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 property combines timeless elegance with modern amenities. d bedrooms, soaring 10-foot ceilings, and expansive, sun-drenched rooms that invite relaxation and entertaining. This exceptional home offers a gracious layout for both entertaining and everyday living. Built with the finest materials. exceptional millwork, beautiful cabinetry and fixtures A versatile great room perfect for movie nights or cozy gatherings, and an open floor plan that seamlessly connects living, dining, and kitchen areas. Step outside to your own private retreat-professionally landscaped grounds with a blue stone patio and outdoor fireplace create an inviting atmosphere for year-round entertaining. Dive into the heated and cooled Gunite saltwater pool, unwind in the stylish pool house complete with a bath and outdoor shower, and experience the ultimate in luxury living. This meticulously crafted home offers the perfect blend of sophistication, comfort, and location. Whether hosting grand gatherings or enjoying peaceful moments at home, 37 Lantern Hill Road is more than a residence-it's a lifestyle.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Catharina "Cathy" Lynch
$2,650,000
N/A Area Single Family Home
Active
75 Half Mile Road Guilford, CT 06437
5 Bed
8 Baths
8476 sqft
MLS# 24076393
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 first-floor guest suite enjoys its own private wing, while the finished lower level includes a theater room and recreation area. The outdoor spaces are equally impressive. The meticulously landscaped grounds feature mature plantings, a bluestone patio, an outdoor fireplace complete with pizza oven, a heated gunite pool, and a tennis court with lines for both tennis and pickleball. A separate carriage house provides a garage bay, office space, an additional bedroom, and a full bath, perfect for guests or as a home office. Additionally, a whole home generator. Ideally located just minutes from the town center and its historic green, this property offers access to boutique shops, a variety of restaurants, cozy coffee shops, and the scenic Jacob's Beach. This one-of-a-kind home is truly exceptional, with so much more to discover and appreciate. Set privately back from the road, please do not drive up to the property without an appointment.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Catharina "Cathy" Lynch
$1,995,000
N/A Area Single Family Home
Active
30 Meeting House Lane Madison, CT 06443
5 Bed
4 Baths
3912 sqft
MLS# 24097336
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 shares architectural harmony through its grand columns and elegant two-story shutters. The architect, Mr. Volney Pierce, was commissioned to design this exceptional residence and later the Congregational Church. Inside, the home offers more than 3,900 square feet of living space with soaring 9+ foot ceilings on the main level, 2nd floor with five generously sized bedrooms, five working fireplaces, and the 3rd floor a uniquely large attic with unlimited possibilities. At the back of the property are the outbuildings, a 3 car garage and small coop/shed. "Hartsbourne", has abundant historic character throughout. Set on 1.5+ acres in the heart of Madison's charming village, this is a rare opportunity to own a true piece of local history.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Catharina "Cathy" Lynch
$1,899,000
N/A Area Single Family Home
Active
584 Boston Post Road Madison, CT 06443
5 Bed
6 Baths
4790 sqft
MLS# 24111933
Elegant European-Style home in the Heart of Madison. A perfect blend of luxury, privacy, and convenience in this remarkable home, ideally located just steps from the Madison Town Green, downtown shops, and stunning beaches. This five-bedroom home offers a host of exceptional features. Step through the front door into a dramatic two-story great room with an open floor plan, bathed in natural light. The newly updated kitchen, fresh and inviting, seamlessly connects to the great room, creating the perfect hub for gatherings. Recently painted and featuring stunning white maple floors. Each of the five spacious bedrooms boasts its own private bath. The home's luxurious amenities include a breathtaking Gunite in-ground pool and hot tub. Enclosed for year-round use, the pool area transforms effortlessly for the summer months with doors that open onto a grand stone patio. The left wing of the house features a beautifully remodeled one-bedroom apartment, ideal for in-laws, an Au pair, guests or a rental income. Work from home in style with a newly renovated study and office space, complete with custom cabinetry and a handsome gas fireplace. Outdoors, the private backyard is a true sanctuary, featuring a spacious stone patio, wood-burning fireplace, and a built-in pizza oven-perfect for entertaining family and friends. The lower level adds over 1,000 sq ft of bonus living space, including a newly remodeled media room, play area, and a fully equipped gym.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Kate Jasko
