Homes for Sale near J. Milton Jeffrey Elementary School

• 

  

  

  /40

  $2,450,000

  • 5 Beds
  • 7.5 Baths
  • 8,476 Sq Ft

  75 Half Mile Rd, Guilford, CT 06437

  Introducing a custom-built Adirondack-style masterpiece, set on over 5 acres of pristine land. Designed with care by the current owners, this home boasts a seamless layout, ideal for entertaining. Spacious, elegantly appointed rooms feature a custom-designed kitchen, soaring ceilings, and a stunning two-sided stone fireplace. Each bedroom is en suite, offering both privacy and luxury. The

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 350-7021

  75 Half Mile Rd, Guilford, CT 06437
• 

  Explore J. Milton Jeffrey Elementary School

• 

  

  

  /10

  $875,000 Coming Soon

  • 4 Beds
  • 4 Baths
  • 3,972 Sq Ft

  23 Horsebarn Ln, Madison, CT 06443

  Welcome to 23 Horsebarn Lane, one of the most versatile homes you will find on the market. From the newly renovated kitchen (new counters being installed soon!) to the expansive open layout, to the first floor master suite with fireplace, this home will check all the boxes for even the most discerning buyers. The expansive 2 story foyer creates a dramatic entry while also offering easy access to

  

  Dylan Walter

  William Raveis Real Estate

  (203) 594-8451

  23 Horsebarn Ln, Madison, CT 06443
• 

  

  

  /40

  $995,000

  • 4 Beds
  • 2.5 Baths
  • 2,632 Sq Ft

  97 Kelsey Springs Dr, Madison, CT 06443

  Beautiful 4-Bedroom Colonial in a Prime Madison Location! This immaculate home has been thoughtfully upgraded nothing left to do but move in and enjoy. The living room blends contemporary design with classic appeal, while the dedicated office provides the perfect space for working from home. A cozy family room with custom built-ins, a fantastic mud/laundry room, and four spacious bedrooms

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 323-6765

  97 Kelsey Springs Dr, Madison, CT 06443
• 

  

  

  /40

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 4,988 Sq Ft

  123 Liberty St, Madison, CT 06443

  Welcome to Liberty Street - One of Madison's Most Sought-After Addresses. This exceptional custom-built home combines timeless elegance with masterful craftsmanship, showcasing exquisite millwork and refined finishes throughout. Spend warm summer evenings on the inviting covered front porch, or step inside to find a beautifully designed interior featuring coffered ceilings in the dining room, a

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 260-9240

  123 Liberty St, Madison, CT 06443
• 

  

  

  /40

  $695,000

  • 4 Beds
  • 3 Baths
  • 2,555 Sq Ft

  16 Eastwood Rd, Madison, CT 06443

  Welcome to 16 Eastwood Drive, a beautifully updated raised ranch set on over an acre of land in one of Madison's most peaceful neighborhoods. This spacious 4-bedroom, 3-bathroom home offers over 2,555 square feet of living space with a bright and functional layout. The property has been thoughtfully upgraded throughout, featuring a brand-new roof, all new windows, and completely updated

  

  Nancy Potts

  Coldwell Banker Realty

  (475) 284-5986

  16 Eastwood Rd, Madison, CT 06443
• 

  

  /29

  $515,000

  • 2 Beds
  • 2.5 Baths
  • 2,320 Sq Ft

  40 Legend Hill Rd, Madison, CT 06443

  Carefree Living in Madison's Premier Legend Hill Community Set on over 80 acres of beautifully landscaped grounds, Legend Hill offers resort-style amenities including a historic clubhouse, inground pool, and tennis/pickleball courts-all just minutes from Madison's charming town center and sandy beaches. This meticulously maintained ranch style 2-bedroom unit has a lovely kitchen which opens to

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 779-6103

  40 Legend Hill Rd, Madison, CT 06443
• 

  

