44 Winthrop Dr, Riverside, CT 06878
OFF MARKET

44 Winthrop Dr
Riverside, CT 06878

Riverside
  • 5 Beds
  • 6 Baths
  • 7,700 sqft (on 0.40 acres)

$5,919,600

Trulia Estimate
as of Jun 8, 2026
Est. Refi. Payment $38,034/mo*
Refinance Your Home

$5,919,600

Trulia Estimate
as of Jun 8, 2026
Est. Refi. Payment $38,034/mo*
Refinance Your Home
5 Beds
6 Baths
7,700 sqft
(on 0.40 acres)

Local Information

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

Description

2012 stunning new residence crafted by noted local builder, this home is custom-built to perfection. Exceptional attention to detail is evident in the layout, millwork and materials including the stunning marble gourmet Kitchen & Waterworks Baths. From elegant formal rooms to the tranquil Master Suite; the stylish Family Room with its coffered ceiling or the full finished walk-out lower level featuring an additional entertainment space with fieldstone fireplace, exercise room, bedroom, spa-like full bath & fantastic storage or the bonus room on the third floor, no element has been overlooked.
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
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 44 Winthrop Dr

Interior Features

Interior Details
BasementAttic
Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: Shingle Not Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2012
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.40 acres

Price History for 44 Winthrop Dr

DatePriceEventSource
04/18/2013$3,875,000Sold
Greenwich MLS, Inc. #83630
02/05/2013$4,195,000PendingAgent Provided
12/27/2011$1,250,000Sold
N/A

Market trends in Greenwich

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.02M
$51.67KMoM
Sale-to-List Price
100.2%
0.1%MoM
Price per sq ft
$797
$11MoM
Available listings
191
45MoM
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Property Tax and Assessment

Year2025
Tax$31,264
Assessment$2,529,660
Home facts updated by county records

Comparable Sales for 44 Winthrop Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
18 Shoalpoint Ln, Riverside, CT
0.00
Single-Family Home
$6,525,000
07/01/25
5
6
5,702
52 Breezemont Ave, Riverside, CT
0.18
Single-Family Home
$4,780,000
10/17/25
6
6.5
5,970
4 Bramble Ln, Riverside, CT
0.11
Single-Family Home
$3,550,000
07/21/25
5
5
3,935
6 Dorchester Ln, Riverside, CT
0.21
Single-Family Home
$5,750,000
01/15/26
6
6
7,600
119 Hendrie Ave, Riverside, CT
0.34
Single-Family Home
$3,800,000
12/17/25
6
5.5
5,175
10 Lockwood Rd, Riverside, CT
0.26
Single-Family Home
$4,350,000
04/13/26
6
5.5
3,764
44 Bramble Ln, Riverside, CT
0.13
Single-Family Home
$4,300,000
05/01/26
4
4
4,212
32 Meyer Pl, Riverside, CT
0.21
Single-Family Home
$2,795,000
05/20/26
5
4.5
4,108
41 Winthrop Dr, Riverside, CT
0.29
Single-Family Home
$3,450,000
12/01/25
4
4.5
3,352
25 Dialstone Ln, Riverside, CT
0.35
Single-Family Home
$5,200,000
05/18/26
6
7
6,520

Nearby homes

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Assigned Schools

These are the assigned schools for 44 Winthrop Dr.
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

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

What Locals Say about Riverside

At least 47 Trulia users voted on each feature.

  • 92 % Say parking is easy

  • 91 % Say it's dog friendly

  • 90 % Say yards are well-kept

  • 89 % Say kids play outside

  • 89 % Say people would walk alone at night

  • 88 % Say they plan to stay for at least 5 years

  • 87 % Say car is needed

  • 86 % Say there's holiday spirit

  • 82 % Say it's quiet

  • 74 % Say neighbors are friendly

  • 74 % Say there's wildlife

  • 73 % Say there are sidewalks

  • 59 % Say it's walkable to restaurants

  • 56 % Say it's walkable to grocery stores

  • 53 % Say streets are well-lit

  • 52 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Sharon Elkayam
    "It is a friendly community where the kids ride bikes and play together. The schools are good. The kids play in the front yards. "
    0
    Flag
  • Trulia User
    "Very dog friendly. Lots of great places to walk with a dog. Many dog owners. The beach in Old Greenwich is a fun place to meet other dog owners and allow them to play."
    0
    Flag
  • Trulia User
    "I95 is the worst and the Merritt parkway are very difficult to commute on. Good luck if you need to commute during peak times. "
    1
    Flag
  • Sharonelkayam
    "Kid and pet friendly. Nice neighbors and well kept homes. The schools are great. Good area for walking and running. Near trains and shopping area in Old Greenwich. Beach is also a few minutes away."
    1
    Flag
  • Jesselynn G.
    "The elementary school fairs/carnivals, trick or treating, fireworks at the park nothing else in particular but overall a great neighborhood "
    0
    Flag
  • Rebecca
    "People r always out walking their dogs. Cars know they have the right of way and will either slow or go around completely "
    0
    Flag
  • Rebecca
    "Cozy neighborhood feel. Folks say hello when u walk past them. Lots of kids on bikes and dogs on leash"
    0
    Flag
  • Msuppodvm
    "Many special events around families and children. Many resources available for families and kids. Excellent afternoon programs, many sports programs. "
    0
    Flag
  • Mirielramos
    "I love my neighborhood is peaceful and quiet, nice place to live, and have all close by, bank, supermarket, drug stores etc"
    0
    Flag
  • Mcm.captiva@gmail.com
    "I see lots of dogs being walked. and responsible dog owners cleaning up after their dogs. Some owners having invisible fenced and didn't playing in yards. "
    0
    Flag
  • Mcm.captiva@gmail.com
    "neighborhood charity 10K runs. Church carnival. patriotic displays. fireworks in park. outdoors music."
    0
    Flag
  • Mcm.captiva@gmail.com
    "I take train to GCT and it is a short walk to METRO North. The commuter trains run very reliably and often."
    0
    Flag
  • Kimberly.kois
    "Very family friendly , sporty , safe , neighborhood with great access to public transportation, elementary schools, parks, playground , beach , Old Greenwich town"
    0
    Flag
  • Rebecca
    "Close to the water....can walk into town...kids walk or bike to school....unspoken neighborhood watch "
    8
    Flag
  • Sophiecoko
    "Living in a coastal neighborhood is really special. I love seeing the kids biking to the beach without jackets on ready to sail, kayak or paddle board."
    0
    Flag
  • dryfly7
    "Beautiful Dogwood Park Association, 3 minute walk to highly rated North Mianus Elementary School"
    0
    Flag

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44 Winthrop Dr, Riverside, CT 06878 is a 5 bedroom, 7 bathroom, 7,700 sqft single-family home built in 2012. 44 Winthrop Dr is located in Riverside, Riverside. This property is not currently available for sale. 44 Winthrop Dr was last sold on Apr 18, 2013 for $3,875,000. The current Trulia Estimate for 44 Winthrop Dr is $5,919,600.