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101 Jarman Branch Dr, Centreville
$400,000
4 Beds ⋅ 2 Baths
Single-level living with cathedral ceilings, and a 1-acre corner lot surrounded by nature. Life slows down in the best way at this 4-bedroom, 2-bath rambler set on a spacious 1-acre corner lot in the quiet countryside of Ruthsburg. Open fields, towering evergreens, and wide green lawns create a peaceful, laid-back setting. The home is functional and livable as is, while leaving room for you to declutter, update, and truly make it your own. Inside, cathedral ceilings lift the living and family room area, giving the space an open, airy feel with plenty of room to gather. It's the kind of place where you can breathe easy and enjoy the view from your own front porch. The kitchen is generously sized with abundant cabinetry, ample counter space, and a breakfast bar. All 4 bedrooms are on one level, giving you flexibility for guests, a home office, or a hobby room. Two full baths keep daily routines running smoothly. There’s also the attic for extra storage space. Outdoors, your acre of yard gives you room to garden, play, or simply relax. You're located on Ruthsburg Road (Route 304) near Mason Branch Road, with Route 481 just down the road for easy connections to nearby towns and main routes. Local farms like Wagner Farm dot the landscape, and you'll be surrounded by the quiet charm of rural Queen Anne's County. With space, privacy, and potential in a peaceful country setting, this home is ready for your vision. Schedule your showing today and picture the possibilities!

101 Jarman Branch Dr, Centreville

Listing courtesy of EXP Realty, LLC. Contact:

211 Pathfinder Cir, Grasonville
$550,000
3 Beds ⋅ 2 Baths
Better than new and built in 2025, this beautifully appointed home sits on a quiet premium lot backing to woods and the community pond. Offering nearly 2,000 square feet of living space, three bedrooms, and two full baths, it pairs modern finishes with a peaceful setting. The kitchen features an expansive island, quartz countertops, subway tile backsplash, stainless steel appliances, and a walk-in pantry, with plenty of room for everyday meals and entertaining. Luxury vinyl plank flooring flows throughout the main living spaces. The primary suite offers a tray ceiling, walk-in closet, and spacious en suite bath with a double vanity and walk-in shower. A dedicated laundry room with a high-efficiency washer and dryer and a spacious garage add everyday convenience. Outside, the fully fenced backyard thoughtfully combines vinyl fencing along the sides for privacy with aluminum fencing across the rear to preserve the wooded and pond views. Located in a community across from the Chesapeake Bay Environmental Center, this move-in-ready home offers a beautiful place to settle in and enjoy life on the Shore.

211 Pathfinder Cir, Grasonville

Listing courtesy of Samson Properties. Contact:

153 White Tail Ct, Centreville
$725,000
5 Beds ⋅ 3 Baths
Welcome home to this sanctuary that beautifully blends modern comfort with warm Eastern Shore charm. Nestled at the end of a quiet cul-de-sac in the desirable Willow Branch East community, this property offers a sprawling 1.61-acre lot with * 5 BEDROOMS * A welcoming front porch leads into a dramatic two-story open foyer featuring an elegant staircase. The main level boasts a bright, flexible formal dining room or home office and a spacious living room. At the heart of the home is a spacious kitchen fully equipped with Silestone countertops, 42" Maple Toffee cabinetry, and brand-new stainless steel appliances, plus a generous keeping room perfect for large gatherings. Transition effortlessly through the cozy family/sunroom—complete with a stylish barn door—to the rear stone paver patio for seamless indoor-outdoor entertaining. Upstairs, the private primary suite serves as a true sanctuary, showcasing a spacious sitting room and a spa-like en-suite bath with a jetted soaking tub. Four additional bedrooms and a full hall bath provide ample space for family and guests. Premium Andersen windows flood the home with natural light, while upgrades like a Rinnai tankless water heater, reverse osmosis, a water softener, and recent two-zone heat pumps (2023 & 2025) ensure modern comfort. Bonus feature: Light up the neighborhood effortlessly with a built-in, interior holiday light switch wired directly to the front elevation!! Located just minutes from historic Centreville, enjoy peaceful, private living with convenient commuter access to Route 301, Annapolis, Easton, and the Chesapeake Bay Bridge.

