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8 Paddock Rd, Oak Bluffs MA 02557

Oak Bluffs, MA 02557
$5,450,000
Est. $29,501/month
4
Beds
5.5
Baths
3,300
Sq Ft
$1,652
Price/Sq Ft
1.96
Acres
2018
Year Built
8
Parking
90
Days on Market
Active Listed Apr 10, 2026 • MLS# 73499730 Copied! • Updated Jun 26, 2026

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.

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
Features Off Street
Total Spaces 8
Electric None
Water Public
Sewer Private Sewer
Gas None
Other None
Annual Tax $16,417
Assessed Value $3,289,900
HOA Yes
HOA Fee $4,500 Annually
Fee Includes None
Amenities None
Optional Fee Includes None
Association Required Yes
Seller Disclosures None
Possession None
Accepted Financing None
Structure Type []
Sq Ft Source Public Record
Documents None
County Dukes
Total market time (incl. prior listings) 77 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

Room Details

First Floor

Bedroom4
Bathroom - Full, Cathedral Ceiling(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Bedroom3
Bathroom - Full, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Dining Room
Cathedral Ceiling(s), Open Floorplan
Kitchen
Skylight, Closet/Cabinets - Custom Built, Flooring - Hardwood, Dining Area, Countertops - Stone/Granite/Solid, Kitchen Island, Open Floorplan, Gas Stove
Bedroom2
Bathroom - Full, Cathedral Ceiling(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile
Living Room
Skylight, Cathedral Ceiling(s), Flooring - Hardwood, French Doors, Deck - Exterior, Open Floorplan
Master Bedroom
Bathroom - Full, Bathroom - Double Vanity/Sink, Cathedral Ceiling(s), Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Flooring - Stone/Ceramic Tile

Other Floor

Bathroom1
Bedroom5
Bathroom2
Bathroom3
Office
Family Room
Master Bathroom
Yes

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
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
E

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
H

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
Learn about these ratings

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Including down payment
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Monthly Payment Breakdown

Principal & Interest $0
Property Tax $1,368
Homeowners Insurance $200
HOA Fee $375/mo
PMI (if <20% down) $0

Loan Summary

Total of 360 payments $0
Total principal paid $0
Total interest paid $0

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Payment Over Time

Interest
Principal
Year 1
95% Interest
Year 15
50/50
Year 30
95% Principal
* Estimates only. Actual payments may vary. Consult with a lender for accurate figures.

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 Jun 26, 2026 3:22 PM 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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