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Oakland MD Real Estate

Browse the latest real estate listings in Oakland MD below. You may also be interested in viewing available real estate in other Caroline County towns.

Oakland Real Estate for Sale

Call Chuck Mangold at 410-924-8832 with any questions or to schedule a private tour.

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65 Paradise Hts Oakland MD 21550

Oakland, MD65 Paradise Hts

Price$1,189,000

Est. Mortgage: $/month

MLS Number MDGA2000686

  • Single Family
  • LocationType Lake
  • Address 65 Paradise Hts
  • Year Built 1980
  • Bedrooms 3

65 Paradise Heights has 2.5 acres, excellent lake access with a boat slip, a barn style house with exposed timber framing, an open floor plan, detached two gar garage, and is in a great location but very private too.

Listed by Russell W Bounds of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Oakland Sang Run Rd 1.08 Acres Oakland MD 21550

MLS Number MDGA2001060

  • Land
  • Acreage 1.08
  • Zoning R

1.08 acre wooded building lot overlooking Oakland Golf Course. Approved Garrett County Entrance Permit on file. Lot located in Oakland Town Limits.

Listed by Richard B Orr of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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6042 Garrett Hwy Oakland MD 21550

Oakland, MD6042 Garrett Hwy

Price$525,000

Est. Mortgage: $/month

MLS Number MDGA2000862

  • Single Family
  • Address 6042 Garrett Hwy
  • Bedrooms 3
  • Year Built 1973
  • Square Feet 2729

Located 5 minutes outside of Oakland, this home offers 2 acres with pastoral views looking towards Backbone Mountain! Enjoy 3 bedrooms with 2 full baths on approximately 4000 +/- square feet of living space. Keep your feet and toys warm with radiant floor heat throughout the main level of the home and garage floors. The man cave above the garage is great for entertaining! The home is equipped with a whole house generator to keep the home functioning in the worst of winter storms or power outages. Two storage sheds outside offer plenty of room for outdoor equipment and storage. Call today to schedule a showing! This one wont last!

Listed by Nick Fratz-Orr of Railey Realty,Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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482 Pergin Farm Rd Oakland MD 21550

Oakland, MD482 Pergin Farm Rd

Price$299,900

Est. Mortgage: $/month

Active With Contract

MLS Number MDGA2001030

  • Single Family
  • LocationType Mountain
  • Address 482 Pergin Farm Rd
  • Bedrooms 3
  • Square Feet 2160

Must see this adorable and affordable log home minutes from the Deep Creek Lake, Wisp, the Historical Town of Oakland, and several State Parks. Featuring many updates throughout including luxury vinyl plank flooring, completely washed and stained exterior in last 2 years. Eat in kitchen and mudroom area perfect for dropping your ski's and snow equipment, cozy living room with Harman pellet stove to keep you warm in the winter. Lower level is a finished rec/family room/bar with a 1/2 bath. Huge covered front porch, rear patio with hot tub, fire pit and detached 2-story 2-car garage, with an oversized driveway for plenty of additional parking. This home has much to offer for every season, all of this situated on a 1.14 acre lot. Years of established rental history- perfectly named as Cozy Cabin.

Listed by Emillie H Albrecht of EXP Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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1652 Pleasant Valley Rd Oakland MD 21550

MLS Number MDGA2001046

  • Single Family
  • Year Built 1920
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1660

Located in popular Pleasant Valley this 3 to 4 bedroom farmhouse features large common area rooms with large mud room remodeled bath and main floor laundry area and large back deck for entertaining. The upper level offers 3 to 4 bedrooms and updated bath. Main level sunroom for your enjoyment. Level yard area for the the kids and plenty of space for your garden(s). Shed as well for your garden tools and supplies. Mature fruit trees on lot along with berry bushes. Heat is propane forced air with wood/coal burner in living room. New stainless steel flue as well. Home is serviced by well and septic. Interior of home needs some finishing work. Home is being offered AS IS with right to inspect. You can add your personal touches and finishes in these areas. Call for an appointment today!

Listed by Terry L Boggs of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Tall Oaks Dr #lot 2 Oakland MD 21550
Pending

MLS Number MDGA2001036

  • Land
  • Subdivision Timbers On The Yough
  • High School Southern Garrett
  • Acreage 5.31
  • Junior High Southern Middle

Timbers on the Yough lot 2. 5+ acres directly across from community river access. Approved for 3BR septic system.

