149 Apple Ln, Roxbury, CT 06783
OFF MARKET

149 Apple Ln
Roxbury, CT 06783

  • 3 Beds
  • 3.5 Baths
  • 3,698 sqft (on 9.06 acres)

$3,423,900

Trulia Estimate
as of Jul 18, 2026
Est. Refi. Payment $22,449/mo*
Refinance Your Home

$3,423,900

Trulia Estimate
as of Jul 18, 2026
Est. Refi. Payment $22,449/mo*
Refinance Your Home
3 Beds
3.5 Baths
3,698 sqft
(on 9.06 acres)

Local Information

  • Map ViewExplore the area around 149 Apple Ln.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

A Cherished Secret for 39+ Years, The Country Retreat of Legendary Broadway icon Stephen Sondheim is Now Available for Those Who Appreciate the Magic of Theater and the Allure of Country Living. Nestled on over 9 acres Along a Serene Country Road, this Lovingly Restored c1792 Home Offers a Timeless Blend of History, Elegance, and Modern Comfort. 3 Bedrooms, 3.5 Baths in Main House + Separate Pool & 1-Bedroom Pool House. Dramatic Living Room with Cathedral Ceiling & Stone Fireplace. Separate Dining Room with Fireplace. Main Level Primary Suite with Large Full Bath. 2 Ensuite Bedrooms Upstairs Each with Sitting Rooms. Wonderful Paneled Library. Separate 2-Car Detached Garage. Magical & Special!
149 Apple Ln, Roxbury, CT 06783 is a 3 bedroom, 4 bathroom, 3,698 sqft single-family home built in 1792. It last sold for the $3,250,000 asking price on Apr 15, 2024. It is currently off market. The Trulia Estimate is $3,423,900, with a rent estimate of $7,589/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 149 Apple Ln

Interior Features

Interior Details
Basement: Full,Interior EntryNumber of Rooms: 11Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Kitchen, Library, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3698 Square Feet
Appliances & Utilities
Appliances: Gas Range, Freezer, Dishwasher, Washer, Dryer, Electric Water HeaterDishwasherDryerLaundry: Main Level,Mud RoomWasher
Heating & Cooling
Heating: Forced Air,Zoned,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace

Exterior Features

Exterior Home Features
Roof: WoodPatio / Porch: PatioFencing: StoneOther Structures: Guest House, Pool HouseFoundation: Concrete Perimeter, StoneHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Detached,Circular Driveway,Gravel
Pool
Pool: In Ground, Pool/Spa ComboPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3698 Square Feet

Property Information

Year Built
Year Built: 1792
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial,Antique
Building
Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 867227

Price & Status

Price
List Price: $3,250,000
Status Change & Dates
Off Market Date: Tue Dec 19 2023Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Roxbury
School Information
Elementary School: Booth FreeHigh School: Per Board of Ed

Building

Building Area
Building Area: 3698 Square Feet

Community

Community Features: Library, Park, Private School(s), Pool, Tennis Court(s)

HOA

No HOA

Lot Information

Lot Area: 9.06 Acres

Miscellaneous

BasementMls Number: 170609549Attic: Walk-upAbove Grade Unfinished Area: 3698

Additional Information

LibraryParkPrivate School(s)PoolTennis Court(s)
Last check for updates: about 2 hours ago
Listed by Graham Klemm, (860) 488-6635
Klemm Real Estate Inc, (860) 868-7313
Carolyn Klemm, (860) 488-6721
Klemm Real Estate Inc, (860) 868-7313
Bought with: Stephen Pener, (203) 470-0393, William Pitt Sotheby's Int'l, (860) 927-1141
Source: Smart MLS, MLS#170609549

Price History for 149 Apple Ln

DatePriceEventSource
04/15/2024$3,250,000Sold
Smart MLS #170609549
12/19/2023$3,250,000PendingSmart MLS #170609549
11/21/2023$3,250,000ContingentSmart MLS #170609549
11/09/2023$3,250,000Listed For SaleSmart MLS #170609549

Market trends in Roxbury

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
32
2MoM
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Property Tax and Assessment

Year2025
Tax$19,030
Assessment$1,463,840
Home facts updated by county records

Comparable Sales for 149 Apple Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
44 South Street, Roxbury, CT
0.91
Single-Family Home
$1,825,000
08/07/25
3
3.5
3,450
19 Good Hill Terrace, Roxbury, CT
1.41
Single-Family Home
$1,465,000
08/22/25
3
3
3,022
34 Bacon Road, Roxbury, CT
1.26
Single-Family Home
$959,000
03/30/26
4
4
3,686
32 Grassy Hill Road, Roxbury, CT
1.54
Single-Family Home
$1,966,500
12/22/25
4
4
4,728
18 Mallory Road, Roxbury, CT
1.66
Single-Family Home
$2,575,000
08/29/25
3
3.5
3,384
88 Mallory Road, Roxbury, CT
1.51
Single-Family Home
$917,500
08/21/25
4
2.5
3,004
22 East Woods Road, Roxbury, CT
1.63
Single-Family Home
$610,000
04/17/26
4
2.5
3,476
30 Hickory Lane, Roxbury, CT
1.52
Single-Family Home
$1,400,000
11/06/25
4
5.5
4,721
78 Garnet Road, Roxbury, CT
2.07
Single-Family Home
$1,650,000
10/23/25
3
3.5
3,302

Nearby homes

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Assigned Schools

These are the assigned schools for 149 Apple Ln.
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 Roxbury

At least 2 Trulia users voted on each feature.

  • 100 % Say there's holiday spirit

  • 100 % Say car is needed

  • 100 % Say it's quiet

  • 80 % Say yards are well-kept

  • 80 % Say it's dog friendly

  • 80 % Say parking is easy

  • 67 % Say there's wildlife

  • 50 % Say people would walk alone at night

  • 50 % Say they plan to stay for at least 5 years

  • 29 % Say neighbors are friendly

  • 25 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Lisa r. h.
    "This is an incredibly supportive town, with many young families. Lots of townwide events to meet new people, and friendly neighbors. We moved in 9 years ago and love living here!"
    2
    Flag
  • Maria T.
    "Peaceful and surrounded by nature. The perfect escape from the city or a great place to live full time."
    0
    Flag
  • Katherine
    "This is one of the most gorgeous towns in Connecticut. Quintessential New England, with lots of privacy - yes there are celebs - but who cares! They are just people too. You get the best of everything - lovely town green, no traffic, a short drive to everything you need, acreage with your house and low taxes. People are friendly, helpful, nice to you and no smog!!!!!!!!! Yes, we love it here. "
    0
    Flag

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IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.