FeaturesBathroom - Full, Cathedral Ceiling(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
LevelFirst
8 Paddock Rd, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
$5,450,000
Est. $29,501/month
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About this home
Refined Vineyard living in The Preserve. Set on a knoll overlooking the pond and sweeping grasslands, this exceptional home blends classic coastal architecture with modern luxury. The expansive great room showcases cathedral ceilings, rich millwork, and abundant natural light, with three sets of French doors opening to a bluestone patio with multiple sitting areas and a heated saltwater pool. The chef’s kitchen flows seamlessly into the dining and living spaces. One wing offers an inviting lounge and a luxurious primary suite with spa-like bath and dressing room, while the opposite wing features three guest bedrooms, each with ensuite baths and walk-in closets. Additional highlights include a proper mudroom and a finished lower level with media room, full bath, and storage. Surrounded by mature landscaping, with easy access to trails, the bike path and Farm Neck Golf Club. The Preserve is a private enclave of luxury homes and is arguably one of Oak Bluffs most exclusive neighborhoods.
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Recently Sold Nearby
Property History
Property Timeline
Listed for Sale
Apr 10, 2026
$5,450,000
Original listing
Agent: Lesley Heidt
Office: Sandpiper Realty, Inc.
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 04/10/2026 | 🏠 Listed for Sale | $5,450,000 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2026 | $16,417 | $3,289,900 |
Financial Details
Annual Property Tax
$16,417
Tax Year 2026
HOA Fee
$4,500
Annually
Assessed Value
$3,289,900
Facts & Features
Central AC
Home Facts
Type
Residential
Style
Single Family Residence
Year Built
2018
Living Area
3,300 sq ft
Lot Size
1.96 acres
Bedrooms
4
Full Baths
5
Half Baths
1
Total Rooms
9
Interior
Heating
Forced Air, Heat Pump, Electric
Cooling
Central Air
Flooring
Tile, Hardwood, Flooring - Hardwood, Flooring - Wall To Wall Carpet
Appliances
Electric Water Heater, Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Fireplace
Living Room
Fireplaces
1
Basement
Partial, Finished, Interior Entry, Bulkhead
Laundry
Flooring - Hardwood, Main Level, First Floor
Features
Cathedral Ceiling(s), Bathroom - Full, Closet/cabinets - Custom Built, Storage, Den, Mud Room, Bonus Room
Exterior
Construction
Frame
Architecture
Cape
Roof
Wood
Features
Deck, Patio, Pool - Inground Heated, Storage, Sprinkler System, Outdoor Shower
Pool
Pool - Inground Heated
Spa
None
Fencing
None
Patio/Porch
Deck, Patio
Parking
Features
Off Street
Total Spaces
8
Utilities
Electric
None
Water
Public
Sewer
Private Sewer
Gas
None
Other
None
Financial
Annual Tax
$16,417
Assessed Value
$3,289,900
HOA & Community
HOA
Yes
HOA Fee
$4,500 Annually
Fee Includes
None
Amenities
None
Optional Fee Includes
None
Association Required
Yes
MA Disclosures
Seller Disclosures
None
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
Sq Ft Source
Public Record
Documents
None
County
Dukes
Total market time (incl. prior listings)
119 days
Property Overview
Property Type
Single Family Residence
Listing Type
For Sale
Year Built
2018
Bedrooms
4
Full Bathrooms
5
Half Bathrooms
1
Living Area
3,300 sq ft
Total Rooms
9
Floor Layout
Interactive room guide
Floor Layout
Finished Area
3,300 sq ft above grade
580 sq ft below grade
FeaturesBathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
LevelFirst
FeaturesCathedral Ceiling(s), Open Floorplan
LevelFirst
FeaturesSkylight, Closet/Cabinets - Custom Built, Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Open Floorplan, Gas Stove
LevelFirst
FeaturesBathroom - Full, Cathedral Ceiling(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
LevelFirst
FeaturesSkylight, Cathedral Ceiling(s), Flooring - Hardwood, French Doors, Deck - Exterior, Open Floorplan
LevelFirst
FeaturesBathroom - Full, Bathroom - Double Vanity/Sink, Cathedral Ceiling(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
LevelFirst
FeaturesYes
Display Options
Outdoor Areas
PoolPool - Inground Heated
Patio & porchDeck, Patio
Room Markers
BABathroom (4)
BRBedroom (5)
DDining (1)
KKitchen (1)
LLiving (2)
OOffice (1)
Conceptual diagram based on MLS room data. It is not to scale and is not a substitute for architectural plans or on-site measurements.
