Chester MD Real Estate & Homes for Sale

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Beds:
3
Baths:
4.00
Sq.Ft.:
2,930
Status:
Active
MLS#:
MDQA2015636
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. 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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,789
Status:
Active
MLS#:
MDQA2015634
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace, and professionally designed details such as a feature wall, crown molding, and sliding barn doors that add custom character to each space. As an added benefit, all model home furniture is included, providing a fully move-in-ready experience. The gourmet kitchen is equipped with a Profile range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, elegant pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a clean, cohesive finish. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 and the loft for added comfort. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a spa-inspired retreat designed for everyday ease. For a full list of included features, please contact our sales representatives. 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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,993
Status:
Active
MLS#:
MDQA2015632
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a screened patio ideal for indoor–outdoor living. Elevated design moments—such as feature walls, ceiling beams, and barn doors—bring custom flair to each space. As a true bonus, all model home furniture is included, offering a completely move-in-ready experience. The chef-inspired kitchen showcases a Café range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, stylish pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a cohesive, upscale look. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 for added warmth. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a comfortable and functional retreat. For a full list of included features, please contact our sales representatives. 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.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,225
Status:
Active
MLS#:
MDQA2015638
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication. Standout features include a dedicated home office, an inviting fireplace, and a screened patio perfect for indoor–outdoor living. Custom design elements—such as barn doors, ceiling beams, and a striking feature wall—bring warmth, character, and craftsmanship to every corner. As a premium bonus, all model home furniture is included, providing a fully move-in-ready lifestyle. The chef-inspired kitchen showcases a Profile range, single oven, microwave, range hood, dishwasher, French door refrigerator, elegant pendant lighting, and a stylish tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a clean, cohesive look. Hardwood flooring spans the main level for timeless appeal, with tile in all full baths and carpet in Bedroom 2, the loft, and Bedrooms 4 and 5 for added comfort. The owner’s bath features a luxurious shower with a built-in seat, handheld shower wand, and double sinks—creating a serene, spa-like retreat. For a full list of included features, please contact our sales representatives. 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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,993
Status:
Active
MLS#:
MDQA2015498
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The To Be Built Home offers effortless single-level living with thoughtful spaces designed for both comfort and style. Featuring 2 bedrooms, 2 baths, and a 2-car garage, this home blends functionality with refined details throughout. A private home office provides the perfect space for productivity, while the stylish kitchen—complete with a large center island and spacious pantry—flows seamlessly into the great room, ideal for entertaining or relaxing. Sliding doors open to a covered patio, extending your living space outdoors. The luxurious primary suite features an oversized walk-in closet and a palatial bath with split vanities for a truly spa-like retreat. A convenient HovHall off the garage helps keep the home organized and clutter-free, enhancing everyday ease. 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.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,076
Status:
Active
MLS#:
MDQA2015460
Type:
Condo
Subdivision:
Bayside
Year built:
2001
Courtesy: TTR Sotheby's International Realty 410-673-3344
View additional info

ADDITIONAL INFORMATION

This beautifully maintained 3-bedroom, 3.5-bath marina-front townhouse with a 1-car garage offers the perfect blend of comfort, convenience, and Chesapeake lifestyle. Ideally located in the heart of Kent Island, you’ll enjoy stunning marina and Chester River views from multiple levels. The main floor features new luxury vinyl plank flooring, an open-concept kitchen, dining, and family room, and a gas fireplace. French doors open to a private deck where you can relax and watch the boats go by. Upstairs, the primary suite includes a walk-in closet, a spa-like bath with a jetted tub and separate shower, and a private balcony overlooking the water. A second bedroom on this level offers its own en-suite bath and new carpet throughout. The third-floor loft bedroom is a serene retreat with a closet, full en-suite bath, and sweeping marina views. The Bayside community offers resort-style amenities including a clubhouse, fitness center, pool, and tennis courts. Plus, Castle Marina is just steps away—keep your boat right out your back door and enjoy easy access to the Chester River and beyond. Experience low-maintenance, waterfront living at its best on Kent Island!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,550
Status:
Active
MLS#:
MDQA2014682
Type:
Condo
Subdivision:
Queens Landing
Year built:
1993
Courtesy: Taylor Properties 301-970-2447
View additional info

