Homestead Madison

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  • Interior

    An elegantly decorated dining room with a chandelier, showcasing a set dining table and ornate chairs.
  • Decor

    A cozy vintage-style living room with wooden floors, skylights, and a decorative bookshelf.
  • Living Room

    A cozy and stylish living room with comfortable seating and elegant decor.
  • Bedroom

    A cozy bedroom with hardwood floors, featuring a bed, television, and built-in shelves.
  • Windows

    Cozy living room with bookshelves and colorful decor.
  • Rug

    A cozy and well-decorated bedroom featuring a bed, chairs, dresser, and rug with natural light from windows.

Homestead Madison

Information last verified:

391 Boston Post Rd, Madison, CT 06443

For more information about senior living options: (844) 490-3973

4.9 from 110 reviews
5 stars
107
4 stars
2
3 stars
0
2 stars
0
1 stars
1

Seniors.FYI Elite Community Awards

Top 5% Senior Living Community in 2025Top 5% Senior Living Community in 2026

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Homestead Madison Costs & Pricing

Homestead Madison offers a competitive monthly rate of $4,000 for a one-bedroom unit, significantly lower than both New Haven County and the broader Connecticut market, where costs average around $6,325 and $6,383 respectively. This substantial price difference highlights Homestead Madison's commitment to providing quality living options at a more accessible price point. For individuals seeking affordable yet comfortable accommodation in a desirable location, Homestead Madison represents an attractive choice without compromising on value compared to its regional counterparts.

Floor plansHomestead MadisonNew Haven CountyConnecticut
1 Bedroom$4,000$6,325$6,383

Overall Review of Homestead Madison

Pros

  • pro The Homestead is described as a warm, welcoming, and beautifully appointed bed and breakfast.
  • pro The staff are incredibly friendly, attentive, and helpful.
  • pro Each room is beautifully decorated, spacious, and impeccably clean, with charming touches like in-room fireplaces and private patios.
  • pro Breakfast is consistently delicious and thoughtfully prepared, with options for dietary needs.
  • pro The inn's ambiance blends charm, history, and modern comforts, making guests feel at home.
  • pro Heartman the inn dog is a beloved and friendly presence that enhances the experience.
  • pro The common areas and outdoor spaces—fireplaces, fire pits, and cozy seating—offer a relaxing, inviting atmosphere.
  • pro The location is praised for being close to beaches, town, and attractions, making it a perfect getaway.

Cons

  • pro A guest described their Fourth of July stay as very unpleasant due to a power outage and the inn lacking a generator.
  • pro The same guest claimed the staff were rude and inconsiderate, and they were asked to move so photos could be staged.
  • pro They added that they would never recommend visiting the inn to anyone.
  • pro A guest noted that a dog on the premises barked and growled at children and other guests, detracting from the welcome.
  • pro One reviewer felt the overall experience was not unforgettable, even though many other aspects were praised.

Review

Homestead Madison is best suited for couples and small groups who want a boutique, high-touch New England inn experience that feels intimate, personal, and richly curated. It suits those who prize walking-distance access to Madison’s shore town charm, a warm welcome that feels more like family than a check-in, and rooms that pair comfort with character. Guests drawn to nostalgia, eclectic decor, and the idea of a home-away-from-home atmosphere will find it especially compelling: each room offers its own vibe, a private patio or generous bath, and thoughtful amenities that make a weekend escape feel special rather than generic.

There are clear reasons to consider alternatives, however. For travelers who require a strictly predictable hotel routine, a fully dog-free environment, or total privacy without staff presence, something more conventional could be preferable. A few guests with sensitivities to dogs or who encountered run-ins with a resident dog during a stay may want to choose another property. Those who dread even brief power interruptions or who rely on a generator backup during storms should weigh the shoreline realities against the inn’s inherent charm. In short, a handful of visitors will prefer a more conventional hotel experience or a property that emphasizes silence and unshared spaces above the intimate bustle of a B&B.

