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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

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$599,000

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.

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$395,000

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. **HIGHEST/BEST DUE BY 6 PM- 10/26. **

3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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. **HIGHEST/BEST DUE BY 6 PM- 10/26. **

466 County Rd, Madison

$250,000

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.

ACTIVE Status ⋅ 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

$569,900

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

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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

$850,000

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!

7 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$999,000

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.

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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

$6,000

TIMELESS 1910 CHARM MEETS MODERN COMFORT IN DOWNTOWN MADISON! Step into a perfect blend of historic character and contemporary convenience with this beautifully renovated 1910 home in an unbeatable downtown Madison location. From the moment you arrive, the oversized front porch welcomes you to sit back and enjoy the vibrant neighborhood atmosphere. Inside, stunning original hardwood floors and classic vintage features flow throughout a spacious, light-filled floor plan. The expansive living room offers abundant space for gathering, while the updated kitchen provides the modern functionality you need for everyday living and entertaining. Unwind in the cozy sunroom-a serene spot for reading or taking in natural light year-round. Featuring 4 generous bedrooms on the 2nd floor, this home easily adapts to your lifestyle, whether you need dedicated work-from-home spaces or extra guest rooms. Offered partially furnished and situated just moments from local shops, dining, and town amenities, this property delivers the ultimate in-town lifestyle.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211360 MLS

TIMELESS 1910 CHARM MEETS MODERN COMFORT IN DOWNTOWN MADISON! Step into a perfect blend of historic character and contemporary convenience with this beautifully renovated 1910 home in an unbeatable downtown Madison location. From the moment you arrive, the oversized front porch welcomes you to sit back and enjoy the vibrant neighborhood atmosphere. Inside, stunning original hardwood floors and classic vintage features flow throughout a spacious, light-filled floor plan. The expansive living room offers abundant space for gathering, while the updated kitchen provides the modern functionality you need for everyday living and entertaining. Unwind in the cozy sunroom-a serene spot for reading or taking in natural light year-round. Featuring 4 generous bedrooms on the 2nd floor, this home easily adapts to your lifestyle, whether you need dedicated work-from-home spaces or extra guest rooms. Offered partially furnished and situated just moments from local shops, dining, and town amenities, this property delivers the ultimate in-town lifestyle.

25 Wall St, Madison

$799,999

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.

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$799,900

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.

4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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

$675,000

***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!

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$695,000

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.

2 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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

$2,800

This home is available from October 1 through May of 2027 as a furnished academic rental. Enjoy the comfort of this 2-3 bedroom home with a wonderful beach at the end of the street. From the living room through the updated kitchen is beautiful new flooring. A cute separate dining room is off of the kitchen. At the back of the house is a cozy den and a porch enclosed with sliding glass doors. A bedroom with a full updated bath nearby is on the 1st floor. Upstairs is a full 2nd bedroom and a full bath with an option for a 3rd bedroom or office space.

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24204883 MLS

This home is available from October 1 through May of 2027 as a furnished academic rental. Enjoy the comfort of this 2-3 bedroom home with a wonderful beach at the end of the street. From the living room through the updated kitchen is beautiful new flooring. A cute separate dining room is off of the kitchen. At the back of the house is a cozy den and a porch enclosed with sliding glass doors. A bedroom with a full updated bath nearby is on the 1st floor. Upstairs is a full 2nd bedroom and a full bath with an option for a 3rd bedroom or office space.

41 Harbor Ave, Madison

$650,000

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.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$499,900

First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The adjacent dining room also has sliders to a patio. The kitchen with breakfast bar is waiting for your personal touches. Down the hall you will find 2 spacious guest bedrooms with large closets that share a hall bath. The primary bedroom with walk-in closet has its own full bath. Downstairs is a large family room with a wood stove to keep things cozy and sliders to an additional patio. The laundry is also located on this level. Though located in a private wooded setting, this home is conveniently located to town, beaches, parks and all that Madison has to offer.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24199405 MLS

First Time Offered In 25 Years. This contemporary raised ranch, set on 2.36 secluded acres, is located in a quiet cul-de-sac neighborhood just minutes to town. The living room with hardwood floors features a cathedral ceiling with beams, a wood burning fireplace, floor to ceiling windows with double sliders to a deck with built in bench, perfect for morning coffee or evening enjoyment. The adjacent dining room also has sliders to a patio. The kitchen with breakfast bar is waiting for your personal touches. Down the hall you will find 2 spacious guest bedrooms with large closets that share a hall bath. The primary bedroom with walk-in closet has its own full bath. Downstairs is a large family room with a wood stove to keep things cozy and sliders to an additional patio. The laundry is also located on this level. Though located in a private wooded setting, this home is conveniently located to town, beaches, parks and all that Madison has to offer.

