Simsbury Homes under $500,000

Welcome to Simsbury, Connecticut—a picturesque town nestled in the heart of Hartford County, where charming New England landscapes meet a vibrant community spirit. Known for its rich history, Simsbury boasts a delightful blend of quaint colonial architecture and modern amenities, making it an ideal place for families, professionals, and retirees alike. With its scenic views of the Farmington River and the majestic Talcott Mountain, outdoor enthusiasts will find endless opportunities for hiking, biking, and enjoying nature.

Simsbury is not just about its stunning surroundings; it also offers a robust local economy, top-rated schools, and a variety of recreational activities. The town hosts numerous events throughout the year, fostering a strong sense of community and connection among residents. From farmers' markets to seasonal festivals, there's always something happening in this lively town.

For those looking to plant roots in Simsbury, you'll be pleased to find a selection of beautiful homes available for under $500,000. Whether you're seeking a cozy single-family residence, a charming historic home, or a modern townhouse, Simsbury offers a diverse range of properties that cater to various lifestyles and budgets. With its affordable housing options, you can enjoy the tranquility of suburban living while remaining close to the vibrant culture of Hartford and the surrounding areas.

Discover the beauty and charm of Simsbury today, and explore the wonderful homes waiting for you in this enchanting town! Your dream home in this idyllic community is just a visit away.

Newest Simsbury Homes under $500,000

$299,000

2 Beds ⋅ 3 Baths ⋅ 24211013 MLS ⋅ Talcott Acres BLDG.

Private and secluded, this 2-bedroom, 2.5-bath townhouse offers incredible potential in a peaceful setting. Featuring a one-car garage and a full basement, this home is ready for your personal updates and finishing touches to truly make it shine. The open living and dining area is perfect for entertaining, with sliding glass doors leading to a private deck. Both spacious bedrooms feature their own en-suite bathrooms, while the second bedroom also offers direct access to a charming private balcony. Additional highlights include natural gas heat, central air conditioning, and a desirable layout that provides both comfort and privacy. A wonderful opportunity to create your dream home in a tranquil location!

126 Hopmeadow St Unit 8E, Simsbury

Listing courtesy of Sabrina Janco from Century 21 Bay-Mar Realty. (860) 689-2691 (860) 582-7404

$474,900

3 Beds ⋅ 2 Baths ⋅ 24210037 MLS

Beautiful 3/4-bedroom, 2-bath Cape Cod situated on a corner lot with nearly 2 acres of gorgeous, usable land in the sought-after Latimer Lane School District. Step inside to gleaming hardwood floors and a wood-burning fireplace in the formal living room, which flows seamlessly into the eat-in kitchen featuring granite countertops, newer backsplash, newer stainless-steel appliances, pantry, and spacious dining area. Just off the kitchen is a wonderful family room with new carpet and built-in bookshelves, along with a convenient main-level bedroom and full bath. Upstairs, two spacious bedrooms with hardwood floors share a beautifully remodeled full bath. The dry lower level offers flexible space for a home office, gym, hobbies, or additional storage. Recent updates include a brand-new second-floor bathroom, new windows, new carpet, new pressure tank, and updated electrical panel. Enjoy plenty of room for entertaining, gardening, outdoor activities, and even a pool. Don't miss this wonderful opportunity to enjoy the space, privacy, and charm of nearly 2 acres in desirable Simsbury!

21 Ichabod Rd, Simsbury

Listing courtesy of Lauren Rownin from Berkshire Hathaway NE Prop.. (917) 921-3708 (860) 658-1981

$475,000

3 Beds ⋅ 2 Baths ⋅ 24208846 MLS

Brand new roof, exterior paint and interior flooring! Welcome to this spacious 3-bedroom, 2-bathroom contemporary home offering 2,444 square feet of bright, flexible living space nestled on a peaceful cul-de-sac. Enjoy all the privacy, yard space, and independence of single-family living paired with an unbeatable low $250/month HOA. At the heart of the home is the beautiful eat-in kitchen with additional dining space that offers exceptional room for cooking and gathering. The home features a gracious living room with gas fireplace and a spectacular great room with vaulted ceilings that create a dramatic yet comfortable gathering space. Designed for living and entertaining the indoor/outdoor flows seamlessly with expansive glass doors and decking. The 1997 addition created an expansive primary bedroom on the second floor with impressive space. All of this and it's just steps to the bike path and walkable to the charming center of Simsbury.