153 White Tail Ct, Centreville

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

515 Baxter Rd, Sudlersville
$465,000
3 Beds ⋅ 2 Baths
Welcome home to this 3-bedroom, 2-bath home situated on .75 acres along a peaceful road backing to mature trees and farmland. Inside, you'll find an inviting open kitchen and living area featuring a charming brick wood-burning fireplace, creating a warm and comfortable gathering space. Step outside to the oversized back deck, perfect for entertaining, relaxing, or enjoying the private country setting. The backyard is ready for summer with a fenced 18' x 36' in-ground saltwater pool, offering plenty of space for outdoor fun and gatherings. Adding even more versatility to the property is the 30' x 40' detached garage, approximately five years old, complete with a half bath and 220V electrical service for electric vehicle charging—ideal for vehicles, hobbies, a workshop, or additional storage. Recent updates include a new heat pump in 2026, new furnace in 2025 and roof 5 years old. With plenty of outdoor space, a pool, an impressive detached garage, and peaceful views, this property offers a great combination of comfort, functionality, and country living.

515 Baxter Rd, Sudlersville

Listing courtesy of Benson & Mangold, LLC. Contact:

830 Warbler Way Unit 2843, Chester
$779,990
2 Beds ⋅ 3 Baths
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:

111 Marshgrass Way Unit 43, Chester
$744,900
2 Beds ⋅ 3 Baths
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 glass cabinetry. 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:

129 Anna Carol Dr, Stevensville
$650,000
4 Beds ⋅ 3 Baths
Coastal charm, exceptional living spaces, and a coveted main-level primary suite come together beautifully in this standout Ellendale at Kent Island home. Mature landscaping and an expansive covered front porch create an inviting first impression, while inside, hardwood floors, crown molding, chair rail, and thoughtful architectural details give the home warmth and character from the moment you enter. At the heart of the home, the kitchen and family room form a spacious, open gathering area designed for both everyday living and entertaining. The beautifully appointed kitchen features granite countertops, stainless steel appliances, gas cooking, recessed lighting, and pendant lighting above a generous center island with breakfast bar seating. Open to the kitchen, the family room is enhanced by a soaring cathedral ceiling and offers plenty of space to gather, while direct access to the screened porch extends the living area outdoors, creating an easy flow for entertaining. A separate open dining area provides a dedicated setting for meals and gatherings, while a phenomenal butler’s pantry is equally accessible from both the dining area and kitchen. More than simply additional storage, this thoughtfully designed space features granite countertops, a wine refrigerator, and a double-door pantry, allowing it to function beautifully as a beverage station, serving area, additional prep space, and pantry, all while providing a natural connection between the kitchen and dining area. Privately positioned away from the main gathering spaces, the main-level primary suite offers an inviting retreat with an oversized walk-in closet and a spacious en suite bath featuring dual vanities and a tiled walk-in shower. A powder room and conveniently located laundry room complete the main level. Upstairs, an exceptionally spacious open landing overlooks the family room and leads to three bright bedrooms and a well-appointed full hall bath with ceramic tile flooring and a tiled shower. One bedroom connects to a separate finished sitting room or study, creating an especially versatile suite with space for a private office, reading room or hobby space. Large windows fill the upper level with natural light, while charming coved ceilings and wide baseboard molding add another layer of architectural character. Storage is another standout feature. An interior staircase provides convenient walk-down access to an expansive, storage area beneath the home, offering an unusually generous place for seasonal décor and household items. At the rear, an alley leads to the driveway and two-car garage, discreetly positioning parking away from the front of the home and preserving its charming streetscape. Adding to the home’s everyday efficiency, the solar panels are owned outright, providing the opportunity for substantial savings on electricity with no solar lease to assume. Ellendale at Kent Island completes the package with a clubhouse, community pool, tot lot, and recreational amenities in a setting that combines the relaxed character of Maryland’s Eastern Shore with exceptional accessibility. Located approximately one mile from the Chesapeake Bay Bridge, the community is convenient to historic Stevensville, Kent Narrows, Terrapin Nature Park, and public water access at Thompson Creek. Boating, waterfront dining, walking and biking trails, and the natural beauty of Kent Island are close at hand, while Annapolis and destinations throughout the greater Washington-Baltimore region remain within easy reach—a remarkable combination of coastal living and everyday convenience.

