Mary Fielding
410-708-4852

Chestertown MD Real Estate & Homes for Sale

44 Properties Found

The median home value in Chestertown, MD is $270,000. This is higher than the county median home value of $178,000. The national median home value is $277,796. The average price of homes sold in Chestertown, MD is $270,000. Approximately 44% of Chestertown homes are owned, compared to 42% rented, while 14% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


1–25 of 44 properties displayed
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Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
3,578
Status:
Active
MLS#:
MDKE118226
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Neck
Lot size:
1.34 Acres
Year built:
1975
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Chestertown Waterfront home! Dock with 2 boat lifts and deep water! Bring your sailboat 4' at the dock and 20' a short distance out from the dock on the Chester River! Home has everything you could want plus more! Lovely flow floor plan taking advantage of the water views! Gourmet kitchen with gorgeous Slate backsplash and granite counters. Large Kitchen Island to share all your yummy food. Waiting for guests? Pop the food in the plate warmer. Lots of room for entertaining. The primary suite has a Huge Bedroom, 2 Balconies, one for 3 seasons with beautiful views of the water. And the other Balcony is open. Large sitting area and the biggest walk-in closet I've seen! Laundry room with plenty of space. One room is used as a Study but has a closet, so it could easily be turned into a 5th Bedroom. Bamboo and Hardwood floors. Large deck and slate patio, great for relaxing and entertaining. So many amenities, you'll just have to come and check it out!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,694
Status:
NEW LISTING
MLS#:
MDQA2001364
Type:
Other
Subdivision:
Pondtown
Lot size:
1.01 Acres
Year built:
1965
Courtesy: Select Land & Homes, LLC
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One acre country lot with bungalow located in Pondtown in Northern Queen Anne County. Property is being sold AS-IS, Where-IS. Minimum of 24 hour notice to show. Home is habitable with tenant but needs substantial rehab. Easy commute to Delaware!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,253
Status:
NEW LISTING
MLS#:
MDQA2001370
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
5.13 Acres
Year built:
1962
Courtesy: Doug Ashley Realtors, LLC
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Great opportunity to own a 3 bedroom, 1 bath home and 2 additional perc approved building lots. The main parcel has 2+/- acres, lot 2 has 1.4+/- acres and lot 3 has 1.5+/- acres with a total acreage of 5+/- acres. The main parcel has a modest home with a 3 car detached garage. The mound septic system was installed new 5+/- years ago. The rear deck allows for private outdoor enjoyment. The 3 car detached garage could work well as a shop and garage combination.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,196
Status:
NEW LISTING
MLS#:
MDQA2001318
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.52 Acres
Year built:
1972
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Well maintained rancher with full basement just waiting to be finished, ALMOST 2,000 SQUARE FEET! Potential for rooms and plenty of storage in the basement as well as a brick wall waiting for a new wood stove, and outside entrance. Hardwood floors on main level with hardwoods under vinyl and carpet. Bathroom updated a couple of years ago and main level laundry., or move the laundry downstairs and create a full 2nd bathroom. Garage has space for 2 vehicles and plenty of storage. The community HOA is voluntary and does allow access to the community pier. Round Top Park is a county park minutes away with picnic areas, grills, a pavilion, basketball and tennis courts, a playground, and various athletic fields. Close to Chestertown shopping and the Saturday Farmer's Market, plus an easy commute to 301! Make this your new home!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,268
Status:
NEW LISTING
MLS#:
MDKE2000039
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.34 Acres
Year built:
1957
Courtesy: Cross Street Realtors LLC
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This 3 BR brick rancher, set amidst flowering shrubs on a quiet street in College Heights, offers a country size kitchen with cooktop and wall oven, polished hardwood floors throughout, wood burning fireplace, and a 2-car attached garage. All within walking distance to everything Chestertown has to offer; Farmers Market every Saturday morning, Arts & Entertainment district, Washington College, restaurants, local shops, and much more. With low and even a possible no-down payment options, there's no need to wish!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
4,316
Status:
NEW LISTING
MLS#:
MDKE2000560
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.26 Acres
Year built:
2011
Courtesy: Sid Sells Maryland Realty
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Professional photos coming October 14th. Do not miss this expansive turn key colonial in Coventry Farms II. Original owners opted for all of the additional square footage options when this home was built. Oversized bedrooms with plenty of closet space and storage. Brand new TRANE HVAC. Rear deck was added in the past year and permits are on hand with Kent County. Basement has a rough for a bathroom as well as a wet bar.

