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Marthas Vineyard, MA Homes for Sale with Pool

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  • /41

    $9,495,000

    • 4 Beds
    • 6 Baths
    • 4,605 Sq Ft

    29 Slough Cove Rd, Edgartown, MA 02539

    LUXURIOUS COUNTRY ESTATE IN KATAMA. Sited at the end of a long private drive, amid a bucolic 1.5-acre meadow setting with stone retaining walls and lush perennial gardens, this elegant country estate, designed by noted architect Patrick Ahearn, offers the epitome of luxurious living in Katama. The home’s timeless and charming character is highlighted by thoughtful, top-notch architectural details

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    29 Slough Cove Rd, Edgartown, MA 02539
  • /42

    $5,995,000 Open Sun 1:30PM - 3:30PM

    • 3 Beds
    • 6 Baths
    • 3,608 Sq Ft

    385 Barnes Rd, Vineyard Haven, MA 02568

    Indulge in luxurious living at this exquisite waterfront retreat featuring a private 125-foot sandy beach. Over 5,400 sq ft on three floors blend elegance with indoor-outdoor living. The grand foyer leads to dramatic interiors with high ceilings and floor-to-ceiling windows showcasing stunning water views. Highlights include a striking stone fireplace, custom built-ins, gourmet kitchen with stone

    Agent Photo

    Wendy Harman

    Compass

    (508) 274-5363

    385 Barnes Rd, Vineyard Haven, MA 02568
  • /38

    $9,250,000

    • 6 Beds
    • 8 Baths
    • 6,881 Sq Ft

    52 Fuller St, Edgartown, MA 02539

    Located on prestigious Fuller Street, half a block from Fuller Street Beach lies this classically styled home. The home features anamazing family room/kitchen with an abundance of retractable glass doors facing the pool area and 2 fireplaces. There is a dining room, office, den and ground floor bedroom with private bath. The second-floor features two large en suite guest rooms and acathedral

    Gerret Conover LandVest MV

    52 Fuller St, Edgartown, MA 02539
  • /37

    $6,250,000

    • 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
  • /51

    $9,995,000

    • 4 Beds
    • 7 Baths
    • 5,458 Sq Ft

    43 Peases Point Way S, Edgartown, MA 02539

    Refined, timeless, and unparalleled, 43 Peases Point Way South effortlessly blends warmth, elegance, and sophistication to create a truly distinctive living experience in one of Edgartown's most coveted locations. Designed by celebrated architect Patrick Ahearn, this exceptional residence is just a short stroll from historic Main Street. From the gated arbor entry and tranquil courtyard to the

    Katherine Donahue Sandpiper Realty Inc

    43 Peases Point Way S, Edgartown, MA 02539
  • /35

    $6,000,000

    • 5 Beds
    • 7 Baths
    • 5,956 Sq Ft

    10 Puwal Ln, Edgartown, MA 02539

    KATAMA COMPOUND WITH POOL - TURNKEY. In an enclave of luxury homes in Katama, this newly-built 5 bedroom, 5 bathroom property with three half-baths is being delivered turnkey with fine furnishings and artwork. The home has everything the modern buyer wants, including two primary bedroom suites (one upstairs, one downstairs), all bedrooms with ensuite bathrooms, two laundry rooms, detached guest

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    10 Puwal Ln, Edgartown, MA 02539
  • /39

    $4,590,000

    • 3 Beds
    • 2.5 Baths
    • 1,870 Sq Ft

    4 Down Harbor Rd, Edgartown, MA 02539

    Coveted Down Harbor! This 3-bedroom 2-bath home sits in the Down Harbor association in a prime Katama location. This charming home is an entertainer's delight with a spacious yard, a large deck, an outdoor kitchen, pool, and recently built pool house with 2 outdoor showers, 1/2 bath and a storage shed. This home features vaulted ceilings, exposed beams, and a bright kitchen with a breakfast bar

