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334 Eagle Manor Dr, Church Hill
$549,900
4 Beds ⋅ 3 Baths
GREAT NEW PRICE! Makes this home hard to resist. Newly Built, Move-In Ready Home on a Full Acre in Condor Manor! Why wait to build? This beautifully finished 2026 home is complete, move-in ready, and situated on a spacious one-acre lot in Church Hill’s desirable Condor Manor community. Offering 2,016 square feet, 4 bedrooms, 2.5 baths, and a two-car garage, this home combines modern finishes, energy-efficient construction, and the outdoor space today’s buyers are looking for. Step inside to a bright, open first floor featuring durable luxury vinyl plank flooring and plenty of room for everyday living and entertaining. The kitchen is the heart of the home with granite countertops, stainless steel appliances, and 42” American Woodmark cabinetry. Two generous living areas and a dining space provide flexibility for entertaining, relaxing, a home office, or play space, with peaceful views of the backyard. Upstairs, upgraded wall-to-wall carpeting creates a comfortable retreat. The spacious primary suite features a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide plenty of room for family, guests, hobbies, or office space. Built with efficiency and convenience in mind, the home features enhanced insulation, Low-E windows and doors, energy-efficient mechanical systems, and a conditioned crawl space. The two-car garage is pre-wired for electric vehicle charging, and the large driveway provides ample additional parking. Enjoy your morning coffee on the covered front porch or entertain on the 12’ x 16’ rear deck overlooking the expansive backyard. With a full acre, there’s room for pets, gardening, recreation, outdoor entertaining, and future projects—or simply enjoy having more privacy and breathing room. Located just outside the town of Church Hill with convenient access to Routes 213 and 301, Condor Manor offers a peaceful Eastern Shore setting while keeping commuting routes within easy reach. Newly built. One full acre. Four bedrooms. Move-in ready. And now offered at a great new price. Schedule your private showing and see the value this home has to offer. This community consists of 26 homes/lots . NOTE: At the time of listing, the calculated taxes reflect the assessment on the property and do not yet include the newly built home/improvements. Buyers should verify future tax assessments.

334 Eagle Manor Dr, Church Hill

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

408 Butlers Lndg, Stevensville
$1,150,000
3 Beds ⋅ 3 Baths
NEW PRICE! A recent appraisal supports the list price, so you can buy with confidence. Don’t miss this opportunity to live on the water in a beautiful neighborhood! Tucked between the tranquil waters of Long Creek and Shipping Creek, this approximately 2,100 square-foot waterfront retreat offers a rare blend of mid-century charm and modern comfort. With two bedrooms, an office and three full bathrooms, there’s plenty of space to live, relax, and host with ease. Originally built in 1977 and thoughtfully renovated in 2019, the home showcases timeless mid-century design — clean lines, an inviting flow, and character you can’t replicate in new construction. A brand-new well pump (2025) adds peace of mind, ensuring reliable, efficient water service for years to come. The primary bedroom offers a true private retreat, while the additional bedrooms and full baths provide comfort and flexibility for family or guests. Throughout the home, updated finishes and smart design touches create a space that feels both stylish and easy to live in. Step outside and the real magic begins: your own private dock on Long Creek, with a mean depth of approximately 6 feet, ideal for kayaking, paddleboarding, fishing, or simply pulling up the boat after a day on the water. Enjoy the birds, sea life and mature landscaping from morning to night! This is more than a house — it’s a lifestyle. Mid-century character, recent upgrades, and an unbeatable waterfront setting come together to create a truly special place to call home. One small thing: with two bedrooms total, “the additional bedrooms” in the third paragraph reads as plural. You might change it to “the second bedroom, office, and full baths” so it matches the bedroom count.

