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193 Spinnaker Way, Chester
$835,000
3 Beds ⋅ 3 Baths
Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors. A chef's dream, the Gourmet Kitchen is the heart of the home, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining, and a separate beverage center! Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers a spacious loft, a flexible area perfect for a second family room, hobby space, and an additional bedroom and bathroom for overnight guests. Also, the large above attic storage room is fully finished. More storage is available in the oversized fully finished two car garage with extra room for a golf cart. Off the dining area is a screened-in porch and patio, and the community run irrigation system to keep your lawn lush and green! You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis (17 miles), DC (45 miles), Baltimore (45 miles), and BWI (30 miles). Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by endless views of the Chester River.

193 Spinnaker Way, Chester

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

Selling Office: Non Subscribing Office.

110 Kinglet Ct, Chester
$834,990
5 Beds ⋅ 5 Baths
The Tuscaloosa home offers a thoughtfully designed layout with elevated finishes throughout, with a projected settlement of April 2026. Featuring 2 bedrooms, 2.5 baths, and a 3-car garage, this home blends everyday functionality with timeless style. Standout features include a dedicated home office, a screened patio perfect for outdoor relaxation, and a shiplap-accented fireplace paired with ceiling beams that add warmth and architectural character to the great room. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all finished with Quartz countertops that continue into the owner’s bath for a cohesive, upscale look. Luxury Vinyl Plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, HovHall, owner’s suite, and extra suite, while tile enhances all full baths. Carpeted secondary spaces provide comfort in additional bedrooms and the loft. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a relaxing retreat. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

110 Kinglet Ct, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

110 Boatswain Way Unit 3031, Chester
$830,000
3 Beds ⋅ 3 Baths
The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat, complete with a private sitting room and large walk-in closets. The spa-inspired owner’s bath features a walk-in shower with seat and handheld wand, double sinks, and quartz countertops. The kitchen is equipped with a gas cooktop, single oven, microwave, range hood, dishwasher, pendant lighting, and a tile backsplash, all anchored by quartz countertops. Laminate flooring flows throughout the home, with tile in both full bathrooms for a polished finish. 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.

110 Boatswain Way Unit 3031, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

115 Thicket Ct, Centreville
$825,000
4 Beds ⋅ 4 Baths
Discover an exquisite blend of modern luxury and serene living in this stunning home nestled within the prestigious Willow Branch East community. Built in 2022, this exceptional home boasts 3,011 square feet of meticulously designed space, offering an unparalleled lifestyle for those who appreciate the finer things in life. There is also approximately 1478sf of unfinished basement. Step inside to find an open floor plan that seamlessly integrates the living, dining, and kitchen areas, creating an inviting atmosphere perfect for both entertaining and everyday living. The gourmet kitchen is a chef's dream, featuring high-end stainless steel appliances, including a built-in microwave, down-draft cooktop, and wall oven, all complemented by a spacious island and ample table space. The elegant dining area and formal dining/office room provide the perfect backdrop for memorable gatherings. The heart of the home is the family room, where a stunning gas fireplace with glass doors and a stylish mantel creates a warm and inviting focal point. Recessed lighting and ceiling fans enhance the ambiance, while luxury vinyl plank flooring adds a touch of sophistication throughout. This residence offers four generously sized bedrooms, including a main-level bedroom for convenience. The primary suite is a true retreat, featuring a lavish en-suite bathroom and expansive walk-in closets. Step outside to your own personal oasis, where a spacious deck overlooks a beautiful yard that backs to tranquil trees, providing a serene escape from the hustle and bustle of daily life. The 1.42-acre lot offers ample space for outdoor activities and gatherings, while the attached side-entry garage and asphalt driveway provide convenience and curb appeal. Additional highlights include a main-floor laundry room, a tankless water heater for endless hot water, and an unfinished walkout basement with a Sauna and endless potential for customization. Enjoy relaxing in the outdoor Hot Tub located just steps away from the Sauna. This home is not just a residence; it's a lifestyle choice that embodies luxury, comfort, and tranquility. Also included are 6 wall mounted TV’s, Sauna, Hot Tub and a one year home warranty. Easy commute to DC, the Western Shore and the Eastern Shore beaches. Sellers are offering a $5000.00 allowance for paint.

115 Thicket Ct, Centreville

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: Samson Properties.

