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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
343 Horse Pond Rd, Madison
$675,000
3 Beds ⋅ 3 Baths ⋅ 24207706 MLS
***Seller financing available - below market rate! 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
3 Poole Rd, Madison
$665,000
3 Beds ⋅ 3 Baths ⋅ 24216910 MLS
Escape the everyday and step into your own private sanctuary at 3 Poole Road, a charming 3-bedroom, 2.5-bathroom Log Cabin offering 2,237 square feet of light-filled, thoughtfully designed living space on nearly seven acres of serene, wooded grounds in Madison. Built in 2005, this comfortable Cape Cod style home features an intuitive, flexible floor plan with seamless flow between the main gathering areas and the expansive outside space. The upper level has two spacious bedrooms and extra living space overlooking the property's incredible setting, offering rare acreage, complete privacy, and endless possibilities for outdoor recreation, gardening, or potential expansion.

3 Poole 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
885 Boston Post Rd, Madison
$599,900
24168048 MLS
Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers just a short stroll from Madison's beautiful beaches in this high-visibility location. Whether you're looking to create a professional office, boutique retail space, or explore endless other possibilities, this is a rare chance to establish your business in one of the shoreline's most desirable communities. The potential here is truly unlimited!

885 Boston Post Rd, 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
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
23 Wilshire Rd Unit A, Madison
$550,000
2 Beds ⋅ 2 Baths ⋅ 24213023 MLS ⋅ Kensington Acres South BLDG.
Welcome to this charming two-bedroom end-unit in sought-after Kensington South, offering a private backyard and comfortable, low-maintenance living. The inviting living room features a fireplace and flows seamlessly into the kitchen and dining area. The bright, well-appointed kitchen offers granite countertops and stainless steel appliances. A delightful sunroom provides additional living space and a peaceful spot to relax. Two bedrooms and two full baths complete the home. Additional features include central air and natural gas. A wonderful opportunity to enjoy all the benefits of condominium living in a desirable community. So close to Madison town center, restaurants and beautiful beaches. Additional $92.67 per/mo. expiring 6/30/2027 for land lease.

23 Wilshire Rd Unit A, Madison
91 Neck Rd, Madison
$550,000
2 Beds ⋅ 2 Baths ⋅ 24217166 MLS
Charming and beautifully maintained 2-bedroom, 2-full-bath ranch located south of Route 1, just a short stroll to the beach! Light and bright throughout, this inviting home features hardwood floors, thoughtful architectural details, and a warm, welcoming atmosphere. The living room offers a wood-burning fireplace with a stove insert. The eat-in kitchen features a lovely bay window, additional shelving, and a charming built-in corner hutch. The spacious primary bedroom offers two closets, while the second bedroom provides flexibility for guests, a home office, or sitting area. French doors lead to a heated enclosed porch with louvered windows, offering a wonderful place to relax and enjoy the natural light. Outside, unwind on the patio surrounded by gardens and a charming white picket fence. The current owner has made numerous improvements, including a new furnace, security system, basement waterproofing system, new wood stove insert with fully relined chimney flue, chimney cap upgrades, cobblestone driveway and edging, updated kitchen stove, added attic and basement sill insulation, tree removal, kitchen shelving, brick walkway connecting the front and side entrances, and split systems in the living room and primary bedroom. Full basement and detached garage provide ample storage. Enjoy coastal living just minutes from downtown Madison, beautiful beaches, shopping, restaurants, and train station!

91 Neck Rd, Madison
273 Horse Pond Rd, Madison
$550,000
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
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
252 Boston Post Rd, Madison
$549,900
4 Beds ⋅ 2 Baths ⋅ 24216244 MLS
Experience the best of coastal living in this distinctive property, featuring a beautifully renovated main residence, an income-producing in-law residence, and generous grounds in one of Connecticut's most desirable shoreline communities. Set toward the rear of the .76-acre parcel, comfortably removed from Boston Post Road, the main home enjoys an attractive setting surrounded by lush greenery and magnificent mature trees. The expansive grounds provide a beautiful backdrop for outdoor entertaining, gardening, or simply relaxing in the natural surroundings. Extensively renovated throughout, the main residence combines contemporary style with everyday comfort and convenience. Enjoy a beautifully updated kitchen and bath, attractive new flooring, modern lighting, replacement windows, a new roof, and an updated heating system. These substantial improvements offer the immediate enjoyment of a move-in-ready home without the disruption and expense of a major renovation. A bright breezeway connects the home to its attached one-car garage, providing convenient, sheltered access, while the full basement offers valuable storage and utility space. A separate in-law residence toward the front of the parcel is currently leased for $1,700 per month. This rental income provides a meaningful financial advantage, helping offset ownership expenses while adding versatility and value.