408 Butlers Lndg, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

414 Bay Dr, Stevensville
$2,769,900
5 Beds ⋅ 8 Baths
Finally Finished***From March 2026 until August 2026 the home went through its final finishing touch stages. There have been recent upgrades including water and electric to the pier.***Designed by YSA Homes and Simply Wesley Interior Design of Annapolis, this extraordinary brand-new modern coastal farmhouse style smart-home offers over 6,148 square feet of thoughtfully designed living space, where every tile throughout the home was handpicked and expertly curated using top-of-the-line luxury selections. The kitchen is outfitted with premium, top-tier appliances including Wolf, creating a seamless blend of elevated craftsmanship, timeless design, and modern functionality at every turn. The property is permitted for a pool to be built. This stunning residence features five oversized bedrooms, each with their own expansive en suite bathrooms, and three of the five have waterfront bay views. Totals include six full bathrooms, two half bathrooms, five gigantic bedrooms, 2 car oversized attached garage with rear entry door. An owner’s suite on the main level (with huge custom closet) provides everyday convenience, while the second level includes an additional  owner’s suite with a massive custom walk-in closet, ideal for multi-generational living or extended guest stays. Upon entering the home, you are welcomed into an open-concept main level where the kitchen flows seamlessly into the dining and living areas, creating an ideal setting for entertaining and everyday living. The living room is anchored by a striking wireless water vapor fireplace, offering modern ambiance without heat or emissions. A main-level half bath adds convenience, while the primary suite features a spa-inspired oversized bathroom with a soaking tub, a large European-style walk-in shower, and exquisite designer finishes throughout. The second level impresses with a spacious great room, complete with a wet bar and an additional half bath, opening to a large upper-level deck designed for optimal water views and entertaining. Four generously sized en suite bedrooms are located on this level, two of which showcase stunning water views through oversized windows, filling the space with natural light. The lower level offers exceptional flexibility, featuring a walk-out basement with exterior sliding doors, a full bathroom, a dedicated laundry room, and ample space for a game room, den, home gym, or additional living areas. Ask the listing agent about available improvement and build-out options for the basement. Outdoor living continues on the main-level patio, with the option to expand or customize to suit your vision. ***The home features a brand new pier and a brand new well. Ask agent about shutter options. Washer- dryers on 2nd level and in basement (2 sets). Ask agent for 6th bedroom option to be included. Located on sought-after Kent Island, this home offers access to a true Chesapeake Bay lifestyle just approximately 20 minutes from historic downtown Annapolis. Nearby waterfront parks, marinas, beaches, and miles of scenic walking and biking trails along the Cross Island Trail. Golf enthusiasts will appreciate proximity to Blue Heron Golf Course with membership options available, as well as the nationally recognized Queenstown Harbor Golf Links featuring two championship courses. Residents can easily enjoy all that downtown Annapolis has to offer, including boutique shopping, waterfront dining, sailing culture, festivals, and the charm of the historic district and U.S. Naval Academy. Just minutes away, **Queenstown Premium Outlets. Kent Island is also home to waterfront dining, local crab houses, and Love Point Vineyards, while Terrapin Nature Park and Matapeake Beach offer stunning Chesapeake Bay views. Conveniently positioned for commuting to Baltimore and Washington, D.C., this location blends coastal living with everyday accessibility. This is not just a home, this is a coastal lifestyle.

414 Bay Dr, Stevensville

Listing courtesy of Cummings & Co. Realtors. Contact:

105 Night Heron Ct, Stevensville
$1,675,000
3 Beds ⋅ 4 Baths
105 Night Heron is a substantially expanded and renovated home offering more than 4400 square feet of finished living space plus an additional 850 square feet of finished, conditioned, multi-purpose garage space. The property features expansive water views and numerous high end finishes including custom Omega cabinetry, granite and black walnut countertops, extensive built-ins, premium Miele, Viking and Sharp appliances, hardwood and limestone flooring, Kohler fixtures, a custom coffered bar-room ceiling, a 500-bottle wine storage room, and extensive recess lighting. The main floor boasts a dream kitchen with breakfast area and fireplace and a formal dining room off the foyer with designer lighting that is included in the sale. A bar and billiards room has custom cabinetry, a pool table and seating area with fireplace, and views of Eastern Bay. Also on this floor is a formal living room with fireplace, a home office with Bay views, and a large mud-laundry room with adjoining powder room. The large primary suite has 3 closets in the bedroom area as well as a walk in closet and dressing room with custom cabinetry and natural light. The large primary bath has custom cabinetry with lots of storage, a separate tub and shower, dual sinks, limestone floors and a separate water closet. The second floor loft opens to two more bedrooms and a shared bath. One of the bedrooms leads to a veranda with stone fireplace and sweeping views of Eastern Bay. Appliances include a Miele refrigerator and freezer, Viking gas range, dishwasher, microwave, warming drawer, beverage and wine coolers, washer and dryer, garage refrigerator and beverage station and a Napoleon outdoor grill. Televisions and sound bars located in the bar area, club room, second floor loft and kitchen are included in the sale. The garage includes two Lift Master garage door openers, two SunPro motorized screens and RaceDeck flooring. Cove Creek Club is situated on 334 acres of large home sites with beautiful landscaping and views of Eastern Bay. Amenities include a USGA rated golf course, a private marina with direct access to Eastern Bay, boat ramp and storage yard, a private sandy beach, tennis, basketball and bocce ball courts, a club house and event facility, pro shop, walking and biking trails, and an exercise facility. It is conveniently located to Annapolis, Baltimore, Washington DC and Philadelphia.

