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$2,495,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 7,560 Sq. Ft.
  • 3 Car Garage
  • Updated 1 day ago
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Located in Weston's prestigious Singing Oaks community, this extensively renovated 5-bedroom Colonial blends timeless architecture with exceptional modern luxury. Thoughtfully reimagined with meticulous craftsmanship, the home showcases sustainably sourced white oak flooring throughout the main and upper levels, extensive custom millwork, and elegant formal spaces including a living room with coffered ceiling and marble fireplace. The stunning gourmet kitchen has been completely redesigned with custom cabinetry, marble countertops, and a suite of premium appliances from Miele, Sub-Zero, Viking, and Wolf, creating a sophisticated centerpiece for both everyday living and entertaining. The inviting family room features a wood-burning fireplace with insert and a stylish dry bar, while the sun-filled all-season sunroom offers new tile flooring and dedicated climate control. Upstairs, the luxurious primary suite serves as a private retreat with fireplace, sitting room, spa-inspired bath, and balcony overlooking the property. Four additional bedrooms are generously sized and all feature beautifully renovated en-suite baths. The finished lower level provides excellent recreation and fitness space, while the walk-up third floor offers substantial storage and future expansion potential. Outside, the private grounds showcase a heated gunite pool with extensive upgrades, new roof, driveway, walkway, and generator, all within one of Weston's most desirable neighborhoods.

Full Property Details for 53 Singing Oaks Dr

General

  • Price: $2,495,000
  • HOA FEE: $42/month
  • HOA FEE FREQ.: Annually
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24158906
  • Updated: 3/19/2026
  • Added to Site: 1 day(s) ago

Interior

  • Number of Rooms: 13
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Cook Top, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 6
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Suite: Vaulted Ceiling, Balcony/Deck, Dressing Room, Firepla, 28 x 15, Upper
  • Bedroom 1: Bedroom - Balcony/Deck, Full Bath, Walk-In Closet, Hardwood Floor, 14.5 x 14.5, Upper
  • Bedroom 2: Bedroom - Full Bath, Walk-In Closet, Hardwood Floor, 14.5 x 16, Upper
  • Bedroom 3: Bedroom - Full Bath, Hardwood Floor, 16 x 18.75, Upper
  • Bedroom 4: Bedroom - Full Bath, Hardwood Floor, 20 x 15, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Fireplace, Hardwood Floor, 16 x 24, Main
  • Family Room: Family Room - 9 ft+ Ceilings, Dry Bar, Fireplace, Patio/Terrace, Hardwood Floor, 16.75 x 24, Main
  • Eat In Kitchen: Eat-In Kitchen - 9 ft+ Ceilings, Dining Area, Island, Hardwood Floor, 34.75 x 16.75, Main
  • Formal Dining Room: Formal Dining Room - 9 ft+ Ceilings, Hardwood Floor, 16.5 x 16, Main
  • Study: 9 ft+ Ceilings, Hardwood Floor, 16 x 15.5, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Vinyl Floor, 33.25 x 26.5, Lower
  • Rec Room: Vinyl Floor, 33.25 x 26.5, Lower
  • Laundry: Main Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, In Ground Pool

Exterior

  • Exterior Features: Balcony, Underground Utilities, Underground Sprinkler, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Subdivision: Singing Oaks
  • Driving Directions: 53 Singing Oaks Drive

School Information

  • Elementary School: Hurlbutt
  • High School: Weston

Community

  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Grounds Maintenance

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Hydro Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Upright Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Wood
  • Basement Desc.: Full, Heated, Partially Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 7,560
  • Above Ground: 5,521 Sq. Ft.
  • Below Ground: 2,039 Sq. Ft.
  • Year Built: 1994

Lot Features

  • Lot Size (Acres): 2.3
  • Zoning: R
  • Lot Description: Corner Lot, In Subdivision

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Pond, Beach Rights

Green Features

  • Energy Features: Generator

Financial Considerations

  • Association Fee: $500
  • Assoc Fee Freq.: Annually
  • Assessment Amount: $1,243,620
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 403799

Listed by William Raveis Real Estate, The Zerella Christy Team of William Raveis Real Estate, Brian Christy

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Listing agent

— 53 Singing Oaks Dr —

  • Brian Christy

    William Raveis Real Estate

Agent Contact: (203) 455-1223 Office Contact: (203) 255-6841

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 53 Singing Oaks Dr

School District:Weston School District
NameGradesDistance
Weston Intermediate School
95 School Road, Weston, CT 06883
3-53.1 mi
Hurlbutt Elementary School
9 School Road, Weston, CT 06883
PK-23.4 mi
Weston Middle School
135 School Road, Weston, CT 06883
6-82.7 mi
Weston High School
115 School Road, Weston, CT 06883
9-122.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 53 Singing Oaks Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/19/2026
Listed
$2,495,000
91.92%
MLS
3/31/2023
Sold
$1,300,000
—
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 53 Singing Oaks Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$29,723
2%
$1,243,620
—
2023
$29,188
-10%
$1,243,620
26%
2023
$32,569
—
$985,160
—
2022
$32,481
—
$985,160
—
2021
$32,431
2%
$985,160
—
2020
$31,890
—
$985,160
—
2019
$31,890
5%
$985,160
-5%
2018
$30,339
2%
$1,032,300
—
2017
$29,844
1%
$1,032,300
—
2016
$29,482
—
$1,032,300
—
2015
$29,596
2%
$1,032,300
—
2014
$29,152
3%
$1,032,300
-13%
2011
$28,403
—
$1,188,900
—
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.

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Listed by William Raveis Real Estate, The Zerella Christy Team of William Raveis Real Estate, Brian Christy

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53 Singing Oaks Drive, Weston, CT 06883 (MLS# 24158906) is a Single Family property with 5 bedrooms, 6 full bathrooms and 1 partial bathroom. 53 Singing Oaks Drive is currently listed for $2,495,000 and was received on March 19, 2026. Want to learn more about 53 Singing Oaks Drive? Do you have questions about finding other Single Family real estate for sale in Weston? You can browse all Weston real estate or contact a Coldwell Banker agent to request more information.

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