Price Drop: $495K

Photo 1 of Mansion for sale at 45 Island Ave, Madison, CT 06443 | MLS# 24166497 | Listing updated on 2026-09-25

$3,000,000

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5Bds

6Ba

5,657sqft

Mansion for sale

45 Island Ave, Madison, CT 06443

Coldwell Banker Realty

Photo 1 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

Price Drop: $55K

Photo 1 of Single family home for sale at 92 Scotland Ave, Madison, CT 06443 | MLS# 24145947 | Listing updated on 2026-09-28

$2,195,000

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5Bds

5Ba

4,143sqft

Single family home for sale

92 Scotland Ave, Madison, CT 06443

Wollman Realty

Price Drop: $80K

Photo 1 of Single family home for sale at 23 Sheep Pasture Rd, Madison, CT 06443 | MLS# 24147939 | Listing updated on 2026-09-15

$2,215,000

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4Bds

6Ba

4,700sqft

Single family home for sale

23 Sheep Pasture Rd, Madison, CT 06443

Wollman Realty

Photo 1 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 1 of Single family home for sale at 30 Meeting House Ln, Madison, CT 06443 | MLS# 24173597 | Listing updated on 2026-09-15

$1,695,000

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5Bds

4Ba

3,912sqft

Single family home for sale

30 Meeting House Ln, Madison, CT 06443

Coldwell Banker Realty

Photo 1 of Single family home for sale at 81 Strawberry Hl Rd, Madison, CT 06443 | MLS# 24155109 | Listing updated on 2026-09-15

$1,975,000

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4Bds

4Ba

2,850sqft

Single family home for sale

81 Strawberry Hl Rd, Madison, CT 06443

Coldwell Banker Realty

Photo 1 of Single family home for sale at Bushnell Ln, Madison, CT 06443 | MLS# 24041459 | Listing updated on 2026-09-14

$1,250,000

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2Bds

4Ba

2,000sqft

Single family home for sale

Bushnell Ln, Madison, CT 06443

Coldwell Banker Realty

Hot

Price Drop: $13K

Photo 1 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

Photo 1 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

Price Drop: $32K

Photo 1 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

Price Drop: $100K

Photo 1 of Single family home for sale at 26 Bassett Ln, Madison, CT 06443 | MLS# 24177522 | Listing updated on 2026-10-05

$1,850,000

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3Bds

4Ba

2,160sqft

Single family home for sale

26 Bassett Ln, Madison, CT 06443

Beycome Of Connecticut

Photo 1 of Condo for sale at 10 Runnymede Ln #10, Madison, CT 06443 | MLS# 24160683 | Listing updated on 2026-10-06

$595,000

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2Bds

2Ba

2,560sqft

Condo for sale

10 Runnymede Ln #10, Madison, CT 06443

William Raveis Real Estate

Photo 1 of Single family home for sale at (Undisclosed), Madison, CT 06443 | MLS# 24168959 | Listing updated on 2026-04-23

$2,379,000

4Bds

6Ba

5,126sqft

Single family home for sale

(Undisclosed), Madison, CT 06443

William Pitt Sotheby'S Int'L

Price Drop: $100K

Photo 1 of Single family home for sale at 24 Indigo Trl, Madison, CT 06443 | MLS# 24159028 | Listing updated on 2026-09-28

$2,550,000

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4Bds

5Ba

6,194sqft

Single family home for sale

24 Indigo Trl, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 3 Arrowhead Rd, Madison, CT 06443 | MLS# 24136720 | Listing updated on 2026-09-24

$875,000

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3Bds

4Ba

2,160sqft

Single family home for sale

3 Arrowhead Rd, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 31 Stony Ln Lot 2 Rd, Madison, CT 06443 | MLS# 24004631 | Listing updated on 2026-10-06

$1,890,000

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4Bds

4Ba

3,400sqft

Single family home for sale

31 Stony Ln Lot 2 Rd, Madison, CT 06443

William Raveis Real Estate

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 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 1 of Single family home for sale at 273 Horse Pond Rd, Madison, CT 06443 | MLS# 24210111 | Listing updated on 2026-10-05

$600,000

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5Bds

2Ba

2,240sqft

Single family home for sale

273 Horse Pond Rd, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 32 Wellsweep Dr, Madison, CT 06443 | MLS# 24209740 | Listing updated on 2026-10-07

$669,000

3Bds

3Ba

2,000sqft

Single family home for sale

32 Wellsweep Dr, Madison, CT 06443

Berkshire Hathaway Ne Prop.

Photo 1 of Multi family home for sale at 1209 Durham Rd, Madison, CT 06443 | MLS# 24211566 | Listing updated on 2026-10-02

$999,000

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5Bds

5Ba

3,800sqft

Multi family home for sale

1209 Durham Rd, Madison, CT 06443

Berkshire Hathaway Ne Prop.