105 Night Heron Ct, Stevensville

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

405 Rings End Rd, Millington
$400,000
3 Beds ⋅ 2 Baths
Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. NOTE: Manufactured home with skirting-- without a foundation- so it may impact financing approvals. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend retreat, full-time residence, recreational getaway, or potential future waterfront homesite, this property offers plenty of possibilities. Convenient access to US Route 301 provides easy travel to Delaware and surrounding Eastern Shore communities. Enjoy 7.19± acres of Chester River waterfront with hunting, fishing, and boating opportunities on Maryland’s Eastern Shore.

405 Rings End Rd, Millington

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

124 Wilton Rd, Chestertown
$294,900
3 Beds ⋅ 1 Baths
MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor and Queen Anne’s County school district. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis water system in the kitchen. Numerous updates have been completed recently, including new LVP flooring, carpet, light fixtures, a new roof in 2020, new windows in 2021, new exterior and entry doors in 2023. Perfect location for dog lovers with a recently added split-rail fence enclosing the backyard. Walking distance to Round Top Park and minutes from Downtown Chestertown where you can enjoy local restaurants, shops, waterfront attractions, the dog park and the popular farmers market every Saturday! Don't miss this opportunity to make this wonderful property your new home!

124 Wilton Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

14 Fairway Is, Grasonville
$899,000
5 Beds ⋅ 3 Baths
Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and community—all just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 10th green. Situated on a one-acre lot, the home offers over 3,000 square feet, 4–5 bedrooms, a three-car garage, and a comfortable, flexible floor plan designed for everyday living and entertaining. A dramatic two-story foyer leads to bright living spaces accented by tray and vaulted ceilings. The spacious kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, and opens to the family room with bamboo flooring, gas fireplace, custom built-ins, and access to the large deck. A separate dining room and main-level bedroom add versatility. The spacious primary suite offers a large walk-in closet and private bath with soaking tub, dual vanities, and walk-in shower. Enjoy beautiful golf course views from the deck or screened gazebo—perfect for relaxing, entertaining, or an Eastern Shore crab feast.

14 Fairway Is, Grasonville

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

108 Blenny Ln, Chester
$364,900
3 Beds ⋅ 3 Baths
Owner Says Sell! Newly Reduced Price * Bayside Condo Townhomes in Chester * Kent Island - Located in the Popular Community of Bayside just minutes from the Bay Bridge, Castle Harbor Marina for Boaters and all -Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground, so all rooms have windows and the ground floor is a level walk out. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space. The community of Bayside is a waterside community and conveniently located near Castle Harbor Marina which is a privately owned marina and within walking distance of this townhome. It has public water, public sewer, propane gas for fireplaces and is serviced by Breezeline & Talkie for Internet and Cable. The community amenities include Outdoor Pool + Hot Tub w Lifeguard, Clubhouse with Exercise Room, Upper-Level Party/Meeting Room, Tennis, Volleyball. It has an On-Site Property Manager. The community fees include: grass cutting, snow removal, roof, siding, decks, trash & recycle.

108 Blenny Ln, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

624 Davol Rd, Stevensville
$565,000
4 Beds ⋅ 4 Baths
Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access to nearby trails, shopping, dining and everything Kent Island has to offer. Coming soon — stay tuned for your opportunity to see this spacious, updated Cloverfields home!

624 Davol Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

Parcel 73 Parcel 73 Barclay Road, Barclay
$85,000
7.5-Acre Residential Lot for Sale in Barclay Enjoy the peace and privacy of country living with the convenience of small-town amenities nearby. This approximately 7.5-acre residential lot is located just outside the town limits of Barclay, offering the benefit of no town property taxes. The property does not have access to public water or sewer. A private well and an approved perc test or other suitable private septic solution will be required prior to development. No perc test has been applied for. Buyer is responsible for conducting their own due diligence regarding zoning, building requirements, well and septic feasibility, and all other matters related to the property’s potential use and development. With a quiet setting and convenient access to major commuting routes, this property offers an excellent opportunity to create your own private homesite while enjoying the charm of small-town living.