252 Boston Post Rd, 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!There is a land leasehold fee of $100 due each month and is due to expire on June 30, 2033.

3 Currycross Rd Unit 3, Madison
270 Scotland Rd, Madison
$399,000
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
92 Scotland Rd Unit Lot. 3, Madison
$350,000
24033986 MLS
Build your dream home in the upscale shoreline community of Madison CT! Featured in Yankee Magazine as "Best Beach Towns" in Connecticut and not many land opportunities like this. Centrally located this approved lot is a very large 2.05 acre lot that is level, wooded, and private in a well established upscale neighborhood ONLY 1.2 miles from downtown and approximately 2 miles from Hammonasset State Park. Madison has so much to offer with distinguished beaches, a charming and pedestrian friendly downtown appealing to many tastes and interests including a cinema, award-winning bookstore, coffee shops, restaurants and boutiques. This is shoreline living with small town charm and urban sophistication. This lot also has a sister lot (1.20 acres) adjoining it listed as MLS #24033994.

92 Scotland Rd Unit Lot. 3, Madison
59 East St, Madison
$275,000
2 Beds ⋅ 1 Baths ⋅ 24218365 MLS
This is your perfect shoreline getaway in the heart of Madison. Set on one of the most desirable and generously sized lots in Duds Village, this delightful Renovated Two-Bedroom seasonal cottage affords you care-free coastal living. The Propane Furnace provides efficient heat to take the Chill out of the early Spring Mornings and Late Fall Evenings. The fully Remodeled Kitchen combines Quartz Countertops with High-End Stainless-Steel Appliances. The inviting finished Sunroom welcomes leisurely mornings and relaxed summer evenings, while the thoughtfully designed 751-square-foot interior provides comfortable living space. The expansive lot offers that rare privacy and ample room to enjoy outdoor living. Abutting Salt Meadow Park and located just moments from Hammonasset Beach State Park, the property combines natural beauty with easy access to some of the area's most treasured recreational destinations. Whether you're dreaming of a peaceful summer retreat, outdoor entertaining spaces, or a charming beach cottage tailored to your style, this property presents a remarkable opportunity in one of Connecticut's premier shoreline communities. Duds Village is a seasonal community open from April 1 through October 31. The land is leased, with the current annual lease amount of $5,400.

59 East St, 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
6 Woodland Rd Unit 4A & 4B, Madison
$265,000
24198543 MLS
INCREDIBLY CONVENIENT LOCATION just off Exit 60 of I-95 & Route 79...East Shore Medical Center, A 2,000 Sq Ft medical office condominium on the second floor in an elevatored building. Reception area, treatment rooms, offices & consulting rooms. Everything perfectly laid out for a medical practice. Across the street from Madison Ambulance. Lots of parkng. Easy access to Route 79, I-95 & Route 1. HVAC units are 1 year old. Building recently painted and re-roofed.

6 Woodland Rd Unit 4A & 4B, Madison
54 Railroad Ave, Madison
$250,000
24215018 MLS
Imagine building a home that reflects your vision in one of Connecticut's most desirable shoreline communities! This fully approved residential building lot at 54 Railroad Avenue is walking distance from downtown and offers an exciting opportunity to create your own special place in Madison, known for its timeless New England charm, beautiful beaches and welcoming village atmosphere. Enjoy nearby Hammonasset Beach State Park, charming downtown shops and restaurants, and convenient access to surrounding shoreline communities. A wonderful opportunity to put down roots and embrace the appeal of coastal Connecticut living.

54 Railroad Ave, Madison

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