Highest & Best Due by 6/17/2025 at 5PM. First time to the market this turnkey 2,692 sq ft Grand Ranch is nestled in on 2.78 bucolic acres surrounded by nature & mature trees. Lovingly maintained, this home provides the perfect set up for stress free living & entertaining boasting a large eat in kitchen with center island, dining area, SS appliances, dual wall ovens and propane cooktop, French door leading to side deck & built-in hutch flowing right into the Living & Dining room combo w/Hardwood flooring, majestic stone surround fireplace, coffered ceiling & entertainment center. True 1 level living offers a huge Primary Suite complete with spa-like primary bath, 2 walk in closets & tray ceiling w/crown molding & access to another private deck. Two other generously sized bedrooms (1 currently being used as an office) a half bath, pantry/mudroom, another Full bath, separate laundry room, full sized basement with second FP piped for propane, an attached 2 car garage with driveway that can fit all of your vehicles round out the tour of this amazing home. Follow this property at Finaloffer.com for instant updates & offer alerts. Close proximity to Burr Pond State Park & Highland Lake. This home will not disappoint. Imagine yourself as one with nature as you relax on any of the outdoor areas with loads of privacy! Room sizes approx. Schedule your private tour today!
Sold for $639,000
$639,000
102 Hollow Hill Road, Winchester, CT 06098
3beds
2,692sqft
Single Family Residence
Built in 2004
2.78 Acres Lot
$678,700 Zestimate®
$237/sqft
$3,949 Estimated rent
Home value
$678,700
$577,000 - $794,000
$3,949/mo
Zestimate® history
Owner options
List your home for rent
$3,949/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$3,949/mo
Rent Zestimate®
Refinance and save
$3,649/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$3,649/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Primary suiteStone surround fireplacePrivate deckMature treesLoads of privacySeparate laundry roomCenter island
Zillow last checked:
Listing updated:
Listed by:
Team Rousseau Homes at Showcase Realty Inc,
Dawn Rousseau 203-217-6522,
Showcase Realty, Inc. 860-283-1298
Bought with:
Kim D'andrea, RES.0781717
William Pitt Sotheby's Int'l
Source: Smart MLS,MLS#: 24103515
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Bay/Bow Window, Bedroom Suite, French Doors, Full Bath, Walk-In Closet(s)
- Level: Main
- Area: 336 Square Feet
- Dimensions: 16 x 21
Bedroom
- Features: Walk-In Closet(s), Wall/Wall Carpet
- Level: Main
- Area: 156 Square Feet
- Dimensions: 12 x 13
Bedroom
- Features: Bay/Bow Window, Walk-In Closet(s), Wall/Wall Carpet
- Level: Main
- Area: 156 Square Feet
- Dimensions: 12 x 13
Primary bathroom
- Features: Full Bath, Stall Shower, Whirlpool Tub, Tile Floor
- Level: Main
Bathroom
- Level: Main
Bathroom
- Features: Tub w/Shower, Tile Floor
- Level: Main
Dining room
- Features: High Ceilings, Combination Liv/Din Rm, Hardwood Floor
- Level: Main
Kitchen
- Features: Built-in Features, Granite Counters, Dining Area, French Doors, Kitchen Island, Pantry
- Level: Main
- Area: 475 Square Feet
- Dimensions: 19 x 25
Living room
- Features: High Ceilings, Beamed Ceilings, Ceiling Fan(s), Entertainment Center, Fireplace, Hardwood Floor
- Level: Main
- Area: 589 Square Feet
- Dimensions: 19 x 31
Heating
- Forced Air, Propane
Cooling
- Ceiling Fan(s), Central Air
Appliances
- Included: Cooktop, Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Disposal, Electric Water Heater, Water Heater
- Laundry: Main Level
Features
