32 Winding Oaks Ln, Dennis, MA 02638
OFF MARKET

32 Winding Oaks Ln
Dennis, MA 02638

East Dennis
  • 3 Beds
  • 2 Baths
  • 2,208 sqft (on 0.46 acres)

$1,715,500

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $9,585/mo*
Refinance Your Home

$1,715,500

Trulia Estimate
as of Jul 17, 2026
Est. Refi. Payment $9,585/mo*
Refinance Your Home
3 Beds
2 Baths
2,208 sqft
(on 0.46 acres)

Local Information

  • Map ViewExplore the area around 32 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 32 Winding Oaks Ln, Dennis, MA. 32 Winding Oaks Ln is in the East Dennis neighborhood in Dennis, MA and in ZIP code 02638. This property has 3 bedrooms, 2 bathrooms and approximately 2,208 sqft of floor space. This property has a lot size of 0.46 acres and was built in 2019.
32 Winding Oaks Ln, Dennis, MA 02638 is a 3 bedroom, 2 bathroom, 2,208 sqft single-family home in East Dennis, built in 2019. It last sold for $250,000 on Sep 27, 2019. It is currently off market. The Trulia Estimate is $1,715,500, with a rent estimate of $4,088/month.

Home Highlights

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

Home Details for 32 Winding Oaks Ln

Interior Features

Interior Details
BasementNumber of Rooms: 5
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2019Year Updated: 2023
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 0.46 acres

Price History for 32 Winding Oaks Ln

DatePriceEventSource
09/27/2019$250,000Sold
N/A

Market trends in Dennis

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$626K
$22.5KMoM
Sale-to-List Price
97.9%
Price per sq ft
$483
$12MoM
Available listings
135
21MoM
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Property Tax and Assessment

Year2025
Tax$5,553
Assessment$1,282,500
Home facts updated by county records

Comparable Sales for 32 Winding Oaks Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
23 Stephen Phillips Road, East Dennis, MA
0.13
Single-Family Home
$2,385,000
11/21/25
3
2.5
2,403
13 Hayfield Rd, South Dennis, MA
0.19
Single-Family Home
$2,425,000
02/27/26
4
3.5
3,200
13 Hayfield Road, East Dennis, MA
0.19
Single-Family Home
$2,425,000
02/27/26
4
3.5
3,201
10 Briarfield Road, South Dennis, MA
0.75
Single-Family Home
$840,000
07/02/26
3
3
2,545
14 Prince Way, South Dennis, MA
0.73
Single-Family Home
$794,500
06/29/26
4
3
2,312
65 Forest Pines Dr, South Dennis, MA
0.91
Single-Family Home
$977,500
06/26/26
3
2
1,648
37 Stony Way, East Dennis, MA
0.45
Single-Family Home
$2,685,000
05/15/26
5
2.5
2,658
144 Forest Pines Drive, South Dennis, MA
0.91
Single-Family Home
$578,000
03/09/26
2
1.5
1,380
276 Scargo Hill Road, South Dennis, MA
0.72
Single-Family Home
$769,000
05/05/26
3
1.5
1,152
65 Forest Pines Drive, South Dennis, MA
1.00
Single-Family Home
$977,500
06/26/26
3
2
1,648

Nearby homes

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Assigned Schools

These are the assigned schools for 32 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
    Flag
  • 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

8 pet-friendly rentals in Dennis, MA

Explore by feature - Air Conditioning

16 rentals with air conditioning in Dennis, MA

Explore by feature - Washer/dryer

19 rentals with a washer/dryer in Dennis, MA

Homes for sale near 32 Winding Oaks Ln

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Off Market Homes Near 32 Winding Oaks Ln

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