5 Prospect Bay Dr W, Grasonville
$820,000
4 Beds ⋅ 3 Baths
This charming ranch-style home in the desirable Prospect Bay community offers a perfect blend of comfort and elegance. With 4 spacious bedrooms and 3 full baths, the traditional floor plan features a cozy family room off the gourmet kitchen, ideal for gatherings. Enjoy upgraded countertops and a pantry, complemented by modern stainless steel appliances and huge center island. The large 3 Season room offers great flex space and views of the course. Enjoy the benefits of a tankless hot water, too! Step outside to a serene 1.01-acre lot with a rear yard, perfect for outdoor activities. The expansive deck invites you to relax while taking in stunning views of the nearby golf course. Community amenities include a refreshing pool and easy access to Prospect Bay, where you can enjoy canoeing, kayaking, and fishing. Conveniently located less than 10 miles from the airport, this home also boasts an oversized attached garage and ample driveway parking. Experience the warmth of this inviting residence, where every detail is designed for comfort and enjoyment.

5 Prospect Bay Dr W, Grasonville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

751 Ruthsburg Rd, Centreville
$817,000
7 Beds ⋅ 4 Baths
Welcome to 751 Ruthsburg Rd. in Centreville, Maryland—a truly one-of-a-kind farmette offering over 6 acres of privacy, rolling hills, and a picturesque pond, all just minutes from town. Beautifully renovated throughout, this expansive 7-bedroom, 3.5-bath home blends modern updates with timeless character and space to grow. From the moment you step inside, you’ll appreciate the generous living areas designed for both everyday comfort and effortless entertaining. At the heart of the home is a stunning, fully updated kitchen featuring a walk-in pantry and a seamless flow into the dining room. Here, vaulted ceilings and dramatic floor-to-ceiling windows flood the space with natural light while framing peaceful views of the surrounding landscape—creating a setting that truly connects indoor living with the beauty of nature. The first floor also offers a thoughtfully designed mudroom and laundry area complete with custom built-in cubbies—perfect for an active or growing household. Additionally, you’ll find a versatile and private in-law suite or main-level primary suite, featuring high ceilings that enhance the sense of space, along with its own kitchenette, spacious living room, large bedroom, and a beautifully appointed full bathroom. Upstairs, the second level includes four well-sized bedrooms with ample closet space and a fully updated bathroom. The third floor adds even more flexibility, offering a generously sized primary bedroom, an additional bedroom, and a half bath, along with unfinished space already prepped for a future full bathroom—giving you the opportunity to expand even further. Outside, the property is just as impressive. With over 6 acres of serene land, a private pond, and gently rolling terrain, this farmette offers endless possibilities—whether you’re looking for a peaceful retreat, hobby farm, or space to spread out and enjoy. An expansive garage provides abundant room for vehicles, equipment, or additional storage. Properties like this are rare—offering privacy, acreage, modern updates, and close proximity to all the shopping, dining, and conveniences of Centreville. Talkie fiber optic internet is the current internet provider and a line for Atlantic broadband has been run which is also an internet option. Schedule your private showing today and experience everything this exceptional property has to offer.

751 Ruthsburg Rd, Centreville

Listing courtesy of Taylor Properties. Contact:

Selling Office: EXP Realty, LLC.

114 Piper Ct, Church Hill
$805,000
4 Beds ⋅ 4 Baths
Welcome home to this beautifully custom-built home set on 2.5 acres, where thoughtful design and stylish upgrades come together for everyday comfort and easy living. The spacious first-floor primary suite offers the convenience you’ve been looking for, while a dedicated home office provides the perfect spot for working remotely, studying, or simply having a quiet flex space. At the heart of the home, the bright and inviting kitchen features upgraded appliances and flows seamlessly into the main living areas—ideal for entertaining or relaxed nights in. You’ll love the LVP flooring throughout and the abundance of upgrades that elevate every space. Step outside and unwind on the large covered back porch, a favorite place to enjoy morning coffee, evening sunsets, or gatherings with friends and family—surrounded by the privacy and open space that 2.5 acres provides. Upstairs, you’ll find two comfortable bedrooms connected by a convenient Jack-and-Jill bath, plus an additional room that can easily serve as a playroom, media room, hobby space, or extra bedroom—whatever fits your lifestyle. Above the garage, you’ll appreciate the unfinished storage space with an already framed-in doorway—perfect for extra storage now or ready to be finished into another room in the future. This one truly checks all the boxes: space, quality, upgrades, and that unmistakable “welcome home” feeling.

114 Piper Ct, Church Hill

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: RLAH @properties.

1604 Midway Rd, Chester
$800,000
4 Beds ⋅ 3 Baths
Discover the perfect blend of tranquility and recreation in Marling Farms, where this stunning 1.01-acre lot awaits your vision. Imagine a lspacious yard that invites outdoor gatherings and serene moments under the stars, complemented by a personal gunite pool, perfect for summer relaxation. Just shy of 3000 square feet of liviing space gives everyone plenty of room to spread out complete with multiple living spaces, home office and first floor primary. This property boasts direct access to Crab Alley Bay, ideal for boating, kayaking, and fishing enthusiasts. Enjoy the community's exceptional amenities, including a beach, picnic area, baseball field, and basketball courts, fostering a vibrant neighborhood spirit. With an oversized side-entry garage and ample driveway space for guests, convenience is at your fingertips. The peaceful surroundings and proximity to local attractions make this location a true gem. Embrace the lifestyle you've always dreamed of in a community that offers both adventure and serenity. Don't miss this opportunity to create your own oasis in Marling Farms!

