Is a car needed in Upton, MA?

As of early 2026, 94% of users say car is needed

Is parking easy in Upton, MA?

As of early 2026, 88% of users say parking is easy

Are yards well-kept in Upton, MA?

As of early 2026, 83% of users say yards are well-kept

Is Upton, MA dog-friendly?

As of early 2026, 75% of users say it's dog friendly

Would people walk alone at night in Upton, MA?

As of early 2026, 73% of users say people would walk alone at night

Is there wildlife in Upton, MA?

As of early 2026, 71% of users say there's wildlife

Do residents of Upton, MA plan to stay at least 5 years?

As of early 2026, 68% of users say they plan to stay for at least 5 years

Does Upton, MA show holiday spirit?

As of early 2026, 67% of users say there's holiday spirit

As of early 2026, 66% of users say it's quiet

Are neighbors friendly in Upton, MA?

As of early 2026, 60% of users say neighbors are friendly

Do kids play outside in Upton, MA?

As of early 2026, 59% of users say kids play outside

Does Upton, MA have sidewalks?

As of early 2026, 48% of users say there are sidewalks

Are there community events in Upton, MA?

As of early 2026, 30% of users say there are community events

Are the streets well-lit in Upton, MA?

As of early 2026, 25% of users say streets are well-lit

Is Upton, MA walkable to restaurants?

As of early 2026, 17% of users say it's walkable to restaurants

Is Upton, MA walkable to grocery stores?

As of early 2026, 13% of users say it's walkable to grocery stores

What is 22 Jackson Dr #66 estimated to be worth?

Trulia's estimated value for 22 Jackson Dr #66 in Upton, MA is $595,900 .

What is the price history for 22 Jackson Dr #66?

22 Jackson Dr #66 in Upton, MA last sold for $492,645 in October 2021.

Is Upton a buyer's or seller's market?

Upton is currently a seller's market, based on recent for-sale activity.

What do residents say about Upton?

Residents describe Upton, MA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Upton, MA .

Does 22 Jackson Dr #66 have air conditioning?

Yes, 22 Jackson Dr #66 in Upton, MA has air conditioning.

Does 22 Jackson Dr #66 have parking?

Yes, 22 Jackson Dr #66 in Upton, MA has on-site parking.

OFF MARKET

22 Jackson Dr #66
Upton, MA 01568

2 Beds
2 Baths
1,656 sqft

$595,900

Trulia Estimate

as of Aug 11, 2026

Est. Refi. Payment $3,713/mo*

Refinance Your Home

$595,900

Trulia Estimate

as of Aug 11, 2026

Est. Refi. Payment $3,713/mo*

Refinance Your Home

2 Beds

2 Baths

1,656 sqft

Local Information

Map ViewExplore the area around 22 Jackson Dr #66.
Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Condo

Year Built

2021

Living Area

1,656 sqft

Price/Sqft

$360

About this House

New Construction in Upton Ridge, a 55+ community. This popular Trentino is a single story, end unit home with an open floor plan and a beautiful bay window in the dining area. It's the perfect home for entertaining with a gourmet kitchen, lots of upgraded cabinets and an oversized island. The Gathering Room is spacious and open to the kitchen and dining area. The Owner's suite boasts a tile shower bathroom and walk in closet. 2nd Bedroom and Den with French doors complete this thoughtfully designed one story living floor plan. Price reflects location and beautiful upgrades. Convenient to Boston, Providence, N.H and easy access to Rt. 9, 90, 495, 146 and the commuter rail. Play a round of golf at nearby Shining Rock Golf Course. Enjoy low maintenance living backed by a 10 Year Warranty.

22 Jackson Dr #66, Upton, MA 01568 is a 2 bedroom, 2 bathroom, 1,656 sqft condo built in 2021. It last sold for $492,645 on Oct 12, 2021. It is currently off market. The Trulia Estimate is $595,900, with a rent estimate of $3,228/month.

