Homes for Sale near The Family School

• 

  

  

  /70

  $2,000,000

  • 3 Beds
  • 2 Baths
  • 2,129 Sq Ft

  60 Smith Heights Way, Eastham, MA 02642

  Enjoy coffee and the sunrise on the back porch overlooking the water, or evening sunset refreshments on the screened-in porch. Head down the stairs to the water and dip your toes in the water or the sand. One bedroom on the upper level with an additional loft space and a full bathroom, with beautiful custom built-ins perfect for your home library, with amazing water views. The main level is

  

  Eric Rollo

  The Agency Boston

  (508) 504-7582

  60 Smith Heights Way, Eastham, MA 02642
• 

  Explore The Family School

• 

  

  

  /36

  $299,000

  • 1 Bed
  • 1 Bath
  • 868 Sq Ft

  42 Old Colony Way Unit 30, Orleans, MA 02653

  Situated in the vibrant heart of Orleans, you'll find yourself just steps away from an array of restaurants, boutiques, Gyms, Farmers market and shopping.The nearby artist studios provide a unique window into the region's thriving art scene, ensuring there's always something new and exciting to explore. For those who love cycling, the proximity to the bike path is a true highlight.This

  

  Kimberly Clark

  Bayside Realty Consultants

  (508) 625-9581

  42 Old Colony Way Unit 30, Orleans, MA 02653
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  /75

  $1,549,000

  • 3 Beds
  • 3 Baths
  • 2,110 Sq Ft

  188 Rock Harbor Rd, Orleans, MA 02653

  Exquisitely Renovated 1830 Greek Revival estate on 1+ acre... Step into timeless elegance blending historical charm with modern updates. Known as the historic Jabez Sparrow Homestead and set on a level and meticulously maintained 1.04-acre lot in a prime near beach location.Inside, the home features a desirable first-floor primary suite with spacious, brand new, modern full bathroom. Two

  

  Barbara Garside

  eXp Realty, LLC

  (508) 719-6484

  188 Rock Harbor Rd, Orleans, MA 02653
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  /69

  $2,395,000

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  240 Robbins Hill Rd, Brewster, MA 02631

  Bayfront Brewster- Located in one of Brewsters premier bay locations. The residence offers direct access to your own beach. this classic Cape Cottage style beach house has been updated, but still has that classic Cape Cod beach house charm of yesteryear. The residence has 3 bedrooms, 2 updated baths, ductless heat and ac, backup generator, detached shed for all those beach toys and more!

  LUXRECapeCod Gibson Sotheby's International Realty

  240 Robbins Hill Rd, Brewster, MA 02631
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  /42

  $1,650,000

  • 9 Beds
  • 8.5 Baths
  • 4,503 Sq Ft

  2705 State Hwy, Eastham, MA 2642

  An excellent investment opportunity in Eastham, 2705 State Hwy features an 8-unit, year-round multifamily complex with strong rental history and multiple paths for future value. Ideally located near Salt Pond, the Eastham Rec Department, and Coast Guard Beach, it offers dependable income in a consistently high-demand market. The property includes 6 buildings—2 duplexes and 4 standalone

  Mason Hickman eXp Realty

  2705 State Hwy, Eastham, MA 2642
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  /42

  $244,900

  • 1 Bed
  • 1 Bath
  • 579 Sq Ft

  60 Fletcher Ln Unit H, Brewster, MA 02631

  Live the Cape Cod dream at 60-H Fletcher Lane! This sunny 1-bedroom end unit in Ocean Edge is all about location and lifestyle—steps to pools, fitness, and golf. Enjoy morning coffee or sunset cocktails on your private garden-level patio overlooking the fairway. Inside, fresh paint, new stainless appliances, new kitchen counters, new carpet in livingroom and easy-care new laminate floors create a

  Chelsea McLaughlin RE/MAX Legacy

  60 Fletcher Ln Unit H, Brewster, MA 02631
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  /63

  $4,999,000

  • 4 Beds
  • 3 Baths
  • 3,867 Sq Ft

  66 Tides End Ln, Orleans, MA 02653

  Here's your chance to own property in coveted East Orleans with a private deep-water dock, access to Meeting House Pond, Namequoit River, Little Pleasant Bay, Pleasant Bay and the Atlantic Beyond. Anchored on a sprawling 2.6 acres a mere 2.4 miles to world renowned, Nauset Beach, this stately property is graced by the embrace of water on three sides, showcases a rolling meadow of lawn space, and

