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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82 Edgartown- Vineyard Haven Road Vineyard Haven MA 02568

MLS Number 39770

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 2
  • Acreage 0.1949

Walk to downtown Vineyard Haven, the ferry, MV Museum and Veterans Park from this lovely older home with tons of character. Some of the original molding, doors and doorknobs still remain. Beautiful pine hardwood floors with wood pegs through out the first floor and yellow pine nailed slat floors upstairs. With a total of 5 bedrooms and 2 full baths, the main house can accommodate a large family. House does need updating. Property is being sold "AS IS". OPPORTUNITY TO ACQUIRE ABUTTING PARCEL WITH GUEST HOUSE FOR $800,000. 90 Edgartown- Vineyard Haven Road.

Listed by Julianna Flanders of Flanders Real Estate

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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69 Whalers Walk Edgartown MA 02549

Edgartown, MA69 Whalers Walk

Price$2,350,000

Est. Mortgage: $/month

MLS Number 38383

  • Residential
  • Mls Status Active
  • Bedrooms 3
  • Bathroom 2.5
  • Acreage 0.912

EDGARTOWN - Beautifully landscaped property, on a lovely open, cleared lot, with fabulous curb appeal, only minutes to Downtown Edgartown and South Beach. Currently a three bedroom, 2.5 bath home, with multiple living spaces, this property can be expanded to SEVEN (7) bedrooms with connection to Town Sewer. With an abundance of existing living/entertaining space, the huge main living room, large enough to accommodate a separate dining area, has sliders opening to a 52ft. long deck that is perfectly perched to sit and watch over a seemingly unending, park-like, back yard - perfect for entertaining! Along with a casual eat-in kitchen, with slider to huge deck, there’s an additional formal dining room, also with a slider to the deck and a formal living room on the ground floor. In hallway on the way Upstairs is a powder room. Upstairs, there are three bedrooms, including a very charming Primary Suite with private bathroom and custom details. There are also two guest bedrooms, a guest bathroom and a third very large living room. This house has so many possibilities, leave it as is, or add additional bedrooms within the existing structure, the layout is already in place! This home is ideally sited on the lot to accommodate a 900sq.ft. Guest House, leaving plenty of room for a Swimming Pool and plenty of parking already in place. Seller completed a number of updates in 2018 including the addition of Central Air, a Navien On Demand hot water system, multiple exterior improvements, including but not limited to, a new cobblestone lined driveway and apron with plenty of parking. Hardwood floors on each level. Full basement has its own heat and a separate workshop with a walk out to back yard. Sale will occur only as part of a simultaneous closing.

Listed by Alisan Lohan-Conway of Alisan Lohan-Conway Properties

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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82 & 90 Edgartown- Vineyard Haven Road Vineyard Haven MA 02568

MLS Number 39582

  • Residential
  • Mls Status Active
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.195

Walk to downtown Vineyard Haven, the ferry, MV Museum and Veterans Park from this lovely older home with tons of character. Some of the original molding and doors and doorknobs still remain. Beautiful pine hardwood floors with wood pegs through out the first floor and yellow pine nailed slat floors upstairs. With a total of 5 bedrooms and 2 full baths the main house can accommodate a large family. House does need updating. The small second house provides rental income and has expansion potential. Property is being sold "AS IS." **Showings starting Monday June 6th. Tenant in guest house until 6/30. Will require 24 hour notice to view.**

Listed by Julianna Flanders of Flanders Real Estate

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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9 Peases Point Road Edgartown MA 02539

Edgartown, MA9 Peases Point Road

Price$6,495,000

Est. Mortgage: $/month

MLS Number 39573

  • Residential
  • Mls Status Active
  • Bedrooms 5
  • Bathroom 5
  • Acreage 0.75

Stunning Edgartown home in a premier location with a guest house and new salt-water pool. Every aspect of the fully renovated main house reflects exquisite high-end detail. The updated, bright interior combines refined elegance with casual coastal living. When you enter you are greeted with an open concept living room, dining room and kitchen. The fabulous, gourmet kitchen offers custom cabinetry, professional grade appliances, a large island, and a sun-filled breakfast nook with easy access to an inviting outdoor deck. The second floor features a spacious primary bedroom with an en-suite spa-like bathroom. Two more guest bedrooms and a full bath complete the 2nd floor. Venture up to the 3rd level where you will find a large media room with additional sleeping areas all with distant views of Edgartown Harbor. A true family vacation retreat, this property includes a guest house that features a covered front porch, open living room, kitchen, 2 guest bedrooms and a full bath with a claw-foot tub. The guest house is privately sited on this manicured .75 acre lot with its own outdoor spaces, covered side porch and outdoor shower. This exceptional Martha’s Vineyard retreat also features a heated 14 x 30 saltwater pool and a 2-car garage with attic space above just waiting to be finished. The ultimate island get-away offering unmatched privacy and easy access to Downtown Edgartown, South Beach, the bike path, and the Katama General Store.

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

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$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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72 Chappaquiddick Avenue Edgartown MA 02539

Edgartown, MA72 Chappaquiddick Avenue

Price$4,200,000

Est. Mortgage: $/month

MLS Number 39511

  • Residential
  • Mls Status Active
  • Bedrooms 8
  • Bathroom 7.5
  • Acreage 3

WELCOME to this turn-key CHAPPY COMPOUND! This property offers it ALL, with its Six (6) Bedroom, Five (5) bath Primary Home, Two (2) bedroom, Two (2) bath GUEST HOUSE, expansive POOL HOUSE with a bath, kitchenette, large lounge area topped with a cathedral ceiling, a YOGA BARN, a POOL, a VOLLEY BALL COURT and a TENNIS COURT with a BASKETBALL COURT, all set upon three acres of private, expansive land with distant WATER VIEWS! The estate is spectacularly located on Sampson Hill, being the highest elevation on Chappaquiddick. The location is convenient to the Chappy ferry, the Chappy Community Center, Slip Away Farm, the hiking trails on Land Bank properties and the beaches. A true gem of a location! This Chappy Compound has been meticulously grown and maintained over the years through architectural design, professional decorating and professional landscaping. The Yoga Barn was recently constructed in 2022. It has a light airy feeling with its cathedral ceiling, light colored wood and abundance of natural light streaming into its interior space. An interior barn door separates the space into two work out areas. The architecturally designed Guest House was constructed in 2018 with year round living as an option. It was designed with an open floor plan and an abundance of outdoor living spaces to make this Guest House live large. The fun Pool House sports a wooden beamed cathedral ceiling with a large open lounge area, kitchenette and bath, overlooking the Pool and Yoga Barn. The interplay between the Yoga Barn, Pool House, Pool and abutting Tennis Court makes this Chappy Compound fun and playful!

Listed by Michele Casavant of Vineyard Village Realty

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$
%
$/month over payments
Federal 30-year interest rate: 5.7% last updated on Jun 30, 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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"Based on information submitted to MA_LINKMV as of July 1, 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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