Cheshire, CT Homes for Sale

Your Dream Home in the Heart of Cheshire! Welcome to this stunning 5-bedroom/potential 7 bedroom, 5.5-bath Colonial located in the center of Cheshire. With over 5,000 sq. ft. of living space and set on more than an acre, this masterpiece offers the perfect blend of luxury, comfort, and convenience. The seller has spared no detail in the design and upkeep of this exceptional home. Main Floor

Amy LaMaster The Bella Group, LLC

The Carriage Home floor plan combines architectural elegance with EG Home's high-performance building standards. Constructed with 2 X 6 exterior walls, double-pane double hung windows, and a layered insulation system of spray foam, batting, and blown-in insulation, each home is built for quiet comfort and lasting energy efficiency. A cold-climate heat pump and Energy Recovery Ventilator (ERV)

Jason Helton EG Group Realty LLC

Build your dream Carriage Home from the ground up at The Reserve at Stonebridge Crossing-Cheshire's premier low-maintenance community by EG Home. This spacious 2,450 sq ft floor plan offers the perfect blend of comfort, flexibility, and energy efficiency, with the opportunity to personalize every detail. Create your ideal kitchen by selecting from EG Home's curated layouts, including our Pro

Michael Helmuth EG Group Realty LLC

Welcome to the opportunity to build your dream home in a highly desirable location. Nestled on a secluded rear lot that is just under an acre, this thoughtfully designed 4-bedroom, 2.5-bath Colonial will offer 2,792 square feet of beautifully crafted living space with the perfect blend of privacy and modern comfort. Designed with today's lifestyle in mind, the open concept layout will seamlessly

Michael Dziedzic Precision Realty LLC

Unique Multi-Home Property on Over 3 Private Acres! A rare opportunity to own two homes on one beautiful property in a peaceful, private setting. Property Highlights: Over 3 acres of land R-40 zoning - ideal for farming, gardening, horses, or hobby farm potential Quiet country setting surrounded by nature Endless possibilities for multi-generational living, rental income, or guest house Main

Nancy Newman LPT Realty

Brand-new construction completed on 12/12/2025 and currently receiving final finishing touches by the owner. This beautiful home offers 4 spacious bedrooms, 3 full bathrooms, and a 2-car garage with an additional 506 square feet of garage space. The Town has issued the Certificate of Occupancy (CO). Thoughtfully designed layout with modern finishes throughout. A rare opportunity to own a newly

Carlos Ventura Ventura Group Realty LLC

Tucked away on 4 private wooded acres, this charming Dutch Colonial offers the perfect blend of peaceful country living and modern comfort, just minutes from town. Inside, the home offers 3,300 SF of inviting living space filled with natural light, warm wood floors, exposed beams and lovely built-ins. The recently updated spacious kitchen with new wood flooring, new quartz countertops and new

Rose Ciardiello William Raveis Real Estate

This house is 45 days from completion! Framed, siding, windows, Heating/AC, Hardwood, baths, kitchen are all in process or done! GREAT NEW CONSTRUCTION READY FOR QUICK DELIVERY FOR NEW OWNERS!! Pictures at end of what same house looked like. GREAT OPPORTUNITY for new homeowners for a new house without any waiting or hassles! Amazing open layout on this modern colonial. This home is perfect for

Roy Evjen Evjen Agency

Beautifully maintained and truly move-in ready, this 4-bedroom Colonial is tucked away on a quiet cul-de-sac in a desirable, family-friendly neighborhood. Thoughtfully designed for today's lifestyle, the home features white oak flooring and 9-foot ceilings throughout the main level, creating a bright and inviting atmosphere. The updated eat-in kitchen flows seamlessly into the family room,

Brette Stern Calcagni Real Estate

Don't miss this rare opportunity to own a truly one-of-a-kind property offering exceptional space, flexibility, and amenities. This 3,600+ SF home features 4 bedrooms, 4.5 baths, including a versatile in-law apartment, home gym, plus two garages with plenty of room for multiple cars. The original 1900 colonial main house blends classic charm with modern updates, offering three bedrooms, 1.5

Heidi Hoss Coldwell Banker Realty

Inspiring country home. Inground pool, tennis court and equestrian features.

Joel Matson Coldwell Banker Realty

Have you been DREAMING of a new construction home but don't have the time to wait for it to be built? Say HELLO to 16 Melrose Drive! This Nearly New construction Colonial is 3 years young and offers the perfect blend of modern design and timeless charm. This beautifully maintained home features a thoughtfully designed layout with today's lifestyle in mind. This home features a bright and open

Dori Degennaro William Raveis Real Estate

Beautifully maintained raised ranch located on a quiet cul-de-sac in the desirable north end of Cheshire. This spacious home offers over 1,700 SQ FT of living space on main level, featuring a bright living room that flows into a formal dining area with direct access to a rear deck overlooking a huge backyard. The updated kitchen offers stainless steel appliances, a tile backsplash, breakfast bar

