28 Shepard St, Old Saybrook, CT 06475
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Property image
OFF MARKET

28 Shepard St
Old Saybrook, CT 06475

  • 4 Beds
  • 2 Baths
  • 2,019 sqft

$707,700

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $4,823/mo*
Refinance Your Home

$707,700

Trulia Estimate
as of Aug 7, 2026
Est. Refi. Payment $4,823/mo*
Refinance Your Home
4 Beds
2 Baths
2,019 sqft

Local Information

  • Map ViewExplore the area around 28 Shepard St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1940
Living Area
2,019 sqft
Price/Sqft
$351
Parking
Garage

About this House

Close to downtown Old Saybrook - Quiet neighborhood setting. 2100 sq ft, 4 bedroom, 2 bath ranch. Open floor plan, living room with fireplace, remodeled kitchen with granite counters and pantry open to dining room. Light filled great room with atrium to patio and level rear yard. Master bedroom with full bath and atrium to deck. Whole house attic fan, oil heat, vinyl siding and thermopane windows. Main floor in-law potential!
28 Shepard St, Old Saybrook, CT 06475 is a 4 bedroom, 2 bathroom, 2,019 sqft single-family home built in 1940. It last sold for $409,900 on Oct 23, 2020. It is currently off market. The Trulia Estimate is $707,700, with a rent estimate of $4,402/month.

Home Details for 28 Shepard St

Interior Features

Interior Details
BasementNumber of Rooms: 8
Heating & Cooling
Heating: Baseboard, OilAir ConditioningCooling System: WallHeating Fuel: Baseboard
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking Space: 1Parking: Garage Attached

Property Information

Year Built
Year Built: 1940
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 10018 sqft

Price History for 28 Shepard St

DatePriceEventSource
10/23/2020$409,900Sold
Smart MLS #170323684
09/02/2020$409,900PendingToActiveAgent Provided
08/14/2020$409,900PendingAgent Provided
08/06/2020$409,900Listed For SaleAgent Provided
02/12/2009$350,000Sold
Smart MLS #M9113545
10/16/2008$375,000ListingRemovedAgent Provided
08/23/2008$375,000Listed For SaleAgent Provided
12/01/1995$158,000Sold
N/A

Market trends in Old Saybrook

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
6MoM
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Property Tax and Assessment

Year2025
Tax$5,465
Assessment$352,600
Home facts updated by county records

Comparable Sales for 28 Shepard St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
3 Glen Drive, Old Saybrook, CT
0.16
Single-Family Home
$625,000
09/19/25
3
1.5
1,915
41 Farview Avenue, Old Saybrook, CT
0.38
Single-Family Home
$630,000
05/29/26
4
1.5
1,400
355 Main Street, Old Saybrook, CT
0.13
Single-Family Home
$707,500
12/19/25
3
1.5
2,194
17 Willard Street, Old Saybrook, CT
0.23
Single-Family Home
$656,000
06/22/26
3
3
1,683
18 Quarry Street, Old Saybrook, CT
0.44
Single-Family Home
$510,000
05/07/26
4
2
1,760
16 Howard Street, Old Saybrook, CT
0.31
Single-Family Home
$742,900
10/31/25
3
2
1,404
11 South View Terrace, Old Saybrook, CT
0.51
Single-Family Home
$840,000
05/08/26
4
1.5
2,005
20 Hill Street, Old Saybrook, CT
0.41
Single-Family Home
$700,000
01/07/26
2
2
1,432
16 Lynde Street, Old Saybrook, CT
0.33
Single-Family Home
$641,500
06/11/26
2
1.5
1,258
21 Cottage Place, Old Saybrook, CT
0.41
Single-Family Home
$650,000
12/02/25
3
3
1,720

Nearby homes

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Assigned Schools

These are the assigned schools for 28 Shepard St.
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 Old Saybrook

At least 42 Trulia users voted on each feature.

