Homes for Sale Under 800K in Chester, CT

10 Homes for Sale

Sort by:Newest Listings

Open House

Photo 3 of Single family home for sale at 13 High Fld Ln, Chester, CT 06412 | MLS# 24198973 | Listing updated on 2026-10-15

Photo 1 of Single family home for sale at 13 High Fld Ln, Chester, CT 06412 | MLS# 24198973 | Listing updated on 2026-10-15

Photo 2 of Single family home for sale at 13 High Fld Ln, Chester, CT 06412 | MLS# 24198973 | Listing updated on 2026-10-15

$764,900

count-img 2

4Bds

3Ba

2,662sqft

Single family home for sale

13 High Fld Ln, Chester, CT 06412

William Pitt Sotheby'S Int'L

Photo 3 of Single family home for sale at 275 W Main St, Chester, CT 06412 | MLS# 24213774 | Listing updated on 2026-10-12

Photo 1 of Single family home for sale at 275 W Main St, Chester, CT 06412 | MLS# 24213774 | Listing updated on 2026-10-12

Photo 2 of Single family home for sale at 275 W Main St, Chester, CT 06412 | MLS# 24213774 | Listing updated on 2026-10-12

$715,000

4Bds

4Ba

2,706sqft

Single family home for sale

275 W Main St, Chester, CT 06412

Coldwell Banker Realty

Photo 3 of Single family home for sale at 42 Straits Rd, Chester, CT 06412 | MLS# 24212291 | Listing updated on 2026-10-09

Photo 1 of Single family home for sale at 42 Straits Rd, Chester, CT 06412 | MLS# 24212291 | Listing updated on 2026-10-09

Photo 2 of Single family home for sale at 42 Straits Rd, Chester, CT 06412 | MLS# 24212291 | Listing updated on 2026-10-09

$699,000

count-img 2

3Bds

3Ba

2,882sqft

Single family home for sale

42 Straits Rd, Chester, CT 06412

Great Estates, Ct

Photo 3 of Multi family home for sale at 84 86 Spring St, Chester, CT 06412 | MLS# 24207359 | Listing updated on 2026-09-20

Photo 1 of Multi family home for sale at 84 86 Spring St, Chester, CT 06412 | MLS# 24207359 | Listing updated on 2026-09-20

Photo 2 of Multi family home for sale at 84 86 Spring St, Chester, CT 06412 | MLS# 24207359 | Listing updated on 2026-09-20

$579,900

count-img 4

4Bds

3Ba

3,506sqft

Multi family home for sale

84 86 Spring St, Chester, CT 06412

Carbutti & Co., Realtors

Photo 3 of Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24

Photo 1 of Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24

Photo 2 of Single family home for sale at 28 Deep Holw Rd, Chester, CT 06412 | MLS# 24199280 | Listing updated on 2026-09-24

$559,000

count-img 2

3Bds

3Ba

1,740sqft

Single family home for sale

28 Deep Holw Rd, Chester, CT 06412

Property Shoppe, Llc

Photo 3 of Single family home for sale at 55 Wig Hill Rd, Chester, CT 06412 | MLS# 24202647 | Listing updated on 2026-09-27

Photo 1 of Single family home for sale at 55 Wig Hill Rd, Chester, CT 06412 | MLS# 24202647 | Listing updated on 2026-09-27

Photo 2 of Single family home for sale at 55 Wig Hill Rd, Chester, CT 06412 | MLS# 24202647 | Listing updated on 2026-09-27

$499,900

count-img 7

3Bds

2Ba

1,774sqft

Single family home for sale

55 Wig Hill Rd, Chester, CT 06412

Puorro Realty Group

Photo 3 of Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21

Photo 1 of Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21

Photo 2 of Single family home for sale at 88 Winthrop Rd, Chester, CT 06412 | MLS# 24204497 | Listing updated on 2026-09-21

$499,000

count-img 9

3Bds

3Ba

2,240sqft

Single family home for sale

88 Winthrop Rd, Chester, CT 06412

Re/Max Heritage

Price Drop: $16K

Photo 3 of Single family home for sale at 6 Castle View Dr, Chester, CT 06412 | MLS# 24102694 | Listing updated on 2026-10-06

Photo 1 of Single family home for sale at 6 Castle View Dr, Chester, CT 06412 | MLS# 24102694 | Listing updated on 2026-10-06

Photo 2 of Single family home for sale at 6 Castle View Dr, Chester, CT 06412 | MLS# 24102694 | Listing updated on 2026-10-06

$449,000

count-img 3

3Bds

2Ba

2,031sqft

Single family home for sale

6 Castle View Dr, Chester, CT 06412

William Raveis Real Estate

Photo 3 of Single family home for sale at 43 Goose Hl Rd, Chester, CT 06412 | MLS# 24205998 | Listing updated on 2026-09-20

Photo 1 of Single family home for sale at 43 Goose Hl Rd, Chester, CT 06412 | MLS# 24205998 | Listing updated on 2026-09-20

Photo 2 of Single family home for sale at 43 Goose Hl Rd, Chester, CT 06412 | MLS# 24205998 | Listing updated on 2026-09-20

$439,900

3Bds

2Ba

1,742sqft

Single family home for sale

43 Goose Hl Rd, Chester, CT 06412

Cavanaugh & Company Llc

Photo 3 of Single family home for sale at 40 Castle View Dr, Chester, CT 06412 | MLS# 24210808 | Listing updated on 2026-10-16

Photo 1 of Single family home for sale at 40 Castle View Dr, Chester, CT 06412 | MLS# 24210808 | Listing updated on 2026-10-16

Photo 2 of Single family home for sale at 40 Castle View Dr, Chester, CT 06412 | MLS# 24210808 | Listing updated on 2026-10-16

$379,900

3Bds

2Ba

1,142sqft

Single family home for sale

40 Castle View Dr, Chester, CT 06412

Re/Max Valley Shore

Don't miss out on new listings — and get instant email alerts!

Do Real Estate on the Go!

Find your dream home, receive real-time updates, and many more!

OPEN APP

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Download App

No. of Homes

Prices

Homes for Sale New Haven

1,731

$3,500

Homes for Sale Hartford

1,286

$242,500

Homes for Sale Stamford

240

$337,000

Homes for Sale Waterbury

233

$220,000

Homes for Sale Norwalk

142

$360,000

Homes for Sale Greenwich

$515,000

Homes for Sale Newtown

$625,000

Homes for Sale Cheshire Town

$590,000

Homes for Sale Glastonbury Center

$600,000

Houses for Sale in Chester Under $100K

Houses for Sale in Chester Under $150K

Houses for Sale in Chester Under $200K

Houses for Sale in Chester Under $250K

Houses for Sale in Chester Under $300K

Houses for Sale in Chester Under $350K

Houses for Sale in Chester Under $400K

Houses for Sale in Chester Under $450K

Houses for Sale in Chester Under $500K

Houses for Sale in Chester Under $600K

Houses for Sale in Chester Under $700K

Houses for Sale in Chester Under $800K

Mortgage Calculator

How Much House Can I Afford

How to Buy a House

Best Places to Live in Connecticut

Safest Places to Live in Connecticut

Cheapest Places to Live in Connecticut

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 17, 2026, 9:30 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.