Photo 3 of Single family home for sale at 111 Ayr Rd, Chester Town, NY 10918 | MLS# 1049653 | Listing updated on 2026-10-07

Photo 1 of Single family home for sale at 111 Ayr Rd, Chester Town, NY 10918 | MLS# 1049653 | Listing updated on 2026-10-07

Photo 2 of Single family home for sale at 111 Ayr Rd, Chester Town, NY 10918 | MLS# 1049653 | Listing updated on 2026-10-07

$599,000

count-img 8

4Bds

5Ba

3,326sqft

Single family home for sale

111 Ayr Rd, Chester Town, NY 10918

Curasi Realty, Inc.

Hot

Photo 3 of Single family home for sale at 123 Pickerel Rd, Chester Town, NY 10950 | MLS# 1052929 | Listing updated on 2026-10-01

Photo 1 of Single family home for sale at 123 Pickerel Rd, Chester Town, NY 10950 | MLS# 1052929 | Listing updated on 2026-10-01

Photo 2 of Single family home for sale at 123 Pickerel Rd, Chester Town, NY 10950 | MLS# 1052929 | Listing updated on 2026-10-01

$599,000

count-img 13

4Bds

3Ba

2,082sqft

Single family home for sale

123 Pickerel Rd, Chester Town, NY 10950

Century 21 Realty Center

Photo 3 of Single family home for sale at 161 Highland Ave, Chester Town, NY 10950 | MLS# 1059180 | Listing updated on 2026-10-07

Photo 1 of Single family home for sale at 161 Highland Ave, Chester Town, NY 10950 | MLS# 1059180 | Listing updated on 2026-10-07

Photo 2 of Single family home for sale at 161 Highland Ave, Chester Town, NY 10950 | MLS# 1059180 | Listing updated on 2026-10-07

$595,000

count-img 3

3Bds

2Ba

1,842sqft

Single family home for sale

161 Highland Ave, Chester Town, NY 10950

Exp Realty

3D Tour

Photo 3 of Sale Pending at 6 Adams Ct, Monroe, NY 10950 | MLS# 977377 | Listing updated on 2026-07-10

Photo 1 of Sale Pending at 6 Adams Ct, Monroe, NY 10950 | MLS# 977377 | Listing updated on 2026-07-10

Photo 2 of Sale Pending at 6 Adams Ct, Monroe, NY 10950 | MLS# 977377 | Listing updated on 2026-07-10

$585,000

count-img 7

4Bds

2Ba

2,056sqft

Sale Pending

6 Adams Ct, Monroe, NY 10950

Keller Williams Realty

$575,000

count-img 5

6Bds

2Ba

--sqft

Multi family home for sale

68 Conklingtown Rd

68 Conklingtown Rd #1 & 2, Chester Town, NY 10918

Ms Realty Group Usa, Inc

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 68 Conklingtown Rd, Chester Town, NY 10918 - Unit #1 & 2

Unit #1 & 2

68 Conklingtown Rd

$575,000 - $575,000

68 Conklingtown Rd, Chester Town, NY 10918

4+ Beds

$575k+

Photo 3 of Sale Pending at 7 Lakeview Dr, Goshen, NY 10924 | MLS# 1028872 | Listing updated on 2026-09-16

Photo 1 of Sale Pending at 7 Lakeview Dr, Goshen, NY 10924 | MLS# 1028872 | Listing updated on 2026-09-16

Photo 2 of Sale Pending at 7 Lakeview Dr, Goshen, NY 10924 | MLS# 1028872 | Listing updated on 2026-09-16

$549,999

count-img 6

4Bds

3Ba

2,098sqft

Sale Pending

7 Lakeview Dr, Goshen, NY 10924

Howard Hanna Rand Realty

Photo 3 of Sale Pending at 44 Wilson Rd, Chester Town, NY 10950 | MLS# 1016146 | Listing updated on 2026-09-11

Photo 1 of Sale Pending at 44 Wilson Rd, Chester Town, NY 10950 | MLS# 1016146 | Listing updated on 2026-09-11