Jack Hill Seabury Hill REALTORS

Welcome to Southwick, Cheshire's Premier 55+ Community! This beautifully Remodeled 2 bedroom, 2 bath Ranch unit offers one-floor living and exceptional space in a peaceful, private community. Step into a sun-filled open layout featuring NEW laminate flooring throughout. Fully applianced Kitchen with Granite countertops and oak cabinets provide ample storage. Off the living/dining room is a large

Julie Luchina Coldwell Banker Realty

Nicely maintained 4-bedroom, 2 full bath split-level home offering 1,488 sq. ft. of living space plus an additional 216 sq. ft. in the finished lower level with walk-out access. This home features hardwood flooring and a bright, inviting living room with a large bow window and a cozy brick-faced raised hearth fireplace with wood-burning insert. The spacious kitchen offers white cabinetry,

Katie Smith Berkshire Hathaway NE Prop.

Welcome to this charming ranch style single family home, thoughtfully updated and conveniently located just minutes from I84 and Route 8, with easy access to the Merritt Parkway and I91 for an easy commute. From the moment you walk in, you will appreciate the bright and refreshed feel throughout. The kitchen has been updated with quartz countertops, stainless steel appliances, and brand new

Eric Chou eXp Realty

Inquire immediately-ask your agent to secure this one before it's gone. Welcome to 840 Westside Road in Cheshire, a beautifully updated and meticulously cared-for home set on a prime lot in one of the area's more desirable neighborhoods. From the moment you arrive, you'll notice the curb appeal and thoughtful landscaping. Inside, the home features a stylish NEW kitchen opening seamlessly to the

Sam Ratner Keller Williams Realty Prtnrs.

Desirable Cheshire neighborhood. Step into this inviting 3bedroom, 2.5bath home and feel the possibilities open up. The moment you walk in, you're greeted by a bright open floor plan that's perfect for everyday living and effortless entertaining. Updated kitchen and bathrooms. The primary bedroom offers comfort and convenience with its own full ensuite bath. Head outside and you'll find a

Frank Lazowski Laz Real Estate, LLC

Welcome to Old Towne Condos, a highly desirable center-of-town community offering convenience & walkability. This spacious 1,536 sq. ft., 2-bedroom, 2-1/2 bath Townhouse unit features a welcoming eat-in kitchen at the front of the home, a formal dining room, and a sunken living room complete with a wood-burning fireplace and French doors leading to a covered sun porch. The porch overlooks a very

The Sally Bowman Team Berkshire Hathaway NE Prop.

Investors take notice. House needs total renovation.Being sold as is where is including contents. Cash Offers Only Highest and best offers by 4:00pm on Monday 3/30/2026

Phil Giampietro Coldwell Banker Realty

This beautiful one bedroom of Southwick at Cheshire is just what you've been looking for. Southwick at Cheshire is a 55+ community with beautiful grounds, a cozy communal library, billiard room, and many common spaces for social exchange. This single owner unit has been thoughtfully maintained for nearly 20 years. Upgrades include maple hardwood floors throughout kitchen and dining/living area,

Rebecca Bower Forever Homes Real Estate LLC

Opportunity knocks in this ranch located in a desirable central Cheshire neighborhood with sidewalks to schools, shopping, and parks. This 3-bedroom home with 1 full and 2 half baths offers great space, a wonderful setting, and endless potential for the buyer ready to make it their own. Upon entry, you will find a spacious living room that is adjacent to an eat-in kitchen and a hallway that leads

Brette Stern Calcagni Real Estate

Welcome to 365 Maple Ave, a quintessential Cheshire Colonial where timeless New England charm meets you at the front door & is the backdrop of every room. Curb appeal abounds with crisp white siding, a brand-new roof (1.5 yrs), and iconic red accents. Once you step inside, you won't be able to stop yourself from wanting to wander & immerse yourself in each and every room! The heart of the home is

Suzy Couture Executive Real Estate Inc.

A rare opportunity to own the Reverend John Hull House at Stonebridge, a 55+ community in Cheshire. This home was originally built in 1764 but was gutted and restored for today's living in 2005, still keeping all it's historic charm and features such as original wide plank flooring, exposed hand-hewn beams and 4 fireplaces (3 functioning w gas). The spacious Living Room w large gas FP creates a

Phil Giampietro Coldwell Banker Realty

Welcome to 1244 Long Hill Road, where comfort, style, and functionality come together seamlessly. This charming 3-bedroom residence offers an inviting, floor plan complemented by thoughtful updates throughout. Step inside to a spacious living and dining area, perfect for both entertaining and everyday living. The kitchen features updated appliances and sleek granite countertops, providing a

Michael Barbaro Huntsman,Meade & Partners Comp

Rare Opportunity at Regency of Prospect - an affordable housing unit! Enjoy this beautifully maintained, 55+, gated community. This bright, 10-year-young home offers comfort, convenience, and an active lifestyle. The open concept main level is filled with natural light! It features a welcoming kitchen with a breakfast bar and flows easily into the dining and living areas. The living room offers

Christine Lovejoy Houlihan Lawrence WD