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Homes for Sale near Highland School

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  • /34

    $525,000

    • 3 Beds
    • 3 Baths
    • 2,330 Sq Ft

    1013 Wallingford Rd, Cheshire, CT 06410

    Experience Tranquil Rural Living in Your Multi-Generational Dream Home! This stunning property offers a blend of modern amenities and serene rural living, perfect for households of all sizes. Step into a cozy sunken living room, featuring elegant French doors that open to a spacious patio, ideal for indoor-outdoor entertaining. Enjoy cooking in a sleek, modern kitchen equipped with quality

    Agent Photo

    Mark Mnich

    Coldwell Banker Realty

    (475) 281-3540

    1013 Wallingford Rd, Cheshire, CT 06410
  • /3

    $1,060,000 New Construction

    • 4 Beds
    • 3 Baths
    • 3,029 Sq Ft

    1500 Blackberry Place, Cheshire, CT 06410

    Welcome to Blackberry Woods, Cheshire's newest development. Consider The Willow, with its 3,029 sqft of Living Space on just over 1.36 Acres of Land. Fabulous Floor Plan includes an impressive 2 Story Foyer, First-Floor Full Bath, Large Kitchen Pantry, and Private Office on the Main Level. The Master Suite will "WOW" You with a Walk-In Closet, Double Vanities, Water Closet, and a Luxurious

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 427-0372

    1500 Blackberry Place, Cheshire, CT 06410
  • /21

    $829,000 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,001 Sq Ft

    1517 Blackberry Place, Cheshire, CT 06410

    Exciting opportunity to build your very own 2001 sqft ranch with wonderful curb appeal. One level living at its finest, with 9ft ceilings throughout, custom kitchen w/granite countertops and center island, hardwood flooring in the main living areas, gas fireplace in the family room and a mudroom with half bath and laundry. Large Primary bedroom with bathroom en-suite, and walk-in closet. 2 guest

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 457-3624

    1517 Blackberry Place, Cheshire, CT 06410
  • /2

    $929,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,794 Sq Ft

    1841 Blackberry Place, Cheshire, CT 06410

    Stunning 4 bedroom, 2.5 bathroom Colonial, The Birch offers gracious living and a wonderful floor plan. Culinary enthusiasts will love the large walk in pantry, granite-topped cabinetry with center island that opens to a spacious family room with vaulted ceiling. The wonderful layout for entertaining is completed by a formal dining room. Easily work from home with the main floor study. The

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (475) 472-8934

    1841 Blackberry Place, Cheshire, CT 06410
  • /2

    $919,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,718 Sq Ft

    1800 Blackberry Place, Cheshire, CT 06410

    Build your own expanded Cape Cod (or bring your own plans) on Blackberry Woods, Cheshire's newest development. 4 bedroom, 2.5 bathroom Maple model with a primary bedroom on the main floor. Oversized family room with fireplace opens to a custom kitchen with island. Formal dining room for get togethers and events. The 1st floor hosts the primary suite with large walk in closet and tile shower, and

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    Kathleen Maloney

    Coldwell Banker Realty

    (475) 445-2914

    1800 Blackberry Place, Cheshire, CT 06410
  • /3

    $890,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    1517A Blackberry Place, Cheshire, CT 06410

    Build the custom home of your dreams on ~ 1 acre of land in Blackberry Woods. Consider the Spruce model which offers 2,600 sqft of living space w/ 4 Bedrooms and 2 1/2 Baths. It includes a spacious foyer with double coat closets, mudroom, half bath & laundry off garage entry, an open floor plan between the family room, dinette & kitchen, gas log fireplace, and kitchen pantry. The formal dining

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 590-8495

    1517A Blackberry Place, Cheshire, CT 06410
  • /4

    $869,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,459 Sq Ft

    1511 Blackberry Place, Cheshire, CT 06410

    Under construction in a neighborhood setting-Cheshire's newest development. Blackberry Woods. The gracious Charter Oak model provides 2,459 sq ft of thoughtful living space with 4 Bedrooms and 2 1/2 Baths. Desirable features of this plan include a spacious foyer entry with coat closet, mudroom off the garage entry w/ half bath and laundry, an open floor plan including a custom kitchen, dinette &

