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50 Overbrook Rd, Madison
$930,000
3 Beds ⋅ 4 Baths ⋅ 24168571 MLS
Welcome to a beautiful Cape Cod-Contemporary retreat that perfectly blends modern updates with a comfortable, inviting atmosphere. The heart of this home is the stunning chef's kitchen, featuring a large center island with seating for 4, professional gas cooking, high-end appliances, and an incredible amount of pantry and storage space. It flows naturally into the dining room, where a cozy gas fireplace makes the space perfect for hosting everything from holiday dinners to casual weeknight meals. Relax in the living room or head to the family room to enjoy a second gas fireplace and walls of windows that bring the beauty of the private backyard inside. Walk in from your 2 car garage to a mudroom space complete with half bath and dedicated laundry room. The floor plan is designed for easy living, highlighted by a main-level primary suite complete with two walk-in closets with great organization systems and a spacious bathroom featuring double sinks and a beautifully tiled shower. Upstairs, you'll find two oversized bedrooms, both with their own walk-in closets, and a full guest bath. The finished lower level offers additional living space with a bonus room, private office and half bath. There is an abundance of storage in the lower level and throughout the home. Outside, the large AZEK deck leads to a heated in-ground pool, creating a private summer oasis.

50 Overbrook Rd, Madison

111 Acorn Rd, Madison
$920,000
3 Beds ⋅ 3 Baths ⋅ 24173956 MLS
This impeccably maintained Colonial blends timeless charm with modern sophistication, ideally situated in a desirable family neighborhood on a quiet street just minutes from downtown Madison, scenic walking trails, beaches, and the train station. Nestled on a private lot with a serene backyard setting, the home offers exceptional comfort, style, and everyday livability. The centerpiece of the home is the beautifully redesigned oversized kitchen, featuring custom top-of-the-line cabinetry, convenient pull-out drawers, two spacious pantries, premium appliances, and a GE Monogram beverage fridge. Thoughtfully designed for both functionality and entertaining, the kitchen seamlessly combines elegance and practicality. Spacious, sun-filled living areas create a warm and inviting atmosphere, highlighted by a fireplace with a wood insert for added charm and efficiency. A dedicated home office features an oversized L-shaped desk and abundant custom built-in cabinetry, providing exceptional workspace and storage. Gas heat and central air provide year-round comfort, and this is one of the few homes in Madison offering both public water (no well) and natural gas from the street. Recent improvements, including a new roof and all replacement windows, offer peace of mind while enhancing the home's pristine condition. Perfect for both entertaining and relaxed daily living, this exceptional property offers the rare combination of privacy, convenience, and refined design.

111 Acorn Rd, Madison

10 Isabell Dr, Madison
$915,000
3 Beds ⋅ 4 Baths ⋅ 24179028 MLS
Built in 2001, this expansive Custom Cape with its charming front covered porch offers a one-of-a-kind setting in North Madison, ideally located at the end of a cul-de-sac on 2.64 acres and surrounded by open space. The square footage is deceptive with 3536 sf (this DOES NOT include the 3-season room +452 sf) plus the huge basement offering another 1880 sf. Designed with intention and exceptional scale, the smart design of the main floor begins with the location of laundry and mudroom between the garage and kitchen, keeping you organized and your house clean. From there, the focus is the spectacular great room and kitchen, working together for both the day-to-day and for lively gatherings. The eat-in kitchen offers multiple prep zones, island with breakfast bar, generous cabinet space & pantry, granite counters, and stainless appliances (wall oven, microwave and cooktop are NEW). The vaulted great room anchors the main level with its soaring granite fireplace, wall of windows, and seamless access to the enormous 3-season room and backyard. The large 2-story foyer leads to both the formal dining room with wainscoting and the classic study / home office. Also located on the main floor, the large primary suite will delight with its walk-in closet, large en-suite, and private access to the porch and backyard. The rare second floor layout offers two expanded bedroom or guest suites, each featuring sitting/play/study rooms, and privately located on opposite ends of the catwalk

