44 Upper Cross Rd, Greenwich, CT 06831
Property image
Property image
OFF MARKET

$12,509,700

Trulia Estimate
  • 5 Beds
  • 7 Baths
  • 7,000 sqft (on 12 acres)

44 Upper Cross Rd, Greenwich, CT 06831

Est. Refi. Payment $83,872/mo*
Refinance Your Home
Currently Off Market - Sold Dec 6, 2012 for $8,000,000

Home Value

Trulia Estimate
$12.5M
Since last month
Decreased$279K (-2.3%)
Since last year
Increased$1M (+10.7%)
Since last sale
Increased$4M (+51.1%)
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 +121% in the last 10 years
MonthEstimated value
2026
September 2026$12.09M
August 2026$12.51M
July 2026$12.36M
June 2026$12.28M
May 2026$12.11M
April 2026$11.72M
March 2026$11.73M
February 2026$11.38M
January 2026$11.24M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
900 North St, Greenwich, CT
0.54
Single-Family Home
$5,995,000
07/02/26
4
5
8,563
21 Aiken Rd, Greenwich, CT
1.01
Single-Family Home
$6,200,000
12/12/25
5
5
6,714
868 North St, Greenwich, CT
0.72
Single-Family Home
$4,600,000
03/27/26
5
6
5,040
22 Partridge Hill Ln, Greenwich, CT
0.91
Single-Family Home
$8,355,000
07/13/26
5
9
8,932
828 North St, Greenwich, CT
0.82
Single-Family Home
$7,950,000
10/06/25
6
8.5
9,600
24 Conyers Farm Dr, Greenwich, CT
0.51
Single-Family Home
$23,000,000
10/30/25
6
9
12,312
577 Round Hill Rd, Greenwich, CT
1.14
Single-Family Home
$7,500,000
01/22/26
4
5.5
8,188
11 Conyers Farm Dr, Greenwich, CT
0.65
Single-Family Home
$14,833,500
11/17/25
7
12
16,597
6 Reynwood Mnr, Greenwich, CT
1.05
Single-Family Home
$4,350,000
05/01/26
5
5.5
5,670
979 Lake Ave, Greenwich, CT
0.72
Single-Family Home
$2,570,000
02/02/26
5
4.5
3,975

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
111 Conyers Farm Dr, Greenwich, CT 06831
0.23
$16,781,000
6
11
14,284
Off Market
25 Upper Cross Rd, Greenwich, CT 06831
0.34
-
-
-
-
Off Market
15 Upper Cross Rd, Greenwich, CT 06831
0.42
$10,707,300
6
7
10,346
Off Market
1068 Lake Ave, Greenwich, CT 06831
0.46
$7,729,700
5
7.5
12,680
Off Market
909 North Street, Greenwich, CT 06831
0.49
$3,658,300
10
6
13,312
Off Market
24 Conyers Farm Dr, Greenwich, CT 06831
0.51
$24,664,100
6
9
12,312
Off Market
1046 Lake Ave, Greenwich, CT 06831
0.50
$6,306,200
5
8.5
11,323
Off Market
900 North St, Greenwich, CT 06831
0.54
$5,995,000
4
5
8,563
Recently Sold
993 Lake Ave, Greenwich, CT 06831
0.62
$3,500,000
5
5.5
4,862
For Sale
11 Conyers Farm Dr, Greenwich, CT 06831
0.65
$14,833,500
7
12
16,597
Recently Sold
3 Hekma Rd, Greenwich, CT 06831
0.65
$13,421,000
7
8.5
9,174
Off Market
7 Mountain Laurel Dr, Greenwich, CT 06831
0.64
$3,933,100
5
5.5
4,680
Off Market

Local Information

  • Map ViewExplore the area around 44 Upper Cross Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1986
12 acre lot
7,000 sqft
$1,787/sqft
Garage

About this House

Located at one of the most prestigious addresses in Greenwich and trumped by its location in exclusive Conyers Farm, known for white board fences, polo fields and grand 10 plus acre estates, this stone and clapboard home designed by Robert Lamb Hart, is on the largest parcel of land currently on the market in Conyers Farm. A long stately drive leads to the 23 bucolic acres comprised of rolling lawns and woodlands which have been subdivided into two parcels and offer an exceptional opportunity for an additional home or guest house/ compound. Classical and traditional owning this home affords one the opportunity to enjoy and assume a lifestyle of grand understated elegance. The Sun lit west facing home with 12 acres is currently available for 5,990,000 and 10 acres of flat beautiful pastoral land for 3,750,000.
44 Upper Cross Rd, Greenwich, CT 06831 is a 5 bedroom, 7 bathroom, 7,000 sqft single-family home built in 1986. It last sold for $8,000,000 on Dec 6, 2012. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $12,509,700.

