Oak Bluffs Homes from $1M-$3M

Search with Sandpiper Realty, Inc. to find current luxury homes, between $1M-$3M, for sale in Martha's Vineyard's town of Oak Blufss. Look through a variety of listings to find your new home. Register with us to save your favorite properties, and you can get email updates when new listings match your search criteria.

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71 Pennacook Avenue, Oak Bluffs, MA

Price$1,149,000

Est. Mortgage: $/month

MLS Number 33425

  • Residential
  • Square Feet 2108
  • Bedrooms 6
  • Bathroom 2
  • Half Bath 1

CLASSIC BEAUTY IN THE HEART OF OAK BLUFFS, The Pennacook House is set on a slight hill on a large landscaped yard. this YEAR ROUND 6 bedroom, 2.5 bath home has a lovely eat-in kitchen, formal dining and living rooms with bay windows, den/study, hardwood flooring, outdoor shower, gorgeous period details and many updates throughout. Brand new propane hot water and heating system. Full walk-out basement with laundry and plenty of storage space. Home is sunny and warm in the winter and catches the cool summer breezes. GREAT LOCATION just a few blocks to town center, ferry, Ocean Park, and beaches. VERY STRONG RENTAL HISTORY!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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10 Paddock Road, Oak Bluffs, MA

Price$2,520,000

Est. Mortgage: $/month

MLS Number 33638

  • Residential
  • Square Feet 4000
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

Under Construction: 4000 sq ft of brand-new construction tucked nicely on a beautiful lot in the prestigious subdivision of "The Preserve". This home meets all the modern buyer's needs with its open floor plan, 1st and 2nd floor master bedroom suites, chef's kitchen, hardwood floors throughout, custom tile bathrooms, expansive outside entertaining space, and lush landscaping. This is a "family compound in the making," a swimming pool and poolhouse may also be installed if a buyer chooses to do so. With its generous living spaces this home is ideal for entertaining friends and family. There is also lots of opportunity for privacy, thanks to the separate bedroom suite and bathroom above the garage. This is the summer house of your dreams, and can also be your escape during the cooler months thanks to the modern, efficient systems. This spectacular home will be the ideal place to host large family dinners at Thanksgiving or the holiday season with the fireplace as the perfect setting to gather round at the end of the day. To be completed in the Fall of 2018. ***** interior pictures shown are of a similar house built by the builder to give you an idea of quality and finishes.

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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33 Beach Road, Oak Bluffs, MA

Price$1,500,000

Est. Mortgage: $/month

MLS Number 34185

  • Residential
  • Square Feet 1622
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.1899

Smell it! Feel it! Taste it...the sea that is! Waterfront 3 season cottage looking westerly over Vineyard Haven Harbor. Sunsets and sailboats everyday plus a DEEPWATER DOCK for all your boating needs. Originally known as "Station #7" of the NY Yacht Club, this historic home was used "back in the day" to give club members a comfortable place to tie up their tenders and step ashore while sailing the waters around the Vineyard. Classic cottage appeal inside and out.

Listed by RE/MAX on Island

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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227 Buddys Drive, Oak Bluffs, MA

Price$1,070,000

Est. Mortgage: $/month

MLS Number 33978

  • Residential
  • Square Feet 2762
  • Bedrooms 6
  • Bathroom 3
  • Half Bath 1

The PERFECT CHOICE for your FAMILY VACATION HOME/YEAR ROUND RESIDENCE ! ONE OWNER ~CUSTOM COLONIAL offering an UPDATED & RENOVATED BRIGHT & SUN FILLED GREAT ROOM with expansive living/dining area and NEWER kitchen with STAINLESS STEEL APPLIANCES & GLEAMING GRANITE COUNTERS! The interior of the home is inviting and generous with an abundance of ROOMS! This open design has striking natural wood ship lap ceilings. Glass doors offer access to a huge exterior deck and penetrating views into the abutting State Forest ...The attention to detail includes the luxury of 2 Master Suites, on the first floor and second floor.There is a total of 6 bedrooms, 3. 5 bathrooms and a huge unfinished space above the two bay garage!..STRONG EXISTING RENTAL HISTORY in PLACE! OUTSTANDING LOCATION & TERRIFIC VALUE! ROOM for a POOL TOO! here is a break down of square footage 1st floor sf 1820 2nd floor sf 1280 3rd floor sf 520 Total current finished SF 3620 Above garage unfinished sf 750 Total possibly finished SF 4370 Additional current spaces. Basement sf 1428 Two car Garage sf 550

