16 Winding Oaks Ln, Dennis, MA 02638
OFF MARKET

$1,906,300

Trulia Estimate
  • 3 Beds
  • 2 Baths
  • 1,947 sqft (on 0.46 acres)

16 Winding Oaks Ln, Dennis, MA 02638

East Dennis
Est. Refi. Payment $11,037/mo*
Refinance Your Home
Currently Off Market - Sold Dec 30, 2019 for $945,975

Home Value

Trulia Estimate
$1.91M
Since last month
Increased$15K (+0.8%)
Since last year
Increased$176K (+10.2%)
Since last sale
Increased$960K (+101.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +370% in the last 10 years
MonthEstimated value
2026
August 2026$1.91M
August 2026$1.88M
July 2026$1.89M
June 2026$1.88M
May 2026$1.81M
April 2026$1.76M
March 2026$1.75M
February 2026$1.72M
January 2026$1.71M
2025
2024
2023
2022
2021
2020
2019

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
23 Stephen Phillips Road, East Dennis, MA
0.14
Single-Family Home
$2,385,000
11/21/25
3
2.5
2,403
12 Fairway Drive, East Dennis, MA
0.64
Single-Family Home
$815,000
08/28/26
3
2
2,153
83 Airline Road, East Dennis, MA
0.64
Single-Family Home
$748,000
08/27/26
3
2
1,300
43 Palmer Lane, East Dennis, MA
0.66
Single-Family Home
$990,000
08/06/26
3
2.5
2,220
57 Bakers Pond Road, East Dennis, MA
0.64
Single-Family Home
$960,000
10/02/25
3
2.5
2,458
14 Timber Lane, East Dennis, MA
0.65
Single-Family Home
$940,500
06/10/26
3
2.5
2,072
4 Landing Lane, East Dennis, MA
0.64
Single-Family Home
$635,000
02/05/26
3
1.5
1,302
13 Hayfield Rd, South Dennis, MA
0.21
Single-Family Home
$2,425,000
02/27/26
4
3.5
3,200
13 Hayfield Road, East Dennis, MA
0.21
Single-Family Home
$2,425,000
02/27/26
4
3.5
3,201
1354 Route 134, South Dennis, MA
0.83
Single-Family Home
$885,000
07/21/26
3
2.5
2,100

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
37 Winding Way, Dennis, MA 02638
0.09
$3,935,700
5
4.5
5,456
Off Market
11 Mooncusser Lane, East Dennis, MA 02641
0.07
$2,335,900
3
2.5
2,234
Off Market
5 Mooncusser Lane, East Dennis, MA 02641
0.07
$2,520,000
3
2.5
2,331
Off Market
165 Bridge Street, Dennis, MA 02638
0.04
$3,516,100
7
7
4,863
Off Market
94 Old Town Lane, East Dennis, MA 02641
0.04
$2,477,600
4
4.5
3,093
Off Market
2 MOONCUSSER Lane, East Dennis, MA 02641
0.08
$3,044,100
3
3
2,731
Off Market
1 Stephen Phillips Road, East Dennis, MA 02641
0.07
$2,123,800
3
4
2,087
Off Market
95 OLD TOWN Lane, East Dennis, MA 02641
0.07
$2,269,300
3
2.5
2,827
Off Market
71 Old Town Lane, East Dennis, MA 02641
0.10
$4,732,900
5
3.5
4,500
Off Market
1 Stonewall Way, East Dennis, MA 02641
0.10
$2,864,500
4
4.5
3,145
Off Market
8 Stonewall Way, East Dennis, MA 02641
0.12
-
-
-
-
Off Market
56 Old Town Lane, East Dennis, MA 02641
0.14
$3,627,600
5
2.5
3,100
Off Market

Local Information

  • Map ViewExplore the area around 16 Winding Oaks Ln.
  • Schools1 Preschool School2 Elementary Schools2 Middle Schools1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2018
0.46 acre lot
1,947 sqft
$979/sqft
Garage

About this House

This single-family home is located at 16 Winding Oaks Ln, Dennis, MA. 16 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 1,947 sqft of floor space. This property has a lot size of 0.46 acres and was built in 2018.
16 Winding Oaks Ln, Dennis, MA 02638 is a 3 bedroom, 2 bathroom, 1,947 sqft single-family home in East Dennis, built in 2018. It last sold for $945,975 on Dec 30, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,906,300, with a rent estimate of $3,704/month.

Home Details for 16 Winding Oaks Ln

Interior Features

Interior Details
BasementNumber of Rooms: 6
Heating & Cooling
Heating: GasAir ConditioningHeating Fuel: Gas
Levels, Entrance, & Accessibility
Stories: 1
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 2018Year 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 and Tax history

DateEventPrice
Dec 30, 2019
Source: N/A
Sold
$945,975

Market trends in Dennis

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$661K
$20KMoM
Sale-to-List Price
99.1%
1.1%MoM
Price per sq ft
$549
$49MoM
Available listings
119
5MoM

Around this home

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
    Flag
  • Trulia User
    "There is a lot of local restaurants, shops and other small business. Neighborhoods are very quiet. Summer life is great! "
    0
    Flag
  • 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. "
    0
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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"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 16 Winding Oaks Ln

  • What is 16 Winding Oaks Ln estimated to be worth?
    Trulia's estimated value for 16 Winding Oaks Ln in Dennis, MA is $1,906,300.
  • What is the price history for 16 Winding Oaks Ln?
    16 Winding Oaks Ln in Dennis, MA last sold for $945,975 in December 2019.
  • Is Dennis a buyer's or seller's market?
    Dennis is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Dennis?
    The median sale price in Dennis is $661K. That is up $20K from the prior month.
  • How big is the lot at 16 Winding Oaks Ln?
    The lot at 16 Winding Oaks Ln in Dennis, MA is about 0.46 acres (20,037 sq ft).
  • Does 16 Winding Oaks Ln have a garage?
    Yes, 16 Winding Oaks Ln in Dennis, MA has a garage.

Explore by feature - Air Conditioning

18 rentals with air conditioning in Dennis, MA

Explore by feature - Washer/dryer

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