South Orleans MA Real Estate & Homes for Sale

Contemporary salt waterfront home with private DOCK on Areys Pond providing access to Pleasant Bay and the Atlantic. The home sits on 1.67 wooded acres abutting several acres of conservation land, and offers 4000+ square feet of living space with water views from the living/dining room, up-dated kitchen, breakfast nook, and all four bedrooms, as well as from both screened porches. The primary bedroom suite offers water views, slider to an outside deck, private bath, walk-in closet and two offices.There is also an attached in-law apartment with a separate entrance which includes a screened porch, water views, bedroom, private bathroom, small living room and a kitchenette.The lower level has natural light on three sides and walk-out access on the water side. It offers two bedrooms, both with water views, a shared bath, a family room and a sun-filled exercise room/greenhouse.The homeowners enjoy entertaining at the large picnic area beside the Pond.Truly a rare opportunity to own a secluded, salt waterfront property with a dock for under $3 million.

Unique opportunity in Nauset Village! Open concept 2 bed / 1 bath year-round living with cathedral ceilings, exposed wooden beams, full sized eat-in kitchen with dishwasher & stackable washer/dryer, gas heat & Mini Split offering both A/C & heat. Loft Storage with custom wooden ladder. The lovely outside space is partially fenced & tree lined with patio, firepit, deck & outdoor shower. Sweet ''Curlew'' is a classic, quintessential Cape Cod cottage - being sold as is & fully furnished, everything you need to relax & enjoy your Cape Cod summer or cozy winter. Beachy destinations at every turn! .4 miles to Arey's Pond, minutes to Pleasant Bay, Crystal Lake & Pilgrim Lake. 5 minute drive to Downtown Orleans, Cape Cod Rail Trail, & two of the most desirable beaches on Cape - Skaket & Nauset! 10 minute scenic drive to highly desirable Chatham Main Street. Association fee includes master insurance, cable, landscaping, septic maintenance. Priced below Town Assessed value, NOT a drive by!

Unique opportunity in Nauset Village! Open concept 2 bed / 1 bath year-round living features cathedral ceilings, exposed wooden beams, full sized eat-in kitchen with dishwasher & stackable washer/dryer, gas heat & Mini Split offering both A/C & heat. Loft Storage with custom wooden ladder. The lovely outside space is partially fenced & tree lined with patio, firepit, deck & outdoor shower. Sweet ''Curlew'' is a classic, quintessential Cape Cod cottage. It is being sold as is & fully furnished - everything you need to relax and enjoy your Cape Cod summer or cozy winter. Beachy destinations at every turn! .4 miles to Arey's Pond, minutes to Pleasant Bay, Crystal Lake & Pilgrim Lake. 5 minute drive to Downtown Orleans, Cape Cod Rail Trail, and two of the most desirable beaches on Cape - Skaket & Nauset! 10 minute scenic drive to highly desirable Chatham Main Street. Association fee includes master insurance, cable, landscaping, septic maintenance. Priced below Town Assessed value, This home is NOT a drive by - must be seen!

Custom built contemporary with stunning views of Areys Pond and Namequoit River. Open style living, vaulted ceilings, large windows and hardwood floors throughout. Unique architectural details and superb craftsmanship make this property both innovative yet classic. The 4,222 square feet of living space allows plenty of room to spread out! A beautiful chef's kitchen includes a Wolf range and SubZero refrigerator. Entertain with ease on the elevated, spacious deck and terraced patio, surrounded by gardens and mature plantings. Sip your morning coffee or a cocktail on the peaceful screened porch, which boasts a beautiful stone fireplace. Retreat to a large primary en-suite with vaulted ceilings, gas fireplace and water views, while 2 generous sized guest rooms offer privacy and exterior access on the lower level. Only steps away is deeded ownership in a private landing on Areys Pond - perfect for boating, fishing or kayaking to the Namequoit River. This home also features a private dock with deep water access to Little Pleasant Bay and the Atlantic Ocean. Nestled in the prestigious Mayflower Point neighborhood, this exclusive area of Orleans presents the best the Cape has to offer!

