29

Orleans, MA 2-Story Homes for Sale

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  • 188 Rock Harbor Rd, Orleans, MA 02653
    188 Rock Harbor Rd, Orleans, MA 02653
    188 Rock Harbor Rd, Orleans, MA 02653
    /75

    $1,745,000

    • 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

    Agent Photo

    Barbara Garside

    eXp Realty, LLC

    (508) 719-6484

    188 Rock Harbor Rd, Orleans, MA 02653
  • 6 Snow Way, Orleans, MA 02653
    6 Snow Way, Orleans, MA 02653
    6 Snow Way, Orleans, MA 02653
    /42

    $3,860,000

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

    6 Snow Way, Orleans, MA 02653

    Welcome to 6 Snow Way, a stunning private waterfront estate in East Orleans, where sophisticated coastal living harmonizes with the serene beauty of Rachel's Cove. This exquisite home, perched majestically on a hill, offers breathtaking water views, extensive waterfront, is strategically positioned outside the flood zone, and features a gently rolling landscape that gracefully descends to the

    Diana Lucivero Compass Massachusetts, LLC

    6 Snow Way, Orleans, MA 02653
  • 4 Asas Landing, Orleans, MA 02653
    4 Asas Landing, Orleans, MA 02653
    4 Asas Landing, Orleans, MA 02653
    /61

    $2,600,000

    • 3 Beds
    • 3 Baths
    • 2,756 Sq Ft

    4 Asas Landing, Orleans, MA 02653

    Elevated above the serene waters of Town Cove and adjacent to Asa's Landing, this Orleans property offers timeless appeal in one of the Cape's most coveted waterfront neighborhoods. The gracious 3-bedroom home is thoughtfully sited to capture unobstructed water views from every room, providing a backdrop of natural beauty throughout the seasons. A boat house, and two-car garage add both charm and

    Dawn Lee Gibson Sotheby's International Realty

    4 Asas Landing, Orleans, MA 02653
  • 136 Monument Rd, Orleans, MA 02653
    136 Monument Rd, Orleans, MA 02653
    136 Monument Rd, Orleans, MA 02653
    /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
  • 645 S Orleans Rd, Orleans, MA 02653
    645 S Orleans Rd, Orleans, MA 02653
    645 S Orleans Rd, Orleans, MA 02653
    /57

    $3,950,000

    • 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
  • 12 Windswept Ln, Orleans, MA 2653
    12 Windswept Ln, Orleans, MA 2653
    12 Windswept Ln, Orleans, MA 2653
    /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
  • 4 Asas Landing, Orleans, MA 02653
    4 Asas Landing, Orleans, MA 02653
    4 Asas Landing, Orleans, MA 02653
    /63

    $3,450,000

    • 3 Beds
    • 3 Baths
    • 2,756 Sq Ft

    4 Asas Landing, Orleans, MA 02653

    Elevated above the serene waters of Town Cove and adjacent to Asa's Landing, this Orleans property presents the opportunity to create a legacy estate in one of the Cape's most coveted neighborhoods with a home and additional land on Gibson Rd. The gracious 3-bedroom home is thoughtfully sited to offer unobstructed water views from every room, providing a backdrop of unparalleled natural beauty.

    Dawn Lee Gibson Sotheby's International Realty

    4 Asas Landing, Orleans, MA 02653
  • 46 Freeman Ln, Orleans, MA 02653
    46 Freeman Ln, Orleans, MA 02653
    46 Freeman Ln, Orleans, MA 02653
    /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
  • 4 Monomoy Ln, Orleans, MA 02653
    4 Monomoy Ln, Orleans, MA 02653
    4 Monomoy Ln, Orleans, MA 02653
    /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
  • 2 Monomoy Ln, Orleans, MA 02653
    2 Monomoy Ln, Orleans, MA 02653
    2 Monomoy Ln, Orleans, MA 02653
    /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
  • 10 Center Place Unit 16, Orleans, MA 02653
    10 Center Place Unit 16, Orleans, MA 02653
    10 Center Place Unit 16, Orleans, MA 02653
    /61