Listed by Ocean Park Realty Inc

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Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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90 South Circuit Avenue, Oak Bluffs, MA

Price$1,669,000

Est. Mortgage: $/month

MLS Number 33863

  • Residential
  • Square Feet 2780
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.33

Oak Bluffs: Custom design in special location just a short walk to town and public beach...but offering Up Island Privacy with views over Farm Pond, barrier beach and Nantucket Sound to the Southeast and over a cedar meadow to the Southwest. Bright great room with high ceilings lots of South facing glass, intimate sitting arrangements, large beamed dining room, great kitchen and pantry, broad sunny deck, huge bedrooms, new roof, marble vanities in the bathrooms, 2 car garage with loft storage, wonderful outside shower. Heat Pump AC mini splits throughout! RARE OFFERING & ONE of A KIND LOCATION!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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7 Old Harbor Lane, Oak Bluffs, MA

Price$2,632,500

Est. Mortgage: $/month

MLS Number 33797

  • Residential
  • Square Feet 2488
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.547

Waterview Farms Opportunity: One of the most spectacular vistas of Sengekontacket Pond and Nantucket Sound. Beautifully landscaped with specimen plantings, perennial hydrangea, seasonal flowers, and semi bordered by stone walls. Open floor plan, large living room, kitchen with granite counter tops, and stainless appliances. Living room opens to a large deck with hot tub. Contemporary ranch with four bedrooms and four full baths. Three of which are suites. Adjacent to "Farm Neck” is the 3rd green… Short stroll through the meadow leads to the beach access for water sports. ( 24 hr notice required for showings due to summer rentals)

Listed by Island Home Realty Inc.

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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311 East Chop Drive, Oak Bluffs, MA

Price$2,250,000

Est. Mortgage: $/month

MLS Number 33800

  • Residential
  • Square Feet 1496
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Smell the sea and touch the sky from this unique vintage waterfront home on East Chop. Extraordinary views of Vineyard Sound from every room with ocean breezes flowing through to Crystal Lake. You can watch the sun rise as you bathe in the antique tub and then watch the sun set from the patio or master suite. Your private 120' dock, mooring and sandy pebbled beach are the perfect place to enjoy all the beauty and water activities that make the Island a special place for generations of family memories. On the ground floor there is an open floor plan with a central kitchen, living and dining area flanked by two bedrooms. The master bedroom is en-suite with a sitting area that opens up to spectacular views of the blue water. The second bedroom on the first floor is a cozy enclave with a private half bath. The open kitchen has ample room to prepare breakfast, lunch and dinner - eat in the attached dining nook or alfresco on the brick patio. Upstairs there are two additional bedrooms and a full bath. There is a detached garage with a large cedar-lined closet for storage. This magnificent home is located within walking or biking distance of downtown Oak Bluffs. Being offered turnkey and has a solid rental history.

Listed by Coldwell Banker Landmarks

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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283 East Chop Drive, Oak Bluffs, MA

Price$1,699,000

Est. Mortgage: $/month

MLS Number 33651

  • Residential
  • Square Feet 2456
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

Private beach on East Chop with gorgeous water views of the Vineyard Sound from each room, including all bedrooms! Quintessential Vineyard shingled house right on the water; swim, kayak or watch the ferry and boats from your private deck or porch just a few steps to the Sound. 2456 square foot house with four bedrooms (two of them enormous), two and one half baths, large separate laundry room, open floor plan to include fully equipped kitchen, dining room and living room with a large stone fireplace, all with stunning water views. Second floor family room and ample closet space in every bedroom. Enjoy countless hours relaxing on the side deck with outdoor living space in addition to the new stone patio for all your grilling needs. Convenient to both Oak Bluffs, Vineyard Haven and to the Telegraph Hill Lighthouse. Perfectly situated within one mile of East Chop Beach Club, Yacht Club and Tennis Club. Great rental history too. This home will not disappoint.

