Chester Homes under $750,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Chester and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Chester Homes under $750,000

$749,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217528 MLS

Privacy, space, and location combine with this custom colonial on over two private acres at the end of a quiet cul-de-sac. This 2,662-square-foot home offers a rare opportunity to enjoy the tranquility of a tucked-away setting without sacrificing proximity to downtown Chester. An inviting covered front porch welcomes you to sit and enjoy the peace of this quiet neighborhood. Once inside, the entryway is bordered by a living room and a formal dining room with a bay window. There is also a spacious family room with a propane fireplace, and a sunny kitchen with a center island and ample cabinet space, an eat-in kitchen, and pantry. The kitchen leads to a large deck overlooking the backyard, perfect for dining, entertaining, or simply enjoying the natural beauty of the property. The second story offers four bedrooms, including the primary suite with a generous walk-in closet and ensuite bathroom that features both a soaking tub and shower. Two sizable bedrooms and a guest bedroom share a full bath. There is a bonus room over the two-car garage that could serve as a den, office, or playroom and a full unfinished basement. Ideally situated near Chester's acclaimed restaurants, shops, galleries, and village amenities, this property offers the best of both worlds: a private retreat with the character and convenience of downtown Chester just moments away. A special opportunity to make this well-established property your own.

13 High Field Ln, Chester

$450,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24216914 MLS

Just a quick stroll from the heart of Chester Village, this absolutely charming three-bedroom, one-bath home offers a wonderful combination of classic character, recent improvements, and an exceptional location. From the moment you arrive, the inviting enclosed front porch welcomes you, providing additional living space and a wonderful spot to relax. Inside, the home retains much of its original charm, with beautiful hardwood floors, rich wood moldings throughout, and a lovely built-in corner hutch in the dining room. The kitchen has been updated from its original design, offering modern convenience while complementing the home's character. Recent improvements in 2026 include a freshly painted interior, refinished hardwood floors, and a professionally waterproofed basement. A walk-up attic offers potential for future expansion or additional storage. Situated on just under half an acre and only 0.2 miles from downtown, you'll enjoy easy access to Chester's wonderful restaurants, art galleries, boutiques, theater, and summer farmers market. With its timeless architectural details, thoughtful updates, and proximity to one of Connecticut's most vibrant villages, this home presents a wonderful opportunity to enjoy all that Chester has to offer. A must-see!

6 School Ln, Chester

$525,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24215476 MLS

Welcome home to this meticulously maintained Cape Cod-style residence, nestled on a tranquil cul-de-sac just steps from vibrant Chester Village. Cherished by the same owner for over 34 years, this home radiates pride of ownership, classic charm and everyday functionality. The main level features gleaming hardwood floors and a beautifully updated kitchen; complete with granite countertops, newer stainless steel appliances, a breakfast bar, and French doors providing access to the deck and private backyard. The seamless flow leads into a light-filled living room anchored by a cozy pellet stove, a formal dining room, and a generous laundry/pantry room with custom built-ins. A main-floor bedroom and full bath offer flexible options for guests, main-level living, or a dedicated home office. Upstairs, find two spacious bedrooms, including a primary suite with its own private bath. The second bedroom boasts a walk-in closet plus a separate oversized dressing/flex room. The lower level features a second pellet stove, offering endless potential for additional living space. Step outside to enjoy your backyard oasis featuring a custom-built, oversized fireplace ~ the ideal setting to unwind and entertain. Schedule your private showing today to experience the perfect blend of comfort, character; and village convenience! Please note: Professional Photos to follow.

6 Gilbert Hill Rd, Chester

$289,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24214929 MLS

Recently remodeled retreat nestled along the Pattaconck Brook, just seconds from the heart of Chester and conveniently located near Route 9. This 2 bedroom 1 bathroom home set on 2 acres offers a peaceful setting with the charm of nature. Extensive updates completed, including new siding, roofing, electrical, sheetrock, flooring, and a fully remodeled kitchen in 2021. A spacious living room and dining area with a wood stove for an alternative heat source. Additional improvements include a well pump, on-demand hot water and furnace heat exchanger. An impressive 45' x 28' garage with a walk-up loft offering another place to escape and unwind. Take advantage of this one of a kind opportunity! This is a manufactured home with additions and will not qualify for financing. CASH ONLY. Book your showing today!

173 W Main St, Chester

$715,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24213774 MLS

Discover move-in-ready living in desirable Chester, one of the Connecticut River Valley's most charming towns! Set on two picturesque acres across from Cockaponset State Forest, this beautifully renovated 4-bedroom, 3.5-bath home blends classic New England character with modern comfort, approximately three miles from Chester Village and Cedar Lake. Inside, refinished hardwood floors, multiple fireplaces, and inviting living spaces create a warm welcome, all updated & freshly painted. The stunning new kitchen features, beautiful cabinets, quartz countertops and premium THOR Gordon Ramsay Collection appliances. A first-floor bedroom & full bath offer flexibility for guests or main-level living. Upstairs, the primary suite boasts a fireplace, 6-foot walk-in closet, a spa-inspired bath with a rain shower and soaking tub! Two more bedrooms & yet another newly remodeled full bathroom complete this level. Approximately 800 square feet of permitted finished lower-level space, complete with a fireplace and bathroom adds room to relax, work, or entertain. Major improvements include a NEW SEPTIC SYSTEM, new plumbing, updated electrical with 200-amp service, new windows, siding, and gutters, plus three-zone central heating and air conditioning. Outside, enjoy a new 12' x 12' wood deck, landscaped grounds, and a private pond along the scenic rear approach. Two access points add convenience to this peaceful setting. Beautifully updated & ready to enjoy at an amazing price. Welcome home!