  Cape Cod Power of Two Compass

  66 Tides End Ln, Orleans, MA 02653
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  /27

  $285,000

  • 1 Bed
  • 1 Bath
  • 252 Sq Ft

  1061 State Hwy Unit 4, Eastham, MA 02642

  Step into your very own Cape Cod escape. This sun-filled studio condo blends seaside charm with easy living, just minutes from both bay and ocean beaches. Over the past few years, the cottage has been thoughtfully updated, including a renovated kitchen and bath, vinyl plank flooring, new outdoor shower, new appliances, a 40-gallon water heater, 100-amp electrical service, freshly painted

  Sherri Simms Kinlin Grover Compass

  1061 State Hwy Unit 4, 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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  /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
• 

  

  /29

  $410,000

  • 2 Beds
  • 2 Baths
  • 935 Sq Ft

  52 Eaton Ln Unit (52), Brewster, MA 02631

  Experience all that Ocean Edge has to offer in this turnkey condo that is being sold FULLY FURNISHED - perfect for your Cape getaways, as an investment property, or as a year-round residence. Located on the upper level with a view of the second tee from the covered rear deck, this surprisingly spacious unit features a cathedral-ceiling living room, a master bedroom with private bath, one

  Shepard Long Advocate Realty/Stikeleather Real Estate

  52 Eaton Ln Unit (52), Brewster, MA 02631
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  /3

  $200,000

  • Land
  • 0.92 Acre
  • $217,391 per Acre

  0 S Orleans Rd, Harwich, MA 02645

  Undevelopable Land per the Town of Harwich. Property could be sub-divided into 4 10,000 s.f. increments for bedroom credits as part of the Nitrogen Loading Credits program so an additional bedroom can be added to another property in Harwich.

  Doug Grattan Christie's International Real Estate Atlantic Brokerage

  0 S Orleans Rd, Harwich, MA 02645
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  /21

  $2,200,000

  • 3 Beds
  • 2 Baths
  • 1,988 Sq Ft

  20 Billingsgate Ave, Eastham, MA 02642

  Located in the desirable Target View Association with deeded beach rights and easy access to Cape Cod Bay, this fully remodeled 3-bedroom, 2-bath Cape offers modern finishes, central AC, and quality systems throughout. The main level features an open layout with hardwood floors, oversized windows, a quartz kitchen, a gas fireplace, and a first-floor primary bedroom, all served by gas heat and a

  Barbara Francke Kinlin Grover Compass

  20 Billingsgate Ave, Eastham, MA 02642
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  /26

  $1,550,000

  • 4 Beds
  • 2 Baths
  • 1,825 Sq Ft

  9 Honeysuckle Ln, Orleans, MA 02653

  Nestled on a quiet road shared by only six homes, this beautifully renovated 2024 property offers the perfect mix of privacy, comfort, and coastal charm. Just a short stroll from Skaket Beach, it's a place where you can unwind, soak in the sunsets, and enjoy the best of Orleans living.The thoughtfully designed reverse floor plan places four comfortable bedrooms with plenty of storage on the main

  Liz Holguin Classic Cape Real Estate, LLC

  9 Honeysuckle Ln, Orleans, MA 02653
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  /83

  $2,250,000

  • 4 Beds
  • 4 Baths
  • 4,067 Sq Ft

  34 Lake Dr, Orleans, MA 02653

  Set within the coveted Quanset Harbor Club, this oversized Cape sits at the end of a long private drive framed by mature plantings and tranquil pond views. The neighborhood offers exceptional amenities, including a private Pleasant Bay beach with dock, kayak rack, and exclusive mooring field, along with direct access to conservation land and scenic hiking trails--an unmatched blend of recreation

  Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

  34 Lake Dr, Orleans, MA 02653
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  /74

  $3,199,000

  • 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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  /37

  $1,899,000 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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  /29

  $849,000

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

  274 Commons Way, Brewster, MA 02631

  Thoughtfully Designed 3-Bedroom Home with Spacious Kitchen & Sunlit Living Room Welcome to this 3-bedroom, 2.5-bath single-family home, thoughtfully laid out to balance comfort and functionality. The large kitchen features vaulted ceilings, quartz countertops, stacked ovens, and a countertop range on the island—ideal for both everyday cooking and entertaining guests. The living room is bright and

