8 Winding Oaks Ln, Dennis, MA 02660
OFF MARKET

8 Winding Oaks Ln
Dennis, MA 02660

East Dennis
  • 4 Beds
  • 4.5 Baths
  • 4,669 sqft (on 0.46 acres)

$2,730,000

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $14,910/mo*
Refinance Your Home

$2,730,000

Trulia Estimate
as of Jul 4, 2026
Est. Refi. Payment $14,910/mo*
Refinance Your Home
4 Beds
4.5 Baths
4,669 sqft
(on 0.46 acres)

Local Information

  • Map ViewExplore the area around 8 Winding Oaks Ln.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 8 Winding Oaks Ln, Dennis, MA. 8 Winding Oaks Ln is in the East Dennis neighborhood in Dennis, MA and in ZIP code 02660. This property has 4 bedrooms, 5 bathrooms and approximately 4,669 sqft of floor space. This property has a lot size of 0.46 acres and was built in 2025.
8 Winding Oaks Ln, Dennis, MA 02660 is a 4 bedroom, 5 bathroom, 4,669 sqft single-family home in East Dennis, built in 2025. It is currently off market. The Trulia Estimate is $2,730,000, with a rent estimate of $7,186/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 8 Winding Oaks Ln

Interior Features

Interior Details
BasementAtticNumber of Rooms: 12Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Mud Room, Office, Pantry, Recreation RoomCeiling Fan
Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood, Laminate
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: ShingleLawnPatioPorchSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2025
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 0.46 acres

Market trends in Dennis

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$603K
$13.33KMoM
Sale-to-List Price
—
Price per sq ft
$471
$41MoM
Available listings
156
29MoM
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Property Tax and Assessment

Year2025
Tax$624
Assessment$144,200
Home facts updated by county records

Comparable Sales for 8 Winding Oaks Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4 Surrey Ln, South Dennis, MA
0.28
Single-Family Home
$1,940,000
06/24/26
5
4
4,537
149 Greenland Cir, South Dennis, MA
0.50
Single-Family Home
$1,530,000
05/18/26
3
3.5
3,840
57 Bakers Pond Road, East Dennis, MA
0.28
Single-Family Home
$960,000
10/02/25
3
2.5
2,458
57 Bakers Pond Rd, South Dennis, MA
0.28
Single-Family Home
$960,000
10/01/25
3
2.5
2,458
86 Greenland Circle, South Dennis, MA
0.26
Single-Family Home
$1,555,375
03/12/26
3
3
3,202
36 Island Street, South Dennis, MA
0.39
Single-Family Home
$935,000
05/04/26
3
3
2,848
36 Island St, South Dennis, MA
0.39
Single-Family Home
$935,000
05/04/26
3
3
2,848
38 Greenland Cir, South Dennis, MA
0.44
Single-Family Home
$1,300,000
01/29/26
3
2.5
2,019
38 Greenland Circle, South Dennis, MA
0.44
Single-Family Home
$1,300,000
01/29/26
3
2.5
1,868
4 Landing Ln, South Dennis, MA
0.33
Single-Family Home
$635,000
02/05/26
3
1.5
1,302

Nearby homes

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Assigned Schools

These are the assigned schools for 8 Winding Oaks Ln.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

East Dennis
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about East Dennis

At least 18 Trulia users voted on each feature.

  • 96 % Say car is needed

  • 96 % Say it's dog friendly

  • 95 % Say yards are well-kept

  • 91 % Say parking is easy

  • 85 % Say they plan to stay for at least 5 years

  • 83 % Say it's quiet

  • 83 % Say there's wildlife

  • 75 % Say people would walk alone at night

  • 74 % Say there's holiday spirit

  • 69 % Say neighbors are friendly

  • 48 % Say it's walkable to restaurants

  • 42 % Say there are sidewalks

  • 42 % Say streets are well-lit

  • 29 % Say it's walkable to grocery stores

  • 28 % Say kids play outside

  • 15 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "It is very safe with lots of parks and fields. I have lived here all my life and everyone is very friendly."
    0
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  • Trulia User
    "There is a lot of local restaurants, shops and other small business. Neighborhoods are very quiet. Summer life is great! "
    0
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  • Trulia User
    "It’s a great neighborhood for walking my dog. Dog owners are very considerate of their neighbors. Quiet neighborhood. "
    0
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  • Mona
    "We have rented for years in dennis and love it so much we bought a year round home. Neighbors and community are friendly and welcoming. "
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  • Jim G.
    "Of all the villages in the Town of Dennis, East Dennis is by far one of the most prestigious and exceptional places to live. From breakfast at Grumpy's on Rte. 6A, to waterside dining on the harbor from the Sesuit Harbor Cafe, to the elegant Marshside Restaurant, no area compares to beauty of Cold Storage beach and Harborview Beach. Launch your kayak or 60 foot yacht from the deep water ramp of Sesuit Harbor. No bridges to worry about- Cape Cod Bay awaits your discovery! Walkers take advantage of the slow pace in the "Neck", the largest private home marks it's location in East Dennis"
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Apartments for Rent

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Explore by feature - Pet Friendly

7 pet-friendly rentals in Dennis, MA

Explore by feature - Air Conditioning

10 rentals with air conditioning in Dennis, MA

Explore by feature - Washer/dryer

13 rentals with a washer/dryer in Dennis, MA

Homes for sale near 8 Winding Oaks Ln

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Off Market Homes Near 8 Winding Oaks Ln

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