Listed by Jay L Ferguson of Taylor Made Deep Creek Vacations & Sales

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Stockslager Rd #lot 36 Sandy Beach Oakland MD 21550
Pending

MLS Number MDGA2001052

  • Land
  • Acreage 1.03
  • Zoning LR
  • Association Name PATRICK MURRAY

Lot 36 Sandy Beach Properties WITH paid sewer tap. Wooded 1+ acre lot offering seasonal + filtered lake views, as well as a dedicated dock slip. Community tennis courts and 6+ acre common area. Not all lake access are created equally - Sandy Beach sets the bar high! Gorgeous lake access area with natural sandy shorelines, deep water AND rare parking area with some handicap accessibility. The lake access area is fairly level and enjoys plenty of sunshine. This is your chance to own a building lot with dockslip in a coveted and private area of Deep Creek Creek Lake.

Listed by Jay L Ferguson of Taylor Made Deep Creek Vacations & Sales

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Map 57 Parcel 80 Bray School Rd Oakland MD 21550

MLS Number MDGA2001048

  • Single Family
  • LocationType Mountain
  • Acreage 14.72

Great Price & Location! Enjoy owning 14.72 acres of heaven surrounded by peace & wildlife. The 4 BR conventional perc sits on a crest high above so you can appreciate the scenery around you. The 40'x40' existing metal shop building is fully insulated with electric and its own heat source and the lot features 1,015' of road frontage with 2 approved entrance options. Minutes away from Swallow Falls State Park & Deep Creek Lake! Additional lot may be optional for purchase, ask for details.

Listed by Amy M Zimmerman of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Map 57 Parcel 80 Bray School Rd Oakland MD 21550

MLS Number MDGA2001050

  • Land
  • Subdivision Bray School
  • Acreage 14.72
  • Junior High Southern Middle
  • LocationType Mountain

Great Price & Location! Enjoy owning 14.72 acres of heaven surrounded by peace & wildlife. The 4 BR conventional perc sits on a crest high above so you can appreciate the scenery around you. The 40'x40' existing metal shop building is fully insulated with electric and its own heat source and the lot features 1,015' of road frontage with 2 approved entrance options. Minutes away from Swallow Falls State Park & Deep Creek Lake! Additional lot may be optional for purchase, ask for details.

Listed by Amy M Zimmerman of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

20160 Garrett Hwy #a206 Oakland MD 21550
Pending

MLS Number MDGA2001044

  • Condo
  • LocationType Lake
  • Bedrooms 1
  • Year Built 1975
  • Bathroom 1

Enjoy lakefront living and the many amenities that Will O Wisp offers it's owners and guests. Sit back on your large deck/patio and take in the views of Deep Creek Lake and the surrounding mountains. During the warmer months of the year spend the day at the private beach, dock your boat at the associations docking area or take a dip in the lake. Just a short walk away you will find the popular Fire Water Restaurant and Ace's Run. In the evenings or after a day on the slopes retire to the heated pool/hot tub area. The workout area is nearby along with a sauna. Imagine the opportunities and options you can have with ownership at Will O Wisp! This unit has consistent gross rental income in the $25K range. Interior has ben totally "updated" along with a newer HVAC system. Area activities is also just a short drive away. Don't miss out on this opportunity.

Listed by Terry L Boggs of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

280 Paradise Heights Rd Oakland MD 21550

Oakland, MD280 Paradise Heights Rd

Price$2,799,900

Est. Mortgage: $/month

MLS Number MDGA2001022

  • Single Family
  • LocationType Lake
  • Square Feet 3527
  • Bedrooms 5
  • Bathroom 4

Beautifully remodeled 5 bedroom 4 bath lakefront home with Type A dock slip! Step inside and be welcomed by a gorgeous modern interior with brilliantly designed fixtures and plush furnishings. The living area flows seamlessly into the kitchen featuring stainless steel appliances. Every corner is flooded with natural light from the walls of windows. Enjoy time by the floor to ceiling stone fireplace while taking in views of the lake. The views are continued into the main level primary bedroom suite complete with vaulted ceilings and a stunning attached bath with gold finishes. Outside offers excellent entertaining spaces on the deck and stone patio. Don't miss out on this stunning lake front masterpiece! Call today!

