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7 Milestone Ln, Madison
$699,900
4 Beds ⋅ 3 Baths ⋅ 24216661 MLS
Nestled on a beautifully elevated homesite, this classic Colonial offers the perfect blend of privacy, comfort, and New England charm. Set in a desirable neighborhood just minutes from charming Madison Village, the Town Green, shops, restaurants, and the stunning Connecticut shoreline, this home offers the perfect blend of location and lifestyle. This spacious 4-bedroom home features a welcoming living room with a fireplace, a formal dining room, an eat-in kitchen, and a generous family room with a second fireplace. A wonderful, sun porch overlooks the peaceful backyard, creating the perfect space to relax or entertain. Upstairs, you'll find four spacious bedrooms, including the primary suite with a private bath and walk-in closets. The finished lower level provides additional flexible living space for a recreation room, home office or gym. Additional highlights include a 2-car garage, newer roof, siding and windows, plus the convenience and peace of mind of natural gas and a whole-house generator. New septic tank installed to the current septic system. Neck River School district

7 Milestone Ln, Madison
3 Currycross Rd Unit 3, Madison
$545,000
2 Beds ⋅ 2 Baths ⋅ 24216462 MLS ⋅ Windermere East BLDG.
Don't miss this opportunity to own a beautifully updated Ranch in the desirable Windermere community! Nestled in a peaceful cul-de-sac setting, this home is the larger of the two ranch-style models and offers comfortable, versatile living with the added bonus of a family room featuring a new gas fireplace. Enjoy new luxury vinyl flooring thru the main living area and stylish new carpeting in the bedrooms. The updated kitchen features new appliances, including a gas stove with hood, refrigerator and dishwasher, along with quartz countertops, freshly painted cabinets with new hardware and a butcher-block island. The bathrooms have also been tastefully refreshed with new vanities, and new lighting above the sinks. The primary bathroom features a new bathtub, while the guest bath offers new shower doors and a new stackable washer and dryer. Besides the gas fireplace in the family room, a ceiling fan with light has been added, creating a comfortable space to relax or entertain. Year-round comfort is enhanced by a new Mitsubishi Electric heat pump and air-conditioning system. Additional improvements include an Anderson screen door. Step outside to enjoy the 12'x12' enclosed porch, a patio, garden area, and a park-like backyard. The adjacent garage adds everyday convenience. Exterior maintenance is provided. Just minutes from Madison's beautiful shoreline and charming downtown village!

3 Currycross Rd Unit 3, Madison
182 Green Hill Rd, Madison
$599,000
2 Beds ⋅ 3 Baths ⋅ 24215402 MLS
Timeless New England charm meets contemporary style in this beautifully remodeled Cape, where classic character and thoughtful modern updates come together effortlessly. The inviting interior features an open-concept kitchen and dining area designed for both everyday living and effortless entertaining. Just off the kitchen, a lovely deck extends the living space outdoors, creating the perfect setting for al fresco dining, relaxed afternoons, and gathering with family and friends. The spacious living room, centered around a wood-burning fireplace, offers warmth and timeless appeal. Two generously sized bedrooms, beautifully updated bathrooms, and California Closets provide comfort and refined functionality. The completely reimagined basement offers exceptional versatility, with flexible bonus spaces ideal for a home office, guest retreat, gym, playroom, or additional living area. A garage adds convenience and valuable storage. Ideally situated near town, local shops, beautiful beaches, and a brand-new elementary school, this home offers the best of coastal New England living, blending enduring charm, modern comfort, and a location that makes everyday life feel just a little more special.

182 Green Hill Rd, Madison
466 County Rd, Madison
$395,000
3 Beds ⋅ 2 Baths ⋅ 24215669 MLS
A terrific home at a remarkable price for Madison! This solid, well-maintained property offers incredible potential for buyers looking to make a home their own. Lovingly cared for more than 60 years by the original owner, this home is now ready for its next chapter. While cosmetic updates would enhance the interior, it offers the opportunity to move right in and make renovations over time, at your own pace. Notable improvements include low-maintenance vinyl siding, a new well pump, a new garage door, a whole-house generator, and a roof just over 10 years old. The property also boasts a large, private lot with attractive landscaping, providing a peaceful setting to enjoy the outdoors. The best part of this home is the four season bonus room addition featuring vaulted ceiling and flooded with natural light. It provides the perfect space to entertain company. With its solid construction, history of care, and opportunity for personalization, this property offers exceptional value. Bring your vision and make this well-loved home your own! The home is an estate sale and is being sold as-is. Offers must include as-is rider.

