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Mechanicsville & Leonardtown MD Real Estate

Mechanicsville and Leonardtown are quaint Maryland communities with a vibrant history. Located about 20 mins apart, the homes for sale Mechanicsville and Leonardtown are located on beautiful, rural lots and in welcoming suburban neighborhoods. Local vineyards and farms are scattered across the rolling landscape and there are many hiking/walking trails and parks, perfect for those who enjoy an active lifestyle.

Maryland Homes For Sale

Search homes for sale in Mechanicsville and Leonardtown area.  Contact us if you have questions or would like to schedule a showing. You might also be interested in St. Mary's County Real Estate.

40490 Kavanagh Rd Mechanicsville MD 20659

MLS Number MDSM161308

  • Single Family
  • Address 40490 Kavanagh Rd
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1092

Rambler sitting on almost 3 acres. Great potential. Heir property. Bring your best offer.

Listed by RE/MAX Specialists

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$
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$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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21716 Fairway Dr Leonardtown MD 20650

Price$429,000

Est. Mortgage: $/month

MLS Number MDSM161310

  • Single Family
  • Address 21716 Fairway Dr
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 2752

Beautiful home in serene setting! This home features 5 bedrooms, 3 1/2 bathrooms, gorgeous hardwoods floors, updated kitchen with stainless steel appliances, separate living room and dining room, and open family room. Freshly painted. All of this surrounded by mature trees and beautiful landscaping with spectacular golf course views! Close to shopping and historic downtown Leonardtown. This one is a must see!

Listed by O Brien Realty

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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29816 Adams Rd Mechanicsville MD 20659

Price$240,000

Est. Mortgage: $/month

MLS Number MDSM161182

  • Single Family
  • Address 29816 Adams Rd
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2124

Spacious home. Easy to make main level 3 bedrooms again. Home offers 2 master bedrooms. Bathrooms have been updated, lower level flooring is all new. Easy walk to the water.

Listed by RE/MAX 100

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41395 Doctors Crossing Rd Leonardtown MD 20650

MLS Number MDSM161256

  • Single Family
  • Bathroom 4
  • Bedrooms 5
  • Square Feet 3388
  • Year Built 2016

Why wait, move in ready Grand Haven in Clark's Rest community. Featuring Hardwood in Foyer, DInning room, Kitchen. Huge walk-in pantry. Gourmet Kitchen! Stainless Steel Appliances. Laundry on 2nd Floor. HUGE Owner's Closet. Sitting Room at Owner's Suite. Upgraded Tile @ Owner's Suite. Finished Lower Level Room, Rec.Room and Full Bath. Gas Fireplace.

Listed by O'Brien Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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22538 Landing Leonardtown MD 20650

MLS Number MDSM161290

  • Rental Townhouse
  • Date Available 06/01/2019
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2764

Nice 3 bedroom townhome with 2 car garage and fully finished basement at Leonardtown Landings. Credit application is $75 per adult and must be completed online: https://listing2leasing.com/q.php?q=22538-landing-way-leonardtown-md-20650-rhpnev

Listed by Century 21 New Millennium

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23970 Maypole Leonardtown MD 20650

MLS Number MDSM161288

  • Rental
  • Date Available 04/18/2019
  • Bathroom 1
  • Bedrooms 1
  • Square Feet 600

Lovely one bedroom apartment in Leonardtown. Wood floors throughout. Coin operated laundry in common area. Application fee is $75 per adult and must be completed online. https://listing2leasing.com/q.php?q=23970-maypole-roadd-leonardtown-md-20650-rbhzkm

Listed by Carolyn A Kalmus-Choporis and Cynthia M Crispell of Century 21 New Millennium

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26474 Laurel Grove Ct Mechanicsville MD 20659
Open House

MLS Number MDSM161270

  • Single Family
  • Next Open House: Sun 28th 2:00 pm - 4:00 pm
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2549

Gorgeous colonial set on 5 acres of privacy. This home has it all- inside and out! Large deck on back of house w/sub deck wired for hot tub. 16x32 inground pool with tiki hut for entertaining. New roof, new carpet, fresh paint and stainless steel appliances. Basement features wood stove, aged barnwood, and ceiling fans. Separate 36x24~ three-car garage. Stunning landscaping! See it today. Lots of lawn equip/pool equip/patio furniture convey!

