Martha's Vineyard Homes with Guest House

Below are current listings for homes with a guest house on Martha's Vineyard.

Homes with Guest House for Sale on Martha's Vineyard

If you have any questions or would like to schedule a private tour, call Landmarks Real Estate at 508-693-6866.

Save time & effort! Create an account to save your favorite listings & get notifications when similar properties become available.

31 & 33 Flanders Lane

Chilmark, MA31 & 33 Flanders Lane

Price$2,250,000

Est. Mortgage: $/month

Pending

MLS ID 38899

  • Residential
  • Mls Status Pending
  • Bedrooms 3
  • Bathrooms 3
  • Acreage 2

Light filled main and guest house set on two beautiful acres designed by post war pioneer architect William Smull known for his mid-century houses.With views of Menemsha Pond, Vineyard Sound and Aquinnah and within walking distance to Menenmsha Harbor, fish markets, and Menemsha Beach. Included is deeded access to Menemsha Pond where you can leave your skiff, kayaks or paddle boards for use on the pond.The main house has two bedrooms, two baths and open kitchen/dining/living area with large deck to enjoy the view. Guest house is entirely self-contained with one bedroom, kitchen, bath and two sitting areas yet is accessible from the main house by a charming foot bridge over the stream. Large yard with lily pond, grape vines and blueberry bushes.

Listed by Brenda Codding of Up Island Realty

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

219 Herring Creek Road

MLS ID 38913

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathrooms 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: 3.1% 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

5 Farm Path

Oak Bluffs, MA5 Farm Path

Price$1,299,900

Est. Mortgage: $/month

MLS ID 38957

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 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 Downey Realty Group

$
$
%
$/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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

68 Twentieth Street South

Edgartown, MA68 Twentieth Street South

Price$1,600,000

Est. Mortgage: $/month

MLS ID 38917

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 3
  • Acreage 0.62

TURN KEY- READY TO MOVE RIGHT IN. Sometimes you get lucky in life, and find a house that is perfect for you and your family. If you are looking for a house that has four bedrooms, two of the bedrooms are ensuite', another full bathroom, a living room, and a large family room, a two car garage, and a basement that is clean and dry with a ping pong table, but it is waiting to be finished. AND room for a pool, and a 900 sq ft guest house, AND in Edgartown that is affordable. I think maybe you just got lucky!! If you like to hike and enjoy the peacefulness of being in Nature, Pennywise Preserve is a stone's throw away. The house has been well taken care of by the present owners, having installed a new heating system, a new water heater and a few new pieces of furniture. This property is convenient to all the down-island towns and beaches. At the end of the street is the bike path and a bus stop so you can bike or ride into the village of Edgartown. For the current owners, this property has been a great rental property. This past year, using 3 weeks during the summer themselves, the owners rented 6 weeks at $4200 a week. Renting during the shoulder seasons would bring in more income. Don't miss taking a tour at this great property!!

Listed by Carol McManus of C McManus Realty Group

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

29 Jernegan Avenue

Edgartown, MA29 Jernegan Avenue

Price$929,000

Est. Mortgage: $/month

Active With Contract

MLS ID 38902

  • Residential
  • Bedrooms 2
  • Bathrooms 1.5
  • Acreage 0.73

PRISTINE EDGARTOWN COTTAGE WITH EXPANSION POTENTIAL - Located just 2 miles from the Village, this charming cottage has maintained all of its charm, while being transformed for today's lifestyle. Ready for immediate occupancy for year round living or start booking your 2022 rentals and enjoy this smart investment. The property is one lot, but divided to appear as two separate lots (2 driveways), making the addition of a guest house non-disruptive while living in or renting the main house. With new wood floors, fresh paint and air conditioning you can start enjoying all that the property and location has to offer. The floor plan is ideal, with a large kitchen that's open to the dining room. The kitchen's east facing windows overlook the lawn and allow wonderful morning light to pour in. Entertaining is easy with the Sub Zero fridge and freezer, Miele dishwasher and gas range. The living room has ample space for several people to gather. The outdoor living space is phenomenal as well, with a deck leading to an expansive brick patio, large yard and outdoor shower. Additionally, there is a 300 square foot outbuilding, providing flexible space to spread out on this 3/4 acre property. Expansion would be a breeze here, as there is already a 5 bedroom septic system in place and town water is just a few doors down (cost estimate available upon request). There is an existing garage/guest house foundation, which is the first step in creating an income producing compound. The property is approximately .5 miles from the Sengekontacket boat launch, which is an ideal kayak and paddle board spot. For those who prefer hiking and biking over water sports, access to miles of Land Bank trails is also close by. Agent has owner interest.

Listed by Jen O'Hanlon of Wallace & Co. Sotheby's

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

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.