Photo 2 of Sale Pending at 44 Wilson Rd, Chester Town, NY 10950 | MLS# 1016146 | Listing updated on 2026-09-11

$549,000

count-img 10

3Bds

3Ba

2,374sqft

Sale Pending

44 Wilson Rd, Chester Town, NY 10950

Keller Williams Realty

3D Tour

Photo 3 of Sale Pending at 150 Lake Region Blvd, Monroe, NY 10950 | MLS# 955186 | Listing updated on 2026-08-19

Photo 1 of Sale Pending at 150 Lake Region Blvd, Monroe, NY 10950 | MLS# 955186 | Listing updated on 2026-08-19

Photo 2 of Sale Pending at 150 Lake Region Blvd, Monroe, NY 10950 | MLS# 955186 | Listing updated on 2026-08-19

$549,000

count-img 6

4Bds

3Ba

2,112sqft

Sale Pending

150 Lake Region Blvd, Monroe, NY 10950

Hudson Valley Home Connection

Hot

Photo 3 of Single family home for sale at 19 Meadow Ave, Chester Town, NY 10918 | MLS# 1050131 | Listing updated on 2026-09-25

Photo 1 of Single family home for sale at 19 Meadow Ave, Chester Town, NY 10918 | MLS# 1050131 | Listing updated on 2026-09-25

Photo 2 of Single family home for sale at 19 Meadow Ave, Chester Town, NY 10918 | MLS# 1050131 | Listing updated on 2026-09-25

$525,000

count-img 14

2Bds

2Ba

1,910sqft

Single family home for sale

19 Meadow Ave, Chester Town, NY 10918

Re/Max Town & Country

Hot

Photo 3 of Single family home for sale at 24 Walnut St, Chester, NY 10918 | MLS# 1004369 | Listing updated on 2026-09-18

Photo 1 of Single family home for sale at 24 Walnut St, Chester, NY 10918 | MLS# 1004369 | Listing updated on 2026-09-18

Photo 2 of Single family home for sale at 24 Walnut St, Chester, NY 10918 | MLS# 1004369 | Listing updated on 2026-09-18

$525,000

count-img 12

4Bds

3Ba

2,698sqft

Single family home for sale

24 Walnut St, Chester, NY 10918

Keller Williams Village Sq Rlt

Hot

Photo 3 of Single family home for sale at 16 Cambridge Cir, Monroe, NY 10950 | MLS# 1041577 | Listing updated on 2026-10-05

Photo 1 of Single family home for sale at 16 Cambridge Cir, Monroe, NY 10950 | MLS# 1041577 | Listing updated on 2026-10-05

Photo 2 of Single family home for sale at 16 Cambridge Cir, Monroe, NY 10950 | MLS# 1041577 | Listing updated on 2026-10-05

$525,000

count-img 12

4Bds

3Ba

2,216sqft

Single family home for sale

16 Cambridge Cir, Monroe, NY 10950

Kw Hudson Valley United

3D Tour

Photo 3 of Single family home for sale at 74 Heaton Rd, Chester Town, NY 10950 | MLS# 1037241 | Listing updated on 2026-09-24

Photo 1 of Single family home for sale at 74 Heaton Rd, Chester Town, NY 10950 | MLS# 1037241 | Listing updated on 2026-09-24

Photo 2 of Single family home for sale at 74 Heaton Rd, Chester Town, NY 10950 | MLS# 1037241 | Listing updated on 2026-09-24

$500,000

count-img 10

3Bds

2Ba

1,676sqft

Single family home for sale

74 Heaton Rd, Chester Town, NY 10950

Coldwell Banker Realty

Photo 3 of Land for sale at 30 Harding Way, Monroe, NY 10950 | MLS# 950482 | Listing updated on 2026-09-18

Photo 1 of Land for sale at 30 Harding Way, Monroe, NY 10950 | MLS# 950482 | Listing updated on 2026-09-18

Photo 2 of Land for sale at 30 Harding Way, Monroe, NY 10950 | MLS# 950482 | Listing updated on 2026-09-18

