East Orleans, MA Homes for Sale

/27
$649,000

$50K PRICE DROP
- 3 Beds
- 1 Bath
- 960 Sq Ft
20 Stone Ct, Eastham, MA 02642

NEW PRICE! Bayside Eastham living... Tucked away on a quiet Eastham cul-de-sac, this well-maintained home offers a blend of Cape Cod charm, modern updates, and an exceptional location near Fort Hill, Town Cove, and the Cape Cod Rail Trail and only two miles to the Eastham/Orleans rotary.Just minutes from the Town Cove landing, Fort Hill in the Cape Cod National Seashore, stunning bay beaches, and

Marirose Lynch RE/MAX Real Estate Center

20 Stone Ct, Eastham, MA 02642
/62
$1,049,000
- 3 Beds
- 2 Baths
- 1,478 Sq Ft
507 S Orleans Rd, Orleans, MA 02653

This beautiful Cape-style home provides a perfect balance of modern luxury and tranquil Cape Cod living. Situated on nearly an acre of land, the property boasts views of Lily's Pond with direct water access right from your own expansive backyard.Completely gutted to the studs in 2024 and meticulously renovated, the home blends high-end, designer finishes with everyday coastal conveniences, making

Cape Cod Power of Two Compass

507 S Orleans Rd, Orleans, MA 02653
/74
$4,500,000

Open Wed 4PM - 6PM
- 4 Beds
- 5 Baths
- 3,556 Sq Ft
22 Blake Ln, Orleans, MA 02653

Set on a rare peninsula overlooking 27 acres of protected conservation land at Kent's Point, 22 Blake Lane offers over an acre of manicured grounds, sweeping 270-degree water views, breathtaking sunsets, and deepwater access to Little Pleasant Bay -- idyllic waters for boating, nature, and endless coastal recreation. A long private driveway delivers you into a world apart. The contemporary home

Guthrie Schofield Group Berkshire Hathaway HomeServices Robert Paul Properties

22 Blake Ln, Orleans, MA 02653
/27
$275,000
- 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 Christie's International Real Estate Atlantic Brokerage

1061 State Hwy Unit 4, Eastham, MA 02642
/36
$499,000

$101K PRICE DROP
- 2 Beds
- 1.5 Baths
- 1,344 Sq Ft
21 Locust Rd, Eastham, MA 02642

This beautifully kept, spacious, 2 bedroom, year round condominium offers immaculate, thoughtful and comfortable living in a central location with easy access to the bike trail, National Seashore, shopping and bay and ocean beaches combined with sweeping views over Salt Pond. One half of a large, antique style, duplex rebuilt in 2005, this newly listed unit offers carefree and pristine year round

The Pechukas Group Kinlin Grover Compass

21 Locust Rd, Eastham, MA 02642
/42
$2,700,000

$1M PRICE DROP
- 7 Beds
- 6.5 Baths
- 3,549 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 estate. With a deep-water dock, moorings, and direct bay access, it delivers a front-row seat to the rhythms of Pleasant Bay and boundless recreation. Both homes enjoy 270-degree views across the water to

Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

645 S Orleans Rd, Orleans, MA 02653
/71
$2,895,000
- 4 Beds
- 3.5 Baths
- 3,164 Sq Ft
28 Mallard Dr, Orleans, MA 02653

Exceptional marshfront home offering expansive views of Cape Cod Bay in Orleans. Set on 1.12 private acres, this spacious 4-bedroom, 3.5-bath home captures the beauty of the Cape with sweeping marsh vistas and ever-changing coastal light. The thoughtfully designed layout provides generous living spaces ideal for relaxing or entertaining, with large windows that frame the natural surroundings. The

Sandra Milano RE/MAX Executive Realty

28 Mallard Dr, Orleans, MA 02653
/47
$699,000

$60K PRICE DROP
- 2 Beds
- 1.5 Baths
- 825 Sq Ft
5 Weir Rd, Eastham, MA 02642

Charming 2-bedroom ranch on a spacious 0.41-acre lot in desirable Eastham, just minutes from Thumpertown Beach. This bright, sunny home offers easy one-level living, ideal for year-round use or a Cape Cod retreat. The standout three-season sunroom features three new skylights, filling the space with natural light--perfect for relaxing or entertaining. A cozy living room with gas fireplace adds