  Ken Hager Classic Cape Real Estate, LLC

  274 Commons Way, Brewster, MA 02631
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  /62

  $975,000

  • 3 Beds
  • 3 Baths
  • 2,623 Sq Ft

  33 Pine Orchard Rd, Harwich, MA 02645

  Set in one of Harwich's most coveted pockets, this home offers rare proximity to everything that defines Cape Cod living.Inside, the effortless single-level layout centers on an open great room where living, dining, and a beautifully appointed kitchen flow together. A grand island, multiple prep sinks, and a gas cooktop make the space ideal for both gatherings and everyday cooking. A gas stove

  Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

  33 Pine Orchard Rd, Harwich, MA 02645
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  /42

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,105 Sq Ft

  277 Lund Farm Way, Brewster, MA 02631

  Unique 2151sqft 4-BR 2Ba post & beam w/deeded association beach rights on Blueberry Pond. Built with reverse floor plan, top to bottom back wall full of windows overlooking Blueberry Pond, this house used to have year-round water views that could be brought back w/pruning. Very open floor plan, high vaulted beamed ceiling, huge living room w/fireplace,French doors to the back deck & private yard.

  Melanie Cauchon Melanie Cauchon Real Estate

  277 Lund Farm Way, Brewster, MA 02631
• 

  

  /31

  $949,900 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,102 Sq Ft

  5 Reilly Run, Orleans, MA 02653

  Introducing a new 9-unit detached condominium community in Orleans on Cape Cod, offering move-in ready homes thoughtfully designed for easy living and including a first floor bedroom suite. Nestled in a quiet setting, this neighborhood provides direct access to the Cape Cod Rail Trail, providing effortless access to over 25 miles of scenic pathways and Main Street. Brand new, energy efficient and

  Sarah Dacey Champion Realty Group, LLC

  5 Reilly Run, Orleans, MA 02653
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  /42

  $669,900

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft

  76 Williamsburg Ave, Harwich, MA 02645

  Welcome to this beautifully maintained 4-bedroom, 2-bath Raised Ranch that offers Cape Cod charm with modern comfort in a peaceful residential setting. In turn-key condition, this home provides exceptional flexibility as a primary residence, second home/ vacation retreat, or investment property with strong rental history. The light-filled interior features a welcoming living room with a cozy

  Nichole Willey Keller Williams Realty

  76 Williamsburg Ave, Harwich, MA 02645
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  /63

  $1,800,000

  • 3 Beds
  • 2.5 Baths
  • 2,513 Sq Ft

  15 Morgan's Way, Orleans, MA 02653

  Perched at the top of a private 1-acre lot, this newer home checks all of the boxes! The 1st floor primary bedroom suite features a walk-in closet and en suite bath with a walk-in shower and double sink vanity. The great room is the ultimate gathering place, with its open plan blending the kitchen, dining, and living areas. Enjoy vaulted ceilings, a palladium window, built-ins, wide oak floors,

  Amy Harbeck Kinlin Grover Compass

  15 Morgan's Way, Orleans, MA 02653
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  /39

  $1,469,000

  • 5 Beds
  • 10 Baths
  • 11,000 Sq Ft

  558 Fox Hill Rd, Chatham, MA 02633

  Co-ownership opportunity. Fox Hill, a spectacular waterfront retreat sited proudly on nearly 3 acres in a coveted North Chatham location! Within steps to a private beach and dock, this custom shingle residence was designed to accommodate large summer gatherings or cozy weekend getaways! Stunning views of Crows Pond, Eastward Ho and Pleasant Bay can be enjoyed throughout the property, while a

  Brian Dougherty Corcoran Property Advisors

  558 Fox Hill Rd, Chatham, MA 02633
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  /75

  $1,998,000

  • 3 Beds
  • 3.5 Baths
  • 2,664 Sq Ft

  20 Kittiwake Ln, Eastham, MA 02642

  Spacious Waterfront Retreat with 3 Private Bedroom Suites with Shared Dock AccessThis beautifully designed home offers three private bedroom suites, each with its own en-suite bathroom, providing comfort and privacy for every guest. Tucked away in a secluded, tranquil setting, it's perfect for peaceful living or entertaining with ease.Inside, you'll find plenty of living space to relax or gather,

  Kimberley Vitale William Raveis Real Estate & Home Services

  20 Kittiwake Ln, Eastham, MA 02642
• 

  

