East Orleans, MA Houses for Sale

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  /88

  $2,450,000

  • 4 Beds
  • 3 Baths
  • 2,615 Sq Ft

  136 Monument Rd, Orleans, MA 02653

  This classic Cape just 300 feet from the sandy beach at beloved Crystal Lake has been completely transformed by JC Donald Custom Building and Design. From its elevated setting this light-filled home overlooks a cranberry bog and offers peeks of Crystal Lake and Lonnie's Pond. There is nothing to do but move in and enjoy the lake or the new inground swimming pool and its expansive patio areas.

  Jeff Cusack Cove Road Real Estate

  136 Monument Rd, Orleans, MA 02653
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  /42

  $1,199,000

  • 4 Beds
  • 2.5 Baths
  • 2,877 Sq Ft

  43 Owl Pond Rd, Brewster, MA 02631

  ?Welcome to a home that truly has it all—space, style, and a setting that makes every day feel like a getaway. This residence has been lovingly updated and offers a layout designed for both gathering and privacy. With three separate family rooms, there's room for everyone to spread out or come together.Outside, discover your private retreat: an expansive yard with lush gardens, a relaxing hot

  Leona Bicker Gibson Sotheby's International Realty

  43 Owl Pond Rd, Brewster, MA 02631
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  /60

  $1,960,000

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft

  142 Monument Rd, Orleans, MA 02653

  Orleans Jewel with Private tennis court- This lovingly restored, meticulously maintained 1820 property sits perfectly located between two fresh water ponds and a saltwater inlet. Capturing filtered views of Pilgrim Lake, this property captures authentic charm with renovated beauty . As you move from room to room, you will admire all the thoughtful period details, beautiful floors, fantastic

  Robin Thayer Gibson Sotheby's International Realty

  142 Monument Rd, Orleans, MA 02653
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  /59

  $4,995,000

  • 5 Beds
  • 4.5 Baths
  • 3,130 Sq Ft

  5 Kidd Way, Orleans, MA 2653

  An enchanting coastal retreat! Set alongside the Pleasant Bay estuary in one of Orleans' most private & naturally beautiful enclaves, this striking 5BR/5BA custom home blends relaxed coastal living with creative design & impeccable craftsmanship.Nestled among pines, rhododendrons, and roses, the residence offers expansive water views and exceptional privacy, while just minutes from world-class

  Fran Schofield Berkshire Hathaway HomeServices Robert Paul Properties

  5 Kidd Way, Orleans, MA 2653
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  /51

  $875,000

  • 2 Beds
  • 2 Baths
  • 2,024 Sq Ft

  33 Rogers Rd, Brewster, MA 02631

  This lovely and immaculate Cape checks all the boxes! 2 large and comfortable bedrooms upstairs plus a light-filled first floor office/swing room. Open concept kitchen/dining/living room perfect for entertaining, with separate formal living room for cozy gatherings. Direct access from the kitchen onto the large sunny mahogany deck overlooking the private fenced back yard tastefully landscaped

  Ned Chatelain Chatelain Real Estate

  33 Rogers Rd, Brewster, MA 02631
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  /42

  $789,000

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft

  204 Timberlane Dr, Brewster, MA 02631

  Enjoy single floor living at its best. This newly constructed 3 bedroom 2 bath ranch style home offers a comfortable and cozy living environment . This ranch offers a wide open floor plan, consisting of a living room, office and bonus room that can be used as a guest room. Tasteful flooring throughout and a well designed kitchen,dining room combo. This newly built home comes equipped with

  Matthew Medeiros Millennium Realty Firm, LLC

  204 Timberlane Dr, Brewster, MA 02631
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  /25

  $946,000

  • 5 Beds
  • 3 Baths
  • 2,009 Sq Ft

  390 Brackett Rd, Eastham, MA 02642

  This contemporary Cape home at 390 is a one-of-a-kind home with 5 bedrooms and 3 bathrooms on a 1⁄2 acre corner lot. Nauset Light and Coast Guard Beaches, 1.5 miles away. The bike trail is 1,000 feet away. Built in 1967 the second-floor in glass allows all-day sunlight. Entering the home, oak floors and cathedral ceiling are in the living room with a spiral staircase. The front bedroom has two