10 Isabell Dr, Madison

706 Green Hill Rd, Madison
$900,000
4 Beds ⋅ 4 Baths ⋅ 24188945 MLS
Situated on over an acre of manicured grounds, this custom-built Colonial blends traditional charm and modern convenience. An inviting front porch welcomes you into a thoughtfully designed floor plan. The main floor flows effortlessly from each room to the next. The eat-in kitchen features an island and sliders to a rear deck. A see-through wood-burning fireplace creates a focal point between the kitchen and formal dining room, while the living room offers a propane fireplace. A full bath and main floor laundry add everyday convenience. The upper level features a primary suite with a walk-in closet - finished with a full bathroom including a jetted tub, a shower and toilet room. An additional generously sized bedroom includes a walk-in closet with access to a full bathroom. Completing the upper level are two more bedrooms, providing plenty of space. The lower level expands the living space with over 1,000 square feet of finished recreation area and bathroom, with walk-out access and stairs leading directly to the three-car garage. Above the garage, a lofted area ensures ample storage. With a newer roof, fresh carpeting, and a newly resurfaced rear deck overlooking the beautiful yard, this maintained home is move-in ready.

706 Green Hill Rd, Madison

11 Soundview Ave, Madison
$900,000
2 Beds ⋅ 1 Baths ⋅ 24179125 MLS
Welcome to your own slice of the Connecticut shoreline. Ideally situated in a sought-after Madison beach community, this coastal retreat offers the shoreline lifestyle so many dream about. Enjoy a short stroll to the beach, water views, and the relaxed rhythm of coastal living. Set on a private road in a highly desirable neighborhood, the property enjoys Long Island Sound views in one direction and East River salt marsh views in the other, offering the best of Connecticut's shoreline and coastal wetlands in one exceptional setting. Inside, the home offers comfortable year-round living with a cozy fireplace, light-filled living spaces, an enclosed porch, and inviting areas for gathering with family and friends. The detached studio, complete with split-system heat and A/C, provides flexibility as a home office, art studio, fitness space, or guest retreat. The standout feature is the exceptionally private backyard oasis. Thoughtfully landscaped and meticulously maintained, it features expansive paver patios, a hot tub, a retractable electric awning, and multiple outdoor living spaces designed for relaxation and entertaining. Additional highlights include 200-amp electrical service, a backup power switch, a three-bedroom, two-bath septic system, two storage sheds, and ample attic space. This property offers a rare combination of privacy, water views, beach access, and coastal charm just minutes from downtown Madison.

11 Soundview Ave, Madison

114 Rolling Meadow Rd, Madison
$875,000
5 Beds ⋅ 4 Baths ⋅ 24163044 MLS
Beautiful 5 bedroom, 3.5 bath Colonial set in a highly desirable neighborhood just minutes from town, schools, and the beach. Situated on a level, 1+ acre lot, this home offers an expansive backyard ideal for outdoor entertaining and everyday fun. Hardwood floors run throughout the home, enhancing its classic appeal. The spacious kitchen is thoughtfully designed and features a SubZero refrigerator, Dacor double wall ovens, granite countertops, a large island, a built-in desk and a wet-bar with a wine chiller. Sliders lead to the patio. The everyday dining area is perfect for casual meals and gatherings. The first floor offers an excellent layout with a large family room, dining room, and a living room with a fireplace. An additional room off the living room provides flexible space for a home office or playroom. Upstairs, you'll find 5 generously sized bedrooms and 3 full baths. The expansive primary suite features a private balcony overlooking the backyard, along with a spacious full bath complete with a double vanity, whirlpool tub, & separate shower. The remaining bedrooms offer ample closet space and access to two additional full bathrooms. The 2nd floor also includes 2 large walk-in closets, amazing storage! There is an unfinished basement and an attic with pulldown stairs for more storage. With over 3,500 square feet of living space, this home comfortably accommodates today's lifestyle. Selling in "As-Is" condition. Prefer a closing after 6/18/2026.

114 Rolling Meadow Rd, Madison

25 Knob Hill Rd, Madison
$865,000
4 Beds ⋅ 3 Baths ⋅ 24194353 MLS
Incredible opportunity to own this classic four-bedroom Colonial in the highly sought-after Knob Hill neighborhood. Nestled on a lovely, quiet street just minutes from town and the beaches, this home is beautifully set back from the road, offering both privacy and curb appeal. The kitchen with vaulted ceilings opens to the family room and a stunning screened porch, creating the perfect flow for everyday living and entertaining. A full bath next to the office/guest room on the main level adds convenience and flexibility. Upstairs, you'll find four generously sized bedrooms, including a primary suite with its own private bath. The vaulted screened porch is a true highlight - an ideal place to relax and enjoy the peaceful surroundings. Step outside to a brick patio overlooking the private backyard, perfect for outdoor gatherings or quiet evenings. The finished lower level provides additional living space for recreation, a playroom, home gym, or office, along with a second fireplace and ample storage. Additional features include a brand new roof, recently painted exterior, city water, central air conditioning, potting shed, and a two-car garage. Knob hill is a one of a kind neighborhood, holiday get togethers, 4th of July bike parade and safe walking and biking. Located just north of the Boston Post Rd.