1604 Midway Rd, Chester

Listing courtesy of Wilson Realty & Staging LLC. Contact:

Selling Office: EXIT First Realty.

115 Masters Way, Grasonville
$800,000
4 Beds ⋅ 4 Baths
Great price improvement! Welcome to The Enclave at Prospect Bay, where this former model home showcases the sought-after “Pebble Beach” floor plan with thoughtful upgrades and timeless details, backing directly to the 18-hole golf course. Designed for both everyday living and entertaining, the home features three first floor bedrooms, three and a half bathrooms, and a spacious walk-up “sky basement” with a full bath—ideal as a fourth bedroom, office, or media room. The chef’s kitchen offers Quartz countertops, wall oven, cooktop, ceramic tile backsplash, pantry, and a large island that opens to the dining area and family room.  There is a bonus coffee or wine bar with mini fridge, stylish glass cabinets, and additional storage located off the kitchen. In the living room, a custom fireplace with built-ins creates a warm focal point, while expansive windows and plantation shutters throughout the home invite natural light. The main-level primary suite includes a spa-like bath with dual vanities, a walk-in shower, and private water closet. Two additional bedrooms and a versatile bonus room provide flexible living space. Step outside to a spacious patio overlooking the 11th hole—perfect for entertaining or simply enjoying the views. The fenced yard is beautifully landscaped with flourishing gardens and an in-ground sprinkler system, while the HOA maintains the yard for a low-maintenance lifestyle. Additional highlights include a mudroom/laundry room off the two-car garage and efficient upgrades such as the Rinnai tankless water heater. Living in Prospect Bay means access to an array of community amenities including an 18-hole golf course, clubhouse with dining, marina, pool, tennis and pickleball courts, and year-round social activities. Here, every day feels like a vacation.

115 Masters Way, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

4 Bunkers Ct, Grasonville
$800,000
3 Beds ⋅ 4 Baths
Enjoy a waterfront country club lifestyle with the privacy of wooded views at 4 Bunkers Court! This beautifully updated and private creek front home is tucked away on a wooded 1.53 acre cul-de-sac lot at the top of Little Greenwood Creek in the sought after waterfront golf course community of Prospect Bay. From soaring vaulted ceilings and over $100k of recent thoughtful upgrades throughout, this home combines comfort, style, and space indoors and out. Step inside to a welcoming foyer and formal dining room with updated lighting. The showstopper of the home is the stunning family room featuring vaulted wood planked ceilings and a striking stone fireplace, an architectural focal point that adds warmth and character. The updated kitchen is a chef's delight with new stainless steel Frigidaire Gallery appliances, granite countertops, freshly installed tile backsplash, new flooring, and a sleek hood vent. A cozy breakfast nook with custom built-ins offers extra storage and bar countertop seating. Just off the kitchen, you’ll find a new mudroom and laundry area with two additional storage closets and a newly added powder room, all connecting to the oversized two-car garage for everyday convenience. The main level offers three bedrooms and two full bathrooms, including a serene primary suite with private patio access, two closets, and a fully updated en suite featuring a walk-in glass enclosed shower with overhead and wall mounted shower heads, and a double vanity with modern finishes. Upstairs, a spiral staircase leads to a spacious and versatile loft ideal as a fourth bedroom, office, or entertaining space. This grand loft includes a game and TV area, pool table, full bathroom with designer tile and a glass shower door, and a custom-built bar area with a beverage fridge, microwave, sink, cabinetry, and backsplash perfect for hosting guests in style. Outside, step onto your private bluestone patio and hot tub, surrounded by the natural beauty of your wooded lot. The sellers have explored the potential of building a boardwalk to the creek with a floating dock buyers to verify offering exciting possibilities for enjoying the waterfront setting. Living in Prospect Bay means more than just a beautiful home, it’s a lifestyle. Enjoy first class amenities including a championship 18 hole golf course, tennis and pickleball courts, outdoor pool, clubhouse with dining, social events, boat basin, and more. Whether you're hosting in the open concept living spaces, relaxing in your upstairs retreat, or soaking in the serenity of your private wooded backyard, 4 Bunkers Court is the perfect place to call home!