35 Aileen Dr, Madison

$900,000

Build Your Dream Home on Prestigious Lantern Hill Road Discover an exceptional opportunity to own a 1.2acre parcel tucked away on one of Madison's most coveted and private culdesacs. Located at 78 Lantern Hill Road, this hidden gem offers the perfect balance of tranquility and convenience-less than a mile from Madison's beautiful beaches, vibrant town center, boutique shopping, dining, golf, and quick access to I95 for effortless commuting. Surrounded by impeccably maintained, luxury homes-many valued around the $3 million mark-this premier lot provides an ideal canvas for an elegant coastal residence. Mature trees, serene natural surroundings, and underground utilities enhance the setting, making it ready for a highend build that complements the neighborhood's sophistication. Experience the best of shoreline living in Madison, celebrated for its charming village atmosphere, thriving arts and culture, abundant recreation, and pristine coastline. Whether you envision a yearround sanctuary or a summer retreat, this location offers a rare blend of privacy, luxury, and accessibility. Don't miss the chance to build in one of Connecticut's most soughtafter seaside communities.

ACTIVE Status ⋅ 24200319 MLS

Build Your Dream Home on Prestigious Lantern Hill Road Discover an exceptional opportunity to own a 1.2acre parcel tucked away on one of Madison's most coveted and private culdesacs. Located at 78 Lantern Hill Road, this hidden gem offers the perfect balance of tranquility and convenience-less than a mile from Madison's beautiful beaches, vibrant town center, boutique shopping, dining, golf, and quick access to I95 for effortless commuting. Surrounded by impeccably maintained, luxury homes-many valued around the $3 million mark-this premier lot provides an ideal canvas for an elegant coastal residence. Mature trees, serene natural surroundings, and underground utilities enhance the setting, making it ready for a highend build that complements the neighborhood's sophistication. Experience the best of shoreline living in Madison, celebrated for its charming village atmosphere, thriving arts and culture, abundant recreation, and pristine coastline. Whether you envision a yearround sanctuary or a summer retreat, this location offers a rare blend of privacy, luxury, and accessibility. Don't miss the chance to build in one of Connecticut's most soughtafter seaside communities.

78 Lantern Hill Rd, Madison

$3,500

Livw by the shore at 153 Middle Beach Road in Madison, a classic coastal retreat available for an academic rental October 2026 to June 2027. Perfectly positioned in one of Madison's most sought-after beach neighborhoods, this charming home offers the relaxed lifestyle that makes summer on the Connecticut shoreline so special. Wake up to salty sea breezes, enjoy your morning coffee on the spacious front porch, and spend your days just a short stroll from East Wharf Beach, where swimming, sunbathing, paddle boarding, and spectacular sunsets await. From the backyard, launch your kayak and explore the peaceful waters and abundant wildlife of the marshes and creeks that wind through this picturesque shoreline setting. The home comfortably offers four bedrooms, including a main floor bedroom and full bath, inviting living spaces, hardwood floors, and plenty of room to gather after a day at the beach. The sun drenched kitchen has a new refrigerator and stove. Water views, natural beauty, and the easy rhythm of beach living create a truly memorable summer experience. Located just minutes from Madison's vibrant downtown, you'll enjoy boutique shopping, wonderful restaurants, the town green, and local events throughout the season. 53 Middle Beach Road offers the perfect blend of comfort, charm, and waterfront adventure. Also, for sale. See MLS#24164243