$1,899,000
N/A Area Multi-Family Home
Active
584 Boston Post Road Madison, CT 06443
5 Bed
6 Baths
4790 sqft
MLS# 24108154
Elegant European-Style home in the Heart of Madison. A remarkable home ideally located just steps from the Madison Town Green, downtown shops, and stunning beaches. This five-bedroom home offers a host of exceptional features including a newly remodeled in-law/accessory apartment with its own private entrance, a gorgeous kitchen, living room, dining area, 2 full baths, and washer and dryer. Step through the front door of the main house into a dramatic two-story great room with an open floor plan. The newly updated kitchen, fresh and inviting, seamlessly connects to the great room, creating the perfect hub for gatherings. Each of the five spacious bedrooms boasts its own private bath. The home's luxurious amenities include a breathtaking Gunite in-ground pool and hot tub. Enclosed for year-round use, the pool area transforms effortlessly for the summer months with doors that open onto a grand stone patio. Work from home in style with a newly renovated study and office space, complete with custom cabinetry and a handsome gas fireplace. Outdoors, the private backyard features a spacious stone patio, wood-burning fireplace, and a built-in pizza. The lower level adds over 1,000 sq ft of bonus living space, including a newly remodeled media room, play area, and a fully equipped gym. Whether you're seeking a multi-generational home or live in one unit and rent the other or enjoy the entire home yourself-the options are endless.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Kate Jasko
$979,000
Chapman Beach Area Multi-Family Home
Active
94 Waldron Drive Westbrook, CT 06498
6 Bed
6 Baths
4940 sqft
MLS# 24111210
Coastal Duplex in Chapman Beach Association. Set on nearly half an acre in the desirable Chapman Beach Association, this unique and spacious duplex blends coastal charm with modern comfort. Each unit offers 3 bedrooms, 3 baths, an attached garage, and an expansive deck for relaxing or entertaining. The main level includes a bedroom, full bath, and a kitchen with stainless steel appliances that opens to the dining area and deck. Upstairs, the primary suite impresses with vaulted ceilings, a walk-in closet, and a loft perfect for a home office or gym. The luxurious ensuite bath features heated tile floors, a dual vanity, private water closet, and a rainfall shower. Each unit has nicely sized rooms and plenty of closet space. Live in one unit and rent the other, host extended family or enjoy the entire home yourself. Embrace year-round coastal living and private beach access in the sought-after Chapman Beach community. Also listed as a single family 24111212
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Catharina "Cathy" Lynch
$770,000
N/A Area Single Family Home
Active
57 Laurel Ridge Trail Killingworth, CT 06419
4 Bed
3 Baths
3225 sqft
MLS# 24112557
This move-in ready farmhouse Colonial, complete with a charming wrap-around porch, offers over 3,200 sf of thoughtfully designed living space on a private 2.6-acre wooded lot. Filled with an abundance of natural light, the main level features 9-foot ceilings, formal living & dining rooms, and a spacious, well-appointed kitchen with granite countertops, a large center island, stainless steel appliances, and custom cabinetry. The kitchen opens to a bright and inviting family room with a thermostatically controlled pellet stove fireplace and sliders that lead to an oversized deck-ideal for seamless indoor-outdoor entertaining. Upstairs, the primary suite includes a walk-in closet and full bath with double vanity, jetted tub, and separate glass-enclosed shower. Three additional bedrooms and a large bonus room over the two-car garage provide ample flexible living space to suit a variety of needs. Recent upgrades include newer windows, central air and propane heating system, tankless water heater and a whole-house generator for added comfort and peace of mind. Additional highlights include hardwood floors throughout, a full walk-up attic and walk-out basement-both offering excellent potential for future expansion. Ideally located just a few miles from I-95, this property provides easy access to New Haven, Hartford, and is within 2 hours of New York City and Boston-making it a perfect year-round residence or weekend retreat in the heart of New England.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Dana Weinstein
$625,000
N/A Area Townhouse
Active