466 County Rd, Madison
28 North St, Madison
$265,000
1 Beds ⋅ 1 Baths ⋅ 24215713 MLS
Dream of sunny beach days and enjoying all that the shoreline lifestyle offers? Then this one is for you ! Fully turn-key, this seasonal cottage is directly bordering Hammonasset Beach State Park, only a short walk away. This cottage has enough room to sleep eight or more people comfortably in a cozy environment. Enjoy the park's two miles of sandy beaches, secluded coves, picnic areas and wildlife sanctuary with 936 acres of protected waterfront lands all easily accessible from your quaint cottage via a direct walking path and a bike path. Large shed for hosting parties and extra storage along with new firepit for those beautiful summer nights! Enjoy your morning coffee with the large fenced in wrap around deck and after those sandy beach days you can rinse off in the solar outdoor shower with privacy screen. This purchase MUST be all cash or personal/home equity loan and is seasonal April 1st-October 31st. Cottage is on leased land and does not qualify for conventional financing. New deck, new floors, new shed, new bathroom, newly painted and fully furnished! This property also comes with two electric scooters to get you to the beach even faster! This cottage is the perfect summer oasis and amazing alternative to RV living. Do not miss this opportunity to make this your next home!

28 North St, Madison
67 Nortontown Rd, Madison
$695,000
4 Beds ⋅ 2 Baths ⋅ 24215254 MLS
Take a 3D Tour OR Enjoy a Video Walkthrough 24/7! Move right into this charming 4 BR, 2 Bath Madison farmhouse offering 1,956 SF of living space on a nearly 1-acre, level lot backing to protected land trust open space! Built in 1940 with a spacious 1980 addition, this home combines classic character with thoughtful updates, including the convenience of a first-floor primary BR. Three additional BRs upstairs provide flexibility for guests, hobbies or work-from-home needs. Beautiful hardwood floors, a welcoming Living Room with stone fireplace & sunny bay window, a bright, spacious Kitchen with breakfast bar, formal Dining Room, home Office & an expansive Rec Room with direct access to the rear deck provide plenty of room to spread out. The major improvements are already complete: NEW roof (2024), furnace & central A/C (2023), water heater (2022), septic tank (2011), replacement windows (2008) & upgraded 200-amp electrical service. Low-maintenance aluminum siding adds to the appeal. Relax on the inviting 3-season enclosed front porch with windows or entertain on the expansive rear deck overlooking the level backyard & protected land trust open space. A detached 2-car garage offers convenient loft storage. Enjoy quick access to I-95, Madison's charming village center, shoreline & Hammonasset Beach State Park. At $695,000, this move-in-ready home offers space, flexibility & significant recent improvements. Schedule your private showing today!

67 Nortontown Rd, Madison
41 Bradley Corners Rd, Madison
$569,900
4 Beds ⋅ 3 Baths ⋅ 24211348 MLS
Beautifully updated and wonderfully maintained, this exceptional 4-bedroom Colonial offers a great & comfortable lifestyle in a highly desirable Madison location. From the moment you enter, you'll appreciate the natural light, handsome hardwood floors, and thoughtful improvements throughout. At the heart of the home is a gorgeous, sun-filled kitchen featuring a big bay window, center island, granite countertops, gas range, stainless appliances, and pantry. Just beyond the kitchen, the inviting family room makes a wonderful gathering space with its soaring cathedral ceiling, wood stove, and glass French doors opening to a fabulous multi-level deck. The spacious living room is filled with natural light, while the dining room is perfectly suited for entertaining. Upstairs, the private primary suite features a remodeled full bath, accompanied by three additional bedrooms and a second beautifully updated full bath. The extensive list of improvements includes replacement windows, brand-new roof, new oil tank, new well pump and water softener, and a whole-house generator.Outside, the attractive, easy-care yard provides plenty of room to relax and entertain, while the two-car garage and central air adds everyday convenience. A wonderful opportunity to enjoy the best of Madison living in a home where style, comfort, and quality updates come together beautifully. OFFERS HAVE BEEN RECEIVED. HIGHEST & BEST WITH NO ESCALATIONS TO BE IN BY 10AM MONDAY OCTOBER 19th