4 Bunkers Ct, Grasonville

Listing courtesy of Washington Fine Properties. Contact:

Selling Office: Real Broker, LLC - Annapolis.

107 Thicket Ct, Centreville
$800,000
4 Beds ⋅ 4 Baths
New Construction in Willow Branch Community - Only 5 Lots Left! Build your dream home with Mike's Custom Homes in the sought after Willow Branch Community in Centreville, MD! Choose from three stunning models or bring your own custom floor plan to create the perfect home tailored to your needs. Nestled in a serene setting with spacious lots, high-quality craftmanship, and modern finishes, these homes offer the best of the Eastern Shore living. Don't miss this opportunity to build in a prime location with easy access to local amenities, schools and major routes. Secure your lot today - contact us for more details! **Photos are of a previously sold model and may feature options that are upgrades. *Additional lot premium fees will apply.

107 Thicket Ct, Centreville

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Samson Properties.

259 Redstart Dr, Chester
$799,990
4 Beds ⋅ 3 Baths
The Simone at Lot 547 features a well-balanced open-concept floorplan with a projected settlement date of March 2026, offering both style and functionality for modern living. This home includes 4 bedrooms, 3 baths, and a 2-car garage, with flexible spaces designed to adapt to everyday needs. Notable highlights include a dedicated home office and a welcoming shiplap-accented fireplace that anchors the main living area. Luxury vinyl plank flooring flows through the foyer, extended foyer, kitchen, dining area, great room, Bedroom 2, the owner’s suite, and the HovHall, while tile finishes enhance all full baths and the laundry room. Plush carpet adds comfort to the loft, second floor, and Bedrooms 3 and 4. The kitchen is thoughtfully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a tile backsplash, all paired with quartz countertops that continue into the owner’s bath. The owner’s bath is designed for comfort with a shower featuring a built-in seat, handheld shower wand, and double sinks. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

259 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: The KW Collective.

528 Warbler Way, Chester
$799,500
4 Beds ⋅ 3 Baths
Like-new luxury living in Four Seasons at Kent Island. Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine, move-in-ready feel. Highlights include luxury vinyl plank flooring, quartz countertops, and over $20,000 in custom window treatments, can you say "plantation shutters". Professionally decorated throughout—with the option to purchase furnishings—this home is truly turn-key and ready today. Enjoy peek-a-boo Chester River views and an unbeatable location so close to the clubhouse you can see it. Plus, the builder’s full warranty remains in place through August 2026 for added peace of mind. Residents enjoy Four Seasons’ resort-style amenities: waterfront clubhouse, indoor & outdoor pools, fitness center, pickleball & tennis, walking trails, and a vibrant social calendar. Effortless luxury, prime location, island living at its best.

528 Warbler Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Keller Williams Flagship.

136 Nauset Ln, Chester
$799,000
3 Beds ⋅ 3 Baths
Welcome to 136 Nauset Lane, an upgraded Lille model in Four Seasons at Kent Island, a premier 55+ resort-style community. Situated on a corner lot, this Coastal Traditional home offers the ease of main-level living, flexible space for guests and an impressive list of thoughtful upgrades already in place. LVP flooring flows throughout the main level, where a private office with custom California Closets built-ins provides a dedicated work or hobby space. The open-concept kitchen and family room create an inviting heart of the home, complemented by a light-filled sunroom. The kitchen features a generous island, Café/Monogram stainless steel appliances, built-in microwave, pantry, dry bar and cabinetry with double pull-out shelving. The refrigerator was replaced in 2026. Just beyond the sunroom, a screened porch with a ceiling fan opens to a beautiful paver patio with a remote-controlled electric awning, creating multiple spaces to relax, entertain and enjoy the outdoors. The spacious main-level primary suite features a large walk-in closet professionally designed by California Closets. The primary bath offers a walk-in shower, private water closet, linen closet and additional cabinetry for storage. A second bedroom and full bath are also conveniently located on the main level. Upstairs, a third bedroom, full bath and sitting area provide a private and comfortable space for overnight guests. Thoughtful upgrades continue throughout the home with ceiling fans in all three bedrooms and the family room, a California Closets-designed coat closet, central vacuum, Ethernet connections in most rooms, whole-house Wi-Fi distribution, security system, smart thermostat, remote-access garage door, Speed Queen washer and dryer and EV charging in the garage. The lawn irrigation system draws water from the community pond, with seasonal winterization handled by the HOA. Then there is the Four Seasons lifestyle. At the center of the community is the impressive 24,000-square-foot waterfront Chester House clubhouse, complemented by indoor and outdoor resort-style pools, spa, modern fitness center, yoga room, pickleball and tennis courts, bocce ball, walking paths and an outdoor amphitheater. Enjoy the beach area with fire pits, or head to the 450-foot fishing pier and kayak launch to get out on the water. A full-time lifestyle director keeps the social calendar active with activities and events throughout the year. It’s resort-style living designed to be enjoyed every day. With very few new homes remaining in the community, why wait months for new construction? 136 Nauset Lane is move-in ready with an extensive list of upgrades already completed, offering the opportunity to start enjoying the Four Seasons at Kent Island lifestyle now.

