258 Flanders Road

Closed 9/21/22
Closed 9/21/22
Gallery Image 1
Sold
Last Sold Price
$650,000
4 beds3,210 sqft$202/sqft
258 Flanders Rd, Woodbury, CT 06798
Single FamilyProperty Type
5.92 acresLot Size
1992Year Built
$202/sq ftPrice per sq ft
2 carsParking Spaces

Description

Meander up your drive, past the neighboring picturesque horse paddocks to this private oasis tucked amongst just under six acres of nature with gunite pool and spa, oversized wrap decking and a large screened porch. No need to leave unless you take the few minute trip into historic Woodbury town center to enjoy all this little town has to offer. Expansive, remodeled kitchen opens to family room with fireplace number one, steps right into the screened porch. Formal front living room with fireplace...Meander up your drive, past the neighboring picturesque horse paddocks to this private oasis tucked amongst just under six acres of nature with gunite pool and spa, oversized wrap decking and a large screened porch. No need to leave unless you take the few minute trip into historic Woodbury town center to enjoy all this little town has to offer. Expansive, remodeled kitchen opens to family room with fireplace number one, steps right into the screened porch. Formal front living room with fireplace number two, and a large dining room with wet bar/ butlers pantry and large - very large, built in china closet. Convenient mud room / laundry room between garage and kitchen. Upstairs.....step down into master bedroom wing with two skylights and two dormers to let the sunshine dance thru. Master bath with sunken jetted tub, new double sink granite topped vanity and walk in closet. Three additional bedrooms all have walk in closets. Hardwood flooring on both levels. Central Vacuum, security system. Brand new gas pool heater, generac generator, top of the line furnace. Just in case you need more space, the full walk out lower level could be finished for a great recreation room/ movie theatre.
  • Listed by: Mary Ann Bennett 203.263.4336 maryann@drakeley.com • Drakeley Real Estate, Inc.
Listing closed: 09/21/2022 12:00 AM • Source: SMARTMLS, MLS#: 170499443

Recent comparable sales

Median sold price

$665,000

Avg days on market

68

Sale-to-list ratio

94.2%

Woodbury, CT

9 comparable properties found

$850,000 | 99 Plumb Brook Road, Woodbury, CT 06798
1

$850,000

Sold 06/03/26

4
Bedrooms
3,330
Square Feet
2.93
Acres

99 Plumb Brook Road, Woodbury, CT 06798

2

$560,000

Sold 07/23/25

4
Bedrooms
2.5
Bathrooms
2,609
Square Feet
1.47
Acres

34 Quail Run Road, Woodbury, CT 06798

$632,500 | 97 Hard Hill Road, Woodbury, CT 06798
3

$632,500

Sold 11/12/24

4
Bedrooms
3,022
Square Feet
1.39
Acres

97 Hard Hill Road, Woodbury, CT 06798

$595,000 | 40 Quanopaug Trail, Woodbury, CT 06798
4

$595,000

Sold 01/13/25

4
Bedrooms
2,524
Square Feet
2.02
Acres

40 Quanopaug Trail, Woodbury, CT 06798

$665,000 | 174 Weekeepeemee Road, Woodbury, CT 06798
5

$665,000

Sold 01/16/26

4
Bedrooms
3,064
Square Feet
5.38
Acres

174 Weekeepeemee Road, Woodbury, CT 06798

$550,000 | 212 Main Street North, Woodbury, CT 06798
6

$550,000

Sold 11/21/25

4
Bedrooms
2,861
Square Feet
2.1
Acres

212 Main Street North, Woodbury, CT 06798

$775,000 | 6 Strong Field Road, Woodbury, CT 06798
7

$775,000

Sold 11/13/25

4
Bedrooms
2,600
Square Feet
0.98
Acres

6 Strong Field Road, Woodbury, CT 06798

$765,000 | 393 Middle Rd Turnpike, Woodbury, CT 06798
8

$765,000

Sold 12/22/25

4
Bedrooms
3,280
Square Feet
6.25
Acres

393 Middle Rd Turnpike, Woodbury, CT 06798

a house view with a outdoor space
9

$740,000

Sold 08/01/25

4
Bedrooms
3,341
Square Feet
2.02
Acres

101 Railtree Hill Road, Woodbury, CT 06798

Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Drakeley Real Estate, Inc., Mary Ann Bennett

Sold By William Pitt Sotheby's Int'l, Lenore Mallett

Add your commute

Payment Calculator

Get preapproved with Rocket Mortgage1

$4,093 per month

30 year fixed, 6.71% Interest

Principal and Interest

$3,359

Property Taxes

$734

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 258 Flanders Road

Property Details
  • Taxes: $8,813 / year
  • MLS Type: Residential
  • County: Litchfield County
  • Basement Description: Full With Walk-Out
  • Direct Waterfront: No
  • Garages Number: 2
  • Neighborhood: Flanders
  • Style: Colonial
  • Garage Parking Info: Attached Garage
  • Swimming Pool: Yes
Building Information
  • Year Built: 1992
  • Lot Size: 5.92 AC / 257,875 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Main Street to Flanders home on right.
  • Elementary School: Mitchell
  • High School: Nonnewaug
  • Latitude: 41.576187
  • Longitude: -73.199394
  • Middle Jr High School: Woodbury
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Park, Private Rec Facilities, Private School(s)
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Special Association Assessment: No
  • Property Tax: $8,813
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Patio, Porch-Screened, Wrap Around Deck
  • Pool Description: In Ground Pool, Spa, Heated, Gunite
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Storage Space
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Security System
  • Laundry Room Info: Main Level
  • Laundry Room Location: Laundry/mud rm in between garage and kit
  • Rooms Additional: Foyer, Laundry Room
  • Room Count: 8
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Hardwood Floor,Wet Bar
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Breakfast Bar,Granite Counters,Hardwood Floor,Pantry,Remodeled
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 4
  • Room Entry Order: 4
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 5
  • Room Entry Order: 5
  • Room Features: Hardwood Floor,Skylight,Sunken,Walk-In Closet,Whirlpool Tub
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 6
  • Room Entry Order: 6
  • Room Features: Hardwood Floor,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: Hardwood Floor,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Features: Hardwood Floor,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: Dusty Blue
  • Construction Description: Frame
  • Driveway Type: Private, Asphalt
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1992
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 3210
Lot Information
  • Lot Description: Interior Lot, Treed
  • Parcel Number: 933240
  • Sq Ft Est Heated Above Grade: 3210.0
  • Sq Ft Total: 3210.0
  • Zoning: OS100
Utilities
  • Energy Features: Generator, Storm Doors, Thermopane Windows
  • Heat Fuel Type: Oil
  • Hot Water Description: Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 258 Flanders Road