  /31

  $2,499,000

  • 4 Beds
  • 2.5 Baths
  • 2,539 Sq Ft

  11 Little Marsh Ln, Orleans, MA 2653

  Set on the serene banks of the Namequoit River with 235' of frontage and dock, an inviting blend of light, space, and waterfront living. This 4-bedroom, 2.5-bath home captures the essence of Cape Cod with sun-filled interiors, thoughtful design, and multiple outdoor spaces designed for relaxation.Inside, natural light streams through expansive windows, highlighting the open floor plan and framing

  Ken Hager Classic Cape Real Estate, LLC

  11 Little Marsh Ln, Orleans, MA 2653
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  /41

  $550,000

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft

  43 Billington Ln, Brewster, MA 02631

  On this sunny morning, this ''A'' style townhome is bathed in natural light within the beloved Ocean Edge Resort. Billington Lane facilitates convenient ingress and egress from the resort via route 137. Positioned away from the main thoroughfare, it provides a tranquil and secluded outdoor living space. As the largest of the three townhouse styles, this condominium features two full bathrooms,

  Leighton Team Keller Williams Realty

  43 Billington Ln, Brewster, MA 02631
• 

  

  /44

  $399,900

  • 2 Beds
  • 2 Baths
  • 935 Sq Ft

  78 Eaton Ln Unit 78, Brewster, MA 02631

  Welcome to your serene second-level garden condominium, where modern elegance meets comfort. This stunning 2-bedroom, 2-bathroom home boasts an upgraded kitchen featuring sleek granite countertops and abundant counter space, perfect for culinary enthusiasts. Enjoy the airy open-concept layout, accentuated by vaulted ceilings and beautiful hardwood flooring and new carpeting. Step outside to your

  Brian Balestracci Milestone Realty, Inc

  78 Eaton Ln Unit 78, Brewster, MA 02631
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  /42

  $3,400,000

  • 5 Beds
  • 1 Bath
  • 1,904 Sq Ft

  10 Cartway N, Eastham, MA 2642

  Tucked away on 20.3 acres with sweeping views of Cape Cod Bay, this extraordinary property offers a rare blend of history, nature, and privacy. Originally built in 1780 and relocated from Bridge Road, this antique home—once a rustic hunting and fishing camp—has been in the same family for generations. Known as the ''House that Lives in Nature,'' it sits harmoniously within its surroundings, with

  Eva Scott Gibson Sotheby's International Realty

  10 Cartway N, Eastham, MA 2642
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  /51

  $827,000

  • 2 Beds
  • 1.5 Baths
  • 2,192 Sq Ft

  55 Grandfathers Way, Eastham, MA 02642

  This classic post-and-beam colonial brings warmth and personality from the moment you arrive. Rich wood tones, exposed beams, and wide-board floors set the tone throughout, creating a home that feels both timeless and welcoming.A charming wraparound porch draws you in to the bright sunroom that brings in natural light and offers a cozy spot for morning coffee or quiet afternoons. For those chili

  Jen Whitaker Gibson Sotheby's International Realty

  55 Grandfathers Way, Eastham, MA 02642
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  /28

  $695,000

  • 3 Beds
  • 2 Baths
  • 1,192 Sq Ft

  55 Leona Terrace, Brewster, MA 02631

  This house checks all the boxes. Enjoy one floor living with first floor laundry and A/C. Low maintenance property, one car garage, at the end of a dead end street, and only .3 miles from the Cape Cod Rail Trail.Lovingly cared for by its original owner since it was built in 1996, this lightly used ranch reflects decades of pride, quality, and meticulous maintenance, offering buyers a rare

  Anthony Dimauro Fathom Realty MA

  55 Leona Terrace, Brewster, MA 02631
• 

  

  /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
• 

  

  /42

  $2,995,000

  • 16 Beds
  • 15.5 Baths
  • 7,922 Sq Ft

  1861 Main St, Brewster, MA 02631

  Welcome to the distinguished Old Manse Inn, a romantic and historic Sea Captain's manor in the heart of Brewster, Cape Cod. A proud member of the Select Registry, this premier Bed and Breakfast blends timeless charm with modern comforts. The property offers 12 uniquely decorated guest rooms with en-suite baths, three elegant common areas, a dedicated dining room, and a fully equipped commercial