25 Knob Hill Rd, Madison

51 Country Way, Madison
$850,000
4 Beds ⋅ 3 Baths ⋅ 24183386 MLS
Tucked away in a serene, private setting surrounded by scenic trails and protected conservation land, this exceptional home showcases a sophisticated designer aesthetic, where timeless New England character meets thoughtfully curated modern living. Classic stone walls, refined finishes, and beautifully appointed spaces create a residence that feels both elegant and effortlessly welcoming. At the heart of the home is a stunning custom kitchen, designed for both everyday living and effortless entertaining. A showstopper 12-foot quartz island with abundant seating anchors the space, two sinks, custom built-in pantries, and elegant Juliska pendant lighting. Designer finishes continue throughout the home, including beautifully appointed bathrooms featuring custom marble tile and counters, and curated designer lighting. Generously proportioned bedrooms provide both comfort and versatility. One standout space features soaring cathedral ceilings, skylights, built-in desks and shelving, and oversized closets with custom storage cubbies. A sun-filled four-season room currently serves as a home office and sitting area, offering flexibility as a formal dining room, library, or additional living space. Outdoor living is equally impressive. A sprawling custom-built deck creates the perfect backdrop for entertaining, complete with an outdoor television and gathering space. Steps lead to a private fire pit area and beautifully maintained grounds, where nature and privacy take center stage.

51 Country Way, Madison

104 Scotland Rd, Madison
$850,000
5 Beds ⋅ 2 Baths ⋅ 24161452 MLS
Set on what is arguably the most beautiful lot in downtown Madison. This enchanting 5-bedroom farmhouse perfectly blends timeless charm with modern convenience. The nearly one-acre, meticulously manicured property makes a lasting impression. Complete with majestic stone walls & a stunning brick patio. Inside, the home welcomes you with a thoughtfully designed mudroom, creating a private and practical entry point. The oversized family room is filled with natural light and anchored by a cozy wood stove, offering a warm and inviting atmosphere. The fully remodeled eat-in kitchen is truly the heart of the home, featuring abundant storage & spacious dining room, & a seamless flow into a versatile living room that can also serve as a formal dining space. A bright first-floor office with a skylight provides flexibility and can easily function as a guest bedroom, conveniently located near a full bath. Upstairs, you'll find five charming bedrooms with built-ins, generous closet space, and a beautifully updated full bathroom. The primary bedroom stands out with its high ceilings & airy feel, while the entire second floor is bathed in sunlight. Additional highlights include newer gas heating, central air, city water, a two-car garage and an updated roof. All of this and is just a short walk to downtown Madison's shops, beach, restaurants, train station, and movie theater. This is a rare opportunity to own a truly special home in an unbeatable location.

104 Scotland Rd, Madison

36 Devonshire Ln, Madison
$845,000
4 Beds ⋅ 3 Baths ⋅ 24188850 MLS
Welcome to this exquisite 4-bedroom, 2.5-bath colonial home, where classic design meets modern luxury. This property offers an ideal combination of space, style, and comfort. Enter an inviting entryway into a spacious foyer with beautiful hardwood floors, that flow throughout the main level. The formal living room with large windows and French doors allows for natural light, while the formal dining room is perfect for hosting dinner special occasions. The exceptional kitchen that boasts Cambria Quartz countertops, high-end stainless-steel appliances, custom cabinetry, and a large center island with seating. in addition, there is a bright and airy breakfast, lunch, dinner nook, that offers a lovely spot for dining or just drinking coffee, while overlooking the gardens. The main family room is perfect for relaxation and entertainment, featuring a fireplace, adding warmth and atmosphere. On the upper level there is a spacious master bedroom includes a walk-in closet and an en-suite bathroom with dual vanity sinks, a soaking tub, and a separate shower, providing a private retreat. Three additional generously sized bedrooms, that share a well-appointed bathroom, and offers ample space for family, guests, or a home office.