  /15

  $173,500

  • Land
  • 1.55 Acres
  • $111,935 per Acre

  728 Durham Rd, Madison, CT 06443

  Imagine building your dream home on this picturesque 1.55-acre lot in Madison, Connecticut, offering seasonal views of the serene Hog Pond. Throughout the year, enjoy the changing scenery and abundant wildlife, with opportunities for ice skating and hockey on the pond during winter months. The property includes a recent survey with topographical details and a septic design, pending only perc

  

  Gene Pica

  RE/MAX Alliance

  (475) 290-6060

  728 Durham Rd, Madison, CT 06443
• 

  

  /40

  $1,995,000

  • 5 Beds
  • 3.5 Baths
  • 3,912 Sq Ft

  30 Meeting House Ln, Madison, CT 06443

  Once known as "Hartsbourne," this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home

  

  Cathy Lynch

  Coldwell Banker Realty

  (203) 442-9594

  30 Meeting House Ln, Madison, CT 06443
• 

  

  /40

  $3,000,000

  • 6 Beds
  • 4.5 Baths
  • 6,300 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  Welcome to 37 Lantern Hill Road, a luxurious residence nestled in the heart of Madison's most coveted neighborhood. Just a short stroll from pristine beaches, the charming town center, and the Madison Country Club, this home offers an unparalleled lifestyle of comfort and convenience. Tucked away along picturesque brick-lined sidewalks and illuminated by classic lanterns, this exceptional

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 283-9847

  37 Lantern Hill Rd, Madison, CT 06443
• 

  

  /40

  $750,000 New Construction

  • 3 Beds
  • 3 Baths
  • 2,400 Sq Ft

  32 Cream Pot Rd, Clinton, CT 06413

  Set into the woods of Clinton, this 2,400 sq ft modern farmhouse is designed for the discerning, uninhibited buyer. With bold lines, glass walls, and a wide-open floor plan, it blurs the line between indoor and outdoor living. Inspired by Guilford's iconic Little Red Shack, the home celebrates transparency, minimalism, and architectural bravery. The main level features floor-to-ceiling glass,

  

  Dylan Walter

  William Raveis Real Estate

  (860) 385-6599

  32 Cream Pot Rd, Clinton, CT 06413
• 

  

  /35

  $1,500,000

  • 4 Beds
  • 3 Baths
  • 1,999 Sq Ft

  115 Harbor Ave, Madison, CT 06443

  Live the shoreline lifestyle in this beautifully updated 4-6 bedroom, 3-bath Colonial, just 88 steps from your very own private beach. Perfectly designed for both everyday living and entertaining, the open-concept main level flows seamlessly from dining to living, anchored by a cozy fireplace and filled with natural light. A screened-in porch with sweeping water views sets the stage for morning

  Alan Spotlow William Raveis Real Estate

  115 Harbor Ave, Madison, CT 06443
• 

  

  /38

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 3,986 Sq Ft

  16 Yankee Peddler Path, Madison, CT 06443

  This fully renovated and expanded Farmhouse Colonial offers nearly 4,000 sq ft of luxurious living space on a private 1.6-acre lot, blending timeless charm with modern upgrades. Every detail has been thoughtfully updated from roof to flooring, including new HVAC system, electrical, plumbing, a gourmet kitchen with center island and huge walk-in pantry, stylish bathrooms, and more. With 4 spacious

  Linda Toscano Coldwell Banker Realty

  16 Yankee Peddler Path, Madison, CT 06443
• 

  

  /39

  $876,500

  • 5 Beds
  • 3 Baths
  • 3,992 Sq Ft

  16 Forest Hills Dr, Madison, CT 06443

  Located in one of Madison's most desirable neighborhoods, 16 Forest Hills Drive offers exceptional space and potential. Just minutes from the town center and beaches. This expansive five-bedroom Colonial features an large eat-in kitchen with a cozy fireplace, a spacious formal living room with its own fireplace, and a versatile den/office with extensive built-in cabinets or family room-also with

  Rod Cross Coldwell Banker Realty

  16 Forest Hills Dr, Madison, CT 06443
• 

  

