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$810,000

  • For Sale
  • Under Contract
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,808 Sq. Ft.
  • 2 Car Garage
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This historic 18th-century Gaylord family homestead in New Milford, Connecticut, offers a perfect blend of authentic period charm and thoughtful modern enhancements. Set on picturesque grounds at 43 Gaylord Road, this distinctive Litchfield County property features versatile living spaces including an open-concept kitchen, living room, inviting Sun Room, formal dining room, and a cozy Snuggery with brick fireplace abutting the kitchen. The upper level showcases a spacious primary bedroom with vaulted ceilings, two walk-in closets, an en-suite bathroom, and a private balcony overlooking the backyard oasis. Three additional bedrooms and a full hall bath complete the second floor, providing generous accommodation for family and guests. Outdoor living reaches its pinnacle with a heated in-ground swimming pool, adjacent cabana, and expansive entertainment areas perfect for gatherings of all sizes. The property's amenities extend to a two-car attached garage and separate temperature-controlled barn offering versatile space for storage, workshop, or creative pursuits. Perfectly positioned with nearby hiking trails, minutes to Kent and New Milford's charming village centers, and convenient access to Metro North, this exceptional historic estate combines architectural significance, modern comfort, and an ideal location in one of Connecticut's most desirable communities.

Full Property Details for 43 Gaylord Rd

General

  • Price: $810,000
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24137843
  • Updated: 12/15/2025
  • Added to Site: 76 day(s) ago

Interior

  • Number of Rooms: 10
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Primary Bathroom: Primary Bath, Upper
  • Full Bath: Main
  • Partial Bath: Upper

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Main
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Family Room: Family Room, Main
  • Kitchen: Kitchen, Main
  • Dining Room: Dining Room, Main
  • Office: Office, Lower

Additional Information

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

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Litchfield
  • Driving Directions: GPS

School Information

  • Elementary School: Per Board of Ed
  • High School: New Milford

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Antique
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Partially Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,808
  • Above Ground: 3,528 Sq. Ft.
  • Below Ground: 280 Sq. Ft.
  • Year Built: 1725

Lot Features

  • Lot Size (Acres): 1.14
  • Zoning: R40
  • Lot Description: Level Lot, Professionally Landscaped

Financial Considerations

  • Assessment Amount: $438,190
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1870048

Listed by Elyse Harney Real Estate, Liza Reiss and Elyse Harney Real Estate, Holly Leibrock

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Listing agents

— 43 Gaylord Rd —

  • Liza Reiss

    Elyse Harney Real Estate

  • Holly Leibrock

    Elyse Harney Real Estate

Agent Contact: (860) 671-0288 Office Contact: (860) 435-0120

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 43 Gaylord Rd

School District:New Milford School District
NameGradesDistance
Sarah Noble Intermediate School
25 Sunny Valley Road, New Milford, CT 06776
3-56 mi
Hill And Plain School
60 Old Town Park Road, New Milford, CT 06776
K-27.5 mi
Schaghticoke Middle School
23 Hipp Road, New Milford, CT 06776
6-84.8 mi
New Milford High School, New Milford, CT
388 Danbury Road, New Milford, CT 06776
9-128.1 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 43 Gaylord Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/03/2025
Listed
$810,000
15.71%
MLS
12/10/2021
Sold
$700,000
—
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 43 Gaylord Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$13,566
4%
$438,190
—
2023
$13,045
3%
$438,190
—
2023
$12,699
2%
$438,190
—
2022
$12,423
3%
$438,190
2%
2021
$12,064
9%
$431,330
12%
2020
$11,038
—
$384,860
—
2019
$11,045
2%
$384,860
—
2018
$10,842
3%
$384,860
—
2017
$10,487
2%
$384,860
—
2016
$10,303
12%
$384,860
12%
2015
$9,222
4%
$344,750
2%
2014
$8,909
2%
$338,730
—
2011
$8,756
—
$338,730
—
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.

Estimate the Cost for 43 Gaylord Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Elyse Harney Real Estate, Liza Reiss and Elyse Harney Real Estate, Holly Leibrock

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43 Gaylord Road, New Milford, CT 06755 (MLS# 24137843) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 43 Gaylord Road is currently listed for $810,000 and was received on November 03, 2025. Want to learn more about 43 Gaylord Road? Do you have questions about finding other Single Family real estate for sale in New Milford? You can browse all New Milford real estate or contact a Coldwell Banker agent to request more information.

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