Sterling Real Estate

Welcome to Sterling, Connecticut, a hidden gem nestled in the picturesque Windham County. This charming town is known for its serene landscapes, rich history, and a strong sense of community, making it an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

Sterling boasts a blend of rural charm and modern conveniences. With its rolling hills, lush forests, and tranquil lakes, outdoor enthusiasts will find plenty to explore. Enjoy hiking, fishing, and picnicking in the beautiful surroundings or take a leisurely stroll through the quaint neighborhoods. The town is also home to several parks and recreational facilities, ensuring that residents have ample opportunities to stay active and engaged.

The sense of community in Sterling is palpable, with numerous local events and gatherings throughout the year. From farmers' markets to seasonal festivals, there’s always something happening that brings neighbors together. The town’s commitment to preserving its history is evident in its well-maintained historic buildings and sites, offering a glimpse into the past while fostering a sense of pride among residents.

Education is a priority in Sterling, with access to quality schools that cater to the needs of children and families. The town’s close-knit atmosphere makes it easy for newcomers to feel at home, and the friendly faces you encounter will make you feel like a part of the community in no time.

Whether you’re looking to settle down or invest in a property, Sterling, CT, offers a unique blend of tranquility and charm that is hard to resist. Come discover your new home in this idyllic town!

Newest Listings in Sterling

$249,900

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194085 MLS ⋅ River Bend BLDG.

Enjoy affordable, low-maintenance waterfront living in this charming 8-unit condominium community! Tucked away at the back of the complex, this 2-bedroom, 1.5-bath condo offers privacy and beautiful views where the river widens into a peaceful, pond-like setting. Conveniently located just 5 miles from I-395 and only 1.5 miles from the Rhode Island border. Step outside and enjoy waterfront living less than 20 steps from your door. Spend your days fishing, kayaking, relaxing by the water, or dining on your private deck while taking in the scenic river and pond views. Inside, you'll find an in-unit laundry room, an attached one-car garage, and a bright kitchen that opens to the deck overlooking the yard and water beyond. The HVAC system is less than three years old and includes approximately seven years remaining on its warranty. The association allows up to two dogs or two cats, making this an ideal home for pet lovers looking for an easy-care home in a peaceful waterfront setting. This condo offers comfort, convenience, and a lifestyle you'll love.

34 Pond St Unit 7, Sterling

$325,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193037 MLS

Attention investors, contractors, and handy buyers! This 4-bedroom, 2 full bathroom cape presents an outstanding opportunity to build equity and transform a property with incredible potential. While the home is in need of a full renovation, several major features are already in place, including a brand-new roof and solar system to help offset future energy costs. Inside, you'll find a spacious layout ready for your vision and creativity. Whether you're looking to renovate and resell, create a rental property, or customize a home for yourself, this property offers a solid foundation for your next project. Step outside and you'll discover one of the property's standout features-a generous yard with park-like potential. With the right landscaping and improvements, this outdoor space could become a true retreat for entertaining, recreation, or relaxation. Opportunities like this don't come around often. Bring your tools, ideas, and imagination to unlock the full potential of this property. Sold as-is.

50 Pine Hill Rd, Sterling

$470,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190726 MLS

Built in 1825 in the Quaint town of Oneco this Adorable 3 Family on Oneco Pond is a great Waterfront Property!!! In the Summertime enjoy Kayaking, Canoeing, Swimming, Fishing or just sit and enjoy the Beautiful Views of the Pond from the deck or back yard. In the Winter enjoy Ice Skating or Ice Fishing. Home has 3 units. Two units have 2 Bedrooms and 1 Full Bath and 1 unit has 1 Bedroom and 1 Full Bath. Oil Heat for two units with two separate furnaces which are only about 6 years old and the upstairs unit has electric heat. Shared drilled well and newer shared septic. Many recent updates to the property include most windows and some flooring. One of the first-floor units has beautiful hardwood flooring and a stone Fireplace! All 3 Units are Rented at this time. Close to RI line! Only 30 minutes to Mass Line And approximately 30 minutes to casinos!

Plainfield Pike, Sterling

$550,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190128 MLS

STUNNING 2023 COLONIAL right on the RI LINE w/ 4 SPACIOUS bedrooms w/ HARDWOOD flooring and the primary has a walk in closet and primary bathroom w/ DEEP tub & Tile surround 72 inch DOUBLE vanity. GORGEOUS HARDWOOD flooring throughout, HARDWOOD STAIRS and RECESS lighting. FORCED HOT AIR/CENTRAL AIR and open floor plan on 1st floor with living room, formal dining room and BEAUTIFUL kitchen w/ STAINLESS APPLIANCES (refrigerator & dishwasher are BRAND NEW) and GRANITE COUNTERS w/ UPGRADED 7 foot ISLAND and double oven. OVERSIZED 24 x 24 2 car garage w/ insulated walls & ceiling, electrical outlets-20 amp w/ extra lights. PAVED driveway and CONCRETE walkway leads to front porch. HUGE level yard with 1.31 ACRES and LARGE deck, WALKOUT basement could easily be finished for more sq ft. 4 miles to 395 for easy commute. Sellers paid $29,000 in UPGRADES ATTACHED on top of $499,900!! 4 bedroom plans attached & CAMERAS! Do not go on property without appointment THANKYOU

456 Sterling Hill Rd, Sterling

$79,900

ACTIVE Status ⋅ 24161415 MLS

Land was approved for a 3 bedroom home in 2004 - please do your due diligence with the town. Beautiful country lot that is high and dry to build your dream home. 4.5 Miles to 395 and close to RI line. 617Ft of road frontage.

18 Ledge Hill Rd, Sterling

$35,000

ACTIVE Status ⋅ 24159941 MLS

Tucked away for privacy yet conveniently located near the Rhode Island line. Enjoy the peace and charm of a scenic, rural setting while still being within reach of nearby amenities. This lot of record provides a rare opportunity to find property in this price range. Whether you're looking to create a private retreat or a year-round residence, this property is full of potential.

627-B Bailey Rd, Sterling

$400,000

ACTIVE Status ⋅ 24143165 MLS

11.80 of sand, gravel and rock. Current owner has permits in place. 1300 ft of road frontage. Lots of possibilities. Seller will be removing large boulders.

131 Church St, Sterling

$299,900

ACTIVE Status ⋅ 24142256 MLS

Discover the potential of this 1.07 acre lot. The property currently features a barn structure, but the true value lies in the land itself, being located on a private - no outlet road! With ample space to develop to dream property. Explore the possibilities this well-situated property has to offer. Trailer on property does not convey.

71 Deerfield Dr, Sterling

$60,000

ACTIVE Status ⋅ 24142268 MLS

Discover this beautiful 0.61-acre lot-ready and waiting for your dream build. Tucked away on a private road in Sterling, CT, this property offers the perfect opportunity to create your own peaceful retreat. Whether you're envisioning a custom home or a quiet getaway, this slice of heaven provides the privacy and space you've been looking for.

81 Deerfield Dr, Sterling

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.