  • 88 % Say yards are well-kept

  • 88 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 84 % Say parking is easy

  • 78 % Say car is needed

  • 75 % Say people would walk alone at night

  • 66 % Say they plan to stay for at least 5 years

  • 61 % Say neighbors are friendly

  • 61 % Say kids play outside

  • 60 % Say there's wildlife

  • 58 % Say it's quiet

  • 57 % Say streets are well-lit

  • 56 % Say it's walkable to restaurants

  • 52 % Say there are sidewalks

  • 51 % Say there are community events

  • 43 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Diva For Life
    "I think is great to live here I think it safe for family and I hope I can move here with my family soon "
    0
    Flag
  • Trulia User
    "It’s a safe town, good schools. A lot of different activities and programs available for kids from toddlers to high school. The schools are located in convenient safe areas of the town. Lower traffic areas. Pedestrians are plentiful and kids riding bikes to and from school. Several beaches that are great for family gatherings as well as private time to yourself. Everything you need to bring your family up in a quiet shoreline community. Public transportation is available with a trolly during the months of spring and summer. The library is conveniently located next to the elementary school. Plenty of in town shopping available and plenty of great restaurants. Ice cream as well. "
    1
    Flag
  • Jocelynne B. .
    "It’s a safe place to live and the school system is very good. Small class rooms and everyone knows everyone. "
    0
    Flag
  • Tyfinkbus
    "I have lived in Old Saybrook for 15 years and the people are very friendly. The area is peaceful and very well maintained."
    0
    Flag
  • John D.
    "I commute by my car, motorcycle, scooter, or bicycle. I do not use public transportation. I also walk to the beach or downtown. "
    1
    Flag
  • J Jenkins
    "I lived in this neighborhood for 40 yrs, I love it here, we have had our children here and now have there own homes close by. We are only 1.1 miles from I-95, 1.5 to the supermarket, 2 miles to main St and 3 miles to the beach. A great area."
    0
    Flag
  • Svasmatics
    "I moved to Old Saybrook because I work in town. It is close to I-95 and Route9. The town itself and traffic is very different from winter to summer. Summer brings a lot of snow birds and visitors. Stores, traffic, commotion in general is heavier in the summer months. Food prices also go up in the summer."
    2
    Flag
  • Tony
    "I've lived in the area for over 12 years. Everything (shopping, dining, etc.) are all within walking distance, with plenty of sidewalks. most neighbors are friendly, and willing to lend a hand when needed."
    5
    Flag
  • Ali F.
    "No sidewalks. Some neighbors let dogs walk off the leash. There are Coyotes or coy dogs that are found to live around the marsh areas. I have had squirrels in my attic three times even after sealing. "
    6
    Flag
  • Ali F.
    "Love our neighborhood. Close walking to center of town. Neighbors are friendly. Birds, rabbits and squirrels. Sometimes can see coyote or deer. "
    0
    Flag
  • Karen E. d.
    "Train station is within walking distance with newly installed sidewalks and street lighting. I95 is easily accessible for commutes to New York or north. Personally, I am able to walk to my job in the downtown area. "
    0
    Flag
  • Annette M.
    "Wonderful beach community for families and singles. I rent here but most people own and the community is very tight knit and supportive."
    0
    Flag
  • Karen E. d.
    "Lots of friendly dogs in area. Most on leashes or in fenced yards. Some of the Main St. businesses put water out for our four legged friends. "
    1
    Flag
  • Bean_laura
    "Lots of other dogs. Dog parks. Pet stores. Fire hydrants. Pet friendly restaurants and bars. Pet friendly shopping."
    1
    Flag
  • Jocelynne B.
    "It’s a quiet neighborhood with no issues. Saybrook is safe and the school system is excellent. I enjoyed growing up and living in Saybrook. It’s a very friendly community."
    0
    Flag
  • Kearney j.
    "I've lived here for 25 years. it is a safe and welcoming community. pride I. home and property is prevalent everywhere. neighbors are friendly and supportive."
    0
    Flag
  • Rose H. M.
    "Fenwood beach is one of the most desirable areas along the shore, with a private beach, bordering Fenwick golf course, with views of the Saybrook lighthouses from the shore. The residents have lots of social activities, such as the summer lobster bake on the beach. Residents often ride golf carts around the neighborhood and to the beach. Fenwood beach is also a short drive into the quaint town center and to Saybrook Point. "
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 28 Shepard St

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Off Market Homes Near 28 Shepard St

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