Open House:

Saturday, 10/30 11:00-1:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
997
Status:
NEW LISTING
MLS#:
MDQA2001174
Type:
Single Family, Single Family-Detached
Subdivision:
Pear Tree Point
Lot size:
0.37 Acres
Year built:
1980
Courtesy: Cross Street Realtors LLC
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This delightful 2 BR, 1 BA cottage style residence offers affordable living and low maintenance with an open kitchen/dining/living area, breakfast bar, wood burning fireplace, freshly painted throughout, polished hardwood floors, a 1-car attached garage and deeded water access to the Chester River. All within biking distance or a quick drive to everything Chestertown has to offer; Farmers Market every Saturday morning, Arts & Entertainment district, Washington College, restaurants, local shops, and much more. Nothing to do but move in and enjoy the Eastern Shore charm!

Open House:

Saturday, 11/6 11:00-1:00PM

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
3,080
Status:
NEW LISTING
MLS#:
MDKE2000586
Type:
Single Family, Single Family-Detached
Subdivision:
Village At Chestertown
Lot size:
0.09 Acres
Year built:
2021
Courtesy: RE/MAX Executive
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Need to settle on a new home quickly? Desire space, modern amenities, and minimum exterior maintenance? The Village at Chestertown offers a small home town environment with stress free living. Walking paths, street lighting, exterior designs that mirror the historic architecture throughout Chestertown, mature trees and plantings, community pergola over looking the community pond, give this community that Norman Rockwell charm that transforms you back to yesteryear. Imagine yourself siting on your front porch greeting your neighbors as they stroll by. As you enter this home, your eye goes to the beautiful kitchen that is the center and heart of the home. The open concept first floor combines the dining, living and kitchen space making entertaining a breeze. The upper floor houses the bedrooms....four in all. All bedrooms are spacious but the primary bedroom with it's private bath and walk in closet is the space you have been dreaming of. Your guests are not neglected, the additional three bedrooms and bath are also made to impress. Add your own stamp to the unfinished basement with high ceilings and rough in plumbing for that future bath....let your imagination explore the possibilities. *** professional photos and video soon***

Open House:

Saturday, 10/30 11:00-1:00PM

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,600
Status:
NEW LISTING
MLS#:
MDKE2000578
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Chaney Homes, LLC
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Beautiful fully renovated historic home in downtown Chestertown is walking distance to shopping and dining! This 3 bedroom 2 1/2 bathroom home offers a first floor master suite, open floor plan, walk-in pantry, custom finishes, finished third floor could be used as a fourth bedroom, a large brick patio with built in fire pit, and more! Hurry to make this beauty your new home!

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,795
Status:
NEW LISTING
MLS#:
MDKE2000570
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
2.77 Acres
Year built:
2003
Courtesy: Gunther-McClary Real Estate
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Fabulous, custom-built, 2800 square foot home on 2.77 wooded acres. This move-in-ready home has new carpet and has been freshly painted for its new owners. Family room features cathedral ceilings and a gas fireplace. Open floor plan allows you to move easily from the family room to the kitchen, dining room, and breakfast areas. Off the kitchen, you'll find a screened in porch with gas wall heater. The large, primary bedroom has access to the back deck. Primary bathroom features a soaking tub, two vanities, shower and oversized walk-in closet. All 3 guest bedrooms are ample-sized. There is plenty of storage in this house between the garage, mud room, and walk in attic. The home is in a private, wooded setting that backs to farmland. Fiber Internet service is available. Make this place your home!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,026
Status:
NEW LISTING
MLS#:
MDQA2001260
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1988
Courtesy: Long & Foster Real Estate, Inc.
View additional info

3 BR, 1 BA rancher, located in water community, not far from Rosin Creek. Nice starter home, new carpet in living room and hallway and new vinyl through out.