41 Bradley Corners Rd, Madison
69 Bradley Corners Rd, Madison
$850,000
7 Beds ⋅ 4 Baths ⋅ 24214953 MLS
Welcome to 69 Bradley Corners Road, a truly unique property nestled on over 6 acres in beautiful Madison! Offering an incredible combination of privacy, space, and resort-style amenities, this home is anything but ordinary. Enjoy your own private retreat complete with a picturesque pond, tennis court, and in-ground pool, perfect for entertaining or simply enjoying everything this property has to offer. Inside, you'll find a stunning primary suite and a spacious layout featuring a full in-law apartment for guests or multigenerational living. Looking for even more space? The lower level offers additional potential to expand your living area and make it your own. With over 6 acres to enjoy, endless possibilities, and amenities rarely found together in one property, this is truly a one-of-a-kind opportunity. Properties like this don't come along often. Don't miss your chance to see everything this incredible Madison home has to offer!

69 Bradley Corners Rd, Madison
16 Tamarac Dr, Madison
$599,000
3 Beds ⋅ 2 Baths ⋅ 24214239 MLS
Welcome to this beautifully maintained home on a cul-de-sac street. Low traffic, great for play. When entering this inviting home, the foyer greets you with the natural light of the main living room's oversized windows creating a bright ambience that flows seamlessly into the eat-in kitchen and dining area. The updated kitchen features newer stainless steel appliances (2024), while beautiful hardwood floors add warmth and character throughout the main level. Just a few steps up, you'll find three generously sized bedrooms,including a spacious primary bedroom, all featuring beautiful hardwood floors that continue into the hallway. Entire interior painted, along with new interior doors (2024). The versatile lower level offers additional living space, complete with a cozy raised hearth fireplace w/newer wood-burning/pellet stove (2023), newly renovated full bathroom and laundry area(2020). Whether you envision a comfortable family room, home office,or creative retreat,this space offers endless possibilities. Step outside onto the expansive deck overlooking a lush,lovingly landscaped property and spacious, level yard.This private outdoor oasis is perfect for summer entertaining,relaxing evenings, or simply enjoying the peaceful surroundings. Complete with a two-car garage and ideally situated just minutes from schools (Neck River, Polson,Hand) the shoreline, shopping, restaurants, and interstates, this home offers the perfect combination of style, functionality, and convenience.

16 Tamarac Dr, Madison
56 River Edge Farms Rd, Madison
$1,200,000
3 Beds ⋅ 3 Baths ⋅ 24115570 MLS
Park like property with enchanting pathways to Neck River. Charming pathways have native perennials and many choice bushes and trees. All thoughtfully planned. Relax and view the osprey. The home has beautiful hardwood floors, recently painted inside and many updates. The new chef will enjoy the Gedney kitchen. Living rm w/beautiful fplc open to Din rim. Family room, 3 bedrms, 2.1 baths. This is a very special ranch home in a coveted neighborhood with all that beautiful Madison has to offer! Great schools, beaches, new library, high end small stores, restaurants and much more!

56 River Edge Farms Rd, Madison
7 Highland Ter, Madison
$799,000
3 Beds ⋅ 1 Baths ⋅ 24213904 MLS
This "Diamond in the Rough" is ready for its next owners to create lasting memories. Located just a short walk to a private association beach in one of Madison's most desirable shoreline neighborhoods, this home offers an incredible opportunity to make it shine. While it does need TLC, the investment is well worth it , as proven by the beautifully-transformed nearby homes. Bungalow in style, the home has the original beadboard wainscoting on the walls and ceilings, reminiscent of the 1920's, and consists 5 rooms including 3 bedrooms and a LR/DR combination with a wood stove that is currently in the LR fireplace. One might imagine that the enclosed front porch had been used as a sleeping porch during the summer months. There is central air conditioning and a whole-house generator plus a 2-car detached garage. Enjoy all Madison has to offer, which includes excellent restaurants, a private award-winning bookstore and cafe in the center of town, a wonderful library and several delightful shops in which to indulge one's self. The Green in the center of town hosts many cultural events, including the popular July 4th concert featuring a symphony orchestra's performance of well-known patriotic music.