67 Boston Post Road 8 Madison, CT 06443
2 Bed
3 Baths
1816 sqft
MLS# 24096458
Welcome to this elegant 2-bedroom townhouse-style condominium located in the nearly new East River Farms community. This development offers a classic New England aesthetic, complete with a picturesque stone wall & professionally landscaped grounds. Step inside to find a beautifully designed open floor plan featuring pristine hardwood floors, soaring 9-foot ceilings with triple crown moldings, & a cozy gas fireplace that creates a warm, inviting atmosphere. The chef-inspired kitchen is a true highlight, featuring an 8-foot granite island with seating for 4, a porcelain Shaw's farm sink, subway tile backsplash, premium WOLF cabinetry, and top-of-the-line appliances including a Samsung stainless-steel refrigerator, built-in microwave, and Frigidaire gas range with hood. There is direct access from the kitchen to a blue stone patio, a perfect spot for an outdoor grill/seating. The main level also offers a stylish half bath and two roomy closets. Upstairs, the primary suite features a spacious walk-in closet and a luxurious en-suite bathroom with double granite sinks. A recently converted loft now serves as a legal second bedroom, complete with its own full bathroom featuring a tiled shower. For added convenience, the second-floor laundry includes a Samsung washer & dryer and plenty of shelving. The home offers generous closet space throughout, plus additional storage in the crawl space. Freshly painted interiors make this home truly move-in ready.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Dana Weinstein
$580,000
N/A Area Townhouse
Pending
73 Legend Hill Road 73 Madison, CT 06443
2 Bed
3 Baths
1836 sqft
MLS# 24102683
Welcome to this beautifully maintained two-bedroom, 2.1-bath townhouse condominium in Madison's sought-after Legend Hill community. Set within an 88-acre private enclave of 90 homes, Legend Hill is rich in history and charm, with residences thoughtfully arranged around the historic Northam Manor. Perched on one of the highest elevations between Boston and the New York shoreline, the community offers sweeping views, serene privacy, and upscale amenities-including a tennis/pickleball court, gunite pool, and a clubhouse housed in the original cobblestone mansion. This particular home is ideally positioned to capture abundant light, enhanced privacy, and distant views of Long Island Sound. Inside, the first floor features a spacious living room with built-ins and a fireplace, a formal dining room, and a bright eat-in kitchen. The primary suite has two walk-in closets and a full bathroom with a soaking tub and separate shower. A second bedroom offers its own en-suite bath and a generous closet. The walk-out lower level includes sunny, flexible space perfect for an office or family room, plus ample unfinished storage space. A two-car garage provides direct, weather-protected access to the kitchen-making daily living as convenient as it is comfortable.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Dana Weinstein
$580,000
N/A Area Single Family Home
Active
40 Puritan Lane Madison, CT 06443
4 Bed
4 Baths
2032 sqft
MLS# 24111934
Spacious and thoughtfully expanded, this one-owner split-level home offers 4 bedrooms and 3.1 bathrooms and is ideally located just 1.5 miles from downtown Madison. Over the years, the home has been enhanced to create a desirable open floor plan, featuring a sun-filled great room with cathedral ceilings, a fireplace and screened porch at the rear of the home-perfect for everyday living and entertaining. The kitchen has beautiful wood cabinetry with a tile backsplash and stainless appliances. The main level also includes a private primary suite addition, providing comfort and convenience. Upstairs, you'll find three additional bedrooms and two full bathrooms, while the lower level offers a cozy family room, half bathroom and a practical mudroom entry with access to the 2 car garage. This home is connected to public water and offers a whole house generator for added peace of mind. It is conveyed as is.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Dana Weinstein
$515,000
N/A Area Condo
Active
40 Legend Hill Road 40 Madison, CT 06443
2 Bed
3 Baths
1160 sqft
MLS# 24112460
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 the living room/ dining room with inviting fireplace. Off the living room is a bright and sunny sunroom. All on one level living. The main level includes a comfortable primary suite with a private bath, a second bedroom, and a full hall bathroom. The finished lower-level impresses with a large flexible space-ideal for a media room, playroom, or home gym-plus a convenient half bath and walk-out access to a private outdoor area. Enjoy easy, maintenance-free living in one of Madison's most sought-after communities. Just move in and start enjoying the best of the shoreline lifestyle.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Catharina "Cathy" Lynch