$500,000

count-img 10

--Bds

--Ba

9.78acres lot

Land for sale

30 Harding Way, Monroe, NY 10950

Keller Williams Realty

Photo 2 of Sale Pending at Main St, Chester, NY 10918 | MLS# H6204360 | Listing updated on 2026-09-18

Photo 1 of Sale Pending at Main St, Chester, NY 10918 | MLS# H6204360 | Listing updated on 2026-09-18

$500,000

count-img 3

--Bds

--Ba

36,098sqft lot

Sale Pending

Main St, Chester, NY 10918

Keller Williams Realty

Photo 3 of Sale Pending at 264 Bull Ml Rd, Chester Town, NY 10918 | MLS# 1049026 | Listing updated on 2026-10-07

Photo 1 of Sale Pending at 264 Bull Ml Rd, Chester Town, NY 10918 | MLS# 1049026 | Listing updated on 2026-10-07

Photo 2 of Sale Pending at 264 Bull Ml Rd, Chester Town, NY 10918 | MLS# 1049026 | Listing updated on 2026-10-07

$499,000

count-img 10

3Bds

3Ba

1,848sqft

Sale Pending

264 Bull Ml Rd, Chester Town, NY 10918

Keller Williams Realty

3D Tour

Photo 3 of Sale Pending at 8 Bridle Ln, Chester Town, NY 10918 | MLS# 1036394 | Listing updated on 2026-10-07

Photo 1 of Sale Pending at 8 Bridle Ln, Chester Town, NY 10918 | MLS# 1036394 | Listing updated on 2026-10-07

Photo 2 of Sale Pending at 8 Bridle Ln, Chester Town, NY 10918 | MLS# 1036394 | Listing updated on 2026-10-07

$495,000

count-img 3

4Bds

2Ba

1,820sqft

Sale Pending

8 Bridle Ln, Chester Town, NY 10918

Keller Williams Realty

Price Drop: $40K

Photo 3 of Single family home for sale at 94 Booth Rd, Chester Town, NY 10918 | MLS# 1050173 | Listing updated on 2026-10-06

Photo 1 of Single family home for sale at 94 Booth Rd, Chester Town, NY 10918 | MLS# 1050173 | Listing updated on 2026-10-06

Photo 2 of Single family home for sale at 94 Booth Rd, Chester Town, NY 10918 | MLS# 1050173 | Listing updated on 2026-10-06

$485,000

3Bds

3Ba

2,441sqft

Single family home for sale

94 Booth Rd, Chester Town, NY 10918

Howard Hanna Rand Realty

3D Tour

Photo 3 of Sale Pending at 21 Trotting Dr, Chester Town, NY 10918 | MLS# 1030740 | Listing updated on 2026-10-07

Photo 1 of Sale Pending at 21 Trotting Dr, Chester Town, NY 10918 | MLS# 1030740 | Listing updated on 2026-10-07

Photo 2 of Sale Pending at 21 Trotting Dr, Chester Town, NY 10918 | MLS# 1030740 | Listing updated on 2026-10-07

$475,000

count-img 8

3Bds

2Ba

1,624sqft

Sale Pending

21 Trotting Dr, Chester Town, NY 10918

Keller Williams Realty

Price Drop: $14K

Photo 3 of Sale Pending at 32 Surrey Rd, Chester Town, NY 10918 | MLS# 1040785 | Listing updated on 2026-09-24

Photo 1 of Sale Pending at 32 Surrey Rd, Chester Town, NY 10918 | MLS# 1040785 | Listing updated on 2026-09-24

Photo 2 of Sale Pending at 32 Surrey Rd, Chester Town, NY 10918 | MLS# 1040785 | Listing updated on 2026-09-24

$475,000

count-img 5

4Bds

2Ba

1,820sqft

Sale Pending

32 Surrey Rd, Chester Town, NY 10918

Exp Realty

Hot

3D Tour

Photo 3 of Single family home for sale at 8 Townsend Pl, Chester Town, NY 10918 | MLS# 1047996 | Listing updated on 2026-10-06

