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$1,175,000 Contingent

  • For Sale
  • Contingent
  • Single Family
  • 5 Beds
  • 2 Full Baths
  • 3 Partial Baths
  • 3,664 Sq. Ft.
  • 3 Car Garage
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Discover the best of Connecticut shoreline living at 11 Trolley Crossing in Old Saybrook-a private 3+ acre compound blending classic Colonial architecture with modern luxury. Designed for those who value space, comfort, and connection, this 3,600 sq ft residence invites you to experience an exceptional lifestyle surrounded by nature and minutes from the coast. A covered front porch opens to expansive, light-filled rooms where timeless craftsmanship meets everyday convenience. The kitchen fireplace creates a welcoming centerpiece for gatherings, while a second fireplace in the living room adds warmth and style. The first-floor primary suite allows for true one-level living, complemented by four additional bedrooms upstairs. The walk-out lower level features a third fireplace, half bath, and flexible space ideal for an in-law, recreation room, guest suite, or studio. Step outside to your own resort-style oasis an in-ground pool, pool house with full bathroom, and extensive stone patio designed for entertaining and relaxation. A heated, oversized 30x20 outbuilding offers additional garage or workshop space, joined by a detached three-car garage. The fenced yard and stone wall surround enhance privacy in a serene natural setting close to beaches, marinas, golf, and Old Saybrook's vibrant Main Street.Luxury, space, and versatility combine at 11 Trolley Crossing a property that invites you to visit, explore, and stay. Easy commute on Amtrak to New York City. Only 2hrs door - door

Full Property Details for 11 Trolley Crossing

General

  • Price: $1,175,000
  • Taxes: (July 2025-June 2026)
  • Status: Contingent
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24133796
  • Updated: 12/24/2025
  • Added to Site: 92 day(s) ago

Interior

  • Number of Rooms: 11
  • Rooms/Areas: Workshop
  • Interior Features: Cable - Available, Central Vacuum, Auto Garage Door Opener
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Dishwasher, Dryer, Microwave, Oven/Range, Refrigerator, Washer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 2
  • Half Bathrooms: 3

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Bedroom Suite, Ceiling Fan, Dressing Room, Full Bath, Stall Shower, Wall/Wall Carpet, Main
  • Bedroom 1: Bedroom - Hardwood Floor, 16 x 10, Upper
  • Bedroom 2: Bedroom - Hardwood Floor, 16 x 10, Upper
  • Bedroom 3: Bedroom - Hardwood Floor, 16 x 13, Upper
  • Bedroom 4: Bedroom - Wall/Wall Carpet, 17 x 13, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, 20 x 13, Main
  • Family Room: Family Room - Fireplace, Half Bath, Patio/Terrace, Wall/Wall Carpet, Lower
  • Kitchen: Kitchen - Balcony/Deck, Breakfast Bar, Granite Counters, Dining Area, Eating Space, Fireplace, 16 x 12, Main
  • Dining Room: Dining Room - Hardwood Floor, 13 x 12, Main
  • Laundry: Main Level

Additional Information

  • Pool: Yes
  • Pool Description: In Ground Pool

Exterior

  • Exterior Features: Breezeway, Barn, Cabana, Covered Deck, Stone Wall, Kennel

Parking

  • Garage: Yes
  • Garage Spaces: 3
  • Parking: Detached Garage

Location

  • County: Middlesex
  • Driving Directions: Use GPS.

School Information

  • Elementary School: Kathleen E. Goodwin
  • High School: Old Saybrook

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Baseboard, Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Heated, Interior Access, Walk-out, Liveable Space, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,664
  • Above Ground: 2,882 Sq. Ft.
  • Below Ground: 782 Sq. Ft.
  • Year Built: 1968

Lot Features

  • Lot Size (Acres): 3.2
  • Zoning: AA-3
  • Lot Description: Lightly Wooded, Level Lot, On Cul-De-Sac

Financial Considerations

  • Assessment Amount: $600,200
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1029310

Listed by William Raveis Real Estate, Jennifer Gurnell

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Listing agent

— 11 Trolley Crossing —

  • Jennifer Gurnell

    William Raveis Real Estate

Agent Contact: (860) 227-1212 Office Contact: (203) 453-0391

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 11 Trolley Crossing

School District:Old Saybrook School District
NameGradesDistance
Old Saybrook Middle School
60 Sheffield Street, Old Saybrook, CT 06475
4-82.7 mi
Kathleen E. Goodwin School
80 Old Boston Post Road, Old Saybrook, CT 06475
PK-32.9 mi
Old Saybrook Senior High School
1111 Boston Post Road, Old Saybrook, CT 06475
9-122.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 11 Trolley Crossing Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/03/2025
Price Reduced
$1,175,000
-1.26%
MLS
10/17/2025
Listed
$1,190,000
68.79%
MLS
8/10/2007
Sold
$705,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 11 Trolley Crossing

Year
Property Taxes
Change
Tax Assessment
Change
2024
$9,303
2%
$600,200
—
2023
$9,123
16%
$600,200
56%
2023
$7,888
2%
$385,700
—
2022
$7,745
—
$385,700
—
2021
$7,733
—
$385,700
—
2020
$7,733
2%
$385,700
—
2019
$7,618
-3%
$385,700
-4%
2018
$7,852
—
$400,600
1%
2017
$7,829
2%
$398,200
—
2016
$7,669
2%
$398,200
—
2015
$7,490
2%
$398,200
—
2014
$7,367
-9%
$398,200
-25%
2011
$8,121
—
$534,300
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 11 Trolley Crossing

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by William Raveis Real Estate, Jennifer Gurnell

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11 Trolley Crossing, Old Saybrook, CT 06475 (MLS# 24133796) is a Single Family property with 5 bedrooms, 2 full bathrooms and 3 partial bathrooms. 11 Trolley Crossing is currently listed for $1,175,000 and was received on October 15, 2025. Want to learn more about 11 Trolley Crossing? Do you have questions about finding other Single Family real estate for sale in Old Saybrook? You can browse all Old Saybrook real estate or contact a Coldwell Banker agent to request more information.

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