7 Highland Ter, Madison
24 Buck Hill Rd, Madison
$1,125,000
4 Beds ⋅ 3 Baths ⋅ 24200335 MLS
Set on a prime corner lot, this classic New England colonial is perfectly sited to welcome you home. The professional landscaping and stunning hardscaping accent this spectacular property. Step inside to a sun-drenched two-story foyer where detailed wainscoting and warm hardwood floors greet you. Elegant crown molding and custom paneling seamlessly frame the light-filled main spaces. At the center of daily life sits a custom chef's kitchen with an oversized island made for large or small gatherings. It flows into a family room anchored by a cozy fireplace, offering endless room for all - perfect for holidays or everyday! Access the deck and patio from either the family room or the kitchen and appreciate the added space for overflow when entertaining. Upstairs, the primary suite is surrounded by recessed panel wainscoting and crowned with an elegant tray ceiling, features a walk-in closet and expansive bathroom. Three spacious bedrooms complete the second floor as well as a hall bath, laundry and abundant storage. Expanding your options, a massive bonus room stretches over the entire three-car garage, ideal for a media room, play area, or home office.

24 Buck Hill Rd, Madison
22 Kingsbridge Way Unit 22, Madison
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 24213580 MLS
Welcome to a truly special waterfront residence where sophisticated updates, thoughtful design, and an extraordinary setting come together. A completely rebuilt and expanded deck, beautifully appointed with cable rail, takes full advantage of the year-round Hammonasset River views. Inside the kitchen is truly a dream come true, featuring tasteful, sophisticated finishes and an impressive 10' island. The first floor has been extensively remodeled to create an open, effortless flow throughout the living spaces. Included in this remodel is exquisite white oak flooring. One of the home's most captivating features is the stunning sunroom, transformed from what was once a porch and rebuilt from the studs out into a wonderful year-round space overlooking the river. The upper floor has been completely repainted and offers a spacious, versatile layout. The private primary ensuite with a walk-in closet is complemented by 3 good-sized bedrooms. At the heart of the bedroom level is a wonderful expansive loft overlooking the family room below. Filled with possibilities, this peaceful retreat is ideal for a home office, hobby space, library, or a cozy den - providing a quiet escape while remaining connected to the main living area. Enjoy the convenience of this location which is within walking distance to Hammonasset Beach State Park, while downtown Madison is just minutes away.

22 Kingsbridge Way Unit 22, Madison
22 Kingsbridge Way Unit 22, Madison
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 24211427 MLS ⋅ Strathmore Farms BLDG.
Welcome to a truly special waterfront residence where sophisticated updates, thoughtful design, and an extraordinary setting come together. A completely rebuilt and expanded deck, beautifully appointed with cable rail, takes full advantage of the year-round Hammonasset River views. Inside the kitchen is truly a dream come true, featuring tasteful, sophisticated finishes and an impressive 10' island. The first floor has been extensively remodeled to create an open, effortless flow throughout the living spaces. Included in this remodel is exquisite white oak flooring. One of the home's most captivating features is the stunning sunroom, transformed from what was once a porch and rebuilt from the studs out into a wonderful year-round space overlooking the river. The upper floor has been completely repainted and offers a spacious, versatile layout. The private primary ensuite with a walk-in closet is complemented by 3 good-sized bedrooms. At the heart of the bedroom level is a wonderful expansive loft overlooking the family room below. Filled with possibilities, this peaceful retreat is ideal for a home office, hobby space, library, or a cozy den - providing a quiet escape while remaining connected to the main living area. Enjoy the convenience of this location which is within walking distance to Hammonasset Beach State Park, while downtown Madison is just minutes away.

22 Kingsbridge Way Unit 22, Madison
14 Bower Rd, Madison
$599,900
4 Beds ⋅ 2 Baths ⋅ 24212728 MLS
Nestled on a picturesque stretch of Madison's desirable shoreline community, this exceptional property offers the perfect blend of New England charm, privacy, and convenience. Set on a beautifully maintained lot, 14 Bower Road provides an inviting setting for year-round living or a relaxing coastal retreat. Thoughtfully designed living spaces are filled with natural light, creating a warm and welcoming atmosphere throughout. The home features spacious gathering areas, a well-appointed kitchen, comfortable bedrooms, and seamless indoor-outdoor living ideal for entertaining family and friends. Outdoor spaces offer room to relax, garden, or simply enjoy the tranquility of the surrounding landscape. Ideally located just minutes from Madison's vibrant town center, beaches, boutiques, restaurants, and commuter routes, this property combines a peaceful residential setting with easy access to everything the Connecticut shoreline has to offer. A two-car attached garage and full walk-out basement provide excellent storage, workshop space, or future finishing potential. The private backyard offers plenty of room for entertaining.