Home Details for 44 Upper Cross Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 12
Heating & Cooling
Heating: Forced AirAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: SlateDeckExterior: Stucco, Brick
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1986Year Updated: 1990
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 12.00 acres

Price and Tax history

DateEventPrice
Dec 6, 2012
Source: N/A
Sold
$8,000,000
Sep 13, 2012
Source: Agent Provided
PriceChange
$4,995,000
Price decreased by 4%
Jun 2, 2012
Source: Agent Provided
PriceChange
$5,199,000
Price decreased by 5%
Nov 1, 2011
Source: Agent Provided
PriceChange
$5,495,000
Price decreased by 3%
Oct 14, 2011
Source: Agent Provided
PriceChange
$5,690,000
Price decreased by 5%

Market trends in Greenwich

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.58M
$150KMoM
Sale-to-List Price
104.8%
1.0%MoM
Price per sq ft
$825
$1MoM
Available listings
152
30MoM

Around this home

What Locals Say about Greenwich

At least 470 Trulia users voted on each feature.

  • 88 % Say it's dog friendly

  • 83 % Say car is needed

  • 77 % Say parking is easy

  • 76 % Say there's holiday spirit

  • 74 % Say people would walk alone at night

  • 73 % Say yards are well-kept

  • 69 % Say kids play outside

  • 67 % Say it's walkable to restaurants

  • 67 % Say they plan to stay for at least 5 years

  • 67 % Say it's quiet

  • 60 % Say there are sidewalks

  • 60 % Say there's wildlife

  • 58 % Say neighbors are friendly

  • 57 % Say streets are well-lit

  • 55 % Say it's walkable to grocery stores

  • 45 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Dog friendly"
    0
    Flag
  • Trulia User
    "Great long walking trails all Over the town, and dog parks! So it is just wonderfully dog friendly. "
    0
    Flag
  • Justine
    "Greenwich car show, dog day out, Bruce museum, proximity to Highway, public beach and pool for Greenwich residents"
    0
    Flag
  • Trulia User
    "School events, country club, cohen civic center, beach, walk-to-town, nice holiday environments, nice neighbors and neighborhoods!"
    0
    Flag
  • Dalvesbrito
    "Block party School Halloween party School movie party Fireworks on 4th of July Center civic events "
    0
    Flag
  • Kellysgreensllc
    "There are good schools,parks,library here. Conveniently located near mass transit.Not to forget our beaches. Local restaurants "
    0
    Flag
  • eiji.nishimuras
    "No good dog park to speak of. And generally park regulation and beach regulation is not very dog friendly "
    0
    Flag
  • 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
  • Jp
    "It’s the best blend of good suburban town systems and support, and easy access to the center of economic opportunity and culture. "
    0
    Flag
  • Stefanie Lacoff, Realtor
    "Many parks and trails to walk your dog. Dogs are allowed at the beach during winter months. Greenwich is a great place to live! "
    1
    Flag
  • Stefanie Lacoff, Realtor
    "Greenwich is diverse and inclusive. People are educated and parents are involved. We have great amenities and resources for our community. "
    0
    Flag
  • Stefanie Lacoff, Realtor
    "Greenwich is a fantastic town to live in and raise a family. It’s great for all ages from kids through seniors. "
    0
    Flag
  • Jmcdg22m5w
    "It’s a quiet and clean neighborhood, I like it a lot. The restaurants are beautiful, the people are friendly, it is an easily accessible place for pharmacies or clothing and accessories stores."
    0
    Flag
  • Trulia User
    "I’ve lived here 25 years and love it. Looking to stay in the area only need a bigger house with no steps."
    1
    Flag
  • Trulia User
    "Great neighborhood! Love it here just looking for something more private single family home on a dead end or curl de sac."
    2
    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
  • Sandra
    "Halloween decoration is the best! Neighbors are very nice and safety, kids walk and play safety school is very good"
    0
    Flag
  • Barbara J.
    "Great public and private schools and safe neighborhoods. People are friendly and it’s a great place to raise kids. "
    5
    Flag
  • Charles M.
    "Pretty perfect. Train, buses, the parkway and 95. What’s left? Car pooling! and we have that as well."
    0
    Flag
  • Janette S. A.
    "Family oriented neighborhood with nice parks and sidewalk restaurants. Feel safe going for a walk and at the park. "
    0
    Flag
  • Diane L.
    "The police involvement with their community, the amazing schools and circular activities, the friendly neighborhood, so many other Positive things to say not enough time!"