36 Devonshire Ln, Madison

40 Hull Rd, Madison
$825,000
4 Beds ⋅ 3 Baths ⋅ 24153355 MLS
Seldom-available offering in one of Madison's premier neighborhoods. This versatile split-level home sits on a double lot spanning over 2 acres, offering exceptional privacy and room to grow. Set back from the street with a circular driveway, the property unfolds to reveal 4+ bedrooms, 3 full baths, and flexible living spaces designed for how you live today. The kitchen, which is the heart of the home, features a brand new Viking 5-burner cook top, Sub-Zero refrigerator, large center island, and tons of counter space and storage-perfect for home chefs and entertaining. Step outside to your private resort: an in-ground pool with newer liner anchors the expansive yard, while an additional detached 1-car garage presents endless possibilities as a pool house, studio, workshop, or guest suite. Recent updates bring modern peace of mind: brand-new septic system (installed prior to closing when weather permits), whole-house water filtration, professional radon mitigation, fresh interior paint, and new carpeting in the lower level. Move in and enjoy, or re-imagine the space to suit your vision. With over 2 acres in a prime Madison location, this property offers a foundation that's increasingly hard to find--space, privacy, flexibility, and solid bones with key systems already updated. Whether you're looking for a family compound or a private retreat minutes from town, this is your canvas. Madison living with room to breathe.

40 Hull Rd, Madison

49 Hammonassett Meadows Rd, Madison
$819,000
4 Beds ⋅ 3 Baths ⋅ 24182360 MLS
LOCATION, LOCATION...This 4BR, 2.5 Bath home is in absolutely pristine condition. Meticulously maintained by the original owner, this home has been loved and cared for and it really shows! Located in the very desirable neighborhood, Hammonassett Meadows, and situated on a 1.45 acre lot. The home features upgraded Pella replacement windows, beautiful hardwood floors throughout, newer A/C spit system on the 1st floor, and a beautiful light and bright year round sunroom with electric heat. The sunroom has sliders to a spacious deck overlooking beautiful gardens in the private backyard. The kitchen includes updated stainless steel appliances and an eating space for everyday meals. The kitchen opens to the generous size Family Room. The spacious Living Room has a wood burning fireplace and is a great room for large gatherings. There is a well-proportioned formal dining room for holiday and special occasions too. Upstairs are 4 bedrooms. The Primary Bedroom includes a full bathroom and has 2 closets. There is a full bathroom for the other bedrooms to share. An unfinished basement offers the opportunity to finish it if more space is needed. Location is everything when purchasing a home and 49 Hammonassett Meadows is hard to beat! This home is located in the brand new Neck River Elementary School district too. Schedule an appointment, this home will sell fast!

49 Hammonassett Meadows Rd, Madison

23 Aylesbury Cir Unit 23, Madison
$815,000
2 Beds ⋅ 3 Baths ⋅ 24182415 MLS ⋅ Windermere West BLDG.
Rare opportunity to own an exceptionally beautiful, turnkey Windermere home overlooking the salt marshes of the Hammonasset River. The 2 BR, 3 bath residence is fully remodeled and upgraded and includes an expansive wrap around stone patio with built-in fire table & entertaining areas. The outside space creates a full outside living room! Views of the marshes are ever-changing from dawn until dusk and from season to season. The property boasts a level back yard that allows an expansive view year-round. Totally fresh, this is the ideal sought-after 2 level floor plan in the Windermere community. Light filled spaces flow into each other on the entry floor & include a living room with fireplace & custom floor to ceiling cabinetry. The updated kitchen offers a large breakfast bar & sitting area adjacent to the dining room. The sunporch features a textured board & batten ceiling and sliding glass doors that lead to the stone patio. The 1st floor is rounded out by 2 bedrooms and 2 fully customized bathrooms. The lower level of the residence includes a sizeable family room/den, full bath, a home gym with infrared sauna, a private office, a laundry room and an organized storage room. This home has been fully updated with new impact windows, HVAC system, electrical system and plumbing throughout. The elegant landscaping has been refreshed and expanded. The detached garage also offers built-in storage and an EV charging dock. This property is a gem!