136 Nauset Ln, Chester

Listing courtesy of RE/MAX One. Contact:

Selling Office: Samson Properties.

110 Channel Marker Way Unit 203, Grasonville
$795,000
4 Beds ⋅ 4 Baths
This boater's paradise demonstrates the perfect blend of luxury and convenience. The property boasts three floors of sweeping waterfront views all easily accessed via your own private elevator. High end finishes can be found throughout and the home has been impeccably maintained. The first floor feels inviting with the fireplace, open kitchen, and guest bedroom with ensuite full bathroom currently being used as an office. The second floors wows you with 3 spacious bedrooms including the primary that has a walkout balcony for quiet evenings staring out over the water. The top floor provides yet another entertaining or living space with a wet bar, full bathroom, and a walk out balcony. Outdoor living in general is a highlight here with each floor allowing for a different perspective of the Eastern Shore landscape. Don't forget about the amenities of the community. Lounge out by the pool, walk to famous waterfront seafood establishments, or navigate the vast waters of the Chesapeake from your deeded boat slip - #49 - just steps away. This luxury Eastern Shore destination is located just an hour from Washington, D.C. or Baltimore and less than two hours from Philadelphia.

110 Channel Marker Way Unit 203, Grasonville

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

Selling Office: Eastern Shore Real Estate, LLC.

117 Woodfield Ct, Centreville
$790,000
3 Beds ⋅ 3 Baths
Searching for a property that truly stands out? This fully upgraded custom designed home offers the perfect blend of luxury and privacy. From the moment you turn onto the driveway, you'll already be in love! Greeted by a long gravel driveway, oversized parking area and breathtaking curb appeal that only gets better as you head to your grand entrance front covered porch. Set on a large lot with thoughtfully planted trees for future privacy, rows of whimsical wildflowers, scenic farmland views and extensive landscaping, the setting feels both peaceful and refined. Inside, the wide open floorplan is anchored by a stunning gas fireplace that creates a warm focal point for the main living space, while the oversized kitchen island is perfect for everyday dining or weekend entertaining. A butler’s pantry provides exceptional storage for appliances and kitchen essentials, and the luxurious primary suite features an elevated bathroom and enormous walk in closet that conveniently wraps around to the main level laundry room. Just beyond the main living area, the attached three seasons room showcases floor to ceiling glass views, creating the perfect space to enjoy the Eastern Shore of Maryland’s changing seasons in year round comfort. Downstairs, the unfinished basement with a walk out staircase offers endless potential for future living space, recreation or storage, while the detached building with its own electric meter, concrete pad and covered lean to adds incredible flexibility for hobbies, equipment or workshop space.

117 Woodfield Ct, Centreville

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: TTR Sotheby's International Realty.

135 Nauset Ln, Chester
$787,500
3 Beds ⋅ 3 Baths
If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities. But what really sold them was the way this home made everyday life feel easy, peaceful, and a little bit indulgent. From the moment you walk through the front door, the open layout just flows. The gourmet kitchen is the heart of the home—with a massive island, double ovens, gas cooktop, and more cabinet space than you’ll know what to do with. It opens to a sunny dining area and a living room that invites you to sink in and stay awhile. Downstairs, you’ll find two spacious bedrooms, including a primary suite that feels like a retreat. The spa-like bathroom, walk-in closet, and tray ceiling add a touch of everyday luxury. There’s also a den that can flex into a home office, reading room, or whatever you need it to be. Upstairs is a private guest suite with a third bedroom, full bath, and a bonus loft space that’s perfect for movie nights or extra living space. But the magic continues outside. The oversized patio was made for entertaining—complete with a built-in firepit, gas line for your grill , and even a five-person Thermospa hot tub. Whether it’s coffee in the morning or wine after sunset, this is where you’ll want to be. Other thoughtful touches? There’s a heated and cooled garage with extra space for a third vehicle or golf cart, and a sky basement for bonus storage. Throughout the home, you'll find upgrades like luxury vinyl plank flooring, under-cabinet kitchen lighting, custom bathroom finishes, recessed lighting, and so much more. And then there’s the community. Four Seasons at Kent Island is truly one-of-a-kind. Want to start your day with yoga? Go for a paddle on the river? Meet friends at the outdoor bar to catch the game by the firepit? It's all here. There’s a 24,000 sq ft clubhouse, both indoor and outdoor pools, a state-of-the-art gym, game room, pickleball and tennis courts, walking and biking trails, a pier for fishing and boating, a kayak launch, and even a dog park. The community is tucked away, peaceful and private—but you're just minutes from restaurants, wineries, breweries, and shops. And if you ever need a city fix, Annapolis and Easton are an easy 20-30 minute drive away. The best way to describe this home and community? It’s a place where life slows down in the best way. Where neighbors become friends. Where the to-do list gets a lot shorter—and the “want-to-do” list gets a whole lot longer. So if you're looking for more than just a new house—if you're ready for a new chapter filled with connection, ease, and everyday joy—135 Nauset Lane might be exactly what you’ve been waiting for.

