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59 September Lane

Weston, Connecticut 06883

PENDING$1,425,000
Beds
5
Baths
3 | 1
SqFt
4,476
Acres
2.10
Year Built
1977
Matt Caiola

Matt Caiola

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Tennis Court2-Car Garage3 Fireplaces

About This Home

Nestled in one of Lower Weston's most desirable locations, this beautifully updated and thoughtfully expanded 5-bedroom, 3.5-bath residence offers the perfect blend of timeless charm and modern living. A bright open floor plan centers around a stunning great room with soaring vaulted ceilings and a dramatic double-sided fireplace that creates a warm connection between the kitchen and family room. The gourmet kitchen includes marble countertops, Wolf, Subzero and Gaggenau appliances and includes a cozy breakfast room and home office. Perfect for entertaining, the home flows seamlessly to a beautiful screened porch and sunny deck overlooking an expansive, level backyard complete with a private, lighted tennis court, providing an exceptional setting for recreation, gatherings, and room for pool. The luxurious primary suite serves as a private retreat, featuring a spectacular spa-inspired bath with soaring ceilings and two spacious walk-in closets. The walk-out lower level provides exceptional flexibility with a finished living area, a bedroom, and full bath that's ideal for guests, an au pair, home office or gym. Set on a picturesque property in a coveted neighborhood surrounded by beautiful homes, 59 September Lane offers privacy and tranquility while remaining just minutes from Weston's top-rated schools, Westport, commuting, shopping and dining. A rare opportunity to enjoy space, comfort, and resort-style amenities in one of Fairfield County's most sought-after communities.

Key Facts

City/Town
Weston
Neighborhood
Lower Weston
Property / Style
Single Family · Colonial
Year Built
1977
Days on Market
53 days
Beds
5
Baths
3 full · 1 half
Living Area
4,476 sq ft
Lot Size
2.10 acres
Garage / Parking
2 garage
Property Taxes
$18,848 / Annually

Market Snapshot

The Weston Market

Single Family · trailing 12 months

Median Days on Market

48

29 active listings

Median $ / Sq Ft

$381

29 active listings

Sale-to-List Ratio

100.1%

129 sales

How this home compares

List Price

$1.43M

vs $1.40M median

In line with median

Price / Sq Ft

$318

vs $381 median

16.5% below median

Days on Market

53 days

vs 48 days median

5 days longer than median

Based on 29 active and 129 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of July 28, 2026.

Location

59 September Lane, Weston, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$9,312

per month

  • Principal & Interest$7,266
  • Property Taxes$1,571
  • Insurance$475
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Weston
Neighborhood
Lower Weston
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1977
New Construction
No/Resale
Living Area
4,476 sq ft
Below Grade
1,070 sq ft

Schools

Elementary
Hurlbutt
Middle
Weston
High
Weston

Interior

Heating
Hot Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
3
Appliances
Gas CooktopWall OvenMicrowaveRange HoodSubzeroDishwasherDisposalWasherDryerWine Chiller
Basement
FullFully FinishedFull With Walk-Out
Interior Features
Cable - Pre-wiredOpen Floor Plan

Exterior & Lot

Lot Size
2.10 acres
Zoning
R
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Beach Rights
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Construction
Clapboard
Color
Sand
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Tennis CourtPorchDeckGuttersGarden AreaStone Wall
Lot Description
Fence - PartialFence - Electric PetDryLevel LotProfessionally Landscaped

Listing & Financials

Property Taxes
$18,848 / Annually
Days on Market
53
MLS #
24181357
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Cyd Hamer

(917) 744-5089

William Pitt Sotheby's Int'l

(203) 227-1246

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/28/2026 at 7:50 AM UTC.