OFF MARKET

Off market jan 2024 for $2.6M

$3,428,706

Est. refi paymentEst. refi $17,792/mo

•

5,185

sq ft

29 Winding Way, Little Silver, NJ 07739

About this home

Nestled in the highly sought-after Winding Way neighborhood, this impeccable 5,000+ square foot home is the epitome of luxury living. Meticulously maintained and thoughtfully designed, this residence offers a perfect blend of elegance and comfort. Upon entering, you'll be greeted by a two story foyer, exquisite craftsmanship and an abundance of natural light. With its well appointed and versatile layout, this 4-bed, 5.1 bath home boasts a beautiful gourmet kitchen opening to a vaulted ceiling family room, formal dining room, large home office, workout/ playroom and spacious laundry room. Second floor features include expansive primary bedroom and bath with walk in closet accompanied by three additional large bedrooms and 2 full baths. Outdoor living at its finest, this magnificent oasis is meticulously well kept with lush landscaping and privacy. Entertainers will love the blue stone patio complete with fireplace, Viking grill, salt water pool and spa and its stunning adjacent pool house with wet bar, HVAC, full bath and laundry room. Additional features of this remarkable home include a full house generator, wine closet, oversized 2 car garage, and plenty of storage! It's worth noting this house was untouched by Hurricane Sandy's floodwaters. With a host of amenities, it's excellent school system and it's close proximity to local beaches, Red Bank, and NJ transit, don't miss the opportunity to make this exceptional property your own!

Single-familyProperty Type

2009Year Built

1.29 acresLot Size

$661Est. Price/Sq.Ft.

2 car garageParking

Listed by Mike Shaheen • O'Brien Realty, LLC

Bought with Mike Shaheen • O'Brien Realty, LLC

Redfin checked: 2 minutes ago

•Source:MOMLS #22328199

Redfin Estimate

$3,428,706

$730K since sold in January 2024$9,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 40.1% higher than the average sale price ($2.45M) of 6 comparable homes.

SOLD SEP 24, 2026
$2,220,000
A
4 beds3 baths4,472 sq ft
573 Prospect Ave, Little Silver, NJ 07739
SOLD NOV 6, 2026
$2,550,000
B
5 beds4.5 baths3,243 sq ft
5 Pirates Cove Rd, Little Silver, NJ 07739
SOLD OCT 1, 2026
$2,599,000
C
5 beds5 baths5,270 sq ft
94 N Mitchell Pl, Little Silver, NJ 07739
SOLD JUL 30, 2026
$3,250,000
D
4 beds3.5 baths— sq ft
181 Rumson Rd, Rumson, NJ 07760
SOLD NOV 22, 2025
$2,585,000
E
4 beds4.5 baths— sq ft
82 Sunnybank Dr, Shrewsbury, NJ 07702
SOLD OCT 1, 2026
$1,475,000
F
4 beds3 baths2,200 sq ft
47 Monroe Ave, Little Silver, NJ 07739

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Earn from this home

Sell

$1,184,814

Est. take-home

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Refinance

Est. cash available

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Rent

$4,425/mo

Redfin rental estimate

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Market trends in 07739, NJ

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

102.3%

2.4% MoM

Median sale price

$991K

$44K MoM

Avg. days on market

14d

1 days MoM

Recently sold homes

1 MoM

New listings for sale

OPEN TODAY, 12PM TO 2PM
$999,999
3 beds2 baths1,794 sq ft
37 Maple Ave, Little Silver, NJ 07739
See all

Provided by Redfin

Sale history for 29 Winding Way

Year

Property tax

Land + Additions

Assessment*

2025

$38,605 (+1.8%)

$986,800 + $1,963,200

$2,950,000

2024

$37,929 (+19.1%)

$939,700 + $1,746,800

$2,686,500

2023

$31,842 (+8.0%)

$573,100 + $1,673,900

$2,247,000

2022

$29,471

$473,100 + $1,295,900

$1,769,000

2021

$29,460 (−1.6%)

$373,100 + $1,246,200

$1,619,300

2020

$29,953 (−4.8%)

$373,100 + $1,119,300

$1,492,400

2019

$31,468 (+3.3%)