14 Bower Rd, Madison
1209 Durham Rd, Madison
$999,000
5 Beds ⋅ 5 Baths ⋅ 24211566 MLS
Live the Connecticut Shoreline Life on 4 Private Acres. Picture mornings on your sun-filled balcony overlooking open fields, afternoon walks along Madison's public beaches, and evenings on the covered patio as the light fades over the tree line and old stone walls. Pastoral. Private. Purposeful. The main house, 3-bedroom and 2.5-bathroom, has wide wood flooring throughout. The primary ensuite has a private balcony accessed through private double sliding glass door. Two separate staircases. One staircase gives private access to primary bedroom. Livingroom, dining room, eat-in-kitchen, open floor plan, and enclosed porches provide flexible living space. Enclosed potting room off of the kitchen offers easy access to garden beds for wholesome farm to table dinners.

1209 Durham Rd, Madison
270 Scotland Rd, Madison
$449,000
3 Beds ⋅ 2 Baths ⋅ 24210705 MLS
Tucked away on a private setting high above Scotland Road, 270 Scotland Road offers the perfect combination of privacy, space, and natural beauty. Set on approximately 2 acres of lightly wooded land, this 3-bedroom, 1.5-bath raised ranch enjoys elevated surroundings with seasonal views toward the Hammonasset River. The main level features a comfortable, flowing layout with hardwood floors throughout the spacious living room, complete with a fireplace that creates a warm and inviting focal point. The updated kitchen offers stainless steel appliances, tiled flooring, and a generous dining area with plenty of space for everyday living and entertaining. Three bedrooms and a full and half bath are conveniently located on the main level. Downstairs, you'll find additional finished living space with a beautiful brick fireplace, offering flexibility for a family room, home office, recreation area, or guest space. Set back in a private, lightly wooded setting, this home offers the opportunity to enjoy the peace and privacy of acreage while remaining conveniently located in Madison. With its elevated setting, river views, spacious lot, and flexible living space, 270 Scotland Road is a property worth seeing in person.

270 Scotland Rd, Madison
273 Horse Pond Rd, Madison
$600,000
5 Beds ⋅ 2 Baths ⋅ 24210111 MLS
**Offered for the first time in over 54 years, this oversized ranch provides exceptional space, flexibility, and charm. Originally built in 1972 by a longtime Madison resident for his two daughters, this 2,240squarefoot home has been thoughtfully designed to accommodate a variety of living arrangements. Located in Madison's desirable southern section on a generous 1.33acre lot, the property offers convenient access to the downtown village, sandy town beaches, Hammonasset State Park's walking trails, and Madison's Town Campus. It's a rare opportunity to enjoy privacy while remaining close to everything Madison has to offer. This unique residence was constructed as a true duplex ranch, featuring two full kitchens, two living rooms, and two full baths-all connected and all on one level. A welcoming front foyer provides two separate entrances, complemented by two additional rear entrances. With three bedrooms on one side and two bedrooms on the other, the layout is ideal for an inlaw suite, multigenerational living, or simply enjoying the benefit of five total bedrooms and abundant square footage. Craftsmanship from a bygone era is evident throughout, with many rooms showcasing the original parquet hardwood floors. Both kitchens open directly to the expansive and private rear yard, offering wonderful outdoor enjoyment and potential for future expansion if desired. Don't miss this rare chance to own two homes in one-a truly special offering in Madison.

273 Horse Pond Rd, Madison
371 Race Hill Rd, Madison
$375,000
3 Beds ⋅ 2 Baths ⋅ 24209422 MLS
Welcome to 371 Race Hill Road, a 3-bedroom, 2-bath home offering 1,236 square feet of comfortable living on a private 1.12-acre lot in desirable Madison. The well-laid-out floor plan makes everyday living easy, while the generous yard gives you room to garden, play, and entertain. Recent updates include a new electric water heater (2025), and the home is heated by an oil-fired furnace with a 330-gallon tank. Conveniently located near Madison's shoreline, town center, shopping, and dining, with easy access to I-95. Furnishings are available for purchase, offering the incoming buyer a turnkey option.