  /39

  $995,000

  • 5 Beds
  • 3.5 Baths
  • 4,168 Sq Ft

  66 Beaver Pond Rd, Madison, CT 06443

  Spacious Colonial close to Town Center boasting unique first floor, handicap accessible, in-law apartment with separate entrance, full kitchen, large family room and bedroom suite. Main house embraces a renovated granite kitchen, 4 additional second floor bedrooms including primary suite and great room with fireplace. Floor plan is tailor made for large gatherings. The home's kitchen and

  John Campbell Compass Connecticut, LLC

  66 Beaver Pond Rd, Madison, CT 06443
• 

  

  /27

  $1,300,000

  • 2 Beds
  • 2.5 Baths
  • 2,524 Sq Ft

  120 N Fair St Unit 2C, Guilford, CT 06437

  Downtown Guilford ranch living like you HAVE NEVER SEEN! This 2,500+ sq ft condo is stunning beyond words. Step inside & be wowed by high ceilings, exposed stone, incredible finishes,& an open floor plan filled with natural light. Rich hardwood floors run throughout. The kitchen is a showstopper with an oversized island that seats up to 5, abundant custom cabinetry & a large pantry. Top of the

  Susan Santoro William Pitt Sotheby's Int'l

  120 N Fair St Unit 2C, Guilford, CT 06437
• 

  

  /40

  $1,499,000

  • 4 Beds
  • 3.5 Baths
  • 5,267 Sq Ft

  625 State St, Guilford, CT 06437

  Welcome to State Street Haven, an exquisite Georgian-inspired mansion at 625 State Street in the heart of Guilford. Ideally located just minutes from town and nearby neighborhoods, this home offers both convenience and a prestigious address. Every detail exudes sophistication-from the sweeping staircase and soaring ceilings to the updated kitchen and luxurious bathrooms with chandeliers. Four

  Paige Slocum William Raveis Real Estate

  625 State St, Guilford, CT 06437
• 

  

  /34

  $3,200,000

  • 3 Beds
  • 3 Baths
  • 2,797 Sq Ft

  66 High St Unit 38, Guilford, CT 06437

  This stunning luxury condominium seamlessly blends sophistication and comfort. Completely customized and upgraded in 2023, this "double" upper unit in the Leete Building of The Residences at 66 High Street has seen very light use since completion. This home features a generously sized living room with fireplace, perfect for entertaining or unwinding in style and a dedicated dining area with

  Margaret Muir William Pitt Sotheby's Int'l

  66 High St Unit 38, Guilford, CT 06437
• 

  

  /40

  $1,675,000

  • 5 Beds
  • 3.5 Baths
  • 4,350 Sq Ft

  324 Tanner Marsh Rd, Guilford, CT 06437

  Rare offering on sought-after Tanner Marsh Road! This elegant home stuns from the street with its stone walls, circular driveway, and professionally landscaped grounds. Designed for entertaining, its rooms offer exceptional grace and flow. Three fireplaces, chef's kitchen with Viking appliances, first-floor guest suite with bath and private entrance - this home has it all! Master bedroom with

  Rose Ciardiello William Raveis Real Estate

  324 Tanner Marsh Rd, Guilford, CT 06437
• 

  

  /40

  $1,485,000

  • 5 Beds
  • 5 Baths
  • 5,779 Sq Ft

  110 Randi Dr, Madison, CT 06443

  A stately circular driveway ushers you into a realm of elegance & comfort. This grand & classic 5,779 sf residence is a testament to luxurious living, offering a harmonious blend of expansive open areas. Step through the front door and be greeted by a formal living room adorned w/ French doors & the first of 3 fireplaces, a space that could effortlessly transition into a distinguished home

  Amy Kirst William Pitt Sotheby's Int'l

  110 Randi Dr, Madison, CT 06443
• 

  

  /23

  $789,900

  • 4 Beds
  • 2.5 Baths
  • 2,805 Sq Ft

  18 Kelsey Springs Dr, Madison, CT 06443

  Charming colonial home nestled on 0.96 acres in a desirable neighborhood just minutes from the town beach, shopping, and highway. This beautiful 2800 square foot home boasts an open floor plan perfect for entertaining, with vaulted ceilings and a cozy fireplace. The spacious layout includes four bedrooms, two full baths, and one half bath, partial finished walk out basement and 2 car garage.

