Storybook Charm Meets Modern Convenience in Lower Weston! Perched atop a gentle knoll, this beautifully maintained 3-bedroom, 2-bath home offers stunning sunsets, serene pond views, and timeless character. Ideally located in Lower Weston, just minutes from the Westport train station, I-95, and the Merritt Parkway, the home provides a peaceful setting with easy commuting access. Step inside to find gleaming hardwood floors, a sunken living room with a dramatic stone fireplace, and a dining room wrapped in glass, creating a bright, seamless connection to the outdoors. French doors open to a lovely flagstone patio, perfect for entertaining, while the heated 4-season sunroom offers year-round comfort and versatility. Additional features include original stone walls, a spacious detached garage, a charming potting shed, and room for expansion. The home is now fully empty and ready for move in, freshly cleaned, landscaped, and power-washed-ready for immediate move-in! Take advantage of the recent price reduction and the opportunity to settle in before the school year begins in award-winning Weston schools. This is a rare chance to own a one-of-a-kind home with warmth, character, and convenience.
Single-familyProperty Type
1947Year Built
0.73 acresLot Size
$473Est. Price/Sq.Ft.
2 car garageParking
Listed by William J Gill• Compass Connecticut, LLC
Bought with Raymond Belanger• Real Broker CT, LLC
Source:Smart MLS #24111820
Redfin Estimate
$757,567
$88K since sold in September 2025$23K since September
Recently sold homes
Estimate history
Homes for sale
This home's estimate is 1.6% higher than the average sale price ($746K) of 6 comparable homes.
Sitting on a gentle knoll perfectly situated for glorious year around sunsets, since 1947 The Pumpkin Cottage continues to be the attractive home for the 1st timer or down sizer looking for a recently updated country retreat. This unique home offers many options for a variety of lifestyles. The gleaming hardwood floors, sunken living room w/stone fireplace, dining room with walls of glass surrounded by original stone walls and pretty landscaping with large detached garage and the secret potting shed complete the picture. Or, if you're just looking for a 3 br 2 bath place to rest your head that's just a LITTLE DIFFERENT than cookie cutter....The Pumpkin Cottage is for you.
Photos from previous owner in September 2022.... some room colors have changed and furniture is different. Note room dimensions are approximate until verified.
Smart MLS #170519793
Oct 14, 2022
Sold
$575,000
$359/sq ft
Oct 4, 2022
Pending
—
Sep 20, 2022
Contingent
—
Sep 11, 2022
Listed
$539,000
$336/sq ft
Sep 2, 2022
Coming Soon
$539,000
$336/sq ft
Smart MLS #99122229
Feb 25, 2016
Sold
$425,000
$265/sq ft
Feb 14, 2016
Listing Removed
—
Oct 8, 2015
Listed
$450,000
$281/sq ft
Smart MLS #99025894
Aug 8, 2013
Listing Removed
—
May 2, 2013
Listed
$499,999
$312/sq ft
Public Records
Apr 2, 2001
Sold
$345,000
$215/sq ft
Smart MLS #98090687
Jan 24, 2001
Listed
$375,000
$234/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$7,666 (+0.3%)
$133,060 + $98,830
$231,890
2022
$7,645 (+0.1%)
$133,060 + $98,830
$231,890
2021
$7,634 (+1.7%)
$133,060 + $98,830
$231,890
2020
$7,506
$133,060 + $98,830
$231,890
2019
$7,506 (+7.4%)
$133,060 + $98,830
$231,890
2018
$6,989 (+1.7%)
$144,100 + $93,700
$237,800
2017
$6,875 (+1.2%)
$144,100 + $93,700
$237,800
2016
$6,792 (−2.9%)
$144,100 + $93,700
$237,800
2013
$6,995
$195,700 + $97,100
$292,800
Tax history for 105 Ladder Hill Rd N
Year
Property tax
Land + Additions
Assessment*
2023
$7,666 (+0.3%)
$133,060 + $98,830
$231,890
2022
$7,645 (+0.1%)
$133,060 + $98,830
$231,890
2021
$7,634 (+1.7%)
$133,060 + $98,830
$231,890
2020
$7,506
$133,060 + $98,830
$231,890
2019
$7,506 (+7.4%)
$133,060 + $98,830
$231,890
2018
$6,989 (+1.7%)
$144,100 + $93,700
$237,800
2017
$6,875 (+1.2%)
$144,100 + $93,700
$237,800
2016
$6,792 (−2.9%)
$144,100 + $93,700
$237,800
2013
$6,995
$195,700 + $97,100
$292,800
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.