ADDITIONAL INFORMATION

Accepting backup contracts! Enjoy resort style living every day in the gorgeous waterfront condo. Watch the sun & moon rise as you sip your favorite beverage. This sought after townhome/condo has extensive view of the Chester River & Eastern Neck Island. The owner has updated & made this place like no other. Soundproof quiet rock, custom barn doors throughout, gourmet kitchen with granite counters, soft close maple cabinets, Acacia wood floors, newer HVAC, remote full blind for back windows (heat & light senses), custom plantation blinds, bathrooms boasts stone walls, custom ceramic, jacuzzi tub, walk in shower, keypad entry door, remote awning that senses wind, hardscapes to enjoy the views and so much more! The cross island bike/hike trail is nearby along with restaurants, medical and shopping. Come check out this amazing place! All reasonable offers considered.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,791
Status:
Active
MLS#:
MDQA2013574
Type:
Condo
Subdivision:
Bayside
Year built:
1992
Courtesy: Realty Navigator 410-643-3404
View additional info

ADDITIONAL INFORMATION

Experience Autumn Serenity on the Waterfront Discover the perfect blend of coastal charm and modern luxury this fall in this rarely available, oversized end-unit townhome — ideally positioned to capture tranquil marina views from your upper and lower decks. Step inside and enjoy the glow of the season with brand-new luxury vinyl plank flooring, a remodeled gourmet kitchen with quartz countertops and new appliances, and an inviting open layout filled with natural light. The primary suite offers a peaceful retreat with a fully renovated spa-style bathroom, while the other baths have been thoughtfully refreshed as well. Whether you’re sipping morning coffee as the autumn sunrise reflects off the water, or hosting friends on crisp evenings overlooking the boats in the marina, this home offers the perfect backdrop for the season. Bayside isn’t just a community — it’s a lifestyle. Residents enjoy resort-style amenities including a clubhouse, outdoor pool, fitness center, tennis courts, volleyball, and scenic walking and jogging trails framed by changing leaves and coastal breezes. Located just steps from Bayside Marina and within walking distance to waterfront dining, local shops, and cozy cafés, you’ll love the convenience of island life — all just minutes from the Chesapeake Bay Bridge for easy access to Annapolis, D.C., or Baltimore. Whether you’re seeking a full-time residence or a weekend waterfront escape, this home captures the essence of Kent Island living in every season — and fall is the perfect time to make it yours. ?? Schedule your private tour today and experience the comfort, beauty, and lifestyle this waterfront gem has to offer. ONE YEAR HOME WARRANTY FOR THE BUYER

Beds:
3
Baths:
2.00
Sq.Ft.:
1,250
Status:
Active
MLS#:
MDQA2015496
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.28 Acres
Year built:
2025
Courtesy: Coldwell Banker Waterman Realty 410-643-5005
View additional info

ADDITIONAL INFORMATION

New home being built! Act now and pick all your colors! Finished models can be seen! Call agent for details.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,073
Status:
Active
MLS#:
MDQA2014614
Type:
Condo
Subdivision:
Bayside Marina
Year built:
2000
Courtesy: TTR Sotheby's International Realty 410-673-3344
View additional info

ADDITIONAL INFORMATION

Welcome to this bright and inviting 2-bedroom, 2-bathroom lower-level end unit condo, ideally located in a desirable water-oriented community on Kent Island! The open living and dining area flows seamlessly into a galley-style kitchen with a breakfast bar, now updated with new granite countertops and a new stainless steel stove. The Primary suite is your private retreat, complete with a walk-in closet and a brand-new custom spa-like shower in the en-suite bath. A second bedroom and full bath provide plenty of space for family, guests, or a home office. Updates within the past few years include laminate flooring in the living areas, hallway, and baths, fresh carpet in both bedrooms and the primary closet, a modern interior paint palette, plus a newer HVAC, refrigerator, and microwave for added comfort and peace of mind. Bayside residents enjoy resort-style amenities such as a pool, tennis courts, fitness center, and clubhouse with a large party room. The unaffiliated Queens Landing Marina—just steps away—keeps your boat close, while the scenic Kent Island Trail offers miles of walking, jogging, and biking. All of this adds to the relaxed, vacation-like lifestyle of Maryland’s beautiful Eastern Shore!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,583
Status:
Active
MLS#:
MDQA2014400
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.14 Acres
Year built:
2021
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