  Andrew Hillman Hillman Real Estate

  390 Brackett Rd, Eastham, MA 02642
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  /49

  $1,195,000

  • 6 Beds
  • 3 Baths
  • 2,352 Sq Ft

  70 Deerfield Ln, Eastham, MA 02642

  Unique opportunity on the ocean side of Eastham. This property provides not one but TWO homes on a 3/4 acre lot. Home 1: spacious comfort with 4 bedrooms, built ins, open kitchen dinning and living areas with custom fireplace, and patio. Home 2: Ideal getaway with 2 bedrooms, home office, open kitchen living area, and deck. The spacious private yard is big enough to add a garage or pool (with

  Kimberly Clark Bayside Realty Consultants

  70 Deerfield Ln, Eastham, MA 02642
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  /30

  $3,860,000

  • 4 Beds
  • 2.5 Baths
  • 3,250 Sq Ft

  6 Snow Way, Orleans, MA 02653

  Unveil a slice of paradise at 6-12 Snow Way, Orleans, MA, offered alongside 12 Snow Way (MLS #73331530). Nestled on 1.63 captivating acres, this waterfront gem promises 3,250 sq. ft. of exquisite living space with 4 spacious bedrooms and 3 luxurious bathrooms. Relish in premium amenities such as a private outdoor oasis, a spacious garage, and exclusive waterfront access that embodies tranquility

  Patricia Pierce Compass

  6 Snow Way, Orleans, MA 02653
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  /46

  $1,049,000

  • 4 Beds
  • 3 Baths
  • 2,964 Sq Ft

  393 Thousand Oaks Dr, Brewster, MA 2631

  Set on an 1-acre lot in a quiet wooded neighborhood, this spacious Cape Cod home offers nearly 3,000 sq ft of living space, on top of an additional potential 1000+ sqft of unfinished basement that could be finished. Ideal for entertaining, it features all on the 1st floor: an open kitchen with an island & a slider connecting to a big deck, a huge vaulted ceiling family room with another slider

  Melanie Cauchon Melanie Cauchon Real Estate

  393 Thousand Oaks Dr, Brewster, MA 2631
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  /21

  $725,000

  • 2 Beds
  • 1,856 Sq Ft

  31 Monument Rd, Orleans, MA 2653

  Nestled at the end of a long meandering driveway, this very special 1.67 acres offers exceptional privacy with gorgeous mature landscaping along with a great post & beam barn that might be converted to a custom residence, an artist's oasis or guest quarters for a new home. Feel removed from it all in this very special spot that includes fruit trees and raised beds for the flower and vegetable

  Robert Wilkinson Christie's International Real Estate Atlantic Brokerage

  31 Monument Rd, Orleans, MA 2653
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  /37

  $1,200,000

  • 3 Beds
  • 3.5 Baths
  • 2,115 Sq Ft

  20 Redberry Ln, Eastham, MA 02642

  Stunning Custom Cape with Vaulted Ceilings, Multiple Decks & Private Guest SuiteWelcome to this beautifully maintained custom contemporary Cape, set on a level, landscaped lot surrounded by mature plantings, azaleas, and rhododendrons--offering exceptional privacy and natural beauty. Inside, you'll find a sun-filled kitchen with a skylight, granite countertops, porcelain sink, and tile flooring.

  Bud Macomber Meadow Marsh Inc

  20 Redberry Ln, Eastham, MA 02642
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  /57

  $3,495,000

  • 7 Beds
  • 6.5 Baths
  • 3,548 Sq Ft

  645 S Orleans Rd, Orleans, MA 02653

  For the first time in generations, this extraordinary Pleasant Bay compound--featuring the iconic ''Topside'' main residence and the charming two-bedroom ''Boathouse''--is offered as a rare, legacy waterfront estate. With a deep-water dock, moorings, and direct access to the bay, the property delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation potential. Both homes

  Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

  645 S Orleans Rd, Orleans, MA 02653
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  /67

  $1,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,000 Sq Ft

  2 Little Cove Ln, Orleans, MA 02653

  Welcome to your private backyard oasis just 1.8 miles from Nauset Beach! This beautiful home blends luxury, comfort, and style with a distinctive floor plan designed for both entertaining and relaxation.The heart of the home is the spacious, light-filled kitchen, complete with top-of-the-line appliances, a large island, and abundant lighting--perfect for gathering with family and friends. The

  Susan Sullivan Realty Consultants of Cape Cod

  2 Little Cove Ln, Orleans, MA 02653
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  /56

  $4,789,000

  • 4 Beds
  • 4.5 Baths
  • 4,311 Sq Ft

  12 Windswept Ln, Orleans, MA 2653

  Direct Ocean views from this stunning 8 room Cape on 1.34 Acres. Gorgeous grounds with incredible privacy. Beautiful custom home with 4 bedrooms & 4 1/2 baths. Tons of natural light & spectacular everchanging Ocean & marsh views with of all of its abundant wildlife.The Ocean puts on its own display of beautiful colors & sounds of waves crashing on the Nauset Beach. Fishing boats & Ocean liners

  Nikki Carter William Raveis Real Estate & Home Services

  12 Windswept Ln, Orleans, MA 2653
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  /55

  $889,000

  • 3 Beds
  • 3.5 Baths
  • 2,937 Sq Ft

  532 S Orleans Rd, Orleans, MA 02653

  Welcome to 532 S Orleans Road -- a beautifully designed contemporary home offering the perfect blend of modern comfort and timeless Cape Cod charm. This thoughtfully crafted 3-bedroom, 3.5-bath residence is nestled in a prime Orleans location tucked away from the road, close to ocean beaches (Nauset & Skaket), lakes and ponds, town landings (Pleasant Bay and Portanimicut Rd), village shops, and

  Mihaela Miteva Today Real Estate

  532 S Orleans Rd, Orleans, MA 02653
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  /55

  $899,000

  • 2 Beds
  • 2 Baths
  • 1,637 Sq Ft

  30 Grannys Ln, Orleans, MA 02653

  Proximity to Pleasant Bay in a lovely walkable and quiet neighborhood and a complete renovation makes this home a stylish and comfortable option for year round or vacation home living. Almost everything is new: quartz kitchen counters and beautiful contemporary glass tile backsplash, stainless appliances, baths, roof, 4'' wide oak hardwood floors, windows and more. Two bedrooms, two full baths,

  Christine Altneu Berkshire Hathaway HomeServices Robert Paul Properties

  30 Grannys Ln, Orleans, MA 02653
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  /66

  $985,000

  • 4 Beds
  • 3 Baths
  • 1,995 Sq Ft

  24 Old Tote Rd, Orleans, MA 02653

  Attention, investors and employers: This thoroughly renovated, legal three-family property in the center of Orleans makes for a strong income producer or tremendous employee housing. The three units are separately metered with completely new electric services and a conversion to heat pumps with a/c. The main building consists of a 1015 sq ft two bedroom first floor apartment with a living room,

  Jeff Cusack Cove Road Real Estate

  24 Old Tote Rd, Orleans, MA 02653
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  /22

  $6,250,000

  • 4 Beds
  • 4 Baths
  • 2,413 Sq Ft

  63 Old Field Rd, Orleans, MA 02653

  A rare opportunity to own a piece of Cape Cod history in the coveted Barley Neck area of East Orleans. Available for the first time in nearly 80 years, ''Sargent Point'', affectionately named after the former governor of Massachusetts, is one of the most spectacular generational waterfront properties on all of Cape Cod. This 5+ acre private retreat enjoys unparalleled panoramic views of Little

  Brian Dougherty Corcoran Property Advisors

  63 Old Field Rd, Orleans, MA 02653
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  /21

  $6,250,000

  • 4 Beds
  • 4 Baths
  • 2,413 Sq Ft

  63 Field Rd, Orleans, MA 02653

  A rare opportunity to own a piece of Cape Cod history in the coveted Barley Neck area of East Orleans. Available for the first time in nearly 80 years, "Sargent Point", affectionately named after the former governor of Massachusetts, is one of the most spectacular generational waterfront properties on all of Cape Cod. This 5+ acre private retreat enjoys unparalleled panoramic views of Little

