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Southern Garrett County & Oakland Properties

Enjoy the beauty of Mountain Maryland in Southern Garrett County! Southern Garrett County Properties includes the town of Oakland and nearby neighborhoods of Mountain Lake Park and Loch Lynn. You'll find stunning large acreage properties, commercial opportunities, and perfect primary or secondary homes! 

Contact Railey Realty with any questions about a specific property or if you’d like to schedule a showing.

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119 & 121 S 2nd St Oakland MD 21550

MLS Number MDGA2003588

  • Commercial
  • LocationType Downtown
  • Subdivision Oakland
  • Address 119 & 121 S 2nd St
  • Year Built 1914

Here is an incredible opportunity to own the ever-popular Sipside Lounge on historic 2nd Street in downtown Oakland! The possibilities are endless, offering two great spaces which are connected inside, or could be closed off as 2 separate businesses. Selling turnkey - furnished with refrigerators, icemaker, stainless steel sinks, requisite glassware, couches, barstool's, chairs and other barkeep items. The property is just oozing with history; the foundation was built in 1877 and the building itself is circa 1909. The property was completely gutted and remodeled in 2019 with the mindset to create the feeling of prohibition meets rock-n-roll. Many unique details were incorporated into the rehab project, such as stained-glass windows, stage lighting, acoustic ceiling tile, two point-out storefront displays, custom wormy oak hand-built bar, climate controlled wine storage loft, a performing arts sound system and a Bowers & Wilson Zeppelin sound system. All new flooring, bathrooms, ADA ramps, paint, electric, panel/breaker box, piping and four air conditioning units just to name a few. The upper-level is another 1,900 square feet of potential (currently being used as storage), but could also be converted to office space or a great studio apartment. If all this isn't enough, take a walk outside to the newly finished outdoor area; it will take your breath away! With approximately 2,600 square feet of covered and uncovered seating options, the hardest choice you need to make is where to sit. Perhaps you will prefer the handmade metal tables & chairs from India, or the cushioned lounge seating arrangement by the train tracks. And, one of the neatest features and biggest draws to Sipside's open-air space is the massive stone woodburning fireplace from 1938 featuring the Oakland B&O Railroad as the backdrop. So many options here! Seating capacity is 42 inside and 100 outside.

Courtesy of Taylor Made Deep Creek Vacations & Sales

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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328 Stool Rock Rd Oakland MD 21550

Oakland, MD328 Stool Rock Rd

Price$649,000

Est. Mortgage: $/month

MLS Number MDGA2003108

  • Single Family
  • Address 328 Stool Rock Rd
  • Subdivision Yough Mt. Resort
  • Bathroom 3
  • Square Feet 2040

Beautiful mountain home located in Youghiogheny Mountain Resort. This property feels private and serene from the moment you drive up. The home offers an open floor plan, hardwood flooring, two stone propane fireplaces, two family rooms and a great sun room to enjoy year round. Ideal vacation home or permanent residence. The exterior space is just as nice, offering a large wrap around deck, wonderful firepit area, trails throughout the property, natural vegetation and boulders, and a play house for kids to enjoy. The two detached garages afford you plenty of space for parking and storage. The Yough Club offers a club house, pavilion, creek and miles of riding trails. Call today to preview this great home!

Courtesy of Taylor Made Deep Creek Vacations & Sales

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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13209 Garrett Highway Oakland MD 21550

MLS Number MDGA2002104

  • Commercial
  • Year Built 1800
  • Property SubType Mixed Use
  • Acreage 37.8

Amazing Commercial Land opportunity priced to sell !!! 37.80 +/- Acres Zoned Commercial located on Garrett Highway next to Tractor Supply Oakland, Md. The property offers a mix of Commercial & Residential Development opportunities. Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems. Property has State Highway Entrance completed. New Owner would utilize this access Road to develop property. Recorded plat and Covenants available online.