Listed by Redfin Corp

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27416 Fred Mechanicsville MD 20659

MLS Number MDSM161066

  • Rental
  • Date Available 05/01/2019
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1800

This is a great 6yr old Ranch home 1800+ sq ft that has fresh paint and carpet. Comes with all appliances including 26 cu ft french door refrigerator, new cook top stove and washer & dryer. Also has large storage shed with loft & shelves for lots of extra storage. Also comes with lawn tractor and other tools to help you maintain the lawn. Master suite with double sink vanity,full size shower

Listed by Coldwell Banker Jay Lilly Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27885 Queentree Rd Mechanicsville MD 20659

Price$1,085,000

Est. Mortgage: $/month

MLS Number MDSM158272

  • Single Family
  • LocationType River
  • Address 27885 Queentree Rd
  • Bathroom 5
  • Bedrooms 3

Spectacular Custom Built Water Front Home on Patuxent River with breathtaking views. Special Features Include: Private Pier with 16 ton boat lift and jet ski, soaring cathedral ceilings with perfect views in the family room, refinished hardwood floors, brand new SS appliances, main level master bedroom, huge basement with heated floors, built ins, oversized 3 car garage, all bedrooms have own full baths and much much more. Convert the gym in the basement to a 4th bedroom or finish the big room above garage. A must see!

Listed by Century 21 New Millennium

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26546 Three Notch Rd Mechanicsville MD 20659

MLS Number MDSM161258

  • Single Family
  • Address 26546 Three Notch Rd
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1066

Rambler on full basement with detached garage/Outbuilding, with electric. Affordable and shows well. Great location to commute North or South. Full basement to finish as you like. Lots of potential with this property. Flat level yard

Listed by RE/MAX One

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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43011 Chickadee St Leonardtown MD 20650

Price$419,900

Est. Mortgage: $/month

MLS Number MDSM161234

  • Single Family
  • Address 43011 Chickadee St
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2339

**TO BE BUILT** Quality Built Homes' newest rambler to be featured in Meadows at Town Run! This is one leveling living at its' finest. Complete with a split bedroom floor plan...a large master suite on one side and the other 2 bedrooms on the other side of the house! Huge galley kitchen that opens to the family room. A sunroom like breakfast area that walks out to a covered porch. What more can you ask for? Get in soon while it's still pre-construction pricing!

Listed by RE/MAX United Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42162 Woody Ln Mechanicsville MD 20659

Price$522,900

Est. Mortgage: $/month

Pending

MLS Number MDSM161232

  • Single Family
  • Address 42162 Woody Ln
  • Bathroom 3
  • Bedrooms 4
  • Acreage 9.27

Listed by RE/MAX 100

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42141 Woody Ln Mechanicsville MD 20659

Price$573,900

Est. Mortgage: $/month

Pending

MLS Number MDSM161226

  • Single Family
  • Address 42141 Woody Ln
  • Bathroom 3
  • Bedrooms 4
  • Acreage 9.43

Listed by Julie Cronan of RE/MAX 100

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42161 Woody Ln Mechanicsville MD 20659

Price$575,900

Est. Mortgage: $/month

Pending

MLS Number MDSM161228

  • Single Family
  • Address 42161 Woody Ln
  • Bathroom 3
  • Bedrooms 4
  • Acreage 2.05

Listed by Julie Cronan of RE/MAX 100

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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38681 Stockett Run Ln Mechanicsville MD 20659

MLS Number MDSM161216

  • Single Family
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 3920
  • Year Built 1990

This property is OCCUPIED. No showings will be available. Please DO NOT DISTURB OR CONTACT THE OCCUPANTS. The interior condition is unknown and the number of bedrooms and baths/amenities are approximate as no interior access has been made. Please contact your agent to have them register on Xome to bid on this property.

Listed by Home Source Real Estate Solutions

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27250 Tin Top School Rd Mechanicsville MD 20659

MLS Number MDSM158308

  • Single Family
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2132
  • Year Built 1979

Great Value! Brick front Split Foyer, 3 bedrooms, 3 full baths. Wood flooring in Living/Dining room. Sold AS IS. This property may qualify for Seller Financing (Vendee}.

