Charming turn-of-the-century Craftsman farmhouse on one of Redding's most picturesque Scenic Roads - a rare find for those seeking space, character, and a genuine sense of place within reach of the city, but worlds away from it. Featuring authentic period details including crown molding, a bay window, beautiful hardwood floors, and soaring 9-foot ceilings, this three-bedroom, two-bath home balances historic charm with thoughtful modern updates. A newly expanded primary suite and a brand-new full bath on the second floor - complete with new HVAC - make the home as comfortable as it is characterful. Once the original switchboard for Redding Ridge, the property sits on a large, level lot with mature landscaping, spectacular perennial gardens that bloom spring through fall, a deck, brick terrace, and storage shed. The new roof and all-new windows mean the big work is done - just move in. Beyond the property itself, Redding delivers the lifestyle that's increasingly hard to find closer to the city: miles of open space, hiking trails, and beloved local institutions like the Mark Twain Library, New Pond Farm, Huntington State Park, and Putnam Park. It's a town with a strong sense of community, where weekends mean farmers markets and trail walks, not traffic. Additional highlights include an EV charger, generator, and 25 years of careful stewardship. History, updates, and room to grow - all in one of Connecticut's most desired small towns Heat pump/central air on second floor only. First floor is heated by radiators. Plans for two car garage expansion available. Audio/Video recording device at front and rear door.
Under contract
$629,000
159 Cross Highway, Redding, CT 06896
3beds
1,671sqft
Single Family Residence
Built in 1900
0.86 Acres Lot
$668,000 Zestimate®
$376/sqft
$-- HOA
What's special
- 40 days |
- 263 |
- 4 |
Zillow last checked:
Listing updated:
Listed by:
Bill Whitehead (203)606-8536,
Berkshire Hathaway NE Prop. 203-438-9501,
John Talley 203-947-1057,
Berkshire Hathaway NE Prop.
Source: Smart MLS,MLS#: 24165406
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Skylight, Vaulted Ceiling(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Vaulted Ceiling(s), Wall/Wall Carpet, Hardwood Floor
- Level: Upper
Bathroom
- Features: High Ceilings, Whirlpool Tub, Tub w/Shower, Tile Floor
- Level: Main
Bathroom
- Features: Stall Shower, Tile Floor
- Level: Upper
Den
- Features: High Ceilings, Hardwood Floor
- Level: Main
Dining room
- Features: Bay/Bow Window, High Ceilings, Hardwood Floor
- Level: Main
Kitchen
- Features: Skylight, Cathedral Ceiling(s), Double-Sink, Eating Space, Hardwood Floor
- Level: Main
Living room
- Features: Bay/Bow Window, High Ceilings, Hardwood Floor
- Level: Main
Heating
- Hot Water, Oil
Cooling
- Central Air, Window Unit(s)
Appliances
- Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Lower Level
Features
- Basement: Partial,Unfinished
- Attic: Access Via Hatch
- Has fireplace: No
Interior area
- Total structure area: 1,671
- Total interior livable area: 1,671 sqft
- Finished area above ground: 1,671
Property
Parking
- Total spaces: 6
- Parking features: Driveway, Unpaved, Private, Gravel
- Has uncovered spaces: Yes
Features
- Patio & porch: Porch, Deck
- Exterior features: Rain Gutters
Lot
- Size: 0.86 Acres
- Features: Corner Lot, Few Trees, Level, Cleared
Details
- Additional structures: Shed(s)
- Parcel number: 268864
- Zoning: R-2
- Other equipment: Generator, Generator Ready
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Antique,Farm House
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Stone
- Roof: Shingle
Condition
- New construction: No
- Year built: 1900
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Cable Available
Community & HOA
Community
- Features: Golf, Lake, Library, Park, Stables/Riding, Tennis Court(s)
- Security: Security System
- Subdivision: Redding Ridge
HOA
- Has HOA: No
Location
- Region: Redding
Financial & listing details
- Price per square foot: $376/sqft
- Tax assessed value: $287,300
- Annual tax amount: $8,487
- Date on market: 5/20/2026
Estimated market value
$668,000
$635,000 - $708,000
$4,085/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/16/2026 | Pending sale | $629,000$376/sqft |
Source:  Smart MLS #24165406 Report a problem | ||
| 5/29/2026 | Contingent | $629,000$376/sqft |
Source:  Berkshire Hathaway HomeServices New England Properties #24165406 Report a problem | ||
| 5/22/2026 | Listed for sale | $629,000+79.7%$376/sqft |
Source: Smart MLS #24165406 Report a problem | ||
| 12/12/2000 | Sold | $350,000+42.9%$209/sqft |
Source: Smart MLS #98078625 Report a problem | ||
| 1/28/1998 | Sold | $245,000-5.8%$147/sqft |
Source: Smart MLS #97031195 Report a problem | ||
| 4/15/1994 | Sold | $260,000$156/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,487 +2.9% | $287,300 |
| 2024 | $8,251 +3.7% | $287,300 |
| 2023 | $7,955 -2.8% | $287,300 +17% |
| 2022 | $8,185 +1.5% | $245,500 |
| 2021 | $8,062 | $245,500 |
| 2020 | $8,062 | $245,500 |
| 2019 | $8,062 +3.5% | $245,500 |
| 2018 | $7,787 -0.9% | $245,500 -7.5% |
| 2017 | $7,858 +1.3% | $265,300 |
| 2016 | $7,757 +1.1% | $265,300 |
| 2015 | $7,670 | $265,300 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06896
Nearby schools
GreatSchools rating
- 8/10Redding Elementary SchoolGrades: PK-4Distance: 1.6 mi
- 9/10John Read Middle SchoolGrades: 5-8Distance: 2.4 mi
- 7/10Joel Barlow High SchoolGrades: 9-12Distance: 1.2 mi
Schools provided by the listing agent
- Elementary: Redding
- Middle: John Read
- High: Joel Barlow
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Fairfield County
- Redding
- 06896
- 159 Cross Highway
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Nearby neighborhoods
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