371 Race Hill Rd, Madison
150 Race Hill Rd, Madison
$799,999
4 Beds ⋅ 3 Baths ⋅ 24208079 MLS
A rare and remarkably charming Antique in one of Madison's most picturesque settings. Set on 7+ acres along quiet Race Hill Rd, this beautifully preserved circa-1764 Cape blends centuries of character with thoughtful updates and the ease of modern living. Originally restored to the studs in 1996, the 2,091 sq.ft. main house retains an extraordinary amount of its original character, including chestnut flooring, period hardware, exposed beams and other details that give the home a wonderful sense of history. The floor plan is warm and inviting. The dining area opens to a family room with rustic beams, one of the original fireplaces and windows overlooking the private grounds. The family room, which could also work as a 1st floor bedroom, is highlighted by a 2nd original fireplace, built-ins and a full bath. The formal living room is distinguished with a 3rd fireplace, loads of windows and original cabinetry. A charming kitchen with cathedral ceilings and exposed beams, and a terrific sun room with a stone floor and private entrance complete the main living spaces. Upstairs you'll find three bedrooms and a full bath. And then there is the guest cottage! A beautifully renovated, year-round 701 sq.ft. legal one-bedroom cottage, that is an exceptional addition to the property-ideal for guests, extended family, a private office or rental use. Thoughtfully refinished and entirely independent, the cottage adds a level of flexibility rarely found.

150 Race Hill Rd, Madison
42 Concord Dr, Madison
$799,900
4 Beds ⋅ 3 Baths ⋅ 24206829 MLS
Perched on a scenic knoll in a highly desirable neighborhood, this classic colonial exudes curb appeal. A newly laid, meandering brick walkway leads to two inviting front entrances. Inside, the welcoming foyer opens to a sun-drenched living room that flows seamlessly into a beautifully renovated kitchen. A chef's dream, the kitchen boasts crisp white cabinetry, a contrasting grey-washed center island with waterfall "Carrara-style" quartz countertops, and a spacious dining area perfect for hosting large gatherings. French doors open to a serene four-season porch and a sizable deck, making indoor-outdoor entertaining effortless. The main level also features a generous family room with a cozy gas fireplace. With its own private entrance, this versatile space is ideal for an in-law suite, au-pair quarters, or a quiet home office. Upstairs, the primary suite is a true sanctuary, complete with a walk-in closet and a tastefully renovated, spa-like bath featuring heated floors. Three additional spacious bedrooms, all customized with California Closets, share a second beautifully updated full bath. Freshly painted throughout, the home also features a finished lower level with brand-new composite flooring and a highly functional mudroom just off the garage. This is a lovely home in a sought after private neighborhood and the community of Heatherwood is special within itself- come and experience all that it has to offer.

42 Concord Dr, Madison
343 Horse Pond Rd, Madison
$675,000
3 Beds ⋅ 3 Baths ⋅ 24207706 MLS
***Seller financing available to qualified buyers, Ask agent for details*** This sun-drenched and beautifully updated Cape offers a rare blend of charm, versatility, and an exceptional shoreline location. With two distinct living spaces, the property presents an outstanding opportunity for multigenerational living or a compelling investment property. The main residence features a stylishly renovated kitchen opening to a spacious dining area, two bedrooms-including an impressively spacious primary bedroom-two full baths, and a fabulous rear deck perfect for outdoor dining and entertaining. The attached in-law suite offers privacy and independence with its own updated kitchenette, full bath, washer and dryer, and beautiful open loft-style bedroom-ideal for extended family, guests, a private home office, or potential rental income. Outside, enjoy a large detached garage, hot tub, and storage shed. Located across from Cole's Farm, with a fishing pond just a short walk away and Hammonasset Beach State Park within an easy bike ride. Convenient to scenic trails, downtown, shopping, and dining, this unique property offers extraordinary flexibility and coastal living at its best!

343 Horse Pond Rd, Madison
39 Mill Rd, Madison
$550,000
5 Beds ⋅ 2 Baths ⋅ 24206863 MLS
The Perfect Location on picturesque 3/4 of an Acre. Walk to Hammonasset State Park and enjoy the Trails and 2-Miles of Pristine Sandy Beach ~ This Antique Saltbox boasts a total of 2,262 square feet of heated living space. Windows have been upgraded with Pella Double Pane Insulated Windows throughout. Included in the floor plan is a legal 1-Bedroom Apartment on the first floor. You'll need to Roll up your sleeves and do some work, but the results should pay dividends.