Open House:

Sunday, 10/31 1:00-3:00PM

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,334
Status:
NEW LISTING
MLS#:
MDKE2000534
Type:
Single Family, Single Family-Detached
Subdivision:
Mile Tree Village
Lot size:
0.46 Acres
Year built:
1987
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Rare find located in Mile Tree Village. This beauty offers 4 bedrooms, 2 1/2 bathrooms, large family room, plus formal living, private office off the kitchen with a first floor master. Very private fenced in backyard has a large deck, gorgeous landscaping with a detached garage and shed. Detached garage offers a place to park, a loft for storage and another office/studio.

Beds:
5
Baths:
4 Full/2 Half
Sq.Ft.:
7,932
Status:
Active
MLS#:
MDQA2000065
Type:
Single Family, Single Family-Detached
Subdivision:
Skipper Lands
Lot size:
0.89 Acres
Year built:
2004
Courtesy: Gunther-McClary Real Estate
View additional info

Spectacular classic Georgian style 5 bedroom home located on .88 acres with approximately 150' of waterfront. As one enters the home, the immense hallway directs you to French doors on to a brick porch, yard and then dock on the Chester River. The 130' dock holds 4 boat lifts, one 12,000pd lift. Nothing was spared in the construction of this extraordinary home. All brick exterior built with flood plain construction. Heated heart pine floors and custom tile, heart pine built in cabinets, spacious kitchen with breakfast bar, separate dining room and informal eating area off the kitchen. Two staircases leading to the 4 bedrooms, 3 with ensuite bathrooms, large gathering area and spacious TV room which is currently used as. First floor master suite, with large master bath, custom built in closets. and access to the waterside porch. Office with built in cabinets. Separate entrance by the waterside to a powder room and laundry area. Kitchen is also accessed by the garage. Too many amenities to mention. A must see. Enjoy all kinds of vessels sail or power up to Chestertown, the home to the Down rigging of the Sultana Weekend, what a site to see these tall ships come in for the weekend in Chestertown in the fall.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDKE2000045
Type:
Single Family, Single Family-Detached
Subdivision:
Georgetown
Lot size:
1 Acres
Year built:
1998
Courtesy: The Hogans Agency Inc.
View additional info

One floor living in country setting. Low maintenance three bedroom two full bath rancher on large lot backs to woods and farmland. 10 minutes to Rock Hall on Chestertown and under 2 hours to Baltimore and Philadelphia. On one acre to be subdivided by the Sellers.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDKE2000029
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
1.25 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Come see this quaint 2 bedroom 1 bathroom 1920 farmhouse on 1.25 acres. Could be a great flip or remodeled into a wonderful home. Main floor has a large living room, sun room, full bath, kitchen and laundry room. Upstairs features two bedrooms. Oversized shed with electric in great condition. Septic system has a failed drain field. Only a drip system or holding tank permissible. Property is secluded, backs to woods and located on a quiet country road just a few minutes outside of Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront walkways and parks. Just a few minutes walk to the river, waterfront dining and Wilmer Park. Chestertown is home to many festivals and the local Farmer's Market on Saturdays. Just 90 minutes to Washington D.C. or Philadelphia.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,049
Status:
Active
MLS#:
MDKE2000009
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.56 Acres
Year built:
1972
Courtesy: Rock Hall Properties Real Estate
View additional info