Listed by Jonathan D Bell of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

Parcel 612 Lake Shore Drive Oakland MD 21550
Pending

MLS Number MDGA2001026

  • Land
  • Subdivision Lake Shore Drive
  • High School Southern High School
  • Acreage 3.31
  • Junior High Southern Middle

Located just off of popular lake shore, build your new lake area home on this 3.3 acre wooded site. Be a short drive to wisp resort, deep creek state park , swallow falls state park, shopping and dining. No hoa fees and deeded utility easement to property. Don't miss this opportunity. Priced well below assessed value!

Listed by Terry L Boggs of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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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Holy Cross Oakland MD 21550

Oakland, MDHoly Cross

Price$1,700,000

Est. Mortgage: $/month

Pending

MLS Number MDGA2000898

  • Land
  • Acreage 1.21
  • Junior High Southern Middle
  • LocationType Lake
  • Zoning LR

Listed by Bill G Weissgerber Jr. of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

196 Middleton Rd Oakland MD 21550

Oakland, MD196 Middleton Rd

Price$779,000

Est. Mortgage: $/month

Active With Contract

MLS Number MDGA2001002

  • Single Family
  • LocationType Lake
  • Address 196 Middleton Rd
  • Bedrooms 3
  • Year Built 2002

Great opportunity to own in the lake's best community, Blakeslee. This 3 bedroom 2.5 bath modified chalet includes lake access and a dedicated dock slip. The open floor plan offers plenty of natural light throughout the great room. The kitchen has updated stainless steel appliances and granite. Other features include: A main level primary bedroom with private bath, second floor loft with additional bedrooms, covered porches, spacious deck , and a luxurious hot tub. The level lot is perfect for activities and offers a fir pit. The level driveway makes access to the property ideal regardless of the season and weather conditions. The dedicated dock slip is an easy walk from the property. Recent upgrades include: Furnace replaced 2020, whole house dehumidifier added 2016, exterior painted 2019, hot tub added in 2019 (approximately $17,000). Blakeslee offers over 100 acres of preserved/undeveloped property offering privacy and protected views. The Blakeslee amenity package includes a community building with a large gathering area, kitchen, fireplace, indoor pool, locker rooms, deck and more. Additional amenities include 2 tennis courts, basketball court, pickle ball courts, tot lot, soccer field, trail system, private roads that are perfect for a daily walk, boat & trailer storage areas, and designated trash area.

Listed by Bill G Weissgerber Jr. of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

Lot 3 Memorial Dr Oakland MD 21550

Oakland, MDLot 3 Memorial Dr

Price$30,000

Est. Mortgage: $/month

MLS Number MDGA2001010

  • Land
  • Acreage 2
  • Junior High Southern Middle
  • Zoning NONE

Beautiful level 2 acre building lot on Memorial Drive in Oakland. Approved 3 bedroom perc. Additional 2.13 acre and 3 acre lots available. See additional listings: MDGA2001012 & MDGA2001014 (Tax ID's: 1207013701 & 1207013698)

Listed by Rachel Bruch of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

Lot 4 Memorial Dr Oakland MD 21550

Oakland, MDLot 4 Memorial Dr

Price$30,000

Est. Mortgage: $/month

MLS Number MDGA2001012

  • Land
  • Acreage 3
  • Zoning NONE

3 acre level building lot on Memorial Drive. Quiet country location, but town conveniences. 3 bedroom approved perc. See additonal listings MLS: MDGA2001014 & MDGA2001010 and Tax ID's: 1207013671 & 1207013701

Listed by Rachel Bruch of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

Lot 5 Memorial Dr Oakland MD 21550

Oakland, MDLot 5 Memorial Dr

Price$30,000

Est. Mortgage: $/month

MLS Number MDGA2001014

  • Land
  • Acreage 2.13
  • Junior High Southern Middle
  • Zoning NONE

Level 2.13 acre lot on Memorial Drive close to Broadford Park and all in-town conveniences. 3 bedroom approved perc. Additional lots available: MDGA2001012 & MDGA2001010 Tax ID's: 1207013698 & 1207013671