129 Anna Carol Dr, Stevensville

Listing courtesy of Northrop Realty. Contact:

325 Rings End Rd, Millington
$589,000
5 Beds ⋅ 3 Baths
Discover an exceptional investment opportunity with this stunning Colonial-style residence operating as a guest favorite on Airbnb. Perfectly positioned just 16 feet from the serene Chester River. Step inside to find an inviting open floor plan that seamlessly connects the family room to the kitchen, creating a warm and welcoming atmosphere. The home is adorned with built-ins and window treatments that enhance its charm, while the cozy carpet and wood floors add a touch of elegance throughout. The property features two fireplaces, providing a cozy ambiance during cooler months, and an attic for additional storage or potential expansion. The upper-floor laundry adds convenience, making this home not only beautiful but functional as well. Outside, the allure continues with a personal in-ground pool, perfect for relaxation and recreation. The expansive 1.43-acre lot offers ample space for outdoor activities, while the breathtaking water views create a tranquil backdrop for your daily life. With water access just steps away, you can enjoy kayaking, fishing, or simply soaking in the natural beauty of the Chester River. From an investment perspective, this property stands out with its excellent condition and desirable features. The combination of spacious living areas, modern amenities, and proximity to water activities makes it highly attractive for potential renters or future buyers. The growing demand for waterfront properties ensures that your investment will appreciate over time, providing both immediate enjoyment and long-term financial benefits. This residence is not just a home; it's a lifestyle choice that offers the perfect blend of comfort, luxury, and investment potential. Don't miss your chance to own a piece of paradise that promises both personal enjoyment and financial growth. Seize this opportunity today!

325 Rings End Rd, Millington

Listing courtesy of Hostetter Realty. Contact:

510 Talbot Rd, Stevensville
$575,000
3 Beds ⋅ 3 Baths
BRAND NEW HOME! QUICK DELIVERY! Inventory Sale on this finished home!!! Located just across the street from the picturesque Shipping Creek, this brand new home offers an amazing opportunity to embrace a water-oriented lifestyle. The views of the bay and creek create a serene environment, perfect for nature lovers and those seeking a peaceful retreat. With a brand new home, you'll have plenty of time to enjoy the water! Walk to the waterfront park just down the street! This exquisite new construction home embodies the perfect blend of luxury and comfort. With a stunning Craftsman architectural style, this residence offers a warm and inviting atmosphere. Step inside to discover a thoughtfully designed open floor plan that seamlessly connects the living, dining, and kitchen areas. The large gourmet kitchen is a chef's dream, featuring upgraded quartz countertops, a spacious island, and stainless-steel appliances, including a sleek oven/range with hood and French door refrigerator with water and ice dispenser. There is abundant cabinet and counter space here, this kitchen is sure to meet your every need. Upstairs this home boasts three generously sized bedrooms, including a primary suite complete with a luxurious bathroom featuring a large double vanity and tiled stall shower ensuring a spa-like experience at home. The primary suite features a huge walk in closet complete with wire shelving. The Primary suite looks out over Eastern Bay and Shipping Creek, a vista that is sure to instill relaxation and peace. Each bedroom is designed with comfort in mind, offering ample closet spaces that provide both functionality and style. Bedroom floors are carpeted for comfort, and ceiling fans ensure temperature control. The upper-level hall bath is also equipped with a large double vanity for convenience and a generous tub shower combination. The main interior is adorned with luxury vinyl plank flooring and wainscoted walls, enhancing the home's aesthetic while ensuring durability. The upper floor laundry adds convenience to your daily routine, making chores a breeze. Outside, the property is graced with a level water oriented front yard and a level lot that backs to trees, providing a tranquil backdrop for outdoor gatherings. Enjoy the fresh air on the expansive deck, perfect for entertaining or simply unwinding after a long day. The paved driveway leads to an attached garage, offering both convenience and security. Kent Island Estates is a suburban haven, providing easy access to local amenities while maintaining a sense of privacy and tranquility. This property is not just a home; it's a lifestyle choice that promises comfort, elegance, and a connection to nature. Experience the luxury of new construction and the joy of creating lasting memories in this exceptional residence.