Photo 1 of Single family home for sale at 8 Townsend Pl, Chester Town, NY 10918 | MLS# 1047996 | Listing updated on 2026-10-06

Photo 2 of Single family home for sale at 8 Townsend Pl, Chester Town, NY 10918 | MLS# 1047996 | Listing updated on 2026-10-06

$459,000

count-img 14

4Bds

2Ba

1,832sqft

Single family home for sale

8 Townsend Pl, Chester Town, NY 10918

Howard Hanna Rand Realty

Photo 3 of Single family home for sale at 1367 Kings Hwy, Chester Town, NY 10918 | MLS# 1036770 | Listing updated on 2026-08-14

Photo 1 of Single family home for sale at 1367 Kings Hwy, Chester Town, NY 10918 | MLS# 1036770 | Listing updated on 2026-08-14

Photo 2 of Single family home for sale at 1367 Kings Hwy, Chester Town, NY 10918 | MLS# 1036770 | Listing updated on 2026-08-14

$440,000

3Bds

2Ba

1,728sqft

Single family home for sale

1367 Kings Hwy, Chester Town, NY 10918

Greene Realty Group

Photo 3 of Single family home for sale at 4 Maple Ln, Monroe, NY 10950 | MLS# 1008564 | Listing updated on 2026-09-20

Photo 1 of Single family home for sale at 4 Maple Ln, Monroe, NY 10950 | MLS# 1008564 | Listing updated on 2026-09-20

Photo 2 of Single family home for sale at 4 Maple Ln, Monroe, NY 10950 | MLS# 1008564 | Listing updated on 2026-09-20

$429,000

count-img 6

3Bds

2Ba

1,460sqft

Single family home for sale

4 Maple Ln, Monroe, NY 10950

Flag Realty Group

Photo 3 of Single family home for sale at 23 Pike Ct, Chester Town, NY 10950 | MLS# 1031523 | Listing updated on 2026-10-02

Photo 1 of Single family home for sale at 23 Pike Ct, Chester Town, NY 10950 | MLS# 1031523 | Listing updated on 2026-10-02

Photo 2 of Single family home for sale at 23 Pike Ct, Chester Town, NY 10950 | MLS# 1031523 | Listing updated on 2026-10-02

$425,000

count-img 8

3Bds

2Ba

2,460sqft

Single family home for sale

23 Pike Ct, Chester Town, NY 10950

Re/Max Benchmark Realty Group

Photo 3 of Single family home for sale at 70 Main St, Chester Town, NY 10918 | MLS# 1034449 | Listing updated on 2026-10-05

Photo 1 of Single family home for sale at 70 Main St, Chester Town, NY 10918 | MLS# 1034449 | Listing updated on 2026-10-05

Photo 2 of Single family home for sale at 70 Main St, Chester Town, NY 10918 | MLS# 1034449 | Listing updated on 2026-10-05

$425,000

count-img 2

3Bds

3Ba

1,357sqft

Single family home for sale

70 Main St, Chester Town, NY 10918

Curasi Realty, Inc.

Price Drop: $3K

3D Tour

Photo 3 of Single family home for sale at 21 Midway Dr, Chester Town, NY 10950 | MLS# 1044454 | Listing updated on 2026-10-03

Photo 1 of Single family home for sale at 21 Midway Dr, Chester Town, NY 10950 | MLS# 1044454 | Listing updated on 2026-10-03

Photo 2 of Single family home for sale at 21 Midway Dr, Chester Town, NY 10950 | MLS# 1044454 | Listing updated on 2026-10-03

$409,000

count-img 9

3Bds

1Ba

1,288sqft

Single family home for sale

21 Midway Dr, Chester Town, NY 10950

Howard Hanna Rand Realty

Photo 3 of Sale Pending at Four Corners Rd, Chester, NY 10918 | MLS# 995871 | Listing updated on 2026-09-10

Photo 1 of Sale Pending at Four Corners Rd, Chester, NY 10918 | MLS# 995871 | Listing updated on 2026-09-10

Photo 2 of Sale Pending at Four Corners Rd, Chester, NY 10918 | MLS# 995871 | Listing updated on 2026-09-10