Charming cozy home on three acres of waterfront on Little Pleasant Bay. Expansive views from your deck across a private sandy beach and out to the bay and ocean beyond. Terrific access for boating, sailing, and kayaking. The modest home has an open plan on the main level encompassing 1300+ sf. Fireplaced living room, dining, breakfast nook, and kitchen flow out to a spacious deck for grilling. Large bedroom with private bath and walk-in closet. In the finished walk-out basement you'll find an additional 1100+ sf with two beds, a full bath, and an additional living area. A delightful and simple Cape Cod getaway with some of the prettiest views you'll find. (Sale includes a 3 acre portion of the 4.1 acre property addressed as 32 Toms Hollow Lane, which 3 acre portion will be created by Approval Not Required Plan approved by the Orleans Planning Board prior to closing.)

Who says you can't have it all well you can. This home with a 2 bedroom boathouse on the water and 3 bedroom house on 1.90 acres on Pleasant Bay it's all one could ask for. The house on the hill could be torn down and you could build 5000 to 7000 sq.ft. home with all the bells and whistles even a pool just like the new homes surrounding it. This is about water and privacy. Have a boat with 2 homes 2 moorings more is better right. Boat over to Wequassett for lunch or dinner. Enjoy the ever change scene of sailboats kayaker's this is a feast for the eyes. Skip and a hop to Chatham and Orleans but private.

New 7300 sf Pleasant Bay estate on 1.2 acres built to the highest standards with top quality materials. The open floor plan features a LR with 18' of glass doors, a gas FP w/flanking built-ins and coffered ceiling, a DR w/ 12' slider, and a gourmet kitchen with granite counters, large island w/wine cooler, 2 sinks, 2 Bosch dw's, 48'' Wolf range w/double oven, a 48'' Sub-Zero fridge and a full size pantry. The 1st floor also includes the den and primary bedroom suite w/13' ceilings, luxurious bath and large walk in closet. The 2nd fl. has 3 bedroom suites with bay views, laundry, linen closet and an open loft area. 3 car garage w/lg suite above with a kitchenette and full bath. The walkout features a large entertainment area, kitchenette w/full-sized fridge, sink, DW and a full bath. The heated, salt water gunite pool with spa and autocover features a cabana with kitchenette, bath/changing room and an outdoor shower. The property includes a 1 of a kind renovated boathouse with panoramic views of the bay, kitchenette, bath, living room, oversized deck and stairs to the water to access your small boat, a private mooring for a larger boat and deeded beach access less than 1/4 mile away Property 71 Towhee Ln is a stunning residential property located in Orleans, Massachusetts. This magnificent home was built in the year 2024 and offers the epitome of luxurious living. Situated in a tranquil and picturesque neighborhood, this single-family home boasts a spacious and well-designed layout, providing ample room for relaxation and entertainment. The property encompasses a total of six bathrooms, ensuring convenience and comfort for the entire household. Additionally, there are two half bathrooms that offer additional convenience for guests and visitors. With a total finished area of 7,539 square feet, this residence is truly a grand masterpiece. Spanning across three stories, this dwelling provides a perfect balance of privacy and shared spaces. Each floor offers its own unique charm and purpose, creating a harmonious living environment for the occupants. The superior craftsmanship is evident throughout the entire home, with attention to detail and high-end finishes. The lot size of this property is an impressive 65,340 square feet, ensuring plenty of outdoor space for various activities and possibilities. The expansive yard is perfect for hosting gatherings, playing sports, or simply enjoying the serene beauty of the surrounding landscape. The well-manicured gardens and lush greenery create a welcoming and inviting atmosphere. Upon entering the home, one is greeted by a grand foyer that sets the tone for the rest of the residence. The open concept design seamlessly blends the living, dining, and kitchen areas, creating a spacious and versatile main floor. Large windows and glass doors allow an abundance of natural light to flood the interior, giving each room a warm and inviting ambiance. The kitchen is a chef's delight, featuring high-end appliances, custom cabinetry, and ample counter space. It is thoughtfully designed and equipped to handle any culinary endeavor. The adjacent dining area offers a perfect setting for formal dinners or casual meals with loved ones. The living area is a haven of comfort, with plush seating and a cozy fireplace as the focal point. This space is perfect for unwinding after a long day or hosting guests for a cozy gathering. The combination of high ceilings, tasteful decor, and quality finishes creates an atmosphere of elegance and sophistication. The upper levels of the home house the bedrooms, ensuring privacy and tranquility for everyone in the household. Each bedroom is generously sized, offering a peaceful retreat for relaxation. The master suite is a true sanctuary, featuring a luxurious en-suite bathroom and a spacious walk-in closet. The en-suite bathrooms throughout the home boast modern fixtures, sleek designs, and luxurious amenities, enhancing the overall sense of comfort and luxury. The lower