510 Talbot Rd, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

101 Chestnut Rd, Stevensville
$455,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained and thoughtfully designed home, ideally situated on a desirable corner lot with a fully fenced backyard. Offering an excellent combination of comfort, functionality, and style, this property is an ideal opportunity for a first-time buyer, growing family, or anyone looking for a move-in-ready home. Step inside and you’ll immediately appreciate the inviting traditional floor plan, enhanced by beautiful new wood flooring, recessed lighting, upgraded countertops, and an abundance of natural light. The spacious family room flows seamlessly from the kitchen, creating a comfortable and welcoming space for everyday living and entertaining. The well-appointed kitchen offers an abundance of workspace and storage, featuring a center island, pantry, eat-in area, table space, upgraded countertops, built-in microwave, built-in range, self-cleaning oven, dishwasher, and exhaust fan. Whether you’re preparing a quick breakfast or hosting family and friends, this kitchen provides the convenience and functionality today’s homeowners desire. The home offers two full bathrooms, including one with a convenient walk-in shower. Generously sized bedrooms provide comfortable living spaces, while walk-in closets offer excellent storage. Ceiling fans and window treatments throughout the home add comfort and convenience. The main-level laundry area makes everyday living simple and efficient, with a washer and electric dryer included. Additional features include storm doors, double-hung windows, an electric alarm system, an owned water-conditioning system, a water-treatment system, and a water heater. The crawl space has also received important improvements. All cavities and walls have been fully insulated and sealed, and a dedicated dehumidifier system has been installed to help maintain a cleaner, drier, and more controlled environment beneath the home. Outside, the spacious corner-lot setting and fully fenced backyard provide plenty of room for outdoor enjoyment, entertaining, gardening, play, or simply relaxing. The backyard offers the privacy, flexibility, and functionality many buyers are looking for, making it an ideal space for families and outdoor activities. With its comfortable living spaces, practical upgrades, excellent storage, and inviting outdoor setting, this home offers an exceptional opportunity to establish roots and enjoy years of comfortable living. Whether you’re purchasing your first home, looking for additional space for your family, or simply searching for a well-maintained property in a desirable setting, this home is one you won’t want to miss.

101 Chestnut Rd, Stevensville

Listing courtesy of EXP Realty, LLC. Contact:

205 Dominion Ln, Chester
$300,000
3 Beds ⋅ 2 Baths
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:

34 Queen Anne Way Unit A, Chester
$570,000
2 Beds ⋅ 2 Baths
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:

347 Claiborne Dr, Centreville
$549,900
3 Beds ⋅ 3 Baths
Welcome to 347 Claiborne Fields Drive, situated on an impressive 1.26 acre lot in the sought-after Claiborne Fields community of Centreville! With over 2,000 square feet of living space, this 3 bedroom, 2.5 bath home has been well maintained and cared for by the original owner for many years. Fresh paint and new carpet throughout give the home a clean, refreshed feel, making it ready for its next chapter. An attached two car garage provides added convenience and plenty of space for parking and storage. Enjoy plenty of room to spread out both inside and out, with a spacious lot backing to woods for added privacy and a peaceful setting. Located in an established community with convenient access to Centreville and Route 301, this home offers a wonderful combination of space, privacy, and location. Come see all that 347 Claiborne Fields Drive has to offer!