$399,900

count-img 6

--Bds

--Ba

13.6acres lot

Sale Pending

Four Corners Rd, Chester, NY 10918

Raynor Country

Photo 3 of Land for sale at 492 Black Meadow Rd, Chester, NY 10918 | MLS# 1002697 | Listing updated on 2026-10-01

Photo 1 of Land for sale at 492 Black Meadow Rd, Chester, NY 10918 | MLS# 1002697 | Listing updated on 2026-10-01

Photo 2 of Land for sale at 492 Black Meadow Rd, Chester, NY 10918 | MLS# 1002697 | Listing updated on 2026-10-01

$399,000

count-img 6

--Bds

--Ba

46acres lot

Land for sale

492 Black Meadow Rd, Chester, NY 10918

Exp Realty

$389,900

count-img 9

3Bds

2Ba

1,393sqft

Sale Pending

4114 Whispering Hls

4114 Whispering Hills, Chester Town, NY 10918

Coldwell Banker Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 4114 Whispering Hls, Chester Town, NY 10918

4114 Whispering Hls

$389,900 - $389,900

4114 Whispering Hls, Chester Town, NY 10918

3 Beds

$389.9k+

$389,900

count-img 4

3Bds

3Ba

1,694sqft

Condo for sale

213 Eagleton Dr

213 Eagleton Dr, Chester Town, NY 10950

Keller Williams Valley Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 213 Eagleton Dr, Monroe, NY 10950

213 Eagleton Dr

$389,900 - $389,900

213 Eagleton Dr, Monroe, NY 10950

3 Beds

$389.9k+

Price Drop: $20K

Photo 3 of Sale Pending at 7 Hambletonian Ave, Chester, NY 10918 | MLS# 964090 | Listing updated on 2026-09-19

Photo 1 of Sale Pending at 7 Hambletonian Ave, Chester, NY 10918 | MLS# 964090 | Listing updated on 2026-09-19

Photo 2 of Sale Pending at 7 Hambletonian Ave, Chester, NY 10918 | MLS# 964090 | Listing updated on 2026-09-19

$379,900

count-img 5

2Bds

1Ba

1,026sqft

Sale Pending

7 Hambletonian Ave, Chester, NY 10918

Homesmart Homes & Estates

Photo 3 of Single family home for sale at 33 Meadow Ave, Chester Town, NY 10918 | MLS# 1033159 | Listing updated on 2026-09-30

Photo 1 of Single family home for sale at 33 Meadow Ave, Chester Town, NY 10918 | MLS# 1033159 | Listing updated on 2026-09-30

Photo 2 of Single family home for sale at 33 Meadow Ave, Chester Town, NY 10918 | MLS# 1033159 | Listing updated on 2026-09-30

$370,000

3Bds

1Ba

1,561sqft

Single family home for sale

33 Meadow Ave, Chester Town, NY 10918

River Realty Services, Inc.

3D Tour

$370,000

count-img 8

3Bds

2Ba

1,316sqft

Sale Pending

3211 Whispering Hls

3211 Whispering Hills, Chester Town, NY 10918

Re/Max Benchmark Realty Group

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 3211 Whispering Hls, Chester Town, NY 10918

3211 Whispering Hls

$370,000 - $370,000

3211 Whispering Hls, Chester Town, NY 10918

3 Beds

$370k+

$370,000

count-img 8

3Bds

3Ba

1,331sqft

Condo for sale

4704 Whispering Hls

4704 Whispering Hills, Chester Town, NY 10918

Sahagian Realty Llc

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 4704 Whispering Hls, Chester Town, NY 10918

4704 Whispering Hls

$370,000 - $370,000

4704 Whispering Hls, Chester Town, NY 10918

3 Beds

$370k+

$360,000

count-img 8

3Bds

3Ba

1,585sqft

Sale Pending

154 Eagleton Dr

154 Eagleton Dr, Monroe, NY 10950

Keller Williams Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 154 Eagleton Dr, Monroe, NY 10950