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 features 3 unique buildings. An approximately 7000 square foot main house, a guest cottage with pool and a boat house. This home contains the finest in craftsmanship and impeccable attention to detail. The large, open professional kitchen complete with top-of-the-line appliances, an oversized island and generous windows that overlook the bay makes this the natural centerpiece of the main house. Professional landscaping with multi-level stone walls and gardens makes this property look magazine worthy. A truly unique family compound where memories will be created for a lifetime.

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 features 3 unique buildings. An approximately 7000 square foot main house, a guest cottage with pool and a boat house. This home contains the finest in craftsmanship and impeccable attention to detail. The large, open professional kitchen complete with top-of-the-line appliances, an oversized island and generous windows that overlook the bay makes this the natural centerpiece of the main house. Professional landscaping with multi-level stone walls and gardens makes this property look magazine worthy. A truly unique family compound where memories will be created for a lifetime.

Crown Jewel of Pleasant Bay - Exquisitely designed and built by Eastward Homes, this upscale home has panoramic views of Pleasant Bay & ocean beyond. The superior coastal design & fine craftsmanship including extensive crown moldings, beadboard, & built-ins has cutting edge technology and creates a high degree of originality yet achieves a casual elegance. Walls of glass & multiple decks were designed to enjoy the breathtaking views from sunrise to sunset. The sunlit home has an open floor plan, consisting of a chef's dream kitchen, curved window-lit dining area, sunroom, great room w/ coffered ceiling, wet bar, built-in bookshelves, & gas fireplace. There's a large 1st floor primary suite with gas fireplace & spa bath. Two additional bedroom suites are on the 2nd floor w/ a family room & office plus another large bedroom & bath in the walk-out lower level, an exercise/game room & entertainment area.

Crown Jewel of Pleasant Bay - Exquisitely designed and built by Eastward Homes, this upscale home has panoramic views of Pleasant Bay & ocean beyond. The superior coastal design & fine craftsmanship including extensive crown moldings, beadboard & built-ins has cutting edge technology and creates a high degree of originality yet achieves a casual elegance. Walls of glass & multiple decks were designed to enjoy the breathtaking views from sunrise to sunset. The sunlit home has an open floor plan, consisting of a chef's dream kitchen, curved window-lit dining area, sunroom, great room w/ coffered ceiling, wet bar, built-in bookshelves, & gas fireplace. There's a large 1st floor primary suite w/ gas fireplace & spa bath. Two additional bedroom suites are on 2nd floor w/ a family room & office plus another large bedroom & bath in the walk-out lower level plus an exercise/game room & entertainment area. A 3 car garage and Beautifully landscaped grounds, patio w/ inground heated saltwater pool & spa. Deeded access to sandy beach for swimming & boating. Mooring per Harbormaster. A rare opportunity to own a spectacular new home built & designed by one of Cape Cod's finest builders. This property is a 45,750 sq. ft. parcel with a view easement to the water and access and easements to use the beach. See Plans in Documents Call for more information.

