Martha's Vineyard Estates & Multi Generation Homes

View the latest listings for estates & multi-generational homes on Martha's Vineyard below. 

Martha's Vineyard Estates & Multi-Generational Homes for Sale

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15 Beach Plum Meadows

Edgartown, MA15 Beach Plum Meadows

Price$5,495,000

Est. Mortgage: $/month

MLS ID 38976

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 5.5
  • Acreage 1.64

A spectacular generational estate designed with entertaining in mind. This private 1.64-acre property is located at the end of one of the most sought-after streets in Katama: Beach Plum Meadows. The main residence features three floors all of which have ultra-high ceilings and a ton of natural light. The first floor offers three large bedrooms, two full bathrooms, laundry, and an office. All of the rooms have sliding doors out to the expansive deck / porch. The second floor offers spectacular sunsets and has an open floor plan with a chef's kitchen, two dining areas, a living room with a gas fireplace, and a full bathroom. There are multiple sliding doors out to the wrap-around deck where one will enjoy the Katama breeze and fabulous sunsets. The walk-out lower level has a large bedroom, full bathroom, additional laundry room, a gym, and sports court! Each floor has elevator access. The detached structure features a three-car garage, large office, full bathroom, and deck with sunset and farm views. There is an oversized three-car garage for all your storage needs. The property comes with recently purchased and installed solar panels which not only completely cover the electric bill but also produce a surplus of energy / credit. The property features beautiful landscaping and an open lawn that offers plenty of space for a pool.

Listed by Jarrett Hurwitz of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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104 & 111 Old Herring Creek Road

MLS ID 38896

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathrooms 5.5
  • Acreage 9.5

SWORDSPOINT is one of the Island's most spectacular oceanfront properties, offering a premier, one-of-a-kind location of natural beauty and seclusion with 9.6 acres of land and ca. 640 feet of private beach. The two abutting properties unfold to dramatic unobstructed panoramic views of ocean, ponds, dunes, coastlines and the Elizabeth Islands. Access to these properties is through a very large private estate with parklike grounds. The renovated 4 bedroom, 4.5 bathroom residence is harmoniously tucked into the gently rolling grounds of the 5+ landscaped acres and is architecturally sensitive to the pristine charm of its surrounding environment. The first floor offers an open plan living and dining room, a kitchen with wetbar extension, a dining nook, and powder room; a hallway to the west leads to a first floor bedroom, full bathroom and family room. The northern and eastern sides of the first floor are wrapped by a screened porch. The second floor offers the Master Bedroom with en suite bathroom, a private balcony deck; and two additional bedrooms, each with a full en suite bathroom. A path from this residence leads to 445 feet of private beach. The abutting 4.3 acre parcel offers a 1970s one level residence with cathedral ceiling, common room, 3 bedrooms, 1 bathroom, and a first level and rooftop deck. This parcel has significant buildable acreage with diverse topography and a path leading to its private beach. Together these two properties offer unprecedented opportunities in this incredibly beautiful area of the north shore. Each property comes with a 6 bedroom septic system in place.

Listed by Patty Kendall of Kendall & Kendall

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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30 Mill Hill Road

Edgartown, MA30 Mill Hill Road

Price$3,950,000

Est. Mortgage: $/month

Active With Contract

MLS ID 38881

  • Residential
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 13.93

MILL HILL FARM, EDGARTOWN - UP ISLAND FEEL, SHORT DISTANCE TO MAIN STREET. Perched on a grassy knoll between downtown Edgartown and Katama, this nearly 14-acre, vintage farm has been thoughtfully stewarded by one family for three generations. Magnificent in its natural beauty and open space, this property offers a unique opportunity to renovate or expand the original homestead into a remarkable estate. Your vision will transform this property into a generational asset that will be truly one-of-a-kind. Expansive, pastoral views surround the 1850 farmhouse that once served as the home and office of the local doctor whose other passion was farming. The existing barn has recently served as a two bedroom guest house and could easily be renovated and remain as a guest house, a unique pool house, or returned to its original function. The additional structures include a two-car garage, a tool shed, coop and smokehouse. Protective covenants are in place to preserve the unspoiled splendor of Mill Hill Farm.

Listed by Brian Smith of Portfolio Real Estate,Inc.