23 Aylesbury Cir Unit 23, Madison

258 Opening Hill Rd, Madison
$805,500
4 Beds ⋅ 3 Baths ⋅ 24168199 MLS
Beautifully renovated 4 bedroom, 2.5 bath Colonial set on 1.28 private acres in the highly desirable Madison community. The main level of this home offers two spacious and versatile living areas, a formal dining room, an open-concept kitchen with granite countertops and stainless steel appliances, plus a bright four-season sunroom filled with natural light. A convenient half bath completes the first floor. The upper level offers four bedrooms, including a primary suite with a newly renovated ensuite bath, along with three additional bedrooms and a full hall bath. Hardwood floors run throughout the home, complemented by recessed lighting, central air, ceiling fans and freshly painted walls. Additional features include wiring for a whole-house generator, an attached two-car garage, an unfinished basement perfect for in home gym and a peaceful, yet convenient location just minutes from Madison and Guilford town centers. Enjoy outdoor living on the patio or in the expansive yard, perfect for entertaining. Don't let this one slip away.

258 Opening Hill Rd, Madison

60 Bradley Corners Rd, Madison
$805,000
4 Beds ⋅ 3 Baths ⋅ 24176299 MLS
Highest and best offers are due by Tuesday, May 26th at 5:00 PM. Welcome home to 60 Bradley Corners Road, a beautifully updated 4-bedroom, 2.5-bathroom colonial nestled on an expansive 2.83-acre lot in the heart of Madison, Connecticut. This property perfectly blends modern comfort with New England charm. Step inside to discover a classic floor plan featuring a renovated kitchen equipped with white cabinets and quartz counters, along with beautifully updated bathrooms. Other upgrades offer total peace of mind, including an energy-efficient mini-split system for customized climate control (2022) and a newer roof. The main living area leads to a lovely screened-in porch, providing the ultimate spot for morning coffee or evening relaxation. From there, take in views of your private, flat, and park-like backyard-an ideal canvas for outdoor entertaining, gardening, or future expansion. Need extra space? The generous walk-up attic offers incredible storage potential or the opportunity to finish and create a custom home office, playroom, or media center. Located just minutes from Madison's pristine beaches, train, and vibrant downtown, this turnkey gem offers the perfect balance of privacy and convenience.

60 Bradley Corners Rd, Madison

46a Beach Ave, Madison
$800,000
3 Beds ⋅ 2 Baths ⋅ 24158460 MLS
Charming ranch set on a picturesque 0.92-acre property spanning from Beach Avenue to Pleasant View Avenue, with deeded beach access at the end of Beach Avenue. Originally built in the 1940s and thoughtfully renovated and expanded in 2001, this home blends classic character with comfortable living. The primary bedroom features windows that capture lovely views of the surrounding property, along with a generous closet. It shares a full bath with the second bedroom. The third bedroom, currently opened and used as a sitting room/office, includes its own full bath and could easily be reconfigured back into a private bedroom. The living/dining area opens through sliders to an expansive deck overlooking the beautiful grounds, which include a historic oyster holding pond dating back to Madison's early oyster industry. This space also has a granite fieldstone fireplace and connects to a spacious, south-facing screened porch featuring charming original beadboard details. Additional highlights include a full walk-out basement offering excellent storage and flexible space. A special home ready for its next chapter.

46a Beach Ave, Madison

17 Linden Ln, Madison
$799,000
2 Beds ⋅ 1 Baths ⋅ 24183478 MLS
Coastal Paradise in the Heart of Madison! Welcome to one of Madison's most desirable shoreline beach communities, where coastal charm, breathtaking views, and endless outdoor recreation come together to create the perfect seaside retreat. This delightful cottage offers spectacular views of Fence Creek Salt Marsh and a glimpse of Long Island Sound. Kayak or paddleboard from the beach one block away (or directly from the back yard at high tide), enjoy morning walks along the ocean, stroll into town for coffee, and embrace the relaxed Connecticut shoreline lifestyle. Inside, this charming home features 2 bedrooms, 1 bath, and 3 additional rooms that capture the beauty of the surrounding landscape. Large windows invite natural light and showcase the stunning marsh vistas. The deck is ideal for entertaining or simply unwinding while taking in the abundant bird life. After a day at the beach, rinse off in the outdoor shower. Central air conditioning and heat offer three-season living, with the potential for winterization. Its location, just 3/4 of a mile from Madison's vibrant downtown, provides easy access to charming shops (including a renowned bookstore), restaurants, movie theater and library. Ideally situated between New York City and Boston, and approximately one hour from Rhode Island, rarely does an opportunity arise to own a waterfront-adjacent cottage in such a coveted Madison location. Come experience the beauty, tranquility, and timeless appeal of Shoreline Living.