6 Tamarack Ln Unit 6, Simsbury

Listing courtesy of Sara Allan from Coldwell Banker Realty. (860) 674-0300 (860) 674-0300

$249,900

2 Beds ⋅ 2 Baths ⋅ 24208956 MLS ⋅ Pine Hill BLDG.

MAKE THIS RANCH STYLE END UNIT YOURS TODAY. Beautifully maintained with all the ease of true one-floor living in a tranquil, wooded setting. Discover the incredible peace of mind that comes with the convenience of driving into your private garage with direct access to your home. Features include a new roof, new back deck, new hot water heater, new high-efficiency heat pump condenser unit, and brand-new LG combination washer and dryer. Inside, the home feels incredibly welcoming with an open floor plan. The spacious kitchen is perfect for cooking and entertaining, complete with a large island, abundant cabinetry, and plenty of counter space. It flows effortlessly into the dining area and a comfortable living room, where a large slider lead out to your new private deck. It's the perfect quiet spot to sip your morning coffee or tea while enjoying the lovely, natural setting. The primary bedroom features a private full bathroom, a walk-in closet, and the ultimate convenience of that brand-new LG laundry unit right where you need it most. Downstairs, the large full basement provides all the storage space you need, and could easily be transformed into a workshop, craft area or exercise space. Location-wise, you get the absolute best of both worlds. While your backyard feels like a quiet sanctuary, the community itself is centrally located just minutes to fantastic shopping, dining, & recreation. Get cozy this winter season with one floor living and your own private garage too!

19 Wiggins Farm Dr Unit A, Simsbury

Listing courtesy of Bonnie Call from Century 21 AllPoints Realty. (860) 916-5688 (860) 675-0021

$325,000

4 Beds ⋅ 2 Baths ⋅ 24208688 MLS

Nestled in a quiet and desirable neighborhood, this classic Cape Cod-style home offers 4 spacious bedrooms, 2 full bathrooms, and 1,238 square feet of living space on a generous .49acre lot. Featuring timeless charm and plenty of potential, this property is an excellent opportunity for buyers looking to create a home tailored to their own style and needs. Inside, original hardwood floors add warmth and character throughout the living spaces. The main level offers a comfortable layout with ample living space, while the upper level features well-sized bedrooms. Outside, the spacious .49 acre lot provides room for gardening, recreation, entertaining, or future improvements. Relax on the back deck and enjoy the peaceful surroundings, birds, and views. Conveniently located near schools, parks, and local amenities, this Cape Cod offers a combination of location, space, and potential that makes it an exciting opportunity for the next owner.

7 Knollwood Cir, Simsbury

Listing courtesy of George Sznaj from DB Associates of CT, LLC. (860) 518-4049 (860) 518-4049

$379,000

2 Beds ⋅ 4 Baths ⋅ 24208094 MLS ⋅ Riverwalk BLDG.

Spacious and bright 2-bedroom, 3.5-bath townhome at popular Riverwalk in Simsbury. This lovely community is conveniently located in Weatogue close to town center. On the main level you will enjoy an open living and dining room area with plenty of space for friends and family, abundant natural light, a fireplace and slider access to the private deck. The kitchen is updated with granite counters, newer appliances, a gas range and offers eating space and large windows and slider. Upstairs you will find two bedrooms with vaulted ceilings and private baths. You will also enjoy the convenience of a second floor laundry room. Don't miss even more living space in the finished, heated walk-out lower level with full-bath. This space is perfect for a family room, office, guest space or 3rd bedroom. Special features include an attached garage, efficient natural gas heating and central air. Furnace and Hot Water heater new in 2022. This home is also conveniently located across the street from Weatogue Park and offers easy access to the Farmington Valley Greenway paved trail. Come fall in love with this beautiful home and location today.

