23 houses for sale in Tolchester Estates

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm

Take advantage of the Eastern Shore's amenities and quality of life in this low maintenance one floor home just a hop and a skip from the Chesapeake Bay and public beach. The Sergeant's Quarters at Tolchester Village is located less than 15 minutes from both Chestertown and Rock Hall providing nearby cultural, entertainment, and employment opportunities. The home itself has been taken care of with love and is ready for its next steward. Vaulted ceilings and spacious room sizes provide a great feel. The Shanty Bar at Tolchester Marina, just a beach cruiser or golf cart ride away, is one of the Chesapeake Bay's premier beachfront establishments serving coastal fare, fresh made boat drinks, and hosting live music on the Bay. Invest wisely in this tranquil retreat with bountiful nearby attractions

Toad Hall, as the current owners affectionately call it, is located in a natural wooded setting on Fairlee Creek in Great Oak Estates just minutes from the Chesapeake Bay. Peaceful water views from almost every room in the home create the feeling of living in a tree house, and the dock is just steps away down the hillside. No flood insurance needed. Enter the house through a split foyer with a few steps up to the main level and into the great room with the central kitchen, dining and living areas. The master suite is located on one end of the main level and features a large walk-in tile shower and a small private deck. The other end of the main level features a vaulted sunroom, a great spot to commune with nature or host the family crab feast. The lower walk out level offers a family room with a wood stove, two bedrooms, a full bath, a laundry room, and outdoor access. 2.5-3' MLW Buyer to verify. See Documents for Seller updates plus info on Association benefits. New roof added in 2021

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs. All on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive 1.66-acre lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provi

Charming home nestled on a spacious lot in the Rock Hall area. This property offers comfortable single-level living with a functional layout, generous outdoor space, and plenty of room to enjoy the peaceful surroundings. Conveniently located near local amenities, marinas, and the Chesapeake Bay, this home presents an excellent opportunity for year-round living, a weekend retreat, or investment potential. Don't miss the chance to make this Eastern Shore property your own! Sold as is

Agents. Please view agent remarks in bright mls. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot that offers both tranquility and privacy located just a few miles from historic Chestertown. Surrounded by mature trees and bordered by a serene cornfield, this property provides a peaceful retreat from the hustle and bustle of everyday life. The home has been thoughtfully designed to accommodate comfortable everyday living as well as entertaining guests. The spacious rear deck is an ideal spot for hosting gatherings, enjoying morning coffee, or simply relaxing while taking in the natural beauty of the surroundings. Step inside to discover a modernized kitchen equipped with updated appliances and ample counter space, making meal preparation a pleasure. The bathrooms have been tastefully updated to combine style and functionality, while new windows throughout the home allow for plenty of natural light and energy efficiency.

Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip. 3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak. The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home. In both sitting rooms, youll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated. Upstairs youll find two waterfront bedrooms, one with an updated attached bath. There's a

Move in ready! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Diningu002Ffamily rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. Just a very quick trip to entertainment, or boating. Great location, private lot just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential

Beautifully updated and move-in ready, this charming one-level home offers the perfect blend of comfort, style, and convenience! Recent improvements include a newly added full bath off the living area and a beautifully remodeled half bath featuring a gorgeous walk-in shower and all new finishes The inviting kitchen includes an eat-in dining area, breakfast bar, wine cooler, and brand-new appliances. Ideal for entertaining or everyday living. Gorgeous hardwood floors and attractive tilework throughout add warmth and character. Relax on the enclosed side porch with peaceful neighborhood views or enjoy outdoor living on the newly build deck designed for sunny afternoons and evening gatherings. Located in the heart of Rock Hall, this home places you close to marinas, public landings, local shops, restaurants, and all the charm this beloved Chesapeake Bay town has to offer. Enjoy seasonal festivities, waterfront living, and the laid-back lifestyle Eastern Shore buyers love. Whether you are