- Wired for Sound
- Doors: French Doors
- Basement: Full,Interior Entry,Walk-Out Access,Concrete
- Attic: Pull Down Stairs
- Number of fireplaces: 2
Interior area
- Total structure area: 2,692
- Total interior livable area: 2,692 sqft
- Finished area above ground: 2,692
Property
Parking
- Total spaces: 8
- Parking features: Attached, Driveway, Garage Door Opener, Private, Paved
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Deck
- Exterior features: Rain Gutters, Lighting
Lot
- Size: 2.78 Acres
- Features: Secluded, Few Trees, Wooded, Level
Details
- Parcel number: 2478980
- Zoning: RR
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence
Materials
- HardiPlank Type
- Foundation: Concrete Perimeter
- Roof: Shingle
Condition
- New construction: No
- Year built: 2004
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Underground Utilities, Cable Available
Community & HOA
Community
- Features: Lake
- Subdivision: Winchester Center
HOA
- Has HOA: No
Location
- Region: Winsted
Financial & listing details
- Price per square foot: $237/sqft
- Tax assessed value: $287,070
- Annual tax amount: $8,374
- Date on market: 6/12/2025
- Exclusions: See Inclusion/Exclusion Rider
Price history
| Date | Event | Price |
|---|---|---|
| 7/31/2025 | Sold | $639,000+8.3%$237/sqft |
Source:  Smart MLS #24103515 Report a problem | ||
| 7/31/2025 | Pending sale | $589,900$219/sqft |
Source: Smart MLS #24103515 Report a problem | ||
| 6/12/2025 | Listed for sale | $589,900$219/sqft |
Source: Smart MLS #24103515 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $8,374 +10.5% | $287,070 |
| 2024 | $7,576 | $287,070 |
| 2023 | $7,576 -2.8% | $287,070 +23.5% |
| 2022 | $7,795 | $232,400 |
| 2021 | $7,795 | $232,400 |
| 2020 | $7,795 | $232,400 |
| 2019 | $7,795 | $232,400 |
| 2018 | $7,795 +1.5% | $232,400 +1.5% |
| 2017 | $7,682 | $229,040 |
| 2016 | $7,682 +2.6% | $229,040 |
| 2015 | $7,490 +2.5% | $229,040 |
| 2014 | $7,309 +2.3% | $229,040 |
| 2013 | $7,146 +2% | $229,040 -16.8% |
| 2012 | $7,003 | $275,380 |
| 2011 | $7,003 | $275,380 |
| 2010 | $7,003 +3.1% | $275,380 |
| 2009 | $6,794 | $275,380 |
| 2008 | $6,794 -5.6% | $275,380 +31.1% |
| 2007 | $7,197 +2.8% | $210,000 |
| 2006 | $7,001 | $210,000 |
Find assessor info on the county website
Neighborhood: 06098
Nearby homes
- $690,9003 bd2 ba2.9k sqft100 Hollow Hill Rd, Winsted, CT 06098Off Market
- $562,9003 bd2 ba2.5k sqft460 Platt Hill Rd, Winsted, CT 06098Off Market
- $637,2003 bd3 ba2.9k sqft470 Platt Hill Rd, Winsted, CT 06098Off Market
- $426,0003 bd3 ba1.4k sqft472 Platt Hill Rd, Winsted, CT 06098Off Market
- $572,4003 bd3 ba2.5k sqft458 Platt Hill Rd, Winsted, CT 06098Off Market
- $833,5003 bd2 ba4k sqft466 Platt Hill Rd, Winsted, CT 06098Off Market
- $404,1003 bd2 ba1.3k sqft111 Hollow Hill Rd, Winsted, CT 06098Off Market
- $620,4004 bd4 ba3.2k sqft456 Platt Hill Rd, Winsted, CT 06098Off Market
Nearby schools
GreatSchools rating
- NAMary P. Hinsdale SchoolGrades: PK-2Distance: 3.5 mi
- NAPearson AcademyGrades: Distance: 3.7 mi
- 6/10Pearson Middle SchoolGrades: 2-6Distance: 3.7 mi
Get pre-qualified for a loan
At Zillow Home Loans, we can pre-qualify you in as little as 5 minutes with no impact to your credit score.An equal housing lender. NMLS #10287.
Sell for more on Zillow
Get a Zillow Showcase℠ listing at no additional cost and you could sell for .
$678,700
2% more
+$13,574
With Zillow Showcase(estimated)
$692,274
- Connecticut
- Litchfield County
- Winchester
- 06098
- 102 Hollow Hill Road
Nearby cities
Nearby zip codes
Other Winchester Topics