Photo 1 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

Price Drop: $51K

Photo 1 of Single family home for sale at 148 Mungertown Rd, Madison, CT 06443 | MLS# 24205471 | Listing updated on 2026-10-06

$1,149,000

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4Bds

4Ba

2,354sqft

Single family home for sale

148 Mungertown Rd, Madison, CT 06443

William Raveis Real Estate

Photo 1 of Single family home for sale at 87 Wildcat Springs Dr, Madison, CT 06443 | MLS# 24208958 | Listing updated on 2026-10-07

$1,600,000

4Bds

4Ba

3,665sqft

Single family home for sale

87 Wildcat Springs Dr, Madison, CT 06443

William Raveis Real Estate

Photo 1 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 1 of Townhouse for sale at 67 Boston Post Rd #15, Madison, CT 06443 | MLS# 24208016 | Listing updated on 2026-10-01

$650,000

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2Bds

2Ba

1,838sqft

Townhouse for sale

67 Boston Post Rd #15, Madison, CT 06443

William Pitt Sotheby'S Int'L

Price Drop: $24.1K

Photo 1 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 1 of Single family home for sale at 107 Randi Dr, Madison, CT 06443 | MLS# 24208709 | Listing updated on 2026-10-02

$1,650,000

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4Bds

5Ba

4,756sqft

Single family home for sale

107 Randi Dr, Madison, CT 06443

Compass Connecticut, Llc

Photo 1 of Single family home for sale at 3 Little Holw Rd, Madison, CT 06443 | MLS# 24205125 | Listing updated on 2026-09-24

$795,000

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4Bds

3Ba

2,572sqft

Single family home for sale

3 Little Holw Rd, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 118 River Rd, Madison, CT 06443 | MLS# 24192754 | Listing updated on 2026-10-06

$5,000,000

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3Bds

3Ba

3,109sqft

Single family home for sale

118 River Rd, Madison, CT 06443

William Raveis Real Estate

Price Drop: $9.1K

Photo 1 of Single family home for sale at 7 Milestone Ln, Madison, CT 06443 | MLS# 24195695 | Listing updated on 2026-09-20

$699,900

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4Bds

3Ba

2,456sqft

Single family home for sale

7 Milestone Ln, Madison, CT 06443

Coldwell Banker Realty

Photo 1 of Condo for sale at 29 Wilshire Rd #29, Madison, CT 06443 | MLS# 24178656 | Listing updated on 2026-09-20

$565,000

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2Bds

2Ba

1,280sqft

Condo for sale

29 Wilshire Rd #29, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 150 Race Hl Rd, Madison, CT 06443 | MLS# 24208079 | Listing updated on 2026-10-06

$849,000

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4Bds

3Ba

2,792sqft

Single family home for sale

150 Race Hl Rd, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 373 Boston Post Rd, Madison, CT 06443 | MLS# 24207210 | Listing updated on 2026-10-04

$2,675,000

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4Bds

5Ba

4,766sqft

Single family home for sale

373 Boston Post Rd, Madison, CT 06443

William Pitt Sotheby'S Int'L

Price Drop: $99.1K

Photo 1 of Single family home for sale at 42 Concord Dr, Madison, CT 06443 | MLS# 24206829 | Listing updated on 2026-10-07

$799,900

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4Bds

3Ba

3,170sqft

Single family home for sale

42 Concord Dr, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 343 Horse Pond Rd, Madison, CT 06443 | MLS# 24207706 | Listing updated on 2026-10-04

$675,000

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3Bds

3Ba

2,138sqft

Single family home for sale

343 Horse Pond Rd, Madison, CT 06443

William Pitt Sotheby'S Int'L

Price Drop: $20K

Photo 1 of Single family home for sale at 2125 Durham Rd, Madison, CT 06443 | MLS# 24195345 | Listing updated on 2026-10-06

$749,900

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4Bds

4Ba

3,056sqft

Single family home for sale

2125 Durham Rd, Madison, CT 06443

William Raveis Real Estate

Photo 1 of Single family home for sale at 77 Hickory Ln, Madison, CT 06443 | MLS# 24207730 | Listing updated on 2026-09-28

$1,250,000

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4Bds

5Ba

4,421sqft

Single family home for sale

77 Hickory Ln, Madison, CT 06443

William Pitt Sotheby'S Int'L

Photo 1 of Single family home for sale at 39 Mill Rd, Madison, CT 06443 | MLS# 24206863 | Listing updated on 2026-09-17

$625,000

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5Bds

2Ba

2,688sqft

Single family home for sale

39 Mill Rd, Madison, CT 06443

William Pitt Sotheby'S Int'L

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

$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

Photo 1 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

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Based on information provided to and compiled by the SMART MLS, Inc. through Oct 7, 2026, 11:30 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.

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