Sherman Homes under $500,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Sherman 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 Sherman Homes under $500,000

$399,000

2 Beds ⋅ 1 Baths ⋅ 24202184 MLS

Welcome home to this charming 2-bedroom, 1-bath Cape Cod overflowing with character in the desirable Candlewood Echoes community of Sherman, CT. Nestled along the tranquil northern shores of Squantz Pond near New Fairfield, this private beach neighborhood offers an idyllic lifestyle with direct beach access for year-round swimming, kayaking, paddleboarding, fishing, and winter ice sports. Inside, a generous wide-open floor plan seamlessly connects the living and family room spaces to a dining area with custom built-ins and a corner curio and space for an in-home office. The spacious eat-in kitchen features ample cabinetry, a pantry, and rustic vaulted wood ceilings, stepping out to a covered small side porch that leads to a sprawling backyard with a firepit. The main level boasts a serene primary bedroom and an updated full bath with a glass-enclosed brick-tiled shower, wainscoting, and newer fixtures. The upper-level loft bedroom offers built-in drawers and under-eaves storage. Downstairs, the unfinished walk-out lower level includes laundry and abundant storage with direct access to the back lawn. Complete with parking just steps up from the front door, major updates including a brand-new well pump, new hot water heater, and newer asphalt roof, plus low HOA fees and low taxes, this Cape home is just 60 minutes from Manhattan with easy highway and Metro-North access. Efficient oil heat, gravel driveway parking, super value with large open floor plan, just minutes to beach!

150 Rte 39 S, Sherman

$440,000

3 Beds ⋅ 1 Baths ⋅ 24197820 MLS

Are LOW TAXES and privacy your priority? Buyers, this is a great opportunity to bring your vision and create your perfect home! Set back from the road and situated on a little over 3 acres of park-like property, this home offers open space, a deck for entertaining, and exceptional privacy. With Deer Pond Farm Sanctuary bordering the back of the property, no one can build behind you. Inside, you'll find an easy one-level layout with no stairs, cathedral ceilings, and plenty of natural light throughout the open-concept kitchen and living room. The pellet stove keeps the home warm and cozy all winter long. A newer roof means you can focus your attention on updating the interior to match your style and preferences. Enjoy lake life all summer at Sherman Town Beach, available exclusively to residents. Conveniently located for commuting to New York and just a short drive to the charming downtowns of Kent and New Milford. Don't miss this opportunity, schedule your showing today!

33 Rte 55 W, Sherman

$429,900

3 Beds ⋅ 1 Baths ⋅ 24197493 MLS

Welcome to your private retreat nestled on a scenic wooded lot with distant views of Green Pond. Located in a quiet gated community, this charming 3-bedroom, 1-bath ranch offers a peaceful layout designed for relaxed living and effortless indoor-outdoor connection. Step inside to discover a bright, expansive sunroom wrapped in wall-to-wall windows that fill the home with natural light and frame beautiful views of the surrounding trees. Off the back, two spacious decks provide the perfect setting for morning coffee, evening relaxing, or outdoor entertaining. The primary level offers single-story convenience, while the walk-out basement presents fantastic potential to be finished into extra living space, a media room, or a home gym. Enjoy access to Green Pond, a pristine 30-acre private lake where you can spend your weekends kayaking, paddleboarding, and swimming in total tranquility-no motorboats allowed. Combining privacy, natural beauty, and lakeside amenities, this property is a rare find ready for your personal touch.

8 Terrace Dr, Sherman

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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.