10K price reduction!!! Better Than New – $175K+ in Upgrades and Lifestyle Ready Now Four Seasons at Kent Island – Killarney with Loft Model Why wait months—and spend thousands more—for a base-level new build when you can move into your dream home today? This beautifully enhanced Killarney with Loft model in sought-after Phase I delivers over $100K in builder upgrades plus $75K in custom renovations—a total investment of $175K+—all included. To replicate this home new through the builder would exceed $1 million. For added peace of mind, the sellers are including a two-year full-service home warranty, and an invisible fence is already installed and included. Exceptional Interior & Outdoor Living The gourmet kitchen is a showstopper with a 10’ white quartz island, dry bar, SMART stainless appliances, InstaHot water dispenser, and walk-in pantry. A marble-mantled electric fireplace anchors the open-concept living area and flows to the builder-upgraded screened porch overlooking a private backyard retreat. Entertain year-round on the expansive 40' × 15' paver patio with built-in gas fire pit, gas grill, and wood-burning pizza oven—all part of the $175K+ in thoughtful upgrades that make this home truly turnkey. The spa-inspired primary suite features a fully renovated bath (2025) with new flooring, lighting, towel warmer, and upgraded fixtures. Additional highlights include Pinnacle concrete coatings on the front and screened porches, a new front door, $5K+ in custom window treatments, all-new main-level lighting, a guest en-suite, and a loft with third bedroom and full bath. A Community & Lifestyle Second to None Four Seasons at Kent Island offers a 24,000 sq ft waterfront clubhouse with indoor and outdoor pools, a fitness center, yoga studio, game room, library, tiki bar, and outdoor amphitheater. Lighted pickleball and tennis courts, bocce, a dog park, a pier with transient slips, 4+ miles of walking trails, and direct access to the Cross Island Trail complete the resort experience. A full-time lifestyle director curates events from crab feasts and live music to holiday gatherings and fitness classes. The Smarter Choice: Waiting vs. Ready Skip construction delays, surprise upgrade costs, and months of dust and noise. This home is fully finished, beautifully landscaped, and move-in ready now. Proven resale strength in an established section of the neighborhood protects your equity and provides quiet streets and friendly neighbors from day one. This is the definition of turnkey luxury—offering comfort, style, and an unmatched Chesapeake Bay lifestyle today. Schedule your private showing and experience why this home is truly better than new.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,035
Status:
Active
MLS#:
MDQA2014832
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.32 Acres
Year built:
1975
Courtesy: Taylor Properties 301-970-2447
View additional info

ADDITIONAL INFORMATION

REDUCED! Opportunity Knocks Welcome to Harbor View on Kent Island - Just 7 minutes from the Bay Bridge This oversized ranch style home boasts 4 Bedrooms and 2 Full baths and is located just one block from Cox Creek. The open concept floor plan features a formal living room, large main level bedroom, hardwood flooring throughout, a modern kitchen with ample cabinetry, center island, extra counter spaces and stainless appliances. Relax in the spacious and cozy extra family room with fireplace, hearth and convenient built-ins. The adjacent spare room is the perfect spot for a home office or gym and the home is equipped with a separate convenient laundry/mudroom. Plenty of parking for family and guests in the 5 car driveway. Harbor View offers easy access to great area amenities, recreation, waterfront dining and more.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,634
Status:
Active
MLS#:
MDQA2014660
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.21 Acres
Year built:
2024
Courtesy: TTR Sotheby's International Realty 410-280-5600
View additional info

