Chilmark Homes

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  /29

  $10,950,000

  • 4 Beds
  • 3.5 Baths
  • 2,050 Sq Ft

  16 Shotnaigher Ln, Chilmark, MA 02535

  New to market this completely renovated water view home is located in a private enclave of upscale homes fronting on Squibnocket Pond in Chilmark. There are 360 degree views from this 3.6 acre hilltop site offering views of the pond, Atlantic Ocean and north to Menemsha Pond and the Vineyard Sound. Sunrise and Sunset! This home, completely renovated in 2022 features a state of the art gourmet

  Rebecca V Conroy Conroy & Company R.E., Inc.

  16 Shotnaigher Ln, Chilmark, MA 02535
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  /32

  $42,000 Per Month

  • 5 Beds
  • 2.5 Baths
  • 3,000 Sq Ft
  • House for Rent

  19 Lake Rd, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms,

  Karen Overtoom Karen M. Overtoom R.E.

  19 Lake Rd, Chilmark, MA 02535
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  /22

  $1,607,000 Sold Jul 10, 2025

  10 N Abels Hill Rd, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft
  • Built 1978

  Last Sold Summary

  • 39% Below List Price
  • $564/SF
  • 354 Days On Market

  Current Estimated Value $1,993,418

  Last Listing Agent Elissa Lash Tea Lane Associates

  10 N Abels Hill Rd, Chilmark, MA 02535
• 

  

  /2

  Est $3,750,196 Not Listed For Sale

  1 Pond Mark, Chilmark, MA 02535

  • 3 Beds
  • 3 Baths
  • 1,316 Sq Ft
  • Built 1955

  1 Pond Mark, Chilmark, MA 02535

  Last Sold Summary

  • 5% Below List Price
  • $3,002/SF

  • Last Sold Price $3,950,000

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's
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  /40

  $1,895,000

  • 4 Beds
  • 3.5 Baths
  • 2,061 Sq Ft

  174 Middle Rd, Chilmark, MA 02535

  Nestled in the heart of Chilmark, this four-bedroom home offers a blend of comfort, convenience, and timeless Vineyard charm. Thoughtfully designed with distinct, well-proportioned rooms, the home centers around an expansive, sunlit, eat-in kitchen featuring dual ovens, elegant granite countertops, and extensive custom cherry wood built-ins that combine beauty and practicality. The welcoming

  Sheila Morse Island Real Estate

  174 Middle Rd, Chilmark, MA 02535
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  /35

  $22,000 Per Month

  • 4 Beds
  • 2 Baths
  • 2,290 Sq Ft
  • House for Rent

  36 Henry Hough Lane Ch206, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

  Karen Overtoom Karen M. Overtoom R.E.

  36 Henry Hough Lane Ch206, Chilmark, MA 02535
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  /44

  $8,178,500 Sold Oct 27, 2025

  94 Menemsha Inn Rd, Chilmark, MA 02535

  • 6 Beds
  • 4.5 Baths
  • 4,104 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $1,993/SF
  • 38 Days On Market

  Last Listing Agent Julianna Flanders Flanders Real Estate

  94 Menemsha Inn Rd, Chilmark, MA 02535
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  /12

  Est $2,495,155 Not Listed For Sale

  5 Ocean View Farm Rd, Chilmark, MA 02535

  • 3 Beds
  • 1.5 Baths
  • 1,342 Sq Ft
  • Built 1971

  5 Ocean View Farm Rd, Chilmark, MA 02535

  Last Sold Summary

  • 4% Above List Price
  • $1,796/SF
  • 3 Days On Market

  • Last Sold Price $2,410,000
  • Aug 02, 2023

  Last Listing Agent Russell Maloney Russell Maloney Real Estate
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  /23

  $1,550,000

  • 5 Beds
  • 5 Baths
  • 2,266 Sq Ft

  345 North Rd, Chilmark, MA 02535

  This versatile Chilmark property offers a rare combination of privacy, flexibility, and investment potential. The main residence features 4 bedrooms and 4 bathrooms, complemented by a detached 1-bedroom, 1-bath suite with an attached garage—ideal for guests, extended family, or rental income. Two separate parking areas provide ample space and convenience. Abutting over 200 acres of protected

  Jessica Campbell Flanders Real Estate

  345 North Rd, Chilmark, MA 02535
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  /39

  $110,000 Per Month

  • 5 Beds
  • 5 Baths
  • 4,000 Sq Ft
  • House for Rent

  17 Round Pond Rd Ch240, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

  Karen Overtoom Karen M. Overtoom R.E.