135 Nauset Ln, Chester

Listing courtesy of Real Broker, LLC - Annapolis. Contact:

Selling Office: Real Broker, LLC.

255 Redstart Dr, Chester
$780,000
4 Beds ⋅ 3 Baths
The Simone is a beautifully designed home with a projected settlement of May 2026, offering the space and features you are looking for. With 4 bedrooms, 3 full baths, and a 2-car garage, this home balances everyday comfort with thoughtful design details. A dedicated home office provides the perfect space for remote work or study, while the great room is anchored by a striking two-story shiplap fireplace with a granite surround, creating a warm and inviting focal point. The kitchen is well-appointed with a gas cooktop, single oven, microwave, range hood, dishwasher, French-door refrigerator, and pendant lighting, complemented by a tile backsplash and quartz countertops that continue into the owner’s bath. LVP flooring flows through the foyer, kitchen, dining area, great room, owner’s suite, and bedroom two, while tile finishes the full baths and laundry room. Plush carpeted spaces in the loft, second floor, and additional bedrooms add comfort where it counts. The owner’s bath features a spa-like shower with seating, a handheld wand, and double sinks for added convenience. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

255 Redstart Dr, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

354 Claiborne Fields Dr, Centreville
$777,500
4 Beds ⋅ 3 Baths
Welcome to 354 Claiborne Fields Drive, a beautifully updated home offering over 3,100 square feet of thoughtfully designed living space on a picturesque 1.25-acre lot in Centreville, Maryland. Built in 2000, this exceptional two-story residence combines timeless design with modern updates, creating the perfect setting for everyday living and effortless entertaining. Step inside to a welcoming foyer that opens to spacious, light-filled living areas. The flowing floor plan seamlessly connects the living room, dining room, and recently renovated kitchen, creating an inviting atmosphere for family gatherings and entertaining. A cozy fireplace serves as the focal point of the separate family room, while the updated kitchen features quartz countertops, modern stainless steel appliances, abundant cabinetry, a center island, and ample workspace for the home chef. The home offers generously sized bedrooms and three full bathrooms, including a spacious primary suite, large walk-in closet and an en-suite bath with dual vanities, a soaking tub, and a separate walk-in shower. Throughout the home, you’ll appreciate numerous recent improvements, including new flooring on the main level, an updated bathroom, and a brand-new roof, providing both style and peace of mind for years to come. Step outside to your own private backyard oasis. The beautifully landscaped grounds showcase a spectacular 20’ x 40’ resort-style swimming pool with a waterfall feature, a large lighted pergola perfect for outdoor entertaining, and a separate screened porch for relaxing evenings. The expansive 1.25-acre lot offers exceptional privacy and plenty of space for recreation, gardening, or simply enjoying the outdoors. Additional highlights include a spacious three-car garage and a location that combines country living with convenient access for commuters. This well maintained property offers the perfect blend of comfort, luxury, and outdoor living. With its impressive updates, resort-style backyard, and exceptional setting, 354 Claiborne Fields Drive is truly a place you’ll be proud to call home.

354 Claiborne Fields Dr, Centreville

Listing courtesy of Hawkins Real Estate Company. Contact:

Selling Office: Keller Williams Flagship.

539 Warbler Way, Chester
$769,990
3 Beds ⋅ 3 Baths
Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors—perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

539 Warbler Way, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

176 Flagstaff Way Unit 2433, Chester
$769,990
2 Beds ⋅ 3 Baths
The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar ideal for entertaining, an electric fireplace for added ambiance, and a convenient storage room to keep everything organized. Luxury vinyl plank flooring runs throughout the home, with tile in both full baths for durability and easy maintenance. The kitchen is well-appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops. The owner’s bath features a shower with seat, handheld shower wand, double sinks, and quartz countertops, creating a comfortable and refined 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.

176 Flagstaff Way Unit 2433, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: KW Metro Center.

715 Warbler Way, Chester
$764,990
4 Beds ⋅ 3 Baths
Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

715 Warbler Way, Chester

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

Selling Office: Unrepresented.