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24195739 MLS

Livw by the shore at 153 Middle Beach Road in Madison, a classic coastal retreat available for an academic rental October 2026 to June 2027. Perfectly positioned in one of Madison's most sought-after beach neighborhoods, this charming home offers the relaxed lifestyle that makes summer on the Connecticut shoreline so special. Wake up to salty sea breezes, enjoy your morning coffee on the spacious front porch, and spend your days just a short stroll from East Wharf Beach, where swimming, sunbathing, paddle boarding, and spectacular sunsets await. From the backyard, launch your kayak and explore the peaceful waters and abundant wildlife of the marshes and creeks that wind through this picturesque shoreline setting. The home comfortably offers four bedrooms, including a main floor bedroom and full bath, inviting living spaces, hardwood floors, and plenty of room to gather after a day at the beach. The sun drenched kitchen has a new refrigerator and stove. Water views, natural beauty, and the easy rhythm of beach living create a truly memorable summer experience. Located just minutes from Madison's vibrant downtown, you'll enjoy boutique shopping, wonderful restaurants, the town green, and local events throughout the season. 53 Middle Beach Road offers the perfect blend of comfort, charm, and waterfront adventure. Also, for sale. See MLS#24164243

153 Middle Beach Rd, Madison

$999,000

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.

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24187090 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

$5,700

Available from September 15, 2026, through May 15, 2027, this stunning direct-waterfront academic rental offers an unparalleled coastal lifestyle with breathtaking, panoramic views from almost every room. The bright, sunny interior features an open-concept main level, highlighting a gourmet kitchen with quartz countertops and stainless steel appliances, alongside a generous living and dining area complete with a gas fireplace and walls of glass that frame the ever-changing coastal vistas. Sliders open to an expansive wrap-around deck perfect for relaxing, while the direct-access beach with its natural tidal pools awaits just steps away. The home's flexible layout includes a convenient main-floor bedroom with a full bath and laundry, while the upper level boasts a second bedroom, a full bath, and a one-of-a-kind primary suite featuring soaring ceilings, dramatic walls of glass, and a private balcony for your morning coffee. Please note that this is a strict no pets, no exceptions property.

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24183399 MLS

Available from September 15, 2026, through May 15, 2027, this stunning direct-waterfront academic rental offers an unparalleled coastal lifestyle with breathtaking, panoramic views from almost every room. The bright, sunny interior features an open-concept main level, highlighting a gourmet kitchen with quartz countertops and stainless steel appliances, alongside a generous living and dining area complete with a gas fireplace and walls of glass that frame the ever-changing coastal vistas. Sliders open to an expansive wrap-around deck perfect for relaxing, while the direct-access beach with its natural tidal pools awaits just steps away. The home's flexible layout includes a convenient main-floor bedroom with a full bath and laundry, while the upper level boasts a second bedroom, a full bath, and a one-of-a-kind primary suite featuring soaring ceilings, dramatic walls of glass, and a private balcony for your morning coffee. Please note that this is a strict no pets, no exceptions property.

146 Chittenden Field Ln, Madison

$1,300,000

Welcome to this fabulous one-owner custom home in sought-after Neck River Farms. A gracious, spacious foyer warmly welcomes you inside, setting the tone for the beautifully maintained interior filled with abundant natural light. A dedicated home office with elegant French doors offers the perfect space for working remotely or quiet study. The inviting living room is ideal for entertaining, featuring oversized windows, soaring ceilings, and detailed crown molding. The heart of the home is the well-appointed kitchen with a vaulted ceiling, complete with a large center island, generous pantry storage, and granite countertops. It flows seamlessly into the cozy family room, where a wood-burning fireplace creates a perfect gathering space. Upstairs, you'll find 4 bedrooms plus a versatile guest suite above the garage, complete with a full bath and private back staircase-ideal for extended stays or multigenerational living. The primary bedroom is spacious with a luxurious bath and walk-in closet. The finished basement provides additional flexible space for a playroom, fitness area, or media room. Situated at the end of a cul-de-sac, this home offers privacy on 4.12 acres of beautifully landscaped grounds. The level backyard features a lovely stone patio and plenty of room for a pool. Additional highlights include a newer 3-year-old asphalt shingle roof, new furnace and air handler. A rare opportunity to own a spacious and thoughtfully designed home in a desirable location

