Homes for Sale Under 500K in Madison Town, CT

14 Homes for Sale

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Photo 3 of Single family home for sale at 18 Saint Francis Woods Rd, Madison, CT 06443 | MLS# 24204341 | Listing updated on 2026-09-16

Photo 1 of Single family home for sale at 18 Saint Francis Woods Rd, Madison, CT 06443 | MLS# 24204341 | Listing updated on 2026-09-16

Photo 2 of Single family home for sale at 18 Saint Francis Woods Rd, Madison, CT 06443 | MLS# 24204341 | Listing updated on 2026-09-16

$500,000

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3Bds

3Ba

1,824sqft

Single family home for sale

18 Saint Francis Woods Rd, Madison, CT 06443

Coldwell Banker Realty

Price Drop: $24.1K

Photo 3 of Single family home for sale at 35 Aileen Dr, Madison, CT 06443 | MLS# 24199405 | Listing updated on 2026-10-06

Photo 1 of Single family home for sale at 35 Aileen Dr, Madison, CT 06443 | MLS# 24199405 | Listing updated on 2026-10-06

Photo 2 of Single family home for sale at 35 Aileen Dr, Madison, CT 06443 | MLS# 24199405 | Listing updated on 2026-10-06

$499,900

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3Bds

2Ba

1,288sqft

Single family home for sale

35 Aileen Dr, Madison, CT 06443

William Raveis Real Estate

Photo 3 of Single family home for sale at 270 Scotland Rd, Madison, CT 06443 | MLS# 24210705 | Listing updated on 2026-10-06

Photo 1 of Single family home for sale at 270 Scotland Rd, Madison, CT 06443 | MLS# 24210705 | Listing updated on 2026-10-06

Photo 2 of Single family home for sale at 270 Scotland Rd, Madison, CT 06443 | MLS# 24210705 | Listing updated on 2026-10-06

$499,000

3Bds

2Ba

1,748sqft

Single family home for sale

270 Scotland Rd, Madison, CT 06443

William Raveis Real Estate

Photo 3 of Townhouse for sale at 23 Esterly Farms Rd #23, Madison, CT 06443 | MLS# 24203806 | Listing updated on 2026-09-24

Photo 1 of Townhouse for sale at 23 Esterly Farms Rd #23, Madison, CT 06443 | MLS# 24203806 | Listing updated on 2026-09-24

Photo 2 of Townhouse for sale at 23 Esterly Farms Rd #23, Madison, CT 06443 | MLS# 24203806 | Listing updated on 2026-09-24

$489,000

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2Bds

3Ba

1,606sqft

Townhouse for sale

23 Esterly Farms Rd #23, Madison, CT 06443

Coldwell Banker Realty

Price Drop: $32K

Photo 3 of Condo for sale at 6 Ladshaw Dr #6, Madison, CT 06443 | MLS# 24164028 | Listing updated on 2026-09-23

Photo 1 of Condo for sale at 6 Ladshaw Dr #6, Madison, CT 06443 | MLS# 24164028 | Listing updated on 2026-09-23

Photo 2 of Condo for sale at 6 Ladshaw Dr #6, Madison, CT 06443 | MLS# 24164028 | Listing updated on 2026-09-23

$455,000

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2Bds

2Ba

1,360sqft

Condo for sale

6 Ladshaw Dr #6, Madison, CT 06443

Houlihan Lawrence Wd

Photo 3 of Single family home for sale at 371 Race Hl Rd, Madison, CT 06443 | MLS# 24209422 | Listing updated on 2026-09-25

Photo 1 of Single family home for sale at 371 Race Hl Rd, Madison, CT 06443 | MLS# 24209422 | Listing updated on 2026-09-25

Photo 2 of Single family home for sale at 371 Race Hl Rd, Madison, CT 06443 | MLS# 24209422 | Listing updated on 2026-09-25

$425,000

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3Bds

2Ba

1,236sqft

Single family home for sale

371 Race Hl Rd, Madison, CT 06443

Colonial Properties Inc

Photo 3 of Single family home for sale at 35 Governors Way, Madison, CT 06443 | MLS# 24204125 | Listing updated on 2026-09-16