Listed by Rachel Bruch of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

1604 Pittsburgh Avenue Oakland MD 21550

Oakland, MD1604 Pittsburgh Avenue

Price$209,000

Est. Mortgage: $/month

Pending

MLS Number MDGA2000760

  • Single Family
  • LocationType Lake
  • Square Feet 1764
  • Bedrooms 4
  • Bathroom 2

This 4 bedroom 2 bath has been a one owner home for over 40 years. Backing to and with direct access to Broadford Park and Lake, this is the ideal property available in this price range. The back yard is private, peaceful and inviting. HVAC has recently been added. If you are looking for an affordable, well maintained home , this property is a great opportunity.

Listed by Bill G Weissgerber Jr. of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

205 Deerfield Rd Oakland MD 21550

Oakland, MD205 Deerfield Rd

Price$659,900

Est. Mortgage: $/month

MLS Number MDGA2000962

  • Single Family
  • Address 205 Deerfield Rd
  • Bedrooms 3
  • Bathroom 3
  • Year Built 2008

Enjoy the tranquil setting of this beautifully crafted Log Home located in the Deerfield Community on 1 acre of land. This 3 level, all above ground home offers 3 spacious bedrooms, 3 full bathrooms, vaulted ceilings, a loft plus a fully finished walkout basement. Just added to the lower level is one of the 3 full bathrooms, plus a finished bonus room with endless options for how you envision using it and an added 270+ square feet of living space. No detail was left out in the custom building and craftmanship of this home including 3/4" hand scraped Alder wood flooring, custom cabinetry & island, granite countertops & stainless steel appliances, a floor to ceiling wood burning stone Fireplace & rustic mantel in the cozy Living space and don't forget multiple access points to your wrap around deck space! Enjoy being close to everything the lake area has to offer while being tucked in this private wooded landscape. This home is being sold turnkey with amazing quality furnishings throughout as well as a Shed on the property for extra storage space. Make your appointment to see this lovely home soon!

Listed by Amy Webster Mangum of Railey Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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

3793 Mayhew Inn Rd Oakland MD 21550

Oakland, MD3793 Mayhew Inn Rd

Price$423,700

Est. Mortgage: $/month

MLS Number MDGA2000896

  • Single Family
  • Address 3793 Mayhew Inn Rd
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 3120

GREAT LOCATION! This Beautiful & Generously Proportioned 3 Bedroom, 3 Full Bath Home sits on 3.1+/-Acres, Watch the Gorgeous Sunsets while Relaxing on the Spacious Composite Front Deck. Enjoy the Stone Wood-Burning Fireplace in the Great Room. Nice Size Kitchen with Island, Separate Dining Area. Main Level has Bedroom #1, Separate Full Bath. Open Floor Concept. Huge Master Bedroom/Upper Level with a (16 x 4 )Walk-In Closet, Relax on the Juliette Deck Enjoying the Beautiful Views. Third Bedroom/Upper Level also has a (16 x 4 )Walk-In Closet. Working from Home, No Worries this Home has a Dedicated Office Already Set up with 2 Desks (Included). The Large Lower Level Family Room also has a Stone Wood-Burning Fireplace, Large Wet Bar with Cabinets, a Sink, Space for a Refrigerator, Microwave etc., Third Full Bath with Dual Sinks. Lower Level Laundry Room & Large Storage Room. Detached (42 x 28) Garage With Electric, Two 10 Foot Garage Doors with Electric Openers, Poured Concrete Walls that are Insulated. Bonus Room Above the Garage Could be Finished Off for a Game Room (42 x 14). This is a Must See Property to Take In All that it Offers. Take a Stoll just down the Road & Go Horse Back Riding at Western Trails, Enjoy Deep Creek Lake State Park, Swallow Falls & Herington Manor State Park just minutes away. You are Just Minutes From All of DEEP CREEK LAKES AMENITIES! Don't Feel Like Cooking that's Okay, Enjoy the Delicious Food at JG's Pub within a 1/4 mile. Call Today to Set up a Showing to View This FANTASTIC PROPERTY!

Listed by Debra A Beitzel of Long & Foster Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.88% last updated on Sep 23, 2021
* 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 2021 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 Chuck Mangold 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 September 24, 2021. 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.

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