    Cheri Mason LandVest MV

    4 Down Harbor Rd, Edgartown, MA 02539
  • /26

    $9,750,000

    • 5 Beds
    • 5 Baths
    • 3,550 Sq Ft

    1 Field Club Dr, Edgartown, MA 02539

    Nestled in the prestigious Field Club, this extraordinary five-bedroom compound epitomizes luxurious island living. This residence exudes timeless elegance and modern sophistication. Upon entering, the foyer sets the tone with a warm and inviting glow. The main level boasts an open-concept layout, featuring a gourmet chef's kitchen adorned with top-of-the-line appliances, granite countertops, and

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    1 Field Club Dr, Edgartown, MA 02539
  • /2

    $10,850,000

    • 7 Beds
    • 8 Baths
    • 12,051 Sq Ft

    14 Trapps Pond Rd, Edgartown, MA 02539

    Located on nearly 2-acres in the exclusive and newly created Trapps Pond Preserve, is this grand luxuriously appointed home. Thisis one of four homes being built and will be the first to be completed. Every room in the house is on a scale not often afforded in aVineyard home, with 10 ft coffered ceilings and open/flowing floor plan. There is an abundance of light streaming in from theoversized

    Gerret Conover LandVest MV

    14 Trapps Pond Rd, Edgartown, MA 02539
  • /8

    $875,000

    • 3 Beds
    • 2 Baths
    • 1,356 Sq Ft

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568

    Bright first-floor, three-bedroom, two bath condo in the popular Vineyard Haven Causeway Harborview association. Easy access to downtown shops, restaurants, harbor, ferry, and beaches. Building amenities include a shared pool, convenient storage, and on-site laundry facilities. The perfect blend of convenience and comfort for year-round living or as your ideal summer retreat.

    Emma Kennedy Sandpiper Realty Inc

    124 Skiff Ave Unit D-10, Vineyard Haven, MA 02568
  • /34

    $2,995,000

    • 3 Beds
    • 2.5 Baths
    • 1,964 Sq Ft

    21 Kitts Field Cir, Edgartown, MA 02539

    Tastefully renovated, stylishly decorated with the beach in mind, superbly maintained and thoughtfully expanded - all these attributes and more apply. The list of improvements is long and, yet the property has not reached its maximum potential. It is connected to town sewer and is allowed up to 6 bedrooms. It is a conforming lot according to town zoning, which allows for greater flexibility.

    Lynn Buder Sandpiper Realty Inc

    21 Kitts Field Cir, Edgartown, MA 02539
  • /40

    $2,590,000

    • 4 Beds
    • 3.5 Baths
    • 3,052 Sq Ft

    27 Watcha Path, Edgartown, MA 02539

    STYLISH VINEYARD LIVING WITH EXCEPTIONAL OUTDOOR AMENITIES. This beautifully landscaped coastal-style home is set on three acres just off the bike path, offering easy access to all Island towns. A heated saltwater pool, expansive decking, and outdoor gathering spaces create the perfect setup for Vineyard summers. The home offers 4 bedrooms and 3.5 baths, including two primary suites—one on each

    Jennifer O'hanlon Compass

    27 Watcha Path, Edgartown, MA 02539
  • /21

    $650,000

    • 2 Beds
    • 1 Bath
    • 725 Sq Ft

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

    Outstanding year-round, two-bedroom condo on the ground level with dedicated parking, and close to the ferry, shops, and restaurants on Main Street, Vineyard Haven. The common grounds feature colorful landscaping, picnic tables, grills, and a swimming pool with a distant peek at the Lagoon. This unit has been delightfully renovated, featuring new hardwood floors, an updated bathroom, updated

    Stephanie Roache Donnelly + Co.