Photo 1 of Single family home for sale at 35 Governors Way, Madison, CT 06443 | MLS# 24204125 | Listing updated on 2026-09-16

Photo 2 of Single family home for sale at 35 Governors Way, Madison, CT 06443 | MLS# 24204125 | Listing updated on 2026-09-16

$382,500

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4Bds

2Ba

2,520sqft

Single family home for sale

35 Governors Way, Madison, CT 06443

Property Works New England

Photo 1 of Land for sale at 92 Scotland Rd #Lot. 3, Madison, CT 06443 | MLS# 24033986 | Listing updated on 2026-09-15

$350,000

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--Bds

--Ba

2.05acres lot

Land for sale

92 Scotland Rd #Lot. 3, Madison, CT 06443

Coldwell Banker Realty

Photo 3 of Single family home for sale at 42 Wildcat Rd, Madison, CT 06443 | MLS# 24142453 | Listing updated on 2026-09-15

Photo 1 of Single family home for sale at 42 Wildcat Rd, Madison, CT 06443 | MLS# 24142453 | Listing updated on 2026-09-15

Photo 2 of Single family home for sale at 42 Wildcat Rd, Madison, CT 06443 | MLS# 24142453 | Listing updated on 2026-09-15

$325,000

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3Bds

1Ba

1,080sqft

Single family home for sale

42 Wildcat Rd, Madison, CT 06443

Berkshire Hathaway Ne Prop.

Photo 3 of Single family home for sale at 40 East St, Madison, CT 06443 | MLS# 24197701 | Listing updated on 2026-08-22

Photo 1 of Single family home for sale at 40 East St, Madison, CT 06443 | MLS# 24197701 | Listing updated on 2026-08-22

Photo 2 of Single family home for sale at 40 East St, Madison, CT 06443 | MLS# 24197701 | Listing updated on 2026-08-22

$210,000

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1Bd

1Ba

732sqft

Single family home for sale

40 East St, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 3 of Single family home for sale at 32 North St, Madison, CT 06443 | MLS# 24170543 | Listing updated on 2026-09-23

Photo 1 of Single family home for sale at 32 North St, Madison, CT 06443 | MLS# 24170543 | Listing updated on 2026-09-23

Photo 2 of Single family home for sale at 32 North St, Madison, CT 06443 | MLS# 24170543 | Listing updated on 2026-09-23

$164,999

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2Bds

1Ba

592sqft

Single family home for sale

32 North St, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Land for sale at Skytop Dr, Madison, CT 06443 | MLS# 24128072 | Listing updated on 2026-09-15

$159,900

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--Bds

--Ba

1.43acres lot

Land for sale

Skytop Dr, Madison, CT 06443

Ssg Real Estate Llc

Photo 3 of Single family home for sale at 92 4th Avenue, Madison, CT 06443 | MLS# 24168727 | Listing updated on 2026-07-14

Photo 1 of Single family home for sale at 92 4th Avenue, Madison, CT 06443 | MLS# 24168727 | Listing updated on 2026-07-14

Photo 2 of Single family home for sale at 92 4th Avenue, Madison, CT 06443 | MLS# 24168727 | Listing updated on 2026-07-14

$142,900

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2Bds

1Ba

396sqft

Single family home for sale

92 4th Avenue, Madison, CT 06443

William Pitt Sotheby'S Int'L

Hot

Price Drop: $13K

Photo 3 of Single family home for sale at 16 North St, Madison, CT 06443 | MLS# 24160104 | Listing updated on 2026-09-14

Photo 1 of Single family home for sale at 16 North St, Madison, CT 06443 | MLS# 24160104 | Listing updated on 2026-09-14

Photo 2 of Single family home for sale at 16 North St, Madison, CT 06443 | MLS# 24160104 | Listing updated on 2026-09-14

$125,000

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1Bd

1Ba

476sqft

Single family home for sale

16 North St, Madison, CT 06443

Real Broker Ct, Llc

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No. of Homes

Single Family Homes for Sale in Madison Town

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Historic Homes for Sale Madison Town

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1 Bedroom Homes for Sale in Madison Town, CT

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Houses for Sale in Madison Town Under $100K

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Based on information provided to and compiled by the SMART MLS, Inc. through Oct 8, 2026, 7:30 AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.