8 Paddock Rd
Oak Bluffs, MA 02557
4 Beds
5.5 Baths
3,300 sqft (on 1.95 acres)
4 Beds
5.5 Baths
3,300 sqft
(on 1.95 acres)
Local Information
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Description
Refined Vineyard Living in The Preserve - Set atop a knoll overlooking sweeping grassland and the pond, this exceptional residence embodies the perfect balance of classic coastal architecture and modern sophistication. Located within the prestigious enclave of The Preserve, the home offers a combination of privacy, elegance, and seamless indoor-outdoor living. At its core, an expansive great room features soaring cathedral ceilings, rich paneling, and exquisite millwork. Bathed in natural light from dormers and oversized windows, the space is both grand and inviting. Three sets of French doors open to a bluestone terrace with multiple seating areas and a heated saltwater pool—creating a stunning backdrop for al fresco dining, entertaining, and quiet relaxation. The chef’s kitchen is thoughtfully positioned to overlook both the dining area and great room, allowing for effortless everyday living and gracious hosting. The home’s layout is equally intentional: one wing offers a secondary living room or study, along with a luxurious primary suite complete with a spa-like bath and dressing room. The opposite wing features three spacious guest bedrooms, each with cathedral ceilings, walk-in closets, and ensuite baths, ensuring comfort and privacy for family and guests alike. Additional amenities include a well-appointed mudroom with side entrance, a dedicated laundry room, and a finished lower level with a media room, full bath, and abundant storage. Custom built-ins, refined finishes, and thoughtful architectural details enhance the home’s timeless appeal throughout. Surrounded by beautifully curated grounds, the property offers a true sense of seclusion. Residents of The Preserve enjoy access to scenic walking trails connecting to conservation land, as well as convenient proximity to the bike path, Farm Neck Golf Club, and all down-island towns.
Home Highlights
Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
$375/Monthly
Price/Sqft
$1,652
Listed
10 days ago
Home Details for 8 Paddock Rd
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Interior Details Basement: Nicely finished with a media room, full bath, and lots of storage space. Not included in square footage noted above.Number of Rooms: 9 |
Beds & Baths Number of Bedrooms: 4Main Level Bedrooms: 4Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 3300 Square Feet |
Appliances & Utilities Utilities: CblAppliances: Stove: Yes, Washer: Yes |
Heating & Cooling Heating: Heat PumpNo CoolingHas HeatingHeating Fuel: Heat Pump |
Fireplace & Spa Fireplace: Yes, in central great room |
Windows, Doors, Floors & Walls Flooring: Hardwood and tile |
Levels, Entrance, & Accessibility Floors: Hardwood And Tile |
View Has a ViewView: Pond, Pasture |
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Exterior Home Features Other Structures: Shed in the back yard for outside gear.Exterior: Patio, P/Pool, Cov, PubBchFoundation: Poured concrete |
Parking & Garage No CarportNo GarageNo Attached GarageParking: Circular car court |
Frontage Frontage Type: NoneNot on Waterfront |
Water & Sewer Sewer: Septic Tank |
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Days on Market: 10 |
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Year Built Year Built: 2018 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family Residence |
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Price List Price: $5,450,000Price Per Sqft: $1,652 |
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MLS Status: A |
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Direction & Address City: Oak Bluffs |
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Listing Agent Listing ID: 44395 |
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Building Area Building Area: 3300 Square Feet |
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Has an HOAHOA Fee: $4,500/Annually |
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Lot Area: 1.95 Acres |
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Listing Agreement Type: E |
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BasementMls Number: 44395Water ViewWater View: Pond |
Last check for updates: about 9 hours ago
Listing courtesy of Lesley Heidt
Sandpiper Realty
Price History for 8 Paddock Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 04/10/2026 | $5,450,000 | Listed For Sale | MLS PIN #73499730 |
| 12/15/2025 | $5,450,000 | ListingRemoved | LINK #43612 |
| 08/07/2025 | $5,450,000 | Listed For Sale | Martha's Vineyard MLS #32500251 |
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New Listings near 8 Paddock Rd
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $16,096 |
| Assessment | $3,187,300 |
Home facts updated by county records
Comparable Sales for 8 Paddock Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.33 | Single-Family Home | $2,900,000 | 03/30/26 | 4 | 4 | 5,169 | |
0.12 | Single-Family Home | $1,850,000 | 03/31/26 | 4 | 3 | 3,142 | |
0.15 | Single-Family Home | $1,449,000 | 08/19/25 | 3 | 2 | 2,284 | |
0.42 | Single-Family Home | $1,600,000 | 01/20/26 | 4 | 2.5 | 2,855 | |
0.60 | Single-Family Home | $1,600,000 | 01/06/26 | 4 | 4 | 3,927 | |
0.57 | Single-Family Home | $1,765,000 | 08/18/25 | 4 | 3.5 | 2,450 | |
1.01 | Single-Family Home | $5,500,000 | 05/20/25 | 4 | 4.5 | 3,262 | |
0.68 | Single-Family Home | $2,250,000 | 12/10/25 | 4 | 3.5 | 3,014 | |
0.62 | Single-Family Home | $1,700,000 | 11/03/25 | 3 | 4 | 2,558 | |
0.76 | Single-Family Home | $1,995,000 | 08/29/25 | 4 | 3.5 | 2,891 |
Assigned Schools
These are the assigned schools for 8 Paddock Rd.