  17 Round Pond Rd Ch240, Chilmark, MA 02535
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  /10

  $10,500,000 Sold Mar 12, 2026

  51 Squibnocket Farm Rd, Chilmark, MA 02535

  • 4 Beds
  • 2.5 Baths
  • 3,200 Sq Ft
  • Built 1981

  Last Sold Summary

  • 9% Below List Price
  • $3,281/SF

  Current Estimated Value $7,955,399

  Last Listing Agent Mark Jenkins Wallace & Co. Sotheby's

  51 Squibnocket Farm Rd, Chilmark, MA 02535
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  /2

  Est $2,802,968 Not Listed For Sale

  27 Ocean View Farm Rd, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 2,450 Sq Ft
  • Built 1964

  27 Ocean View Farm Rd, Chilmark, MA 02535

  Last Sold Summary

  • 27% Below List Price
  • $898/SF

  • Last Sold Price $2,200,000

  Last Listing Agent Russell Maloney Russell Maloney Real Estate
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  /22

  $1,200,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 576 Sq Ft

  31 North Rd, Chilmark, MA 02535

  Surrounded by three-season perennial gardens, this sun-filled two bedroom cottage offers an airy open floor plan with high ceilings that create an impressive sense of space. Natural light pours in through four skylights and classic 8 over 8 windows, while a deck off the side and rear of the home provides seamless indoor outdoor living.This home underwent a major renovation in Spring of 2024

  Russell Maloney Russell Maloney Real Estate

  31 North Rd, Chilmark, MA 02535
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  /19

  $24,000 Per Month

  • 4 Beds
  • 4 Baths
  • 2,000 Sq Ft
  • House for Rent

  44 Flanders Ln, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

  Karen Overtoom Karen M. Overtoom R.E.

  44 Flanders Ln, Chilmark, MA 02535
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  /34

  $2,475,000 Sold Sep 05, 2025

  31 N Slope Ln, Chilmark, MA 02535

  • 4 Beds
  • 3.5 Baths
  • 2,300 Sq Ft
  • Built 1983

  Last Sold Summary

  • 15% Below List Price
  • $1,076/SF
  • 117 Days On Market

  Current Estimated Value $2,668,145

  Last Listing Agent Bill Rossi Studio Realty

  31 N Slope Ln, Chilmark, MA 02535
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  /69

  Est $2,566,601 Not Listed For Sale

  276 South Rd, Chilmark, MA 02535

  • 4 Beds
  • 2 Baths
  • 2,034 Sq Ft
  • Built 1981

  276 South Rd, Chilmark, MA 02535

  Last Sold Summary

  • 32% Above List Price
  • $959/SF
  • 122 Days On Market

  • Last Sold Price $1,950,000
  • Aug 15, 2023

  Last Listing Agent Julianna Flanders Flanders Real Estate
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  /21

  $2,725,000

  • Land
  • 7.6 Acres
  • $358,553 per Acre

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535

  This rare two-lot offering off Middle Road in Chilmark presents a private sanctuary abutting approximately 50 acres of conservation land. The gently rolling landscape is accented by ancient stone walls and striking glacial boulders, creating a setting of timeless Vineyard character. Ideal for a generational compound or two distinct residences, the property offers both serenity and convenience —

  Peyton Wallace Studio Realty

  34 Ebens Ln Unit 20 and 22, Chilmark, MA 02535
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  $36,000 Per Month

  • 3 Beds
  • 3.5 Baths
  • 2,600 Sq Ft
  • House for Rent

  29 Cemetery Rd Ch216, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

  Karen Overtoom Karen M. Overtoom R.E.

  29 Cemetery Rd Ch216, Chilmark, MA 02535
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  /51

  $4,850,000 Sold Dec 05, 2025

  49 Gosnold's Way, Chilmark, MA 02535

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft
  • Built 2003

  Last Sold Summary

  • 8% Below List Price
  • $1,199/SF
  • 115 Days On Market

  Last Listing Agent Meg Bodnar Tea Lane Associates

  49 Gosnold's Way, Chilmark, MA 02535
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  /37

  Est $2,261,629 Not Listed For Sale

  2 Rockrose Path, Chilmark, MA 02535

  • 4 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 1978

  2 Rockrose Path, Chilmark, MA 02535

  Last Sold Summary

  • 46% Above List Price
  • $816/SF
  • 414 Days On Market

  • Last Sold Price $1,550,000
  • Sep 05, 2024

  Last Listing Agent Jill Napior Tea Lane Associates
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  /13

  $2,500,000

  • 1 Bed
  • 1 Bath
  • 726 Sq Ft

  18 Allen Farm Rd, Chilmark, MA 02535

  Located in the agricultural heartland of Chilmark one mile from Lucy Vincent Beach this private 2.36 acre property has a charming 1+ bedroom cottage with screened porch. There is a large building zone located between the eighty and one hundred foot contour with exciting architectural options, especially for solar designs. The cottage is offered full furnished with exception of some art and a few

  Patty Kendall Kendall & Kendall

  18 Allen Farm Rd, Chilmark, MA 02535
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  /29

  $34,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • House for Rent

  15 Loon Lane Ch203, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from

  Karen Overtoom Karen M. Overtoom R.E.