Listed by Anchor Realty of Martha's Vineyard

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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117 Barnes Road, Oak Bluffs, MA

Price$1,200,000

Est. Mortgage: $/month

MLS Number 33648

  • Residential
  • Square Feet 560
  • Bedrooms 2
  • Bathroom 1
  • Acreage 1.2099

Moved to the current site in 1916 this charming cottage offers expansive views of the Lagoon and outer harbor. Known as "The Outlook" the views extend past West Chop to the Cape. A wraparound porch provides the perfect spot for relaxing, either with a good book or an al fresco meal. Grab a front row seat and enjoy the spectacular sunsets. The comfortable living/dining room, kitchen and two bedrooms and bath, plus outdoor shower, provide a carefree get away. Walk down the path to the 100+ feet of beach. Pull up your kayak or moor your boat. This is summer living at its best.

Listed by Coldwell Banker Landmarks

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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42 Paddock Road, Oak Bluffs, MA

Price$1,999,000

Est. Mortgage: $/month

MLS Number 33543

  • Residential
  • Square Feet 4200
  • Bedrooms 5
  • Bathroom 4
  • Half Bath 1

OAK BLUFFS - new, luxury enclave - The Preserve at the Woodlands! Enjoy the best of both worlds in this lovely area abutting 200 acres of conservation land yet centrally located off County Road near Farm Neck Golf Club with bike paths that provide EASY ACCESS into downtown Oak Bluffs, Edgartown and Vineyard Haven. Relax and enjoy POND VIEWS and panoramic meadow views. This HIGH QUALITY NEW CONSTRUCTION offers 5 bedrooms and 4.5 bathrooms with 9 foot high ceilings. The wooded 1.8 acre lot offers a spacious backyard with a bluestone patio for entertaining, outdoor shower and borders conservation land for complete privacy. The option to add a POOL is available upon request. An OPEN FLOOR PLAN features a large gourmet kitchen with a Sub-Zero fridge, Wolf range and other professional stainless steel appliances. The living and dining area has lovely views of the pond, custom built-ins and a gas fireplace. A first floor master bedroom contains an en suite bath, dressing area and walk-in closet. For your convenience, there is a first floor laundry room, mud room and powder room. Upstairs there are four SPACIOUS bedrooms - two of which are master bedrooms with en suite baths and vaulted ceilings. The two additional bedrooms share a hallway bathroom with double sinks. Two of the bedrooms offer pond views. There is an additional washer and dryer upstairs. Enjoy UP-ISLAND PRIVACY with DOWN-ISLAND CONVENIENCE! Don't miss this opportunity to enjoy this beautiful INVESTMENT property and begin to earn income right away. Or enjoy it all year round yourself with family and friends!! MOVE IN READY!!

Listed by Ocean Park Realty Inc

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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32 Harthaven Road (formerly 72), Oak Bluffs, MA

MLS Number 19565

  • Residential
  • Square Feet 2990
  • Bedrooms 4
  • Bathroom 4
  • Half Bath 1

Harthaven Gem. Beautiful Colonial-style home is located in desirable Harthaven and has access to association beaches, private small boat harbor, tennis and more. This lovely home features 4 bedrooms with private baths and walk-in closets. Enjoy your evenings on the spacious, screened-in porch overlooking acres of conservation land. There is a spacious living room with sliders to the porch. Kitchen has granite counters and ample storage. It opens to the dining area and porch perfect for entertaining. Office/family room in lower level. Home has many special features including central air conditioning, ceiling fans, alarm, irrigation and more. Two-car attached garage. Property abuts Tradewinds, a 71 acre land bank property. Very successfully rental history. Home is being sold turn-key.

Listed by Island Real Estate

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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20 Bayes Hill Road, Oak Bluffs, MA

Price$1,050,000

Est. Mortgage: $/month

MLS Number 33198

  • Residential
  • Square Feet 2401
  • Bedrooms 3
  • Bathroom 3
  • Half Bath 1

Bayes Hill Charmer...Three bedroom three and a half bath home surrounded by lovely perennial gardens with a wonderful open porch on the front and large private deck across the back of the home.