SALTWATER WATERFRONT! Wake up to breathtaking water views from almost every room! As you walk in you will be greeted by cathedral-beamed ceilings & brass inlay Brazilian cheery floors. French doors in the breakfast nook open onto a sprawling teak deck. Cozy up by the wood-burning fireplace in the sunken living room or gather for formal dinners in the elegant dining room with a wet bar. The kitchen is a chef's dream, featuring Italian tile countertops & terracotta floors. Viking appliances and a Sub-Zero refrigerator. Relax and reconnect with nature on the multi-level decks, all with water views. The two-car garage features a bonus room above currently being used as a home gym. Additional features include -on-site boat storage, a custom teak outdoor shower, full house generator, bunk room, double washer & dryer, plenty of closets and storage, lush perennial landscaping with a sprinkler system. The house has been tastefully decorated and is being sold fully furnished.

SALTWATER WATERFRONT! Wake up to breathtaking water views from almost every room! You can't beat the tranquility of Pleasant Bay from this waterfront haven. With three finished floors, the living space flows seamlessly throughout. As you walk in you will be greeted by cathedral-beamed ceilings & brass inlay Brazilian cheery floors. French doors in the breakfast nook open onto a sprawling teak deck. Cozy up by the wood-burning fireplace in the sunken living room or gather for formal dinners in the elegant dining room with a wet bar. The kitchen is a chef's dream, featuring Italian tile countertops & terracotta floors. Viking appliances and a Sub-Zero refrigerator. Relax and reconnect with nature on the multi-level decks, all with water views. Immerse yourself in the beauty of the Atlantic Flyway, a haven for birdwatchers. Tranquility awaits in the airy primary suite, with a private deck, walk-in closet, and sitting area. The two-car garage features a bonus room above currently being used as a home gym. Additional features include - on-site boat storage, a custom teak outdoor shower, full house generator, bunk room, double washer & dryer, plenty of closets and storage, lush perennial landscaping with a sprinkler system, and captivating water or garden vistas from every window. With over 3,000 sq feet, there is a special place for everyone to enjoy. The house has been tastefully decorated and is being sold fully furnished. Don't miss this rare opportunity to own a piece of paradise. Shown by appointment only.

Nestled in a rather secret neighborhood in East Orleans, 6 Joy Lane presents an unparalleled opportunity to own a residence of timeless elegance on a coveted corner lot. This exclusive property is a serene retreat surrounded by magnificent lush gardens, secret paths and unique specimen trees and plantings all created by an award winning landscape architect. There is also room for a pool. Step inside, and the interior seamlessly combines sophistication with a welcoming ambiance. The great room, a hub for socializing, boasts a fireplace that becomes the focal point for gatherings. The open-concept kitchen and dining area feature a massive bar with seating for five. Natural light floods the sunroom, offering a tranquil space to bask in the warmth of the surroundings. The open and inviting floor-plan reveals three thoughtfully designed bedrooms on the first floor, including a private primary suite. The finished lower level provides additional space and flexibility.

This new luxury Eastward Home currently under construction enjoys a private, natural setting and a wonderfully convenient location providing easy access to Brewster's Bay beaches, Nickerson State Park, The Cape Cod Rail Trail and Orleans Village. At the end of the long, circular drive one enters the home by the wraparound farmer's porch. The cathedral great room encompasses the living, kitchen and dining spaces. V-groove wood ceilings, built-ins and extensive millwork adorn the living spaces, the shed dormer brings tremendous light and architectural interest. The Chef's kitchen with Wolf/Subzero appliances, walk-in pantry and a substantial kitchen island is open to the dining area and the south facing sunroom which adds light and depth to the living area. Complete first floor living arrangement includes mud room, laundry, private office and the primary bedroom suite. Upstairs are two guest bedrooms and a full bath, the 4th bedroom suite above the garage has a private stairway. The lower level offers 1,000 sq ft of finished recreation space with a full bath. The inground pool with integrated spa and auto-cover is the focal point of the extensive patio and landscape design.