The strongest pros at Homestead Madison consistently offset the most notable drawbacks. The hospitality is extraordinary: the owner and a tightly knit team deliver a level of warmth, attentiveness, and storytelling that makes every guest feel seen and valued. Rooms are not merely clean and comfortable; they are well appointed with upgrades that feel luxurious in a homey way, heated towel warmers, vitamin-infused shower heads, large, high-thread-count linens, and in-room record players that invite a little musical nostalgia. Add in a superb breakfast, abundant snacks throughout the day, and a coffee program that rivals any boutique inn, and the value becomes clear. The property’s grounds and common spaces are both inviting and versatile, offering fire pits, outdoor seating, bikes, beach chairs, towels, and even beach passes, which transform a Madison weekend into a relaxed, all-in-one experience rather than a series of separate errands.

The cons, when they appear, are manageable and often outshined by the positives. A rare but memorable critique points to a power outage without backup, which can unsettle families with kids and impact the immediacy of comfort. Another downbeat note touches on a moment of perceived insensitivity during a hectic service moment; such instances are not representative of the overall track record, but they illustrate that even in a celebrated B&B, a single misstep can undermine a guest’s mood. The practical takeaway is clear: for visitors who want unwavering predictability and uninterrupted power during storm season, a larger hotel with robust contingency plans may be preferable. Yet those same guests should acknowledge that the bulk of stays are brisk, personal, and warmly organized, with staff going the extra mile to anticipate needs and tailor experiences.

For decision-makers weighing this against alternatives, the balance of pros and cons tilts decisively toward Homestead Madison when the objective is an immersive, memorable stay rather than a routine hotel visit. The inn’s greatest strength, a genuine sense of place built through meticulous detail, a lively but never overbearing staff, and amenities that truly feel thought out, delivers a premium experience that many guests report as worth every premium dollar. The breakfast, the ability to snack or sip coffee at any hour, the well-curated common rooms, and the access to beaches and town attractions all combine to create a low-stress, high-pleasure itinerary. Even guests who arrive as skeptics often leave convinced they’ve discovered a “home away from home” that elevates a simple getaway into a cherished memory.

Logistically, Homestead Madison works beautifully for weekend escapes, anniversaries, family gatherings, or small work retreats. The location is convenient for Madison’s main drag, beaches, and nearby towns; the rooms are spacious, impeccably clean, and surprisingly quiet for a labeled B&B; and the staff, especially the front-of-house team and Ray at breakfast, consistently demonstrates warmth, attentiveness, and a knack for small, meaningful touches. The property also leans into a distinctive lifestyle vibe: record players in each room, a rotating display of memorabilia, quirky decor, and a garden-like, dog-friendly ambience that invites lingering conversations, leisurely readings, and impromptu games around the outdoor fire pits. For travelers who want all that without sacrificing modern comfort, the draw is compelling.

In the end, Homestead Madison is a standout choice for couples seeking romance with a strong sense of place, families aiming for a relaxed, homey weekend, or professionals needing a refreshing, well-supported retreat that still feels personal. It is not the right pick for those who require absolute predictability, a dog-free guarantee, or a hotel-grade guarantee of silence and uninterrupted power. When the criteria are warmth, unique atmosphere, intimate service, and rich, inclusive comforts, this inn delivers with confidence. Book early, request a room with a private patio if possible, and lean into the hospitality, the staff will ensure the experience exceeds expectations and makes Madison feel a little more like home every time.

Features

Types of Care

  • Independent Living Independent LivingIndependent living communities are important for seniors because they offer a safe and supportive environment where older adults can live independently while still having access to amenities and services that enhance their quality of life. These communities provide social opportunities, recreational activities, and assistance with daily tasks, promoting overall well-being and allowing seniors to maintain their independence for as long as possible.