Team Brown Thomas D Brown R E Associates

5 Weir Rd, Eastham, MA 02642
/27
$1,900,000
- 6 Beds
- 6.5 Baths
- 3,843 Sq Ft
88 Massachusetts 6a, Orleans, MA 02653

Selling as one unit: 3 parcels of improved land in the center of Orleans, Village Center District. The property consists of #88: a 2-bedroom one bath 1,400 square foot single family home with a detached two car garage with unfinished space above, and a 520 square foot foundation with no building added. #86A: a 1,494 square foot building with 3 one-bedroom rental units, and #86B: a 949 square foot

Sharon Kingman Dixon William Raveis Real Estate & Homes Services

88 Massachusetts 6a, Orleans, MA 02653
/19
$1,100,000
- Land
- 1.56 Acres
- $705,128 per Acre
0 Partridge, Brewster, MA 02631

Build your beautiful custom Cape home on this large 1.56 acre lot and walk to three Brewster bay beaches and the Town pool! This is the only large lot available north of 6A with the ability to build a 4-7+ bedroom home with a large footprint. Town Planning Dept. has signed of on an ANR (Approval Not Required) .The lot abuts the Spruce Hill Conservation land to the rear to provide the utmost in

Christine Altneu Berkshire Hathaway HomeServices Robert Paul Properties

0 Partridge, Brewster, MA 02631
/42
$1,750,000
- 3 Beds
- 2 Baths
- 3,280 Sq Ft
40 Kittiwake Ln, Eastham, MA 02642

Stunning 3BR/2BA Post & Beam contemporary with 176' of waterfront on beautiful Town Cove. This quality-built home offers breathtaking open water views, vaulted ceilings, custom built-ins, and an estate-like setting with exceptional privacy. The gourmet kitchen features a center island, double ovens, and abundant workspace. Enjoy spacious living with two fireplaces, a large gathering room, and a

Mike Karras William Raveis R.E. & Home Services

40 Kittiwake Ln, Eastham, MA 02642
/79
$1,250,000
- 4 Beds
- 3.5 Baths
- 2,868 Sq Ft
35 Sands Rd, Eastham, MA 02642

Welcome to 35 Sands Road, a beautifully expanded and updated Cape-style home set on just under an acre along a private way near First Encounter Beach and Herring Pond. This spacious 4-bedroom, 3.5-bath residence blends classic Cape Cod charm with modern amenities and thoughtful design. A substantial 2004 addition introduced a luxurious primary suite and enhanced the home's open, comfortable

Rob Young William Raveis Real Estate & Home Services

35 Sands Rd, Eastham, MA 02642
/30
$280,000

$27K PRICE DROP
- 1 Bed
- 1 Bath
- 294 Sq Ft
785 State Hwy Unit 9, Eastham, MA 02642

Welcome to your Cape Cod retreat. This charming SEASONAL cottage, nestled within the serene Cranberry Cottages complex, offers a blend of comfort and convenience. With 294 sq ft. of living space, this studio cottage is perfect for those seeking a cozy getaway exemplifying that the best things often come in small packages. No detail has been overlooked from the custom plantation shutters to the

Callie Zaglio Kinlin Grover Compass

785 State Hwy Unit 9, Eastham, MA 02642
/30
$325,000
- 1 Bed
- 1 Bath
- 579 Sq Ft
81 Fletcher Ln Unit I, Brewster, MA 02631

Enjoy this corner unit with one-level living in this beautifully renovated first-floor condo at sought-after Ocean Edge Resort. No stairs to navigate to get to this unit. This light-filled 1-bedroom, 1-bath home offers an open-concept design with a seamless, modern feel. The updated kitchen features quartz countertops, stainless steel appliances, stylish cabinetry, and contemporary lighting. A