Nestled among the gardens and Mill Creek is 10840 Foreston Road in the broadband accessible Chesapeake Landing community conveniently located between Chestertown and Rock Hall. This waterfront retreat has a private pier with boat slip and 3+ ft. water depth. Worton Creek Marina is also nearby for boat repairs. The house has 3 bedrooms, plus 2 full baths and a powder room. There's a recently remodeled kitchen and laundry, plus a fireplace in the living room to keep you cozy on chilly nights. You'll enjoy entertaining on the rear and side decks plus the screened-in back porch after a fun day on the water. The abundant waterfowl and wildlife create a peaceful, relaxing environment where you can unwind and enjoy this nature-lovers paradise. Less than 2 hours from PA, NJ and DE.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
4,730
Status:
Active
MLS#:
MDKE2000502
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.61 Acres
Year built:
2011
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The landscaping around the circular driveway is lovely; the garage is set on an angle as to be unobtrusive from the road and the house entrance. Inside, all the rooms enjoy the views; the glassed in sun room being the most spectacular. Beautiful flooring, oversize crown molding, chair rails, accent & recessed lighting and painted paneling throughout. New A/C handler, Rinnai system with boosters (to reach around this 4,000+ sq. ft. house), foam insulation underground and up the walls, crawl space encapsulated, 3 temperature zones and audio wired surround sound. The kitchen and owner's suite are too great to try to describe, for instance, the marble came directly from Italy and no longer available. Laundry and "mud kitchen" are between the owner's suite and garage. Take a golf cart to the club, ride a bike into town or just sit and watch the tall ships go by.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
1,800
Status:
Active
MLS#:
MDQA2001246
Type:
Single Family, Single Family-Detached
Subdivision:
Blakefield
Lot size:
28.86 Acres
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

NEW CONSTRUCTION TO START RARE FIND. 28 .86 ACRE HOME SITE WITH 18 ACRES USABLE. GREAT NEW FLOOR PLAN 4 BED 2,5 BATHS. NO MORE WORRIES ABOUT NOT ENOUGH LAND. YOU CAN RUN, JUMP JUST GO CRAZY ON THIS LOT. FLOOR PLAN ONE OF THE BUILDERS BETTER LAY OUTS. 4TH BEDROOM COULD MAKE NICE HOME OFFICE. BRING YOUR OWN PLAN IF THIS ONE DOES NOT FLOAT YOUR BOAT. LOT IS ALSO FOR SALE OUTRIGHT AT MLS# FOR LOT IS MDQA2001100

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,544
Status:
Active
MLS#:
MDKE2000566
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
2.03 Acres
Year built:
1991
Courtesy: Coldwell Banker Realty
View additional info

This remarkable property has so much to offer! Comfortable home with so many quality features! Beautiful concrete pool w/ hot tub and poolhouse w/ bathroom/changing area, detached 26x38 heated garage/shop/office, great location in the sought after Quaker Neck area, near Chestertown, yet not isolated. 2+ acre partially wooded lot overlooking unspoiled farmland. Wood floors, 2nd floor laundry, sunroom, custom moldings, and much more! New Roof-2019 New Septic-2021 New HVAC-2021 This house has so many upgrades that you'll need to see for yourself.

Beds:
5
Baths:
3 Full
Sq.Ft.:
1,600
Status:
Active
MLS#:
MDKE2000510
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee
Lot size:
2.1 Acres
Year built:
1900
Courtesy: RE/MAX Executive
View additional info

Looking for country living with public utilities? This home has both!! Located 10 mins from Chestertown and Rock Hall on the outskirts of the village of Fairlee, this home is roomy inside and out. Offers just over 2 acres of land available for gardening, play, expansion, storage or just that extra breathing room. Only a short distance to Fairlee landing so bring the boat or water toys with you. Inside you will find many updates that include new paint, flooring, kitchen cabinets, granite countertops, updated bathrooms and even a media room or first floor bedroom with a one of a kind ceiling. From the square footage to the acreage, this is quiet the country charmer. Looking to add an outbuilding â¦.you have more than enough room here. Plus a home warranty through Cinch home warranty company.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
2,300
Status:
Active
MLS#:
MDQA2001086
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.6 Acres
Year built:
1986
Courtesy: Long & Foster Real Estate, Inc.
View additional info