Listed by Coldwell Banker Jay Lilly Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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23850 Hollywood Road Leonardtown MD 20650

MLS Number MDSM161174

  • Commercial Services
  • LocationType Corner Lot/Unit
  • Address 23850 Hollywood Road
  • Year Built 1948
  • Acreage 0.46

Great entry opportunity to own a stake in the storage business in southern maryland. Current cap rate is 8.53%. The ability to increase income is right there. Corner lot, cmx zoning and little vacancy. Schedule a showing today.

Listed by O Brien Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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39982 Mary Helen Way Leonardtown MD 20650

Price$334,900

Est. Mortgage: $/month

MLS Number MDSM158350

  • Single Family
  • Address 39982 Mary Helen Way
  • Bathroom 4
  • Bedrooms 3
  • Square Feet 2244

Bring your sailboat! A deeded, deep water boat slip with lift is yours with this beautiful water-oriented duplex with stunning views of Breton Bay/Combs Creek. Perfect for entertaining inside and out. Open concept main-level inc kitchen, dining, living spaces, with a beautiful water view! Lower level has custom bar and rec space with direct access to the back patio and boat slip. End-of-complex unit has nice privacy. Garage, too!

Listed by Century 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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41457 Charismatic Way Leonardtown MD 20650
Pending

MLS Number MDSM161104

  • Single Family
  • Bathroom 4
  • Bedrooms 4
  • Square Feet 3276
  • Year Built 2014

Step into this gorgeous, move-in ready, Hayden model built by Quality Built Homes. Located in popular Leonard's Grant! This awesome 4 bed/3.5 bath home features an open concept floor plan with a gorgeous eat-in kitchen, separate dining room, office with french doors, open family room, full finished basement and great fenced in back yard with stamped concrete patio. Upgraded, gleaming hardwood floors throughout the first floor. The kitchen features upgraded appliances, granite, wall oven, and a huge island with gas cooktop. Plenty of counter and cabinet space, a huge pantry, and even a built in desk. Three bedrooms upstairs including a large 18x16 owners suite with a massive walk in closet. The master bath features a soaking tub and separate walk in shower with bench and upgraded tile throughout all of the bathrooms. The full finished basement includes a 4th bedroom, full bath, and a rec room wired for surround sound and projector. There is a large unfinished storage area for all of your "extras". The back yard is fenced and features a large stamped concrete patio, perfect for little ones, pets, and entertaining. They even installed a safety gate at the top of the exterior steps to help keep little ones safe. Just steps away from the playground and a short walk to the community pool. This home has all of the upgrades and extras including lawn irrigation, tankless hot water heater, alarm system , and extra trim work and a 2 car rear load garage! Sit on the front porch and enjoy overlooking the farm land. Walk to Duke Elementary school and the new library (under construction). Walk to the Leonardtown Wharf and enjoy the local shops, restaurants, and exercise studios. A great place to live and play!

Listed by RE/MAX One

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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13785 Ryceville Rd Mechanicsville MD 20659

MLS Number MDCH200734

  • Single Family
  • Address 13785 Ryceville Rd
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2772

Over 5 private acres surround this fabulous country home! Privacy does not get much better than this! Located in a peaceful location in Charles County, you will enjoy hearing the birds and watching the wildlife! The lot offers a perfect balance of cleared land and woods. The home is a spacious 4-level split level. The main level features a spacious living room, dining room and kitchen! Upstairs features a large master suite with an attached bathroom, with separate shower and soaking tub. There are 2 other bedrooms upstairs with a hall bath. The lower level is amazing! There is a large family room with soaring ceilings! Additionally, there is the 4th bedroom/office and a half bath, a huge laundry room, and this level walks out to an enormous maintenance free deck! The basement is unfinished and is currently used for storage...with a little creativity, you can turn this space into additional living area with a game room, another bedroom, or maybe a theater room! The home offers a large 2-car garage, a front porch, and for peace mind about utility bills, this home offers a geothermal HVAC system!