5 Riverwalk Dr Unit 5, Simsbury

Listing courtesy of Gregory Frey from RE/MAX Prime Realty. (860) 716-2593 (860) 673-8700

$450,000

3 Beds ⋅ 3 Baths ⋅ 24188062 MLS

Tucked into historic Tariffville, this thoughtfully renovated Ranch features a completely rebuilt kitchen with custom cabinetry, quartz countertops, stainless steel appliances, and a dining area with wainscoting. A wide patio door connects the living room to the backyard. Both full baths are remodeled, and a cozy fireplace anchors the living space. The finished basement offers a home office, new flooring, and laundry room with built-in cabinetry. Outside, the large, fully fenced backyard features a low-maintenance composite deck and storage shed. Central air and solar panels provide year-round comfort and efficiency. Tariffville's village center sits along the Farmington River, known for whitewater kayaking and its National Register Historic District featuring mill housing and Greek Revival architecture. Enjoy the mill's restaurant, Rails to Trails bike path, or summer concerts at Simsbury Meadows Performing Arts Center. Located within the highly regarded Simsbury school system, with an easy commute to Hartford and Springfield. Move-in ready and full of character. Come see it for yourself.

81 Elm St, Simsbury

Listing courtesy of Jonathan Zuromski from Real Broker CT, LLC. (860) 385-6061 (855) 450-0442

$279,000

2 Beds ⋅ 3 Baths ⋅ 24207568 MLS ⋅ Pine Hill BLDG.

Welcome to easy, low-maintenance living in the heart of Simsbury! This move-in ready 2-bedroom, 2.5-bath condo appeals to all buyers. The inviting main level features a bright, functional layout with an open living & dining room and a well-appointed kitchen that's been tastefully updated. Upstairs, you'll find two generously sized bedrooms, with great natural light, plenty of closet space, fresh paint and 2 full bathrooms. Some recent improvements include, but are not limited to, a new hot water heater, new lighting throughout, fresh paint, a new storm door, and a new slider out to your private deck that overlooks the woods with steps to grade. The partially finished basement provides valuable additional living space-perfect for a home office, recreation room, gym, or hobby area-while still offering plenty of storage. A private garage adds the convenience of secure parking and additional storage space. This townhome is walking distance to the center of Simsbury and all that it has to offer as well as the hike and bike trail that stretches all through the Farmington Valley. Whether you're looking for your first home, a convenient downsize, or a low-maintenance place to call home, this turnkey condo is ready to welcome you! Professional photos coming soon!

12 Wiggins Farm Dr Unit C, Simsbury

Listing courtesy of Cassidy Davidson from William Raveis Real Estate. (860) 335-7144 (860) 677-4661

$374,900

3 Beds ⋅ 2 Baths ⋅ 24206800 MLS

Welcome to 8 Canton Road! A truly unique New England reproduction colonial built on the site of a former farm in 1953 by historian Edgar Brown of Simsbury in collaboration with architect John Berle. Set on a beautiful and private 0.55-acre lot in sought-after West Simsbury, this charming reproduction Colonial offers the perfect blend of comfort and tranquility. Inside, the home offers 3 bedrooms, 1.5 baths, inviting living space with a fireplace, and a full basement renovated to create an authentic Colonial tavern with bar. A special highlight of the property is the expansive backyard oasis, featuring a spacious deck overlooking serene, tree-lined grounds ideal for outdoor entertaining, gardening, or peaceful relaxation. Located just minutes from Simsbury Center, shopping, dining, and commuter routes, this home presents a rare opportunity to enjoy a private retreat in a premier location.