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

    $4,250,000

    • 5 Beds
    • 5.5 Baths
    • 2,205 Sq Ft

    11 Bernard Way, Edgartown, MA 02539

    To be built by a luxury home builder! Located at the end of a quiet cul de sac, just half a mile to the top of Main Street, this Coastal Contemporary-styled home can be completed by July of 2026. Please review the digital renderings which show the vision for this high-end 5-bedroom home, swimming pool and guest house/pool house. High-end details include all ensuite bedrooms in the main house,

    Mark Jenkins Wallace & Co. Sotheby's International Realty

    11 Bernard Way, Edgartown, MA 02539
  • /41

    $2,200,000

    • 3 Beds
    • 2.5 Baths
    • 2,526 Sq Ft

    56 Bridle Path Rd, Vineyard Haven, MA 02568

    POOL AND LUSH GARDENS Situated on three acres, abutting nearly 25 acres of conservation land, this well-crafted home offers the ideal blend of tranquility and convenience. Step inside to discover over 2,500 square feet of thoughtfully designed living space. The bright and inviting living room, complete with a cozy fireplace, opens onto the kitchen and dining area. Head out to a comfortable

    Tina Miller Compass

    56 Bridle Path Rd, Vineyard Haven, MA 02568
  • /33

    $3,995,000

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

    20 James Pond Way, Vineyard Haven, MA 02568

    Nestled on a serene 4.5-acre parcel of land off Lambert's Cove Road, this exquisite property offers unparalleled privacy, views and direct access to James Pond and beyond to the Land Bank's Lambert's Cove Beach property. In addition to the custom heated Gunite pool, the expansive yard provides space for many outdoor activities while relishing the tranquility of the location. The residence

    Sheila Morse Island Real Estate

    20 James Pond Way, Vineyard Haven, MA 02568
  • /27

    $1,925,000

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    212 Charles Neck Way, Vineyard Haven, MA 02568

    This beautifully renovated contemporary South Shore retreat, located in a tranquil setting, features 3 bedrooms, two and 2 1/2 bathrooms, central air, all new appliances, in ground pool and mature perennial gardens galore! Sitting on 1.5 acres, this location provides easy access to Long Point Beach and the Red Pony Farm equestrian center and, includes access to the coveted Lamberts Cove Beach on

    Perry Patterson MV Luxury Homes, LLC

    212 Charles Neck Way, Vineyard Haven, MA 02568
  • /39

    $3,649,000

    • 5 Beds
    • 4.5 Baths
    • 4,218 Sq Ft

    7 Whistling Swan Cir, Edgartown, MA 02539

    Located in the sought-after Island Grove neighborhood, this Edgartown home is near Morning Glory Farm, Downtown, and South Beach. Designed for entertaining, the first floor features a custom kitchen, dining and living rooms, den, screened porch, half bath, and a seamless flow to outdoor living and a new heated pool. A spacious first-floor primary suite includes a walk-in closet and full bath.

    Jarrett Hurwitz Keller Williams Realty

    7 Whistling Swan Cir, Edgartown, MA 02539
  • /24

    $3,495,000

    • 4 Beds
    • 6 Baths
    • 3,793 Sq Ft

    28 Crocker Dr, Edgartown, MA 02539

    This beautifully renovated Katama retreat blends refined design, luxury amenities, and flexible living. The main house offers three bedrooms, including a peaceful primary suite with private deck, a second en suite, and a cozy bunkroom. The octagonal living room, skylit dining room with gas fireplace, and chef’s kitchen with quartz counters and high-end appliances are perfect for entertaining.

    Jennifer O'hanlon Compass

    28 Crocker Dr, Edgartown, MA 02539
  • /37

    $3,300,000

    • 5 Beds
    • 4.5 Baths
    • 4,115 Sq Ft

    357 W Tisbury Rd, Edgartown, MA 02539

    Here is the Edgartown compound you've been waiting for - a 5-bedroom main house, 2-bedroom guest house, and elevated swimming pool area located on 1.5 acres. Next door there is 25 acres of conservation land. The property is barely 2/10s of a mile to Morning Glory Farm, and just a mile and a half to the village on the bike path. The house combines island country charm with modern amenities - honey