347 Claiborne Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact:

117 Harrier Way, Chester
$790,000
3 Beds ⋅ 2 Baths
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:

168 Redstart Dr, Chester
$749,900
2 Beds ⋅ 3 Baths
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.

168 Redstart Dr, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

225 Autumn Ln, Centreville
$499,000
4 Beds ⋅ 3 Baths
Welcome to this lovely 4-bedroom, 2.5-bath home tucked away on a quiet cul-de-sac in the private community of Heritage, right in the heart of Centreville! Inside, you’ll find beautiful hardwood floors throughout much of the main living area, along with carpeting that is only 1 year old. The spacious kitchen offers plenty of room to gather, featuring a large island and gas cooking, while the adjoining living room provides a cozy gas fireplace for relaxing on chilly evenings. A separate family room offers additional living space, as well as a separate dining room for larger gatherings. The convenient upper-level laundry is located right outside the bedrooms, all of which are very spacious. The primary bedroom features an updated shower. Recent improvements include a new water heater approximately 1 year old, a new backyard fence, and an HVAC compressor believed to be approximately 5 years old. Step outside to enjoy the large covered front porch, or relax in the Sunroom/3 Season Room with skylights, overlooking a private backyard that backs to protected trees. Seasonal winter views of the stream beyond the backyard add to the peaceful setting and natural backdrop. Ideally located close to Centreville’s schools, dining, shopping, parks and the Wharf, with easy access to major commuting routes, this home offers comfortable living in a convenient Centreville location.

225 Autumn Ln, Centreville

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

206 Melvin Ave, Grasonville
$464,900
3 Beds ⋅ 3 Baths
Welcome home to this beautifully maintained and fully updated 3-bedroom home, just 8 years young! Featuring like-new systems and roof, this home offers modern comfort and peace of mind. A 4-foot bump-out provides additional living space, while the upgraded kitchen boasts stainless steel appliances and sliding glass doors leading to a spacious 12x20 composite deck—perfect for entertaining. Enjoy outdoor living with an above-ground pool, fully fenced backyard with white vinyl privacy fencing, and a crushed stone patio that leads to a cozy fire pit area. The long gravel driveway and oversized two-car garage offer ample parking and storage. Inside, you’ll find a spacious primary bedroom with a private full bath, plus an additional family room on the lower level with a convenient half bath—ideal for extra living space, guests, or a home office. Perfectly maintained from the front door throughout, this hidden gem is conveniently located near Route 50, making it an excellent choice for commuters. Stairs have recently been painted pictures will be updated soon .No HOA!

206 Melvin Ave, Grasonville

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

105 E Brook Dr, Centreville
$549,000
4 Beds ⋅ 4 Baths
Welcome to 105 E Brook Drive, located in the sought-after North Brook community of Centreville, MD! Situated on an oversized corner lot with plenty of room to expand, this beautifully refreshed home offers 4 bedrooms, 3.5 bathrooms, and the space and flexibility today's buyers are looking for! Step inside to discover gorgeous refinished hardwood floors, fresh paint throughout, and new carpeting (2026), creating a bright and inviting atmosphere. The kitchen features brand-new appliances (2026), while a new tankless water heater (2026) adds modern efficiency and convenience. Upstairs, the spacious primary suite offers a relaxing retreat, complete with two closets and a private bathroom featuring tile floors, a soaking tub, and a separate stand-up shower. The fully finished basement provides incredible additional living space, perfect for a recreation room, home office, entertaining, or hosting guests. Outside, enjoy the patio overlooking the expansive backyard, offering endless possibilities for outdoor entertaining, play, or future improvements. Beyond the home, the North Brook lifestyle is just as inviting! Enjoy a community designed for outdoor living and connection, featuring scenic walking paths, peaceful ponds, a community pavilion, playground, and soccer field. Whether you're enjoying an evening stroll, spending time outdoors, or gathering with neighbors, North Brook offers the perfect blend of neighborhood charm and everyday convenience. With thoughtful updates, generous living space, an exceptional corner lot, and a community you'll love coming home to, 105 E Brook Drive offers more than just a home, it's a lifestyle! Don't miss your opportunity to make it yours!

105 E Brook Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact:

231 Dominion Rd, Chester
$599,000
Unique opportunity to own a versatile three-unit property situated on approximately one-half acre in Chester. The property features a main residence with 2 bedrooms, 1 full bathroom, and a full basement, offering comfortable living space for an owner-occupant or tenant. A separate building on the property includes two additional rental units: a ground-level 1-bedroom efficiency apartment and an upper-level unit with 2 bedrooms and 1 full bathroom. This setup provides excellent income-producing potential while maintaining privacy between residences. Conveniently located near shopping, dining, and everyday amenities, this property is ideal for investors or buyers seeking a live-in rental opportunity with multiple income streams.