  Brian Dougherty Corcoran Property Advisors

  63 Field Rd, Orleans, MA 02653
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  /71

  $989,000

  • 5 Beds
  • 3 Baths
  • 2,306 Sq Ft

  280 School House Rd, Eastham, MA 02642

  Nestled near the iconic National Seashore Visitor Center, this versatile multifamily property offers a unique opportunity to own a piece of Cape Cod charm with endless potential! Featuring a main house, a cozy cottage, and a spacious two-car garage with an expansive storage area above, on a large open lot, this property balances residential comfort with an investment appeal.The main house offers

  Sydney Wacht Greer Real Estate, LLC

  280 School House Rd, Eastham, MA 02642
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  /42

  $5,900,000

  • 6 Beds
  • 6.5 Baths
  • 4,000 Sq Ft

  40 Toms Hollow Ln, Orleans, MA 02662

  A rare offering on the shores of Little Pleasant Bay, 40 Tom's Hollow is a generational waterfront estate encompassing nearly four acres of bucolic landscape with an expansive shoreline, private sandy beach, and iconic boathouse. A winding drive leads through a serene coastal setting to a timeless center-entrance Colonial, where soaring ceilings and panoramic bay views set the tone. The

  Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

  40 Toms Hollow Ln, Orleans, MA 02662
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  /41

  $4,150,000

  • 4 Beds
  • 6.5 Baths
  • 5,693 Sq Ft

  20 Boat Meadow Way, Eastham, MA 02642

  Nestled on a meticulous 1.08-acre lot, this turnkey residence offers refined luxury and coastal elegance with breathtaking sunsets, panoramic bay views and nearby Boat Meadow Beach. 5,693 square feet of beautiful living space includes 4 en-suite bedrooms, a gourmet kitchen, dining area, and a living room with custom stone fireplace and expansive windows. The 1st-floor primary suite offers bay

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  20 Boat Meadow Way, Eastham, MA 02642
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  /74

  $3,299,000

  • 5 Beds
  • 3.5 Baths
  • 3,630 Sq Ft

  46 Freeman Ln, Orleans, MA 02653

  WATERFRONT with deepwater access from Rachel Cove - a protected and picturesque bay off Town Cove. This lovely, expansive Cape was built in 1995 on a private, bucolic 1.23 acre lot and has been lovingly maintained ever since by the original family. Large, welcoming foyer features raised-panel wainscoting, and warm, maple flooring which continues throughout the main living area. Transom windows

  Sarah Gammons - Ciampa Berkshire Hathaway HomeServices Robert Paul Properties

  46 Freeman Ln, Orleans, MA 02653
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  /52

  $1,900,000

  • 7 Beds
  • 8 Baths
  • 3,234 Sq Ft

  216 Main St, Orleans, MA 2653

  Now's your chance to own one of East Orleans' most iconic properties!Once home to the beloved Kadee's Lobster & Clam Bar, a bustling fish market, a welcoming gift shop, and the ever-popular Apple Grove Mini Golf, this unforgettable property is ready for its next chapter. At the heart of it all is the original family home, which later became Kadee's Gray Elephant Inn, offering classic Cape charm

  Jen Whitaker Gibson Sotheby's International Realty

  216 Main St, Orleans, MA 2653
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  /17

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,414 Sq Ft

  6 Apple Way, Orleans, MA 02653

  Beautiful .74 acre lot with deeded access to The River and shared dock for your kayaking and boating adventures. Enjoy gorgeous sunrises and sunsets overlooking meadows and mature trees. Only a 1/2 mile to Crystal Lake. Existing 2 bedroom home has been fully gutted into an amazing open floor plan that creates a great canvas for your dream home. Professionally designed plans and renderings for a