Interior Features
Flooring:
Tile, Hardwood, Flooring - Hardwood, Flooring - Wall to Wall Carpet
Appliances:
Electric Water Heater, Water Heater, Range, Dishwasher, Microwave, Refrigerator, Washer, Dryer
Interior Features:
Cathedral Ceiling(s), Bathroom - Full, Closet/Cabinets - Custom Built, Storage, Den, Mud Room, Bonus Room
Windows:
Window(s) - Picture, Insulated Windows
Basement:
Partial, Finished, Interior Entry, Bulkhead
Laundry:
Flooring - Hardwood, Main Level, First Floor
Security:
Construction & Materials
Style:
Cape
Year Built:
2018
Structure Type:
Exterior Materials:
Frame
Roof:
Wood
Foundation:
Concrete Perimeter
Heating, Cooling & Utilities
Heating:
Forced Air, Heat Pump, Electric
Cooling:
Central Air
Hot Water:
Water Source:
Public
Sewer:
Private Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Deck, Patio, Pool - Inground Heated, Storage, Sprinkler System, Outdoor Shower
Patio & Porch:
Deck, Patio
Fencing:
Other Structures:
Lot Features:
Cleared, Level
Road Surface:
Paved
Parking & Garage
Total Parking Spaces:
8
Parking Features:
Off Street
Special Features
Fireplaces:
1
Fireplace Type:
Living Room
Pool:
Private Pool
Pool Features:
Pool - Inground Heated
View:
Yes
View Type:
Scenic View(s)
Community Amenities:
Public Transportation, Shopping, Walk/Jog Trails, Golf, Bike Path, Conservation Area
Nearby Schools
School District
Martha's Vineyard School District local
School Safety
2024-25
5.0%
Above Average
5.0%
Suspensions
1.3%
In-School
0.5% below state avg
Elementary Schools
3 schools
A-
Oak Bluffs Elementary School
1.5 mi
|
#105 of 352
|
Score: 49.0
Improved 16 spots from last year
-9.2 below state avg
402 students
Diverse
Grades PK-08
C+
Tisbury Elementary School
2.2 mi
|
#239 of 352
|
Score: 37.3
Dropped 104 spots from last year
-20.9 below state avg
312 students
Diverse
Diverse Student Body
Grades PK-08
Vineyard Montessori School
2.5 mi
Grades PK-08
High Schools
1 school
A-
Martha's Vineyard Regional High School
1.0 mi
|
#95 of 346
|
Score: 60.5
Improved 49 spots from last year
+2.3 above state avg
744 students
Diverse
19 sports
• 1,209 athletes
Strong AP Program
Rising School
Career Tech Programs
College Ready Curriculum
Grades 09-12
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Monthly Payment Breakdown
Principal & Interest
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Property Tax
$1,368
Homeowners Insurance
$200
HOA Fee
$375/mo
PMI (if <20% down)
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Loan Summary
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Payment Over Time
Year 1
95% Interest
Year 15
50/50
Year 30
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Location
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Neighborhood
8 Paddock Rd, Oak Bluffs MA 02557
Oak Bluffs, MA 02557
Listing Information
Listing Agent
Lesley Heidt
Listing Office
Sandpiper Realty, Inc.
Office Phone
508-627-3737
Agent MLS ID
CN262196
Office MLS ID
AN9490
Listing Data Updated
Aug 7, 2026 11:53 AM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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