Leighton Team Keller Williams Realty

81 Fletcher Ln Unit I, Brewster, MA 02631
/40
$1,690,000

$60K PRICE DROP
- 3 Beds
- 3 Baths
- 2,471 Sq Ft
410 Blueberry Pond Dr, Brewster, MA 02631

Completed in 2023, this newly built, fully electric home blends elevated design, sustainability, and timeless Cape Cod charm. Privately sited on 1.15 acres across two parcels and surrounded by conservation, the property offers gated access to Blueberry Pond and 2,400 sq ft of living across three levels. Designed with a primary suite on each main level, the layout supports multigenerational living

Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

410 Blueberry Pond Dr, Brewster, MA 02631
/35
$355,000

Open Fri 2:30PM - 4PM
- 1 Bed
- 1 Bath
- 579 Sq Ft
102 Fletcher Ln Unit H, Brewster, MA 02631

Beautifully updated and move-in ready, this top-floor 1-bed, 1-bath condo in the desirable Ocean Edge Resort community offers the perfect blend of style and comfort. Soaring cathedral ceilings and an open layout create a bright, airy atmosphere, while the private balcony provides sweeping views of the Nicklaus Design Golf Course. Recent renovations include a brand-new kitchen with modern

Leighton Team Keller Williams Realty

102 Fletcher Ln Unit H, Brewster, MA 02631
/41
$799,900

$99K PRICE DROP
- 3 Beds
- 2 Baths
- 1,683 Sq Ft
80 Runway Ln, Eastham, MA 02642

Welcome to 80 Runway Lane in beautiful Eastham on Cape Cod - Recent updates include new windows, siding, trim, a fully remodeled kitchen and bathrooms, luxury vinyl plank flooring, refinished hardwoods, and restained interior doors and trim. Also the roof is just 3 years old.Ideally located near restaurants and the beaches of Cape Cod Bay, this home offers the perfect blend of convenience and

LINDA COLLINS Christie's International Real Estate Atlantic Brokerage

80 Runway Ln, Eastham, MA 02642
/37
$850,000

$145K PRICE DROP
- 4 Beds
- 2 Baths
- 1,343 Sq Ft
10 Alston Ct, Eastham, MA 02642

Waterfront House & Cottage on scenic Minister's Pond offering rare investment potential and lifestyle flexibility. This unique compound features a main home plus separate cottage--ideal for personal use, rental income, or multigenerational living.The detached cottage features a spacious studio layout with full bath, creating excellent guest accommodations or additional income potential. Combined,

Rob Young William Raveis Real Estate & Home Services

10 Alston Ct, Eastham, MA 02642
/2
$949,000

Coming Soon
- 3 Beds
- 3 Baths
- 1,165 Sq Ft
189 Main St Unit 189, Orleans, MA 02653

Amazing opportunity to own this classic Cape Cod 2005 cape style home in desirable Orleans Village. Beautiful Main street is excitingly busy in the summer season and peaceful in the off season. Nauset beach just a few miles away makes this the perfect beach village atmosphere. Biking, swimming and kayaking are easily available in this location. The home pours in natural lighting from every angel

Sheri Valeri Jack Conway & Co Inc

189 Main St Unit 189, Orleans, MA 02653
/22
$600,000
- Land
- 1.24 Acres
- $483,871 per Acre
17 Skymeadow Dr, Orleans, MA 02653

Located on a beautiful cul-de-sac surrounded by quintessential Cape Cod homes, this rare panhandle lot sits waiting for your Cape Cod dream home. Lot is offered with engineering, bulding plans and permits in place. Skymeadow Drive is a wonderful, lovingly maintained neighborhood just minutes away from Skaket Beach and Cape Cod Bay. Walking, biking, close to Orleans village center-this area

Robin Thayer Gibson Sotheby's International Realty

17 Skymeadow Dr, Orleans, MA 02653
/34
$475,000

$100K PRICE DROP
- 2 Beds
- 1.5 Baths
- 1,543 Sq Ft
82 Old Orchard Rd, Eastham, MA 02642

MOTIVATED SELLERS! Get your piece of Cape Cod in Eastham on time for the summer! 82 Old Orchard Road in is a charming and well-maintained townhouse (duplex). This affordable home is offering the perfect blend of privacy, comfort, and classic Lower Cape living. This inviting two-bedroom, one-and-a-half-bath townhouse features an additional room ideal for a home office/study, along with 247 sq.ft.