Parcel 73 Parcel 73 Barclay Road, Barclay

Listing courtesy of Benson & Mangold, LLC. Contact:

2006 Bennett Point Rd, Queenstown
$1,500,000
4 Beds ⋅ 3 Baths
Spectacular Waterfront Retreat on almost 7 Acres in Exclusive Bennett Point! Welcome to your private paradise on the shores of serene Greenwood Creek! This extraordinary waterfront estate offers almost 7 acres of pure tranquility and luxury, surrounded by water on two sides for a true feeling of seclusion and peace. Your deep-water private pier is a boater’s dream — complete with 3 boat lifts and 2 jet-ski lifts ($150k value just in lifts alone)— perfect for crabbing, fishing, or setting out for a sunset cruise. The home’s Royal Blue Terracotta roof and accents make a bold architectural statement, while the full wrap-around deck ensures you’ll never miss a moment of the breathtaking waterfront views. Step inside and be transported to a stunning waterfront chalet (2x6 construction), where soaring ceilings, skylights, and warm wood accents create a cozy yet grand, open atmosphere. The nearly 3,000 sq. ft. of living space includes a magnificent 35’ x 17’ great room anchored by a floor-to-ceiling stacked-stone fireplace with a wood stove—powerful enough to heat the entire home! The open-concept of the great room, dining and kitchen areas make entertaining a joy. Kitchen features custom cabinetry, granite countertops, a beverage fridge, island, and ample dining space—flowing seamlessly to the screened porch and wrap-around decking. This home also enjoys over 2 thousand ft of heating tubes under the floor for warm-radiant heating you won't find anywhere else! The main level offers 3 spacious bedrooms, 2 full baths, and convenient laundry and storage areas. Upstairs, the cozy loft-style family room with skylights overlooks the great room and leads to a luxurious 25’ x 23’ primary suite, complete with a spa-inspired bath featuring dual sinks, a whirlpool tub, separate shower, and skylights that fill the space with natural light. Every inch of this home was designed to celebrate waterfront living at its finest—a place where comfort meets adventure, and every day feels like a getaway. 🌅 Don’t wait—this rare Bennett Point gem won’t last long!

2006 Bennett Point Rd, Queenstown

Listing courtesy of RE/MAX Executive. Contact:

1520 John Brown Rd, Queenstown
$749,000
3 Beds ⋅ 2 Baths
Welcome to your own private Eastern Shore retreat! Nestled on approximately 17.6 picturesque acres, this charming property offers the perfect blend of peaceful country living and everyday convenience. The home features comfortable one-level living with spacious gathering areas, a cozy wood stove, and beautiful views of the surrounding countryside. Whether you’re looking for room to garden, hunt, farm, enjoy outdoor recreation, or simply relax and take in the tranquility, this property provides endless possibilities. The expansive acreage offers privacy, open space, and the opportunity to create the lifestyle you’ve been dreaming of while still being just a short drive to shopping, dining, and major commuter routes.

1520 John Brown Rd, Queenstown

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

214 Bayberry Dr, Chester
$874,000
3 Beds ⋅ 3 Baths
Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney 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 in a den setting. The Gourmet Kitchen is special, 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. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. 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.

214 Bayberry Dr, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

259 Topside Dr Unit 166, Stevensville
$650,000
3 Beds ⋅ 3 Baths
Welcome to 259 Topside Drive in Bay Bridge Cove, one of Kent Island’s most sought-after 55+ communities! This beautifully upgraded Oxford model offers the spacious, flexible floor plan buyers love, paired with a premium setting overlooking the community pond and fountain. Step inside to an open and inviting main level designed for both everyday living and entertaining. The gourmet kitchen is a standout, featuring beautiful light gray cabinetry, a custom backsplash that complements it perfectly, an upgraded appliance package, generous workspace and an easy flow into the main living areas. A cozy fireplace anchors the living room, while the expanded double sunroom fills the rear of the home with natural light and creates even more space to relax, entertain or simply enjoy the view. Step outside onto the deck and take in peaceful pond and fountain views—the perfect backdrop for morning coffee, an evening glass of wine or unwinding at the end of the day.The Oxford’s flexible design continues upstairs, where you'll find an additional bedroom and full bath along with a spacious loft and separate den featuring built-in shelving. Whether you need private guest accommodations, a home office, hobby space, reading room or an additional living area, this second level gives you options without sacrificing the convenience of main-level living. Located in the heart of Stevensville on Kent Island, Bay Bridge Cove offers an active, low-maintenance lifestyle with a clubhouse, fitness center, outdoor pool, recreational courts, walking and biking trails, and plenty of opportunities to connect with neighbors—all just minutes from shopping, dining, waterfront recreation and the Chesapeake Bay Bridge. This isn’t just an Oxford—it’s an Oxford with the upgrades, expanded living space and pond setting buyers wait for.

