This home's estimate is 60.4% higher than the average sale price ($652K) of 6 comparable homes.
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- Sale & tax history
- Property details
- Neighborhood
- Climate
165 Gaylord Rd, Gaylordsville, CT 06755
About this home
Rare C. 1790 Federal-style brick Farmhouse on four private acres among small farms on scenic Gaylord Road in historic Gaylordsville. Picturesque country setting with views over farmland and distant hills. Solid and stately with a welcoming front porch, circular driveway and elegant rooms encompassing many original features, including five fireplaces, chestnut flooring, original ironware and hand-hewn beams. Several detached structures include a 2-car garage/barn, studio/playhouse, potting shed, and workshop. Inground gunite Scott pool and mature landscaping, including a magnificent row of hemlock shrubs along the property's front edge. Located just over the Sherman town line and within walking distance to several historic landmarks and hiking trails, including Little Red Schoolhouse – Gaylord School Circa 1740 -, The Washington Oak Tree (where Washington met his troops), the Naromiyocknowhusunkatankshunk Brook (“water flowing from the hills”), The James Morrissey Family Nature Preserve and Naromi Land Trust’s Strauss Preserve. Additional farmland and barns available. Less than 10 minutes to NYC trains and 90 minutes to Manhattan. New roof installed 2016.
Redfin Estimate
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Market trends in 06755, CT
Last updated September 2026
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Sale history for 165 Gaylord Rd
$248/sq ft
$303/sq ft
Tax history for 165 Gaylord Rd
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Property details
Parking
- Garage Information
- Garage & Parking: Barn, Detached Garage
- Garages Number: 2
Interior
- Interior Information
- Total Rooms: 10
- Laundry Room Location: First Floor
- Interior Features: Cable - Available, Security System
- In-Law Apartment: No
- Fireplaces Total: 5
- Appliances Included: Dryer, Electric Range, Refrigerator, Subzero, Washer
- Bathroom Information
- # of Baths (Full): 2
- # of Baths (Half): 1
- Bedroom Information
- Beds Total: 4
- Room Information
- Rooms Additional: Laundry Room, Mud Room, Workshop
- Room Count: 8
- Basement Description: Full With Hatchway, Interior Access, Storage, Unfinished
- Has Attic
- Attic Description: Storage Space, Walk-up
Exterior
- Exterior Features
- Exterior Siding: Brick, Clapboard
- Exterior Features: Barn, Garden Area, Gutters, Patio, Porch, Shed, Stone Wall, Storage Building
- Lot Information
- Lot Description: Lightly Wooded, Open Lot, Rolling, Fence - Partial, Fence - Stone
- Pool Information
- Swimming Pool
- Pool Description: In Ground Pool
- Building Information
- Color: Brick
- Property Information
- Property Type: Single Family For Sale
- Driveway Type: Asphalt, Circular, Paved
Financial
- Assessments Information
- Assessed Value: $267,120
- Rental Information
- Lease Purchase YN: No
Utilities
- Utility Information
- Water Source: Private Well
- Sewage System: Septic
- Hot Water Description: Oil
- Heat Type: Other, Radiator, Zoned
- Heat Fuel Type: Oil
- Fuel Tank Location: In Basement
- Energy Features: Generator
- Electric Amperage: 200
Location
- HOA Information
- Association Amenities: Putting Green, Health Club, Medical Facilities, Playground/Tot Lot, Tennis Courts
- School Information
- Intermediate School: PBOE
- High School: New Milford
- Elementary School: PBOE
- Location Information
- State: Connecticut
- Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Playground/Tot Lot, Tennis Courts
- Directions: From Sherman: 39N to Church Road to Gaylord Road. From NM, take Route 7 to Gaylord Rd.
- County: Litchfield
Public facts
- Beds: 4
- Baths: 2.5
- Sq. Ft.: 2,620
- Stories: 2.0
- Lot Size: 4 acres
- Style: Single Family Residential
- Year Built: 1790
- Year Renovated: —
- County: Litchfield County
- APN: 1874358
Other
- Documents & Disclosures
- Supplement Count Public: 1
Around this home
Schools
Public 3-5 • Assigned • 5.2mi
Public 6-8 • Assigned • 4.8mi
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
Minimal risk of a flood reaching the building in the next 30 years
Unlikely to be in a wildfire in next 30 years
7 days above 96° expected this year, 15 days in 30 years
16% chance of strong winds in next 30 years
2 unhealthy days expected this year, 2 days in 30 years
Sun exposure
In this area, properties receive around 8.7 hours in June and 4.2 hours in December, placing it below the U.S. average for solar exposure.
Nearby similar homes
New listings for sale in 06755
Home values near 165 Gaylord Rd
| Address | Redfin Estimate |
|---|---|
3 Beds | 2 Baths | 2246 Sq. Ft. | $546,705 |
2 Beds | 2 Baths | 1450 Sq. Ft. | $661,065 |
| Address | Redfin Estimate |
|---|---|
4 Beds | 2.5 Baths | 2592 Sq. Ft. | $781,959 |
2 Beds | 2 Baths | 1340 Sq. Ft. | $852,046 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 3 Baths | 2128 Sq. Ft. | $574,990 |
3 Beds | 2.5 Baths | 1242 Sq. Ft. | $556,853 |
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