$373,100 + $1,104,600

$1,477,700

2018

$30,470 (+0.9%)

$373,100 + $1,208,200

$1,581,300

2017

$30,202 (+2.5%)

$373,100 + $1,131,000

$1,504,100

2016

$29,464 (−5.8%)

$373,100 + $1,131,000

$1,504,100

2015

$31,272 (+3.8%)

$373,100 + $1,112,000

$1,485,100

2014

$30,134 (+6.4%)

$343,100 + $1,058,500

$1,401,600

2013

$28,319 (+5.0%)

$343,100 + $1,058,500

$1,401,600

2012

$26,962 (+3.2%)

$308,800 + $953,200

$1,262,000

2011

$26,121 (+418.3%)

$223,100 + $913,100

$1,136,200

2010

$5,040 (+7.2%)

$223,100 + $913,100

$1,136,200

2009

$4,701

$223,100

Tax history for 29 Winding Way

Year

Property tax

Land + Additions

Assessment*

2025

$38,605 (+1.8%)

$986,800 + $1,963,200

$2,950,000

2024

$37,929 (+19.1%)

$939,700 + $1,746,800

$2,686,500

2023

$31,842 (+8.0%)

$573,100 + $1,673,900

$2,247,000

2022

$29,471

$473,100 + $1,295,900

$1,769,000

2021

$29,460 (−1.6%)

$373,100 + $1,246,200

$1,619,300

2020

$29,953 (−4.8%)

$373,100 + $1,119,300

$1,492,400

2019

$31,468 (+3.3%)

$373,100 + $1,104,600

$1,477,700

2018

$30,470 (+0.9%)

$373,100 + $1,208,200

$1,581,300

2017

$30,202 (+2.5%)

$373,100 + $1,131,000

$1,504,100

2016

$29,464 (−5.8%)

$373,100 + $1,131,000

$1,504,100

2015

$31,272 (+3.8%)

$373,100 + $1,112,000

$1,485,100

2014

$30,134 (+6.4%)

$343,100 + $1,058,500

$1,401,600

2013

$28,319 (+5.0%)

$343,100 + $1,058,500

$1,401,600

2012

$26,962 (+3.2%)

$308,800 + $953,200

$1,262,000

2011

$26,121 (+418.3%)

$223,100 + $913,100

$1,136,200

2010

$5,040 (+7.2%)

$223,100 + $913,100

$1,136,200

2009

$4,701

$223,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

Baths

Stories

—

Lot width

138 ft.

Lot depth

267 ft.

Lot size

0.85 Acres

Year renovated

—

Sq. Ft.

5,643

Year built

2009

Style

Single Family Residential

County

Monmouth County

APN

2500059 00026

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 16, 2026.

Property details

Parking

Parking Information
Garage: Yes
Garage Spaces: 2.0
Attached Garage: Yes

Interior

Interior Features
Inclusions: Blinds/Shades, Generator
Fireplace: Yes
Fireplaces Total: 0

Heating & Cooling
Heating: Yes
Forced Air, 3+ Zoned Heat
Cooling: Yes
Multi Units, 3+ Zoned AC

Bedroom Information
Bedrooms Total: 4

Bathroom Information
Bathrooms Total Integer: 6
Bathrooms Total Decimal: 5.5
Bathrooms Full: 5
Bathrooms Half: 1

Basement Information
Basement: Crawl Space

Exterior

Exterior Features
Shingle

Property Information
Living Area: 5185.0
Ownership: Fee Simple

Building Information
Stories Total: 2

Subdivision Information
None
None
Little Silver (LIT)

Financial

Tax Information
Parcel Number: 25-00059-0000-00026
Tax Annual Amount: 29471.0
Tax Assessed Value: 1769000
Tax Block: 59
Tax Lot: 26
Tax Year: 2022

Utilities

Utility Information
Sewer: Public Sewer

Location

Location Information
Monmouth
Latitude: 40.33087
Longitude: -74.031858

Public facts

Beds: 4
Baths: 5.0
Sq. Ft.: 5,643
Stories: —
Lot Size: 0.85 acres
Style: Single Family Residential
Year Built: 2009
Year Renovated: —
County: Monmouth County
APN: 2500059 00026