259 Topside Dr Unit 166, Stevensville

Listing courtesy of Samson Properties. Contact:

118 Broadwater Dr, Chester
$645,000
2 Beds ⋅ 2 Baths
Welcome to Resort-Style Living at Four Seasons at Kent Island! Why wait for new construction when you can move right into this beautifully upgraded Donegal model with the sought-after Great Room extension? Offering exceptional value, this is currently the lowest-priced single-family home in the community, making it an outstanding opportunity to enjoy one of Maryland’s premier 55+ active adult neighborhoods. Designed with both elegance and everyday comfort in mind, this home features a stunning Gourmet Kitchen highlighted by a large Quartz Island, premium Gourmet Appliance Package with Double Oven, and abundant workspace—perfect for everything from casual breakfasts to holiday entertaining. The open-concept Great Room creates an inviting gathering place, centered around a warm Gas Fireplace, while upgraded lighting throughout the home adds a sophisticated touch. The Luxury Spa Bath offers a private retreat after a busy day, and Quartz vanities in every bathroom provide both beauty and durability. The thoughtfully designed floor plan includes first-floor bedrooms, allowing comfortable one-level living. A dedicated home office on the main level provides an ideal workspace, hobby room, or can easily function as a third bedroom for visiting family and friends. Additional premium features include elegant Plantation Shutters, an oversized two-car garage with generous storage space, and an underground irrigation system that helps keep your lawn lush while minimizing maintenance. With approximately $89,000 in builder upgrades and options, this home offers exceptional quality and value that would be costly to duplicate today. Come experience the carefree lifestyle of Four Seasons at Kent Island, where resort-style amenities, beautiful surroundings, and a vibrant social atmosphere make every day feel like a vacation. Life in Four Seasons at Kent Island is about more than the home itself. Residents enjoy resort-style amenities including a stunning clubhouse, indoor and outdoor pools, fitness center, pickleball courts, walking trails, kayak launch, fishing pier, and an active social calendar designed for a vibrant lifestyle.

118 Broadwater Dr, Chester

Listing courtesy of RE/MAX Executive. Contact:

1107 Oyster Cove Dr, Grasonville
$759,000
3 Beds ⋅ 4 Baths
One of the BEST VIEWS in Oyster Cove! WATERFRONT VIEWS from almost every room! This beautiful, gated community at the Kent Narrows Bridge greets you with scenic entrance ponds and fountains. You feel like you are on vacation while you are working from your home office in this tranquil setting. Grill on your spacious deck while entertaining friends and watching boats heading to St. Michaels/Annapolis, etc. Freshly painted throughout with 3 bedrooms/3.5 baths. Hardwood floors are featured on the 1st/2nd floors plus a TV, FP w/electric insert and built-ins. The updated, eat-in country kitchen features granite counters, beadboard bar and white cabinetry. Waterfront primary suite has a balcony, barn doors, W-I shower, W-I closet and jacuzzi. Utility room is equipped with newer, front-loading washer/dryer. Enjoy the large deck with remote-controlled awning and gate. HWH and W/D 2022. Roof/siding 2019. HVAC 2018. Boat slips available for rent/sale, along with 5 visitor slips for your boating friends. Enjoy the 1.5 mi. WATERFRONT walking path and the beautiful clubhouse w/state-of-the-art gym, full kitchen, holiday parties and monthly socials, game nights, etc. Saltwater pool opens at 6AM so you can enjoy a swim before the heat of the day. Dock your boat in 1 of the 2 marinas where slips range from 35' - 60'. Use the convenient launch pad for your kayak where there is space for > 100 kayaks or take advantage of the 10 jet ski ports. Enjoy a bike ride on the nearby, paved Cross Island Trail from Oyster Cove to the Chesapeake Bay, Romancoke and Long Point Rd. Convenient for dog walking, biking, jogging, etc. Walk to 5 restaurants. Only 20 minutes to Annapolis by car or a 30-minute boat ride to St. Michael's for lunch and shopping. Enjoy a round of golf at Blue Heron executive course or Queenstown championship course. Your dream house awaits you!