    4
    Flag
  • Hercoles_silveir4
    "Grande offers better security public transport schools hospital than any other city that my family and I have ever lived in I think a good place to live would recommend to anyone that I like a safe and educated home"
    1
    Flag
  • Daniel C.
    "I need a car most of the time. There’s 2 buses line that serves the town, one takes you to the metro north station "
    0
    Flag
  • Trevor M.
    "Love living here!! It is beautiful,safe and fun. Tods point is amazing. Great schools and plenty of things to do!"
    0
    Flag
  • Leila
    "The is very. Nice friendly I like to live in Grreewich because is Quite and gentle I can walk to my dog in the nighttime no danger"
    5
    Flag
  • Lynn M.
    "Busy street traffic, leash mandatory , people drive by fast! Dogs being walked are friendly. People pick up their dog waste. It’s a plus!"
    1
    Flag
  • Allforsummer
    "I grew up in Glenville. It’s a very family oriented neighborhood. Local businesses are owned by neighbors. Kids can ride their bikes freely or take walks to Glenville Pizza. Great place to live! "
    0
    Flag
  • Katetaylor83
    "Yes - there are a number of places close by to walk your dogs. It’s not ideal, as there aren’t a lot of off leash options and the dog run is tiny and unusable. "
    3
    Flag
  • Ksziman
    "Strong sense of community and neighborly support and camaraderie. Folks generally look out for one another "
    3
    Flag
  • Stephanie
    "Yes there are lots of dogs. With lots of parks to walk dogs. Anyone who has a dog would be comfort in. "
    0
    Flag
  • Lynn M.
    "My area is not particularly family friendly. I live in the main avenue. Better suited to working person/s."
    2
    Flag
  • Lesliegodner
    "I’ve lived here for a year. It’s a great neighborhood. We have amazing restaurants and stores. Great for families and singles alike. "
    0
    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
  • Mdandola
    "Lots of families in the area and great schools. The town has tons of wonderful programs, and there are great additional programs through YMCA and other organizations in town. The town party is awesome, as well."
    4
    Flag
  • Sarah G.
    "I reverse commute to North Haven—50 mikes away. I have zero traffic and can get to 95 quickly, so that’s a plus. "
    0
    Flag
  • Andrea T.
    "Is very safe has great schools clean streets is near most shops people respect each other I would love rents to be not as expensive forces people to move out "
    0
    Flag
  • Gissella E.
    "Safe area to live. Great school with a exceptional , espectacular kids activities and kids friendly and pleasure to live here and grow up your family. Good , good ,good "
    0
    Flag
  • Debtifrob
    "This community is as close as you can get to a home town like Father Knows Best or Andy Griffin. With. the exception of the high cost, it's a very warm, exclusive neighborhood with mansions & working class ppl. lots of celebrities move here bc if safety & school system. I was born here & living here 65yrs now. Downfall is the high housing, upside lots if culture & a few beaches, public pool & island a ferry brings you to."
    4
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 44 Upper Cross Rd

  • What is 44 Upper Cross Rd estimated to be worth?
    Trulia's estimated value for 44 Upper Cross Rd in Greenwich, CT is $12,509,700.
  • What is the price history for 44 Upper Cross Rd?
    44 Upper Cross Rd in Greenwich, CT last sold for $8,000,000 in December 2012.
  • Is Greenwich a buyer's or seller's market?
    Greenwich is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Greenwich?
    The median sale price in Greenwich is $2.58M. That is up $150K from the prior month.
  • Does 44 Upper Cross Rd have a pool?
    Yes, 44 Upper Cross Rd in Greenwich, CT has a pool.
  • How big is the lot at 44 Upper Cross Rd?
    The lot at 44 Upper Cross Rd in Greenwich, CT is about 12 acres.

Explore by feature - Pet Friendly

33 pet-friendly rentals in Greenwich, CT

Explore by feature - Garage

51 rentals with a garage in Greenwich, CT

Explore by feature - Air Conditioning

118 rentals with air conditioning in Greenwich, CT

Explore by feature - Pool

16 rentals with a pool in Greenwich, CT

Explore by feature - Washer/dryer

95 rentals with a washer/dryer in Greenwich, CT

Explore by feature - Outdoor Space

19 rentals with an outdoor space in Greenwich, CT

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 44 Upper Cross Rd

Skip to last item
Skip to first item

Homes for sale near 44 Upper Cross Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item