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 718-0345

    1511 Blackberry Place, Cheshire, CT 06410
  • /3

    $987,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,821 Sq Ft

    1600 Blackberry Place, Cheshire, CT 06410

    Welcome to Blackberry Woods. Enjoy the Frasier model with 2,821 sqft of living space , w/ 4 Bedrooms and 2 1/2 Baths. This both elegant and practical model features a spacious Foyer with double coat closets, Mudroom and Half Bath off garage entry, open floor plan between the Family Room, Dinette & Kitchen, Gas Log Fireplace, Kitchen Pantry, and a backyard Patio with built-in Firepit! The formal

    Agent Photo

    Kathleen Maloney

    Coldwell Banker Realty

    (203) 496-4049

    1600 Blackberry Place, Cheshire, CT 06410
  • /17

    $518,990 Open Sat 12PM - 3PM

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    7 Soderman Way Unit 7, Cheshire, CT 06410

    Welcome to The Reserve at Stonebridge Crossing - Where Lifestyle Meets Luxury! Set in the heart of New Haven County in Cheshire, The Reserve at Stonebridge Crossing offers the perfect blend of convenience, charm, and low-maintenance living. Now available: our award-winning Townhouse floor plan, previously showcased as our designer model home! This thoughtfully planned community will soon feature

    Jason Helton EG Group Realty

    7 Soderman Way Unit 7, Cheshire, CT 06410
  • /37

    $1,250,000

    • 5 Beds
    • 5.5 Baths
    • 5,081 Sq Ft

    435 Maple Ave, Cheshire, CT 06410

    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

    435 Maple Ave, Cheshire, CT 06410
  • /13

    $669,900 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    85 Shea Cir Unit 85, Cheshire, CT 06410

    Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy,

    Jason Helton EG Group Realty

    85 Shea Cir Unit 85, Cheshire, CT 06410
  • /20

    $534,900 Open Sat 12PM - 3PM

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    129 Shea Cir Unit 129, Cheshire, CT 06410

    DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious exterior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers

    Jason Helton EG Group Realty

    129 Shea Cir Unit 129, Cheshire, CT 06410
  • /13

    $778,572 Open Sat 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,975 Sq Ft

    81 Shea Cir, Cheshire, CT 06410

    Carriage home complete with designer appointed finishes! Available in the Summer of 2025. Carriage Home is stylish and sophisticated, yet every bit as warm, our Carriage homes provide the perfect mix of luxury, function, and comfort. You'll feel its charm upon entering the foyer, which leads to the heart of the home. A bright, open kitchen overlooks the dining area and wow-factor, the 2-story

    Felicity LeClair EG Group Realty

    81 Shea Cir, Cheshire, CT 06410
  • /40

    $829,000

    • 3 Beds
    • 3.5 Baths
    • 4,059 Sq Ft

    430 Cook Hill Rd, Cheshire, CT 06410

    Welcome to 430 Cook Hill Rd - a private retreat in the heart of Cheshire! This stunning home offers over 4,000 sq ft of finished living space on a 3.64-acre open and level lot, just minutes from top-rated schools, shopping, restaurants, and town amenities. The property is expansive with open land ready for entertaining, gardening, or a future pool. Step inside to discover a thoughtful layout,

    Kyle Howles Better Living Realty, LLC

    430 Cook Hill Rd, Cheshire, CT 06410
  • /34

    $799,999

    • 3 Beds
    • 2 Baths
    • 2,345 Sq Ft

    625 Tamarack Rd, Cheshire, CT 06410

    This immaculate 3 bedroom, 2 bath split-level ranch sits on a well-manicured 1.84 acre lot, lined with luscious trees in the backyard for extra privacy. 625 Tamarack Rd's open floor plan with floor-to-ceiling windows allows for a flood of natural light all throughout the house! Gleaming hardwood floors throughout this main level with granite accents offer a luxurious vibe without being

    Peter Digangi Dow Della Valle

    625 Tamarack Rd, Cheshire, CT 06410
  • /26

    $850,000

    • 5 Beds
    • 3 Baths
    • 4,352 Sq Ft

    1731 Marion Rd, Cheshire, CT 06410

    The Newman Compound! You are going to love this sprawling ranch that includes two houses! The guest house is fully rented. This home is truly spectacular. The floor plan is open & huge. The main house has 4+ bedrooms. Full finished lower level features large family room accented by a wood stove, office, additional bedrooms & a full bathroom. Beautiful stream on boundary. Both houses 1731 & 1735