Listed by Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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15 Dover Street, Oak Bluffs, MA

Price$2,295,000

Est. Mortgage: $/month

MLS Number 32913

  • Residential
  • Square Feet 3800
  • Bedrooms 5
  • Bathroom 4
  • Acreage 0.35

Water views, lots of square footage, prime location, and a big bedroom count - you get all this and more in this stunning home. Even in a neighborhood of such substantial properties, 15 Dover Street has the ability to turn heads. This grand dame of East Chop surveys the harbor and all else from her elevated position. The residence is perfectly at ease in this area of classic antique homes, but was actually constructed in 1998 by a respected Island builder who took his inspiration from the distinguished shingled homes that are found in the more desirable enclaves of Martha's Vineyard. As soon as you step inside it becomes apparent that this is a very modern home with wide-open living spaces, multiple entertaining areas, two master bedroom suites, a renovated gourmet kitchen and bathrooms, hardwood floors, and a double-sided fireplace. The huge picture windows accentuate the water views and make it feel like you could reach out and touch the ferries passing by. Other important amenities include central AC, a modern 2-car garage, and a full basement. All the bedrooms are generously proportioned, and three of them have private decks. The landscaping and gardens are the perfect complements to the property. As you would expect, such a home is in extremely high demand by summer visitors, and so it generates a very handsome rental income. The home is easy to show during the off-season and comes completely furnished. Abundant waterviews - watch our video https://vimeo.com/245739832

Listed by Wallace & Co. Sotheby's

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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28 Beach Road, Oak Bluffs, MA

Price$1,595,000

Est. Mortgage: $/month

MLS Number 32752

  • Residential
  • Square Feet 1800
  • Bedrooms 4
  • Bathroom 2
  • Half Bath 1

VIEWS, VIEWS & MORE VIEWS! Designed to not only capture the views of Vineyard Sound and beyond to Woods Holes as well as a straight shot down the Lagoon, but this home was also created to be a comfortable home for year-round and summer living. Newly built 4 bedroom/2.5 bath home has commanding views from almost EVERY room with 2-levels of covered decks on the Vineyard Sound side of the home and 2-levels of decks on the Lagoon side. First level features 3 bedrooms, spacious family room, a full bath with laundry and ample storage. The second level features a sun-drenched open floor plan with a gourmet kitchen with stainless Thermador appliances, Silestone counters and an abundance of cabinets. Take in the long view down the Lagoon from the living area with gas fireplace and custom mantel. The master en suite has high ceilings with bathroom features that include a double-sink vanity with marble counters and glass shower enclosure finish this level of the home. There are sliding doors on both levels that open to the front and side decks. High-efficiency heat pump system, central air and more. Home is ready for you to pack your bags and move in. Did we mention the views? Come tour this unique home and see them for yourself. Home is being sold furnished.

Listed by Island Real Estate

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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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14 Temahigan Avenue, Oak Bluffs, MA

Price$2,950,000

Est. Mortgage: $/month

MLS Number 32282

  • Residential
  • Square Feet 4821
  • Bedrooms 7
  • Bathroom 3
  • Half Bath 2

Historic Water View Home with views of endless sunsets and sailboat races! On the market for the first time in over 50 years. Originally built in 1915, this stately Dutch Colonial has been enjoyed as a family gathering and celebration place every summer. Everything about this house....the 7 bedrooms, grand foyer, imposing dining and living rooms (both with water view), the original hand crafted woodwork details and the full length wrap around covered veranda overlooking West Chop and Vineyard Sound....will help you create your own family legacy and memories on the island. You will be amazed by the classic architecture of the home and the sweeping back yard inviting games for the young and old alike. A deeded walkway to the beach is included where you can keep a dingy to row out to your moored boat, sit and watch the sun set over West Chop or take a quick dip in the Sound. Remember...this is a home where porch parties are a must!

Listed by RE/MAX on Island

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$
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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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112 Park Street, Oak Bluffs, MA

Price$1,755,000

Est. Mortgage: $/month

MLS Number 30743

  • Residential
  • Square Feet 2100
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.31

WATER VIEWS and SPECTACULAR SUNSETS are yours from this gorgeous, FULLY FURNISHED, East Chop home nestled on a large double lot in this highly desirable neighborhood. This dazzling home offers classic charm with modern, luxury amenities. The 75 ft. wrap around deck and covered dining rotunda were built for enjoying true Vineyard living. This home has 4 bedrooms and 3 full bathrooms with marble, custom tile and original hard wood floors. Incredible customized high end kitchen and cozy sunroom have double french doors that opens onto a pergola covered deck creating a flowing indoor/outdoor living experience. Make this your year round home or keep as an investment property with over $70,000 a year of rental income in place. Your Island Dream Home Awaits.

Listed by Laer Realty Partners

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$
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$/month over payments
Federal 30-year interest rate: 4.65% last updated on Sep 20, 2018
* 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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