Move in ready! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently upgraded, beautifully tiled bathroom flooring. Freshly painted, Bright and inviting updated kitchen, Spacious Dining/family rm with vaulted ceilings, ceiling fan. Enjoy fishing or relaxing at the private community beach or head over to Tolchester Marina & The Shanty Beach Bar, dining & shopping. Just a very quick trip to entertainment, or boating. Great location, private lot just 10 minutes from downtown Chestertown or Rock Hall where you can enjoy shops, marinas, dining and regular events. Level lot with plenty of potential

All showings require pre screening and financial capability prior to scheduling any showing. Rarely does a property of this sort come available in Kent County Maryland! This incredible 139+u002F. Acre Chesapeake Bay property is available in it's entirety, however the seller may consider selling the primary residence with a reduced amount of acreage under the right conditions, providing the purchaser bares the cost to do so and is willing to wait the extended period of time to accomplish. The entire property features 72+u002F. Tillable acres, 3900+u002F. Footage of Chesapeake Bay beach frontage, extensive County road frontage, a 3.5 acre waterfowl pond, 2 other smaller ponds, a ten stall horse barn, and caretakers home. A large 33+u002F. Acre flooded area, teeming with waterfowl and deer surrounded by woods runs through the heart of the property. The main residence, designed by architect Paul Rudolf, is perched upon the rip rapped shores of the Chesapeake Bay with endless broad water vi

Welcome to Chesapeake Landing where new construction meets timeless Cape Cod charm in the heart of Chestertown, MD. This brand-new 3 BR / 2.5 BA home at 10584 Klamath Rd by Roger Reed Builders (MD Lic. 2464) is move-in ready with quality finishes throughout. The open main level features luxury vinyl plank flooring, white shaker cabinets, granite countertops, a full stainless steel appliance package (side-by-side refrigerator with ice maker, over-range microwave, built-in dishwasher, smooth-surface electric range), and a convenient half bath. The primary suite offers a walk-in closet, ceiling fan, and en suite bath with granite vanity. Two additional bedrooms and a full bath with granite counters round out the upper level. Enjoy the ease of a private well and septic, 2-ton heat pump, and no HOA. Gravel driveway, vinyl siding, 25-year shingles, and three black exterior lights give great curb appeal. Don't miss your chance to own a brand-new home in one of Kent County's sought-after commu

Lovely 4 Bedroom home with 1 and 1/2 baths located just outside of town. This home has 2 separate entrances at the front of the house. One can be entered and separated from the whole house living space. Great for an office with 1/2 bath or used as another bedroom if you need 4. Kitchen leads to separate laundry and mud room and exits to the back yard with a view of acres of open space fields

Reice reduced! Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms — one on each level — this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel appliances, and abundant natural light throughout. A convenient rear mudroom leads to a covered porch. Upstairs, you’ll find generously sized bedrooms with large windows, while the third floor offers an additional expansive sitting area — perfect for a home office, media room, or bonus living space. Brand-new carpeting adds warmth and comfort to the upper levels. The current owners have incorporated thoughtful upgrades and modern features throughout, making this home truly move-in ready. Enjoy the charm of Rock Hall living with the benefit of a fully updated home just minutes from t

Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch, perfect for relaxing or entertaining. Inside, the home offers a bright and open layout with modern finishes while still retaining that classic Cape Cod charm. Sitting on a large lot, there’s plenty of space for outdoor activities, gardening, boat storage or future expansion. The is ample parking in the driveway as well as two-way access. Ideally situated in the sought-after waterfront town of Rock Hall, you’ll be just minutes from multiple boat ramps, marinas, and a short walk to restaurants, local shops, and the center of town. Whether you're looking for a full-time residence or a weekend getaway,

This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance storeshowcasing its adaptability for a wide range of business ventures. The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining. Additional improvements include a 35 x 28 pole barn and a 28 x 14 shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment. With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort

Chesapeake Landing. This home is featured on a corner lot with large living space and additional space above the detached two car garage. Opportunity is knocking at this property, for you to make your forever home. The home features a beautiful sunroom to entertain in as well as a large family room. This home has a large laundry room that is a must have! The hardwood floors are just another great feature of this home. Call today for your showing appointment

