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308 South Road, Chilmark
$6,500,000
4 Beds ⋅ 5 Baths ⋅ 73478310 MLS
Waterfront South Shore Retreat with Private Dock and Water Views. Set on the edge of Chilmark Pond, this exceptional waterfront residence offers rare privacy, refined design, generous water views and easy pond access. Thoughtfully renovated in 2018, the home blends contemporary sophistication with the beauty of its natural environment. A private dock on the property provides direct pond access. The beautifully manicured path, leads from the house to the dock, where you can launch across the pond to your own private South Shore beach lot, included in this sale. Of course the new owner also has access to iconic Lucy Vincent and Squibnocket beaches. The property is surrounded by over seven acres of abutting conservation land. The grounds are meticulously designed, with mature landscaping and gardens that feel both timeless and intentional. This is more than a residence. It's the key to embracing the Chilmark lifestyle defined by privacy, water access, and understated elegance.

308 South Road, Chilmark

Listing courtesy of Listing Agent: Rose Ryley from Listing Office: Wallace & Co. Sotheby's International Realty.
63 Putnam Rd, Chilmark
$4,850,000
3 Beds ⋅ 3 Baths ⋅ 73540991 MLS
Stylish Chilmark retreat with sweeping water views, private beach, tennis, and walking trails. Set within the coveted Spring Point community, this beautifully renovated island home captures a rare sense of place, with natural beauty, privacy, and effortless indoor-outdoor living. Thoughtfully updated in 2022, the home blends relaxed coastal sophistication with driftwood-colored hardwood floors, a striking stone fireplace, sleek cook’s kitchen, custom-tiled baths, and Sonos® sound. Large windows and sliding glass doors frame water views and open to private decks, while a spacious screened porch is ideal for morning coffee, summer dining, or entertaining. Landscaped grounds, a paver parking court, charming gazebo, and finished walk-out lower level add comfort and flexibility. Spring Point amenities include 68 acres of common land, ancient walking trails, two tennis courts, and Beck’s Beach, a private shoreline with magnificent sunsets from the Elizabeth Islands to Gay Head Lighthouse.

63 Putnam Rd, Chilmark

Listing courtesy of Listing Agent: Wendy Harman from Listing Office: Compass.
205 South Rd, Chilmark
$4,550,000
4 Beds ⋅ 5 Baths ⋅ 73495595 MLS
CLASSIC CHILMARK RETREAT. Set on nearly six acres of picturesque land, this beautifully restored and expanded modern farmhouse offers a seamless blend of timeless Vineyard character and contemporary comfort. The 3-bedroom, 3.5-bath main residence spans approximately 5,400 square feet of thoughtfully designed living space, highlighted by a sun-filled open kitchen and living area anchored by a striking central fireplace—ideal for both everyday living and entertaining. An expansive primary suite wing features a spacious bedroom, full bath, private office, half bath, and dedicated laundry. The second floor offers flexible space for a studio, office, or media room, while a classic three-season room invites relaxed enjoyment of the surrounding landscape and distant winter water views. Perfect for compound living, the property includes a guest house, solar, horse barn, fenced pasture, garage, and historic boat shed. Deeded access to Chilmark Pond and South Shore Beach completes this property.

205 South Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..
15 Old Farm Rd, Chilmark
$3,710,000
3 Beds ⋅ 6 Baths ⋅ 73418123 MLS
CHILMARK BLISS – Refined Retreat | 15 Old Farm Road. Set on 3+ acres of manicured grounds, this 2020 Peter Breese–redesigned home blends elegance and tranquility. A serene pond, stream, and custom hardscape set the tone. Inside, a dramatic open kitchen/living area boasts high-end appliances, stone countertops, and a striking fireplace, with a pantry leading to a screened porch. The main-level primary suite opens to a private deck; also on this floor are a library and media room. Upstairs offers a guest room and bath plus a separate suite with fireplace, lounge, and patio. The lower level features storage, a bonus room, and a walk-out to gardens, fenced flower beds, and a post-and-beam artist studio. Designed for a future pool with a 5-bedroom septic. Includes access to Lucy Vincent & Squibnocket beaches.

15 Old Farm Rd, Chilmark

Listing courtesy of Listing Agent: Tina Miller from Listing Office: Donnelly + Co..
300 North Rd/18 Belhaven Way, Chilmark
$2,800,000
4 Beds ⋅ 4 Baths ⋅ 73533644 MLS
Tucked away on 4.4 spectacular acres just off North Road, this one-of-a-kind Chilmark retreat blends timeless Vineyard charm with exceptional privacy. A shaded driveway leads to classic stone walls and cedar gates opening into a beautifully landscaped courtyard. The inviting porch overlooks lush gardens, creating a peaceful outdoor sanctuary. Inside, warm, light-filled living spaces and the primary suite enjoy sweeping meadow views framed by granite boulders and stately oaks. The main level offers additional sleeping accommodations, while a spacious finished lower level with a private entrance provides ideal guest quarters. Across the courtyard, an unfinished outbuilding with a screened porch offers exciting potential as a bunkhouse, studio, or office. Two garage bays accommodate cars or boats. Ideally located less than 2 miles from Menemsha Village and Beach, 1 mile from Great Rock Bight, and just 3 miles from Lucy Vincent Beach.

300 North Rd/18 Belhaven Way, Chilmark

Listing courtesy of Listing Agent: Bonnie Pierce from Listing Office: Wallace & Co. Sotheby's International Realty.

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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