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Sophisticated Representation for Exceptional Properties

Rose Ryley brings clarity, discretion, and local expertise to every transaction at Wallace & Co. Sotheby’s International Realty. A New England native with over a decade of experience selling real estate on island, she blends deep market knowledge with a thoughtful, people-first approach to the luxury market.

15+

Years of Experience

112

Closed Sales

100%

Discretion

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Get to Know Me

Renowned real estate professional Rose Ryley stands out on the Vineyard for her deep market expertise and strategic guidance, offering clients a distinct advantage in navigating the island’s most competitive properties. With an Anthropology degree from Tulane University and a background rooted in a family of builders, Rose offers a rare blend of people-focused insight and a trained eye for craftsmanship and structural detail. This perspective allows her to evaluate properties holistically - understanding not only their investment potential, but also how they align with her clients’ lifestyles and long-term goals.

Deeply connected to the Island community, Rose is a passionate advocate for nature and preservation, serving on the boards of the Oak Bluffs Conservation Commission and the Martha’s Vineyard Garden Club. When she’s not advising clients, she’s likely cheering on her son at swim meets or watching him race Optis out on the water.

Featured Listings

  • 308 South Road For Sale

    $7,350,000

    308 South Road, Chilmark, MA 02535

    • 4 Beds
    • 5 Baths
    • 3,490 Sq.Ft.
  • 16 Frog Hollow For Sale

    $4,695,000

    16 Frog Hollow, Vineyard Haven, MA 02568

    • 3 Beds
    • 2 Baths
    • 1,716 Sq.Ft.
  • 114 Meetinghouse Way For Sale

    $3,100,000

    114 Meetinghouse Way, Edgartown, MA 02539

    • 1 Bed
    • 1 Bath
    • 1,250 Sq.Ft.
  • 112 Dukes County Avenue For Sale

    $599,000

    112 Dukes County Avenue, Oak Bluffs, MA 02557

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Client Testimonial

"We had a very positive experience working with Rose on the purchase of a home on Martha’s Vineyard. From our first contact with her, she worked quickly and efficiently to address and respond to our many questions. She went above and beyond our expectations when it came to researching any issues and resolving any problems that came up. She handled all of the transaction details on a timely basis. It was always easy to communicate with her via text, email, or phone, all of which she responded to promptly. She has continued to assist us even after the closing with details that came up regarding the house. Rose is both highly professional and very pleasant to deal with. We highly recommend Rose for your next real estate purchase or sale on the Vineyard."
"We had a very positive experience working with Rose on the purchase of a home on Martha’s Vineyard. From our first contact with her, she worked quickly and efficiently to address and respond to our many questions. She went above and beyond our expectations when it came to researching any issues and resolving any problems that came up. She handled all of the transaction details on a timely basis. It was always easy to communicate with her via text, email, or phone, all of which she responded to promptly. She has continued to assist us even after the closing with details that came up regarding the house. Rose is both highly professional and very pleasant to deal with. We highly recommend Rose for your next real estate purchase or sale on the Vineyard."
Buyer
"My experience with Rose was incredibly good. She was on top of every detail and anticipated items before I even thought to bring them up. I have already recommended her to friends who are looking for a home on Martha's Vineyard, and they are so pleased with their experience as well. Rose is so well organized and pays such careful attention to the needs of her clients and the process in general. Her responsiveness to phone calls, emails, in-person meetings, etc., was truly remarkable. I definitely got the sense that Rose wants her clients to succeed and to find their dream home and is really willing to go and walk that extra mile with you to do so. She is extremely knowledgeable and passionate about Martha's Vineyard and a super competent real estate professional. She is also poised, thoughtful, and gracious and just plain fun to work with!"
"My experience with Rose was incredibly good. She was on top of every detail and anticipated items before I even thought to bring them up. I have already recommended her to friends who are looking for a home on Martha's Vineyard, and they are so pleased with their experience as well. Rose is so well organized and pays such careful attention to the needs of her clients and the process in general. Her responsiveness to phone calls, emails, in-person meetings, etc., was truly remarkable. I definitely got the sense that Rose wants her clients to succeed and to find their dream home and is really willing to go and walk that extra mile with you to do so. She is extremely knowledgeable and passionate about Martha's Vineyard and a super competent real estate professional. She is also poised, thoughtful, and gracious and just plain fun to work with!"
Kelly B.
"When I met Rose, I was immediately impressed. She was reliable, knowledgeable, and very organized. Three factors that were important to me when finding someone to work with. She did not let us down. The entire process went so smoothly. I highly recommend Rose!"
"When I met Rose, I was immediately impressed. She was reliable, knowledgeable, and very organized. Three factors that were important to me when finding someone to work with. She did not let us down. The entire process went so smoothly. I highly recommend Rose!"
Marianna C.
"Rose quickly understood us and what we were looking for to buy a new home. She provided honest and helpful info on locations, pros and cons, and what we should expect. She was knowledgeable about so many things but also knew how to obtain answers if she did not know. Rose was trustworthy and highly ethical. When selling our home, Rose worked diligently to address buyer requests, run down necessary information, and ready everything for the sale. Rose gave terrific advice and always knew when to push or hold back. We could not be more pleased with our experience, and we were so happy that we had Rose to guide us through the process."
"Rose quickly understood us and what we were looking for to buy a new home. She provided honest and helpful info on locations, pros and cons, and what we should expect. She was knowledgeable about so many things but also knew how to obtain answers if she did not know. Rose was trustworthy and highly ethical. When selling our home, Rose worked diligently to address buyer requests, run down necessary information, and ready everything for the sale. Rose gave terrific advice and always knew when to push or hold back. We could not be more pleased with our experience, and we were so happy that we had Rose to guide us through the process."
Peter C.
"Rose has worked with me on the sale of two homes on Martha's Vineyard. Her professionalism, people skills, and real estate knowledge are second to none. I have been involved in real estate purchases and sales in multiple countries and the US, and I found Rose to be the best agent I have come across in 20 years. I would highly recommend her. Thank you, Rose, sincerely."