    Bonnie Pierce Wallace & Co. Sotheby's International Realty

    357 W Tisbury Rd, Edgartown, MA 02539
  • /40

    $3,400,000

    • 4 Beds
    • 3.5 Baths
    • 4,372 Sq Ft

    110 5th St N, Edgartown, MA 02539

    Water views with a pool! This chic contemporary 4-bedroom home with a pool and 2-car garage enjoys the ever-changing water views of Sengekontacket Pond and Nantucket Sound on three levels. Fully renovated, this delightful home, being sold turnkey, marries a timeless Vineyard vibe with modern luxury. The mudroom entryway opens to the kitchen with a breakfast island, dining room, and living room

    Stephanie Roache Donnelly + Co.

    110 5th St N, Edgartown, MA 02539
  • /37

    $1,295,000

    • 3 Beds
    • 3 Baths
    • 1,628 Sq Ft

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568

    Welcome to this meticulously maintained 2+ bedroom, 3 bathroom end unit condo in Tashmoo Woods, built in 1998. The updated kitchen with granite countertops and high-end appliances opens to a dining room with a private deck overlooking lush woods. The first floor includes a den and a renovated bathroom. Upstairs, both bedrooms have ensuite bathrooms. Upgrades include propane heat, central air, a

    Jennifer O'hanlon Compass

    261 Sandpiper Ln Unit 12, Vineyard Haven, MA 02568
  • /42

    $19,900,000

    • 8 Beds
    • 7.5 Baths
    • 6,041 Sq Ft

    114 N Water St, Edgartown, MA 02539

    The property is currently rented; showings require a minimum of 48 hours’ notice. Move-In Ready – CONSTRUCTION COMPLETE - This stunning 8-bedroom, 7.5-bath generational home, completed in 2025, is fully furnished and move-in ready. The property features a 6-bedroom, 5.5-bath main residence, a 1-bedroom, 1-bath guest house with its own kitchen, and a 2-car carriage house with 1-bedroom living

    Erin Hegarty Compass

    114 N Water St, Edgartown, MA 02539
  • /32

    $3,145,000

    • 4 Beds
    • 3 Baths
    • 2,770 Sq Ft

    36 Tashmoo Ave, Vineyard Haven, MA 02568

    This beautifully renovated gambrel-style home in Vineyard Haven seamlessly blends classic charm with modern luxury. This pristine residence is nestled within a private, hedge-lined yard in one of Vineyard Haven's most quiet and quaint neighborhoods. With the new heated salt-water pool, outdoor shower, lovely plantings, and beautiful gardens, no detail has been overlooked. The property also

    Alyssa Halisky Wallace & Co. Sotheby's International Realty

    36 Tashmoo Ave, Vineyard Haven, MA 02568
  • /18

    $15,950,000

    • 6 Beds
    • 9 Baths
    • 1,320 Sq Ft

    68 N Water St, Edgartown, MA 02539

    This expansive historic compound in the heart of Edgartown village offers the perfect blend of old-world charm and modern luxury.Just steps away from Edgartown's finest restaurants and shops, this stunning property has been completely renovated by SternMcCafferty Architecture + Interiors, showcasing a harmonious balance of contemporary design and traditional architectural details.Upon entering,

    Thomas Wallace Wallace & Co. Sotheby's International Realty

    68 N Water St, Edgartown, MA 02539
  • /2

    $1,795,000

    • 2 Beds
    • 3 Baths
    • 1,737 Sq Ft

    150 Cove Rd Unit 10, Vineyard Haven, MA 02568

    The Premiere Townhouse at Tashmoo Wood. Elegantly renovated, this sun-filled end unit is fresh and modern with finish details. From the moment you step onto the expanded wrap-around deck, you will begin to see the fine craftsmanship of the property. Walk through the front entry and you will gain further appreciation for the meticulous attention to detail. Expansive windows fill the living area

    Michele Moore Island Real Estate

    150 Cove Rd Unit 10, Vineyard Haven, MA 02568
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