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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16 Kent Harbor Road

Edgartown, MA16 Kent Harbor Road

Price$2,395,000

Est. Mortgage: $/month

MLS ID 38888

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathrooms 1.5

RARE OPPORTUNITY TO OWN IN DOWN HARBOR ESTATES. Located on a full one-acre parcel in the highly-coveted Down Harbor enclave, this 1970's beach house offers the opportunity to enjoy all of the unique and desirable Down Harbor lifestyle amenities. Located approximately one mile from Edgartown Village and two miles from South Beach, the Down Harbor neighborhood includes access to a stunning private association beach and dinghy dock on Katama Bay PLUS the possibility to secure a slip on the association dock (awarded through a 3-year lottery). This property enjoys access from both Kent Harbor Road and Guernsey Lane -- and a short stroll down a nearby path takes you to the Katama Bay beach and dock area. This classically styled 1970's contemporary can be enjoyed as-is as a casual island getaway, transformed into a modern-chic beach retreat -- or used as a residence while you make plans to build your signature custom home. There is a 4-bedroom septic system in place that was installed in 2005. Properties in Down Harbor rarely become available and this opportunity is not to be missed. NOTE: Sellers will be accepting offers at 5:00 PM on Monday, October 18th. Estate rules apply.

Listed by Wendy Harman of Point B Realty LLC

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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140 Merry Farm Road

West Tisbury, MA140 Merry Farm Road

Price$6,100,000

Est. Mortgage: $/month

MLS ID 38710

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathrooms 5
  • Acreage 28.3

This is a lovely estate with over 28 private acres in a pastoral setting in West Tisbury. The main home over looks a spring fed pond, old stone walls and open meadows. There is a private pool nestled on the side of the home surrounded by mature gardens. The home is in wonderful condition and has so many private spaces that lend themselves to the outdoors. There are three additional dwellings onsite making it easy to create a family compound as well as housing for help with the property or caretaking. There is also an impressive barn with 8 stalls and a turn out shed. This is a combination of three parcels combined (19.1, 7.1 and 1.4 acres). The Land Bank abuts the southwest part of the parcel ensuring peace and privacy.

Listed by Jill Napior of Tea Lane Associates

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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19 Locust Lane

Aquinnah, MA19 Locust Lane

Price$9,995,000

Est. Mortgage: $/month

MLS ID 38453

  • Residential
  • Mls Status Active
  • Bedrooms 7
  • Bathrooms 4.5
  • Acreage 17.76

Incredibly rare and PRIVATE 17.76 acre lush, green, beautiful high country erosion-free Aquinnah Hilltop Estate with 6,100+ sf 6 bed, 3.5 bath, winterized main house with radiant floors, outdoor shower, 2 beautiful + large fireplaces, Tuscan fireplace grill, chef’s kitchen, roof deck, stone patio with gas line connected to outdoor grill, and water and island views from every room in the house, as well as a 1,000+/- sf 1 bed, 1 bath winterized guest house with full kitchen, and large deck overlooking the property and the Elizabeth islands + Vineyard Sound, and a 3 car heated garage. 2 min to the Atlantic Ocean and 5 min to the Vineyard Sound. 1 minute drive to Gay Head Cliffs + Lighthouse. Live off the grid w/ 80KW Kohler generator, 2000 gallon propane tank, fenced in garden, streams, stone walls, industrial tankless water heater, Viking, GE, & Bosch stainless steel appliances! Room to entertain over 100 people.

Listed by Jesse Greenstein of Douglas Elliman MV

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1005 Main Street

Vineyard Haven, MA1005 Main Street

Price$11,600,000

Est. Mortgage: $/month

MLS ID 38460

  • Residential
  • Mls Status Active
  • Bedrooms 9
  • Bathrooms 7
  • Acreage 0.8333

Welcome to 1005 Main St! Located at the northern tip of Martha's Vineyard comes one of the most beautiful oceanfront properties on the entire island. A 5,050 square foot estate with an incredible deck, private beach, lovely painted floors and a ton of space for entertainment is now on the market. A feeling of privacy and peace surrounds this property due to the amazing landscaping, views, and unique character that this home brings. Come watch the sunset from the very spacious and freshly painted deck and be taken away into the immersive environment of the immaculate surroundings. Call and set up an appointment today!