1107 Oyster Cove Dr, Grasonville

Listing courtesy of Star Realty. Contact:

620 Baxter Rd, Sudlersville
$569,900
3 Beds ⋅ 3 Baths
BEAUTIFULLY UPDATED HOME ON 3.34 ACRES WITH TWO IMPRESSIVE DETACHED BUILDINGS! Enjoy country living with exceptional space and versatility! This beautifully maintained custom-built 3-bedroom, 2.5-bath home features a completely renovated kitchen with white cabinetry, quartz countertops, and high-end stainless-steel appliances. New luxury vinyl plank flooring throughout and fresh interior paint give the home a bright, modern, move-in-ready feel. Relax on the welcoming front porch or screened rear porch overlooking the peaceful, private 3.34-acre setting. The spacious primary suite features a walk-in closet and private bath, while the partially finished, heated and cooled basement offers additional flexible living space. WHAT TRULY SETS THIS PROPERTY APART ARE THE TWO DETACHED BUILDINGS! A two-car garage is conveniently connected to the home by a breezeway, while the impressive 30' x 60' detached building offers incredible possibilities! Complete with 220-volt electric service, a workshop, storage loft, office, and spacious gathering/party room, this versatile building is ideal for car enthusiasts, hobbyists, craftsmen, entertaining, or anyone needing extra space for projects, vehicles, and equipment. Additional improvements include a newer HVAC system, new well pump with continuous pressure system, and added attic insulation. Conveniently located approximately 18 miles from Chestertown, Centreville, Dover, and Middletown, this exceptional property combines modern updates, country privacy, and outstanding detached building space that's hard to find! A MUST-SEE PROPERTY WITH SO MUCH MORE THAN JUST A BEAUTIFUL HOME!

620 Baxter Rd, Sudlersville

Listing courtesy of Taylor Properties. Contact:

209 Harrier Way, Chester
$737,900
4 Beds ⋅ 3 Baths
If you're looking for the ease of primarily one-level living with flexible space for guests and hobbies, 209 Harrier Way offers the best of both worlds.*** Seller offering $7500 toward closing costs. Agent offering a free home inspection and home warranty (buyer to select). Barely lived in and offering over $75,000 in builder upgrades, this home still feels like new, allowing you to move right in without the wait or additional costs of new construction (i.e. transfer tax split, etc). Designed for easy everyday living, the Simone model offers the convenience of having the majority of the home's daily living spaces on the main level. The gourmet kitchen, dining and living areas, screened porch, primary suite, second bedroom, office, full bath, and laundry are all thoughtfully located on the main floor. The stunning gourmet kitchen features crisp white cabinetry, a large center island, stainless steel appliances, wall oven/microwave combination, and propane gas range, flowing seamlessly into the light-filled dining and living areas. The living room is anchored by a cozy stone fireplace, while the screened porch provides a relaxing place to enjoy your morning coffee or unwind. The main-level primary suite features tray ceilings and a spa-inspired bath with dual vanities, a large walk-in shower, and an expansive walk-in closet. Upstairs, you'll find flexible bonus space including a spacious loft, two additional bedrooms, and a full bath, perfect for visiting family, hobbies, entertaining, or simply having extra space when you want it. **It's additional space when you need it, without requiring stairs for your everyday living.** The attached garage adds convenience and storage. Beyond the home, enjoy a resort-style lifestyle with incredible amenities including a 23,000-square-foot clubhouse, fitness center, indoor and outdoor pools, billiards, tennis and pickleball courts, community pier, outdoor bar, fire pit, and a full calendar of social activities. The nearby Cross Island Trail is perfect for walking, running, or biking, and you're just minutes from shopping, dining, and everything Kent Island has to offer.

209 Harrier Way, Chester

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

113 Bentons Pleasure Rd, Chester
$829,000
4 Beds ⋅ 3 Baths
A must see home! NEW LIST PRICE Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

1403 Marion Quimby Dr, Stevensville
$285,000
3 Beds ⋅ 2 Baths
Discover the charm of Thompson Creek Condos. This beautifully maintained 3-bedroom, 2-bathroom unit offers an inviting open floor plan, perfect for both relaxation and entertaining. Enjoy the warmth of an electric fireplace in the cozy living area, while the spacious eat in kitchen is equipped with essential appliances including a dishwasher and stacked washer/dryer. Step outside to your private balcony, where serene pond views create a tranquil retreat. The community boasts exceptional amenities, including a refreshing outdoor pool, a fitness center, and scenic jogging paths, ensuring an active lifestyle right at your doorstep. With sidewalks and street lights enhancing the neighborhood's charm, evening strolls become a delightful routine. Thompson Creek Condos is ideally situated near top-rated schools, lush parks, and essential public services, making it a prime location for convenience and community engagement. The association fee covers maintenance and insurance, allowing you to enjoy a worry-free lifestyle. Experience the best of both worlds-relaxation and recreation-within this vibrant community. Whether you're lounging by the pool or exploring the nearby river, this property offers a lifestyle that is both enriching and fulfilling. Don't miss your chance to call this stunning condo home!