17 Linden Ln, Madison

450 County Rd, Madison
$780,000
4 Beds ⋅ 3 Baths ⋅ 24201961 MLS
DESIRABLE 4 BEDROOM NORTH MADISON HOME. Nestled on 2.62 peaceful, tree-lined acres in desirable North Madison, this classic yellow Colonial combines timeless New England charm with spacious, modern comfort. Offering 2,600+ square feet of beautifully appointed living space, the four-bedroom, 2.5 bath home is anchored by rich hardwood floors throughout the home. The front Living Room is spacious, the Family Room has a warm, inviting wood burning fireplace that serves as the heart of the main floor. The light-filled layout includes a finished basement that provides versatile extra rooms for a home gym, media area, or private office, while central air conditioning ensures year-round comfort throughout. An attached two-car garage adds everyday convenience to this tranquil retreat. Outside, the property opens up to an impressive bluestone patio designed for seamless outdoor entertaining, or simply taking in the scenic, natural views of your vast private grounds. The setting balances serene seclusion with easy accessibility, placing you just minutes from local hiking trails, North Madison amenities, close to Durham, with the vibrant shops and beaches of downtown Madison, 15 minutes away. Perfect for both relaxing everyday life and hosting family and friends, this classic residence captures the very best of shoreline Connecticut living.

450 County Rd, Madison

53 Wellsweep Dr, Madison
$778,000
4 Beds ⋅ 3 Baths ⋅ 24173181 MLS
Tucked away in a quiet neighborhood just minutes from town and the beach, this split-level home sits on a generous lot with a beautifully landscaped front yard, classic rock walls, and a perfect balance of sun and shade for year-round outdoor enjoyment. Inside, newly restored hardwood floors run throughout the home complemented by vaulted ceilings that enhance the light-filled living and dining spaces. The layout offers a bright sunroom for additional sq ft, a cozy den, a convenient main-level bedroom, a basement perfect for a gym, and three additional bedrooms on the upper level with two updated full bathrooms. The kitchen offers two ovens and a gas stove top situated within the peninsula, perfect for entertaining. Step out from the sunroom onto the rear deck, which overlooks a private yard and a stunning salt water heated pool and spa - ideal for relaxing after a hard days work.

53 Wellsweep Dr, Madison

170 Mungertown Rd, Madison
$775,000
4 Beds ⋅ 2 Baths ⋅ 24192861 MLS
**7/26/26 Open House Cancelled** Updated, 4-bedroom, 2-bathroom New England gem boasting 2,348 square feet of thoughtfully designed living space. Pride of ownership shines through with improvements already completed for you, including a new roof (2026), freshly painted exterior (2026), a replaced septic system (2021), and a new well (2020). Interior features include a gorgeous remodeled kitchen with quartzite counters and stainless steel appliances that flows into a family room featuring dramatic cathedral ceilings and easy access to the rear yard entertaining space. The exterior is a true staycation paradise. The level backyard hosts a pristine in-ground pool paired with a dedicated pool shed equipped with electricity-ideal for pool storage. Peace of mind thanks to an upgraded 200-amp electrical service complete with a generator transfer switch. Perfectly situated just north of Route 1, this home offers the ultimate shoreline lifestyle. Enjoy being just a 5-minute drive to Madison's quintessential town center and a quick 8-minute drive to the beach. Move right in and start enjoying summer by the pool!

170 Mungertown Rd, Madison

89 Summer Hill Rd, Madison
$769,000
4 Beds ⋅ 3 Baths ⋅ 24184408 MLS
Set on a beautiful, private 1.25-acre lot in one of Madison's sought-after neighborhoods, this spacious, well maintained Colonial offers exceptional flexibility and comfort with nine rooms plus an additional sunroom. The kitchen is updated with granite countertops and newer appliances. Bathrooms have all been updated with tile and granite. The floors are hardwood throughout the home. Thoughtfully designed for both everyday living and entertaining, the home features generous living spaces, 2 fireplaces and a propane stove, abundant natural light, and a large Great room ideal for a playroom, home office, media room, or guest retreat. Enjoy the peace of mind provided by a whole-house generator, ensuring year-round convenience and security. The picturesque property offers a tranquil setting while remaining just minutes from Madison's town center, walking trails, beaches, schools, shopping, and commuter routes. A wonderful opportunity to make this well-maintained home your own in a premier shoreline community.