  Mary Lyttle Beach Road Properties

  6 Apple Way, Orleans, MA 02653
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  /23

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,414 Sq Ft

  6 Apple Way, Orleans, MA 02653

  From this .74 lot enjoy the setting of planted grasses and mature trees. Sit in the yard and enjoy the sunset. Only a 1/2 mile to Crystal Lake for great fresh water swimming and Pilgrim Lake is not too much farther away. This 2 bedroom home ( with 2 bedroom Title 5 system ) has been gutted allowing for a great opportunity to create a new space . Professionally designed plans and renderings

  Mary Lyttle Beach Road Properties

  6 Apple Way, Orleans, MA 02653
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  /14

  $3,295,000

  • 4 Beds
  • 3.5 Baths
  • 3,680 Sq Ft

  6 Monomoy Ln, Orleans, MA 02653

  Discover the perfect blend of modern luxury and coastal charm in this exclusive 4-property subdivision in picturesque Orleans, Cape Cod. Each of these newly constructed homes offers elegant design, top-tier finishes, and a private pool, providing the ultimate sanctuary for relaxation and entertainment. Each of these homes offers a versatile walk-out lower level, designed with high ceiling height

  LUXRECapeCod Gibson Sotheby's International Realty

  6 Monomoy Ln, Orleans, MA 02653
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  /16

  $3,595,000

  • 4 Beds
  • 3.5 Baths
  • 4,250 Sq Ft

  8 Monomoy Ln, Orleans, MA 02653

  Discover the perfect blend of modern luxury and coastal charm in this exclusive 4-property subdivision in picturesque Orleans, Cape Cod. Each of these newly constructed homes offers elegant design, top-tier finishes, and a private pool, providing the ultimate sanctuary for relaxation and entertainment. Each of these homes offers a versatile walk-out lower level, designed with high ceiling height

  LUXRECapeCod Gibson Sotheby's International Realty

  8 Monomoy Ln, Orleans, MA 02653
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  /15

  $2,995,000

  • 4 Beds
  • 3.5 Baths
  • 3,680 Sq Ft

  4 Monomoy Ln, Orleans, MA 02653

  Discover the perfect blend of modern luxury and coastal charm in this exclusive 4-property subdivision in picturesque Orleans, Cape Cod. Each of these newly constructed homes offers elegant design, top-tier finishes, and a private pool, providing the ultimate sanctuary for relaxation and entertainment. Each of these homes offers a versatile walk-out lower level, designed with high ceiling height

  LUXRECapeCod Gibson Sotheby's International Realty

  4 Monomoy Ln, Orleans, MA 02653
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  /36

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 2,377 Sq Ft

  102 Portanimicut Rd, Orleans, MA 02653

  Near the end of quintessential Portanimicut Road, in Orleans, is this unique house. Inside is the original antique homestead, an updated addition and a studio bedroom over the garage to complete the package. The antique side was built in 1880's and could become a summer art studio or guest quarters. The main updated house has a living room, dining room, galley kitchen, and a bedroom with a

  Sarah Gammons - Ciampa Berkshire Hathaway HomeServices Robert Paul Properties

  102 Portanimicut Rd, Orleans, MA 02653
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  /27

  $2,795,000

  • 4 Beds
  • 3.5 Baths
  • 5,035 Sq Ft

  2 Monomoy Ln, Orleans, MA 02653

  Modern Luxury Meets Coastal Charm in Orleans, Cape CodWelcome to an exclusive enclave of four newly constructed luxury homes in the heart of South Orleans, where timeless coastal charm meets sophisticated modern design. Nestled in a picturesque setting, each residence in this subdivision offers refined elegance, premium finishes, and a private pool--creating a sanctuary perfect for both

  LUXRECapeCod Gibson Sotheby's International Realty

  2 Monomoy Ln, Orleans, MA 02653
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  /48

  $9,500,000

  • 5 Beds
  • 6.5 Baths
  • 7,372 Sq Ft

  77 Towhee Ln, Orleans, MA 02653

  LEGACY COMPOUND WITH EXTRAORDINARY VIEWS // Pleasant Dreams is a spectacular one-of-a-kind family compound on perhaps one of the most desirable pieces of property on Cape Cod. This 2.5 acre estate boasts approximately 345 feet of saltwater frontage directly on Pleasant Bay with access to the Atlantic Ocean and showcases 180-degree breathtaking views of Pleasant Bay and beyond. This compound