Home Details for 22 Jackson Dr #66

Interior Features
Heating & Cooling Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities Cable ReadyDishwasherMicrowave
Levels, Entrance, & Accessibility Floors: Tile, Carpet, Hardwood

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: Vinyl
Parking & Garage Parking Spaces: 2

Property Information
Year Built Year Built: 2021
Property Type / Style Property Type: Condo

Community
Units in Building: 139

Additional Information
Fifty Five Plus Active Community

Price History for 22 Jackson Dr #66

Date	Price	Event	Source
10/12/2021	$492,645	Sold	MLS PIN #72773137
Recording Date 10/12/2021 County Transfer Tax N/A Total Transfer Tax N/A
01/19/2021		ListingRemoved	MLS PIN

01/09/2021	$509,995	Listed For Sale	Agent Provided

Market trends in Upton

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Skip to last item

Results are loading

Skip to first item

Comparable Sales for 22 Jackson Dr #66

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
8 Jackson Dr #8, Upton, MA	0.05	Condo	$720,000	06/29/26	2	3	2,214
61 Tulip Cir, South Grafton, MA	1.04	Condo	$435,000	12/16/25	3	3	1,380
89 Buttercup Ln, South Grafton, MA	1.04	Condo	$560,000	01/21/26	3	3	2,175
135 Church Ave, Northbridge, MA	0.78	Condo	$275,000	12/22/25	3	1	900
35 School St #35, Northbridge, MA	0.89	Condo	$275,000	04/01/26	3	1	1,067
16 Fieldstone St, Upton, MA	1.97	Condo	$439,900	10/02/25	2	2	1,666
84 Mikes Way #84, Northbridge, MA	1.71	Condo	$659,900	12/12/25	3	2.5	2,783
51 School St #3, Upton, MA	2.02	Condo	$410,000	07/31/26	3	2	1,420
6 Fieldstone St, Upton, MA	1.94	Condo	$439,500	05/08/26	1	2	1,699
73 Plummer Ave #73, Whitinsville, MA	2.18	Condo	$585,000	03/02/26	3	2	1,535

Nearby homes

Get a sense of prices in the area by checking nearby homes.

Skip to last item

OFF MARKET
2 bd
2.5 ba
2,121 sqft
42 Sienna Cir #5214,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
2 bd
2 ba
1,656 sqft
44 Sienna Cir #5116,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
Est. $653,100
2 bd
3 ba
1,656 sqft
31 Sienna Cir #3712,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
2 bd
2 ba
1,656 sqft
59 Shannon Way #59,
Upton, MA 01568
TEAM Metrowest, Berkshire Hathaway HomeServices Commonwealth Real Estate
OFF MARKET
2 bd
3 ba
1,656 sqft
50 Sienna Cir #4815,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
2 bd
2 ba
1,510 sqft
46 Sienna Cir #5015,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
FOR SALE
$709,000
2 bd
2.5 ba
1,950 sqft
56 Shannon Way #56,
Upton, MA 01568
The Semple & Hettrich Team, Coldwell Banker Realty - Sudbury
OFF MARKET
2 bd
2 ba
1,510 sqft
54 54/107 Shannon Way #10730,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
2 bd
3 ba
1,656 sqft
58 Shannon Way #105,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
Est. $698,100
2 bd
2.5 ba
2,160 sqft
56 Shannon Way #10630,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
2 bd
2.5 ba
2,300 sqft
48 Sienna Cir #4915,
Upton, MA 01568
Erin Sullivan, Pulte Homes of New England
OFF MARKET
2 bd
2 ba
1,500 sqft
7 Sienna Cir #7,
Upton, MA 01568
Shelly A. Armstrong, Redfin Corp.

Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 22 Jackson Dr #66.

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 Upton

At least 28 Trulia users voted on each feature.

