27 Winding Brook Way, Middletown, NJ 07748
OFF MARKET

27 Winding Brook Way
Middletown, NJ 07748

  • 4 Beds
  • 2.5 Baths
  • 2,244 sqft (on 1 acre)

$905,800

Trulia Estimate
as of May 4, 2026
Est. Refi. Payment $5,684/mo*
Refinance Your Home

$905,800

Trulia Estimate
as of May 4, 2026
Est. Refi. Payment $5,684/mo*
Refinance Your Home
4 Beds
2.5 Baths
2,244 sqft
(on 1 acre)

Homes for sale near 27 Winding Brook Way

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Beautiful, 4 bedrm home/den/firplce/great rm/EIK/formal dining rm/oak floors.Large deck/patio/park like lawn. Lovely home sits high,overlooking surrounding property in desirable/quiet/private cul-de-sac. 1/2 mile to NJT & NY Waterway Ferry. 5 mi to GSP. Make this home your own! (Possible option for South Middletown H.S.)
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 27 Winding Brook Way

Interior Features

Interior Details
BasementNumber of Rooms: 9Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master BathCeiling Fan
Heating & Cooling
Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Brick, CompositionLawnPorch
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1965
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 27 Winding Brook Way

DatePriceEventSource
08/03/2015$452,500Sold
MoreMLS #21439567
03/31/2015$499,999PriceChange
Agent Provided
11/13/2014$549,000PriceChange
Agent Provided
10/03/2014$629,000Listed For SaleAgent Provided
11/06/1999$389,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$11,865
Assessment$721,300
Home facts updated by county records

Comparable Sales for 27 Winding Brook Way

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
28 Winding Brook Way, Middletown, NJ
0.03
Single-Family Home
$1,025,000
12/05/25
5
3.5
2,335
17 Winding Brook Way, Middletown, NJ
0.05
Single-Family Home
$950,000
02/13/26
4
2.5
2,072
8 Greenwood Place, Middletown, NJ
0.35
Single-Family Home
$730,000
10/03/25
4
3.5
2,272
5 Beth Drive, Middletown, NJ
0.52
Single-Family Home
$760,000
07/30/25
3
2.5
1,668
30 Packard Drive, Middletown, NJ
0.56
Single-Family Home
$985,000
11/24/25
3
2.5
2,133
21 The Trail, Middletown, NJ
0.28
Single-Family Home
$985,000
08/28/25
3
2.5
2,574
3 Green Oak Boulevard, Middletown, NJ
0.39
Single-Family Home
$1,380,000
01/30/26
4
2.5
2,896
14 Heath Pkwy, Middletown, NJ
0.80
Single-Family Home
$385,000
07/10/25
3
3
1,716
35 Michael Drive, Middletown, NJ
0.57
Single-Family Home
$975,000
08/27/25
4
3
3,249
24 Daniel Drive, Middletown, NJ
0.57
Single-Family Home
$925,000
06/30/25
5
3
2,758

Assigned Schools

These are the assigned schools for 27 Winding Brook Way.
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.

What Locals Say about Middletown

At least 158 Trulia users voted on each feature.