275 W Main St, Chester

$379,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24210808 MLS

One floor living in a quiet neighborhood just outside Chester Village. The main floor has a large Living Room, Kitchen and Dining Room, 3 bedrooms, 1 bathroom. The partially finished basement has 2 addional rooms, and storage. Some unfinished projects! Ready for your updating!

40 Castle View Dr, Chester

$699,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24212291 MLS

Welcome home this beautifully redesigned house set on over 2.5 acres in picturesque Chester, a quintessential New England town celebrated for its art, history, music, theater and exceptional dining. Completely renovated for today's lifestyle while retaining its warmth and character, this three-bedroom, 2.5-bath home offers beautifully refinished hardwood floors, 9-foot ceilings and thoughtfully designed living spaces throughout. The main level is ideal for entertaining, featuring an inviting living room with fireplace and sliders opening to a balcony/deck overlooking the property. The stunning new kitchen features quartz countertops, new cabinetry, a center island, new appliances, wine cooler and a charming dining nook. A spacious 17' x 13 room provides wonderful flexibility as a home office, or guest room. An updated half bath completes the main level. Upstairs, the primary suite offers a beautifully remodeled luxury bath and walk-in closet. Two additional bedrooms and a remodeled full bath complete the second floor. The finished lower level adds even more living space with an 11' x 21' family room, interior and direct garage access. The auxiliary generator has you covered for New England winters. Move-in ready and beautifully updated inside and out, this special property combines privacy, space and modern comfort with the charm of one of Connecticut's most desirable small towns. The home you've been waiting for-just in time for the holidays!

42 Straits Rd, Chester

$579,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24207359 MLS

Rare opportunity to own a hard to find multifamily in the beautiful town of Chester! This unique 2 unit property offers space, character and flexibility in a wonderful location, just a short drive to Cedar Lake and approximately a 15 minute walk to charming downtown Chester with its shops, restaurants and small town New England appeal. Unit 1 spans 3 levels and features 3 bedrooms, with 2 upstairs and 1 on the main level, 1.5 baths, hardwood floors, exposed beams in the living room and mini splits for heat and A/C. The half bath is ready to be completed, with the seller leaving the toilet, vanity and lighting for the next owner. Some windows have been replaced and the porch features new decking. Unit 2 offers 1 bedroom, 1 full bath, propane heat and a spacious living room with high ceilings. The bathroom features a new vanity and walk in shower. Each unit enjoys its own separate yard space. Major improvements include a new roof, new septic system and new insulation. The property also has a tankless hot water heater and separate electrical meters. Generator stays! A very large basement provides excellent storage and includes an area a previous owner began framing, along with multiple additional storage spaces. A rare opportunity for an investor or owner occupant looking to enjoy all that Chester has to offer!

84-86 Spring St, Chester

$252,500

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24198196 MLS

Charming 1927 Colonial offering a rare chance to own directly on the water in the heart of Chester. This 3-bedroom, 1-bath home spans 1,217 sq ft across two stories, with a classic layout featuring a living room and dining room on the main level and three bedrooms upstairs. Set on a 0.27-acre lot with vinyl siding and a paved driveway, the home sits right on the water with tranquil river views - a fantastic canvas for a riverfront retreat, whether you're an investor or a homeowner seeking direct water access. Just a short stroll to downtown Chester's boutiques, art galleries, and acclaimed dining. This property can also be purchased together with the adjacent 90 Water St for a larger waterfront compound (the two share an existing septic system). Bring your vision - this rare Chester waterfront offering won't last long! One of the parties to the LLC has an active real estate license

92 Water St, Chester

$237,500

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24198111 MLS

Rare opportunity to own directly on the water in the heart of Chester. This 1950-built ranch offers 1,034 sq ft with a flexible layout - currently set up as a 1-bedroom, the spacious family room (10'3" x 20'10") could easily convert to a second bedroom or home office. The oversized living room (13'6" x 20'10") anchors the home, while the combined kitchen/dining area (10'5" x 16'2") and comfortable primary bedroom round out the interior. Step outside to direct river frontage with sweeping water views and endless potential for outdoor living on the riverbank. All of this just a short stroll from downtown Chester's boutiques, galleries, and acclaimed restaurants. This property can also be purchased together with the adjacent 92 Water St for a larger waterfront compound (the two share an existing septic system). A fantastic value-add opportunity for an investor or a buyer with vision - bring your contractor and imagination! One of the parties to the LLC has an active real estate license.

90 Water St, Chester

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Chester Homes under $750,000

Newest Chester Homes under $750,000

How much is your home worth?

How much is your home worth?