94 % Say car is needed
88 % Say parking is easy
83 % Say yards are well-kept
75 % Say it's dog friendly
73 % Say people would walk alone at night
71 % Say there's wildlife
68 % Say they plan to stay for at least 5 years
67 % Say there's holiday spirit
66 % Say it's quiet
60 % Say neighbors are friendly
59 % Say kids play outside
48 % Say there are sidewalks
30 % Say there are community events
25 % Say streets are well-lit
17 % Say it's walkable to restaurants
13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Fernando M.
Resident
5y ago
"I've lived in Upton now for almost a Decade and it's an amazing town. The community is amazing, people are respectful, lots of community events, lots of recreational areas from Kiwanis beach, Upton State Park, Peppercorn Hill Conservation Area and other location, the schools are excellent, teachers care about the students, great academic and athletic departments. Upton truly is a place you can raise a family and feel safe."
0
Flag
Kristy G. B.
Resident
6y ago
"Must leave early to get to Boston or Boston area. Early is 6:30 or leave after 9 am. There is a lot of traffic going East, but is going on the other direction not as bad. There is not a lot of traffic on the town, but on the boarders of all surrounding towns there is traffic at peak hours."
7
Flag
Kristy G. B.
Resident
6y ago
"We’ve lived here for 9 years and everyone is very friendly and looks out for each other, yet you maintain your privacy. It’s a great sense of community with lots of young families."
1
Flag
Bapalladini
Visitor
6y ago
"it's a nice area. my dad loves it here. nice neighborhood, good community. old time feel to the area. plenty of hiking, parks etc. good schools, overall great "
2
Flag
Kristy G. B.
Resident
6y ago
"Safe, tight knit community where everyone is looking out for each other. The community is growing and young families are moving in. It definitely has a small town feel. "
2
Flag
Lily G.
Resident
6y ago
"plenty of parks to walk dogs. big yards and land for dogs to play and have space. close to tuffs animal hospital. "
1
Flag
Paola W. O.
Resident
6y ago
"Tons of areas to walk dogs. You just have to be careful with wild animals that could attack your dogs at night. "
2
Flag
Acmalzone
Resident
8y ago
"Small, friendly neighborhood town. Great neighbors. Awesome school system. Safe town. No chain stores or chain restaurants. All Ma & Pop shops and family owned restaurants."
2
Flag
annacollari
13y ago
"I have lived here for 2 years and it has already topped all the 10 other places i lived in, it is very clean, and my kids get a great education at the two high schools and one elementary school. All the people here are so nice and friendly. There are loads of places to walk and hang out, and it is great for kids, there is one park and baseball field, and there is another public park at the Elementary school. Upton is a Great place to live!"
0
Flag
Petersonk17
14y ago
"I live here since I was born and I think it is a wonderful neighborhood to live in. Lots of kids live around so it is good for families with children."
0
Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item

NEW - 1 DAY AGO
APPLY INSTANTLY
PET FRIENDLY
$1,895 - $2,175/mo
Fees may apply
1-2 bd
1 ba
135 Main Street | 135 Main St,
Upton, MA 01568
PET FRIENDLY
$1,850/mo
Fees may apply
2 bd
1 ba
299 Upton St #13,
Grafton, MA 01519
PET FRIENDLY
$2,200/mo
Fees may apply
1 bd
1 ba
149 Main St #204,
Upton, MA 01568
NEW - 1 DAY AGO
PET FRIENDLY
$2,000/mo
Fees may apply
3 bd
1 ba
20 Main St #1,
South Grafton, MA 01560
$1,600/mo
Fees may apply
2 bd
1 ba
11-21 Sutton St #17,
Northbridge, MA 01534
APPLY INSTANTLY
PET FRIENDLY
$2,250/mo
Total price
3 bd
1.5 ba
147 School St #147,
Northbridge, MA 01534
APPLY INSTANTLY
$1,600/mo
Total price
1 bd
1 ba
6 Maple Ave #E,
Upton, MA 01568
APPLY INSTANTLY
$1,995/mo
Total price
2 bd
1 ba
8 Harding St,
South Grafton, MA 01560
PET FRIENDLY
$4,500/mo
Total price
4 bd
2.5 ba
164 South St,
Upton, MA 01568
APPLY INSTANTLY
$1,700/mo
Total price
1 bd
1 ba
289 Providence Rd #3,
South Grafton, MA 01560
APPLY INSTANTLY
$1,800/mo
Total price
1 bd
1.5 ba
59 Maple Ave #A,
South Grafton, MA 01560
APPLY INSTANTLY
$2,200/mo
Total price
2 bd
1 ba
289 Providence Rd #1,
South Grafton, MA 01560
APPLY INSTANTLY
$3,200/mo
Total price
3 bd
1 ba
Address Not Disclosed,
Northbridge, MA 01534
APPLY INSTANTLY
$1,495/mo
Total price
2 bd
1 ba
19 River Ave #D,
South Grafton, MA 01560
APPLY INSTANTLY
PET FRIENDLY
$1,900/mo
Total price
2 bd
1 ba
98-100 School St #100C,
Northbridge, MA 01534
See more homes for rent in
Upton
Take a look