129 Sailcloth Way, Chester
$764,900
3 Beds ⋅ 2 Baths
Welcome to 129 Sailcloth Way in the resort-style community of Four Seasons at Kent Island! This beautifully upgraded Kilarney model offers over 2300 square feet of single-level living, an open layout, and designer finishes throughout. Move-in ready and available now - no need to wait months for new construction. Inside, you'll find a spacious gourmet kitchen with GE Profile appliances, gas cooktop, double oven, quartz countertops and backsplash, a large island, under-cabinet lighting, and a convenient wine bar. The kitchen flows seamlessly into the bright dining area and the expansive great room with a gas fireplace, creating the perfect space for everyday living and entertaining. This home includes 2 bedroom, 2 full baths, and a flex room idea for a home office or a third bedroom. The impressive owner's suite features a walk-in closet, and a private bath with a quartz-topped double vanity. Additional upgrades include custom window treatments, upgraded lighting, and an oversize garage that is insulated, as well as a finished and insulated attic - all already installed, saving you thousands compared to new construction. Four Seasons at Kent Island offers exceptional amenities, including a brand-new 24,000 sq. ft. clubhouse overlooking the Chester River, outdoor infinity pool, indoor pool, fitness center, game room, library, fire pits, Tiki bar, walking paths, pickleball and tennis courts, bocce, dog park, amphitheater, and pier with transient boat slips. A full-time lifestyle director coordinates daily activities, clubs, classes and community events year-round. Experience true resort-style living on Kent Island!

129 Sailcloth Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Taylor Properties.

126 Claiborne St, Chester
$764,000
3 Beds ⋅ 3 Baths
Welcome to 126 Claiborne Street in the sought-after Gibson's Grant community on Kent Island — a beautifully crafted Covell-built Sawgrass model offering the perfect blend of coastal charm and comfortable with peaceful pond and park views right outside your door This thoughtfully designed home features 3 bedrooms, 2.5 baths, and a desirable main-level primary suite complete with a private en suite bath for easy everyday living. The heart of the home is the updated kitchen, showcasing quartz countertops, stainless steel appliances, and timeless hardwood floors that continue throughout the main living spaces. Upstairs, you'll find two additional bedrooms, a full bath, and a spacious rec room that provides the perfect second living area, home office, or guest retreat. Enjoy outdoor living with a covered front porch, a screened porch for relaxing evenings, and an additional open porch overlooking the fenced side yard — ideal for entertaining or enjoying the peaceful surroundings. A rear-entry 2-car garage adds both convenience and curb appeal. Residents of Gibson’s Grant enjoy exceptional resort-style amenities, including a community pool, clubhouse, fitness center, kayak launch, fishing and crabbing pier, waterfront pavilion, and direct access to the Cross Island Trail — all just minutes from the dining, marinas, and attractions of Kent Narrows.

126 Claiborne St, Chester

Listing courtesy of Samson Properties. Contact:

Selling Office: Samson Properties.

127 Pleasant Springs Dr, Centreville
$749,900
4 Beds ⋅ 4 Baths
Welcome to 127 Pleasant Springs Drive, a beautifully maintained home nestled in the highly desirable Claiborne Fields community of Centreville. This four‑bedroom, 3.5‑bath residence offers the perfect blend of comfort, style, and functionality—truly an ideal place to call home. Set on 4.0 picturesque acres, the property includes 2.1 acres owned plus an additional 1.937 acres under a 99‑year lease, with an invisible dog fence already in place. A welcoming front porch overlooks a freshly manicured, park‑like landscape featuring perennial gardens, a dedicated herb garden, and a full fruit orchard, creating a serene and private setting. Designed for both relaxing and entertaining, the home offers a screened porch perfect for summer gatherings, along with a private hot tub for year‑round enjoyment. Inside, the main living areas flow seamlessly. The well‑appointed kitchen features generous cabinetry and workspace and opens to the dining area and family room, complete with custom built‑ins and a cozy fireplace. A separate office or playroom adds valuable flexibility for today’s lifestyle. The spacious primary suite is a true retreat, offering ample closet space and a spa‑like ensuite bath with a jetted tub, walk‑in shower, and double vanity. Additional bedrooms provide comfort and privacy for family and guests alike. The partially finished basement includes a full bathroom, separate exterior entrance with stairwell, and a full bathroom, creating excellent potential for an in‑law suite, guest space, or recreation area. A detached four‑car garage provides abundant storage and versatility. Buy with confidence knowing the home features a newer roof, water heater, water tank, and updated appliances. Outdoor spaces are thoughtfully designed for low‑maintenance enjoyment���perfect for morning coffee or evening relaxation. Claiborne Fields is known for its peaceful atmosphere, expansive one‑plus‑acre lots, and convenient proximity to downtown Centreville, shopping, dining, parks, and major commuter routes. This exceptional home offers comfort, privacy, and community in one of Queen Anne’s County’s most sought‑after neighborhoods. Schedule your private tour today—you won’t want to miss it.