    Nancy Newman LPT Realty

    1731 Marion Rd, Cheshire, CT 06410
  • /29

    $1,150,000 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,832 Sq Ft

    23 Melrose Dr, Cheshire, CT 06410

    23 Melrose Dr is nearly complete and ready for you to move in and call it HOME! This is a beautifully designed classic New England Cape Farmhouse-where timeless tradition meets thoughtful modern upgrades. This home boasts classic curb appeal with its inviting front porch, classic New England shaker style siding and stylish black exterior windows. Step inside to discover a light-filled interior

    Dori Degennaro William Raveis Real Estate

    23 Melrose Dr, Cheshire, CT 06410
  • /30

    $1,299,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 3,775 Sq Ft

    1481 Marion Rd, Cheshire, CT 06410

    Inquire about special builder incentives available until June 30th! Welcome to Blackberry Woods, Cheshire's newest neighborhood! This private, secluded lot presents a rare opportunity to build your dream home with a respected local builder known for quality craftsmanship, meticulous attention to detail, and energy-efficient design. The Magnolia model showcases 9' ceilings, hardwood flooring in

    Abby Breau New England Prestige Realty

    1481 Marion Rd, Cheshire, CT 06410
  • /5

    $1,299,000 New Construction

    • 4 Beds
    • 4.5 Baths
    • 4,011 Sq Ft

    15 Melrose Dr Unit Lot 4, Cheshire, CT 06410

    Presenting 15 Melrose Drive! This beautiful, To Be Built, new construction home is the layout that you have been waiting for! At 4,011 square feet this house plan is the perfect size for any family. A very spacious home with 9 ft ceilings on the main level, and a beautiful cathedral ceiling in the Family Room that perfectly highlights the decorative propane fireplace. A very functional mudroom

    Dori Degennaro William Raveis Real Estate

    15 Melrose Dr Unit Lot 4, Cheshire, CT 06410
  • /14

    $549,999 Open Sun 12PM - 3PM

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    4 Soderman Way Unit 4, Cheshire, CT 06410

    Motivated Seller! Skip the wait on new construction and step into this upgraded end-unit townhome at The Reserve at Stonebridge Crossing. Featuring 2 bedrooms plus a flexible room with elegant French doors-perfect as a home office, guest space, or third bedroom. Inside you'll find GE Cafe appliances, upgraded flooring, trim, and premium hardware throughout. One of the few homes in the community

    Khaliq Brown CLMA Realty

    4 Soderman Way Unit 4, Cheshire, CT 06410
  • /29

    $469,000

    • 3 Beds
    • 2 Baths
    • 1,508 Sq Ft

    498 Juniper Ln, Cheshire, CT 06410

    This thoughtfully updated 3-bedroom, 2-full bathroom ranch offers effortless one-level living in a desirable Cheshire location directly across from McNamara Field Park-ideal for morning walks, weekend sports, or a relaxed picnic just steps from your door. Inside, an open-concept layout connects the living and dining spaces, complete with a gas fireplace and updated flooring throughout. The

    Alex Capozzoli Keller Williams Realty

    498 Juniper Ln, Cheshire, CT 06410
  • /27

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,254 Sq Ft

    114 E Mitchell Ave, Cheshire, CT 06410

    Welcome to 114 E. Mitchell Avenue - a charming 3-bedroom, 1-bath home tucked away from the main road in one of Cheshire's most desirable neighborhoods. This cozy retreat strikes the perfect balance of privacy, natural beauty, and community charm, making it an ideal home for families, pet lovers, or anyone seeking a peaceful lifestyle with nearby amenities. Inside, you'll find a bright living

    Jessica Boswell LPT Realty

    114 E Mitchell Ave, Cheshire, CT 06410
  • /9

    $309,900

    • 3 Beds
    • 1 Bath
    • 900 Sq Ft

    445 Lincoln Dr, Cheshire, CT 06410

    Three Bedroom raised ranch for sale in desirable Cheshire. Home being sold as-is, where-is. See the upside potential, see the resale value and/or rental value, and make your offer. Come see the tranquil neighborhood and nearby area, and fully enjoy. Investors, and those seeking a home that is not over-priced; come make this yours.