  • 91 % Say car is needed

  • 90 % Say it's dog friendly

  • 89 % Say parking is easy

  • 88 % Say there's holiday spirit

  • 85 % Say yards are well-kept

  • 77 % Say it's quiet

  • 77 % Say people would walk alone at night

  • 70 % Say kids play outside

  • 65 % Say they plan to stay for at least 5 years

  • 64 % Say neighbors are friendly

  • 64 % Say there are sidewalks

  • 61 % Say there's wildlife

  • 51 % Say streets are well-lit

  • 42 % Say there are community events

  • 37 % Say it's walkable to grocery stores

  • 36 % Say it's walkable to restaurants

Learn more about our methodology.
  • Bob Moge
    "Middletown is a very safe town with lots to offer. Great Shopping & Restaurant’s. I was born here then moved away for my trade in south Jersey and came back after I retired. "
    0
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  • Barb
    "We have many events throughout the year all over the area. The Twp is diverse and welcoming to all. "
    0
    Flag
  • Barb
    "It’s a great community to live, work and play in. Most neighbors have been here for decades and their children too. "
    0
    Flag
  • Jcar1124
    "Terrible, it is far, expensive and traffics filled. Mass transit exists but is not a great option, as it’s inconvenient "
    1
    Flag
  • Barb
    "People are dog friendly and at Halloween even the dogs trick or treat!! There is a dog park and off season the beach! "
    0
    Flag
  • Bob Moge
    "I am retired but I do go places all around where I live and there is easy access to go anywhere you want. But there are bad times of the day that can be very congested with work traffic."
    0
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  • Trulia User
    "Dog poop everywhere, nice people here and there but everyone has a dog and 25% of the people who do , do not pick up their dog poop. It’s disgusting. "
    0
    Flag
  • Trulia User
    "Very dog friendly neighborhood.Residents follow pet laws and curb and leash their dogs.Dog park available within driving distance."
    0
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  • Trulia User
    "I’ve lived here for a little over a year now. This area is a very pet friendly neighborhood. It seems as if everyone has a dog. Not much traffic on the block that we’re living on. Neighbor are all nice as well. Very kid friendly neighborhood as well. "
    3
    Flag
  • Trulia User
    "It’s a great neighborhood. Only thing, people don’t pick up their dog poop. Other than that, it’s great. Close to the city."
    0
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  • Trulia User
    "I work about 5 miles from my house so I don’t have that bad of a commute. Over all the traffic in this are going to NYC In the morning , as my husband does, is very easy. "
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  • Turlsworld14
    "The volunteer firefighters come around every CHRISTMAS Eve, Santa of course on one of the trucks, throwing candies to the kids . Middletown Day .. is a festival held every year, sort of like a small scale state fair. Memorial Day Parade every year, right up the road, this is a Historic District."
    1
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  • Matthew T. .
    "There are many dogs in the neighborhood which could be good or bad depending on your dogs temperament and demeanor. "
    0
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  • Darrius E. W.
    "Everything The people in Middletown and in Monmouth county are 95 percent great people, from the community to the store to the schools."
    0
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  • George F.
    "Great schools here in the community just not in Keansburg which is a disaster the homes are cheap there but at the loss of good education for your kids"
    0
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  • Dmonuski
    "Amazing school D’s, park system & neighborhoods. Love the wide open farms & nearby ocean. Only wish fewer out of state folks keep moving here - would prefer that most think NJ = oil refineries & the Turnpike "
    0
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  • Katie D. R.
    "Most neighbors have dogs and are constantly walking their dogs all around the neighborhoods and parks or the local dog park a few minutes away!"
    0
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  • John G.
    "Very good school district. Work with both children and parents to help the student move forward. Great community police program. "
    0
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  • Jmoyer1989
    "Perfect town for dog walking!! We always take our dog for walks, and you’ll always see other dog owners with their dogs. Tons of parks, as well, which couldn’t be better!"
    0
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  • Jenniferrosekreutzer
    "Quiet side streets, people are not zooming all over the place, there is a trail that you can walk your dog on that is paved and does not allow motorized vehicles "
    0
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  • John G.
    "Idk i dont get into things like that. We stay to ourselves. People around the area are nice and friendly. Good place to raise a family if your not from the northeast area its a good place to start or to settle down with a family "
    0
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  • Mike B.
    "There are a lot of busy streets, but there are also many neighborhoods with quiet roads. great area to raise a family."
    0
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  • Jeff F.
    "Middletoen is such a nice place to raise a family. Great people, great schools. Close to everything you could ever want or need."
    0
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  • Mike B.
    "This neighborhood is great for kids and and pets. great public transportation and parks. most neighbors are very nice."
    0
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  • Keith
    "Safe great town for commuting transportation and quick rides into city area... come check it out family and friends will love to visit. Always something to do"
    0
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  • Nllmoml
    "I’ve lived here for a few months during the process of my husband’s house being prepped for sale. This is a friendly and still quiet community where everybody shows respect for each other. Lots of shopping close by!!!!!"
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  • Lee Brewer
    "The Oak Hill Community is walkable to elementary, middle and high schools. We are walkable to the train station about 1.5 -3 miles via paved walkway. We are 15 minutes to many shorelines, and adjacent to a county park filled with trails, small playground and community history buildings. We are 4 miles to all types of shopping. We have an open, minor annual cost voluntary Association membership conducting many adult and children's activities throughout the year included in the $30 membership fee. These are excellent ways to mix and meet people. These are some of the many features of an excellent area called Oak Hill."
    0
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  • Laurie Wheeler
    "We know almost all of our neighbors and love them. We all look out for each other whenever anyone needs anything. Love "our village"."
    0
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  • Zani
    "A lot of people have dogs in the neighborhood. You see kids out walking their dogs all the time. People pick up after their dogs. "
    0
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  • Erin R.
    "Great place to commute from.....Easy access to trains, buses, and ferry. Easy to get to nyc........"..."
    0
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  • Joseph L.
    "Quiet. Takes me 45 min to an hour. I drive up 36 to Texas RD. Or just use rt 18. The traffic isn’t bad at all "
    0
    Flag
  • Nicole F.
    "great stores, easy access to highways, close to the beach, convenient train station, good food and bars "
    2
    Flag
  • monika o.
    "I’ve lived here for 5 years and love it. Wouldint want to be anywhere else. It is quiet and my neighbors are great."
    0
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  • Ecrn65
    "Middletown is a wonderful neighborhood,from the wonderful neighbors great near by restaurants and entertainment in red Bank and Beyond and beautiful parks and great schools lots of nature both flora and fauna! "
    1
    Flag
  • Ajwireman
    "everything you need is here and very local with nice people.shopping areas and parking are o plenty full and clean "
    0
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Homes for rent near 27 Winding Brook Way

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Off Market Homes Near 27 Winding Brook Way

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27 Winding Brook Way, Middletown, NJ 07748 is a 4 bedroom, 3 bathroom, 2,244 sqft single-family home built in 1965. This property is not currently available for sale. 27 Winding Brook Way was last sold on Aug 3, 2015 for $452,500. The current Trulia Estimate for 27 Winding Brook Way is $905,800.