Listed by O Brien Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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27075 S Sandgates Rd Mechanicsville MD 20659

MLS Number MDSM161050

  • Single Family
  • LocationType River
  • Address 27075 S Sandgates Rd
  • Bathroom 4
  • Bedrooms 4

Incredible historic home has been renovated and modernized. Home sits on majestic bluff overlooking the Patuxent River. Convenient location to PAX River, DC, shopping, and area public and private schools. Beautiful, original hardwood flooring, updated kitchen and sun room with honed granite counters, great room and master suite addition with fireplace and brick patio. Home offers gracious, level backyard with level pasture for horses, pool or any outdoor activity. Pilings for pier are currently installed. Patuxent River provides easy access to the Chesapeake Bay.

Listed by O Brien Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42187 Blacksmith Shop Rd Leonardtown MD 20650

MLS Number MDSM161054

  • Single Family
  • Bathroom 1
  • Bedrooms 2
  • Square Feet 889
  • Year Built 1955

Adorable Rambler on quiet street in Leonardtown. There is nothing to do but move in! Spend quiet evenings on your screened in front porch listening to the crickets and water flowing in the creek nearby. New carpet and paint. Newer mechanical systems, 200 AMP Electric service. Close to everything! Don't miss out.

Listed by Long & Foster Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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28790 Riverwatch Dr Mechanicsville MD 20659

MLS Number MDSM161126

  • Single Family
  • Address 28790 Riverwatch Dr
  • Bathroom 3
  • Bedrooms 4
  • Square Feet 2678

Beautiful fully remodeled colonial sitting on a tranquil 3 acre lot of flat land with detached garage! The renovations are immaculate! Greeted with 20 foot ceilings as soon as you walk into the door! A breath taking kitchen with brand new cabinets, granite countertops, stainless steel appliances, and a gorgeous island to enjoy all of your home cooked meals! Enchanting bathrooms that consists of brand new tiled floors and showers along with marble top vanities! Entire home has been freshly painted with a great combination of hardwood floors on 1st level, and brand new carpet on main and upper level. Entire crawlspace has been insulated with vapor barrier installed. A tremendous amount of space in back yard leaving you tons of possibilities to entertain! This is a MUST SEE!!

Listed by RE/MAX 100

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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40230 New Market Turner Rd Mechanicsville MD 20659

MLS Number MDSM161110

  • Single Family
  • LocationType River
  • Bathroom 7
  • Bedrooms 7
  • Square Feet 8002

This elegant Georgian Mansion ~Cellar Hill~ farm retreat, waterfront estate sits on 20 acres with breath taking water views. You will enter the center hall, striking staircases leading to the spacious 3 levels, 7 bedrooms, 5 full baths, 2 half baths, 3 kitchens, many formal and informal rooms with 5 fireplaces, finished basement and au pair quarters with own bath and kitchen. Rooftop panoramic over look heated pool, extensive brick patio, mature landscaping, small horse stable, 4' water at pier with covered boat house and boat lift. ~THIS TREASURE IS UPDATED, MODERN AND WELL MAINTAINED~ Enjoy great fishing, crabbing, endless variety of water sports and a short boat ride to Solomons Island. Close to DC, Naval Air, Patuxent River Naval Base, Technology Corridor, Schools, Shopping, Restaurants, Cultural Arts at SMCH, Wineries and is steeped in history. ~Cellar Hill~ invites you to experience the unique flavor of Tidewater life style in a setting of time less charm and grace. ~Country Quiet and City Close~

Listed by Fitzgerald Realty & Auctioneers

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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26131 Hills Dr Mechanicsville MD 20659

Price$299,900

Est. Mortgage: $/month

Active With Contract

MLS Number MDSM161134

  • Single Family
  • Address 26131 Hills Dr
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1344

Come and check out this beautiful home. This home is placed perfectly on the corner lot. Fenced in backyard for entertaining friends or relax on the front porch. This house has a huge kitchen and dining area. Good Spacious 3 bedrooms and 2 full baths. Come by and check it out!

Listed by Century 21 New Millennium

$
$
%
$/month over payments
Federal 30-year interest rate: 4.17% last updated on Apr 18, 2019
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2019 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which RE/MAX Realty Group/100 participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Data last updated April 19, 2019. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.