89 Summer Hill Rd, Madison

44 Sterling Park, Madison
$749,900
3 Beds ⋅ 3 Baths ⋅ 24194435 MLS
Move right into this meticulously maintained home, proudly offered for sale for the very first time by its original owners. This distinctive contemporary 3-bedroom home welcomes you with an inviting natural setting surrounded by mature trees, charming stone walls, and striking rock outcroppings. Inside, abundant natural light fills the thoughtfully designed living spaces, including a formal living room, dining room, and a cozy family room with a gas fireplace. The sunroom is a true highlight, featuring cathedral ceilings, skylights, and walls of windows that bring the beauty of the outdoors inside, creating a peaceful retreat to enjoy throughout the seasons. The fully applianced eat-in kitchen offers a breakfast bar, tile flooring, and a comfortable dining area ideal for morning coffee, casual meals, and entertaining. Upstairs, the spacious front-to-back primary suite serves as a private retreat with its own full bath, a walk-in closet, and a second lighted closet. Two generously sized bedrooms offer excellent closet space, with one featuring a private balcony. Additional features include central air and whole house generator. Set on a peaceful cul-de-sac, the home is just a short stroll to downtown shops, restaurants, coffee shops, beaches, and the country club. Perfectly positioned along the Connecticut shoreline, it also offers convenient rail access to both Boston and New York City, making it an exceptional year-round residence or weekend getaway.

44 Sterling Park, Madison

602 Durham Rd, Madison
$745,000
3 Beds ⋅ 2 Baths ⋅ 24170575 MLS
602 Durham Road delivers the lifestyle living by the shoreline is known for, starting the moment you pull into the circular driveway. The covered front porch sets the tone, but the backyard is the headline: a resort-caliber outdoor environment anchored by an in-ground pool, hot tub, covered patio with TV, outdoor kitchen with built-in grill, oversized high-top bar, pizza oven, basketball court, bocce court, putting green, and a flat park-like yard with manicured gardens and outdoor shower. A fully equipped pool house with electricity, refrigerator, and deep freezer completes the picture. This is the home people gather at - every weekend, all summer long. Inside, 2,248 square feet of polished, move-in ready living space matches the energy of the exterior. The kitchen is built for the home cook who takes it seriously - Wolf propane range, granite countertops, fresh backsplash, and generous counter space that flows openly into the dining room, where a beadboard ceiling and gas log fireplace create an atmosphere that's relaxed and refined at the same time. Hosting a dinner party or a casual Sunday morning, this space handles both effortlessly.

602 Durham Rd, Madison

69 Squires Rd, Madison
$738,000
3 Beds ⋅ 3 Baths ⋅ 24159316 MLS
Meticulously reimagined from top to bottom, this stunning contemporary home delivers 2,025 sq ft of turnkey luxury on over an acre of level land. Tucked on a peaceful street, the residence boasts 3 bedrooms and 3 full baths, highlighted by a main-level primary suite with its own fireplace, patio access, and spa-inspired bath. There is a versatile 2nd-floor suite with full bath: perfect for an office, den, or guest room. Light-filled and inviting, the open layout showcases gleaming hardwood floors, designer recessed lighting, and crisp new trim, railings, doors, and hardware throughout. The chef-inspired kitchen is a true centerpiece-outfitted with custom cabinetry, striking quartzite countertops, an expansive island, and premium GE appliances including a beverage fridge. It flows effortlessly into the dining and living spaces. All three baths have been transformed with modern tile, sleek vanities, and Moen fixtures. Thoughtful details include two cozy fireplaces, new windows in every bathroom, smooth ceilings, and fresh neutral paint. Behind the walls, everything is new: 200-amp electrical, complete plumbing overhaul, tankless water heater, high-efficiency heat pump, and central air. Step outside to a low-maintenance Trex deck, fire pit area, and landscaped grounds-ideal for entertaining or quiet evenings. Situated in a sought-after neighborhood, this exceptional home offers the perfect blend of modern elegance and effortless, worry-free living.H&B due 4/25 @6PM