- Oak Bluffs Elementary School
- PK-8
- Public
- 390 Students
7/10GreatSchools RatingParent Rating AverageAn excellent school where students seem to be happy, learning and engaged. You can tell the teachers really care about and truly want the best for their students. The new principal is very energetic, involved and approachable and he seems very well-liked by students, parents and the staff (which is everything).Parent Review6mo ago - Martha's Vineyard Regional High School
- 9-12
- Public
- 703 Students
6/10GreatSchools RatingParent Rating AverageStandards for academic engagement are ON THE FLOOR at this school. The “c1” courses are equivalent to a special ed class in any other school, and an honors class to a typical c1 course. Very, very low expectations for C1 students, often no homework at all, or just one assignment per week, and very little in class work. Many teachers in the school are just blatantly bad at their jobs. The school is not able to address it due to a lack of new teachers, but also because they refuse to train teachers properly. I will admit, many teachers are incredible, but it is unacceptable that the academic standards are so incredibly low and how the administration allows teachers to get by without being able to teach the curriculum during the school year. Specifically, this school and the school system on the island in general is notorious for its awful math program. The school is now having to extend the math period for freshmen because of the amount of failing students (likely more changes to come). The administration has also consistently shown disregard for the opinions of students and families, particularly about the new phone policy. Many valid arguments were simply dismissed or never addressed or answered prior to the establishment of the policy. The administration is also very unaware of what is actually happening (particularly the former principal) in the student body, as a very, very small percentage of students are actually following the policy—the vast majority sticking to the old rule of just not having phones out in class, while the administration continually brags about how well the implementation of the policy has gone. Hopefully as the former principal is now gone some of these issues will be addressed, but it is important to note that there are many issues with this school.Student Review8mo ago 
Check out schools near 8 Paddock Rd.
What Locals Say about Oak Bluffs
At least 18 Trulia users voted on each feature.
96 % Say it's dog friendly
86 % Say kids play outside
83 % Say yards are well-kept
79 % Say it's walkable to restaurants
79 % Say car is needed
78 % Say people would walk alone at night
78 % Say it's walkable to grocery stores
73 % Say there's wildlife
73 % Say they plan to stay for at least 5 years
70 % Say there's holiday spirit
67 % Say it's quiet
62 % Say parking is easy
59 % Say neighbors are friendly
47 % Say there are community events
44 % Say there are sidewalks
36 % Say streets are well-lit
Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Lesley Heidt, Sandpiper Realty
© 2026 LINK, All Rights Reserved. Data last updated: 2026-05-09 16:39:26 PDT. Some properties may no longer be for sale if they have gone under contract, have sold, or are no longer being offered for sale since the last update.
8 Paddock Rd, Oak Bluffs, MA 02557 is a 4 bedroom, 6 bathroom, 3,300 sqft single-family home built in 2018. This property is currently available for sale and was listed by LINK on Apr 30, 2026. The MLS # for this home is MLS# 44395.