1403 Marion Quimby Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact:

106 Pixie Ct, Grasonville
$599,900
5 Beds ⋅ 3 Baths
Please remove shoes or use shoe covers provided! Welcome to the rarely-available upgraded Hudson model at Perry's Retreat located at 106 Pixie Court. This beautiful unit offers the perfect blend of space, comfort, and modern design on a PREMIUM LOT. This home presents a rare opportunity to own one of the community's most desirable models in a cud-de-sac. The main level features an open concept design that seamlessly connects the kitchen, dining, and living areas, creating an ideal layout for both everyday living and entertaining. A private office with French doors provides the perfect work from home space, while an additional ensuite bedroom on this level offers endless possibilities as a guest room, or hobby space. The upgraded kitchen serves as the heart of the home, showcasing quartz countertops, stainless steel appliances, upgraded backsplash, additional wall oven, and a large island overlooking the spacious living room. Luxury vinyl plank flooring in most of the main level adds both style and durability. Upstairs, the spacious primary suite offers a relaxing retreat with a tray ceiling, two oversized walk-in closets, and a beautifully appointed en-suite bathroom featuring dual vanities, private water closet, and linen closet. Three additional bedrooms, a full bathroom with double sinks, and a convenient upper-level laundry room complete the second floor. Outside, enjoy a backyard that creates a setting for relaxation and entertaining. Community amenities include a playground, open green space for neighborhood events. Conveniently located just minutes from Route 50, residents enjoy easy access to Kent Island, Annapolis, Easton, St. Michaels, Oxford, Tilghman Island, Baltimore, and Washington, D.C. Directly across from the community, the Chesapeake Bay Environmental Center offers hiking trails, kayaking, wildlife viewing, educational programs, and summer camps, allowing you to fully embrace the Eastern Shore lifestyle. Professional photos coming soon!

106 Pixie Ct, Grasonville

Listing courtesy of HomeSmart. Contact:

116 Reeand Ln, Church Hill
$399,000
3 Beds ⋅ 3 Baths
Sellers willing to contribute seller help to fund a buyer’s 2-1 interest rate buydown! Buyers get the benefit of a lower mortgage payment the first 2 years! Dependant upon offer amount and or an "as-is" offer. Welcome home to this beautifully maintained Colonial nestled in the desirable Meadows community of Church Hill. Ideally located between historic Chestertown and Centreville and within the sought-after Queen Anne's County School District, this home offers the perfect blend of comfort, convenience, and timeless style. Step inside through the impressive two-story foyer that welcomes you into a bright and inviting floor plan. The spacious primary suite serves as a private retreat, complete with a, separate shower, and relaxing soaking tub. The home has been exceptionally well cared for and features numerous updates, including a newer roof and HVAC system, providing peace of mind for years to come. New HVAC system installed and serviced by Dixieland energy January 2025, operated by Nest technology. New Roof in July 2025 installed by Economy Roofing with GAF Timberline HDX Lifetime Shingles. New 16x12 Trex Deck with a large poured concrete patio installed in 2024-2025. The partially finished full basement offers endless possibilities with plenty of room for a recreation area, home gym, office, or additional storage. Outside, you'll fall in love with the beautifully landscaped backyard oasis—perfect for entertaining, summer barbecues, or simply relaxing after a long day. Square footage including basement is roughly 2700 sq feet. With its outstanding condition, thoughtful updates, attached garage, and prime location just minutes from shopping, restaurants, and easy access to Route 301, this is a home that truly checks all the boxes. Schedule your private showing today and experience everything 116 Reeand Lane has to offer! Some photos have had personal items removed and have been staged with AI.