Skip to first item

Homes for sale near 22 Jackson Dr #66

Skip to last item

OPEN SAT, 10-4PM
$627,500
2 bd
2 ba
1,670 sqft
162 Rolling Ridge Dr #103,
Whitinsville, MA 01588
Duane Boucher, Boucher Real Estate, Inc.
OPEN SAT, 10-4PM
$609,900
2 bd
2 ba
1,670 sqft
164 Rolling Ridge Dr #102,
Whitinsville, MA 01588
Duane Boucher, Boucher Real Estate, Inc.
OFF MARKET
171 Rolling Ridge Dr #98,
Whitinsville, MA 01588
OPEN FRI, 1-3PM
$799,000
2 bd
2 ba
1,734 sqft
21 Boot Shop Rd #21,
Upton, MA 01568
Jeffrey Germagian, ERA Key Realty Services-Bay State Group
OFF MARKET
39 Crestwood Cir #42,
Whitinsville, MA 01588
OFF MARKET
37 Crestwood Cir #43,
Whitinsville, MA 01588
OPEN FRI, 1-3PM
$749,900
2 bd
2 ba
1,734 sqft
5 Boot Shop Rd #5,
Upton, MA 01568
Jeffrey Germagian, ERA Key Realty Services-Bay State Group
OPEN FRI, 1-3PM
$749,900
2 bd
2.5 ba
2,245 sqft
19 Boot Shop Rd #19,
Upton, MA 01568
Jeffrey Germagian, ERA Key Realty Services-Bay State Group
OPEN FRI, 1-3PM
$855,900
2 bd
2.5 ba
2,228 sqft
7 Boot Shop Rd #7,
Upton, MA 01568
The Kattman Team, ERA Key Realty Services-Bay State Group
See more homes for sale in
Upton
Take a look

Skip to first item

Off Market Homes Near 22 Jackson Dr #66

Skip to last item

SOLD
AUG 6, 2026
$788,000
3 bd
2.5 ba
2,367 sqft
304 Quaker St,
Northbridge, MA 01534
Brittany Palmerino, Mathieu Newton Sotheby's International Realty
SOLD
AUG 6, 2026
$875,000
4 bd
2.5 ba
3,493 sqft
656 Shining Rock Dr,
Northbridge, MA 01534
The Roach & Sherman Team, Compass
SOLD
AUG 4, 2026
$690,000
3 bd
2 ba
2,108 sqft
12 Whitney Rd,
Hopedale, MA 01747
Sarah Greco, Century 21 Custom Home Realty
SOLD
AUG 4, 2026
$325,000
6 bd
3.5 ba
2,654 sqft
66 Linwood Ave,
Northbridge, MA 01534
Sabrina Zyla, All Inclusive Realty, LLC
SOLD
AUG 3, 2026
$775,000
4 bd
3.5 ba
2,192 sqft
1 Leone Ln,
Mendon, MA 01756
Brittany Nazzaro, Berkshire Hathaway HomeServices Commonwealth Real Estate
SOLD
AUG 3, 2026
$515,000
3 bd
2 ba
1,776 sqft
66 High St,
Northbridge, MA 01588
Genevieve Botelho, Lamacchia Realty, Inc.
SOLD
AUG 3, 2026
$859,000
4 bd
2.5 ba
3,824 sqft
42 Shining Rock Dr,
Northbridge, MA 01534
Jeannie Leombruno, Century 21 Custom Home Realty
SOLD
JUL 31, 2026
$889,000
5 bd
3.5 ba
3,384 sqft
45 Elliot Trl,
Grafton, MA 01519
Glenn Damato, Media Realty Group Inc.
SOLD
JUL 31, 2026
$500,000
4 bd
2 ba
2,865 sqft
298 Providence Rd,
Northbridge, MA 01534
Livian Massachusetts Team, Keller Williams Realty
SOLD
JUL 31, 2026
$550,000
6 bd
2 ba
2,734 sqft
25-27 Elm Ln,
Whitinsville, MA 01588
The Devries Team, DeVries Dolber Realty, LLC
See more homes for sale in
Upton
Take a look

Skip to first item

Frequently asked questions about 22 Jackson Dr #66

What is 22 Jackson Dr #66 estimated to be worth?
Trulia's estimated value for 22 Jackson Dr #66 in Upton, MA is $595,900.
What is the price history for 22 Jackson Dr #66?
22 Jackson Dr #66 in Upton, MA last sold for $492,645 in October 2021.
Is Upton a buyer's or seller's market?
Upton is currently a seller's market, based on recent for-sale activity.
What do residents say about Upton?
Residents describe Upton, MA as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Upton, MA.
Does 22 Jackson Dr #66 have air conditioning?
Yes, 22 Jackson Dr #66 in Upton, MA has air conditioning.
Does 22 Jackson Dr #66 have parking?
Yes, 22 Jackson Dr #66 in Upton, MA has on-site parking.

22 Jackson Dr #66
Upton, MA 01568

$595,900

$595,900