"Rose has worked with me on the sale of two homes on Martha's Vineyard. Her professionalism, people skills, and real estate knowledge are second to none. I have been involved in real estate purchases and sales in multiple countries and the US, and I found Rose to be the best agent I have come across in 20 years. I would highly recommend her. Thank you, Rose, sincerely."
Rich C.
"Rose worked with us tirelessly for one year during our search for a home on Martha's Vineyard. She introduced us to properties we hadn't even considered and educated us on the island. She was so patient despite our fluctuations about what we thought we wanted, and her response time was always really quick. She helped us find our home on MV, which we love, and the whole process working with Rose was wonderful. We really recommend Rose and will only work with her in the future!"
"Rose worked with us tirelessly for one year during our search for a home on Martha's Vineyard. She introduced us to properties we hadn't even considered and educated us on the island. She was so patient despite our fluctuations about what we thought we wanted, and her response time was always really quick. She helped us find our home on MV, which we love, and the whole process working with Rose was wonderful. We really recommend Rose and will only work with her in the future!"
Jody L.
"Rose was a joy to work with. As you can imagine, I needed a lot of help going through this process, and Rose was always available when I called her. She has a wealth of knowledge about the entire vineyard and is very forthcoming with it. She is honest about the value of residential areas and does not hesitate to point out any negatives about a listing. I guess what I valued most about her was her honesty. She was not just about selling and making a commission, but more about guiding you through the process and getting you where you wanted to be. Her perception skills are excellent! She knew what I liked and would tell me as new properties came on the market whether she thought I should take the trip over to look at them or not. This made the process less cumbersome. Even after the closing, Rose gave me information regarding trash pickup, plumbers, etc., all things that we take for granted but had no knowledge of on the vineyard. Couldn't have asked for better! Always sweet and smiling even when I wasn't. You will not be sorry if you work with Rose in the future!"
"Rose was a joy to work with. As you can imagine, I needed a lot of help going through this process, and Rose was always available when I called her. She has a wealth of knowledge about the entire vineyard and is very forthcoming with it. She is honest about the value of residential areas and does not hesitate to point out any negatives about a listing. I guess what I valued most about her was her honesty. She was not just about selling and making a commission, but more about guiding you through the process and getting you where you wanted to be. Her perception skills are excellent! She knew what I liked and would tell me as new properties came on the market whether she thought I should take the trip over to look at them or not. This made the process less cumbersome. Even after the closing, Rose gave me information regarding trash pickup, plumbers, etc., all things that we take for granted but had no knowledge of on the vineyard. Couldn't have asked for better! Always sweet and smiling even when I wasn't. You will not be sorry if you work with Rose in the future!"
Joyce B.
"At our first meeting, I immediately knew Rose was the perfect choice as the realtor to handle the sale of our family home. She was very sensitive to our feelings about the sale and put us at ease immediately. Rose listened carefully to all of our concerns and understood our needs with regard to the timing of the sale. She is experienced and was able to answer all of our questions as they arose. She used her expert knowledge of the local market to list the house at a great price that would get us results within our time constraints. As soon as the property went live, we had several interested potential buyers. She stayed in close contact and advised us throughout the entire process. Rose handled any issues that arose with expertise, and she went far above and beyond the call of duty to get the job done. I feel very satisfied that the outcome was reasonable and fair to us as well as the buyers. She did an outstanding job from start to finish!"
"At our first meeting, I immediately knew Rose was the perfect choice as the realtor to handle the sale of our family home. She was very sensitive to our feelings about the sale and put us at ease immediately. Rose listened carefully to all of our concerns and understood our needs with regard to the timing of the sale. She is experienced and was able to answer all of our questions as they arose. She used her expert knowledge of the local market to list the house at a great price that would get us results within our time constraints. As soon as the property went live, we had several interested potential buyers. She stayed in close contact and advised us throughout the entire process. Rose handled any issues that arose with expertise, and she went far above and beyond the call of duty to get the job done. I feel very satisfied that the outcome was reasonable and fair to us as well as the buyers. She did an outstanding job from start to finish!"
Jean C.
"Rose exceeded all of our expectations when she sold 75 South Water Street in Edgartown for us for $9M. She was a terrific team member and an excellent communicator. She was thorough in all she did, reaching out to local authorities and checking on many items that could have affected the sale. She helped us set a realistic offering price and successfully navigate some surprises unearthed in inspections. She knew exactly when to engage our lawyer in the process and when to handle matters herself. Rose is an outstanding professional, a caring woman, and an expert realtor."
"Rose exceeded all of our expectations when she sold 75 South Water Street in Edgartown for us for $9M. She was a terrific team member and an excellent communicator. She was thorough in all she did, reaching out to local authorities and checking on many items that could have affected the sale. She helped us set a realistic offering price and successfully navigate some surprises unearthed in inspections. She knew exactly when to engage our lawyer in the process and when to handle matters herself. Rose is an outstanding professional, a caring woman, and an expert realtor."
Elaine P.
"Rose was amazing to work with. She was extremely responsive from the very beginning of the process. She went above and beyond to ensure that we had a great experience. Her coordination with all of the parties involved made everything run smoothly for us. We would absolutely recommend Rose for anyone looking to purchase a home on MV. She is great."
"Rose was amazing to work with. She was extremely responsive from the very beginning of the process. She went above and beyond to ensure that we had a great experience. Her coordination with all of the parties involved made everything run smoothly for us. We would absolutely recommend Rose for anyone looking to purchase a home on MV. She is great."
Jaidip C.