WATERFRONT. DEEPWATER DOCK. DEVELOPMENT POTENTIAL Sail/power to Nantucket Sound from your private, licensed dock w/ 7-foot depth at low tide. Set on the Herring River south of Lower County Road, the 2-lot property offers safe harbor & immediate boating access to the open ocean. Dock & floats are substantial, well-maintained & accommodate multiple craft including a 35-foot sailing or power yacht. Comprising two discrete lots, the property offers myriad development opportunities including building expansion, new construction, guest house, swimming pool & more; a new 6-bedroom septic systems has been designed and permitted. The upper lot hosts a well-maintained 4BR Cape w/ great water views & rental history. The undeveloped waterfront lot is beautiful, level, sunny and open...a magical setting for games, picnics, clambakes & cookouts. Set in a quiet, private neighborhood close to Nantucket Sound beaches (Belmont & Pleasant Road beaches are less than .7mi away. Move-in ready, turnkey.

Potential abounds with this Main Street/Route 6a mixed use property with great visibility and ample private parking. Front and side entrances ensure privacy and accessibility. The first floor has five private offices, one with a fireplace, two waiting/reception rooms, closet storage and an accessible rest room. The second floor is a private residential unit with two bedrooms and one bath, and the lower level offers another five private offices, a rest room, entrance foyer and grade level access. Nicely landscaped property with irrigation and existing signage on 6a. Being close to the Orleans town line affords quick, easy access to Route 6.

Welcome to Orleans! From Nauset Beach to Skaket Beach, from Town Cove to Pleasant Bay,Crystal Lake, Pilgrim Lake, the Cape Cod bike trail... This town has it all!This charming home nestled over a scenic wetland enjoys the ever-changing seasons at your back door!Recent full renovation. This is the perfect summer get-away or year round home!

Re-Introducing 30 Hayward Lane, now boasting a fresh new look that elevates its timeless appeal. This meticulously maintained home is located in one of the most coveted neighborhoods in East Orleans. Privacy and tranquility found here on 1.9 waterfront acres on Little Pleasant Bay. This is the perfect house for entertaining and outdoor activities. There are water views from virtually every room that are spectacular and panoramic. The first-floor primary bedroom offers complete serenity to unwind and rejuvenate with a fireplace, sitting area and his & her bathrooms. There is a large office, a bonus room above the garage as well as a lower level offering room to expand. Enjoy the gym on a rainy day or take your boat out when the sun shines for a day of fishing. From your private path to the water you can shellfish, swim and paddle. With its unparalleled location and craftmanship this home is the epitome of coastal living and a legacy to share with family & friends.

Re-Introducing 30 Hayward Lane, now boasting a fresh new look that elevates its timeless appeal. This meticulously maintained home is located in one of the most coveted neighborhoods in East Orleans.Privacy and tranquility found here on 1.9 waterfront acres on Little Pleasant Bay. This is the perfect house for entertaining and outdoor activities. Wide-pine floors, cozy fireplaces and sumptuous bedrooms make this home warm and inviting. There are water views from virtually every room that are spectacular and panoramic.The first-floor primary bedroom offers complete serenity to unwind and rejuvenate with a fireplace, sitting area and his & her bathrooms. There is a large office for everyone to work from home, a bonus room above the garage as well as a lower level offering room to expand. Enjoy the gym on a rainy day or take your boat out when the sun shines for a day of fishing. From the private path to the water you can shellfish, swim and paddle.With its unparalleled location and craftmanship this home is the epitome of coastal living and a legacy to share with family & friends.