39 Mill Rd, Madison
3 Little Hollow Rd, Madison
$795,000
4 Beds ⋅ 3 Baths ⋅ 24205125 MLS
Welcome home to this classic four-bedroom Colonial offering timeless charm, modern updates, and an ideal layout for everyday living, complete with gorgeous wide plank flooring throughout. Freshly updated, the home features stylish new light fixtures and major mechanical upgrades, including a new roof (2022) and a new Carrier HVAC system for the second floor (2026). At the heart of the main level is an eat-in kitchen with cabinets painted in 2022, a new dishwasher (2024), and a spacious dining area set in front of a cozy fireplace. Sunlight pours into the breathtaking family room featuring soaring vaulted ceilings and a warm gas fireplace. Glass French doors open from the welcoming foyer into the living room, which boasts its own fireplace and connects seamlessly to the formal dining room. A dedicated mudroom off the kitchen includes a new washer and dryer (2024), alongside a convenient first-floor half bath. Upstairs, the primary suite serves as a peaceful retreat with vaulted ceilings, an expansive walk-in closet, and a private full bath. Three additional generous bedrooms share a renovated full bath with double sinks. Step outside to an impressive deck overlooking a lush yard-perfect for outdoor dining, playing, or relaxing. Ideally located just minutes from top-rated schools, vibrant town amenities, and picturesque local beaches, this move-in-ready property offers the ultimate combination of space, style, and peace of mind.

3 Little Hollow Rd, Madison
1 Hampshire Rd Unit 1, Madison
$695,000
2 Beds ⋅ 2 Baths ⋅ 24205396 MLS ⋅ Kensington Acres North BLDG.
Downsize Without Giving Up the Space You Need! Looking to downsize but still need generous storage, a workshop, and dedicated space to work from home? The largest condo in desirable Kensington Acres North offers an exceptional combination of comfort, flexibility, and space. This stand-alone unit features a spacious primary suite plus a guest bedroom. The open living and dining areas flow seamlessly to a screened porch, perfect for relaxing or entertaining while looking into your private, spacious backyard. The kitchen features bar seating with new counter tops by Gedney. Beautiful,new laminate floors run throughout the home. For those working from home or pursuing creative projects, the property offers a truly unique advantage: walk through the main house to an office and studio with a large seating area, half bath, and separate entrance-ideal for a home office. Storage and workshop space are equally impressive. A walk-up attic provides abundant storage, while the nearly 1900-square-foot basement offers tremendous potential and could be easily finished to create the workshop, recreation space, or additional living area you've been looking for. And the location is hard to beat. Hummer Pond is on the property plus enjoy easy access to Hammonasset State Park, East Wharf Beach, and downtown Madison, all just a short walk away. Downsize your home, not your lifestyle. Come see all this exceptional condo has to offer.

1 Hampshire Rd Unit 1, Madison
148 Mungertown Rd, Madison
$1,149,000
4 Beds ⋅ 4 Baths ⋅ 24205471 MLS
A Rare Madison Historic Homestead - Built with Purpose, Rich in History Discover a truly distinctive property at the former Helen Foster Snow homestead. The home was owner-built for his own family, reflecting a personal vision of home and a place to put down roots, not a property created simply for resale. Its history and individuality set it apart from the ordinary. This special offering includes two separate parcels totaling approximately 3.02 acres. The approximately 1.5-acre homesite features the main residence, a separate one-bedroom guest house, two barns, and a picturesque pond, offering a unique combination of historic character, flexible living space, and room to pursue your interests. An additional approximately 1.52-acre parcel is included, providing extra land and future possibilities. Buildability has not been confirmed, and buyers are encouraged to conduct their own due diligence regarding zoning, approvals, and potential uses. Whether you envision multigenerational living, space for hobbies and creative pursuits, a workshop, or simply a property with character and room to spread out, this distinctive Madison homestead offers a rare opportunity to make a special place your own. More than a house, this is a property with a story, built for family and ready for its next chapter conveniently located just minutes from Hammonasset Beach State Park, The Surf Club, and all that the Connecticut shoreline has to offer.