Mihaela Miteva Today Real Estate

82 Old Orchard Rd, Eastham, MA 02642
/32
$1,350,000
- 5 Beds
- 3.5 Baths
- 4,416 Sq Ft
21 S Orleans Rd, Orleans, MA 02653

This stately Orleans landmark offers an ideal in-town location with high visibility and multi-use - apartments and retail space. This sale is for land and building only; not a business (but seller is open to offers for inventory buy-out). The prime retail space overlooks busy Route 28 at the front for fabulous exposure and pretty Town Cove at the rear. The retail space is entered at street level

Tracey Oringer Kinlin Grover Compass

21 S Orleans Rd, Orleans, MA 02653
/42
$4,999,000
- 4 Beds
- 3 Baths
- 3,867 Sq Ft
66 Tides End Ln, Orleans, MA 02653

Own a coveted East Orleans property with a private deep-water dock on a sprawling 2.62 acres, just 2.6 miles from Nauset Beach. This estate, surrounded by water, features rolling meadows and mature trees. The 3,867 sq ft residence blends timeless charm with modern comforts. Located on Lucy's Point Peninsula, it's perfect for a family compound or riverfront retreat. Inside, enjoy wide plank pine

Cape Cod Power of Two Compass

66 Tides End Ln, Orleans, MA 02653
/21
$749,000
- 3 Beds
- 2 Baths
- 1,040 Sq Ft
17 Kings Way, Orleans, MA 02653

On a quiet dead end street close to downtown Orleans, sits this updated ranch style home on a large landscaped lot. There's even a back patio with electrical outlet ready for your outdoor kitchen! Stainless appliances, double pain windows and slider to the deck make this a low maintenance gem. Finished basement with an additional 600 sq. ft. of living space and full bath.New deck is being

Ken Hager Classic Cape Real Estate, LLC

17 Kings Way, Orleans, MA 02653
/34
$1,799,000

New Construction
- 3 Beds
- 4 Baths
- 3,750 Sq Ft
163 Samoset Rd, Eastham, MA 02642

NEW CONSTRUCTION: This extraordinary masterpiece nestled in the heart of Eastham. This stunning 3,750 sq ft residence offers an unparalleled blend of refined luxury, coastal elegance, and an effortless indoor-outdoor lifestyle that defines the very best of Cape living. This is a rare opportunity to own a flawlessly crafted home in one of the Outer Cape's most sought-after locations.No detail has

Lisa Loveland Keller Williams Realty Boston-Metro

163 Samoset Rd, Eastham, MA 02642
/27
$275,000
- 1 Bed
- 1 Bath
- 252 Sq Ft
1061 State Hwy Unit 1061, 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 Christie's International Real Estate Atlantic Brokerage

1061 State Hwy Unit 1061, Eastham, MA 02642
/54
$999,999
- 3 Beds
- 2 Baths
- 1,908 Sq Ft
15 Runway Ln, Eastham, MA 02642

This meticulously maintained home is in the heart of Eastham has everything you need for your dream Cape Cod home. Located in a quiet neighborhood less than a mile from Cape Cod Bay beaches it features a beautifully mature landscaped private level yard with an underground sprinkler system, a large outdoor private shower, a deck with a retractable awning, and a custom-built shed. This light filled