154 Eagleton Dr

$360,000 - $360,000

154 Eagleton Dr, Monroe, NY 10950

3 Beds

$360k+

$360,000

count-img 4

3Bds

3Ba

1,331sqft

Sale Pending

3409 Whispering Hls

3409 Whispering Hills, Chester Town, NY 10918

Howard Hanna Rand Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 3409 Whispering Hls, Chester Town, NY 10918

3409 Whispering Hls

$360,000 - $360,000

3409 Whispering Hls, Chester Town, NY 10918

3 Beds

$360k+

$359,000

count-img 13

3Bds

3Ba

1,331sqft

Condo for sale

2522 Whispering Hls

2522 Whispering Hills, Chester Town, NY 10918

Howard Hanna Rand Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 2522 Whispering Hls, Chester Town, NY 10918

2522 Whispering Hls

$359,000 - $359,000

2522 Whispering Hls, Chester Town, NY 10918

3 Beds

$359k+

3D Tour

$355,000

count-img 5

3Bds

3Ba

1,585sqft

Sale Pending

255 Heritage Ln

255 Heritage Ln, Chester Town, NY 10950

Coldwell Banker Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 255 Heritage Ln, Chester Town, NY 10950

255 Heritage Ln

$355,000 - $355,000

255 Heritage Ln, Chester Town, NY 10950

3 Beds

$355k+

Hot

3D Tour

Photo 3 of Single family home for sale at 241 Meadow Ave, Chester, NY 10918 | MLS# 1024779 | Listing updated on 2026-09-19

Photo 1 of Single family home for sale at 241 Meadow Ave, Chester, NY 10918 | MLS# 1024779 | Listing updated on 2026-09-19

Photo 2 of Single family home for sale at 241 Meadow Ave, Chester, NY 10918 | MLS# 1024779 | Listing updated on 2026-09-19

$349,999

count-img 12

4Bds

2Ba

1,560sqft

Single family home for sale

241 Meadow Ave, Chester, NY 10918

Keller Williams Realty

$349,999

count-img 6

3Bds

2Ba

1,316sqft

Sale Pending

3414 Whispering Hls

3414 Whispering Hills, Chester, NY 10918

Kw Hudson Valley United

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 3414 Whispering Hls, Chester, NY 10918 - Unit #

Unit #

3414 Whispering Hls

$349,999 - $349,999

3414 Whispering Hls, Chester, NY 10918

3 Beds

$350k+

$339,900

count-img 2

2Bds

2Ba

1,086sqft

Condo for sale

3706 Whispering Hls

3706 Whispering Hills, Chester Town, NY 10918

Exp Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 3706 Whispering Hls, Chester Town, NY 10918

3706 Whispering Hls

$339,900 - $339,900

3706 Whispering Hls, Chester Town, NY 10918

2 Beds

$339.9k+

$329,900

count-img 6

3Bds

2Ba

1,316sqft

Sale Pending

1311 Whispering Hls

1311 Whispering Hills, Chester, NY 10918

Keller Williams Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 1311 Whispering Hls, Chester, NY 10918 - Unit #

Unit #

1311 Whispering Hls

$329,900 - $329,900

1311 Whispering Hls, Chester, NY 10918

3 Beds

$329.9k+

$329,000

count-img 5

2Bds

2Ba

1,294sqft

Sale Pending

4118 Whispering Hls Dr

4118 Whispering Hills Dr, Goshen, NY 10918

Howard Hanna Rand Realty

Building 1 Unit Available

Listing Photo 3 - Condo for sale in building located at 4118 Whispering Hls Dr, Goshen, NY 10918 - Unit #

Unit #

4118 Whispering Hls Dr

$329,000 - $329,000

4118 Whispering Hls Dr, Goshen, NY 10918

2 Beds

$329k+

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30,416

$870,000

Homes for Sale York

22,787

$243,500

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13,780

$1,325,000

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4,622

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3,007

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1,534

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1,231

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782

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598

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337

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317

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270

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202

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201

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177

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173

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172

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163

$177,500

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122

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119

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Based on information from OneKey MLS, through Oct 8, 2026, 11:01 AM. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 OneKey® MLS. All rights reserved.

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