  Joanne Fowler Bishop, Edward & Roberts, LLC

  18 Kelsey Springs Dr, Madison, CT 06443
• 

  

  /36

  $1,000,000

  • 2 Beds
  • 2 Baths
  • 930 Sq Ft

  62 Cedar Island Ave, Clinton, CT 06413

  RARE OFFERING It's not often a property like this becomes available! Nicely situated in a prime location just steps to multiple marinas and some of the shoreline's favorite waterfront restaurants, this better-than-new 2-bedroom, 2 full bath, 1-car garage ranch is a standout. Completely rebuilt from the ground up by the current owner, this thoughtfully designed home offers luxurious one-level

  Rose Ciardiello William Raveis Real Estate

  62 Cedar Island Ave, Clinton, CT 06413
• 

  

  /16

  $775,000 Open Sun 1:30PM - 2:30PM

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft

  677 Durham Rd, Madison, CT 06443

  Absolutely pristine and Stunning 3-Bed, 2.5-Bath Home Built in 2022 - Immaculate and Move-In Ready! This exquisite home just had a pristine inspection with no issues. Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home, built in 2022 and designed for modern living. From the moment you step inside, you'll be impressed by the open floor plan that seamlessly blends living, dining,

  Meig Walz Newcomb Coldwell Banker Realty

  677 Durham Rd, Madison, CT 06443
• 

  

  /40

  $799,000 Open Sun 12PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 4,879 Sq Ft

  48 Shepherds Trail, Madison, CT 06443

  Check out the new fresh photos. Contemporary Colonial home features 4 bedrooms, 2.5 baths, and a versatile floor plan designed for both grand entertaining and everyday comfort. Step into the impressive foyer, where an expansive living room and formal dining area set the stage for large gatherings. At the heart of the main level, the kitchen shines with granite countertops, stainless steel

  Erin Connelly Coldwell Banker Realty

  48 Shepherds Trail, Madison, CT 06443
• 

  

  /40

  $875,000

  • 3 Beds
  • 4 Baths
  • 2,235 Sq Ft

  3 Arrowhead Rd, Madison, CT 06443

  Newly Priced! Embrace the enchantment of Shoreline Living at its finest with this sun-drenched haven at 3 Arrowhead, a jewel nestled in a quaint community with the river at your doorstep. As you step into this radiant abode, you're welcomed by a symphony of natural light and the serene melodies of local birdsong. The home's design harmoniously blends the outdoors with the indoors, creating a

  Diana Hartman William Pitt Sotheby's Int'l

  3 Arrowhead Rd, Madison, CT 06443
• 

  

  /40

  $875,000

  • 3 Beds
  • 4 Baths
  • 2,279 Sq Ft

  1054 Boston Post Rd, Guilford, CT 06437

  RARE OPPORTUNITY TO OWN TWO BUILDINGS IN GUILFORD ~ Unlock the potential of this prime commercial property on the bustling Boston Post Road, just one block from Guilford's historic town Green. Within the PV zone (Post Road Village Zone District, this offering includes 2 buildings (see listing #1058 Boston Post Road) that share a driveway and provide dedicated parking; an ideal setup for

  Rose Ciardiello William Raveis Real Estate

  1054 Boston Post Rd, Guilford, CT 06437
• 

  

  /14

  $869,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,625 Sq Ft

  14 Village Cir Unit 14, Guilford, CT 06437

  Introducing the Dalton! 14 Village Circle is located at Guilford's newest luxury community, Village on State. 14 Village Circle is an end unit and construction is well under way! This model features 2,625 square feet of beautiful living space. The main floor is open concept with a large great room and dining room and kitchen, which is perfect for entertaining. On the upper level you will find the

  Vincent Engingro William Raveis Real Estate

  14 Village Cir Unit 14, Guilford, CT 06437
• 

  /2

  $929,000 New Construction

  • 2 Beds
  • 2.5 Baths
  • 2,625 Sq Ft

  28 Village Cir Unit 28, Guilford, CT 06437

  New Development. 25 units. Now under construction, Units over 2200 sqft. Full Basement and 2 car garages.