231 Dominion Rd, Chester

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

231 Dominion Rd, Chester
$599,000
5 Beds ⋅ 3 Baths
A rare opportunity to own a property that combines comfortable living with income-producing potential. The primary residence features 2 bedrooms, 1 full bathroom, and a full basement, offering ample storage and living space. Behind the main home is a separate building with two additional rental units. The lower-level unit is a cozy 1-bedroom efficiency apartment, while the upper-level unit offers 2 bedrooms and 1 full bathroom, providing excellent options for rental income or multi-generational living. Situated on approximately one-half acre in Chester, this property offers a convenient location close to shopping, dining, and everyday amenities. Whether you're looking to offset your mortgage with rental income or invest in a versatile property, this unique opportunity is not to be missed.

231 Dominion Rd, Chester

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

129 Wheelhouse Way Unit 11, Chester
$585,000
2 Beds ⋅ 3 Baths
Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Magothy model is not only one of the closest residences to the Chester River, but also enjoys a premium location just one building away from the community clubhouse and only steps from the outdoor and indoor pools. One of the most unique advantages of this first-floor residence is its size. Unlike the second, third, and fourth-floor Magothy models, first-floor units offer approximately 100 additional square feet of living space, creating a more spacious and comfortable layout. Combined with more than $30,000 in post-purchase upgrades, this condo stands apart from the moment you walk through the door. By far the most impressive feature, however, is the extraordinary access to the waterfront. Step through your sliding glass doors and find yourself just moments from the Chester River. The peaceful setting allows you to enjoy water views, wildlife, and gentle river breezes from your private patio while offering one of the most coveted locations within the community. Whether you're taking a morning stroll along the shoreline or relaxing outdoors with a cup of coffee, the river feels like an extension of your backyard. Inside, luxury vinyl plank flooring flows throughout the home, complementing the bright, open floor plan filled with natural light from oversized windows and soaring ceilings. The gourmet kitchen is designed for both everyday living and entertaining, featuring a large center island, under-cabinet lighting, abundant cabinetry, and a custom dry bar area. The adjoining dining and living spaces create a seamless gathering area, highlighted by recessed lighting and a cozy electric fireplace. The spacious primary suite serves as a private retreat with dual closets and a beautifully upgraded bath featuring double vanities, custom tile work, a walk-in shower, and dual shower heads. A generous guest bedroom and adjacent full bath provide comfortable accommodations for family and visitors alike. Additional features include a private locked storage room, garage, custom finishes throughout, and a covered patio accented with stacked stone columns—an ideal place to unwind and enjoy the tranquil surroundings. With the clubhouse and pool just steps away, you'll enjoy unmatched convenience while still maintaining a peaceful and private setting. Residents of Four Seasons enjoy an exceptional resort-style lifestyle with a stunning clubhouse, indoor and outdoor pools, tennis and pickleball courts, fitness facilities, walking and biking trails, a community pier, and a full calendar of social activities coordinated by the community lifestyle director. Conveniently located near waterfront dining, marinas, golf courses, Annapolis, Baltimore, Washington, D.C., and BWI Airport, this is Eastern Shore living at its finest. Opportunities to own a first-floor waterfront-proximity unit in this location are exceptionally rare. With extra square footage, extensive upgrades, steps-to-the-pool convenience, and one of the closest locations in the community to the Chester River, this home offers a lifestyle that simply cannot be replicated.

129 Wheelhouse Way Unit 11, Chester

Listing courtesy of RE/MAX Executive. Contact:

