Martha’s Vineyard Homes with Guest House

Find a variety of homes with a guest house on Martha’s Vineyard, whether you are looking for a seasonal home or year round residence. Martha’s Vineyard has beautiful oceanfront properties, homes with wooded acreage, Cape style homes, and much more. Browse homes on Martha’s Vineyard below. 

Houses for Sale with Guest House on Martha's Vineyard

Call Ocean Park Realty at 508-693-4210 if you have questions about any of these properties or would like to set up a private tour.

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6 North Vine Lane West Tisbury MA 02575

West Tisbury, MA6 North Vine Lane

Price$3,200,000

Est. Mortgage: $/month

MLS Number 39145

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathroom 4.5
  • Acreage 3

Exquisitely maintained and charming main house, guest house, barn and 3-car garage are all in perfect, move-in condition. Located in the heart of West Tisbury, off a private, paved lane, the stunning oak post-and-beam main house and other handsome buildings are spacious and bright with all rooms enjoying high or vaulted celings. Flanked by woods and green spaces, which add to the sense of rural beauty and privacy, the 3-acre property is minutes from Alley's General Store, Sepiessa/Tisbury Great Pond, Long Point Beach and the bike paths. The main house features high efficiency hydronic heat, central air, three master bedrooms (one on first floor) with luxurious en-suite bathrooms, a chef's kitchen with walk-in pantry, mudroom/laundry room, half bath and a farmer's porch with a large outdoor shower. The main house has many thoughtful and unique details like cast brass knobs and hinges on all the doors, radiant heat in both the floors and walls of all baths, and soundproofed insulation. All finishes are pristine. The insulated one bedroom guest cottage has farmhouse charm similar to the main house with heat and central AC, full bath and laundry area, with a 2nd outdoor shower. French doors open to a lush garden with a bluestone terrace and granite picnic table. The classic New England post-and-beam barn has a concrete foundation, three stalls, two heated rooms and loft, as well as water and electricity. The stalls could be easily removed for a home office, artist's studio, writer's retreat or pool house. This beautifully landscaped property has multi-zoned irrigation and features stone walls, gardens and paddocks. The property has a 20KW Generac generator and separate propane tank to run all services.

Listed by Robert Kenney of Tea Lane Associates

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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5 Tree Frog Lane Chilmark MA 02575

Chilmark, MA5 Tree Frog Lane

Price$1,595,000

Est. Mortgage: $/month

Pending

MLS Number 39074

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathroom 2
  • Acreage 4

This tastefully designed post & beam home is privately sited on 4 acres overlooking a peaceful & pastoral setting with stone walls a charming vegetable garden with raised beds. Many nice features include wide pine wood floors, a living and dining room with fireplace, a country kitchen breakfast area, cathedral ceiling and first floor master. The second floor includes a small loft, 3 bedrooms and bath. Outside shower off the back deck. Being sold fully furnished, turnkey. There is also a large storage shed and barn. A guest house can be permitted in 5 years. Close to beaches, Menemsha and Chilmark Village. A must see!

Listed by Brenda Galligan of Karen M. Overtoom R.E.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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219 Herring Creek Road Vineyard Haven MA 02568
Active With Contract

MLS Number 38913

  • Residential
  • Bedrooms 6
  • Bathroom 3.5
  • Acreage 1.5

IDYLLIC COUNTRY LIVING NEAR LAKE TASHMOO AND VINEYARD SOUND BEACHES. Set on 1.5 rolling acres and surrounded by beautiful stone walls, lush gardens and landscaping, this handsome compound with a 4-bedroom Main House and a 2-bedroom Guest House offers an idyllic and private island retreat. The MAIN HOUSE is post-and-beam construction and boasts rustic charm throughout four levels of living space. Oversized windows flood the home with golden sunlight and there is a covered wraparound porch and spacious mahogany deck, perfect for indoor-outdoor living and entertaining during the summer months. The detached GUEST HOUSE is privately sited with its own parking area and features an open Living/Dining/Kitchen area with vaulted ceilings and sliding glass doors that out onto a second-story deck -- plus two bedrooms and a full bath. There is also a loft and walk-out lower level that offers additional bonus and storage space. This charming country compound is less than a mile to Tashmoo Town Beach and nearby boat launch as well as Wilfrid's Pond Preserve and Tashmoo Preserve, both with access to walking trails and Vineyard Sound beaches. Mink Meadows Golf Course and Vineyard Haven shops, restaurants and ferries are also just a short drive away. This special property offers a myriad of possibilities as a retreat for gathering family and friends and/or a wonderful rental investment property (rental income history available). The expansive, level and beautiful backyard would also be ideal for an in-ground pool!

Listed by Wendy Harman of Point B Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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5 Farm Path Oak Bluffs MA 02557

Oak Bluffs, MA5 Farm Path

Price$1,299,900

Est. Mortgage: $/month

Active With Contract

MLS Number 38957

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Acreage 0.6485

Beautifully and well maintained cape, located right at the center of the island on a large lot with enough room and capacity for an EXPANSION AND A POOL. Septic system was just upgraded (2021) to legally accommodate a 6 bedroom home. You could potentially build a GARAGE, and a GUEST HOUSE. As you walk in the home you will find an open floor plan with Brazilian cherry flooring throughout the house, a beautiful kitchen with white cabinets, with quartz countertops and stainless steel appliances. Some of the recent upgrades this year include a new irrigation system, and a new water heater. Exterior shingles and all windows were replaced in 2019, both bathrooms were upgraded in 2017. Come and see what this house has to offer.

Listed by Antulio Goncalves of Premiere Broker Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 MA 02539

Edgartown, MA30 Mill Hill Road

Price$3,950,000

Est. Mortgage: $/month

Active With Contract

MLS Number 38881

  • Residential
  • Bedrooms 4
  • Bathroom 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 C. Smith of Portfolio Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

"Based on information submitted to MA_LINKMV as of January 26, 2022 . 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."

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