Sarah Sherman Hopper R E/Outer Cape Rentals

15 Runway Ln, Eastham, MA 02642
/2
$699,000
- 4 Beds
- 2 Baths
- 1,408 Sq Ft
5 Anderson Ln, Eastham, MA 02642

Tucked away down a quiet dirt road in the heart of Eastham, 5 Anderson Lane offers a rare combination of privacy, tranquility, and classic Cape Cod charm. This lovely 4-bedroom, 2-bath home is set in a peaceful, secluded setting while still being just minutes from Wiley Park, Campground Beach, and Nauset Light Beach. Surrounded by the natural beauty of the Outer Cape, the property enjoys close

Liz Holguin Classic Cape Real Estate, LLC

5 Anderson Ln, Eastham, MA 02642
/57
$2,150,000

$150K PRICE DROP
- 5 Beds
- 5 Baths
- 4,091 Sq Ft
22 Winslow Dr, Orleans, MA 02653

Overlooking a tranquil pond, 22 Winslow Drive offers a peaceful setting with a strong sense of privacy. Birds move easily through the surrounding landscape, and the quiet setting creates a calm and natural atmosphere. This gracious Cape Cod home has been cherished by four generations. Thoughtfully expanded over the years while preserving its warmth and character. Inside, more than 4,000 square

Jen Whitaker Gibson Sotheby's International Realty

22 Winslow Dr, Orleans, MA 02653
/37
$1,749,900

$50K PRICE DROP
- 5 Beds
- 4.5 Baths
- 2,951 Sq Ft
60 Rock Harbor Rd, Orleans, MA 02653

A turnkey investment opportunity in one of Cape Cod’s most sought-after vacation markets. This exceptional Orleans property blends historic charm, strong rental income, and lifestyle appeal. Located just .5 miles from Rock Harbor Beach, it offers easy access to boating, waterfront dining, and popular Cape attractions. Built in 1867 and moved to its current location with a full concrete foundation

Deborah Salvatore Berkshire Hathaway Home Service New England Properties

60 Rock Harbor Rd, Orleans, MA 02653
/83
$2,500,000
- 4 Beds
- 3 Baths
- 2,544 Sq Ft
27 S Orleans Rd, Orleans, MA 02653

Tucked away in one of the area's most coveted in-town waterfront settings, this exceptional property offers the perfect blend of privacy, convenience, and coastal living. Thoughtfully maintained and beautifully positioned to capture stunning water views of Town Cove from nearly every room, the home features four bedrooms, three full baths, and a highly desirable floor plan designed for both

Daneen Law Gibson Sotheby's International Realty

27 S Orleans Rd, Orleans, MA 02653
/35
$899,900

$25K PRICE DROP
- 3 Beds
- 2 Baths
- 1,633 Sq Ft
1066 Millstone Rd, Brewster, MA 02631

This cape style ranch has been fully renovated from top to bottom and is only minutes from Brewsters best beaches. From the custom kitchen with an oversized quartz island and stainless steel appliances to the spacious sun drenched bonus room, this home is the one that you've been waiting for. Featuring new white oak floors, meticulously tiled bathrooms, new windows, first floor laundry and a

Samantha Kane Keller Williams Realty Signature Properties

1066 Millstone Rd, Brewster, MA 02631
/41
$1,300,000
- 4 Beds
- 2 Baths
- 2,316 Sq Ft
385 Bridge Rd, Eastham, MA 02642

Introducing 385 Bridge Road, an Eastham gem with endless possibilities for expansion, improvement, or for a new home on the included 1.4 acre lot. Maybe even a family compound. Ideally located just a short walk from Cape Cod Bay, and minutes to the National Seashore, Fort Hill and other Cape Cod landmarks, this inviting residence presents a rare opportunity to own a piece of history in move-in

Stephen Laska RE/MAX Vision

385 Bridge Rd, Eastham, MA 02642
/17
$325,000
- 1 Bed
- 1 Bath
- 579 Sq Ft
81 Fletcher Ln Unit I, Brewster, MA 02631

Sought after Corner Unit with one-level living in this beautifully renovated first-floor condo at sought-after Ocean Edge Resort. No stairs to navigate to get to this unit. This light-filled 1-bedroom, 1-bath home offers an open-concept design with a seamless, modern feel. The updated kitchen features quartz countertops, stainless steel appliances, stylish cabinetry, and contemporary lighting. A