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

145 Midland Avenue
Active With Contract

MLS ID 38894

  • Residential
  • Bedrooms 3
  • Bathrooms 2
  • Acreage 0.3196

Classic Vineyard 2 story farmhouse hidden away on a large 13,900 sq. ft. lot. Great location between Lake Tashmoo and Vineyard Haven. Gas fireplace in living room, a sweet balcony off the 2nd floor bedroom and 2 large exterior decks (one covered) helps expand your living area. The partially finished walkout basement adds an aditional 300 sq. ft. of living space!. Plus...an outdoor shower, 2 sheds and a water feature fish pond! Room for guest house! Seller to credit Buyer, $15,000 at closing.

Listed by Doug Reece of RE/MAX on Island

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

56 Robinson Road

Edgartown, MA56 Robinson Road

Price$3,835,000

Est. Mortgage: $/month

MLS ID 38874

  • Residential
  • Mls Status Active
  • Bedrooms 4
  • Bathrooms 3.5
  • Acreage 0.5

NEW CONSTRUCTION, with POOL, 1/2 mile from the heart of EDGARTOWN VILLAGE! Location, Location! Approx. 3,500 square feet of open living space. The Great Room has a dramatic Two Story wall of windows which surround a gas fireplace and overlooks a 14 x 30 foot in ground pool. In addition to the dramatic Great Room there is a first floor study, a first floor master-en-suite, a mud room and separate laundry area. The Gourmet Kitchen, with it’s central island, opens to the dining room which flows into the Great Room. The second floor offers a second master-en-suite, as well as two additional guest bedrooms which share a full bath. The plot can have up to SIX BEDROOMS, a future guest house and/or a future detached bedroom. All of this, and only a 1/2 mile to the heart of Edgartown Village. The property is also close to the Library, Girls/Boys Club, public tennis courts, public playscape and the bike path.

Listed by Michele Casavant of Vineyard Village Realty

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

200 Red Coat Hill Road
Pending

MLS ID 38871

  • Residential
  • Mls Status Pending
  • Bedrooms 5
  • Bathrooms 2.5
  • Acreage 3.66

Nestled in one of the oldest neighborhoods in Tisbury, this 5br architecturally designed home sits on a knoll and was thoughtfully sited to allow natural sunlight from its southern exposure in almost every room. This peaceful retreat has open pastoral views and a natural, rural setting that one can enjoy inside and out. The homes’ two-story floor plan has an open kitchen dining area with granite countertops, a pantry, and doors leading to both the screen porch and south facing deck. The living area has many windows for natural light, a fireplace and built-ins and shares a hallway to the kitchen and the den. The floor plan offers two separate bedroom wings for an expanding family, privacy for guests, or even for two families. A spacious mudroom and plenty of closet space add to the functionality of this home. There are many built-in shelves, desk, bookcases, window seat and drawers. All floors are gleaming, hardwood Ash throughout and all bathrooms have tumbled marble flooring and marble sink countertops. There’s a detached garage with arched, barn doors, a screen porch with custom Artisan doors, a deck, a roof deck and a full basement with ample head height for future, finished overflow space. Solar panels hang from the garage roof to provide a low cost energy usage. Walk out the front door and into the Ancient Ways maze of hiking trails, fields and ponds throughout the neighboring 130 acres of two scenic Land Bank properties. The land of 3.66 acres is ample enough for a future guest house and more outbuildings.

Listed by Michelle Kelly of Tea Lane Associates

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

1 North Street

Edgartown, MA1 North Street

Price$5,250,000

Est. Mortgage: $/month

Pending

MLS ID 37369

  • Residential
  • Mls Status Pending
  • Bedrooms 4
  • Bathrooms 4.5
  • Acreage 0.357

Located in a quiet neighborhood on the edge of Edgartown Village, this beautiful residence with detached guest quarters features indoor and outdoor areas that take living and entertaining to the next level. From the gourmet kitchen with fireplace and eat-in area to the formal dining room and lovely living room with fireplace, the flow is graceful and offers plenty of space. At the end of the house is a cozy wood-paneled den, also with a fireplace, and beyond is the veranda overlooking the side yard. The main house offers three bedrooms each with a private bath, including a deluxe primary suite with a balcony overlooking the grounds. The guest quarters include a solarium-like living area with a fieldstone fireplace and wet bar and a one-bedroom suite. Between the main and guest house is a bluestone courtyard with a Gunite pool, raised spa and built-in barbecue. The perfect getaway, conveniently located with easy access to Edgartown Village, beaches, the bike path and so much more!

Listed by Lesley Heidt of Sandpiper Realty

$
$
%
$/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.

Save FavoriteSchedule TourAsk A QuestionMore Details

"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."