  15 Loon Lane Ch203, Chilmark, MA 02535
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  /21

  $435,000 Sold Aug 26, 2025

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535

  • Land
  • 4,356 Sq Ft
  • $4,350,000 per Acre

  Last Sold Summary

  • 3% Below List Price
  • 20 Days On Market

  Last Listing Agent Emma Bryant Landmarks at TODAY Real Estate

  0 Beach Lot Quansoo Unit 22503743, Chilmark, MA 02535
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  /53

  Est $12,341,145 Not Listed For Sale

  8 Snail Rd, Chilmark, MA 02535

  • 6 Beds
  • 8 Baths
  • 6,967 Sq Ft
  • Built 2006

  8 Snail Rd, Chilmark, MA 02535

  Last Sold Summary

  • 18% Below List Price
  • $2,153/SF
  • 25 Days On Market

  • Last Sold Price $15,000,000
  • Apr 08, 2025

  Last Listing Agent Alyssa Halisky Wallace & Co. Sotheby's
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  /4

  $1,449,000 Pending

  • Land
  • 3.9 Acres
  • $371,538 per Acre

  34 Ebens Ln, Chilmark, MA 02535

  Settled high on a peaceful ridge this 3.9-acre property is being offered with a long-term lease for 2.5 acres of prime restricted agricultural farmland abutting the property and the Tiasquam River. With the river running along the edge of the property this area is ideal for growing flowers, vegetables, and/or arbors. The land may also be used for grazing and housing livestock along with any

  Thomas Wallace Wallace & Co. Sotheby's

  34 Ebens Ln, Chilmark, MA 02535
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  /9

  $10,800 Per Month

  • 4 Beds
  • 2 Baths
  • 702 Sq Ft
  • House for Rent

  141 N Rd Ch202, Chilmark, MA 02535

  THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

  Karen Overtoom Karen M. Overtoom R.E.

  141 N Rd Ch202, Chilmark, MA 02535
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  /49

  $6,100,000 Sold Mar 24, 2026

  60 Meetinghouse Rd, Chilmark, MA 02535

  • 6 Beds
  • 8 Baths
  • 5,660 Sq Ft
  • Built 2021

  Last Sold Summary

  • 6% Below List Price
  • $1,078/SF
  • 111 Days On Market

  Last Listing Agent Jim Feiner Feiner Real Estate

  60 Meetinghouse Rd, Chilmark, MA 02535
• 

  

  /20

  Est $2,855,269 Not Listed For Sale

  23 Black Point Rd, Chilmark, MA 02535

  • 2 Beds
  • 2 Baths
  • 1,164 Sq Ft
  • Built 2004

  23 Black Point Rd, Chilmark, MA 02535

  Last Sold Summary

  • 13% Below List Price
  • $2,835/SF
  • 13 Days On Market

  • Last Sold Price $3,300,000
  • Jul 10, 2023

  Last Listing Agent Jill Napior Tea Lane Associates
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  /155

  $35,000,000

  • 8 Beds
  • 8 Baths
  • 6,841 Sq Ft

  146 Quenames Rd, Chilmark, MA 02535

  Set on 60 acres along one of the most private and unspoiled stretches of Atlantic coastline in Chilmark, this exceptional estate offers a rare combination of scale, privacy, and enduring coastal beauty. With over 800 feet of direct ocean frontage, the property commands expansive views while maintaining a true sense of seclusion, an increasingly scarce offering on Martha’s Vineyard. A gated drive

  Grace Hagerty Grace Hagerty Real Estate Inc

  146 Quenames Rd, Chilmark, MA 02535
• 

  

  /8

  $7,900 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,107 Sq Ft
  • House for Rent

  2 Paddock Cir, Chilmark, MA 02535

  Karen Overtoom Karen M. Overtoom R.E.

  2 Paddock Cir, Chilmark, MA 02535
• 

  

  /42

  $3,710,000 Sold Mar 12, 2026

  15 Old Farm Rd, Chilmark, MA 02535

  • 3 Beds
  • 6 Baths
  • 3,171 Sq Ft
  • Built 2002

  Last Sold Summary

  • 13% Below List Price
  • $1,170/SF
  • 136 Days On Market

  Current Estimated Value $3,947,969

  Last Listing Agent Tina Miller Donnelly + Co.