Notable Sales

  • 139 and 120 Little Homers Pond Sold

    $14,000,000

    139 and 120 Little Homers Pond, West Tisbury, MA 02575

    • 4 Beds
    • 5 Baths
    • 3,542 Sq.Ft.
  • 75 S Water St Sold

    $9,000,000

    75 South Water Street, Edgartown, MA 02539

    • 5 Beds
    • 3 Baths
    • 2,612 Sq.Ft.
  • 37 Morse Street Sold

    $5,375,000

    37 Morse Street, Edgartown, MA 02539

    • 4 Beds
    • 6 Baths
    • 2,911 Sq.Ft.
  • 37 Morse St Sold

    $4,234,000

    37 Morse Street, Edgartown, MA 02539

    • 4 Beds
    • 6 Baths
    • 2,911 Sq.Ft.
  • 43 Naushon Road Sold

    $3,750,000

    43 Naushon Road, West Tisbury, MA 02575

    • 6 Beds
    • 5 Baths
    • 3,694 Sq.Ft.
  • 188 Pond Rd Sold

    $3,210,000

    188 Pond Road, West Tisbury, MA 02575

    • 4 Beds
    • 3 Baths
    • 2,789 Sq.Ft.
  • 18 South Pond Road Sold

    $2,895,000

    18 South Pond Road, West Tisbury, MA 02575

    • 5 Beds
    • 5 Baths
    • 4,239 Sq.Ft.
  • 6 Browns Farm Lane Sold

    $2,395,000

    6 Browns Farm Lane, Edgartown, MA 02539

  • 2 Bradford Court Sold

    $2,300,000

    2 Bradford Court, Oak Bluffs, MA 02557

    • 3 Beds
    • 3 Baths
    • 1,392 Sq.Ft.
  • 84 Cuttyhunk Ave Sold

    $2,300,000

    84 Cuttyhunk Avenue, Vineyard Haven, MA 02568

    • 3 Beds
    • 4 Baths
    • 2,396 Sq.Ft.
  • 230 Pond Road Sold

    $2,280,000

    230 Pond Road, West Tisbury, MA 02575

    • 4 Beds
    • 4 Baths
    • 3,527 Sq.Ft.
  • 7 Parsonage Woods Road Sold

    $1,800,000

    7 Parsonage Woods Road, West Tisbury, MA 02575

    • 3 Beds
    • 2 Baths
    • 1,822 Sq.Ft.
  • 10 Combra Way Sold

    $1,695,000

    10 Combra Way, Oak Bluffs, MA 02557

    • 3 Beds
    • 4 Baths
    • 2,200 Sq.Ft.
  • 2 Mattakesett Bay Road # M1 Sold

    $1,550,000

    2 Mattakesett Bay Road # M1, Edgartown, MA 02539

    • 3 Beds
    • 4 Baths
    • 1,410 Sq.Ft.
  • 34 Tenth Street South Sold

    $1,195,000

    34 Tenth Street South, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,110 Sq.Ft.
  • 13 Flamingo Drive Sold

    $1,125,000

    13 Flamingo Drive, Edgartown, MA 02539

    • 3 Beds
    • 2 Baths
    • 1,512 Sq.Ft.
  • 19 Tyler's Creek Sold

    $1,050,000

    19 Tyler's Creek, Oak Bluffs, MA 02557

  • 30 Pine Street Sold

    $1,040,000

    30 Pine Street, Edgartown, MA 02539

    • 1 Bed
    • 1 Bath
    • 675 Sq.Ft.
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Areas of Expertise

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