7 Queen Victoria Way Unit B, Chester
$499,000
2 Beds ⋅ 3 Baths
Welcome to 7B Queen Victoria Way at Queen’s Landing, a beautifully renovated waterfront residence w/ spectacular views of the marina basin, marina fairway, and Chester River. The largest residence in Building 7, this spacious 2-bedroom, 2½-bath home with loft offers three levels of living and combines the ease of condominium ownership with the space and feel of a townhome. The extensive renovation creates a fresh, modern, move-in-ready interior featuring an open main level, wide-plank luxury vinyl flooring, refreshed baths, and an updated kitchen with white cabinetry, quartz countertops, stainless-steel appliances, pantry storage, and an eating bar. The waterfront primary bedroom enjoys beautiful views, while the versatile loft is ideal for a home office, guest area, reading retreat, or second sitting room. Step directly from the kitchen onto the gated walk-out waterfront patio and enjoy exceptional water and marina views, outdoor dining, entertaining, or simply watching the boats come and go. Multiple outdoor living areas provide even more opportunities to enjoy the waterfront setting. Queen’s Landing amenities include a waterfront pool and clubhouse, tennis and pickleball courts, fitness and racquetball facilities, scenic walking paths, kayak storage and launch areas, and a full-service marina with slips for sail and power boats. Major renovation, generous living space, outstanding views, and the Queen’s Landing waterfront lifestyle come together at 7B Queen Victoria Way. Offering the best of both worlds---condominium ownership with space, privacy, and multi-level layout of a townhome.

7 Queen Victoria Way Unit B, Chester

Listing courtesy of RE/MAX Allegiance. Contact:

101 Oak St, Stevensville
$539,990
4 Beds ⋅ 3 Baths
NEW CONSTRUCTION IN KENT ISLAND ESTATES – FOUNDATION IS IN! Welcome to 101 Oakwood, a brand-new Schaefer Homes Eastport model featuring 4 bedrooms, 2.5 baths and an attached garage, with expected completion in early 2027. Best of all—there’s still time to pick your finishes and make it yours! Enjoy an open, functional floor plan with gorgeous cabinetry and quartz countertops included as standard features. Upstairs you'll find four spacious bedrooms, all with great closet space, including a beautiful primary suite with walk-in closet, double vanity and tiled shower with frameless glass enclosure. Located in Kent Island Estates, enjoy a voluntary community association with community beaches and social events, plus nearby access to the South Island Trail, Blue Heron Golf Course, pickleball courts and Romancoke Fishing Pier. Get the custom-home feel without the custom-home price! The foundation is in, so now is the time to choose your finishes. Ask about the opportunity for a 3.99% interest rate!* *Special financing subject to lender terms, eligibility and availability.

101 Oak St, Stevensville

Listing courtesy of Samson Properties. Contact:

630 Warbler Way Unit 12, Chester
$549,950
2 Beds ⋅ 3 Baths
Experience everything Four Seasons at Kent Island has to offer without the wait! Less than one year old, this beautifully maintained home shows like new and offers one of the most desirable locations in the community, with exceptional water views, ground-level living, and an easy walk to the clubhouse and resort-style amenities. Plus, the home is still under warranty with the builder. Inside, you'll find an open-concept floor plan filled with natural light and beautiful water views. The gourmet kitchen features quartz countertops, upgraded cabinetry, GE Café appliances including double wall ovens, stainless steel appliances, tile backsplash, and plenty of space for entertaining. Luxury vinyl plank flooring flows through the main living areas, and an electric fireplace adds a cozy touch to the living room. The primary suite offers water views, private patio access, a large walk-in closet, and a spacious ensuite bath. A second bedroom suite provides a comfortable space for guests, while the private office offers flexibility for working from home or additional living space. Other upgrades include approximately $8,000 in remote-controlled window treatments, a private walk-out patio, climate-controlled storage, and an attached one-car garage. Step outside and enjoy the convenience of ground-level access and the waterfront lifestyle that makes Four Seasons so special. The 24,000-square-foot Chester House clubhouse is just a short walk away and features indoor and outdoor pools, a fitness center, yoga studio, game rooms, library, gathering spaces, and more. Residents also enjoy pickleball, tennis, bocce, walking and biking trails, a kayak and paddleboard launch, fishing and boat pier, dog park, waterfront beach area, fire pits, tiki bar, and a full calendar of clubs, fitness classes, and social events. Located on Kent Island just minutes from the Bay Bridge, Four Seasons offers easy access to Annapolis, Baltimore, DC, and Maryland's Eastern Shore. Waterfront dining, boating, golf, shopping, and the Chesapeake Bay lifestyle are all close by. Why wait for new construction when you can move right into a nearly new home with upgrades already completed?