127 Pleasant Springs Dr, Centreville

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

Selling Office: Long & Foster Real Estate, Inc..

711 Warbler Way, Chester
$739,990
4 Beds ⋅ 3 Baths
Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors—perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner’s bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner’s suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner’s bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

711 Warbler Way, Chester

Listing courtesy of KOVO Realty. Contact:

Selling Office: Unrepresented.

212 Switchgrass Way Unit 34, Chester
$735,000
3 Beds ⋅ 3 Baths
Best View of the Chester River. Check it out! Experience elevated Eastern Shore living in this beautifully appointed corner residence overlooking the Chester River in the sought-after 55+ waterfront community of K. Hovnanian’s Four Seasons at Kent Island. Just one year old and impeccably maintained, this spacious three-bedroom, two-and-a-half-bath home offers more than 2,600 square feet of upscale living with the feel of brand-new construction — without the wait. The open-concept design is filled with natural light thanks to the desirable end-unit location and abundance of windows throughout. At the center of the home is a stunning gourmet kitchen featuring quartz countertops, GE Profile appliances, gas cooking, under-cabinet lighting, abundant cabinetry, and an oversized island perfect for gathering and entertaining. The kitchen opens seamlessly into the expansive living and dining areas, with sliding doors leading to a large private corner balcony ready for relaxing afternoons, sunset skies, and those signature Chester River breezes. The luxurious primary suite serves as a private retreat with its own sitting area, balcony access, spa-inspired bath, and two oversized walk-in closets. Two additional bedrooms are tucked away in a separate wing for privacy and share a Jack-and-Jill bath, while each still features its own walk-in closet. Additional highlights include luxury plank flooring, recessed lighting, a dedicated laundry room, powder room, garage parking, private driveway space, and a spacious storage room conveniently located near the elevator. Why wait months for new construction when this upgraded residence is available now? Unlike builder inventory, this home already includes premium finishes and designer upgrades throughout — all move-in ready and lightly lived in. Residents enjoy access to an impressive 24,000-square-foot clubhouse with panoramic water views and an unmatched lineup of resort-style amenities. Community features include indoor and outdoor pools, fitness facilities, pickleball and tennis courts, walking trails, bocce, dog park, fire pits, amphitheater events, marina access, and a vibrant social calendar packed with clubs, classes, and seasonal gatherings. Conveniently located near Annapolis, Baltimore, Washington D.C., and BWI Airport, Kent Island offers the perfect blend of waterfront relaxation, dining, shopping, and outdoor recreation along Maryland’s Chesapeake Bay.

212 Switchgrass Way Unit 34, Chester

Listing courtesy of RE/MAX Executive. Contact:

Selling Office: Compass.

113 Brix Dr, Church Hill
$730,000
3 Beds ⋅ 3 Baths
Welcome to 113 Brix Drive, a beautifully maintained 2834 finished square foot home built in 2019 and located in the desirable water-oriented community of The Preserve at Southeast Creek, with access to Southeast Creek. Offering 3 bedrooms, 2.5 baths, and a large detached garage, this property combines comfortable living with exceptional flexibility. The main level features an inviting eat-in kitchen, spacious living room, formal dining room, and a versatile office/flex space that can easily adapt to your needs. Upstairs, the primary suite opens to a loft area perfect for a home office, reading nook, fitness space, or private retreat. Two additional bedrooms and a full bath complete the upper level. The 1430 square foot basement has been framed and dry wall started. There is a roughed in bathroom and it provides additional living space and the opportunity to expand even further, making it ideal for recreation, hobbies, storage, or future finishing. Step outside to enjoy the large rear deck overlooking the backyard, a dedicated fire pit area, and plenty of space for outdoor entertaining and everyday enjoyment. One of the standout features of this property is the detached 3+ car garage, complete with a vehicle lift that conveys with the sale. Whether you're a car enthusiast, hobbyist, contractor, or simply need extra storage and workspace, this impressive garage offers endless possibilities. Conveniently located in Church Hill, this home offers the perfect blend of modern construction, functional living space, outdoor enjoyment, and water access. Schedule your private tour today and discover everything 113 Brix Drive has to offer.

113 Brix Dr, Church Hill

Listing courtesy of Patterson-Schwartz Real Estate. Contact:

Selling Office: Long & Foster Real Estate, Inc..

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