Listed by Ryan Knoechelman of Rovi Homes

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 & 22 Cataumet Avenue

MLS ID 38212

  • Residential
  • Mls Status Active
  • Bedrooms 11
  • Bathrooms 8
  • Acreage 1.55

This magical beachfront estate is located in the heart of the exclusive West Chop community on a double lot with 200 feet of beach dune frontage. There are four classic shingle style structures complimenting the property of which all enjoy enchanting views across the expansive rolling lawns and gardens to the beach and breathtaking sunset views over the Vineyard Sound. There are two, turn of the century, five-bedrooms homes, each with extraordinary character including wrap-around porches and 2nd floor balconies. Additionally, there is a charming 1-bedroom/1-bath guest house with cathedral ceiling living room and fireplace, and a studio building offering a fitness area and sauna. This unique compound, set within mature vegetation offering complete privacy, beautiful gardens and specimen trees is just a short walk to the West Chop Club with Mink Meadows Golf Club and downtown Vineyard Haven just minutes away. This is a very special Vineyard property that must be seen if considering the best waterfront offerings.

Listed by Gerrett Conover of Landvest MV

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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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42 Slough Cove Road

Edgartown, MA42 Slough Cove Road

Price$8,495,000

Est. Mortgage: $/month

Pending

MLS ID 38041

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathrooms 6
  • Acreage 5.2

IN-CONSTRUCTION: ULTRA LUXE 5-ACRE ESTATE IN KATAMA. Construction is underway on this luxurious modern farmhouse estate, near South Beach in Katama. Located on 5.2 private acres and sited amid a natural landscape of meadows, eastern cedar, scrub and post oaks the south-facing property enjoys beautiful afternoons and brilliant sunsets with the sounds of the ocean nearby. Exposed beams and soaring high ceilings in the main living spaces offer the grandness of an extraordinary luxury home while providing an air of casual barefoot elegance. This stunning home will feature top-notch architectural details and craftsmanship throughout (specifications available upon request). The floor plan was perfectly designed to maximize indoor-outdoor living and entertaining around the resort-like backyard with large screened porch, pergolas, wood-burning fireplace, a bluestone terrace and 20'x40' charcoal gunite pool with lounge decks and built-in whirlpool spa. This unique property offers the opportunity to create your own signature island retreat -- perfectly blending farm, field and seaside living and creating an idyllic home to gather family and friends for many years to come. The expansive multi-acre parcel will allow for a tennis court, extensive gardens, a horse barn or other possibilities. Get in early and enjoy the opportunity to customize colors and finishes. This property is slated for completion by Summer, 2022!

Listed by Wendy Harman of Point B Realty LLC

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$
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$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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47 and 31 Hatch Road

Vineyard Haven, MA47 and 31 Hatch Road

Price$7,450,000

Est. Mortgage: $/month

MLS ID 37396

  • Residential
  • Mls Status Active
  • Village West Chop
  • Bedrooms 7
  • Bathrooms 6

Elegant and refined, this exceptional estate property is sited on 1.3 acres. Located in the coveted Hatch Road neighborhood, this 2 home property boasts incredible architectural detail with all the modern amenities. As you enter the property via a winding gravel drive past an expansive lawn, you come to a setting not found so close to downtown Vineyard Haven. The main house dates back to 1900 and has been meticulously renovated and features a gourmet kitchen open to a dining room with french doors looking out to a rose garden, a spacious first floor master bedroom suite, dramatic great room with 20 foot ceilings with wood detail, and an inviting screened-in porch leading out to a private brick patio. The home features 4 additional guest bedrooms on the second floor. The guest house was designed in 2008 and built by a prominent Martha’s Vineyard builder. The wood detail includes aged lumber and the walls are warmly lined with recycled barnwood. Stunning museum quality terrazzo flooring inlaid with wood beams and terrazzo countertops are featured in the spacious great room, gourmet kitchen and dining room. Other guest house amenities include two bedrooms with en suite baths each with stunning wide plank flooring, and a spacious loft perfect for a home office. A home gym/pool house, outdoor kitchen, 2 car-garage and pool complete this rare offering.

Listed by Alyssa Halisky of Wallace & Co. Sotheby's

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$
%
$/month over payments
Federal 30-year interest rate: 3.1% last updated on Nov 24, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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"Based on information submitted to MA_LINKMV as of November 30, 2021 . All data is obtained from various sources and has not been, and will not be, verified by broker or MA_LINKMV.  All information should be independently reviewed and verified for accuracy.  Properties may or may not be listed by the office/agent presenting the information. NOTICE: Many homes contain recording devices, and buyers should be aware they may be recorded during a showing."