  Eva Scott Gibson Sotheby's International Realty

  1861 Main St, Brewster, MA 02631
• 

  

  /31

  $595,000

  • 2 Beds
  • 2 Baths
  • 1,623 Sq Ft

  18 West Rd Unit 307, Orleans, MA 02653

  Enjoy carefree living close to all Orleans has to offer in this elegant, 62+ independent living community. This 3rd Floor corner end unit features a bright open and spacious floor plan with 2 bedrooms and 2 full baths, full size kitchen, dining room with extra windows, living room with large outdoor balcony. Primary bedroom has 2 closets & a private bath with walk-in shower. Guest bedroom or

  Dee Higgins Gibson Sotheby's International Realty

  18 West Rd Unit 307, Orleans, MA 02653
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  /25

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,277 Sq Ft

  26 Pinewood Dr, Brewster, MA 02631

  This is the lowest-priced home in the beautiful town of Brewster. Located in a quiet residential neighborhood, it has been a rental property for many years and shows significant wear and tear. It needs imagination and some updating. The kitchen and 2 of the bedrooms are large. This is an ideal situation for a buyer with vision to enter the housing market and build substantial equity. The solar

  Karen Lilly Property Cape Cod

  26 Pinewood Dr, Brewster, MA 02631
• 

  

  /44

  $629,000

  • 4 Beds
  • 2 Baths
  • 1,828 Sq Ft

  16 Partridge Ln, Harwich, MA 02645

  Opportunity knocks! This 4-bedroom, 2-bath Cape-style home is brimming with potential and is ready for your personal touch. Nestled on a quiet street in popular East Harwich, this home provides convenient access to Route 6, Harwich shopping, and nearby beaches and lakes.Step inside and you'll find a traditional layout with hardwood floors, a spacious living room, and an eat-in kitchen with new

  Brennan Finnegan William Raveis Real Estate & Home Services

  16 Partridge Ln, Harwich, MA 02645
• 

  

  /38

  $2,499,000

  • 3 Beds
  • 4 Baths
  • 3,090 Sq Ft

  2 Seapine Rd, North Chatham, MA 02650

  Offered fully furnished, this light-filled contemporary Cape in North Chatham blends coastal elegance with casual sophistication. The main level features a welcoming den, an inviting living room with a fireplace, and a stylish kitchen and dining area that open to a sunny deck, ideal for seamless indoor-outdoor living. The serene first floor primary suite offers comfort and privacy. Upstairs, two

  Jack Bohman Gibson Sotheby's International Realty

  2 Seapine Rd, North Chatham, MA 02650
• 

  

  /31

  $799,000

  • 3 Beds
  • 1.5 Baths
  • 1,403 Sq Ft

  20 Namskaket Rd, Orleans, MA 02653

  Great price improvement $975,000.00 to $ 875,000.00. Conveniently located close to downtown Orleans, this is a 3 bedroom, 1 1/2 bath colonial style house. Situated on 3/4 acre in a peaceful setting with gardens, plenty of privacy and space to add to outdoor living or more substantial living space. Above the garage is an open space in which to create, exercise or dabble with projects. The basement

  Mary Lyttle Beach Road Properties

  20 Namskaket Rd, Orleans, MA 02653
• 

  

  /24

  $115,000

  • 1 Bed
  • 1 Bath
  • 306 Sq Ft

  13 S Orleans Rd Unit 28, Orleans, MA 02653

  Exceptional waterfront investment in Orleans! This 1-bedroom, 1-bath condominium at The Cove provides sweeping Town Cove views and the ease of fully managed, hotel-style ownership. Designed for cash investors, the unit is not suited for year-round living but offers owners up to two discounted weeks annually, with rental income generated the remainder of the year. The Cove is professionally

  Barbara Francke Kinlin Grover Compass

  13 S Orleans Rd Unit 28, Orleans, MA 02653
• 

  

  /39

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,128 Sq Ft

  42 Old Colony Way Unit 5, Orleans, MA 02653

  Corner unit! Great location with close proximity to the beach, bike path, and downtown Orleans. This first floor 2 bedroom 2 bath condo is located on the back side of the building. It has direct access to your parking space and is only steps away from your private patio. This nicely cared for unit features newer windows and sliding glass door as well as newer carpeting and hot water heater. This

  Kevin Austin William Raveis Real Estate & Home Services

  42 Old Colony Way Unit 5, Orleans, MA 02653

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