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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13209 Garrett Highway Oakland MD 21550

Oakland, MD13209 Garrett Highway

Price$649,000

Est. Mortgage: $/month

MLS Number MDGA2002100

  • Land
  • Acreage 37.8
  • LocationType Pond
  • Zoning C

Amazing Commercial Land opportunity priced to sell !!! 37.80 +/- Acres Zoned Commercial located on Garrett Highway next to Tractor Supply Oakland, Md. The property offers a mix of Commercial & Residential Development opportunities. Access to Public Utilities and Natural Gas within the Town of Oakland Utility systems. Property has State Highway Entrance completed. New Owner would utilize this access Road to develop property. Recorded plat and Covenants available online.

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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131 Circle Four Ln Oakland MD 21550

Oakland, MD131 Circle Four Ln

Price$629,900

Est. Mortgage: $/month

MLS Number MDGA2003594

  • Single Family
  • Subdivision None Available
  • Address 131 Circle Four Ln
  • Bedrooms 4
  • Bathroom 2

Completely remodeled 4 Bed 2 Bath Craftsman tucked in to the hills at Deep Creek Lake. All new floors, granite tops, paint and fixtures throughout. New Stainless Steel appliances and Central Air. Resting on over 10 acres, this wooded property offers unrivaled privacy with close access to the area's 4 Season Outdoor Recreation. 10 Minutes to Oakland and 10 Minutes to Wisp, this home is centrally located to everything you want and need. Perfect for a primary or vacation home. Open floor plan with one level living. Oversized 2 car garage has plenty of space to keep your vehicles and outdoor toys out of the elements. Beautiful pond just outside the front door. If you're looking for peace and quiet, this is the home for you. Call today for details!

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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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80 Sand Flat Rd Oakland MD 21550

Oakland, MD80 Sand Flat Rd

Price$625,000

Est. Mortgage: $/month

MLS Number MDGA133628

  • Single Family
  • Address 80 Sand Flat Rd
  • Subdivision Deer Park
  • Bathroom 2
  • Bedrooms 3

26.55 Acres of multi-option property located at the corner of Sand Flat Road and Maryland Highway. The property includes a rented farm house and old barn. Access to public water and sewer available. Can be used as farm, commercial, residential, etc.

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

1094 Eagle Rock Rd Oakland MD 21550

Oakland, MD1094 Eagle Rock Rd

Price$589,000

Est. Mortgage: $/month

MLS Number MDGA2002738

  • Single Family
  • Address 1094 Eagle Rock Rd
  • Subdivision Eagle Rock
  • Year Built 2008
  • Bedrooms 5

Very impressive 5 Bedroom home on 3+ acres offers a spacious 3,700 sq. ft. open floor plan located 15 minutes to Oakland and Deep Creek Lake. Enter through the Bright Sun Room into the Great Room & enjoy the Wood Cathedral Ceilings , Gas Fireplace on the main level. His and Her private offices make it easy for multiple work spaces to work from home. The Master Bedroom suite is 30' x 20' and offers a custom tile shower your sure to remember. Your Pets will love their private indoor suite with heated floors and outdoor access. High Efficiency Heating and Cooling systems provide very nice conditioned space throughout the home. High Speed Broadband Internet provides the Home Office and TV Steamer a variety of options for work and leisure. Lots of indoor conditioned storage and a detached 24' x 40' garage finish off this property perfect for a growing family. Call today for your Private Tour.

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

185 Markwood Dr Oakland MD 21550

Oakland, MD185 Markwood Dr

Price$575,000

Est. Mortgage: $/month

MLS Number MDGA2003292

  • Single Family
  • Subdivision Meadow Lake Estates
  • Address 185 Markwood Dr
  • Bedrooms 4
  • Bathroom 2

Beautiful Mountain Home nestled in the Hills of Western Maryland! Minutes to Swallow Falls and Deep Creek Lake, this 4Bed 2Bath Mountain Lodge sits on just over 4 Acres of wooded ground, offering supreme privacy, without feeling completely off the grid. Hardwoods and rustic features throughout, with all the modern comforts of home. Open concept living area surrounds the gorgeous stacked stone wood burning fireplace, keeping you cozy in the cold winter months. Charming covered front porch and back patio add a manicured space to relax amidst the shade of mature hardwoods and fresh mountain air. Oversized two car garage to keep your tools and toys out of the elements, with double door access to the walk out basement, providing vast amounts of climate controlled storage space. Additional finished living area in the lower level makes for a perfect recreation room to accommodate you and your guests on those rainy days or evenings in. Don't miss your chance to see this Classic Four Season Mountain Retreat. Call today for your private showing!