ADDITIONAL INFORMATION

Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front porch and charming curb appeal set the tone for what awaits inside. The grand two-story foyer opens to soaring ceilings, wide plank wood flooring, and light-filled spaces dressed in timeless plantation shutters. The main level is designed for easy living, with 10-foot ceilings that create a sense of openness and flow. At the heart of the home, the great room features cathedral ceilings, crown molding, and a gas fireplace, providing a warm gathering place for both intimate evenings and lively entertaining. The designer kitchen blends beauty and function with a large island, stainless steel appliances, a gas range, backlit cabinetry, and a beautifully lit backsplash that adds a touch of sophistication. The open-concept design extends into the breakfast area, making mornings and casual meals a delight. A screened-in porch and fenced patio create a seamless transition from indoor living to outdoor enjoyment, perfect for entertaining or simply savoring quiet moments surrounded by nature. The first-floor primary suite is a true retreat, complete with a spacious walk-in closet outfitted with built-ins and a spa-inspired bath designed with relaxation in mind. A second bedroom with its own private bathroom on the main level offers comfort and privacy for family or overnight guests, while a dedicated office provides the flexibility to work from home with ease. The convenience of a mudroom with built-ins and a first-floor laundry adds to the thoughtful design of this home. Upstairs, a large loft-style living area can serve as a media or game room, offering additional space for recreation, relaxation, or hobbies, while two generously sized bedrooms share a well-appointed bathroom. A large two-car garage with an extra storage and workshop area provides ample space for all your needs—including the perfect spot to store multiple kayaks. Every detail of this home has been carefully curated, from the crown molding to the custom finishes, creating a space that feels both refined and welcoming. Beyond the home itself, life at Four Seasons at Kent Island offers an unparalleled resort-style experience. Residents enjoy exclusive access to the Chester House Clubhouse, where a ballroom, bar and lounge, gathering spaces, and a demonstration kitchen set the stage for community and celebration. Fitness and wellness are at the forefront with indoor and outdoor pools, a state-of-the-art fitness center, yoga room, and walking paths. Outdoor amenities abound, from tennis, pickleball, and bocce courts to a kayak launch, fishing pier, and dog park. Evenings can be spent at the fire pit, tiki bar, or amphitheater, creating countless opportunities to connect with neighbors and enjoy the Chesapeake lifestyle. Perfectly situated on Kent Island, this home is more than just a place to live—it’s a way of life. Here, every day feels like a retreat, with the Chesapeake Bay as your backdrop and a vibrant community at your doorstep. Welcome to 132 Kestrel Lane, where luxury, comfort, and lifestyle meet.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2015436
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with tile in both full baths for easy maintenance. The owner’s bath features a walk-in shower with seat and handheld shower wand, double sinks, and elegant quartz countertops, 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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2015438
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with tile in both full baths for easy maintenance. The owner’s bath features a walk-in shower with seat and handheld shower wand, double sinks, and elegant quartz countertops, 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.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2015138
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly. Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric fireplace that adds warmth and ambiance. A dedicated home office with elegant lited French doors provides the ideal space for work or creativity. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all accented by quartz countertops that continue into the full baths. Enjoy laminate flooring throughout for easy maintenance, complemented by tile in the full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, plus double sinks and quartz counters for a spa-like retreat. For a full list of included features, please contact our sales representatives.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,610
Status:
Active
MLS#:
MDQA2015066
Type:
Single Family-Detached
Subdivision:
Castle Marina
Lot size:
0.51 Acres
Year built:
1974
Courtesy: Coldwell Banker Realty 410-263-8686
View additional info

ADDITIONAL INFORMATION

Move-in ready and full of upgrades, this thoughtfully designed home offers a bright, open layout perfect for everyday living and entertaining. The renovated kitchen features quartz counters, a coastal tile backsplash, and opens to the dining and living areas with soaring ceilings and access to the deck and fenced yard. The fire pit and mature landscaping makes for a private, serene setting. A private path through the backyard connects directly to Four Seasons and the Cross Island Trail—ideal for walking, biking, or enjoying the outdoors. The main level includes a bedroom and bonus room/office, while upstairs offers three additional bedrooms including a spacious primary suite with attached bath. Additional highlights include a two-car garage with extra storage, side gardens, tankless water heater, paved driveway with bonus parking, and no HOA. All this in a prime Kent Island location, just minutes to local shopping, dining, trails, and Rt. 50 for easy commuting to Annapolis, St. Michaels, Washington, D.C., Baltimore, and beyond. Don’t miss this opportunity to own a conveniently located, beautifully updated home in Castle Marina! Schedule your tour today - you won't want to miss this conveniently located and move in ready gem on Kent Island.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,791
Status:
Active
MLS#:
MDQA2014922
Type:
Single Family-Detached
Subdivision:
Bentons Pleasure
Lot size:
1 Acres
Year built:
2002
Courtesy: Wilson Realty & Staging LLC 410-304-2250
View additional info