Lovely two-story Cape Style home on a large private lot on Pleasant Bay. Situated between the Cape Cod National Golf Course and the Oceanfront Wequassett Resort. This recently renovated home has three large bedrooms, two full baths and many extras. Large living room is skylit with cathedral ceiling and French doors that open onto an ample deck. Eat in kitchen with upgraded appliances, granite countertops and peninsula. Additional features include a gas fireplace, outdoor shower, and an emergency generator. Laundry in the master bedroom plus additional washer/dryer in basement. Tankless on-demand water heater. Generous storage space in easily accessible attic, full basement and extra space in garage. Septic has been regularly serviced. This is an ideal year-round home or a vacation get-away. Sold "AS IS"

Welcome to 82 Main Street, one of Orleans most extraordinary settings in one of the Cape's most coveted villages. Elegantly restored and rich in tradition and character, this impeccably maintained, gracious 9 room enchanting antique encompasses just under 3000 square feet of living space and offers 5 bedrooms, 2 1/2 baths, formal living and dining rooms, a family room, sitting room, a brand new spectacular cook's kitchen with Omega cabinets, granite countertops and premium appliances and an inviting screened porch and two sundecks to enjoy the starry Cape Cod nights. The flexible floor plan blends the charm of yesteryear with the modern amenities of today and lends itself to both a first or second floor primary bedroom with serene water views of Town Cove. Numerous updates include new heat and AC, hot water heaters, paint in and out, new baths, new roof and many new windows. The charming residence exudes character and timeless style inside and out and features wood floors throughout, 2 fireplaces and one of Orleans most peaceful, tranquil settings. Its abundance of space for both family and friends and proximity to Orleans Village Center just add to this stately homes appeal.

New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and offers vast water views. More views are served up in the chef's kitchen, which features a Wolf gas range, a large island with seating, and doors to an expansive deck overlooking Crows Pond. A cased opening from the kitchen leads to the formal dining room with traditional raised panel walls and a butler's pantry with a wet bar. The three-level home includes a quiet office area for work, a lower-level gym for working out, and an outdoor pool and indoor sauna for pure relaxation. An elevator makes it easy to move between floors. The lower level also has a guest suite with a full kitchen and living room. The home, close to Lighthouse Beach, comes fully furnished and professionally decorated.

New co-ownership opportunity: Own one-eighth of this turnkey home, professionally managed by Pacaso. Set on 2.74 acres, Fox Hill offers a private sanctuary with 11,000 square feet of sophisticated coastal luxury. The renovated retreat has stunning views of Crows Pond, Eastward Ho and Pleasant Bay, and a private boat dock. The open, airy living room has a stone fireplace and window seats, and offers vast water views. More views are served up in the chef's kitchen, which features a Wolf gas range, a large island with seating, and doors to an expansive deck overlooking Crows Pond. A cased opening from the kitchen leads to the formal dining room with traditional raised panel walls and a butler's pantry with a wet bar. The three-level home includes a quiet office area for work, a lower-level gym for working out, and an outdoor pool and indoor sauna for pure relaxation. An elevator makes it easy to move between floors. The home, close to Lighthouse Beach, comes fully furnished and decorated.

Overlooking beautiful Crows Pond, this exquisite property offers a myriad of opportunities with a 6 BR septic and conceptual plans for a 4 BR residence, an existing two bedroom, two bath home that feels like a private sanctuary and exudes a perfect blend of luxury living with an elegant coastal charm. Located on 1.8 acres across from Eastward Ho Country Club, the property offers a multitude of expansion opportunities. The home highlights custom craftsmanship and detailed finishes and provides ample space for intimate or large gatherings with generously proportioned indoor and outdoor living spaces. The great room with gas fireplace and dining room are view-filled and adjoin a sunroom with a wood burning fireplace. The kitchen has all the amenities as well as a sitting area that opens to a patio with a fire pit. The bedrooms afford privacy with a first floor primary suite and a second level sitting room and en suite bedroom-all with water vistas. This home is a perfect Chatham retreat.