  Vincent Engingro William Raveis Real Estate

  28 Village Cir Unit 28, Guilford, CT 06437
• 

  

  /31

  $825,000 Pre-Foreclosure

  • 3 Beds
  • 3.5 Baths
  • 3,772 Sq Ft

  13 Longview Terrace, Madison, CT 06443

  Privately sited at the end of Longview Terrace with expansive marsh and river views this larger than most free-standing colonial at over 3700 sf offers luxurious condo living. With a three-story generous layout this unit is south facing and full of light and custom details. The oversized kitchen with breakfast area is open to a 22x17 private deck. The primary suite offers a fireplace, a very

  Margaret Muir William Pitt Sotheby's Int'l

  13 Longview Terrace, Madison, CT 06443
• 

  

  /22

  $177,500

  • 1 Bed
  • 1 Bath
  • 523 Sq Ft

  73 South St, Madison, CT 06443

  Madison-beach property! Dreaming of sunny beach days and enjoying all the shoreline lifestyle offers? Then this one is for you! Fully turnkey renovated seasonal cottage directly bordering Hammonasset Beach State Park. Enjoy the park's two miles of sandy beaches, secluded coves, picnic areas, wildlife sanctuary and 936 acres of protected waterfront lands all easily accessible from your quaint

  Rick Loranger Coldwell Banker Realty

  73 South St, Madison, CT 06443
• 

  

  /40

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  79 Fall Rd, Guilford, CT 06437

  Lakefront Living at Its Best - Just in Time for the Holidays! Welcome to this beautifully maintained 3-bedroom, 2-bath home in the sought-after Guilford Lakes neighborhood, where every season shines-and the magic of the holidays is just around the corner. Offering over 2,100 square feet of living space, this residence blends comfort, character, and an unbeatable lakefront setting with tranquil

  Jules Gaughran - Etes William Pitt Sotheby's Int'l

  79 Fall Rd, Guilford, CT 06437
• 

  

  /9

  $385,000

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft

  20C Yankee Glen Rd Unit 20C, Madison, CT 06443

  20 Yankee Glen, Madison, Connecticut - Tucked just minutes from the sandy shoreline of Hammonasset Beach State Park, this single-standing condominium combines the serenity of coastal living with the charm of New England design. Behind its private entryway lies a sun-filled home where tall ceilings, a beautiful wood-burning fireplace, and a seamless flow between the living and dining spaces create

  Dallas Davis Dalvis Realty

  20C Yankee Glen Rd Unit 20C, Madison, CT 06443
• 

  

  /35

  $749,500

  • 4 Beds
  • 2.5 Baths
  • 3,212 Sq Ft

  174 Concord Dr, Madison, CT 06443

  Step into this exquisitely renovated colonial-style residence, where classic charm seamlessly blends with contemporary sophistication. Gleaming hardwood floors flow throughout the main living spaces, reflecting natural light and enhancing the home's warm ambiance. The heart of the home is a stunning chef's kitchen, thoughtfully designed with state-of-the-art appliances, quartz countertops, and

  Terence Dominick Complete Real Estate

  174 Concord Dr, Madison, CT 06443
• 

  

  /30

  $690,000

  • 4 Beds
  • 2.5 Baths
  • 3,057 Sq Ft

  39 Stepping Stone Ln, Madison, CT 06443

  Classic Madison Colonial with Pool, Privacy and Expansion Potential Set back from the road at the end of a small cul-de-sac, this inviting 3-bedroom, 2.5-bath Colonial offers privacy, space, and flexible living options. Originally a 4-bedroom home, it can easily be converted back since the fourth bedroom was transformed into a large dressing room connected to the primary bedroom. The two

  Cindy Breckheimer Forever Homes Real Estate LLC

  39 Stepping Stone Ln, Madison, CT 06443
• 

  