ADDITIONAL INFORMATION

ATTENTION BUYERS: VA ASSUMABLE RATE of 2.49% AVAILABLE!! Discover the charm of this stunning Colonial home nestled in the desirable Bentons Pleasure neighborhood. With 2,791 sq. ft. of thoughtfully designed living space, this residence boasts four spacious bedrooms and 2.5 baths, perfect for both relaxation and entertaining. The well equipped kitchen invites culinary creativity, while the semi open floor plan seamlessly connects the dining and living areas, highlighted by a cozy fireplace. Enjoy the luxury of a soaking tub in the master bath and the convenience of walk-in closets. The home features beautiful wood floors and ceiling fans throughout, ensuring comfort year-round. Step outside to your private oasis, complete with a personal pool, ideal for summer gatherings or tranquil evenings. Located just minutes from commuter lots and an airport, this home offers easy access to local amenities, parks, and shopping. With a generous 1-acre lot and a side-entry garage, this property combines space, style, and convenience. Solar panels, too! Don't miss your chance to make this dream home yours!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
MDQA2014868
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

**** NICE VIEWS OF THE CHESTER RIVER**** ***** LOWEST PRICED SEVERN MODEL**** K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom, 2.5 bath end-unit boasting an expansive open floor plan with over 2600 square feet of luxurious living space. This home features a lavish gourmet kitchen and dining area, a huge great room with sliding door access to a large corner balcony. The centerpiece kitchen is equipped with GE Profile appliances and gas stove top. Also, quartz counters with under cabinet lighting, and oversized kitchen island. The fantastic owner's suite has an adjoining sitting room with access to the balcony, an owner's spa bath and 2 oversized walk-in closets. Two large secondary bedrooms are located in a separate wing of the home and each features a walk-in closet and share a Jack and Jill bath. There are 10 closets, and 18 windows. Additional features include a separate laundry room and powder room. Enhanced decorator details include luxury plank flooring, recessed lighting, a garage with adjoining driveway/parking space and a large personal storage room which is a few short steps from the elevator. ***** KEEP IN MIND THIS SEVERN MODEL, WITH OVER 2600 SQUARE FEET OF LUXURY LIVING SPACE, IS AVAILABLE TO YOU NOW. PRESENTLY, THERE IS A 6- 7 MONTH WAIT FOR THE COMPLETION OF NEWLY CONSTRUCTED SEVERN MODELS, BUT THIS UNIT IS MOVE-IN READY AT A MUCH LOWER PRICE WITH PLENTY OF HIGH-END DESIGNER FEATURES AND UPGRADES ALREADY INCLUDED***** Brand New 24,000 Square Foot Clubhouse with stunning Chester River Views! Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, electric and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, paved 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. Easy walk from this home to the Clubhouse. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

Beds:
4
Baths:
4.00
Sq.Ft.:
5,122
Status:
Active
MLS#:
MDQA2014738
Type:
Single Family-Detached
Subdivision:
Southwind
Lot size:
1.9 Acres
Year built:
1995
Courtesy: Long & Foster Real Estate, Inc. 410-721-1500
View additional info