Home facts updated by county records on Sep 16, 2026

Other

Documents & Disclosures
Documents Change Timestamp: 2023-10-09T20:43:53.000Z
Documents Count: 0

Listing Information
Photos Count: 65
Closed

Around this home

Schools

K - 12
Preschool & daycare

Point Road School

Public PreK-4 • Assigned • 0.3mi

9/10

Markham Place Elementary School

Public 5-8 • Assigned • 0.8mi

9/10

Red Bank Regional High School

Public 9-12 • Assigned • 1.4mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

4/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

7/10 Heat Factor

7 days above 94° expected this year, 16 days in 30 years

8/10 Wind Factor

80% chance of strong winds in next 30 years

3/10 Air Factor

3 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Little Silver, NJ • 07739

Average low and high temperatures (°F)

37°

24°

40°

27°

55°

38°

63°

46°

70°

55°

81°

65°

85°

71°

79°

65°

75°

63°

65°

52°

57°

42°

43°

29°

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.6 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.26M – $3.94M

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Home values near 29 Winding Way

Data from public records.

Address	Redfin Estimate
44 Winding Way, Little Silver, NJ 5 Beds \| 4.5 Baths \| 4367 Sq. Ft.	$2,603,084
8 Winding Way, Little Silver, NJ 5 Beds \| 3.5 Baths \| - Sq. Ft.	$2,737,745
20 Winding Way, Little Silver, NJ 4 Beds \| 3 Baths \| 2480 Sq. Ft.	$1,849,618
38 Winding Way, Little Silver, NJ 5 Beds \| 4 Baths \| 4200 Sq. Ft.	$2,617,019
45 Winding Way, Little Silver, NJ 4 Beds \| 2.5 Baths \| - Sq. Ft.	$2,454,740
41 Winding Way, Little Silver, NJ 3 Beds \| 2 Baths \| 2044 Sq. Ft.	$1,399,910
30 Westwood Road, Little Silver, NJ 3 Beds \| 2 Baths \| - Sq. Ft.	$1,328,182

Address	Redfin Estimate
52 Winding Way, Little Silver, NJ 4 Beds \| 3 Baths \| 3103 Sq. Ft.	$1,726,608
12 Winding Way, Little Silver, NJ 4 Beds \| 2.5 Baths \| 2850 Sq. Ft.	$2,119,918
26 Winding Way, Little Silver, NJ 4 Beds \| 4 Baths \| 3102 Sq. Ft.	$2,247,368
25 Winding Way, Little Silver, NJ 4 Beds \| 4 Baths \| 4024 Sq. Ft.	$2,824,578
49 Winding Way, Little Silver, NJ 5 Beds \| 3.5 Baths \| 4200 Sq. Ft.	$2,522,492
33 Winding Way, Little Silver, NJ 5 Beds \| 4 Baths \| - Sq. Ft.	$2,580,251
36 Westwood Road, Little Silver, NJ 6 Beds \| 3.5 Baths \| 3576 Sq. Ft.	$1,914,495

Address	Redfin Estimate
56 Winding Way, Little Silver, NJ 5 Beds \| 5 Baths \| 4582 Sq. Ft.	$2,297,667
16 Winding Way, Little Silver, NJ 5 Beds \| 4.5 Baths \| 3578 Sq. Ft.	$2,459,761
32 Winding Way, Little Silver, NJ 4 Beds \| 2 Baths \| 2549 Sq. Ft.	$1,515,811
19 Winding Way, Little Silver, NJ 4 Beds \| 2 Baths \| 2652 Sq. Ft.	$1,767,171
35 Winding Way, Little Silver, NJ 4 Beds \| 2 Baths \| 2976 Sq. Ft.	$1,775,992
26 Westwood Road, Little Silver, NJ 3 Beds \| 3 Baths \| 2549 Sq. Ft.	$1,644,098
5 Westwood Court, Little Silver, NJ 4 Beds \| 2 Baths \| 2438 Sq. Ft.	$1,375,303

Property information provided by MOMLS when last listed in 2023. This data may not match . Learn more.

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