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

4198 Maryland Hwy Oakland MD 21550

MLS Number MDGA2001122

  • Commercial
  • Address 4198 Maryland Hwy
  • Subdivision Oakland
  • Year Built 1962
  • Acreage 1.73

Incredible opportunity!! Work, live, and play all on the same property. Situated on 1.73 acres, this 5 bedroom ranch style home has recent upgrades and oozes charm. Numerous living spaces, main level living, an attached garage, AND an outdoor pool! **Brand new convenient laundry nook with sink and storage has been added off the main hallway on the main level. The basement is currently being renovated to be fully completed with two new bedrooms (bringing the total from 3 to 5) and a rec room with storage cabinets, along with existing den, bar area and full bathroom.** There is also a 4400 square foot commercial building on the property that is currently operated as Deer Park Signs. Income producing property with endless options. The business itself could also be for sale. Inquire today and schedule a private tour. Has clear road frontage & visibility, close to both Oakland & Deep Creek Lake area amenities. Prime location and lots to offer!

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

4198 Maryland Hwy Oakland MD 21550

Oakland, MD4198 Maryland Hwy

Price$575,000

Est. Mortgage: $/month

MLS Number MDGA2001118

  • Single Family
  • Address 4198 Maryland Hwy
  • Subdivision Oakland
  • Bathroom 2
  • Bedrooms 5

Incredible opportunity!! Work, live, and play all on the same property. Situated on 1.73 acres, this 5 bedroom ranch style home has recent upgrades and oozes charm. Numerous living spaces, main level living, an attached garage, AND an outdoor pool! **Brand new convenient laundry nook with sink and storage has been added off the main hallway on the main level. The basement is currently being renovated to be fully completed with two new bedrooms (bringing the total from 3 up to 5) and a rec room with storage cabinets, along with existing den, bar area and full bathroom.** There is also a 4400 square foot commercial building on the property that is currently operated as Deer Park Signs. Income producing property with endless options. The business itself could also be for sale. Inquire today and schedule a private tour. Has clear road frontage & visibility, close to both Oakland & Deep Creek Lake area amenities. Prime location and lots to offer!

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

2816 Steyer Mine Rd Oakland MD 21550

Oakland, MD2816 Steyer Mine Rd

Price$500,000

Est. Mortgage: $/month

MLS Number MDGA2000692

  • Single Family
  • Address 2816 Steyer Mine Rd
  • Subdivision None Available
  • Bathroom 2
  • Bedrooms 3

103 Acre Hunters and Fisherman's Paradise! Property is improved with a 3 bedroom/2 bathroom double wide mobile home with an attached 2-car oversized garage and an unfinished basement for storage. Also included are a barn and a hunting cabin. Laurel RunTrout Stream runs through the property. Raspberry and blackberry bushes are planted throughout the property, as well as apple and peach trees. This property is secluded enough to forget about the craziness of busy life yet still only minutes away from Deep Creek Lake activities and Oakland shopping.

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

2816 Steyer Mine Rd Oakland MD 21550

Oakland, MD2816 Steyer Mine Rd

Price$500,000

Est. Mortgage: $/month

MLS Number MDGA2003102

  • Land
  • Subdivision None Available
  • Acreage 103.93
  • Square Feet 1534
  • Bathroom 2

103 Acre Hunters and Fisherman's Paradise! Property is improved with a 3 bedroom/2 bathroom double wide mobile home with an attached 2-car oversized garage and an unfinished basement for storage. Also included are a barn and a hunting cabin. Laurel RunTrout Stream runs through the property. Raspberry and blackberry bushes are planted throughout the property, as well as apple and peach trees. This property is secluded enough to forget about the craziness of busy life yet still only minutes away from Deep Creek Lake activities and Oakland shopping.

Listed by Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 5.22% last updated on Aug 11, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

Copyright 2022 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 Railey Realty, Inc 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 August 13, 2022. 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.