    $924,900

    • 2 Beds
    • 2 Baths
    • 1,567 Sq Ft

    10 Center Place Unit 16, Orleans, MA 02653

    Orleans Village Perfection - Renovated Townhome with Custom Finishes. Rare luxury townhome in the heart of Orleans! World-class beaches, boutique shopping, fine dining & everything Orleans has to offer. This move-in-ready residence offers a maintenance-free lifestyle with brand new ducted central heat/AC, two fully renovated baths, custom closets, updated lighting and flooring, plus a private

    Michael Letourneau Orleans Village Properties, LLC

    10 Center Place Unit 16, Orleans, MA 02653
  • 15 Heritage Dr, Orleans, MA 02653
    15 Heritage Dr, Orleans, MA 02653
    15 Heritage Dr, Orleans, MA 02653
    /36

    $995,000

    • 4 Beds
    • 2.5 Baths
    • 1,976 Sq Ft

    15 Heritage Dr, Orleans, MA 02653

    This lovely property has timeless appeal with a classic colonial design and is ideal for year round living or a summer retreat. Nestled on a quiet treelined street in a desirable neighborhood in South Orleans you will fall in love with all its natural charm. Step inside and you are greeted by a sense of warmth into the sunlit foyer of this 4 bedroom 2 and a half bath home which sits gracefully

    Karen Maresca Today Real Estate

    15 Heritage Dr, Orleans, MA 02653
  • 24 Sparrowhawk Rd, Orleans, MA 02653
    24 Sparrowhawk Rd, Orleans, MA 02653
    24 Sparrowhawk Rd, Orleans, MA 02653
    /40

    $1,595,000

    • 3 Beds
    • 2 Baths
    • 1,509 Sq Ft

    24 Sparrowhawk Rd, Orleans, MA 02653

    Your day begins listening to the ocean calling as you take in the invigorating salt air and head off for an early morning walk over your nearby association footbridge to a gorgeous, almost deserted stretch of Nauset Beach. Afterwards, you gather outdoors for an alfresco lunch on your sundrenched backyard patio, surrounded by an expansive lawn, stunning flowering perennials and a privacy border of

    Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

    24 Sparrowhawk Rd, Orleans, MA 02653
  • 142 Monument Rd, Orleans, MA 02653
    142 Monument Rd, Orleans, MA 02653
    142 Monument Rd, Orleans, MA 02653
    /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
  • 31 Monument Rd, Orleans, MA 2653
    31 Monument Rd, Orleans, MA 2653
    31 Monument Rd, Orleans, MA 2653
    /19

    $845,000

    • 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
  • 2 Little Cove Ln, Orleans, MA 02653
    2 Little Cove Ln, Orleans, MA 02653
    2 Little Cove Ln, Orleans, MA 02653
    /67

    $1,995,000

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

    2 Little Cove Ln, Orleans, MA 02653

    Price adjustment! This beautifully remodeled home offers a perfect blend of luxury, comfort, and style, all set within a private backyard oasis. Step outside to enjoy a brand new 36x18 heated pool ideal for both relaxing and entertaining. With its thoughtfully designed & distinctive floor plan, this elegant property provides versatile spaces for hosting family and friends while also offering

    Susan Sullivan Realty Consultants of Cape Cod

    2 Little Cove Ln, Orleans, MA 02653
  • 21 S Orleans Rd, Orleans, MA 02653
    21 S Orleans Rd, Orleans, MA 02653
    21 S Orleans Rd, Orleans, MA 02653
    /51

    $2,199,999

    • 5 Beds
    • 5 Baths
    • 4,416 Sq Ft

    21 S Orleans Rd, Orleans, MA 02653

    Ideally located in the vibrant commercial district of Orleans and overlooking scenic Town Cove, this 4,400+ square foot mixed-use building presents a rare opportunity for investors, developers, or business owners seeking a high-visibility location with tremendous potential. Built in 1840, this property features over 1,500 SF of street-level retail space, two residential apartments, and generous

    Andrew Grattan Christie's International Real Estate Atlantic Brokerage

    21 S Orleans Rd, Orleans, MA 02653
  • 24 Old Tote Rd, Orleans, MA 02653
    24 Old Tote Rd, Orleans, MA 02653
    24 Old Tote Rd, Orleans, MA 02653
    /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
  • 63 Old Field Rd, Orleans, MA 02653
    63 Old Field Rd, Orleans, MA 02653
    63 Old Field Rd, Orleans, MA 02653
    /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
  • 40 Toms Hollow Ln, Orleans, MA 02662
    40 Toms Hollow Ln, Orleans, MA 02662
    40 Toms Hollow Ln, Orleans, MA 02662
    /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
  • 30 Deer Run, Orleans, MA 02653
    30 Deer Run, Orleans, MA 02653
    30 Deer Run, Orleans, MA 02653
    /35

