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Vineyard Haven, MA Homes for Sale with Pool

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  • /27

    $260,000

    • 1 Bed
    • 1 Bath
    • 319 Sq Ft

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 27F, a comfortable studio offering the perfect combination of a Martha’s Vineyard getaway and rental opportunity. Accommodating up to four guests, this inviting unit features two double beds, one full bath, a convenient kitchenette, cable TV and free WiFi. Island Inn is a seasonal resort, open April through October, offering a relaxed, pet-friendly setting with a

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    33 Island Inn Rd Unit 25F, Oak Bluffs, MA 02568
  • /43

    $527,500

    • 1 Bed
    • 1.5 Baths
    • 590 Sq Ft

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568

    Welcome to Unit 38G at the Island Inn, offering resort-style living in an exceptional Oak Bluffs location just steps from the beach. This desirable ground-floor end unit features a large glass slider opening to the patio, with stairs leading to the heated outdoor pool just a few feet away. Accommodating up to six guests, the unit features one bedroom with a queen bed, a separate sleeping area

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    21 Island Inn Rd Unit 38G, Oak Bluffs, MA 02568
  • /41

    $287,500

    • 1 Bed
    • 1 Bath
    • 388 Sq Ft

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 9C, an inviting Martha’s Vineyard retreat offering the perfect combination of personal enjoyment and rental opportunity. This comfortable studio accommodates up to four guests with two double beds, a full bath, kitchenette with a 2-burner cooktop, cable TV and free WiFi. A unique opportunity is adjoining Unit 10C, a separate 1-bedroom, 1-bath suite accommodating up

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 9C, Oak Bluffs, MA 02568
  • /32

    $310,000

    • 1 Bed
    • 1 Bath
    • 419 Sq Ft

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568

    Welcome to 27 Island Inn, Unit 10C, a comfortable one-bedroom, one-bath Martha’s Vineyard retreat offering an ideal combination of personal enjoyment and rental opportunity. Accommodating up to four guests, 10C features a queen bedroom, sofa bed, cozy living area, well-equipped kitchenette. A unique feature is the adjoining door to Unit 9C, a studio with two double beds, full bath and

    Agent Photo

    Rene Ben David

    Ocean Park Realty Inc

    27 Island Inn Rd Unit 10C, Oak Bluffs, MA 02568
  • /33

    $3,600,000

    • 5 Beds
    • 3 Baths
    • 2,701 Sq Ft

    20 James Pond Way, Vineyard Haven, MA 02568

    Tucked away on 4.5 acres off Lambert's Cove Road, this unique property offers privacy and peaceful views to James Pond. A private boardwalk leads to a boathouse with direct access to James Pond, perfect for paddling across to Lambert's Cove and enjoying the nearby James Pond Preserve. The home features a spacious living room with cathedral ceilings and a wood burning fireplace, opening onto a

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
  • /26

    $1,399,000

    • 5 Beds
    • 2 Baths
    • 1,968 Sq Ft

    41 Edgartown Rd, Vineyard Haven, MA 02568

    Located on the edge of downtown Vineyard Haven, just steps from the ferry, harbor, shops, restaurants, and beaches, this two-family property presents a rare opportunity. With full-floor residences offering a combined five bedrooms, the home provides exceptional flexibility for owner occupancy with rental income, investment, employee housing, or multigenerational living. Ready for thoughtful

    Peyton Wallace Studio Realty LLC

    41 Edgartown Rd, Vineyard Haven, MA 02568
  • /15

    $725,000

    • 2 Beds
    • 1 Bath
    • 703 Sq Ft

    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568

    Vineyard Haven- Walk to the Ferry from this 2 bedroom condo with pool. Located near the downtown area a desirable place for a rental property or live there year-round. The property features common grounds, picnic tables, and seating by the pool to relax and enjoy the outdoors.

    Lisa Lucier Anchor Realty of MV

    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568
  • /19

    $5,800,000

    • 6 Beds
    • 9 Baths
    • 5,732 Sq Ft

    31 Lamberts Cove Rd, Vineyard Haven, MA 02568

    Tashmoo Farm, one of Martha’s Vineyard’s iconic properties, a take-your-breath-away landmark on Lamberts Cove Road! This country estate of over 10 acres is within close proximity of the village of Vineyard Haven with its boutiques and bourgeoning restaurant scene, and yet feels secluded and remote. For 3 centuries it has been a beloved year-round residence and at times a sought-after vacation

    Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

    31 Lamberts Cove Rd, Vineyard Haven, MA 02568
  • /42

    $3,225,000

    • 3 Beds
    • 4.5 Baths
    • 3,219 Sq Ft

    8 Woodhaven Dr, Edgartown, MA 02539

    Hidden behind a veil of privacy on a generous coastal sanctuary, an extraordinary property waits to be discovered. This custom masterpiece blends timeless architecture with a modern, elusive sophistication, offering comfortable finished living space within an impressive total structure. Cross the threshold onto rich hardwood floors where light dances beneath a dramatic cathedral ceiling, drawing

    Jennifer B. DaSilva Compass

    8 Woodhaven Dr, Edgartown, MA 02539
  • /18

    $239,000

    • 1 Bed
    • 1 Bath
    • 316 Sq Ft

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568

    Want to own a slice of Martha's Vineyard? As an owner of this studio style "Condo-tel", you will enjoy the convenience of worry free ownership. This unit has newer flooring, an updated bathroom, updated kitchenette and a cathedral ceiling. This is casual resort style living that includes association pool, 3 tennis courts, playground, and shared grilling area. This wonderful location borders Farm