Amenities

  • Activities off-site Activities off-siteEngaging in off-site activities is crucial for seniors to maintain social connections, stay active, and stimulate their minds. It promotes overall well-being and helps combat feelings of isolation and loneliness.
  • Activities on-site Activities on-siteActivities on-site are important for seniors because they provide opportunities for socialization, mental stimulation, physical activity, and overall well-being. Engaging in activities can help seniors stay active, maintain their independence, and improve their quality of life.
  • Air-conditioning Air-conditioningAir conditioning is important for seniors as they are more vulnerable to heat-related illnesses and may have underlying health conditions that make it difficult for them to regulate their body temperature. It helps to keep them comfortable, safe, and healthy in hot weather.
  • Bath tubs Bath tubsBath tubs are important for seniors because they provide a safe and relaxing way to bathe, helping to prevent slips and falls while promoting independence and overall well-being.
  • Cable or satellite TV Cable or satellite TVCable or satellite TV is important for seniors because it provides entertainment, news, and companionship, helping to combat loneliness and boredom. It also offers a wide range of programming options tailored to different interests and preferences.
  • Devotional services off-site Devotional services off-siteDevotional services off-site are important for seniors as they provide spiritual nourishment, social engagement, and a sense of community outside of the senior living facility. This can enhance overall well-being and help combat feelings of isolation and loneliness often experienced by older adults.
  • Ground floor units Ground floor unitsGround floor units are important for seniors because they provide easy accessibility, reduced risk of falls and injuries, and convenience for those with mobility issues. Seniors can avoid climbing stairs or using elevators, making daily tasks and activities more manageable and enjoyable.
  • Indoor common areas Indoor common areasIndoor common areas are crucial for seniors as they provide a space for socialization, recreation, and community engagement, promoting overall well-being and reducing feelings of isolation and loneliness.
  • Outdoor common areas Outdoor common areasOutdoor common areas are important for seniors as they provide a space for socialization, physical activity, and relaxation. Being outside in nature can improve mood and overall well-being, while also encouraging movement and engagement with others. These spaces can help combat feelings of isolation and promote a sense of community among residents.
  • Private bathrooms Private bathroomsPrivate bathrooms are important for seniors in senior living communities because they provide independence, dignity, and comfort. Having a private bathroom allows seniors to maintain their personal hygiene routines without the need for assistance, promoting a sense of autonomy and privacy. Additionally, private bathrooms help prevent the spread of infections and provide a safe and clean environment for seniors to navigate safely.
  • Respite or short term stays offered Respite or short term stays offeredRespite or short term stays provide seniors with a temporary solution when their regular caregiver is unavailable, offering them the opportunity to receive additional care and support during times of need, while also giving caregivers a chance to rest and recharge.
  • Wi-Fi/high-speed internet available Wi-Fi/high-speed internet availableWi-Fi/high-speed internet is important for seniors to stay connected with loved ones, access online resources, and participate in virtual activities to combat feelings of loneliness and isolation. It also allows them to easily manage healthcare needs, access entertainment, and engage in lifelong learning opportunities.

