Recently Viewed Properties
See This Home
Save This Listing
Close

$575,000

  • Sold
  • Closed
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 2,108 Sq. Ft.
  • Updated 7 days ago
See This Home
Save This Home
See This Home
Save This Home
Direct Housatonic River waterfront living! This beautifully updated home is officially recorded as a 2-bedroom, 2-full-bath residence offering 2,104 total sq. ft. of heated living space, including 1,530 sq. ft. above grade plus 574 heated sq. ft. in the partially finished walk-out lower level. Hardwood floors, a renovated kitchen and bright living spaces welcome you inside. Downstairs, one finished room is currently utilized as additional sleeping space, conveniently located beside a full bath and walk-out, while an adjoining room serves as a podcast/media studio. Officially listed as a 2-bedroom, the flexible lower level offers endless possibilities for guests, office, gym, studio or playroom. Outside, over $100,000 in recent deck, patio and river-facing improvements have transformed the waterfront into an incredible extension of the home. Entertain overlooking the river, enjoy quiet mornings by the water or head down to two private docks for direct Housatonic access. A detached 1-car garage, central air, tankless propane hot water and fully owned, paid-off solar panels with no lease or loan to assume add even more value. Extensively improved inside and out, with two private docks and an impressive 120' of direct Housatonic River frontage, this property makes the most of its exceptional waterfront setting.

Full Property Details for 5 Roosevelt Dr

General

  • Sold For: $575,000
  • Taxes: (July 2026-June 2027)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24203247
  • Added to Site: 58 day(s) ago

Interior

  • Number of Rooms: 4
  • Appliances: Oven/Range, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2
  • Primary Bedroom: Primary Bedroom, Upper
  • Bedroom 1: Bedroom, Upper

Other Rooms

  • Living Room: Living Room, Main
  • Eat In Kitchen: Eat-In Kitchen, Main
  • Dining Room: Dining Room, Main
  • Game room: Yes
  • Game Room: Rec/Play Room, Lower
  • Rec Room: Lower
  • Theater/Media: Media Room, Lower
  • Laundry: Main Level

Exterior

  • Exterior Features: Porch, Deck, Gutters, Garden Area, Lighting, Stone Wall, Patio

Location

  • County: New Haven
  • Neighborhood: Squantuck
  • Driving Directions: Use GPS. 5 Roosevelt Drive, Seymour, CT 06483

School Information

  • Elementary School: Bungay
  • High School: Seymour

Community

  • Community Name: Squantuck

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Propane
  • Heating Fuel: Propane
  • Water Heater: Propane, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Partial, Storage, Interior Access, Partially Finished, Walk-out, Partial With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 2,108
  • Above Ground: 1,530 Sq. Ft.
  • Below Ground: 578 Sq. Ft.
  • Year Built: 1948

Lot Features

  • Lot Size (Acres): 0.13
  • Zoning: RC-3
  • Lot Description: Fence - Full, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: River, Dock or Mooring, View

Green Features

  • Energy Features: Active Solar, Generator Ready, Programmable Thermostat, Storm Doors, Thermopane Windows

Financial Considerations

  • Assessment Amount: $304,710
  • Tax Year: July 2026-June 2027

Disclosures and Reports

  • Property ID: 1319099

Meet the listing agent

Meet the listing agent
— 5 Roosevelt Dr —

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 5 Roosevelt Dr

School District:Seymour School District
NameGradesDistance
Bungay School
35 Bungay Road, Seymour, CT 06483
K-53.3 mi
Seymour Middle School
211 Mountain Road, Seymour, CT 06483
6-82.2 mi
Seymour High School
2 Botsford Road, Seymour, CT 06483
9-122.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5 Roosevelt Dr

Date
Details
Price
Change
Source
10/22/2026
Sold
$575,000
-0.69%
MLS
9/03/2026
Listed
$579,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Similar Properties near 5 Roosevelt Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

52 Buckingham Rd, Seymour, CT 06483 - Photo 1 Just Listed
$599,000
Open House

52 Buckingham Rd  Seymour, CT 06483

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 5
    Total Baths
  • 2,161
    Sq. Ft.
Listed by William Raveis Real Estate
66 E St, Derby, CT 06418 - Photo 1
$580,000

66 E St  Derby, CT 06418

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,276
    Sq. Ft.
Listed by Coldwell Banker Bivins Realty
121 Longfellow Rd, Shelton, CT 06484 - Photo 1
$525,000