ADDITIONAL INFORMATION

An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront residence on 1.9 acres boasting an enchanting open space floorplan. A first floor Ensuite BR has a walk-in closet plus a separate jacuzzi and shower in the updated full bath. The sumptuous approximately 39'X26' Primary Suite with a large sitting room area offers front and rear balconies specifically designed by the Architect to enjoy the breathtaking sunrises, moonrises & sunsets lighting the Bay with bright pink and orange skies and brilliantly lit sparkling water. This second floor Primary Suite has a Cathedral ceiling, a 3-sided gas fireplace and a fully renovated Coastal style bath which includes a luxurious remote controlled floating Air Spa tub. Also upstairs is a large loft accessed by French doors boasting custom built-ins and extraordinary extensive water views overlooking the Bay and Pool. Walls of windows throughout the residence provide abundant natural light and endless broad views of Crab Alley Bay from almost every room. The Gourmand's Kitchen with its solid custom maple cabinetry is furnished with a Subzero refrigerator, double wall oven with Smart features, auto purified cold water spigot at the sink along with a 5-burner gas cooktop. A Subzero wine fridge is located in the island by the Dining Room for easy entertaining. The hardwood flooring is Canadian White Maple. A freestanding curved White Maple staircase enhances the beauty of the very generously sized 2-story Foyer. A two-story Great Room features a 2-sided gas FP and a custom wet bar that both open to a vast Morning Room area and seating space. Formal separate Dining and Living Rooms are open via knee-walls with columns for romantic dining and entertaining. The level outdoor living space includes a lighted inground 36x18' pool, a Pergola and a stone hardscape with a built-in Grill, outdoor rated refrigerator and a built-in gas fireplace for chilly waterfront evenings outdoors. Plentiful terracing affords a breathtaking, serene setting to relax and entertain friends and family while taking in the extraordinary and expansive water views. There is a private pier, a 3-car garage with built-in overhead storage and a driveway that can accommodate several more cars and there are multiple landscaping berms. The home has a whole house sound system & whole house attic fan. The cooking, 3 fireplaces and 3 zone HVAC are propane. The community of Southwind is a waterfront peninsula surrounding 97 custom homes and offering a waterfront Clubhouse, Tennis Court, walking trails along the Bay, a Boat Launch and a gated boat storage area. Welcome home to your year-round vacation! Furniture negotiable

Beds:
2
Baths:
4.00
Sq.Ft.:
2,400
Status:
Active
MLS#:
MDQA2015626
Type:
Single Family-Detached
Subdivision:
Gibsons Grant
Lot size:
0.17 Acres
Year built:
2011
Courtesy: Coldwell Banker Realty 410-263-8686
View additional info

ADDITIONAL INFORMATION

Discover exceptional living on an oversized fenced lot in the sought-after community of Gibson’s Grant on Kent Island. This beautifully maintained home offers a rare combination of space, versatility, and thoughtful upgrades—inside and out. A welcoming front porch overlooks a peaceful community green space, setting the tone for the charm found throughout. Step inside to hardwood floors spanning the main level, where a cozy living room with a propane fireplace flows seamlessly into the open kitchen and dining area. The kitchen features stainless steel appliances, a pantry, and convenient access to the laundry room and main-level half bath. Just off the dining area, enjoy the three season room with EZ Breeze windows overlooking one of the neighborhood’s largest side yards—perfect for relaxing or entertaining. A standout feature of this property is the Finished Room Over Garage (FROG), complete with a walk-in closet, kitchenette, and full bathroom—ideal for guests, bonus living space, or a private office. Upstairs, the spacious primary suite offers comfort and convenience with an en-suite bath featuring a heat lamp, built-in wall jewelry storage, and a large glass-enclosed shower. An additional bedroom shares the hall bathroom with a jetted tub, and the upstairs loft—currently used as an office but easily convertible into a third bedroom—completes the upper level. Additional highlights include beautiful landscaping with irrigation, crown molding throughout, an oversized two-car garage, a full-home conditioned crawlspace with approximately 4-ft ceilings for ample storage, and a parking pad that accommodates 3+ cars. Gibson's Grant is one of the most desirable waterfront communities on the Eastern Shore, offering resort-style amenities including water access, an outdoor pool, clubhouse, fitness center, waterfront pavilion, kayak launch, pier, and direct access to the Cross Island Trail. Situated just off Route 50 yet tucked behind a peaceful nature preserve, Gibson's Grant is minutes away from local dining, shopping, and recreational activities. Experience the best of modern coastal living in a serene, private setting. Schedule your showing today and make this stunning home yours!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,399
Status:
Active
MLS#:
MDQA2015026
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.18 Acres
Year built:
2020
Courtesy: Real Broker, LLC - Annapolis 855-450-0442
View additional info

ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2014898
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