148 Mungertown Rd, Madison
23 Esterly Farms Rd Unit 23, Madison
$489,000
2 Beds ⋅ 3 Baths ⋅ 24203806 MLS ⋅ Esterly Farms BLDG.
Welcome to 23 Esterly Farms, an exceptional end-unit townhouse offering the perfect blend of style, comfort, and turnkey convenience in one of Madison's most sought-after condominium communities. This meticulously maintained 2-bedroom, 2.5-bath home has been thoughtfully updated throughout, allowing you to move right in and enjoy worry-free living. The sun-filled interior showcases fresh paint, all-new Harvey replacement windows, updated lighting, new window treatments, and a beautifully remodeled primary bath. The refreshed kitchen features brand-new stainless steel appliances, while the inviting living area is highlighted by a fireplace with elegant new glass doors. Additional upgrades include a new washer and dryer, delivering everyday convenience and modern functionality. Significant mechanical improvements provide added peace of mind, including a new furnace, central air condenser, and hot water heater. Nearly every major system has been updated, making this home truly move-in ready.

23 Esterly Farms Rd Unit 23, Madison
38 Church Ln, Madison
$699,000
4 Beds ⋅ 2 Baths ⋅ 24198873 MLS
Welcome to 38 Church Lane, where exceptional custom renovations meet a captivating Madison setting. Perched high on a large corner lot surrounded by mature trees, this thoughtfully updated 4-bedroom, 2.5 bath home offers sophisticated finishes, a flexible floor plan ideal for multi-generational living and privacy just minutes from Madison's town center and shoreline. The stunning kitchen, custom-crafted by Gedney Kitchens, features bespoke cabinetry and premium finishes, while an oversized fireplace anchors the inviting living room. The finished lower level includes a comfortable den with Vermont Castings wood-burning stove, custom Gedney wet bar, light-filled bedroom/office, and spa-inspired renovated bath with dual-head shower, heated floors, and heated towel rack. Outside, a brand-new composite deck overlooks terraced grounds with mature trees, stonework, curved pathways, and inviting spaces to garden, gather, and explore. An existing front-yard pond scape offers intriguing possibilities for future re-imagining. Hardie board siding with AZEK trim provides a remarkably low-maintenance exterior, complemented by energy-efficient windows and central air. Minutes from Madison's shops, dining, and beautiful shoreline beaches, this one-of-a-kind property truly must be experienced in person.

38 Church Ln, Madison
6 Bower Rd, Madison
$559,900
3 Beds ⋅ 1 Baths ⋅ 24203485 MLS
Escape to the Connecticut shoreline with this beautifully styled Cape, ideally situated in desirable Madison. Offering 3 bedrooms and 1 full bath, this charming home features inviting indoor and outdoor living spaces designed for comfortable everyday living and relaxed coastal living. Set on a private, lightly wooded corner lot, the property offers a peaceful sense of privacy while remaining close to everything Madison has to offer. Recent improvements include new cedar siding, windows throughout with custom window treatments, propane fireplace installation, and professional interior painting, all completed in 2025. The roof and septic system were both replaced in 2022. Just a 5-minute drive to vibrant downtown Madison, enjoy easy access to charming boutiques, restaurants, and cafes, as well as Hammonasset Beach State Park, with miles of sandy shoreline and scenic coastal walks. Convenient access to I-95 puts downtown New Haven approximately 25 minutes away. Turnkey and thoughtfully updated, this inviting Cape offers the perfect blend of classic New England charm, modern improvements, and an exceptional shoreline location. A wonderful opportunity to enjoy the best of Madison living in a peaceful coastal setting.

6 Bower Rd, Madison
67 Blakeman Rd, Madison
$650,000
3 Beds ⋅ 3 Baths ⋅ 24172475 MLS
BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which offers a full kitchen, full bath, a private bedroom and a cozy living area anchored by a stone fireplace and two separate exterior entrances. This setup is ideal for multi-generational living, a great guest suite or potential rental income. Maybe live in this while redoing the other portion. The property is a double lot that accommodates four dedicated parking spaces - a true luxury for beachside living. Best of all, the property is located where no flood insurance is required, offering peace of mind alongside the salt air. Whether you choose to polish this unique gem or start fresh with a custom build, this is the perfect canvas for your seaside lifestyle.

67 Blakeman Rd, Madison

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