    $5,750,000

    • 5 Beds
    • 6.5 Baths
    • 6,021 Sq Ft

    30 Deer Run, Orleans, MA 02653

    Stunning Salt Waterfront Estate on the Mill Pond with panoramic views to Roberts Cove & Nauset Harbor to the Light House & beyond!Superior quality throughout this 5 bedroom 5 1/2 bath home. Great privacy & beautiful easy to care for landscaping. Wonderful open sunny rooms & great flow. Large gourmet kitchen & formal dining room. Beautiful Great Room with a fireplace wall, sliders & a French door

    Nikki Carter William Raveis Real Estate & Home Services

    30 Deer Run, Orleans, MA 02653
  • 17 Pendleton Dr, Orleans, MA 2653
    17 Pendleton Dr, Orleans, MA 2653
    17 Pendleton Dr, Orleans, MA 2653
    /41

    $1,590,000

    • 3 Beds
    • 2.5 Baths
    • 1,925 Sq Ft

    17 Pendleton Dr, Orleans, MA 2653

    This masterfully reimagined home blends classic charm with artisan craftsmanship. Thoughtfully transformed by its owners and local master craftsmen, this ''cottage by the sea'' is a rare find, offering custom details at every turn. The living room features reclaimed 125-year-old wood from a local Masonic Temple, a wood-burning fireplace with a raised hearth, a custom bay window with built-in

    Brett Holmes Compass

    17 Pendleton Dr, Orleans, MA 2653
  • 216 Main St, Orleans, MA 2653
    216 Main St, Orleans, MA 2653
    216 Main St, Orleans, MA 2653
    /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
  • 6 Monomoy Ln, Orleans, MA 02653
    6 Monomoy Ln, Orleans, MA 02653
    6 Monomoy Ln, Orleans, MA 02653
    /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
  • 8 Monomoy Ln, Orleans, MA 02653
    8 Monomoy Ln, Orleans, MA 02653
    8 Monomoy Ln, Orleans, MA 02653
    /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
  • 5 Reilly Run, Orleans, MA 02653
    5 Reilly Run, Orleans, MA 02653
    5 Reilly Run, Orleans, MA 02653
    /29

    $1,249,000 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

    Sarah Dacey Champion Realty Group, LLC

    5 Reilly Run, Orleans, MA 02653
  • 47 Daley Terrace, Orleans, MA 2653
    47 Daley Terrace, Orleans, MA 2653
    47 Daley Terrace, Orleans, MA 2653
    /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
  • 10 Landers Ln, Orleans, MA 2653
    10 Landers Ln, Orleans, MA 2653
    10 Landers Ln, Orleans, MA 2653
    /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
  • 33 Rogers Rd, Brewster, MA 02631
    33 Rogers Rd, Brewster, MA 02631
    33 Rogers Rd, Brewster, MA 02631
    /51

    $899,000

    • 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
Massachusetts Barnstable County Orleans

2-Story Homes for Sale in Orleans, MA

Home Trends in Orleans, MA

On average, homes in Orleans, MA sell after 70 days on the market compared to the national average of 70 days. The median sale price for homes in Orleans, MA over the last 12 months is $1,225,000, down 43% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,225,000
Median Single Family Sale Price
$940,000
Median 2 Bedroom Sale Price
$420,000
Median 1 Bedroom Sale Price
$255,000
Average Price Per Sq Ft
$592
Number of Homes for Sale
8
Last 12 months Home Sales
42
Months of Supply
2.30
Median List Price
$1,795,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-43%
How to Buy a Home How to Finance a Home How to Sell a Home

In Orleans, there are currently 29 two-story homes for sale, offering abundant choices for those who prioritize both convenience and functionality in their living space. Whether you're in the market for a traditional two-story house or considering the versatility of a two-story townhome, these properties provide a wealth of options to explore. Ranging from compact yet cozy condos to expansive family residences, the two-story homes for sale in Orleans, MA come in various sizes and floorplans, ensuring there's something to accommodate every lifestyle and preference.

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