630 Warbler Way Unit 12, Chester

Listing courtesy of RE/MAX Executive. Contact:

103 Worcester Rd, Stevensville
$619,990
4 Beds ⋅ 3 Baths
**NEW CONSTRUCTION IN KENT ISLAND ESTATES – BEING FRAMED NOW!** Welcome to 103 Worcester, a brand-new **Schaefer Homes Monroe model** featuring **4 bedrooms, 2.5 baths and a 2-car garage**, with expected completion in **early 2027**. Construction is underway, so now is the time to **come pick your finishes!** With so many upgrades already included, enjoy the look and feel of a custom home without the custom-home price. The Monroe offers an open main level with a spacious kitchen, dining area and great room—perfect for everyday living and entertaining—with all four bedrooms upstairs, including a private owner's suite with walk in tiled shower and double vanity. Located in **Kent Island Estates**, where the community association is voluntary, you'll enjoy access to community beaches and plenty of neighborhood social events. The **South Island Trail, Blue Heron Golf Course, pickleball courts and Romancoke Fishing Pier** are all nearby, putting some of the best of Kent Island recreation right outside your door. **Brand-new home. Your finishes. Island lifestyle.** Get in early and make 103 Worcester your own!

103 Worcester Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

300 Cemetery Ln, Church Hill
$685,000
4 Beds ⋅ 3 Baths
Rare opportunity to own an exceptional 8± acre residential farmette in Church Hill in Queen Anne's County! This versatile property features a 3-story, 4 bedroom, and 1 full bathroom and 2-half bathrooms farmhouse with 2,256 sq ft of living space, including a spacious living room, formal dining room, updated kitchen, sunroom, front porch, and patio surrounded by mature trees and established gardens. Perfect for an equestrian or hobby farm, the land includes 5± acres of pastures and a 2,600± sq ft barn equipped with 5 horse stalls, a large storage loft, an enclosed workshop, electric, and water. A separate 870± sq ft climate-controlled recreational outbuilding with a half bath offers the perfect footprint for a private home office, gym, or guest suite. Enjoy a private, secluded country setting without sacrificing convenience—located less than 0.5 miles from Rt 213 and 3.5 miles from Rt 301 for an easy commute. By Appointment Only - the road becomes the private driveway onto the property so viewing the property by driving by cannot be done.

300 Cemetery Ln, Church Hill

Listing courtesy of National Land Realty, LLC. Contact:

510 Auckland Way, Chester
$410,000
3 Beds ⋅ 3 Baths
Welcome home to this beautifully updated end-unit townhome in the desirable Bayside community, facing a peaceful row of trees. This spacious three-level home offers an open, inviting layout, beautiful hardwood floors, and numerous recent updates. Enter from the main-level foyer into a spacious bonus room—perfect for a family room, home office, gym, or additional entertaining space. Step directly outside to the back deck, where you can enjoy grilling and entertaining while overlooking the large grassy common area. Upstairs, the open-concept main living level features a spacious living room with a gas fireplace and access to a second deck, a dining area, and an updated kitchen, all complemented by beautiful hardwood flooring. A convenient updated half bath completes this level. The top floor offers three generously sized bedrooms. The primary suite features a beautiful custom accent wall and an updated primary bath, creating a comfortable and stylish retreat. The updated hall bathroom serves the additional bedrooms. Recent major updates include a new HVAC system (2025) and a new hot water heater (2026). Condo replaced roof and skylight (2025) & power-washed exterior (9/2026). All providing added peace of mind for the next owner. Enjoy all that the Bayside community has to offer, including an outdoor pool, hot tub, tennis/pickleball courts, clubhouse with meeting/party room, and exercise room. The location is ideal for an active lifestyle, with a short walk to the Chester River, a local pub, the Cross Island Trail, and a marina. You'll also enjoy easy access to the Bay Bridge, restaurants, shopping, and all that Kent Island and Maryland's Eastern Shore have to offer. Move-in ready, beautifully updated, and perfectly situated—this Bayside townhome is ready to welcome you home!

510 Auckland Way, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

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