a large shed, and an adorable greenhouse complete the yard. This exceptional home showcas

Brand new construction now! This impressive home offers over 3,400 square feet of living space with 5 bedrooms, 3.5 baths, and a bonus room, providing exceptional flexibility for todays lifestyle. Located on a quiet cul-de-sac in Triple Crown Estates, a community known for its larger lot sizes, this property features a generous 125 x 100 homesite. The home offers two primary suitesone on each level. The first-floor primary suite features a beautifully tiled shower, while all full bathrooms are equipped with double-bowl vanities. The stunning kitchen showcases quartz countertops and stainless steel appliances and flows seamlessly into the dining area, which opens to a screened porch and deck, perfect for indoor-outdoor living. The family room is warm and inviting with a linear electric fireplace and a beam-accented vaulted ceiling. Additional highlights include 9 ceilings on the first floor, LVP flooring throughout the first floor and staircase, a dedicated laundry room, an 80-gallon ho

Welcome to the storied community Isle of Wight in West Ocean City. Rare waterfront find! Over 90 feet of newly bulkheaded waterfront. PANAORAMIC views of Assawoman Bay and Ocean City. This 5 bedroom, three bath home is situated on over a half acre of land with a deep water canal, minutes from the Ocean City Inlet. New bulkhead was installed in 2025, has a separate THREE CAR GARAGE. Solid architectural stone contstruction, this home boasts Central Air and heat, lovely circular driveway provides and abundance of off street parking on a dead end street with minimal traffic. Enter up the sold stone steps through the front door opens up to a full dining rooml area for entertaining, SPACIOUS living room area, down the hallway to a full sized WASHER/DRYER room and two bedrooms and full bath on level one. Hardwood floors and Tile throughout. Sprawling kitchen with gourmet GAS fired stove and fully equipped with modern appliances. Off the kitchen is a cozy room facing a private deck off the fir

BIGGER, BETTER BUT you better hurry if you want to pick your own colors! Photos are actually pictures of 83 King Richard the beautiful HUNTER I model that just sold in 06/26! The Hunter I model is the little brother of The Hunter II currently being built at 5 Jockey Court with a larger footprint and on a larger lot (see house plans). Crafted by Ultimate Homes, LLC, this masterfully designed 4-bedroom, 2.5-bath with den/office all in this sprawling rancher located in the prestigious new section of Triple Crown Estates in Ocean Pines. Blending timeless craftsmanship with refined modern finishes, this residence offers an elevated lifestyle just moments from the coast. Inspired Design. Exceptional Comfort, From the moment you arrive, the homes commanding presence and architectural detail set the tone for what lies within. Built with 2x6 construction and topped with 40-year architectural shingles, the quality is evident at every turn. Inside, an expansive open-concept layout creates seamles

OC Waterfront Living! This 2 bedroom, 1.5 bathroom bayside townhome features a reverse layout with the bedrooms on the first floor and a walkout to your private patio oasis complete with boat slip/dock. The coastal style jack-n-jill bedrooms are conveniently joined by a full bathroom. Venture upstairs and you are greeted by a large family room with vaulted ceilings, a fully equipped kitchen with stainless steel appliances and a half bath. The top floor is thoughtfully designed and maximizes space and natural light. Walk outside on the oversized upstairs deck to find the amazing canal and OC skyline views. With your private access to the bay, all you have to do is bring your boat, kayak or paddle board and head on out for an amazing day. This unit provides a perfect setting for fishing enthusiasts and water lovers alike. Whether you're looking for a turnkey investment property, a weekend getaway, or a full-time residence, this property has it all!

Escape to your own private retreat on 5.41 acres while enjoying the convenience of being just minutes from restaurants, shopping and the beach. Tucked away from the road, this custom-built 5-bedroom, 3.5-bath home features an open floor plan with 10-foot ceilings, hardwood flooring throughout the main living areas, and a living room with a gas fireplace. The chef's kitchen is equipped with a Monogram gas range, pot filler, pantry, abundant cabinetry, and a breakfast area, while the formal dining room and bright three-season room provide additional gathering spaces. The privately situated primary suite offers a peaceful retreat with a spacious ensuite bath and walk-in closet. Two additional bedrooms, a full bath, and a half bath complete the main level, while the upper level provides two more bedrooms and another full bath, ideal for guests or multigenerational living. Outside, enjoy the tranquil setting with a decorative stone pond and mature landscaping. The impressive 40' x 60' metal

Enjoy easy one-level living in this charming 2-bedroom, 2-bath rancher located in the sought-after community of Ocean Pines. The functional floor plan offers comfortable living spaces, abundant natural light, and low-maintenance livingperfect as a primary residence, vacation getaway, or investment property. Large deck with storage shed attached. Ocean Pines residents enjoy an exceptional lifestyle with outstanding amenities, including indoor and outdoor swimming pools, tennis courts, scenic walking and biking paths, a dog park, community center, playgrounds, parks, and year-round activities. Conveniently located just minutes from Ocean City beaches, shopping, dining, golf, and marinas, this home offers the perfect blend of comfort, recreation, and coastal living