    Justin Marino Marino Realty LLC

    445 Lincoln Dr, Cheshire, CT 06410
  • /6

    $394,900

    • 3 Beds
    • 1.5 Baths
    • 1,512 Sq Ft

    3 Cedar Ln, Cheshire, CT 06410

    Welcome to this spacious 8-room, multifunctional ranch, featuring 3 bedrooms and perfectly designed for a home-based office or business. The inviting living room, complete with a wet bar and fireplace, is ideal for entertaining. A doorway leads to the business wing, consisting of three rooms, a kitchen nook, and a half bath. This area also has a separate entrance that opens to a cement patio,

    Colleen Caron Barrieau Realty Signature Prop

    3 Cedar Ln, Cheshire, CT 06410
  • /7

    $335,000

    • Land
    • 1.00 Acre
    • $335,000 per Acre

    6 Waterside Way, Cheshire, CT 06410

    Unique opportunity to own Waterfrontage in Cheshire. This one of a kind planned unit development, sitting on the pristine Lake Percival with an exquisite waterfall is offering a 1-acre lot available to build your dream home. The location of the former Percival Estate home boasts vast views of the pond from the building area, with no flood insurance required, bring your contractor to lay out your

    Anthony LaCava Berkshire Hathaway NE Prop.

    6 Waterside Way, Cheshire, CT 06410
  • /4

    $335,000

    • Land
    • 1.32 Acres
    • $253,788 per Acre

    5 Waterside Way, Cheshire, CT 06410

    Unique opportunity to own Waterfrontage in Cheshire. This one of a kind planned unit development, sitting on the pristine Lake Percival with an exquisite waterfall is offering a 1.32 acre lot available to build your dream home. Boasting vast views of the pond from the building area, with no flood insurance required, bring your contractor to lay out your vision today, or contractor consultations

    Anthony LaCava Berkshire Hathaway NE Prop.

    5 Waterside Way, Cheshire, CT 06410
  • /40

    $2,200,000

    • 5 Beds
    • 4.5 Baths
    • 3,174 Sq Ft

    630 Cook Hill Rd, Cheshire, CT 06410

    Welcome to your own piece of heaven on Earth! This Cape Cod gem boasts not just a home but a lifestyle surrounded by 8.5 acres of sprawling land, perfect for your own little homestead. Inside you will find a Chef's Dream, an expansive eat-in kitchen that's the heart of the home that includes a colossal 10x5 island for gatherings, an additional prep island for culinary adventures, and a wet bar

    Kelsey Oddo Kelsey & Co. Real Estate

    630 Cook Hill Rd, Cheshire, CT 06410
  • /2

    $169,900

    • Land
    • 1.22 Acres
    • $139,262 per Acre

    0 Moss Farms Rd, Cheshire, CT 06410

    Approved and cleared .93+/- acre rear building lot located behind 916 Moss Farms Rd, Cheshire. Maps available upon request. Please do not walk property without a scheduled appointment. Contact for additional information. Subject to easements and approval stipulations.

    Jorge Zea Blue Lighthouse Realty, Inc

    0 Moss Farms Rd, Cheshire, CT 06410
  • /13

    $674,900 Open Sat 12PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,450 Sq Ft

    87 Shea Cir Unit 87, Cheshire, CT 06410

    Build Your Dream Home at The Reserve at Stonebridge Crossing! Design a home that truly reflects your style in Cheshire's premier new home community. At The Reserve, you'll work with our expert team to personalize every detail-from structural options to designer finishes-through our elevated and streamlined design process. Our Zero Energy Ready homes, certified by the Department of Energy,

    Michael Helmuth EG Group Realty

    87 Shea Cir Unit 87, Cheshire, CT 06410
  • /20

    $544,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,850 Sq Ft

    133 Shea Cir Unit 133, Cheshire, CT 06410

    DISCOVER THE RESERVE AT STONEBRIDGE CROSSING From its location to its variety of home styles. The Reserve at Stonebridge Crossing has the life - and lifestyle - you've been searching for in New Haven County. A spacious exterior unit townhome in a desirable location. This maintenance-free community will have a covered pavilion, fire pit, walking loop, and trails. A convenient location offers

    Michael Helmuth EG Group Realty

    133 Shea Cir Unit 133, Cheshire, CT 06410
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