5 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24183446 MLS

Welcome to this fabulous one-owner custom home in sought-after Neck River Farms. A gracious, spacious foyer warmly welcomes you inside, setting the tone for the beautifully maintained interior filled with abundant natural light. A dedicated home office with elegant French doors offers the perfect space for working remotely or quiet study. The inviting living room is ideal for entertaining, featuring oversized windows, soaring ceilings, and detailed crown molding. The heart of the home is the well-appointed kitchen with a vaulted ceiling, complete with a large center island, generous pantry storage, and granite countertops. It flows seamlessly into the cozy family room, where a wood-burning fireplace creates a perfect gathering space. Upstairs, you'll find 4 bedrooms plus a versatile guest suite above the garage, complete with a full bath and private back staircase-ideal for extended stays or multigenerational living. The primary bedroom is spacious with a luxurious bath and walk-in closet. The finished basement provides additional flexible space for a playroom, fitness area, or media room. Situated at the end of a cul-de-sac, this home offers privacy on 4.12 acres of beautifully landscaped grounds. The level backyard features a lovely stone patio and plenty of room for a pool. Additional highlights include a newer 3-year-old asphalt shingle roof, new furnace and air handler. A rare opportunity to own a spacious and thoughtfully designed home in a desirable location

77 Silo Hill, Madison

$2,550,000

Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the home is thoughtfully designed for both elegant living and everyday comfort, featuring expansive, light-filled spaces and exquisite millwork throughout. The custom chef's kitchen is a true centerpiece, appointed with premium appliances, striking imported granite countertops, and impeccable detailing. A grand entryway welcomes you with a sweeping staircase and a beautifully crafted coffered ceiling, setting the tone for the quality and sophistication found in every room. Layout designed for first floor primary suite. This is a home for those who appreciate enduring design, superior construction, and a setting that feels worlds away-yet remains close to everything Madison has to offer.

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24159028 MLS

Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the home is thoughtfully designed for both elegant living and everyday comfort, featuring expansive, light-filled spaces and exquisite millwork throughout. The custom chef's kitchen is a true centerpiece, appointed with premium appliances, striking imported granite countertops, and impeccable detailing. A grand entryway welcomes you with a sweeping staircase and a beautifully crafted coffered ceiling, setting the tone for the quality and sophistication found in every room. Layout designed for first floor primary suite. This is a home for those who appreciate enduring design, superior construction, and a setting that feels worlds away-yet remains close to everything Madison has to offer.

24 Indigo Trl, Madison

$1,975,000

Modern luxury meets sustainable living in a premier location. Set on more than two private acres in one of the area's most sought-after neighborhoods, this brand-new contemporary home offers a bright, open-concept design that blends sophisticated style with everyday comfort. At the heart of the home, the chef's kitchen impresses with a Sub-Zero refrigerator, Wolf appliances, custom cabinetry, and stunning quartzite countertops. The space flows effortlessly into the expansive great room, where a dramatic floor-to-ceiling fireplace creates a striking focal point for gathering and entertaining. The main-level primary suite serves as a private retreat, featuring its own stone fireplace, spacious walk-in closet, and luxurious ensuite bath. The walkout lower level adds exceptional flexibility with two additional bedrooms, a shared full bath, two generous flex spaces ideal for a home office, gym, media room, or recreation area, plus an additional half bath. Designed with both efficiency and longevity in mind, the home is equipped with an energy-efficient geothermal heating and cooling system, providing year-round comfort while helping reduce utility costs. A premium metal roof offers outstanding durability, low maintenance, and lasting protection for decades to come. Additional features include a two-car garage and exceptional privacy, all just minutes from Madison's charming village center, beautiful beaches, and convenient access to I-95.

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24155109 MLS

Modern luxury meets sustainable living in a premier location. Set on more than two private acres in one of the area's most sought-after neighborhoods, this brand-new contemporary home offers a bright, open-concept design that blends sophisticated style with everyday comfort. At the heart of the home, the chef's kitchen impresses with a Sub-Zero refrigerator, Wolf appliances, custom cabinetry, and stunning quartzite countertops. The space flows effortlessly into the expansive great room, where a dramatic floor-to-ceiling fireplace creates a striking focal point for gathering and entertaining. The main-level primary suite serves as a private retreat, featuring its own stone fireplace, spacious walk-in closet, and luxurious ensuite bath. The walkout lower level adds exceptional flexibility with two additional bedrooms, a shared full bath, two generous flex spaces ideal for a home office, gym, media room, or recreation area, plus an additional half bath. Designed with both efficiency and longevity in mind, the home is equipped with an energy-efficient geothermal heating and cooling system, providing year-round comfort while helping reduce utility costs. A premium metal roof offers outstanding durability, low maintenance, and lasting protection for decades to come. Additional features include a two-car garage and exceptional privacy, all just minutes from Madison's charming village center, beautiful beaches, and convenient access to I-95.

81 Strawberry Hill Rd, Madison

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