  15 Old Farm Rd, Chilmark, MA 02535
• 

  

  /21

  Not Listed For Sale

  3 Pepperbush Ln, Chilmark, MA 02535

  • 4 Beds
  • 2 Baths
  • 2,686 Sq Ft
  • Built 1977

  3 Pepperbush Ln, Chilmark, MA 02535

  Last Sold Summary

  • $1,824/SF
  • 0 Days On Market

  • Last Sold Price $4,900,000
  • Apr 05, 2024

  Last Listing Agent LINK Email Cache LINK
• 

  

  /31

  $2,395,000

  • 4 Beds
  • 3 Baths
  • 1,918 Sq Ft

  25 Fulling Mill Rd, Chilmark, MA 02535

  Perched atop Fulling Mill Hill this distinctive contemporary main house plus guest house offers mid-century charm and a serene retreat set on 3.3 acres of mature oak and beech forest and bordered by an ancient stone wall. Designed by renowned Yale School of Architecture Dean Paul Mitarachi, the main house features a striking circular entryway framed by mature Asiatic gardens. Step inside to

  Thomas Wallace Wallace & Co. Sotheby's

  25 Fulling Mill Rd, Chilmark, MA 02535
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  /44

  $37,000,000 Sold Jul 10, 2025

  41 Cobbs Hill Rd, Chilmark, MA 02535

  • 8 Beds
  • 5.5 Baths
  • 7,846 Sq Ft
  • Built 1993

  Last Sold Summary

  • 5% Below List Price
  • $4,716/SF
  • 39 Days On Market

  Last Listing Agent Brian Dougherty Corcoran Property Advisors

  41 Cobbs Hill Rd, Chilmark, MA 02535
• 

  

  /29

  Est $2,266,043 Not Listed For Sale

  50 South Rd, Chilmark, MA 02535

  • 5 Beds
  • 3 Baths
  • 2,427 Sq Ft
  • Built 1729

  50 South Rd, Chilmark, MA 02535

  Last Sold Summary

  • 2% Above List Price
  • $917/SF
  • 111 Days On Market

  • Last Sold Price $2,225,000
  • Jul 10, 2023

  Last Listing Agent Meg Bodnar Tea Lane Associates
• 

  

  /20

  $1,650,000

  • 2 Beds
  • 1 Bath
  • 716 Sq Ft

  46 Tiercel Ln, Chilmark, MA 02535

  Nestled on a serene 3.32-acre parcel between North Road and Tabor House in Chilmark, this property blends privacy, charm, and great potential. A sweet 2 bedroom guest house—beautifully maintained and offering excellent rental income—sits amid rolling stone walls and mature trees, creating a peaceful woodland setting. Recent updates include a new roof, siding, and HVAC system, ensuring comfort and

  Stacy Ickes Donnelly + Co

  46 Tiercel Ln, Chilmark, MA 02535
• 

  

  /3

  $5,750,000 Sold Apr 10, 2026

  23 Chockers Ln, Chilmark, MA 02535

  • 2 Beds
  • 1.5 Baths
  • 1,446 Sq Ft
  • Built 1993

  Last Sold Summary

  • $3,976/SF
  • 0 Days On Market

  Current Estimated Value $3,195,839

  Last Listing Agent Julianna Flanders Flanders Real Estate

  23 Chockers Ln, Chilmark, MA 02535
• 

  

  /24

  Est $2,559,236 Not Listed For Sale

  99 Hammett Rd, Chilmark, MA 02535

  • 4 Beds
  • 5.5 Baths
  • 2,405 Sq Ft
  • Built 2007

  99 Hammett Rd, Chilmark, MA 02535

  Last Sold Summary

  • 42% Above List Price
  • $748/SF
  • 10 Days On Market

  • Last Sold Price $1,800,000
  • Jul 26, 2023

  Last Listing Agent Julianna Flanders Flanders Real Estate
• 

  

  /12

  $1,295,000

  • Land
  • 4.4 Acres
  • $294,318 per Acre

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535

  This quiet and lovely four-and-a-half-acre lot in Chilmark is set on a gentle rise, bounded on one side by an old stone wall. The land features graceful trees and a distant water view is possible from a second floor. The lot has been staked, including a proposed home site at the highest elevation, NHESP has been completed and there are no restrictions on the lot, there's a septic design and the

  Elissa Lash Tea Lane Associates

  37 Bijah's Way Unit 96, 101, 102, Chilmark, MA 02535
• 

  

  /48

  $1,775,000 Sold Nov 07, 2025

  3 Fulling Mill Rd, Chilmark, MA 02535

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft
  • Built 1976

  Last Sold Summary

  • 5% Below List Price
  • $1,027/SF
  • 170 Days On Market

  Current Estimated Value $1,814,136

  Last Listing Agent Jill Napior Tea Lane Associates

  3 Fulling Mill Rd, Chilmark, MA 02535

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