    Rene Jackson Island Real Estate

    33 Island Inn Rd Unit F 22, Oak Bluffs, MA 02568
  • /24

    $429,000

    • 1 Bed
    • 1 Bath
    • 305 Sq Ft

    124 Skiff Ave Unit B-12, Vineyard Haven, MA 02568

    Welcome to Unit B-12 at the Causeway Condominiums, a turnkey studio offering comfortable, low-maintenance island living just a short walk to the charming village of Vineyard Haven. Thoughtfully designed to maximize space and functionality, this inviting residence features warm bamboo flooring throughout, a custom Murphy bed, and a beautifully crafted custom mahogany closet and storage system,

    Marilyn Moses Ocean Park Realty Inc

    124 Skiff Ave Unit B-12, Vineyard Haven, MA 02568
  • /32

    $1,595,000

    • 3 Beds
    • 3.5 Baths
    • 2,739 Sq Ft

    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557

    Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

    Rose Ryley Wallace & Co. Sotheby's International Realty

    40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
  • /18

    $250,000

    • 1 Bed
    • 1 Bath
    • 331 Sq Ft

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568

    Island Inn ....tucked behind the ever-popular Noman's Restaurant. Located off the Beach Road in Oak Bluffs. Fully furnished and updated 2nd floor studio. New: floors, appliances, television, mini-split AC and two double mattresses, Fully furnished galley kitchen. Use the convenient bike path to State Beach and then further on into Edgartown ...OR a short distance north to Oak Bluffs center, ferry

    Patti Dean Wiggy's Pond Real Estate

    27 Island Inn Rd Unit D17, Oak Bluffs, MA 02568
  • /31

    $2,200,000

    • 4 Beds
    • 3 Baths
    • 3,771 Sq Ft

    99 Oak Ln, Vineyard Haven, MA 02568

    This enchanting artist-designed property is tucked away on 2.9 private acres in West Tisbury, a thoughtfully composed retreat with pastoral meadows, mature landscaping, and an unmistakable sense of intention and sophisticated taste. The two-bedroom, two-bathroom Main House is complemented by a spacious two-bedroom, one-bathroom Guest Studio with a fireplace, offering a combined 3,771 square feet

    Rose Ryley Wallace & Co. Sotheby's International Realty

    99 Oak Ln, Vineyard Haven, MA 02568
  • /67

    $4,125,000

    Open Sat 10:30AM - 12:30PM
    • 7 Beds
    • 4.5 Baths
    • 3,313 Sq Ft

    31 Josiah Sachem Way, Vineyard Haven, MA 02568

    An Inspirational Oasis -- Nestled along the gentle slopes of Indian Hill, this secluded three-dwelling compound offers more than three acres of exceptional privacy where rural tranquility meets effortless island living. Centered around a heated saltwater pool, the main house, studio barn, and guest house provide 4,464 square feet of living space surrounded by wildflower meadows, perennial

    Peyton Wallace Studio Realty LLC

    31 Josiah Sachem Way, Vineyard Haven, MA 02568
  • /42

    $5,450,000

    • 4 Beds
    • 5.5 Baths
    • 3,300 Sq Ft

    8 Paddock Rd, Oak Bluffs, MA 02557

    Refined Vineyard living in The Preserve. Set on a knoll overlooking the pond and sweeping grasslands, this exceptional home blends classic coastal architecture with modern luxury. The expansive great room showcases cathedral ceilings, rich millwork, and abundant natural light, with three sets of French doors opening to a bluestone patio with multiple sitting areas and a heated saltwater pool. The

    Lesley Heidt Sandpiper Realty, Inc.

    8 Paddock Rd, Oak Bluffs, MA 02557
  • /28

    $550,000

    $49K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568

    JUST COMPLETED ~ fully renovated exterior including a new roof, siding, shutters, trim, all new windows, doors, stairways, and decks. Outstanding move-in-ready, year-round two-bedroom ground-level condo with dedicated parking in an ideal Vineyard Haven location close to the ferry, Main Street shops, and restaurants. The beautifully maintained common grounds feature colorful landscaping, picnic

    Stephanie Roache Donnelly + Co.

    124 Skiff Ave Unit A-11, Vineyard Haven, MA 02568
  • /17

    $725,000

    • 2 Beds
    • 1 Bath
    • 703 Sq Ft

    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568

    Vineyard Haven- Walk to the Ferry from this 2 bedroom condo with pool. Located near the downtown area a desirable place for a rental property or live there year-round. The property features common grounds, picnic tables, and seating by the pool to relax and enjoy the outdoors.

    Lisa Lucier Anchor Realty of Martha's Vineyard

    124 Skiff Ave Unit G-11, Vineyard Haven, MA 02568
  • /37

    $389,900

    • 1 Bed
    • 1.5 Baths
    • 584 Sq Ft

    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568

    HERE'S YOUR CHANCE TO OWN A PIECE of the ISLAND!!! Live the beautiful Island Life with this gorgeous seasonal condo at the Island Inn Resort. AFFORDABLE & PRICED APPROX $100,000 less than an identical unit that Just Sold this summer!!Don't miss this delightful one and a half bedroom seasonal condo (sleeps 6) available for your families use. When you’re not here, the management team will rent

    Susan Austin Austin R.E. Properties of MV

    21 Island Inn Rd Unit 35, Oak Bluffs, MA 02568
  • /31

    $1,250,000

    • 3 Beds
    • 3 Baths
    • 1,682 Sq Ft

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    END UNIT WITH PRIVATE DRIVEWAY IN TASHMOO WOODS. Well-maintained 3BR/3BA condo offering rare privacy, space, and a single-family feel in one of Vineyard Haven’s most desirable communities. End unit with private driveway, one-car garage, and extra storage. Mature plantings, including 24 added trees, enhance the setting. Open layout with granite kitchen and high-end appliances flows to dining area

    Jennifer O'hanlon Compass

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
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