8 Canton Rd, Simsbury

Listing courtesy of Susan Foster from Coldwell Banker Realty. (860) 573-6791 (860) 674-0300

$249,900

2 Beds ⋅ 2 Baths ⋅ 24205483 MLS ⋅ Pine Hill BLDG.

Rarely available end-unit ranch condo with a new roof, new deck, new hot water heater, newer windows and heat pump, new dishwasher and brand-new washer and dryer in the highly sought-after Pine Hill community! Beautifully maintained, this charming 2-bedroom, 11/2-bath home offers convenient first-floor living, a peaceful wooded setting, and a prime location just minutes from Simsbury Center. The kitchen features tile flooring, a pantry, eat-in area, and a new dishwasher. The spacious, open-concept living and dining area includes sliders leading to the new private deck, where you can relax and enjoy tranquil wooded views. Both bedrooms offer generous space and ample closet storage. The primary bedroom features a private full bath. Additional highlights include an attached 2-car garage, brand-new washer and dryer, a new hot water heater, and a full basement with abundant storage and excellent potential for additional living space. Enjoy scenic trails, shopping, dining, and everything Simsbury has to offer from this exceptional Pine Hill location!

14 Wiggins Farm Dr Unit J, Simsbury

Listing courtesy of Jennifer Petron from Berkshire Hathaway NE Prop.. (860) 558-1880 (860) 658-1981

$359,900

2 Beds ⋅ 2 Baths ⋅ 24204262 MLS

What a GEM! This West Simsbury cutie will win your heart over the moment you set foot inside. If you've been dreaming of Autumn in New England, there is no better place to experience it than right here in Simsbury! Imagine crisp fall mornings heading out to local favorites like Flamig Farm for hayrides, picking fresh pumpkins and apples at The Pickin' Patch, or enjoying wine tastings and corn mazes at Rosedale Farm & Vineyard-all less than 5 miles from your front door. Take in breathtaking autumn foliage views from the top of Heublein Tower at Talcott Mountain State Park, grab a craft brew at Talcott Mountain Collective, or enjoy leaf-peeping along neighborhood strolls on your quiet corner lot. Inside, the home offers a bright and turn-key layout with an updated kitchen flowing into the dining area and a spacious living room featuring a cozy wood-burning fireplace and built-in shelving-perfect for warming up on chilly fall evenings. The brilliant rear flex-room addition offers endless versatility as a family hang-out space, home office, or guest room. Complete with updated full baths, new roof in 2025, main-level laundry, and a private backyard patio, this charming home packs a punch!

170 W Mountain Rd, Simsbury

Listing courtesy of Suzy Couture from Better Homes and Gardens Real Estate Executive Real Estate. (860) 944-4370 (860) 633-8800

$444,900

4 Beds ⋅ 2 Baths ⋅ 24205272 MLS

**HIGHEST AND BEST TERMS requested by 5 pm Tuesday September 15.** WOW! Impeccably maintained and truly move-in ready, this charming 4-bedroom Cape reflects pride of ownership throughout. Blending classic character with thoughtful updates, the home offers a spacious, comfortable and flexible floor plan with 2 full baths, beautiful hardwood floors, and wonderful natural light. The inviting eat-in kitchen features granite countertops, updated appliances, terrific storage and a skylight, creating a bright and welcoming space for everyday meals and gatherings. A sun-filled living room offers timeless warmth and character, while the separate family room-with additional skylights-provides the perfect spot for movie nights, relaxing, or casual entertaining. Outside, the beautifully landscaped property is just as impressive. The patio and landscaping were recently updated, complemented by additional newer landscaping and a retaining wall, creating an attractive setting for outdoor dining, entertaining, or simply enjoying the yard. Conveniently located with easy access to highways, Bradley International Airport, shopping, restaurants, and everyday amenities. Meticulously cared for, thoughtfully updated, and exceptionally well presented, this delightful Cape is ready for its next owners to simply move in and enjoy.

138 Tariffville Rd, Simsbury

Listing courtesy of Erica Maglieri from Berkshire Hathaway NE Prop.. (860) 324-6842 (860) 658-1981

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.