Reice reduced! Completely renovated from the studs up, this beautifully updated 3-story home offers 2,200 square feet of thoughtfully designed living space just outside of Rock Hall. Featuring 3 spacious bedrooms and 3 full bathrooms one on each level this home provides flexibility and comfort for everyday living or guests. The open-concept main floor showcases luxury flooring, brand-new stainless steel appliances, and abundant natural light throughout. A convenient rear mudroom leads to a covered porch. Upstairs, youll find generously sized bedrooms with large windows, while the third floor offers an additional expansive sitting area perfect for a home office, media room, or bonus living space. Brand-new carpeting adds warmth and comfort to the upper levels. The current owners have incorporated thoughtful upgrades and modern features throughout, making this home truly move-in ready. Enjoy the charm of Rock Hall living with the benefit of a fully updated home just minutes from town, ma

Welcome to life in Rock Hall a charming waterfront town where the pace is slower, the people are friendlier, and the Chesapeake Bay lifestyle is part of everyday living. Seller assistance available towards closing costs. This lovingly renovated home was thoughtfully updated by owners who cared about the detailsnot a quick flipresulting in a property full of character and quality improvements throughout. Inside, youll find beautiful LVP flooring, a bright open-concept layout, and a stunning kitchen featuring granite countertops, a tile backsplash, stainless steel appliances, and plenty of space to gather after a day on the water, experiencing Chestertown and all the other towns nearby! Owner had a pre home inspection for your convenance! The home is good to go! For peace of mind, all major systems are new, including a brand-new roof, and a home inspection has already been completed with items addressed, making this home truly move-in ready. The layout offers comfort and privacy with the

Price improvement! Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office. Kitchen with marble countertops and a huge professional refrigerator. Fully finished basement. 2 car attached garage. The first outbuilding is a office space with 2 private offices, a conference room, a gym, kitchenette and half bath. The second outbuilding features 5 garage bays and a finished area that serves as a family room with kitchenette. This property is nothing short of spectacular

Price improvement! Wait until you see this! Impecably maintained brick house on nearly 20 acres, overlooking a pond with tons of privacy. 2 large outbuildings. High-end upgrades and fixtures. The house has 4 bedrooms and 3.5 baths. A primary owner's suite on the main floor and an additional owner's suite on the second floor. Beautiful hardwood floors throughout. The main floor features a bar room and an office. Kitchen with marble countertops and a huge professional refrigerator. Fully finished basement. 2 car attached garage. The first outbuilding is a office space with 2 private offices, a conference room, a gym, kitchenette and half bath. The second outbuilding features 5 garage bays and a finished area that serves as a family room with kitchenette. This property is nothing short of spectacular

Update. New carpet just installed! Convenient one-level living in this 3BR, 2.5 bath rancher. The house has a desirable split bedroom layout with the primary bedroom, bath & closet off the kitchen and two bedrooms and another full bath off the other side of the house. The sun room has a propane stove and exits to a 12' x 15' deck. There's a 10' x 16' shed. Nice quiet, in-town location

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This spectacular waterfront retreat offers over 3,500 square feet of living space on 0.76 acres, ideally located within the town limits of Rock Hall. With an elevator, five bedrooms an office and four and a half baths, there is abundant space for family, guests, and effortless entertaining. The ground level welcomes you with a spacious game room, sitting area, exercise space, and an oversized two-car garage. A split-level entry foyer leads to the main living area, where an open-concept layout seamlessly connects the living and dining rooms. The expansive kitchen with two sinks and wine fridge is designed for both function and gathering, featuring generous cabinetry and ample countertop space. Just off the kitchen, the family room with vaulted ceiling, opens to a screened porchperfect for enjoying cool breezes and waterfront views. A deck spanning the width of the home provides additional outdoor living space and includes an electric hoist for firewood or groceries. A living room with w