Dining

  • Anytime dining Anytime diningAnytime dining is important for seniors because it allows them the flexibility to eat when they are hungry, rather than being restricted to set meal times. This can be especially beneficial for those with medical conditions or medications that affect their appetite, as well as those who may have difficulty adhering to a strict dining schedule. Overall, anytime dining promotes independence and overall well-being for seniors in senior living communities.
  • Gluten-free Gluten-freeGluten-free options are important for seniors as they are more prone to digestive issues and dietary sensitivities. Offering gluten-free meal choices in senior living communities can help improve their overall health and well-being.
  • Guest meals Guest mealsGuest meals are important for seniors living in senior living communities because they provide an opportunity for socialization and companionship. Sharing a meal with friends, family, or new acquaintances can help combat feelings of loneliness and isolation, promote a sense of community, and enhance overall well-being. Additionally, guest meals allow seniors to enjoy delicious food in a comfortable setting without the hassle of cooking or cleaning up, making dining a pleasurable and stress-free experience.
  • International cuisine International cuisineInternational cuisine is important for seniors because it offers a variety of flavors, ingredients, and cultural experiences that can help keep their meals interesting and enjoyable. Trying new dishes can also stimulate the senses and provide different nutrients that contribute to overall health and well-being. Additionally, exploring international cuisine can bring back fond memories of travels or childhood experiences, making mealtime more nostalgic and fulfilling for seniors.
  • Low / no sodium Low / no sodiumLow/no sodium options are important for seniors because excessive sodium intake can lead to high blood pressure, heart disease, and other health issues commonly experienced by older adults. By choosing low/no sodium foods, seniors can better manage their health and reduce their risk of developing these conditions.
  • Meals provided Meals provided"Meals provided" are crucial for seniors in assisted living communities as it ensures they have access to nutritious, balanced meals without the stress of meal planning and preparation. This can help promote overall health and well-being for seniors who may have limited mobility or cognitive abilities.
  • No Sugar No SugarNo sugar diets are important for seniors because they can help prevent or manage chronic conditions such as diabetes, heart disease, and obesity. Sugar can also contribute to cognitive decline and inflammation in the body, so reducing sugar intake can lead to overall improved health and well-being in older adults.
  • Restaurant style dining Restaurant style diningRestaurant style dining is important for seniors as it offers them a social and enjoyable dining experience, promotes healthy eating habits, and provides personalized menu options to cater to their dietary needs and preferences. This type of dining setting can enhance their overall quality of life and create a sense of community within the senior living facility.
  • Room service Room serviceRoom service is important for seniors in a senior living community because it provides convenience and allows them to have their meals delivered directly to their room. This can be especially beneficial for seniors who may have mobility issues or difficulty accessing the dining area. Room service ensures that seniors are able to receive nutritious meals without having to navigate through the facility, allowing them to maintain their independence and overall well-being.

Activities

  • Activities off-site Activities off-siteEngaging in off-site activities is crucial for seniors to maintain social connections, stay active, and stimulate their minds. It promotes overall well-being and helps combat feelings of isolation and loneliness.
  • Activities on-site Activities on-siteActivities on-site are important for seniors because they provide opportunities for socialization, mental stimulation, physical activity, and overall well-being. Engaging in activities can help seniors stay active, maintain their independence, and improve their quality of life.
  • BBQs or picnics BBQs or picnicsBBQs or picnics provide seniors with social interaction, enjoyment of the outdoors, and a sense of community, contributing to their overall well-being and quality of life.
  • Birthday parties Birthday partiesBirthday parties are important for seniors as they provide an opportunity for celebration, socialization, and joy. They allow seniors to feel special and appreciated, boosting their mood and overall well-being. Additionally, birthday parties can help combat feelings of isolation and loneliness by fostering connections with friends, family, and community members.
  • Devotional activities offsite Devotional activities offsiteDevotional activities offsite are important for seniors because they provide social engagement, spiritual growth, and a sense of community outside of their living environment. This can improve overall well-being, mental health, and combat feelings of isolation or loneliness.
  • Happy hour Happy hourHappy hour is important for seniors as it provides a social activity that promotes camaraderie and reduces feelings of loneliness or isolation. It also offers an opportunity for older adults to relax, unwind, and enjoy some drinks or snacks in a fun and welcoming atmosphere.
  • Holiday parties Holiday partiesHoliday parties are important for seniors because they provide opportunities for socialization, community involvement, and mental stimulation. These festive events offer a sense of belonging and connection during a time that can be lonely for many older adults. Additionally, participating in holiday celebrations can boost mood and overall well-being for seniors living in senior living communities.
  • Live dance or theater performances Live dance or theater performancesLive dance or theater performances are important for seniors because they provide opportunities for socialization, mental stimulation, and emotional engagement. These performances can help combat feelings of isolation and loneliness, while also offering a sense of connection to the arts and culture. Additionally, watching live performances can bring joy and create lasting memories for seniors in their later years.
  • Live musical performances Live musical performancesLive musical performances can provide seniors with a sense of joy, nostalgia, and connection. Music has the power to evoke emotions and memories, improve mood and cognitive function, and foster social interaction among seniors. It can also serve as a form of therapy and stress relief for older adults, making it an important activity to include in senior living communities.