DateEvent & SourcePriceAppreciation
Sep 17, 2022

Closed (Public Record)

Public Record #1498159383

$650,000

+5.3% / yr

Sep 10, 2014

Closed (Public Record)

Public Record #441330700

$430,000

-0.7% / yr

Aug 30, 2000

Closed (Public Record)

Public Record #91983723

$475,000—
DateEvent & SourcePrice
09/17/2022

Closed (Public Record)

Public Record #1498159383

$650,000

+5.3% / yr

09/10/2014

Closed (Public Record)

Public Record #441330700

$430,000

-0.7% / yr

08/30/2000

Closed (Public Record)

Public Record #91983723

$475,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 258 Flanders Road

Taxable ValueLand$61,810Additions$370,930Total$432,740
Tax Record2025$10,221 ($852 / month)
Home Facts
Beds4Baths2.5Total Finished SqFt3,210 SqFtAbove Grade Finished SqFt3,210 SqFtUnfinished Basement SqFt1,614 SqFtStories2Lot Size257,875 SqFtStyleSingle Family ResidenceYear Built1992Year Renovated2004ZoningOS100CountyNAUGATUCK VALLEYAPNWOOD M:025 B:021D L:3

Schools near 258 Flanders Road

This home is within Regional School District 14.
Rating
School
Type
Grades
Distance
Bethlehem Elementary School
Public - PK to 5
Mitchell Elementary School
Public - PK to 5
Woodbury Middle School
Public - 6 to 8
Nonnewaug High School
Public - 9 to 12
Rating
School
Distance
Bethlehem Elementary School
PublicPK to 5

Mitchell Elementary School
PublicPK to 5

Woodbury Middle School
Public6 to 8

Nonnewaug High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

New listings in 06798

$555,000 | 33 Hurds Hill Road, Woodbury, CT 06798
1/38
Open: 9/13 11:00AM - 01:00PM

$555,000

5
Bedrooms
4,130
Square Feet
1.46
Acres

33 Hurds Hill Road, Woodbury, CT 06798

$209,900 | 229 Bacon Pond Road, Unit 313, Woodbury, CT 06798
1/22

$209,900

2
Bedrooms
913
Square Feet

229 Bacon Pond Road, Unit 313, Woodbury, CT 06798

$765,000 | 31 Bethwood Lane, Woodbury, CT 06798
1/27

$765,000

2
Bedrooms
1,814
Square Feet
2.5
Acres

31 Bethwood Lane, Woodbury, CT 06798

$289,900 | 6 Upper Commons, Unit 6, Woodbury, CT 06798
1/12
Coming Soon

$289,900

3
Bedrooms
2,247
Square Feet

6 Upper Commons, Unit 6, Woodbury, CT 06798

$519,000 | 50 Washington Road, Woodbury, CT 06798
1/40
Open: 9/12 12:00PM - 02:00PM

$519,000

3
Bedrooms
1,550
Square Feet
0.48
Acres

50 Washington Road, Woodbury, CT 06798

$699,900 | 201 Transylvania Road, Woodbury, CT 06798
1/23
Listed By Coldwell Banker Realty

$699,900

3
Bedrooms
2,451
Square Feet
2.31
Acres

201 Transylvania Road, Woodbury, CT 06798

$420,000 | 34 Pilgrim Trail, Woodbury, CT 06798
1/34
Virtual Tour

$420,000

4
Bedrooms
1,590
Square Feet
1.74
Acres

34 Pilgrim Trail, Woodbury, CT 06798

$699,000 | 61 Minortown Road, Woodbury, CT 06798
1/40
Listed By Coldwell Banker Realty

$699,000

3
Bedrooms
2,081
Square Feet
2.92
Acres

61 Minortown Road, Woodbury, CT 06798

$875,000 | 385 Middle Rd Turnpike, Woodbury, CT 06798
1/40
Under Contract - Continue To ShowVirtual Tour

$875,000

4
Bedrooms
2,394
Square Feet
3.29
Acres

385 Middle Rd Turnpike, Woodbury, CT 06798

Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 258 Flanders Road, Woodbury, CT 06798
$650,000
4
3,210
257,875
266 Flanders Road, Woodbury, CT 06798
$645,000
3
3,630
219,978
250 Flanders Road, Woodbury, CT 06798
–
–
–
–
173,804
234 Flanders Road, Woodbury, CT 06798
–
3
3
3,613
1,711,037
222 Flanders Road, Woodbury, CT 06798
–
3
2
2,340
602,870
278 Flanders Road, Woodbury, CT 06798
$317,000
4
2,112
176,418

Explore Nearby Homes

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Drakeley Real Estate, Inc., Mary Ann Bennett

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.