$1,175,000
$15K PRICE DROP

11 Trolley Crossing Old Saybrook, CT 06475

Estimated payment $6,937/month

Total Views 14,054
5 Beds
5 Baths
3,664 Sq Ft
$321 Price per Sq Ft

Highlights

  • Barn
  • Cabana
  • Colonial Architecture
  • Kathleen E. Goodwin School Rated A-
  • 3.2 Acre Lot
  • Attic

About This Home

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

Listing Agent

Jennifer Gurnell

William Raveis Real Estate Brokerage Phone: (860) 227-1212 License #RES.0002284 Listed on: 10/15/2025

William Raveis Real Estate

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $9,303

Year Built

  • Built in 1968

Lot Details

  • 3.2 Acre Lot
  • Kennel
  • Stone Wall
  • Property is zoned AA-3

Home Design

  • Colonial Architecture
  • Concrete Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Clap Board Siding
  • Concrete Siding

Interior Spaces

  • Central Vacuum
  • 3 Fireplaces
  • Workshop
  • Pull Down Stairs to Attic

Kitchen

  • Oven or Range
  • Microwave
  • Dishwasher

Bedrooms and Bathrooms

  • 5 Bedrooms

Laundry

  • Laundry on main level
  • Dryer
  • Washer

Basement

  • Heated Basement
  • Walk-Out Basement
  • Basement Fills Entire Space Under The House
  • Interior Basement Entry

Parking

  • 3 Car Garage
  • Automatic Garage Door Opener

Pool

  • Cabana
  • In Ground Pool

Outdoor Features

  • Covered Deck
  • Breezeway

Schools

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

Farming

  • Barn

Utilities

  • Central Air
  • Baseboard Heating
  • Hot Water Heating System
  • Heating System Uses Oil
  • Private Company Owned Well
  • Hot Water Circulator
  • Fuel Tank Located in Ground
  • Cable TV Available

Listing and Financial Details

  • Assessor Parcel Number 1029310

Home Details

Home Type

Single Family

Est. Annual Taxes

$9,303

Year Built

Built in 1968

Lot Details

0

Listing Details

  • Neighborhood: N/A
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 2882
  • Sq Ft Est Heated Below Grade: 782
  • Total Sq Ft: 3664
  • Year Built: 1968
  • New Construction: No/Resale
  • In Law Access: DETCH,LOWER
  • Remarks Public Addendum: Introducing 11 Trolley Crossing - an exceptional Connecticut shoreline estate offering the rare combination of compound-style living, privacy, and timeless elegance. Set on 3.1 private acres in the heart of Old Saybrook, this 3,600 sq ft Colonial masterpiece blends classic architecture with resort-caliber amenities, creating a private retreat just minutes from beaches, marinas, golf, and Main Street's fine shops and dining. Enclosed by stone walls and mature trees, the approach sets a tone of understated grandeur. A stately covered front porch opens to expansive, light-filled interiors that showcase hardwood floors, refined millwork, and exceptional craftsmanship throughout. The chef's kitchen serves as the centerpiece of the home, complete with a fireplace, oversized island, and custom cabinetry, flowing seamlessly into elegant dining and living spaces designed for effortless entertaining. The living room, warmed by a second fireplace, exudes comfort and style with sunlit views of the landscaped grounds. The first-floor primary suite provides a serene escape with private bath and garden views, ideal for one-level living. Upstairs, four additional bedrooms offer flexible space for family, guests, or dual home offices. The walk-out lower level adds another dimension of luxury, featuring a third fireplace, half bath, and open layout perfect for an in-law suite, guest quarters, or recreation area-tailored for multi-generational or compound-style living. Outdoors, the estate transforms into a private resort. The heated in-ground pool, pool house with full bath, and expansive stone patio create an unparalleled setting for entertaining or relaxation. A heated 30x20 outbuilding provides additional space for a gym, studio, or car collection, while the detached three-car garage enhances both form and function. Set in a peaceful, natural landscape yet close to Old Saybrook's coastal attractions, Fenwick, Essex Village, and commuter routes to New Haven and Hartford, this property redefines Connecticut shoreline luxury. At 11 Trolley Crossing, every element-from the architecture to the acreage-has been thoughtfully curated for those who value space, privacy, and refined coastal living. This is more than a home; it's a private Connecticut compound designed for generations to enjoy. Can you work remote? Easy commute on Amtrak from Old Saybrook Station to New York City.
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Directions: Use GPS.
  • In Law Apartment: Possible
  • Street Type: Crossing
  • Office Attribution Contact: (203) 453-0391
  • Reserve Prospect: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 5
  • Total Bathrooms: 5
  • Full Bathrooms: 2
  • Half Bathrooms: 3
  • Fireplaces: 3
  • Attic Description: Pull-Down Stairs
  • Basement Description: Full, Heated, Interior Access, Walk-out, Liveable Space, Full With Walk-Out
  • Interior Amenities: Cable - Available, Central Vacuum, Auto Garage Door Opener
  • Appliances: Dishwasher, Dryer, Microwave, Oven/Range, Refrigerator, Washer
  • Additional Rooms: Workshop
  • Laundry Room Location: mud room
  • Laundry Room Info: Main Level
  • Attic: Yes

Exterior Features

  • Exterior Features: Breezeway, Barn, Cabana, Covered Deck, Stone Wall, Kennel
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Not Applicable
  • Swimming Pool: Yes
  • Pool: In Ground Pool
  • Construction Description: Frame, Concrete

Garage/Parking

  • Garages Number: 3
  • Garage And Parking: Detached Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Baseboard, Hot Water
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Ground
  • Hot Water Description: Domestic
  • Water Source: Private Well
  • Sewer: Septic

Lot Info

  • Acres: 3.2
  • Lot Description: Lightly Wooded Level Lot On Cul-De-Sac
  • Zoning: AA-3
  • Parcel #: 1029310

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 9303

MLS Schools

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

Map

Range of Values:

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Value Increase
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Percent Increase
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Adjusted for Inflation
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Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $9,303 $600,200 $118,000 $482,200
2024 $9,123 $600,200 $118,000 $482,200
2023 $7,888 $385,700 $78,600 $307,100
2022 $7,745 $385,700 $78,600 $307,100
2021 $7,733 $385,700 $78,600 $307,100
2020 $7,733 $385,700 $78,600 $307,100
2019 $7,618 $385,700 $78,600 $307,100
2018 $7,852 $400,600 $73,800 $326,800
2017 $7,829 $398,200 $73,800 $324,400
2016 $7,669 $398,200 $73,800 $324,400
2015 $7,490 $398,200 $73,800 $324,400
2014 $7,367 $398,200 $73,800 $324,400
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
12/03/2025 12/03/25 Price Changed $1,175,000 -1.3% $321 / Sq Ft
10/17/2025 10/17/25 For Sale $1,190,000 -- $325 / Sq Ft
Source: SmartMLS

Purchase History

Date Type Sale Price Title Company
Deed $705,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Open $150,000 No Value Available
Closed $220,000 No Value Available
Open $350,000 No Value Available
Source: Public Records

Source: SmartMLS

MLS Number: 24133796

SmartMLS

APN: OSAY-000063-000019

Connecticut Middlesex County Old Saybrook 06475

11 Trolley Crossing, Old Saybrook, CT

For Sale

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Jennifer Gurnell
Listing Agent
Jennifer Gurnell
Section Image
William Raveis Real Estate
(860) 981-0150