Introducing the Severn Lot 2224, projected to settle in May 2026. This thoughtfully designed home offers 3 bedrooms, 2.5 baths, and a 1-car garage. Interior highlights include a dry bar, electric fireplace, a spacious owner’s suite with a sitting room, and large walk-in closets. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, tile backsplash, and Quartz countertops. Laminate floors run throughout the home except for tile in the two full baths. The owner’s bath features a shower with seat, a handheld shower wand, double sinks, and quartz countertops for a luxurious touch. 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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,520
Status:
Active
MLS#:
MDQA2015440
Type:
Single Family-Detached
Subdivision:
Gibsons Grant
Lot size:
0.13 Acres
Year built:
2012
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Beautiful Home in Gibson’s Grant with Elevator, Open Floor Plan & Two-Car Garage Welcome to this beautifully appointed home in the sought-after waterfront community of Gibson’s Grant on Kent Island. This residence offers a perfect blend of comfort, style, and convenience — featuring a spacious open floor plan and an attached two-car garage. No need to worry about stairs — a full elevator effortlessly transports you to the grand second-floor primary suite, complete with a cozy sitting area and private porch. Throughout the home, you’ll find thoughtful upgrades, including a gourmet kitchen with granite countertops, hardwood floors, custom trim, and elegant finishes that make this property truly special. Enjoy the charm of the screened side porch, a beautifully landscaped English-style yard with brick patio, gardens, and fencing that provides both beauty and privacy. With three bedrooms and a den that can easily serve as a fourth bedroom or home office, this home offers versatile living space for any lifestyle. You’ll also enjoy peekaboo water views and the exceptional amenities that make Gibson’s Grant so desirable. Established in 2007, this 280-home community is nestled between the Chester River and Macum Creek, offering a community pool, clubhouse, fitness center, bocce court, pier, kayak launch, and playground and much more. Conveniently located near shopping, Starbucks, restaurants, the Kent Island Cross Island Trail, and just minutes from the Bay Bridge, this home offers the best of Kent Island living.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,789
Status:
Active
MLS#:
MDQA2015082
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, French door refrigerator, pendant lighting, and a stylish tile backsplash. Elegant quartz countertops extend through the kitchen and owner’s bath. Luxury vinyl plank flooring enhances the main level, with tile in all full baths and the laundry room, and plush carpet in the extra suite and upstairs loft. The owner’s bath features a spacious shower with a seat and handheld shower wand, plus double sinks for convenience. 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.

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Chester 21619 Real Estate

Chester is located in Maryland. Chester, Maryland 21619has a population of 4,371. Chester 21619 is less family-centric than the surrounding county with 23.42% of the households containing married families with children. The county average for households married with children is 31.88%.

The median household income in Chester, Maryland 21619 is $84,835. The median household income for the surrounding county is $99,597 compared to the national median of $69,021. The median age of people living in Chester 21619 is 43.9 years.

Chester Weather

The average high temperature in July is 87 degrees, with an average low temperature in January of 28.3 degrees. The average rainfall is approximately 46.2 inches per year, with 12.7 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $669,900
    14.5%
    change since last quarter
  • # Active listings

    93
    30-day change

Chester Schools and Demographics

Education near Chester, MD

City County
High School Graduates 92.01 92.87
College Degree - 2 year 9.35 7.89
College Degree - 4 year 31.36 36.96
Graduate Degree 8.55 10.55
Expenditures per Student 15,198 15,198
Students per Teacher 14.4 14.4

Elementary Schools near Chester, MD

Grades Students P/T Ratio ZIP
Bayside Elementary School 03 - 05 402 16.1 21666
Cape St. Claire Elementary KG - 05 646 15.9 21409
Grasonville Elementary School PK - 05 494 15.9 21638
Kent Island Elementary School PK - 02 469 16.2 21666
Matapeake Elementary School PK - 05 493 15.4 21666
Rock Hall Elementary School PK - 05 187 14.3 21661
Windsor Farm Elementary School KG - 05 608 17 21409

Middle Schools near Chester, MD

Grades Students P/T Ratio ZIP
Matapeake Middle School 06 - 08 416 15.4 21666
Stevensville Middle School 06 - 08 474 13.5 21666

High Schools near Chester, MD

Grades Students P/T Ratio ZIP
Broadneck High School 09 - 12 2,104 18.4 21409
Kent Island High School 09 - 12 1,194 15.5 21666

Demographics near Chester, MD 21619

Zip Code City
Neighborhood Type Small town
Population 4,371 49,702
Population Density 835 134
Median Age 43.9 44.7
People per Household 2.4 2.6
Median Household Income 84,835 99,597
Average Income per Capita 53,406 49,178

Real estate near Chester