69 Squires Rd, Madison

40 Harkness Dr, Madison
$735,000
4 Beds ⋅ 3 Baths ⋅ 24174837 MLS
Discover the perfect blend of modern luxury & classic charm at 40 Harkness Drive. This beautifully renovated colonial, set on a 1.23-acre lot, offers 2,657 sq ft of thoughtfully designed living space w/ 4 bedrooms & 2.5 bathrooms. Step through the double front doors into a stunning open-concept layout. The spacious dining room seamlessly flows into a brand-new kitchen, featuring custom cabinetry, quartz counters, central island w/ seating, walk in pantry & top-of-the-line stainless appliances. A renovated half bath & inviting living room boasts built-in cabinetry, while the family room is a offers a striking fireplace & slider doors leading to the yard or a door w/access the attached 2 car garage. Upstairs, the redesigned layout offers a luxurious primary suite complete w/a brand-new ensuite bath. 3 additional generously sized guest bedrooms share an all-new full bath. The lower level presents endless possibilities for future finished space, making it the perfect opportunity to expand living area. Renovation includes but not limited to: New Install (2) complete HVAC systems, New 1,250 septic tank, piping & d boxes. New 200 amp panel & breakers, 26 new windows, & slider door w/new stairs, new door to garage, New fully insulated basement ceiling, new hot water heater, New architectural roof w/50 year shingle(stripped to plywood & most of plywood replaced), Chimney was Total exterior repointed, recrowned, 17x29ss cap installed, repaired damper & cleaned, new bilco door & more!

40 Harkness Dr, Madison

238 Scotland Rd, Madison
$725,000
5 Beds ⋅ 4 Baths ⋅ 24179660 MLS
Welcome to 238 Scotland Road, a rare 5-bedroom home with private in-law accommodations, pool, situated on nearly an acre of privacy. A lovingly cared-for home offering exceptional space, comfort, and versatility. Features include hardwood floors throughout, central air conditioning, and a beautiful new primary suite designed for relaxation and convenience. The heart of the home is the updated kitchen, thoughtfully renovated and perfect for everyday living or entertaining. Just beyond, a bright and inviting three season sunroom provides the ideal place to unwind year-round and opens onto a Trex deck to the backyard and pool. Cozy up on cooler evenings beside the charming wood-burning stove, creating the perfect setting for relaxing nights at home. Step outside to enjoy the private inground vinyl-lined pool with a newer liner, offering endless opportunities for summer fun, entertaining, and making lasting memories with family and friends. Adding incredible flexibility, the property includes an attached in-law apartment with its own separate entrance and full bath, making it ideal for extended family, guests, or multi-generational living. Additional highlights include a newer roof, public water, generous living spaces, and a peaceful setting that feels secluded while remaining just minutes from town, beaches, shopping and dining. This well-loved home offers the perfect combination of privacy, thoughtful updates, and room to grow-ready for its next chapter.

238 Scotland Rd, Madison

91 Legend Hill Rd Unit 91, Madison
$725,000
3 Beds ⋅ 3 Baths ⋅ 24162610 MLS ⋅ Legend Hill BLDG.
In the heart of Madison, discover this exceptional 3-bedroom, 3 full bath condo that has been completely updated from top to bottom-right down to the door knobs. Every detail has been thoughtfully designed, offering a truly turnkey living experience. The stunning open floor plan welcomes you with a spectacular new kitchen featuring an oversized breakfast bar, stunning counters and loads of storage. The kitchen opens to the large dining. Hardwood floors flow seamlessly through the living room complete with a cozy fireplace. The living room opens to an oversized screened porch-perfect for relaxing or entertaining with stunning views & complete privacy. The bathrooms are nothing short of showstoppers, finished with high-end, modern touches.The main level also includes a spacious primary bedroom with a walk-in closet and luxurious full bath, a second bedroom, & additional full bath. Large convenient laundry room as well on the main level.The fully finished walk-out lower level expands your living space with a huge family room, third bedroom, and another full bath-ideal for guests or extended living. Additional highlights include a new gas furnace and a one-car garage.Enjoy resort-style amenities with access to a pool and tennis courts, all within a beautifully maintained complex just moments from everything Madison has to offer. From shopping, the beach,dining, the train station or movies on main street. Madison has it all. This incredible condo can be conveyed fully furnished.

91 Legend Hill Rd Unit 91, Madison

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