$25,000 / mo
Sachems Head Area Rental Home
Active
55 Vineyard Place Guilford, CT 06437
4 Bed
3 Baths
3925 sqft
MLS# 24104615
AUGUST RENTAL. DIRECT WATERFRONT home in beautiful Sachem Head/Vineyard Point community. Enjoy gorgeous views, a private sandy beach out your backdoor and access to tennis court right next door. Walls of glass with views of Long Island Sound from every room. An open floor plan includes a large living room with stone fireplace and dining room. A family room is also on the main floor equipped with Large TV, and spectacular views as well. The eat-in kitchen includes a center island, double refrigerators, fireplace, dining area and glass doors lead out to stone patio for barbeques or to just take in the view. One of the 2 full baths is on the first floor. There are 4 bedrooms upstairs with an additional room that can be used for an in-home office space and/or TV room. All bedrooms on the 2nd floor share one Full bath with shower and a hall half bath. Maximum of 6 ppl at the house. Convenient to Metro North train, Guilford's charming village and downtown New Haven. 2 hours to NYC and Boston. Newly decorated and equipped with everything you need to enjoy your stay. Home is available for the month of August 2025.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Kate Jasko
$7,000 / mo
Sachems Head Area Rental Home
Active
55 Vineyard Place Guilford, CT 06437
4 Bed
3 Baths
3925 sqft
MLS# 24105724
ACADEMIC RENTAL SEPT 2025 - MAY 2026. DIRECT WATERFRONT home in beautiful Sachem Head/Vineyard Point community. Enjoy gorgeous views, a private sandy beach out your backdoor and access to tennis court right next door. Walls of glass with views of Long Island Sound from every room. An open floor plan includes a large living room with stone fireplace and dining room. A family room is also on the main floor equipped with Large TV, and spectacular views as well. The eat-in kitchen includes a center island, double refrigerators, fireplace, dining area and glass doors lead out to stone patio for barbeques or to just take in the view. One of the 2 full baths is on the first floor. There are 4 bedrooms upstairs with an additional room that can be used for an in-home office space and/or TV room. All bedrooms on the 2nd floor share one Full bath with shower and a hall half bath. Maximum of 6 ppl can occupy the house. Convenient to Metro North train, Guilford's charming village and downtown New Haven. 2 hours to NYC and Boston. Newly decorated and equipped with everything you need to enjoy your stay.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Kate Jasko
$4,500 / mo
N/A Area Rental Home
Active
37 Bassett Lane Madison, CT 06443
3 Bed
2 Baths
1944 sqft
MLS# 24106229
*****Available August 10, 2025 for the academic year at $4,500 per Month plus utilities. Beautifully furnished rental with deeded beach rights. This home was completely remodeled in 2020. The 1st floor features open concept living, with the bright kitchen as the focal point in the center. From the dining area, sliders lead to a custom-built patio for easy inside-outside entertaining at the private backside of the home. Also on the 1st floor is a living room graced by a gas fireplace, the master suite, and mudroom/laundry room. On the 2nd floor are 2 big bedrooms and another spacious full bath. Outside, not only is there a 2-car detached garage on this double-sized and level lot, there's a yard big enough for ball games and picnics all summer long! With the private beach just a short stroll down the lane, you'll be the place everyone wants to be this summer. Two months security, credit check and references required. Cleaning fee of $300.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Catharina "Cathy" Lynch
$4,000 / mo
N/A Area Rental Home
Active
90 Boston Post Road Madison, CT 06443
3 Bed
2 Baths
2034 sqft
MLS# 24104350
Charming Downtown Madison Rental. Enjoy gorgeous salt marsh views from this lovely 3-bedroom home available for a yearly lease starting this September. The main level offers two spacious bedrooms with a shared full bath, while the private upstairs primary suite features vaulted ceilings, a gas fireplace, full bath, and a balcony with sweeping marsh views. A sunny living room opens to the deck and overlooks the marsh. The vaulted dining room with a gas fireplace is ideal for gatherings, and kitchen boasts granite countertops, a breakfast bar, with appliances including a gas cooktop and double ovens. Conveniently close to town, beaches, and highways-experience the best of Madison living.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Kate Jasko