116 Reeand Ln, Church Hill

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

200 Ackerman Dr, Stevensville
$589,999
4 Beds ⋅ 3 Baths
Experience coastal living at its finest in this stunning 2024-built home located in the sought-after Romancoke community, just steps from the Chesapeake Bay. This beautifully appointed 4-bedroom, 2.5-bath home offers the perfect combination of modern design, comfort, and convenience. The spacious open-concept floor plan is ideal for entertaining, featuring seamless flow between the living, dining, and kitchen areas. High-end custom window blinds add a touch of elegance throughout, while the fully fenced backyard creates the perfect private retreat for relaxing, hosting gatherings, or enjoying time with family and pets. Perfectly situated on a quiet private road, this home offers a peaceful setting with easy access to the bay, making it ideal for boating, fishing, kayaking, or simply enjoying breathtaking waterfront sunsets. Connected to public sewer and built in 2024, you'll enjoy the benefits of newer construction with the peace of mind that comes with modern systems and finishes. Don't miss this opportunity to own a like-new coastal retreat in one of Kent Island's most desirable waterfront communities!

200 Ackerman Dr, Stevensville

Listing courtesy of Rise Real Estate, LLC. Contact:

2200 Bennett Point Rd, Queenstown
$630,000
4 Beds ⋅ 2 Baths
Welcome to this beautifully maintained one-level rancher, perfectly situated on a private 1-acre lot. Offering 2,441 square feet of comfortable living space, this home provides 4 bedrooms, 2 full baths, and has an inviting open floor plan designed for everyday living and entertaining. Thoughtful architectural details, including coffered ceilings and heavy crown molding, add character and elegance throughout the main living areas. The spacious living room is anchored by a fireplace with a wood-burning insert, creating a warm and welcoming atmosphere. The well-appointed kitchen offers abundant cabinet and counter space and opens seamlessly to the main living areas. The dining area is spacious, ideal for hosting family and friends. A large four-season room, complete with heating and cooling, provides additional year-round living space and overlooks the lovely backyard. Step outside to enjoy the expansive deck and pergola-covered seating area, perfect for relaxing or entertaining. The fully fenced backyard offers plenty of room for outdoor activities while maintaining a sense of privacy. A detached two-car garage features a heated and cooled bonus room above, ideal for a home office, gym, hobby room, or additional flex space. Major improvements completed within the past five years include a newer HVAC system, roof, gutters, and kitchen updates, providing added value and peace of mind. This exceptional property combines the convenience of one-level living with modern updates, versatile spaces, and a peaceful setting—ready for you to call it home.

2200 Bennett Point Rd, Queenstown

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

111 Marshgrass Way Unit 41, Chester
$998,000
3 Beds ⋅ 3 Baths
Welcome to this stunning 4th floor penthouse Severn condominium with serene bay views! This end unit looks out over the walking trails to the water and trees. The fabulous community center /pool / pier is a short 1 mile walk from your backyard.! This unit also has the largest garage space in the the building, plenty of room for one car and storage, a refrigerator etc. There is also an additional inside storage room. This 2600 Sq Ft home is flooded with natural light and has numerous quality upgrades including custom shiplap in most of the rooms, custom ceiling fans and dining room light fixture, custom built his and hers walk in closets. The primary bath has upgraded tile, shelving for more storage, mulitple shower heads and back and front lit vanity mirrors. The gourmet kitchen is designed to impress, featuring elegant quartz countertops,premium appliances and a Wolfe induction cooktop. The island has been upgraded with shiplap as well. Thoughtful upgrades continue throughout the entire home with custom blinds with remote control, a gas fireplace,9 FT ceilings with tray ceilings in the living room and primary suite. A wet bar has also been added to the dining area.The large primary bedroom comes complete with a sitting area/office with exceptional waterviews. It also offers custom designed his -and -her closets that provide both style and storage. This unique residence offers a peaceful setting where you can relax and enjoy the ever-changing waterfront vistas. Whether you are enjoying your morning coffee or entertaining guests, this home offers the perfect blend of sophistication, comfort, and low maintenance waterfront living. Residents enjoy an exceptional resort-style lifestyle with amenities that include indoor and outdoor swimming pools, a fitness center, clubhouse, library, billiards room, hot tub, Bocce Ball, pickleball and tennis courts, picnic areas, tot lots, and a community pier overlooking the Chester River. Ideally located just minutes from shopping, dining, golf, marinas, and the Chesapeake Bay Bridge, this exceptional waterfront residence offers the perfect blend of luxury, convenience, and carefree Eastern Shore living.

111 Marshgrass Way Unit 41, Chester

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

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