CAPTIVATING CHESTER RIVER PRIVILEGED COLONIAL close to beaches, pier & playground! Sprawling rear yard inviting picnics, pets & play! Meticulously maintained brick/siding home with sun-dappled rocking chair porch. TOTALLY TURNKEY neutral paint palette/carpeting! Formal Living & Dining Rooms. Large Family/Media Room. Updated Kitchen breakfast bar. Bright & breezy Bedrooms or possible Home Office! Unfinished lower level with space for game tables/workbench. Expanded multi-vehicle parking court for RV or boat trailer; 1-car garage. WALK or BIKE ALONG TREE-CANOPIED STREETS ... TAKE A ROMANTIC RIVERSIDE STROLL. LIVE IN AND LOVE CHESTERTOWN!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,782
Status:
Active
MLS#:
MDQA2000894
Type:
Single Family, Single Family-Detached
Subdivision:
Pear Tree Point
Lot size:
0.64 Acres
Year built:
2000
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Extraordinary Eastern Shore waterfront home for sale. From its perch above the water, this thoughtfully designed home enjoys lovely broad views of the Chester River and vistas of expansive marshlands on the other side. Designed by award-winning architect Peter Newlin, FAIA, architectural elements are evident throughout the home including his signature free-standing fireplace and curved stair with skylight. The open floor plan and expansive windows exude warmth and comfort accentuated by captivating river views. There were extensive renovations in 2000, including the addition of the second floor. There are interior details not finished. Please see Features to Enjoy in the documents - written by the owner/architect. The residence is located in Queen Anneâs County, Maryland and is about a 4-mile drive or quick boat ride to historic Chestertown. Founded in 1706, and home to Washington College, Chestertown is a lovely waterfront town with brick sidewalks, shops, restaurants, walking trails, parks and cafes. It is about 90 minutes from Washington, D.C. and Philadelphia.

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
2,352
Status:
Active
MLS#:
MDKE2000484
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee Creek
Lot size:
1.36 Acres
Year built:
1994
Courtesy: Doug Ashley Realtors, LLC
View additional info

Located just ten minutes from historic Chestertown this is your chance to own an amazing property, with panoramic views, perched above the coveted "Fairlee Creek"! Enjoy spectacular sunrises and sunsets from your private dock where deep water slips, 6'+/- at high tide, are just minutes from the Chesapeake Bay, yet well protected. The house was re-built approximately six years ago, with all plumbing and electric replaced and foam insulation was applied for quiet and comfort. The kitchen was designed with dual main sinks, high-speed ice-maker, quartz countertops and an over-sized island. Itâs perfect for group cooking and entertaining. The first floor has six-foot-tall windows in the living room and main suites, providing water views from nearly every room. There are two owner suites on the first floor in a split floor plan design. Hardwood floors can be found throughout first floor. The upstairs has skylights, a loft bedroom with separate heating and cooling, its own private bath plus a very large bonus room. Ceiling fans can be found throughout the house, including the screened porch. Dual hot water heaters located in the encapsulated and conditioned crawl space insure the availability of hot water when you need it. A public boat ramp is located just one property away for amazing convenience and exclusivity.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,944
Status:
Active
MLS#:
MDQA2001084
Type:
Single Family, Single Family-Detached
Subdivision:
Reba Anthony Estates
Lot size:
0.39 Acres
Year built:
1981
Courtesy: Benson & Mangold, LLC
View additional info

Exceptional brick Cape Cod on the Queen Anne County side of Chestertown. This beautiful home features a Florida room, den with built-in bookcases, open kitchen and wood floors throughout. Mature yard with beautiful gardens. Quiet dead end street with little traffic and a whole house gas generator for backup in emergencies.

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
5,200
Status:
Active
MLS#:
MDKE2000490
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
1 Acres
Year built:
2000
Courtesy: Doug Ashley Realtors, LLC
View additional info

Stunning and elegant 5 bedroom, 3.5 bath custom Georgian residence on great 1 acre lot perfect for relaxing or entertaining. Just minutes from Downtown shops and restaurants, the Marina and the Country Club. Designer touches include extensive chair and panel molding detail, beautiful lighting fixtures, custom drapery with restoration hardware rods, large open kitchen with granite counters and stainless steel appliances, hand made built in media cabinet, widow's walk with amazing water view of the Chester River, huge screened porch overlooks lush backyard. Custom carved fireplace. Hardwood floors throughout main and upper level. Many French doors bring added style. Italian rose marble flooring and crystal chandelier made the dining room a statement. Full size basement includes a recreation room, bedroom and full bath in addition to storage. Rennai instant hot water heater. Roof replaced in 2021. Agent is owner.

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