Description

Homestead Madison is a vibrant assisted living community located in Madison, CT. Our community offers a wide range of amenities to ensure our residents' comfort and well-being. Residents can enjoy engaging activities right on-site, as well as take advantage of the beautiful indoor and outdoor common areas. Each apartment is equipped with air-conditioning for ultimate comfort, and private bathrooms for convenience and privacy. With Wi-Fi/high-speed internet available throughout the community, residents can stay connected with loved ones and explore online.

At Homestead Madison, we understand the importance of providing nutritious and delicious meals that cater to individual dietary needs. Our dining options include gluten-free, low/no sodium, no sugar, and international cuisine. Residents can enjoy restaurant-style dining or opt for room service for added convenience.

Our community also encourages an active and social lifestyle through various activities. Residents can participate in BBQs or picnics, birthday parties, devotional activities offsite, happy hour events, holiday parties, as well as live dance or theater performances and live musical performances.

Convenience is at our residents' fingertips with cafes, parks, pharmacies, physicians, restaurants all within close proximity to our community. Transportation services are also available for easy access to nearby amenities.

At Homestead Madison, we strive to provide a welcoming and engaging environment where our residents can maintain their independence while receiving the assistance they need.

Nearby Places of Interest

This part of Madison, Connecticut offers a variety of amenities that would make it a suitable option for senior living. With several parks nearby such as Madison Surf Club and Hammonasset Beach State Park, residents can enjoy the outdoors and stay active. There are also a number of reputable restaurants in the area including Christy's Madison Inne and Cafe Allegre, providing convenient dining options. In terms of healthcare, there are various physicians' offices as well as pharmacies in close proximity, ensuring easy access to medical services. Additionally, transportation options like the Guilford Train Station are available for those who may not drive. Overall, this neighborhood provides a mix of leisure activities, healthcare facilities, and dining establishments that cater to the needs of seniors looking to reside in Madison.

Parks

  • Madison Surf Club (0.6 miles)
  • Rollwood Park (3.1 miles)
  • Hammonasset Beach State Park (3.2 miles)
  • Guilford Town Green (3.5 miles)
  • Nut Plains Park (4 miles)
  • Chatfield Hollow State Park (6.3 miles)
  • Foote Memorial Park (10.1 miles)

Restaurants

  • Christy's Madison Inne (0.6 miles)
  • Steamed (0.9 miles)
  • Cafe Allegre (1 miles)
  • Jia Mei Asian Kitchen (1.1 miles)
  • Bradley and Wall Gourmet Foods (1.2 miles)
  • McDonald's (2 miles)
  • Guilford Lobster Pou (2.7 miles)

Physicians

  • Connecticut Pediatric Otolaryngology (0.7 miles)
  • Dr Serle Epstein (0.8 miles)
  • Urology Center (0.8 miles)
  • County Obgyn (0.9 miles)
  • Leon A. Goldstein, MD (0.9 miles)
  • Ear, Nose and Throat Specialists of Connecticut (0.9 miles)
  • Alicia R. Guidone, D.P.M. (0.9 miles)

Pharmacies

  • CVS Pharmacy (0.9 miles)
  • CVS Pharmacy (3.7 miles)
  • Walgreens (3.8 miles)
  • CVS Pharmacy (4.6 miles)
  • Walgreens (5.6 miles)
  • Killingworth Family Pharmacy (5.7 miles)
  • Bluepoint Wellness Of CT (8.3 miles)

Transportation

  • Shore Line East - Guilford Train Station (3.1 miles)

Hospitals

  • Middlesex Hospital Madison Outpatient Blood Drawing Facility (3.1 miles)
  • Yale New Haven Hospital Blood Drawing Station (10.2 miles)
  • Harbor House (10.4 miles)
  • Hospital of Saint Raphael (10.7 miles)

Cafes

  • Cilantro Specialty Foods (3.5 miles)
  • Panera Bread (5 miles)
  • Turtle Cafe (8.7 miles)
  • Starbucks (11 miles)
  • Savour Cafe and Bakery (11.4 miles)

Frequently Asked Questions

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