Leighton Team Keller Williams Realty

81 Fletcher Ln Unit I, Brewster, MA 02631
/9
$459,000
- 3 Beds
- 2 Baths
- 1,665 Sq Ft
235 Old Chatham Rd, Brewster, MA 02631

Property is being sold as-is.Three-bedroom home with potential to expand to up to five bedrooms. The property includes an existing well and electrical service already in place.Important: Do not attempt to enter the structure. Access will be provided to buyers and licensed contractors by appointment only and must be accompanied. Entry onto the property is at your own risk.Buyers and buyer's agents

Isaac Sargent Christie's Int'l RE Atlantic Brokerage

235 Old Chatham Rd, Brewster, MA 02631
/36
$850,000
- 3 Beds
- 2.5 Baths
- 2,072 Sq Ft
18 Sturbridge Dr, Orleans, MA 02653

Priced below assessment in a lovely neighborhood for you to make your own. Only about 1 mile from Little Pleasant Bay at the end of Portaminicut Rd., this 3 bedroom, 2 1/2 bath Cape has a first floor primary with private bath, fireplaced family room, formal dining room, and living room completing the first floor along with a half bath and laundry. Up the stairs brings you to 2 more good sized

Richard Ormon McDevitt REALTORS®

18 Sturbridge Dr, Orleans, MA 02653
/55
$1,895,000
- 3 Beds
- 2 Baths
- 1,740 Sq Ft
65 Pilgrims Path, Eastham, MA 02642

Enjoy the best of the Outer Cape from this well-maintained home in one of Eastham's most sought-after bayside neighborhoods. Situated on a combined 0.78 acres, including an abutting 0.3-acre parcel, this property is just 0.3 miles to Cole Road Beach, 0.6 miles to First Encounter Beach, and minutes from Wiley Park, Great Pond, and Cottontail Acres conservation trails. The home features 3 bedrooms,

The Jorie Fleming Group Compass

65 Pilgrims Path, Eastham, MA 02642
/47
$2,249,000
- 4 Beds
- 4.5 Baths
- 2,817 Sq Ft
435 Herring Brook Rd, Eastham, MA 02642

Set on 1.53 acres to the backdrop of marshlands, First Encounter Beach and famous Eastham sunsets, 435 Herring Brook Rd offers an open concept with thoughtfully designed interior and exterior gathering spaces that transition seamlessly. Four ensuite bedrooms, dispersed over two levels amongst a deceptively large 2,817 sf, offer first floor living and quite retreats. Be it a five minute stroll to

Jon Clark Nauset Management

435 Herring Brook Rd, Eastham, MA 02642
/33
$295,000
- 1 Bed
- 1 Bath
- 579 Sq Ft
100 Fletcher Ln Unit G, Brewster, MA 02631

Welcome to The Fletcher Condos within Ocean Edge Resort Community, one of Cape Cod's most desirable resort style living. This updated and fully renovated lower level condo with a bright, open-concept layout and with a private patio that opens up to a grassy area overlooking the Ocean Edge Golf Course. The renovated kitchen features quartz countertops, stainless steel appliances, and contemporary

Leighton Team Keller Williams Realty

100 Fletcher Ln Unit G, Brewster, MA 02631
/21
$385,000

$14K PRICE DROP
- 1 Bed
- 1 Bath
- 868 Sq Ft
24 Old Colony Way Unit 19, Orleans, MA 02653

This beautiful condo light and bright. There have been extensive renovations including bathroom, freshly painted walls and ceilings plus new carpeting throughout. Its is located in desirable Orleans and is what you've been waiting for as a permanent home or sweet getaway. Walk to the famous Chocolate Sparrow, Framers Market, Land Ho, Friends Market and so many more shops all within walking

Noreen Kennedy Kennedy Real Estate

24 Old Colony Way Unit 19, Orleans, MA 02653

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