  /18

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,138 Sq Ft

  20 Strawberry Hill Rd, Madison, CT 06443

  This original owner, 1960's built, 3 bedroom, 2 bath single family residence is nestled in an established, sought-after area and offers unlimited possibilities. Whether you are a first-time homebuyer, investor or renovation enthusiast, this property is your chance to customize a home that reflects your vision and style in a location that truly delivers. Bring your vision and unlock the

  Pam Kadamus William Pitt Sotheby's Int'l

  20 Strawberry Hill Rd, Madison, CT 06443
• 

  

  /31

  $465,000

  • 3 Beds
  • 2 Baths
  • 1,975 Sq Ft

  18 Deepwood Dr, Madison, CT 06443

  Charming 3-Bedroom Split-Level Home in a Quiet, Established Neighborhood Welcome to your new home! This lovingly maintained split-level residence combines comfort, style, and functionality-perfect for those seeking a peaceful retreat. This home features 3 bedrooms, 2 full bathrooms, and a warm, inviting living area. Step into a bright living room filled with natural light from a large front

  Alison Shaheen Sand Harbor Real Estate LLC

  18 Deepwood Dr, Madison, CT 06443
• 

  

  /16

  $455,000

  • 3 Beds
  • 2 Baths
  • 1,419 Sq Ft

  75 Fairview Dr, Madison, CT 06443

  3 bedroom 2 full baths close to town private road, close to Bower Park, 2 car garage attached. Totally renovated, Hardwood floors and wood composite laminate's where not oak, bow and bay Anderson windows, a must see!

  Derek Eisenberg Continental Real Estate

  75 Fairview Dr, Madison, CT 06443
• 

  

  /40

  $485,000

  • 5 Beds
  • 3 Baths
  • 2,652 Sq Ft

  76 Squires Rd, Madison, CT 06443

  Come see this charming Ranch oasis in desirable Madison, where the allure of suburban tranquility meets the vibrancy of community living! Nestled in a private setting yet so close to all amenities, this 5-bedroom, 3-bath home is a rare find that offers an unparalleled lifestyle. Step inside and be greeted by a spacious living room with french doors leading out to the expansive deck, where you can

  Joseph Giordano RE/MAX Alliance

  76 Squires Rd, Madison, CT 06443
• 

  

  /40

  $3,795,000

  • 4 Beds
  • 5 Baths
  • 4,505 Sq Ft

  98 Island Ave, Madison, CT 06443

  Welcome to 98 Island Avenue in Madison, a stunning coastal residence just a short walk to the beach and town. Custom built in 2016 w/extraordinary attention to detail, this home combines timeless elegance with modern convenience. Inside, you'll find soaring 9-foot ceilings, 8-foot doors, hurricane-rated Andersen windows, & polished nickel Baldwin hardware throughout. The chef's kitchen is a

  Susan Clifford Coldwell Banker Realty

  98 Island Ave, Madison, CT 06443
• 

  

  /40

  $549,900

  • 3 Beds
  • 2.5 Baths
  • 1,944 Sq Ft

  36 Silver Birch Ln, Clinton, CT 06413

  Privately set on over 2.5 acres with mature landscaping, this home offers comfort and convenience. The family room features a cathedral ceiling and fireplace, while the eat-in kitchen flows into an open floor plan with skylights and access to a large deck overlooking the private backyard. The primary suite includes a private bath and walk-in closet. Additional highlights include central air,

  Craig Milton Re/Max Valley Shore

  36 Silver Birch Ln, Clinton, CT 06413
• 

  

  /37

  $2,400,000

  • 4 Beds
  • 2 Baths
  • 3,083 Sq Ft

  153 Middle Beach Rd, Madison, CT 06443

  Charming beach home with full guest apartment above garage across the street from Long Island Sound. Perfect opportunity for personal use, 1031 exchange or investment property. Main house and guest apartment both enjoy decks that overlook beautiful marshes with abundant wildlife. Main house has views of Long Island Sound from the second floor. Guest apartment embraces a full kitchen, family room

  John Campbell Compass Connecticut, LLC

  153 Middle Beach Rd, Madison, CT 06443

Showing Results 1 - 40, Page 1 of 3