  Chris Rhinesmith Compass Massachusetts, LLC

  77 Towhee Ln, Orleans, MA 02653
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  /37

  $1,800,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,973 Sq Ft

  47 Daley Terrace, Orleans, MA 2653

  Picture yourself living in your brand-new luxurious, custom-built home meticulously crafted by the highly acclaimed Eastward Companies. Conveniently located in the center of Orleans, entertaining is effortless. Your captivating cathedral great room features exquisite millwork, a fireplaced living room, a kitchen island with a spacious dining area and an adjoining vaulted light-filled sunroom.

  Anne Farley Poyant Cove Road Real Estate

  47 Daley Terrace, Orleans, MA 2653
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  /99

  $2,800,000 New Construction

  • 3 Beds
  • 5.5 Baths
  • 4,250 Sq Ft

  9 Joy Ln, Orleans, MA 2653

  This luxurious, newly completed home by Eastward Companies enjoys a quiet setting on a lightly traveled road close to Crystal Lake. Form meets function at the highest level with every detail carefully curated and an exceptional degree of custom finish work. The cathedral great room is the hub of the home, it combines the Thermador-equipped kitchen with the fireplaced living room and a generous

  Jeff Cusack Cove Road Real Estate

  9 Joy Ln, Orleans, MA 2653
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  /99

  $6,999,990 Open Sat 10AM - 12PM

  • 5 Beds
  • 8 Baths
  • 5,800 Sq Ft

  64 Pershing Ln, Orleans, MA 02653

  Mayflower Point, Orleans. This extraordinary waterfront estate on Little Pleasant Bay is now complete for Summer 2025. Eastward Companies, synonymous with Lower Cape luxury homebuilding, has exquisitely designed this 5800 sq ft shingle-style masterpiece to showcase their coastal aesthetic in a fantastic saltwater setting. The covered entry porch beckons to the main floor which is entirely

  Jeff Cusack Cove Road Real Estate

  64 Pershing Ln, Orleans, MA 02653
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  /16

  $4,995,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 4,250 Sq Ft

  10 Landers Ln, Orleans, MA 2653

  East Orleans-NEW CONSTRUCTION -4 bedroom, 3.5 bath and 3 car garage. Offering a private setting with great proximity to Nauset Beach and East Orleans village. Discover the perfect blend of modern luxury and coastal charm in picturesque East Orleans, Cape Cod. This newly constructed home offers elegant design, top-tier finishes, and a private pool, providing the ultimate sanctuary for relaxation

  LUXRECapeCod Gibson Sotheby's International Realty

  10 Landers Ln, Orleans, MA 2653
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  /79

  $4,500,000 New Construction

  • 4 Beds
  • 7 Baths
  • 5,170 Sq Ft

  44 Tonset Rd, Orleans, MA 2653

  Experience the pinnacle of sophistication with this exquisite new build by Eastward Companies which will be ready for immediate occupancy. Tucked off Tonset Road and with frontage on Main Street, this elevated home boasts lovely marsh and Town Cove views as well as swimming, fishing, and boating. This superbly designed residence features an open floor plan ideal for entertaining. The upscale

  Peg LoPresto William Raveis Real Estate & Home Services

  44 Tonset Rd, Orleans, MA 2653
• 

  

  /8

  $756,300

  • 4 Beds
  • 2 Baths
  • 1,735 Sq Ft

  42 Dyer Prince Rd, Eastham, MA 02642

  Property is being offered via Real Estate Auction on Friday, September 5 at 11am on-site. The actual selling price will be determined auction day. List price/estimated value seen is set at the real estate tax assessment. Pre-auction offers must be presented on the auction P&S and are subject to seller confirmation. 10% Buyer's Premium applies. Trustee's AUCTION: 42, 40 & 0 Dyer Prince Rd, Eastham

  Justin Manning JJManning Auctioneers

  42 Dyer Prince Rd, Eastham, MA 02642

Showing Results 41 - 79, Page 2 of 2