121 Longfellow Rd  Shelton, CT 06484

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,716
    Sq. Ft.
Listed by BHGRE Gaetano Marra Homes
61 Soundview Ave, Shelton, CT 06484 - Photo 1
$549,999

61 Soundview Ave  Shelton, CT 06484

  • Single Family
  • Active
  • Updated 13 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 2,588
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l

Just Listed near 5 Roosevelt Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

4 Avon Ct, Beacon Falls, CT 06403 - Photo 1 Just Listed
$249,900

4 Avon Ct  #4  Beacon Falls, CT 06403

  • Townhouse
  • Active
  • Updated 14 hours ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,218
    Sq. Ft.
Listed by Ken Viele (203) 605-4251
26 Cedar Cir, Beacon Falls, CT 06403 - Photo 1 Just Listed
$448,500
Open House

26 Cedar Cir  Beacon Falls, CT 06403

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 1,872
    Sq. Ft.
Listed by Ken Viele (203) 605-4251
53 Cotton Hollow Rd, Beacon Falls, CT 06403 - Photo 1 Just Listed
$629,900

53 Cotton Hollow Rd  Beacon Falls, CT 06403

  • Multi-Family
  • Active
  • Updated 1 day ago
  • 6
    Total Beds
Listed by Continental Real Estate
37 Quarry Rd, Beacon Falls, CT 06403 - Photo 1 Just Listed
$39,900

37 Quarry Rd  Beacon Falls, CT 06403

  • Land Residential
  • Active
  • Updated 4 days ago
  • 0.19
    Acres
Listed by SB Realty Group, LLC

Price Reduced near 5 Roosevelt Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

3 Patricia Terrace, Beacon Falls, CT 06403 - Photo 1 Price Reduced
-$15,000 (-2.86%)
$510,000
Open House

3 Patricia Terrace  Beacon Falls, CT 06403

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,880
    Sq. Ft.
Listed by Tom Pitney (203) 736-3691
403-405 Skokorat Rd, Beacon Falls, CT 06403 - Photo 1 Price Reduced
-$20,000 (-4.04%)
$475,000

403-405 Skokorat Rd  Beacon Falls, CT 06403

  • Single Family
  • Active
  • Updated 6 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,852
    Sq. Ft.
Listed by Lamacchia Realty
[Address not provided], Beacon Falls, CT 06403 - Photo 1 Price Reduced
-$1,000 (-18.18%)
$4,500

[Address not provided]  Beacon Falls, CT 06403

  • Commercial Lease
  • Active
Listed by GT Properties
21 Platt St, Ansonia, CT 06401 - Photo 1 Price Reduced
-$35,100 (-8.07%)
$399,900
Open House

21 Platt St  Ansonia, CT 06401

  • Single Family
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 1
    Total Bath
  • 1,519
    Sq. Ft.
Listed by Sharon Perugini (475) 689-5665

Recent Sales near 5 Roosevelt Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

3 Roosevelt Dr, Seymour, CT 06483 - Photo 1 Sold
$506,500

3 Roosevelt Dr  Seymour, CT 06483

  • Single Family
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,431
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by Unrepresented Buyer
8 Buckingham Rd, Derby, CT 06418 - Photo 1 Sold
$655,000

8 Buckingham Rd  Derby, CT 06418

  • Single Family
  • Closed
  • 3
    Beds
  • 5
    Total Baths
  • 2,880
    Sq. Ft.
Listed by KW Legacy Partners
Sold by Vylla Home (CT) LLC
85 Buckingham Rd, Seymour, CT 06483 - Photo 1 Sold
$550,000

85 Buckingham Rd  Seymour, CT 06483

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,792
    Sq. Ft.
Listed by Realty ONE Group Connect
Sold by Preston Gray Real Estate
154 S Benham Rd, Seymour, CT 06483 - Photo 1 Sold
$550,000

154 S Benham Rd  Seymour, CT 06483

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 4,664
    Sq. Ft.
Listed and Sold by Dave Jones Realty, LLC

5 Roosevelt Drive, Seymour, CT 06483 (MLS# 24203247) is a Single Family property that was sold at $575,000 on October 22, 2026. This property was listed by Nick Wilson from our Oxford Office.Want to learn more about 5 Roosevelt Drive? Do you have questions about finding other Single Family real estate for sale in Seymour? You can browse all Seymour real estate or contact a Coldwell Banker agent to request more information.